I came across a headline last week that I wish I’d written.

White Collar Sweatshop.

It’s from a piece in Aeon — not a legal publication, not an industry trade. A psychology magazine.

That detail alone should tell you something.

By the end of the 1980s, lawyers at large firms were experiencing depression at five to six times the rate of the general population. One in five abused alcohol. Attorneys held the highest suicide rate of any profession. Aeon

And yet — the applications kept coming.

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The line that actually stops you cold

Most people reading that essay will linger on the horror statistics. The hours. The attrition. Associates given menial tasks — proofreading, document review — with no idea how their work fit into any larger picture. A five-year attrition rate that had climbed above 80 percent by the early 2000s.

Those are bad. But they’re not the most revealing part.

This is:

The law degree, the author notes, had become the degree of choice for people who would rather not make irrevocable choices. For those who lacked unshakable convictions about what they wanted to do with their lives. Who needed time. Room. Psychic slack.

Sit with that for a moment.

The most demanding professional path many people will ever walk — built, in part, on the foundation of not quite deciding.

That’s not a story about law firms. That’s a story about identity. About what it costs to defer the real question long enough that the institution answers it for you.

I know what some of you are thinking

“That was the 80s.”

“That’s BigLaw. That’s New York. That’s not us.”

Maybe. But here’s a more honest question: when was the last time you asked what you were actually building — inside the career, not just around it?

Because the sweatshop was never just a place. It was a posture. A way of relating to the work that put endurance above meaning, throughput above growth, presence above purpose.

And that posture has a very long shelf life.

What keeps people coming back anyway

This is the part that genuinely interests me.

The profession is hard. Everyone knows it’s hard. The research has been public for decades. And yet the law degree remains one of the most sought-after credentials in the world.

There are real reasons for that — the income, the status, the feeling of working on something that actually matters. I’m not dismissing any of it.

But underneath the obvious reasons, there’s something more uncomfortable:

When you’re not sure who you are yet, a demanding institution is oddly comforting. It tells you what to do. It tells you what good looks like. It gives you a rank and a rung and a set of rules.

It answers the question you haven’t been able to answer yourself.

The problem isn’t that the institution is demanding. The problem is what you give up when you let it do your deciding for you.

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The professionals I work with know this feeling

They didn’t sleepwalk into their careers. They made considered choices, passed hard tests, earned their seats.

But somewhere between the beginning and now, the work started working on them more than they were working on it.

The hours didn’t just increase. They became identity.

The performance didn’t just matter. It became worth.

The title didn’t just describe a role. It started describing a self.

And one day — usually not dramatically, usually quietly — something surfaces. A question that doesn’t have an easy answer. Is this actually what I want? Or is this just what I became?

That question is not a crisis. It’s an invitation.

What I know to be true

The professionals who navigate this well aren’t the ones who escape the demands. They’re the ones who get clear — really clear — on why they’re there, what they’re building, and what they refuse to trade away.

That clarity isn’t soft. It’s strategic. It’s the difference between a career that accumulates and one that compounds.

It’s also the work most high performers never get to — because the urgent keeps crowding out the important, and the institution keeps rewarding the people who don’t slow down long enough to ask.

Here’s what I want to know

Not rhetorically. Genuinely.

If you stripped away the title, the income, and the external signal of your position — what would you say you’re actually building?

And is that still the thing you want to be building?

Read the full Aeon essay here or pre-order Gottlieb’s book, “Yuppies” here. It’s worth your full attention.

If this hit a nerve, I’m running a free live session called Building What Lasts on May 5th. It’s for law partners who’ve built successful careers and are now asking a harder question: what do I want this to actually be for? Reserve Your Spot Here here.

→ Take the Best Next Move Assessment here.

→ Or if you’d rather just talk — book a call.

There’s a particular kind of misery that high-performers know well.

You’re good at what you do.

Actually - you’re probably really good at it.

The work gets done - well. Clients are happy - sometimes even - ecstatic?

But, something has gone flat. Not dramatically. Not in a way you could point to in a conversation.

More like when you are driving a car and you know something is up, but can’t tell what, until you realize the tire is completely flat and it’s been leaking for at least a couple of days now.

Most people call this burnout. But, I’m not sure that’s exactly it.

Sometimes what feels like burnout is something quieter: you’ve stopped learning, and your brain knows it before you do.

The Taxonomy You Never Heard Of

In 1956, an educational psychologist named Benjamin Bloom proposed a hierarchy of cognitive engagement. It wasn’t designed for lawyers or professionals — it was meant for teachers designing curricula. But it maps onto something real about how we experience work.

The levels, simplified:

• Remember & Understand — You’re absorbing. Taking in information, making sense of it.

• Apply & Analyze — You’re executing. Using what you know, breaking down problems, finding patterns.

• Evaluate & Create — You’re judging. Making decisions that require wisdom, not just knowledge. Building something new.

Here’s what matters: each level up requires more of you. Not more hours. More you — your judgment, your perspective, your willingness to be wrong.

Where Most Professionals Get Stuck

Early in a career, every day is learning. You’re in over your head, constantly stretching. It’s stressful, but it’s alive.

I recall this period vividly in my legal practice. The first couple of years were fantastic - each file was a new challenge that required me to really get into learning what was at stake, what the law said, what paperwork was required, the industry standards and so forth.

It was fun. In fact, I remember it as being one of the best parts of my career (legal or otherwise).

Then competence arrives.

You master the patterns. You know the playbook. And gradually, you settle into the middle of the taxonomy. Apply and Analyze. Over and over.

This is the trap: you’re doing complex work, but you’re not growing. The cognitive difficulty is real, but the cognitive challenge is gone. Your brain is running an old program very efficiently.

And efficiency, it turns out, doesn’t feel like meaning.

The Stages of Competence

As a bit of a diversion, let’s look at the work of Noel Burch. He developed the idea of the different stages of learning in the 1970s when he worked for Gordon Training International.

Here’s how it basically looks:

Stage 1: Unconscious Incompetence. You don’t know what you’re doing. And, you don’t know that you don’t know what you’re doing. This is the 13 year old that steals his parents’ car. He has no idea how badly this is going to go - which is why he is doing it.

Stage 2: Conscious Incompetence. You know that you aren’t very good at what you’re doing. And this is how you learn - because you are incompetent, you have reason to become competent. This is the 16 year old with the learning permit. She realizes she’s a terrible driver, so, takes lessons or practices daily to get better (and to avoid accidents/crushing her parents’ car).

Stage 3: Conscious Competence. You know that you can do the thing, and do it well. But, you need to pay considerable attention to what you are doing in order to keep doing it well. This is the 19 year old driver - been doing it long enough to know what they are doing, but still needs to really pay very close attention to every detail in the car and on the road (no music, no talking) to make sure they are driving properly.

Stage 4: Unconscious Competence. You are so good at what you do, that you don’t even realize you are good at it. You just do it without even thinking. For some, this is the “flow state”. Or, it’s the F1 driver taking your Subaru out on the road - they are so good at driving that they don’t really even think about what they are doing. The car is simply an extension of them, and they maneuver it in the world with unthinking ease.

The Connection Between Learning and Meaning

Turning back to Bloom’s Taxonomy.

This isn’t just theory. There’s a reason your first year felt more meaningful than your fifteenth, even though you were objectively worse at the job.

Learning is connective tissue. When you’re genuinely learning — not accumulating information, but being changed by what you encounter — you feel tethered to the work. You’re in it.

And, once you become unconsciously competent - the thing we are all aiming for - you plateau. The curve doesn’t go upward as much any more. You can stop trying.

And when you stop trying - when you don’t really need to think much anymore to be good at what you’re doing - you get bored.

And when you get bored - you get disconnected. The tether loosens. You start to float. You’re still performing, but you’re watching yourself perform.

That’s the dissociation people mistake for burnout.

The real question isn’t “am I working too much?” It’s “when was the last time my work required me to think in a way I hadn’t thought before?”

Climbing Again

This is usually the point when people face a major choice: quit or commit?

I’d argue the fix isn’t necessarily quitting.

It’s not a sabbatical (though rest matters).

It’s also not necessarily committing - at least not in the way we customarily think, which is to double down on the work we’re already doing, get busier, and just grind.

It’s actually something like a bit of a hybrid of the two: commit re-engaging at a higher level of the taxonomy.

What does that look like?

It looks like moving from executing someone else’s strategy to evaluating whether the strategy is right. From analyzing problems to creating frameworks others can use. From knowing the answer to asking a better question.

It might mean mentoring in a way that forces you to articulate what you actually believe, not just what you know. It might mean taking on a matter that scares you. It might mean building something — a practice, a team, a body of work — that didn’t exist before you decided it should.

The point isn’t to add more. It’s to move up.

If this hit a nerve, I’m running a free live session called Building What Lasts on May 5th. It’s for law partners who’ve built successful careers and are now asking a harder question: what do I want this to actually be for? Reserve Your Spot Here here.

→ Take the Best Next Move Assessment here.

→ Or if you’d rather just talk — book a call.

“But, I already have a therapist.”

I hear this a lot.

Sometimes, it’s intended to be a question. Like - “I already talk to someone about my stuff. What would coaching add?”

Other times, it’s more like a deflection: “Um….I’m good. Thanks.”

From my end, both are worth taking seriously.

But first, I’m going to put this out there:

I have been in therapy for most of my adult life. Actually, since my first year of law school (which may say more about law school than me or therapy - but, I digress).

Over the years, on and off, different therapists, different modalities, different “issues”.

It has been one of the most important investments I have ever made in myself.

There are things I know about who I am, why I do what I do, and where my edges are that I simply would not know without that work.

In fact, without my therapists over the years, I wouldn’t have:

1. left legal practice

2. started a legal practice

3. pursued art, film and other things

4. gotten married

5. had children

6. left law again

7. do what I do now

And, I don’t mean that in the sense that, “Oh, therapy was the prime mover that set that all in motion.”

No. I mean that each of those things was a specific challenge that I needed to get through in, and with the help of, therapy.

So, I know what therapy does and what it’s capable of.

And you might ask, “So, are you selling therapy here?”

Well, yes. In a way.

But I am also someone who built a coaching practice specifically because I kept seeing something therapy wasn’t addressing for me and for the people I have coached and mentored and spoken with over the years.

Therapy and coaching are not the same thing. And, they aren’t intended to be.

But, they’re also not competing. They are not mutually exclusive. Having one doesn’t mean you don’t need the other.

Here’s how1.

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Therapy looks back. Coaching looks forward.

Therapy is, at its core, a process of understanding. It asks: how did you get here? What happened to you, and how is that still showing up? It moves backward before it moves forward - and for good reason. There are many things (perhaps most things) in life that cannot be addressed any other way.

Coaching meets you in the present. Not because your history doesn’t matter - it does, and good coaching will bring that in - but because the primary movement is forward. We start with where you are, what you want, and what’s in the way. The past informs that work. It doesn’t drive it.

For a lawyer who knows something isn’t working and wants to figure out what to do about it, that distinction matters. You don’t always need to excavate your childhood to figure out why you’ve been measuring your worth by your billable hours. Sometimes you just need someone to help you see it clearly and build something different.

Therapy asks “Why?” Coaching asks “What next?”

Now, from the outset, this isn’t entirely true. In fact, “Why?” might be one of the most used questions in my conversations with people and teams.

It’s that it’s being asked differently.

Not, “Why are you this way?” or “Why did you end up in this position?”

Rather, “Why aren’t you taking the action you want to take?”

For many of the people I work with, the first why has already been answered. They know why they’re exhausted. They know why they can’t set boundaries. They know why they keep saying yes when they mean no. They’ve done enough therapy, or enough reflection, to have real insight into themselves.

What they don’t have is a structure for change. A way to take what they know and actually do something different with it. That’s the “Why?” we’re interested in.

Therapy is open-ended. Coaching is time-limited and targeted.

Therapy, done well, is a long relationship. It unfolds at the pace the work requires. I have no plans of stopping therapy any time soon - and it’s been close to 20 years.

Coaching is different by design. We work together for a defined period — sometimes 90 days, sometimes over a year - on one or two specific areas where something needs to shift. The limitation isn’t so much about time but about the focus that a limitation in time, or issue, or questions, can create. That’s a feature - not a bug. And with that focus, momentum and accountability can come into fruition in a way that perhaps happens less in a more open-ended setting.

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When therapy is the right call.

If the path to your next step runs primarily through your wounds - trauma, say, or deep psychological patterns that are running your life in ways you don’t yet know or simply can’t see or interrupt - therapy is the right call.

Not coaching. Therapy.

If you are dealing with clinical depression or anxiety that is affecting your ability to function. If you have experienced significant trauma that hasn’t been addressed. If you suspect undiagnosed ADHD or other mental health challenges that are shaping how you work and live. These are not coaching conversations. These are clinical ones, and they deserve clinical care.

I say this not to protect my professional boundaries - I say it because sending someone to coaching when what they need is therapy is a disservice. I have referred clients to therapists. I will continue to do so.

It is one of the most important services I can provide.

Coaching works best when you have enough stability and self-awareness to do forward-focused work. When the foundation is solid enough to build on. When the primary question isn’t “What happened to me?” but “What do I do now?”

If you’re not sure which category you’re in - that might be something work looking into (a classic coach/therapist expression in itself). With a therapist, or with a coach, or both.

Which brings me to the thing I actually believe most strongly.

My honest opinion: Do Both.

This is not me telling you to blow your budget on personal or professional help.

But, I will say - the people I work with who do both make the fastest progress. That’s not a coincidence.

Here’s why: therapy and coaching feed each other. Therapy gives you insight and coaching gives you structure to use the insight.

When both are happening simultaneously, the work compounds. You understand yourself more deeply and you’re building something new at the same time.

I have had clients who came to me already in therapy and found that coaching gave their therapy new material to work with. And I have had clients who started coaching and realized, midway through, that there was something underneath the surface that needed therapeutic attention - and we adjusted accordingly.

I work with both a coach and a therapist. My goal was never to replace therapy - for myself or for others. And, it was never to compete with it either. The goal is to help you build a life and a career that actually fits - and sometimes that requires more than one kind of support.

If you have a therapist you trust, tell them you’re thinking about coaching. In my experience, most good therapists welcome it. They understand that different tools do different things.

And if you don’t have a therapist - and you’re feeling the weight that many of the lawyers I work with are carrying - it might be worth considering. Not instead of coaching. In addition to it.

So, here’s where I’ll leave you: if you’re asking “should I see a therapist or a coach?” — you’re probably asking the wrong question.

The better question is: what kind of work do I actually need right now?

If the answer is that you need to understand yourself more deeply, start with therapy. Or go back to it. It’s worth it.

If the answer is that you already have enough insight, and what you’re missing is a structure to actually do something with it - that’s coaching.

And if the answer is that you need both — that the insight and the structure need to happen at the same time — then build both. You don’t have to choose.

If you’re trying to figure out where to start — the free Best Next Move Assessment was built for exactly this moment. It takes about five minutes and will give you a clearer picture of where you actually are.

→ Take the assessment here.

→ Or if you’d rather just talk — book a call.

The last time I participated in an art fair with my photography is a stand out lesson in being rejected.

I had a beautiful booth. Great presentation. Nice little details like flyers and cards and flowers and furniture. I had great placement - first row in a high-ceilinged, white presentation hall where hundreds of other artists were showing their work - and I was one of the first people saw when they came in. I was in a position for success.

That week, I had chosen to show a selection of photos that I had made on a recent trip to West Texas and thereabouts. I wasn’t that crazy about the pieces, but I needed work to show, and since my other pieces like this had done well in past years, I thought why not - these are what buyers usually want.

I thought they would sell. I thought they would do well.

Well, day one went by, and nothing sold. Then day two. Then day three.

By day four, I was starting to worry. Why wasn’t anything selling? Why were there no red dots on the wall?

I didn’t sell one piece that week. It sucked.

And, I haven’t shown my work at an art fair again since.

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At the time, I remember being confused. I thought what I had made what people wanted.

In other words - I had made the art for the buyer.

Now, why did I do that?

Well, in the past, buyers had bought art of mine that was similar. Similar subject matter, or colours. Similar themes.

But, this time, it didn’t work.

It’s taken me some time to figure out why that is.

Then, recently, I was having a conversation with a friend - or maybe I was reading a book on the topic - I don’t remember exactly.

And, the fundamental lesson was - when you make art for anyone buy yourself, it doesn’t work. It won’t sell. It doesn’t have the same value to others.

And, the reason is - is that you - the artist - are not in it.

In other words - if you are making art for someone else then the art is about them - not you.

And people are not buying art about themselves. They could just make that, if they were so inclined. But, more importantly, they already know their own stories, their own habits - their own quirks.

But, they don’t know yours. And they want to know yours. And, they will pay for it.

Meaning, the art can’t be about anyone else but you, if you want it to mean anything else to anyone - and, if you want to sell it.

I think this is counterintuitive. It certainly was (and is) for me.

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Rejection is a bitch. And, I know the it isn’t personal. And, I am not looking for sympathy.

But, it still stings.

Fast forward to early Thursday morning of this week. Maybe around 7 am. I was making my coffee. And, checking my email to see if something I had been waiting - something which was, in fact, overdue, had come in.

It had.

It was an email from the organizers of a conference that I had applied to speak at.

And, they had rejected my proposal.

The topic of my talk, the format, whatever - it’s all kinda irrelevant.

But, I thought it was good. Good enough to get in anyhow.

One thing that has really struck me since leaving law and focusing on coaching, speaking and facilitation is how much more often my proposals - my offer - is rejected.

I think this is one reason why rejection is so much rarer in the legal profession. The work has, actually, nothing to do you with you as a lawyer on a “soul” level. Rather, people drop off their problems, you put it into you little black box, and spit out a solution for the client.

And that solution is often best if it has nothing of you - your actual personality - in it.

Now, that’s not to say you don’t use your personality in the making of legal solutions. Of course you do (in fact, I would say that good lawyers are very good at making use of their personalities to be effective counsel and advisors).

But, at the end of the day, the solution itself is very much devoid of any emotion, personality or soul at all.

It is just a document, or a ruling, or a “fix”. It doesn’t care about the who very much at all. And, that’s by design.

But this isn’t law anymore.

Standing there at the counter, coffee now less hot than I would really prefer it was, I read the email again. And again. And again.

And, I immediately went back to the art fair. And I thought about the high ceilings and the really bright fluorescent lighting and standing in that booth showing photos that I liked but didn’t love.

And, I realized I’d done it again. Built something for someone else. Crafted something that was good - but still didn’t have enough of me in it. And then been surprised when it got turned down.

Thoughts? Leave a comment, share this with someone you know, or send me a note here.

→ Let me know which topics, challenges or thinkers I should write about next.

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→ Stop by my website for more info on what I do and how to work together.

I have always loved magic.

I spent countless weekends as a kid at a place called “Browser’s Den of Magic”. It was a magic shop - but also a hang out - for kids and mostly older men who needed a place to hone their craft, talk shop, and maybe, escape their houses.

The place was run by an older fellow - Len Cooper.

Len would sit there, with his cigar, and do tricks. No matter which trick you asked to see, he’d perform it, make you wonder, and then put it away.

It was a good sales tactic. I bought a lot of tricks.

The tricks I was most interested in were those that you don’t want to figure it out. The kind where the whole point is to surrender to the impossibility of what you’re seeing.

Sometime around 2015, I stumbled onto a show called “Fool Us” on YouTube.

The famed magicians, Penn and Teller, effectively invite other magicians onto their stage at the Rio in Las Vegas to show their best stuff and try to fool Penn and Teller, who have an encyclopaedic knowledge of magic and illusion..

And so, most don’t fool them.

In the second season of the show, I caught a video of an act by a man named Jared Kopf.

Somewhere in the middle of his act, he mentioned that his mother had been disappointed when he went to law school.

I laughed. And then I felt something I didn’t have a name for yet.

In 2015 I was practicing law. I was about 4 years into building my practice and my firm. I was doing fairly well for that stage of the game. I was my own boss, had a good list of clients, was breaking into the film and television business in a meaningful way.

And yet.

There was something about watching Jared Kopf perform that I couldn’t quite shake. It wasn’t the magic exactly - although he really was so good. It was something in how he moved. How he talked about what he did. The complete absence of ambivalence.

He wasn’t performing a role. He was being one.

And, so, I did what I usually did when I watched someone do and be something that I was so envious of - I went back to work.

That’s what we do, isn’t it?

We feel something inconvenient, and we file it. We tell ourselves it’s not practical, or not realistic, or not the right time. We tell ourselves we’ll come back to it.

Sometimes we do. And, sometimes - most of the time, I think - we don’t.

Anyway - time progressed and the years between 2015 and today filled up. Work. Marriage. Kids. A home. COVID. Stuff.

In that period, I had many other moments like the Jared Kopf one — standing in an artist’s studio watching and envying what the painter was doing and how he was living; watching people move completely carefree at Burning Man; feeling something stir at other performances and not always knowing what to do with it.

Last week, my wife and I were lucky enough to get tickets to an intimate magic performance.

Jared Kopf was performing.

I didn’t plan it that way — in fact, it was entirely coincidental.

I hadn’t thought about him in years. And then there he was, in a small room, maybe thirty people, close enough that you could see his hands.

He looked different. Long beard. Dressed like someone who had fully committed to the identity of storyteller, wizard, magician. He had aged — in the way that people age when they are doing exactly what they are supposed to be doing. Settled into himself. Comfortable in a way that has nothing to do with comfort.

And he was extraordinary.

Not just the magic — although the magic was extraordinary. It was the stories. The way he held the room. The way he talked about what he did with the kind of passion that you can’t perform and you can’t fake. He wasn’t doing a job. He wasn’t playing a role.

He had become something.

And I realized in that moment - this is the guy from 2015!

And I was having the same feeling I had felt in 2015, watching him on a screen.

But it was different this time.

It had shifted from envy into something closer to awe.

And I haven’t been able to stop thinking about it since.

Now - in 2015, the envy was sharp because I was watching someone have something I wanted and couldn’t let myself reach for. The gap between who I was and who I wanted to be was wide, and I didn’t know how to cross it.

But, this time, the gap was smaller. Not closed - I don’t think it ever fully closes. But smaller.

And that’s when I understood something about the question that had been following me around for so many years.

The question was never really “should I leave law?”

That’s the surface question. The one that feels dangerous to ask out loud because of what the answer might mean.

The real question underneath it is harder. It’s: who are you, and are you actually becoming that person?

That question doesn’t get answered by leaving. I know, because I left. The question came with me.

It gets answered by doing the work of figuring out what you actually value, what you actually want, and whether the life you’re living is moving toward that or away from it.

Sometimes that work leads you out of law. Sometimes it leads you deeper into it — but differently, on your own terms, in a way that actually fits.

Jared Kopf left law. Or maybe he never really arrived.

But what I saw in that room wasn’t a man who had escaped something.

It was a man who had become something.

That’s the whole game.

If you have thought about leaving your profession once, that’s probably just a bad week.

If you have thought about it a hundred times — if it has started to affect how you show up at work, how you are in your relationships, how you feel about yourself — that is not a bad week. That is information.

And sometimes, the information is: it’s time to go.

I want to be honest about that because most people who do what I do won’t be. They have an incentive to keep you in the chair. I don’t. If leaving is the right answer for you, it’s the right answer. Jared Kopf left. I left. Some of the people I admire most left. There is no shame in it and there is nothing to be afraid of.

But here’s what I’ve learned — from my own experience and from working with lawyers who have been sitting with this question for years:

Leaving law does not answer the question underneath the question.

It doesn’t tell you who you are when the role is gone. It doesn’t resolve the identity that got built around the work. It doesn’t clarify what you actually value or what you actually want. It doesn’t teach you how to measure your worth by something other than your output.

Those things require a different kind of work. And that work is available to you whether you stay or go.

That’s what coaching actually does. Not help you decide whether to leave — that’s your decision, and anyone who tells you otherwise is selling something. What it does is help you get clear enough on who you are and what you want that the decision — whatever it is — comes from somewhere real.

The lawyers I work with who leave law after our work together leave differently than the ones who left in a panic. And the ones who stay, stay differently too. More deliberately. More on their own terms.

The question is never really about law and it is always about you.

So here’s what I’d ask you to sit with:

Who have you felt that feeling about recently? Not the passing kind — the kind that stays. The kind that shows up more than once. The kind that has gotten heavier over the years.

What is it pointing at?

You don’t have to blow up your life to find out. But you do have to be willing to ask the question honestly.

Thoughts? Leave a comment, share this with someone you know, or send me a note here.

→ Let me know which topics, challenges or thinkers I should write about next. Reply or comment and tell me what you’d love to learn more about.

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No, not Jeopardy (although, that remains a dream of mine that I will, so help me God, accomplish one day).

It was called “Clips”.

It aired on a now-defunct station here in Canada called YTV - which was, in many ways, a low-budget Nickelodeon.

*Unfortunately - this is not the episode I was in - but I’m working on getting that.)

The show was shot in a dark studio, inside a low brick warehouse in Hamilton, Ontario (a cool city these days, but 30 years ago - not so much).

As you can see - it’s four kids standing at little boxes with buzzers, watching clips of movies, music and video games flash by on a screen.

I was good at this sort of thing. I liked Trivial Pursuit. I did well at math. I thought: this will go well.

It did not go well.

I didn’t answer one question. Not one.

I stood there in terror for the entire recording.

And when it was over, I picked up my right hand (which was sitting beside the idle buzzer) and saw a pool of sweat.

I had completely frozen in fear of getting it wrong.

And so - I did nothing.

I didn’t win the bike, or the board game, or the basketball net.

What also happened when the taping was over is that I burst into tears.

What was I so upset about?

Bearing in mind this was probably 35 years ago, it could have been any of the following:

1. I was embarrassed. Who doesn’t answer one question?

2. I lost. I had nothing to show for my efforts.

3. There was never going to be some glorious victory story of me on “Clips”. Although, in reality, this was unlikely to have happened in any case. I am fairly certain the show only had a couple of seasons.

On reflection though, I don’t really think it was either of these.

What I think it really was was that I had failed myself. I had not stepped up to what I expected of myself. I was simply sad.

And somewhere in the audience, my parents were watching. I didn’t know if they were embarrassed, or sad, or proud of me for just being there. I still don’t know. I never asked.

The kid who was good at trivia, who did well at school, who knew movies and games and books - had not shown up when it counted.

Contrast this to my brother.

He went on another classic - “Video and Arcade Top 10”.

*Not the episode my brother was in. Also working on that.

And, he won. He won the whole damn thing. He got to take home the video game for our NES (it was Kirby’s Adventure, to be clear).

Leaving aside that this is a fantastic game, what I remember most clearly is that, when he won, he was so excited that he ran off the stage and into the audience to hug my parents. They may have even had to stop taping and redo the entire winner segment.

He didn’t think twice about it. He just ran.

I’ve thought about that a lot over the years.

Not the losing - I’m over the losing (although you might not think that reading this article).

But the running. The complete absence of self-consciousness in that moment. The joy that didn’t stop to ask whether it was appropriate, or whether anyone was watching, or whether it would look ridiculous.

He was just happy. Fully, completely, embarrassingly happy.

And I remember watching him and thinking — even then, at ten years old — what is that? Where does that come from? How do you just do that?

I have no answers to that question.

Now, flash forward to 2026.

My wife and I went to see our 4.5 year old daughter in a school performance.

And, we watched her freeze on stage.

And BOOM - I was immediately taken back to that day on “Clips”.

The stillness. The eyes that go somewhere else. The body that doesn’t move while you can see that there is so much going on in her head.

And while you might think I felt embarrassed for her - I didn’t. Not entirely anyhow.

What I felt was something that’s harder to describe - a kind of ache that sits right between compassion and helplessness.

I thought I knew exactly what was happening inside her - that the person who she thought she was before she got on that stage was not the person who actually showed up when she was in the spotlight.

I wanted to go up there and stand beside her and help her. But, of course, I couldn’t.

And I found myself wondering - is this what my parents felt, watching me in that warehouse in Hamilton?

Maybe. I don’t know.

I’ll tell you what I do know though: that looking at my daughter’s face on stage that afternoon was like looking into a mirror of myself on stage 35 years ago.

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Pushing through works.

If you’ve been reading my stuff for a while, that may sound like something I wouldn’t normally say.

But, hear me out - because I’m pretty sure you know exactly what I’m talking about.

When the it was midnight but you knew you could get a few more things done on the closing agenda - you push through.

When the client is having a complete freak out and you know you can deal with it with just a few more hours - you push through.

When opposing counsel is playing games but you need to have it all wrapped before 3 pm on Christmas Eve when everyone is going to disappear for a week straight - you push through.

Pushing through is what got it done. It’s what made you indispensable. And, often times, it made you feel invincible.

It certainly did for me anyway. It’s almost - maybe even actually is - addictive.

So, I’m not going to sit here and tell you that pushing through is naive, or weak, or unintelligent or unsophisticated. Because, it’s none of those things.

It’s actually a strategy - and a remarkably effective one.

At this point, you may be wondering, “Jordan - what is it that you are doing here? What are you trying to tell me? This is not what I came here for.”

I know. And, that is why I’m not really trying to tell you anything.

Rather, I want to ask you something instead: what is it costing you while “pushing through” is working?

Because I know what it cost me.

It cost me time with my family - not quantity, but quality. I was physically present at a lot of things I wasn’t actually at. Countless meals where I was running arguments in my head. Bedtimes where I was ruminating about some argument that hadn’t yet happened - and meanwhile, I am 7 pages into the story and don’t realize how I got there. Vacations that had three people on them: my wife, me, and whoever was having that week’s crisis (and, you all know - there’s always one client who does this just that much more often).

It cost me my health. Not dramatically — no collapse, no heart attack, no obesity. Just the slow erosion of the things that filled me up. Exercise became more optional than required. Sleep was less than restful. To cite Bessel van der Kolk, the body was keeping score.

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It cost me my focus. Not on the work - I was always able to zone in as much as I needed to to get good work done. It was the focus on everything else. I had poured so much of myself into my clients’ outcomes that I was entirely preoccupied with them. Their anxiety became my anxiety. At some point I stopped being able to tell the difference between their problems and mine.

It cost me my confidence - which, I realize, sounds counterintuitive for someone who was performing at a high level. But I had made an error: I had started measuring my worth against the results I could deliver. Which is, of course, absurd. Results in law are never fully yours to control. The outcome is always, at least partly, someone else’s. But I had tied my identity to it anyway. So every less-than-ideal outcome landed like a judgment on who I was - as a lawyer and as a person.

It cost me my peace of mind. I was always thinking ahead. What’s the next response? What’s the better argument? How do I prepare for the next turn? The need to perform - to really be the best at this work - had effectively taken over the parts of my mind that were supposed to be off (or at least engaged in something more creative and, maybe, more fun). There was no off

This one is harder to say, but, many times, it cost me my decency. Some files were so combative that I had to become someone I didn’t particularly like in order to get through them. I had to steel myself, put on a kind of armour and face the war of the work. And it always worked. The deals would get done and the clients would be happy (and they’d pay well for that too). But on the drive home after work that day (or night)?I’d wonder who the hell that person was and try to turn him off at home - which, of course, was easier said than done.

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So, again - I’m not telling you that pushing through doesn’t work.

It does.

But does it have to be the price of entry?

I don’t think so any longer.

Let me leave you with one last cost. This - this is the one that took me the longest to name. It cost me the love I could have had for myself. Because I was filling a role that was, in many ways, against who I was at my core. And the longer I played it - like some super intense method actor - the harder it became to step out of the role and just be myself.

Still think it's just the price of doing business?

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When I was articling, I used to hear this story all the time: a respected, successful, highly capable partner at the firm was boarding a plane with his family to head out on winter vacation.

As the plane was disembarking from the gate and on its way to the runway, he checked his Blackberry for one last time. An email came in with a bit of a client emergency.

And, so, like any good lawyer - he told his family he needed to get back to the office, threw a tantrum until the flight attendants got the pilots to stop the plane, and then proceeded to get off the plane - himself - while his family went on to their sunny destination.

I have no idea whether this story is true. It could be myth - or, perhaps its based on a true, but different variation.

The point is - its entirely believable.

Now, yes - he could have gone back to work, got the deal done, and then taken a separate flight to meet his family later on in the trip.

Or, he could have stayed on that flight, stressed out the entire way (remember - this is before Wifi on planes), and then likely worked in his hotel room (or the business centre of the hotel) for the rest of his vacation while his family “enjoyed” it without him.

And sure - these are all problems that money can solve. I have no doubts that this partner could have afforded this vacation ten times over.

But money is not what needs to be measured here.

Instead, the question is what the true cost was to him - to his family, to his mental health, to his sense of control over his own life.

My guess is that, it was likely steep.

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I always said I’d never tell that story about my own life.

And then, I found myself having my own version of it. Before we had children, whenever my wife and I would go on a trip together, she’d always say, “Jordan, it’s great that we’re away together, but why does it always have to be three of us?”

She was, of course, referring to the client who, on each trip, decided that that was the perfect time to have a legal crisis.

Hearing this absolutely sucked. Actually, it didn’t just suck. It hurt.

It hurt that I was not present with her while we were on a trip for us. It hurt me to know that my client was also not getting what they deserved of me because I couldn’t focus at the level necessary for quality work. It hurt to know that, this would likely not be the last time this happened. And, above all, it hurt to know that I had forsaken my priorities - my values - so that I could, instead, go along with what I was told was just “the way it is”.

That was a cost that I really didn’t want to bear any longer. It simply wasn’t worth it to me.

Now, was that the client’s fault? Of course not. The client was asking me to deliver at the level of service that I always did, and expected a response (as they were right to do).

Why? Because I never set the expectation that, on vacation, I am not working.

I just simply never wanted to disappoint anyone.

And when you try to make everyone - every client - happy, you make no one happy.

Now yes, you might say - “Jordan, that’s just the deal. That’s what you signed up for when you chose to practice law.”

But, is it? Is that really what you choose when you choose this profession?

No. You don’t.

You choose the parts that reward you. That fill you up. That give you deep satisfaction - intellectually and emotionally.

But the other price of it? You and I both know - no one would choose that.

So, where does that leave you?

Well, you can stick it out. You can keep doing it the way you are doing it and, sure - you’ll get a lot of good out of it. But, given the costs, is it worth it?

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What would you tell a client who presented this set of facts?

You'd tell them to cut their losses. You'd tell them the cost-benefit analysis doesn't work.

But you won't tell yourself the same thing. Why?

On the other hand, you can choose - as difficult as it might be - to practice in a way that aligns with why you chose to be a lawyer in the first place - and, at the same time, mitigate some of the costs that, perhaps, you didn’t choose (and can no longer afford).

There’s that word again - “choose”.

The practice of law is an amazing thing - it helps clients make the best possible choices for themselves. But, in so doing, lawyers often lose the sense that they have any choice for themselves.

You already know what this is costing you. You've known for a while. The only question is how much more you're willing to pay.

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I think it was a Thursday.

It was early evening - already dark out in Toronto in December - and we were getting ready to leave the office for the winter holiday break.

I shut down my computer, walked into my partner’s office, sat down, and cried.

I’d been waiting for this to happen for years. Well, not really waiting. If anything, I’d been doing everything I could to avoid it. But I always knew it was coming.

And, so, when I sat down, and cried, I also said, “I can’t do this anymore.”

My partner didn’t say much, except, “I know.” I am not sure what else there was to say.

At the time, I was a partner in my own firm, billing solid hours, building something that we expected would last - and I was sitting across from my closest professional colleague completely falling apart. The gap between what my life looked like on paper and what it felt like in that moment was so wide that there was no way I could fake it into another year.

We had our conversation, agreed on next steps, and I drove home. I delivered the news to my wife and a couple of my best friends.

And, in that moment I knew that something that had long been ready to end had just, well, ended. I just didn’t know yet what would replace it.

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Rewind four years.

We’d just left our old firm to start our own. When we gave notice, they didn’t take it well - the partners asked us to leave immediately, waiving the (what we thought was generous ) notice we’d offered. I understood why. We were taking clients. We were competition now.

But we were doing it. Our own firm. Our names on the door (eventually once we had actual doors). More control, more money, more prestige. This was the thing you worked toward. This was supposed to be the answer.

It wasn’t.

I spent the next four years trying to figure out why it wasn’t the answer. Why more control felt like more weight. Why the prestige felt hollow. Why I was resenting my clients, my partner, my work - and if I’m being honest, my life.

So I quit.

And you know, I thought leaving law would fix it. That the problem was the profession, and if I removed the profession, I’d get myself back.

Wrong again.

There was a bottom lower than the one I’d already hit. And in the process of extricating myself from a profession that I had dedicated so much time, energy and emotion to, I managed to find it.

It was depression, yes. And loneliness. But, it was also more than that - the feeling of actually not knowing who I was without the title. I knew something like this might happen - but I really didn’t anticipate the level to which I felt completely lost, worthless and, if I’m being completely honest here, unmoored from any real meaning.

Which was strange, because on paper I had everything. Forty-something. Successful career. Amazing wife. A healthy daughter. A home. Enough financial runway to walk away and figure it out. By any external measure, I was fine.

I was not fine.

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Here’s what I know now, on the other side of it:

Quitting wasn’t the answer to the problem I actually had. The burnout, the depression, the grinding resentment - those weren’t law’s fault. They were signals I had gotten really good at ignoring, pointing to changes I didn’t have the courage to make (yet).

For me, the answer was drastic change inside the work - not escape from it. That’s my story. It isn’t (and shouldn’t be) everyone’s.

But here’s what I think is universal: this problem doesn’t respond to the tools that made you good at law. It’s not a research problem. It’s not a precedent problem. There’s no case to cite, no argument to construct that gets you out of this.

Lawyers - especially good, busy, “successful” ones - are uniquely ill-equipped for this moment. Because everything in your training says: push through, stay analytical, trust the process. Grind it out and you’ll end up where you’re supposed to be.

But what if where you’re supposed to be isn’t where you’re heading?

What if the exhaustion, the missed dinners, the drinking, the partying, the distance you feel from your kids or your wife - what if that’s not the cost of success?

I’d be lying if I said I don’t think about that evening cry-meeting every now and again. In fact, I think about it regularly.

A grown man crying in his partner’s office.

And it only happened because I was, finally, honest with myself.

That’s usually how it starts.

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I became one because a professor suggested I take the LSAT. I did well. And suddenly, the track appeared beneath my feet.

That’s how it works. You don’t decide so much as you step forward, and then momentum does the rest. Law school is expensive, it’s hard to get in, and yet — once you’re in — it’s somehow the path of least resistance. The groove is well-worn. The blinders go on. And before long, you’re not making choices anymore. You’re just moving.

I wanted to be an artist. I always wanted to be an artist. But I went for the shiny thing instead: the firm, the money, the prestige, the respect. The wife, the kids, the summer camp, the golf club. And if I’m being totally honest? I was looking for something I thought I could get from the outside. Something that — if I trace it all the way back — was really just approval.

That worked. Until it didn’t.

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I spent 12 years as an entertainment lawyer. Built a real practice. A partner, associates, an office, clients I’d known for at least a decade. By every external measure, I’d made it.

But there’s this thing I’d call “epistemological dissonance” - when you know something for a long time and can’t make yourself act on it. I knew back in law school. First month, maybe second. Standing in the foyer on the phone with my mom, thinking: this was a huge mistake. These are not my people.

I didn’t leave. I saw the shiny thing and I went for it again.

Every time I had a chance to get out, I doubled down. It’s what you do when something is uncomfortable and the alternative is terrifying. You cling harder to what you know.

The shift, when it finally came, wasn’t dramatic. It was a fight with a long-term client. Someone I’d worked with for over ten years. I was treated poorly in a way I couldn’t shrug off — and I fired them.

That was hard. It still kind of is.

But then something cracked open. Because if I could fire one client... I could fire them all. I didn’t have to keep doing this. I actually had a choice.

That realization — so obvious in retrospect, so invisible when you’re inside it — changed everything.

I left law at 40. Sat at my birthday dinner with my parents and my wife, already having made the leap, thinking: my god. I just left this stable, painful profession. What the hell am I doing?

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The career ended. But the identity didn’t. Not right away. For a long time after, when people asked what I did, I’d say: well, I used to be a lawyer. Still framing myself through something in the past. Because it was the most stable thing I could name. The most legible thing. The thing that oriented other people.

Which, when I finally looked at it clearly, had nothing to do with me. That was about their comfort.

Here’s what I’ve come to understand about identity change: it requires mourning. You have to let something die before the new thing can begin. And the old identity — the career, the title, the version of yourself that knew exactly who it was — it doesn’t disappear. It becomes a ghost.

And a ghost deserves a little respect.

Not because it’s still running the show. But because it has wisdom. It earned things. It taught things. I would have zero credibility with the lawyers and executives I work with now if I hadn’t lived through what I lived through. The wounded healer isn’t a metaphor. It’s the whole framework.

In this conversation with , we go deep on all of it — the quarter-life crisis that preceded the midlife one, the year I actually left law to teach yoga and take pictures, what it looks like to help people get unstuck without pushing them toward any particular answer, and why leaving a profession isn’t always the solution - but staying in it unconsciously definitely isn’t either.

If you’re in the middle of something - I think you’ll find something useful here.

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But First…an Offer.

A free 45 minute coaching session.

Yes, it’s true. We’d get to know each other (if we don’t already), zone in on a specific issue that’s been coming up for you lately, and work through it so you can walk away with some tangible next steps.

Of course, you’re saying, “Jordan - there’s no such thing as a free lunch.” You’ve found me out (of course). What I’m asking for in return is simply to record it and be able to use it in my marketing to demonstrate my style of coaching and what clients and I typically cover.

Think Esther Perel’s couples’ therapy podcast, but for career and business coaching.

If you’re interested, you can book a time right here - but act fast, as I only have five slots.

And now, onto today’s story.

The Dilemma

By the standard metrics of the business, Jim had arrived.

He held a partnership at a firm whose name carried real weight in the elevators of the downtown towers.

He represented clients whose problems were as sophisticated as their portfolios.

On paper, his life was impeccably balanced.

In practice, however, the narrative was beginning to fray.

Jim felt that he was unable to keep up with his family demands.

He was convinced that his clients were not getting his best.

He was sure that his firm partners were looking for ways to get rid of him.

He was constantly checking his emails to see if something - anything - had arrived in his inbox.

And, no matter what he did (or tried to do) for his firm, his family, or himself, he was sure it wasn’t satisfactory. That the correct amount of effort or results was still unattainable.

Jim was in a constant state of what I’ll call “not enough-ness”.

So, he kept trying to catch up. Sort of like this:

The “Carrot-on-a-Stick”

Many of us are familiar with the 'carrot on a stick,' though we rarely consider the cruelty of its origins.

The phrase traces back to mid-nineteenth-century “Donkey Races,” where a jockey would dangle a carrot (or other root vegetable) just beyond the animal’s reach.

The donkey, obviously unaware of the mechanics at play, would accelerate in a sad and futile pursuit of a prize that moved in perfect lockstep with its own effort.

It was a brilliant hack for the jockey - but a psychological dead-end for the donkey.

Turning back to Jim - “Success” was the carrot. His brain was the “jockey”. And “Jim” was the donkey.

By all measures, he should be winning, right?

But, he was losing.

What gives?

The Breakdown

Let’s break it down. The carrot is clearly a positive incentive. It’s the reward we work towards. In Jim’s case it was prestige, income, comfort, the love of his family, the health of his children, and a whole bunch of other things. Nothing inherently wrong with that.

The issue arises when we see that the positive incentive itself is self-moving. Imagine you are trying to shoot a goal in hockey, and the goal posts move right before you take your shot - every time. So, you pick up your pace - you line up for the shot faster, take the shot harder and - you miss again. The goalposts are always just a beat ahead of you.

Keep this up, and you’re going to get pretty tired, pretty quickly.

Jim’s professional life had become a series of moving goalposts.

In the language of psychology, this is the “Hedonic Treadmill”: the exhausting phenomenon where one’s expectations rise in connection with one’s achievements, leaving the level of satisfaction perpetually “meh”.

Jim wasn't just tired; he was suffering from the 'not-enoughness' that no amount of billable hours could cure.

But, of course, that made sense - his work was hard (it certainly wasn’t supposed to be easy), and besides - everyone of his partners and colleagues was basically in the same state. Wasn’t this normal? Shouldn’t he just accept this is what it’s like and move forward?

Maybe. But this plays into a different sort of trap.

The Weight of “Should”

Jim was playing to his “shoulds” rather than his strengths.

He “should” have been working inordinately long hours.

He “should” be constantly aware of the next impending client emergency.

He “should” have been constantly exhausted by his children.

All because, of course, that’s how it’s supposed to be in this work. You can’t get the “carrots” without following the rules.

Or, in other words, his “carrots” were attainable by a following a roadmap based on external motivators.

But, what if he turned towards his internal motivations? Would that change the map at all?

For instance, if he was really into the act of the chase itself - and less so the stick - would it be easier to stay motivated? To find inner resource that was less about pursuing a goal that always seemed to be out of reach?

Well, that’s what happened.

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The Turn

Jim started to pay more attention to what was fulfilling in his work and not the results of his work.

Jim zoned in on what he really valued about legal work - being of service; creative solution design; solving puzzles.

And as he focused in on what really mattered, he started to change how he approached his work.

When he paid attention to what he enjoyed about it, and why he was doing it in the first place, it became more rewarding. He started saying “no” to the tasks that he was able to turn down, and more importantly, weren’t aligned with what he was really after in his work.

Now, it’s not like, overnight, Jim’s stress, pressure to earn, or sense of needing to put out fires magically disappeared. That would be a crazy expectation and a completely unrealistic outcome.

But, as he adjusted where his focus was landing, the things that had historically been the “carrots” began to matter less.

As a result, Jim started to realize that he didn’t need to work so hard to obtain the rewards offered by his intrinsic motivators - service, creativity and problem solving.

The Outcomes

In fact, he found that the less effortful his work was, the better he was at it.

His clients were happier with his work because he was under less pressure to be perfect and, thus, was freer to come up with more innovative solutions.

His family was happier because he had more energy for them when he was at home and wasn’t as distracted when he was with them.

His partners were happier with him because, for starters he wasn’t as miserable or as resentful of legal practice, and perhaps more importantly to the firm-wide objectives, his newfound approach to work was actually generating more revenue - not less.

Jim had also discovered something else - that by pursuing his old “carrots”, he was also punishing himself with a self-created “stick” - exhaustion, self-flagellation and contempt.

Did this take time? Yes.

Did Jim arrive at some place where things were perfect? No.

But, did Jim need to quit his career? Nope.

Jim is still a lawyer.

He still bills hours, still navigates the egos of his partners, and still faces the occasional weekend emergency.

But the stick has been dismantled.

He has discovered that when the carrot is no longer the objective, the race begins to look remarkably like an easy walk.

He is no longer running to stand still; he is simply walking toward a version of himself that was there all along.

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During Law School, I did an exchange program at the Faculty of Law at Hong Kong University. And by “program”, I mean, I mostly travelled to other places in Asia when I was supposed to be in class (Note: I wasn’t the only one who did this. Actually, I am fairly certain everyone did this. But, I digress).

One of the places I visited was Thailand. And while I was there, exploring countless wats, monasteries and other spiritual attractions, I went to see a fortune teller.

It was a combination of palm reading and numerology. I won’t bore you with what the fortune teller told me. But, I do have the original, handwritten notes he made that day, and, I have looked at them many times over the 20 or so years since that reading.

And, much like the day I received his predictions, each time I read them, I am reminded that I didn’t go to see him because I believed in fortune tellers, or palmistry, or numerology.

I went because I didn’t want to decide.

What I was hoping for was the ability to know something that, by all rights, I shouldn’t. To have certainty about the future. To effectively guarantee that, no matter what questions I had about what to do next, my decision didn’t really matter because - it was written in the stars. Or on my hand. Or in the crystal ball.

I didn’t need to make any decision at all because the decision had already been made for me.

Now, I’m not saying that I don’t believe in anything beyond us. And, sure - some people may have a gift or intuition that lets them connect to something greater than us.

But - and this is an important but - relying on a fortune teller to give us an answer - any answer - can likely be chalked up to a) something that is unanswerable or b) making a decision to not do the work that has to be done to get the answer you are seeking.

It’s a shortcut. A mirage.

No, not the Mitsubishi vehicle.

I am talking about the appearance of water on the horizon in the desert.

A mirage is an optical illusion that forms from two different air densities refracting light in different ways. Due to the disproportionate temperature difference between the ground and the atmosphere above, you’re most likely to see a mirage over scorching surfaces, like desert sand, a highway, or a sidewalk.

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Mirages are dangerous - if you see something that looks like a pool of water in the desert, and you just happen to be dying of thirst, well, you are going to go towards that mirage and end up not only disappointed, but probably, even thirstier (or dead-er).

Case in point - Bugs Bunny in “Sahara Hare”:

Mirages are dangerous not for what they are, but for what they are not. Which is to say - real.

Like (most) fortunes told.

And, like many shortcuts.

Over the past year or so, I’ve met lots of folks who are looking for shortcuts. And those shortcuts, rarely if ever, work out.

And, its important to say outright - sometimes, coaching doesn’t fail because it doesn’t work.

It fails because it’s being used as a delay tactic. There are two primary cases where this happens:

They Want a Fortune Teller

Sometimes, they come to me for answers. Answers which, they almost certainly already know, I can’t actually give them. For starters, I probably don’t know the answer - and, even if I did - would it actually be in their best interests to just give it to them?

And, so, we’ll have the introductory call, we’ll make a plan, I’ll explain my fee structure and how my programs work.

And then, it’s time to book the first session.

But, the client is nowhere to be found.

I simply acknowledge that absent some life changing circumstance that precludes them from going forward, they aren’t ready to work hard enough to get the answer they are looking for.

They Have a Crystal Ball, but Don’t Like What it’s Telling Them

At other times, we’ll already be working together. But, there is just one thing that keeps coming back up - and the person I’m working with simply won’t use their best effort to address it - to take the steps that they are being called to do in our work together - in order to obtain the benefit and make the change that they not only want, but know, they will have if they just “do the thing”.

And, so, we talk about it again. And again. And again.

In both cases, the move is the same: letting someone else hold the question so I don’t have to answer it.

Now, let me be clear: both situations are OK. They are totally OK.

I attribute no blame to the people who find themselves in one of these patterns. I know how difficult and how costly (both time- and resource-wise) it can be to change and to take on the work required to effect lasting, meaningful development.

The truth is - it’s really hard for me to do this kind of work well with people who don’t want to work hard at it. Nothing in life worth having is easy, and if you are looking for an answer that has been eluding you for some time, well - it’s likely going to take some hard, uncomfortable and potentially long-term work.

So, what’s my point here?

Whether you are working with or want to work with a coach, therapist or any other person who is ostensibly going to help you navigate a change that you want to make in your work, life, or being, ask yourself: “What decision are you hoping someone else will make for you?”

Sometimes coaching, like fortune telling, becomes a way to delay choosing - dressed up as wisdom. Most of us already know the answer. The real question is whether we’re ready to live with it.

Have something to say? Send me a note here.

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A baby elephant arrives at the circus.

A collar is placed around its neck. The collar is attached to a rope which itself is attached to a heavy, metal stake hammered into the ground in the centre of the ring.

The elephant, young, weak, and unable to break the rope or pull the stake out of the ground, concedes to walking in circles around the stake, day in and day out.

The elephant grows. And grows. And grows.

Eventually, the elephant becomes strong - able to crush a car with one foot, or knock down the wall of a house with one nudge.

Despite this strength - and the fact that, at any time, it could snap the rope or pull up the stake - the elephant continues to walk in circles.

The elephant, in the face of all evidence to the contrary, still believes that the rope can hold it back - and, so, it never tries to break free.

I love this story. It says a lot. About elephants. But, maybe more so, about us, and how no matter how much we “know”, we can still carry beliefs that hold us back from the things that we can, in fact, do and accomplish.

I will confess - I fell into this trap in my own career. I’m not bragging, but - I was an excellent lawyer. The best? I don’t know - I doubt it. But I was good at what I did.

I didn’t really love it though.

And, like a marriage that is amazing on paper, but is “meh” in your heart, that can be really dangerous. (For the record, my marriage is wonderful - but I digress).

Like many others I’ve met over the years, I also believed that not only was being “good” a reason on its own to stick with it, but also, because, being “good” made it all the less worthwhile to do something else.

Being “good” was the rope - the thing that I believed, wrongly, was holding me back from taking a chance and doing something different.

And, when you’re good at something - when you know how to navigate the challenges, anticipate the pitfalls and accomplish really hard things in the work that you are called to do as a part of that job - you get really good at muscling through the miserable parts. Or, in other words, you start to forget that there is a rope.

Research actually shows that high performers suffer long because they can tolerate more. People selected for leadership (“high performers” in their own right) tend to display higher stress tolerance even before assuming the role. But, crucially, they also experience significant stress because of the demands and constant threats inherent to those positions - and through which they need to push through.1

So, why do people stick with it then? Even when they are good at something that they might absolutely hate doing - even when they know that, in the short or long term, sticking with it is ultimately not good for them - why do they push through?

A few reasons to consider:

• Praise. Yes, no matter how much we might dislike our work, it still feels good to be praised for doing a good job.

• Promotions. Not only does progress = praise. But, as we move “up” in our world of work, we can very easily come to believe - when I get “there”, it will be better - so, no reason to change it up now.

• Respect. If we are doing something we are good at, we are respected by others (or, respect ourselves) for our skill - in spite of (or perhaps, because of) the fact that we are suffering doing it.

• The Sunken Cost Fallacy. “I’ve already put so much time, energy, effort, reputation and life into this that I’ll never be able to make that up elsewhere,” or, more commonly, “It’s too late to start again.” Need I say more?

• Golden Handcuffs. Disguised as professional validation, on the surface this is the sense that it’s worth it on a monetary basis to stay where we are - to be a “bird in the gilded cage” if you will. You’d be dumb to leave something so well paying, even with the misery that entails. Under the surface, the “handcuffs” are really psychological - escaping from their grip entails losing more than money. The identity and prestige that can be tied up (no pun intended) in the “golden handcuffs” is a loss many are not willing to endure.

• Identity scaffolding. The psychological structure that forms around your work (and not just from it), it’s everything your job subtly holds up so you can avoid asking the harder questions. Questions about your social legibility, or your worth, or the coherence of your own personal narrative. Even questions about the future. Questions that, without asking, often lead to, “I don’t even know who I’d be without this job.”

  ---

Let me be clear - none of these reasons are bad or wrong. In fact, they are all perfectly fair, understandable, even logical reasons to stay where you might be. And, I should add - it’s entirely unfair to judge someone for their reasons, whatever they might be, to not make a major (or even minor) career shift.

But - even with the fairness of reasons - it’s hard to deny there is still a cost to staying good.

For starters, when you are good at something, it gets really easy to stop asking if you like it. You start to replace your desire for a task with your own excellence at that tadsk.

Like being in a really hot sauna. Yes, I am good at being in a sauna for a long time. Is it enjoyable at minute 23? No. Am I considering how much I am enjoying it in that moment? No. I am just focused on getting to the next minute. (I realize now that I’ve written this out how insane this might sound).

That’s not to say that there isn’t enjoyment out of doing really hard things. I am sure many of you have felt the satisfaction of having closed out the worst, most painful deal closing that you truly thought would never end.

It’s just that - your career is not a sauna session. Or a marathon. Or a boxing match. Or even a deal closing.

All of those things are short-term and you can almost always see the end of those from where you are (regardless of whether you are enjoying them or not).

But, a career? Not as easy. Especially one that consumes your identity.

Really, this is all a long winded way of saying that, when we are good at something that we don’t really enjoy any longer, we start to think, “If I’m this good at it, I should enjoy it.”

And what do you lose when you start saying that?

You lose curiosity - you are bored with what used to interest you, and you start to convince yourself you are burned out (instead of just getting curious about something else).

You lose appreciation for your work - you resent the role while you convince yourself it’s your duty to be doing it (instead of admitting that you owe yourself a duty to find something you do appreciate).

You lose your sense of real stability - trading in the low risk of a plateau for the balance you would likely feel if you were experimenting with something truer to you.

And, perhaps above all, you deny yourself the pride of pursuing the thing that means most to you, not on paper, or reputation-ally, but in your bones.

The upside of all of this is that, when you realize the costs, you can start to actually do something about it.

I know I did. And, it entailed the following (in order):

[Note: Interestingly, the research confirms that this is actually a normal sequence of events for those of us who go through major career or role changes (despite it feeling completely abnormal). So, if you are contemplating something similar, get ready.]

Ego Withdrawal. This happens when the external mirrors that used to confirm who you are go quiet. For me, this is when I check my emails and realize, “Oh, no one is hounding me for anything right now.” Less urgency. No one needs me in the same way. This can also often be experienced as a strange flatness or a loss of edge. This is when the things that reinforced your identity go missing - and you don’t know what to do with that. This identity discontinuity is often associated with challenges in life satisfaction and adjustment, indicating real internal work during transitions.2

Panic. Then comes the “Oh, shit” moment. The moment you think, “Uh oh. I made a HUGE mistake.” This makes sense. You just jumped out of a plane, but the parachute hasn’t opened … yet. So, you go through all the usual thoughts of, “I can go back, right?” and, “What is wrong with me?” and of course, the best, “Man, life was perfect, so why did I do this?”

What’s actually happening is this:

• Your nervous system has lost its predictive model

• Your brain is scanning for certainty

• Old identities start yelling because they know how to survive

You are fundamentally having a threat response. And, so, if you treat this as panic time, then you look for safety. You go back. And, a lot of people do this. And that’s OK.

But, if you try to navigate this through intuition, the parachute opens. There is a chance to slow down and find direction.

If we think about this as a “liminal” phase, the research frames these types of transitional periods as moments of suspended coherence, where individuals are neither fully in their old life nor fully into a new one - an experience marked by disorientation and, of course, panic.3

Space. If and when you do slow down, something weird happens. And, I think, this is the most under-appreciated part - you get some space.

To be clear - this is not peace. You will be bored. You will go on really long walks. You will have meandering thoughts. There will be emotions that arise, and you wonder, “Where the f*ck is that coming from, and why?”

But, you’ll have the room for all of it. And, that’s a good thing.

This is also the time where you might allow some grief to surface over lost opportunities or projects or ideas. Curiosity will start to re-emerge. Things you ignored now get the attention they likely originally deserved.

For those of us who are high performers, this phase is really hard because, by external standards, it is really quiet. It is “unproductive”. And that is hard when you have spent so long being über-productive.

And, so, most people try to rush this part for, if no other reason, to feel like they are doing something.

That’s a mistake. Probably a necessary one, but a mistake nonetheless.

Work-related identity loss and career transitions often involve a period of ‘identity sense-making’ where individuals experience confusion and emotional difficulty as they reconcile their past identity with emerging possibilities. So, like a fine wine, you have to give it the time it needs to breathe - otherwise, it will just take like alcoholic grape juice (read: not good).4

Rediscovery. This part isn’t reinvention. It’s remembering.

For me, this was recalling things that I used to enjoy (including as a kid). The values that I used to hold highest before they got sidelined for other stuff. The questions I used to ask but lost the time for. Even memories that resurface after so many years of staying dormant.

At this point, people often say:

• “I haven’t thought about this part of myself in years.”

• “I used to love this.”

• “This feels… familiar.”

It’s sort of like looking at the rings of a tree - where you can see the rings closer to the core and remember, “Oh, yeah, that was the year of the drought.” Or, “Yes, that’s the year that we carved our initials into it.” You see the evidence of what was around before you got to where you are.

That’s important information. So don’t disregard it.

But, also, don’t think this is you going back to your glory days in high-school,. Because, you aren’t. This isn’t regression.

I think a lot of folks think that, when you get to this phase, you are just becoming more immature - and instead of you re-discovering aspects of yourself, you are really having a midlife crisis, subsequent to which, you’ll leave your partner and children, go to Burning Man, discover house music and MDMA, and then come back and live as a mediocre, has-been professional who moonlights as a DJ.

Not that there is anything inherently wrong with that.

But, that’s not the point. The point is that this mistakes regression for integration of earlier self-states that never really got to be expressed. This phase is not getting about smaller - it’s actually about getting bigger.

Integration. This is where it all comes together - literally. Where you stop needing to look elsewhere - money, prestige, title, etc., to confirm your identity. In other words, the work reflects you - and not the other way around.

Sounds nice, right? So, what’s changed?

• Decisions feel slower but cleaner

• Status matters less, meaning matters more

• You can tolerate ambiguity

• You bring worth to the role.

Is this a quick process? God, no.

Will it feel like you are going in circles? Probably. It takes a long time to realize that the rope isn’t really strong enough to hold you back from getting through this. It may take a few efforts.

But, is it worth it? Absolutely. Because, there is nothing more expensive than being exceptional at the wrong thing.

But, when you are exceptional at the right thing? Well, you tell me.

Have something to say? Send me a note here.

→ Let me know which topics, challenges or thinkers I should write about next. Reply or comment and tell me what you’d love to learn more about.

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The Panic

It’s the end of the first month of law school.

And I am standing in the atrium on the phone with my mother telling her that this was all a huge mistake.

I really should have gone to art school after completing my undergrad.

These law school people are not my people, the work is ridiculous, its way too competitive, and above all, its really not what I expected at all. In a bad way.

And, then, I didn’t leave law school. I stayed. I finished.

I don’t know why I stayed. Maybe it was the sunken cost of tuition. Or, that I had made a couple of new friends already and didn’t want to abandon them. Or maybe it was the other sunken cost of having done the LSAT applied to the school, been accepted, and then put in a month of orientation, work, readings, textbook acquisitions, and so forth.

Maybe it was that I had convinced myself: “This is how it is supposed to be.” If everyone around me was miserable, sleep-deprived and desperate to land higher on the curve than the others, then of course I should feel the same way.

The Myth of “It’ll All Be Worth It Later”

And, really, what did that matter? Eventually, I would be so successful (or, make so much money; or, be so respected; or, have enough prestige; or, whatever) that I could put my misery and dislike for what I was doing aside just long and far enough that I could stick it out, and maybe - just maybe - enjoy it.

Or, more likely - maybe it was that I didn’t want to disappoint anyone. My parents. My friends. All those people who I thought had so much riding on me.

They didn’t, by the way. That’s not to say they didn’t care, but, they certainly cared less about what I was doing, and more about how I was doing.

But, it took me years to realize that. Well past the point where I graduated from law school, highly uncertain that I had made the right choice, but very certain that I was going to have my high-paying job on Bay Street, make partner somewhere fancy, and be set (and happy) forever.

I return to that memory in the atrium regularly. More in the past few years. Actually, I kind of forgot about it until about 3 years ago. And then - bang. That memory shows up in a conversation with a therapist or friend or client (I don’t recall which, but I do remember it showing up suddenly).

The Choose-Your-Own-Adventure Fallacy

What was that? Was that the part in the “Choose Your Own Adventure” of my life where I made the wrong choice? Was there even a “wrong” choice? Those of us who grew up with these books (Note: I recently discovered they still publish these, albeit, with better artwork) know that, it doesn’t really matter which choice you make - the book ends. It all works out. Could it work out “better”? Sure, maybe. You escape the planet you are stranded on instead of making a life on that planet with your newfound alien compatriots. In both cases, it “works out”.

Maybe then I am asking the wrong question. Maybe - the question is really, “How would have things worked out if I had chosen differently?”

One way to think about this (H/T to Tim Urban and his amazing blog “Wait But Why?”) is to consider the following diagram:

At any point in time, you literally have infinite directions you could go in. Which means - of course - in the past, you also had infinite directions to go in. You had, as Urban describes, “open” paths.

The problem (or upside) is that, once you are on your life path, the alternative paths immediately close. They disappear. They are gone. YOU CAN NOT GO BACK AND CHOOSE A DIFFERENT PATH despite the fact that yes, at this moment, looking backward, you still have an infinite number of potential future paths.

Because we see choice ahead of us, we think (falsely) that we have choice behind us. There must be some psychological or evolutionary reason for this. I don’t know. And, I don’t need to know.

All I know is that, when I apply my “future thinking mind mode” to the past, I waste energy and time. In that “mode”, I live in this weird, worrying, wondering, regretful, rueful state where a) I don’t really move forward on any of the potential future paths and b) I tell myself stories that are really just corrective past life fantasies.

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And, what’s interesting is that, I used to think I was the only person who did this.

But, I see now - I am not. I have spoken to so many people lately who wonder, “What if?” About all sorts of things. Yes, mostly career, but honestly - about life partners, about trips they took, about what they studied in school. Even about other things that they literally never had any control over - where they were born, who their parents were, or, whether they were born “naturally” or by c-section.

The Only Question That Matters: “Is This Good Enough Today?”

Well, looking back on my own law school/MFA dilemma, I ask, “Do I actually regret anything I did? Do I regret my choice?”

And, the answer is, “No.” Sure, things might have worked out differently, but that is largely irrelevant.

Going back to Urban’s diagram - all I can do is look at that point on which my path coincides with “Today” line, and ask myself, “Is this good enough?” If so, then it doesn’t really matter which potential paths formed the actual path to date, because, they all worked out to something that, today, is good enough. In fact, it’s probably a lot better than “good enough”.

Letting Go

So, here’s the ask: if you’re ruing the day you went to law school, or took the LSAT, or went to medical school, or dropped out of school entirely. Or, you are regretting the day you proposed to your husband, or the girlfriend you broke up with in high school who may have been the “one”. Or, you are simply wondering how your night would have been had you ordered something else for dinner.

Ask yourself: would I be here, right now, had I not made that choice? And, from this vantage point, if I really let go of the past possible paths, what opens up for me today?

Let me know what you come up with, of if you think this is just nuts. I could go either way. Send me a note here.

→ Let me know which topics, challenges or thinkers I should write about next - Reply or comment and tell me what you’d love to learn more about.

→ Connect with me on LinkedIn - I share more thoughts like these there.Let me know what you come up with. Or if you think this is nuts. I could go either way.

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And with the new year, of course, come resolutions.

I never really did the whole “new year’s resolution” thing.

I always figured - if there is anything I really care about doing, either: a) I don’t need a new year to commit to it - I’ll start it when the idea arises; b) I am already doing it and don’t really need to resolve to do it at all; and/or c) it’s not important enough to resolve to do on the impetus of a new year, so, when the schedule permits, then I will start making a new habit of this thing I am apparently going to resolve to do.

So it’s interesting to me that I am writing an article about new year’s resolutions at all.

And, that I actually have one this year.

The word “resolution” is built from two primary Latin components:

• re-: A prefix meaning “back” or “again.”

• solvere: A verb meaning “to loosen,” “to untie,” or “to release.”

In its original Latin context, resolutio referred to the process of reducing things to their simpler forms or “unbinding” a knot.

But, in today’s day and age, and especially around this time of year, it is almost inversely defined as, “to get more done.”

And, while this has nothing to do with the etymology of the word, and everything to do with something I have more or less been avoiding forever, I am going to aim to resolve to do less this year.

And, I don’t mean “do less” as in “be bored like these influencers in order to inspire creativity, but also (and perhaps moreso) to attract more followers and, thus, do more.”

I mean something more like the definition of “resolution” - to loosen my grip, as it were. I’ve started to wonder whether the problem isn’t that I do too much - but that I try too hard while doing it.

But, how does one make that distinction a reality?

How can one achieve the goal of doing less without, actually, doing more? Isn’t there some sort of action, or set of instructions, or self-improvement book that I could read which will help me do less?

Probably. Yes. Here is one.

In what will surprise no one, there is an entire industry that, unironically, gets you to work very hard at trying less.

Which is why it’s so frustrating to have been on the receiving end of this advice for so many years. And, I get it. I do seem to always be doing something - or at least planning on doing something, or striving to get something done.

And, I think that last part is really the rub. The striving. The need to feel as though I have accomplished something and the only way to do that is to exert more, not less, effort. Measuring my effort in terms of inputs, not outputs.

So, perhaps this has nothing to do with doing less at all - but rather, trying less. Putting in less input, and still aiming for the same, if not more, output. Loosening the hold on what is going in and trusting that what will come out will still be good.

Thought about it this way, the resolution changes: Keep up my level of activity, but in a way that is less draining on my psychic energy, less dependent on trying, less reliant on adding energy into a system that is already overloaded.

When we add energy to a full system, the energy has nowhere to go. And, so, it’s wasted. And, so, I (or we) get tired.

It’s exhausting not because the work is hard, but because, the excess energy we’re putting in is being reallocated to supervision. More specifically, the constant supervision of ourselves while doing whatever it is we’re doing. To make sure we’re optimizing energy. To confirm we’re on track. To be certain that we are aligned with what we think we’re supposed to be doing.

Or, maybe the exhaustion comes from trying to earn our right to be here through effort. Maybe as Oliver Burkeman has said, the problem isn’t that we don’t have enough time. It’s that we try to use time to justify our existence.

Does this sound familiar? It’s funny to say (or at least, write) this out loud. Because, I have been told that this is fundamentally what I help people do in our work together: Try less but somehow get more done.

Even though I still really have no idea how to do less. Maybe I’m not even built to do less. But, I certainly know I can try less.

It’s not like there is some taskmaster sitting beside me telling me, “Jordan, do more. It’s 2026, you are 43 years old, you still haven’t accomplished half of what you want to, and yet, you are writing a Substack. Have you lost your mind?”

I hope not. And yet, I might have when I remember again that no one is actually forcing me to push this hard.

This is where the words of Byung-Chul Han come to mind: we are no longer oppressed by external forces but by internalized pressure to optimize ourselves.

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Well, that’s great.

But, that still hasn’t answered the question of “How?” that I left hanging above. But, now that we have a new definition of what it means to “do less” (read: “try less”), answering the “How” of it all seems, well simpler.

Step 1: Don’t try to answer the “How” at all.

That’s it. That’s the system.

This doesn’t mean ignore the question. It also doesn’t mean to become a nihilist.

It simply means that there is a way to mitigate, or possibly even eliminate, the exhaustion of constant self management. Less monitoring, self-optimization, performance, narration of productivity.

It means when confronted with the next challenge, question, dilemma, or existential frustration - simply don’t worry about how to change it. Roll with it. Let it unfurl on its own.

You don’t need to add energy to the wheel that is already turning.

Is this difficult? Yes.

Am I “trying” to finish writing this article? Yes.

Is that changing anything? Not really.

And, it’s not that the article will finish itself….

It’s that the harder I push, the worse the writing gets. Put differently, in the words of Lao Tzu, “effortless action” - acting in accordance with the grain of things - might get you even greater outcomes than you might otherwise have expected.

So, what does that mean for you?

Here’s an invitation - pick one thing you can simply let happen in the next month or two. And when the itch to grab back onto the steering wheel creeps up - try to re-commit to not holding on.

Have something to say? Send me a note here.

→ Let me know which topics, challenges or thinkers I should write about next - Reply or comment and tell me what you’d love to learn more about.

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It’s grade 10. I am sitting in art class.

That might be an exaggeration. I am probably standing or moving around, talking loudly over others, arguing over what something means, or obsessing over a painting I am working on.

And, in the corner, at her desk, is Ms. Lottering. A somewhat frazzled, very kind and funny South African woman who used to refer to me as her “gogga” (which I later came to learn meant “bug” in Afrikaans).

Ms. Lottering was the best. She passed away in 2020. She went too early.

We kept in touch well beyond when I think most high school students keep in touch with their high school art teacher. She supported me in my photography work, and kept me up to date on what was happening in her life. Unfortunately, we lost touch.

She also questioned my decisions. To not go to art school. To go to law school. To practice law. To abandon a path that she saw me being completely right for.

I think of her often.

I think of her most often when I am considering my next move, or my next creative “thing” - what would she say?

Most likely, “Oh stop thinking about it and just do it gogga,” in her delightful accent.

Ms. Lottering (Deline to those who knew her outside of school) had an interesting life. She was married to a man named Willy. They were both artists who moved to Canada at some point in the 80s or 90s (I’m not entirely sure). They had children, both of whom I met and came to know at one point or another. I heard that she had a really cool house north of the city where every surface was painted.

She had an uncanny ability to draw things out of you. If you were stuck with a question of what colour to use in your work, or what subject matter to cover, or who to go to the prom with (I think we may have discussed this) - she knew how to help you arrive at the most truthful answer to your question.

In short, she was able to get you to let your guard down and give yourself permission to be sincere - with her and with yourself. And it turns out, we’re wired this way. We take risks - emotional or otherwise - only when we feel safe enough to do so.

In grade 11 (when I was again in her class), we had an assignment to paint a series of self-portraits over the course of the year. This was an interesting project - one that required quite a bit of vulnerability actually. I mean, trying to paint yourself - or your innermost thoughts, wishes and secrets - onto canvas at age 16 isn’t exactly a walk in the park.1

This is where Ms. Lottering’s skill really came in. She would ask questions - not about the portrait, but about you. She would challenge you to make a picture that was about something. A story we had to tell about ourselves, or a truth we had to confront, or an idea about our personalities that we wanted to dispel through our work.

She gave us the permission that, I think, we were so often looking for to be brutally, totally, and even perhaps disappointingly, honest.

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There’s a growing body of research that suggests we don’t actually change because we’re hard on ourselves - we change when we feel safe enough to be honest.

As we roll into 2026, I am prompted by a recent conversation I had with someone around allowing herself to do what she had always secretly wanted to this coming year, but was afraid she would chicken out unless she really committed.

In other words, she was being honest that she was looking for permission to do this thing. To take a risk. Or to ask for something she wanted or needed. Or simply to do the thing that she knew she could, but had been too reluctant to do.

Why is it so hard for us to give ourselves permission?

I’ve come to think it isn’t because we’re incapable of giving it - it’s because we’re conditioned not to.

It’s easy to name a million reasons not to give yourself permission. Here are just a few:

The unrelenting march of productivity. The inevitable comparisons to others. The ways we hold back as a form prioritizing the needs or feelings of others.

We rarely need permission to work harder. Or to push through. Or to take on more. Those things feel virtuous. Productive. Safe. We’re far more comfortable being driven to action than deciding on an action.

But choosing? Choosing means owning the direction - and that can feel terrifying.

And that’s why it’s just easier not to give yourself permission to do the things that you know are likely good for you but will come at some sort of cost or discomfort or even - gasp - honesty.

Of course, we don’t struggle with all kinds of permission equally.

I’d bet you don’t give yourself permission to go to the dentist - in fact, I’ll double down and bet you don’t even feel a need to permit yourself that treatment. Unless you are one, you probably have no idea how to clean your teeth properly or fill a cavity. And so, once we’re over the financial cost of it, most of us have no problem booking the appointment.

Dental problems feel technical. Skill-based. We don’t take them personally. And, so, we have no problem giving ourselves permission to hire someone else to take care of it.

But, permission to slow down?
To change your mind?
To want something that doesn’t look impressive on paper?

Those kinds of permissions don’t gain you any followers or any applauding pats on the back. They come with discomfort. With the risk of being misunderstood. With the chance that, if the performance stops, then something else, something more honest about you, might be exposed - that you are the only one who can make this happen.

And that is absolutely terrifying.

Going back to our earlier discussion. The self-portrait. For me, this is a really hard one to get done.

But does it require permission?

Yes. Absolutely.

It requires allowing (i.e. permitting) myself to feel the weirdness of sitting in front of the camera.

But, can it be forced?

Not if we want it to be an honest self-portrait. It can only be truthful if I (the only one who can make it happen) lets myself make it happen.2

Here’s another one: telling that old friend that you lost touch with years ago that you miss them.

Do you force that? Or do you give yourself permission instead to be vulnerable - to be open to the awkwardness and the feeling of rejection and do it anyway?

What about asking for help?

For many of us, this is the real test - to say to ourselves, “You need to allow that you can’t do this on your own and, yes, you can request that someone provide some assistance.”

Unlike the dentist, asking for help with this “harder stuff” feels different. This kind of permission doesn’t just say something about what we don’t know. It feels like it says something about who we are.

Why Does Any of this Matter?

Because most of us aren’t stuck due to a lack of ability or opportunity. We’re stuck because we’re waiting for permission that no one is actually withholding. We’re waiting to feel “ready,” or certain, or justified - when the truth is, growth and change rarely need anyone’s permission at all. They come when we’re willing to tolerate discomfort, uncertainty & honesty. When we’re ready and willing to play.

Maybe that’s what Ms. Lottering really gave me permission to do. To experiment without needing to justify it and try something without knowing where it would lead.

So, Ms. Lottering, wherever you are - consider this the start of a self-portrait.

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It’s been a good year. And, end of year, it’s always nice to take stock of what’s worked.

And what hasn’t.

But, today, we’re focusing on what’s worked. Here are the four most read articles of mine from 2025 (and one from 2024, for good measure) for your enjoyment.

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She did great. I can only imagine how intimidating it is to get on stage in a darkened theatre, as a 4 year old, with a massive crowd of people cheering the names of other children while you stare into the abyss looking for your own family.

And then take the microphone.

Coincidentally, I was at the annual convention for the Canadian Association of Public Speakers last weekend. Or, “CAPS” to those in the know.

Up until a few weeks ago, I had no idea what CAPS was. Or that it even existed. But, a friend of mine who was also attending said, “Jordan - you really should be at this thing.”

And, since it was in Halifax (a place to which I’d never been), I went. Note to self: Halifax in December is not the same Halifax that you see on TV.

I arrive. I am in the soaring lobby of the Westin Nova Scotian hotel. I see people wearing very colourful blazers. Lots of very loud, plastic rimmed eyeglasses. A few patterned Hawaiian shirts. Some light up shoes. And at least one absolutely over the top haircut.

It was basically Best in Show - except with only one dog (who had a rhinestoned collar and harness on, to be sure).

I look at the agenda and realize that there is a session starting in a few minutes, entitled “Permission to Be Me” with a subtitle that I don’t read.

I go into the room and sit down. It’s me and a number of women. Many women. Too many women for this to be coincidental.

They start speaking. About their challenges as speakers, as businesswomen. It was touching, and interesting. There were tears. Someone sang a song.

And then, at one point, someone says, “It’s great to have an ally here.” Ally? Who, me?

I look back at the Convention agenda, and put it together - the subtitle to this session is “Creating Sacred Space to Explore How Women Are Building Their Businesses.”

Ah. Now I get it.

So, I slowly sink into my seat further. And I listen. It was the quietest I had been all weekend.

And it opened up into a weekend that turned out to be one of the most interesting, enlightening experiences I’ve had in a long time. The people were genuinely kind and interested in why I was there. Everyone was so welcoming.

And, yes - when you go to a convention of keynote speakers, facilitators and, in many ways, performers, yes - there is a lot of talking.

Now, it’s one thing to go to a conference or convention and meet people and talk. That is, after all, the point of these things - to speak with other people.

But this one was, well, different. 300 or so professional speakers in one room gets loud. Everyone has something to say and everyone wants to talk with everyone.

It cuts the other way too - you get that many people who speak for a living into one room, over three days, and you get to see so many keynotes, workshops and lectures done really, really well.

There were times where I was watching someone give a keynote, and thinking, “Wow. How did you get so good at this?”

(Watch people like Steve Spangler and Mike Scharenbroich and tell me you aren’t blown away.)

These people are doing more than speaking - they are engaged in a well-honed craft. An art form that I really hadn’t appreciated as much as I could have until that weekend.

A speech language pathologist once told me that lawyers are professional speakers.

No, they aren’t on stages in convention centres or stadiums or high school auditoriums. They generally aren’t scripted. But they speak: giving advice; offering insight; leading others to solve their problems.

These are people who are using their voice as part of their work.

And, I guess I realize that, in many ways, we are all called on to do the same sort of thing.

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Maybe not on the same stage. Maybe not in the same manner. Or, not as loudly.

But, we use our voices - we perform - in one way or another, to create, inspire or simply do something with the time and skills we have.

The Latin vocare means “to call” or “to summon”.

Vocation and voice share the same root word.

Watching my daughter step onto that stage, I wasn’t thinking about confidence or performance or applause.

I was thinking about how early we learn what it feels like to speak when we’re not sure anyone is listening - or when we’re not even really ready to say what it is that needs to be said.

That weekend in Halifax reminded me that most of us never really stop doing that.

Different ages. Different rooms. Different stakes.

Same risk.

Vocation isn’t just what we do; it’s where we’re willing to use our voice, even - or especially - when we’re afraid to.

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And, so, with that in mind, I thought it made sense to keep this one short and sweet.

So instead of a long essay, here is what has apparently turned into a long list of 26 things I keep coming back to.

1. You don’t need a new life/job/career/marriage/house. You need a new relationship with your fear.

   
   Fundamentally, especially with people and teams I work with, this is what it all comes down to. I just finished building out a new development model I’m working with, and the ultimate threshold for resistance is fear.

   Obviously, there are going to be times when this is wrong. But, most “stuck” professionals aren’t lacking direction — they’re just afraid of following it. Have a fear for 2026? What’s that about?

2. Your internal saboteur isn’t a bad guy - although it might feel like one.

   
   It’s really just there because of that whole “fear thing” (see above). Teach it to be less afraid, and it will shut up (at least temporarily).

3. The stories we tell ourselves about risk are often more dangerous than the risks themselves.

   Your imagination is usually scarier than your reality. In other words, the only thing to fear is fear itself. Eliminate the feeling of fear, and there isn’t anything really left to dread.

4. Most people don’t fear change. They fear being seen changing.

   See Item 13 for more on this.

5. Purpose isn’t found - it’s chosen repeatedly.

   
   This one is annoying. I know. I’ve found that a trap most people fall into (myself included) is that your purpose is this thing that you find and it doesn’t change and you can basically rely on it forever to guide you.

   That’s a myth - and an unhelpful one. Not only will it change over time, but you need to keep choosing it each and every day.

6. Action is more important than thinking.

   Over-thinker? Great. Me too. This is for you.

   This is also something I mentioned to my own coach recently - that I wish I was “doing” more and thinking less. She didn’t know what I meant.

   I meant that I get caught up in planning, ideating, strategizing - but sometimes, I wish I could just skip that whole part and just “do”, regardless of the potential for failure. She reminded me - the way you get better at doing the things you’re afraid of, is to just do them, and then see how you feel after the fact. So, go out and do something.

7. The job after the job is learning who you are - again.

   This is a fun one - once you get the job or career or position you’ve been after, all of a sudden, you’re like “great, now what?” Totally normal. For the most part, people are looking for their work to fill some other hole that has to do with identity - not work, not income, not prestige.

8. Stop expecting clarity before movement; it usually shows up after.

   This one pisses people off, but it’s true. See Item 6, above.

9. Your next chapter won’t arrive until you grieve the old one.

   
   I keep going back to this, probably because I am still processing my old chapter. Do people truly get over things? I am not entirely sure. But, for the most part, it’s really impossible to move on to the next thing until you have reconciled yourself to the death of the thing behind you.

10. The biggest trap in mid-career? Mistaking competence for calling.

    You can be really good at something and it could still be wrong for you. Once you admit that, moving on from what you’re doing (which you are good at and makes you a good living and all the things) gets easier.

9. Your values are a better compass than your CV.

   This relates to Item 5 - because, yes - you can pick a purpose for the day or week or year. But, how? What is it based on? Values - the things that really matter to you, that are lasting, that are more than just temporary experiences.

10. Identity weighs a lot.

    This doesn’t mean you need to drop it. At least not entirely. But, there’s this thinking I have that, if we hold onto it too tightly, it starts to really weigh us down. The albatross, if you will. So, like sand, hold it lightly - it won’t cause as many problems.

11. Your nervous system is in charge.

    This is a difficult one - at least I think so. Despite years of yoga and all sorts of other physical/somatic trainings, and even vocal cord surgery (probably related to stress) I still find it so hard to just trust that, when my stomach is turning or my throat is clamping up, my nervous system is telling me that something is off and that - maybe - I should just take a minute, reset, and then revisit what’s happening - instead of pushing through.

12. Feedback isn’t the end.

    
    So many folks I know look at feedback as being, “Oh, shit. I guess this means my work is no good, which means I am no good, which means I better start figuring out my next thing.”

    No.

    This is a complete fallacy. All feedback is is a chance to look, get curious, and then consider, “Is there anything I would want to do differently? Why?” And, then to Item 6 above (or, to quote Nike) - just do it.

13. Try to need less approval.

    Making huge changes (or even small ones) often comes with the thought of “what will they think?” (where “they” could be anyone from your parents, to your partner, to your kids, to the broader “they” of society-at-large"). And, at the end of the day, it doesn’t really matter who the “they” is - because, you have to just not care what “they” think.

    Most people generally don’t care what you do. And, even if they did, and they disapproved - what does that change?

14. Burnout isn’t about doing too much - it’s about doing too little of what works.

    Forget everything you’ve been told about burnout.

    We get really tired when we keep expending energy on things and see no change - in outcomes or how we feel. You could do less - and things could get better (i.e. coincidence), or get worse (i.e. drift along).

    Or, you could do more and things get better - but only because you are doing what works - because you have figured out why certain things work for you and certain things don’t. In other words - you are clear on the desired future.

15. You can outgrow a life that still looks good on paper.

    A lot of things look good on paper:

    • The perfect budget.

    • Fully open concept homes.

    • Communism.

    And, like these things, life can also look good on paper. I call this “ticking off the boxes” - you’ve done everything you were supposed to do, but so what? The itch still isn’t scratched. This may be an existential condition of course, but even still - just because it looks like it’s supposed to be working, doesn’t mean it is.

16. Curiosity is the antidote to paralysis.

    
    Stuck? Look around. I mean this both literally and figuratively. Get out of your head. Look up and out. To the horizon. What do you see in your field of view? Curiosity is the basis of exploration. And what do you need to do to explore? Move.

17. Most career ruts are spiritual problems disguised as professional ones.

    
    Now this is one that I think most people want to avoid. But it’s connected to Item 22 below - when we lose hope, we stop aiming for the next chapter - the next part of life or work or relationship to unfold.

    When we have faith that whatever unfolds is what is intended (not necessarily better, but for the better) then allowing that to happen becomes something we resist that much less. This isn’t a call to go get religious or anything (though, there is nothing wrong with that).

    But, consider: what are you putting your trust in besides yourself?

18. If your life feels too small, it probably is.

    I don’t have anything to add to this.

    ---

21. You don’t need more confidence - you just need more practice.

    
    Confidence isn’t mystical; it’s just muscle memory.

    Confidence is an outcome, not a prerequisite, to taking action, to trying and failing, and to taking risks. Just like any muscle, confidence won’t grow unless you exercise it - and sometimes that’s painful.

22. Hope is a strategy.

    
    See 17 above. If you can hope again, no matter how hard that is, not only do the issues of the day seem less important, but there reappears the reason to keep trying - the knowledge that things do get better, no matter what “better” is.

23. The fastest way to feel alive is to stop outsourcing.

    Here we are again at the idea of “doing”. Bored? Don’t hire someone to mow the lawn - mow the lawn yourself. Uninspired? Don’t ask someone to take a picture for you. Take the picture yourself.

    Stuck? Don’t ask anyone else to solve the problem - do the work, and solve it yourself. You’ll see - you’ll feel much more capable pretty quickly.

24. The discomfort you’re feeling is the sign.

    Meaning: pay attention to it. What’s it saying? Can you learn from it? (The answer is, yes). Great. Now what do you do with that new knowledge? We are so conditioned to run away from discomfort that we really lose out on what it is trying to tell us - and, how much closer we can get to where we are meant to be.

25. What got you here won’t get you there.

    Literally. Or, to quote Anton Chigurh of No Country for Old Men, when finding yourself in a situation that you really don’t want to be in: “If the rule you followed brought you to this, of what use was the rule?“

26. The night is darkest before the dawn.

    Cliché, I know. But, really - when it feels shittiest, that usually means you’re on the brink of something great. So, keep going.

I’d love to know which of these hit you - and which didn’t. Send me a note here.

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Some people might say I’ve had a less-than-traditional career.

Fair enough.

On the surface, it looks pretty straightforward — I went to law school, became a lawyer, ran a practice.

But I’ve also simultaneously and sometimes concurrently done a lot of other things. Ran a film festival. Photographed professionally. Produced film. Left law. Started a coaching and advisory business.

And so, in that regard, the path itself has been anything but traditional.

Because of that, I get a lot of questions.

Earlier in my life, people asked, “How did you become an entertainment lawyer? How did you build that business and practice?” When I was more active as an artist, the question was, “How do you do that and also be a lawyer?” And once I left law, it shifted into, “How did you get out? How did you actually make that leap?”

These conversations go a lot of different ways, so I figured it might be helpful to lay out a few of the questions I get most often - and the answers I usually give.

1. “How did you do it?”

This is the first big one. And, I think, it really hides a number of other questions. But, people like nice, packaged questions to go with nice, packaged answers.

The honest answer is: I don’t really know. I’ve had a lot of help. I worked with a great therapist for a long time. I worked with coaches. And, to be blunt, I suffered a lot.

But in the suffering lies the teaching.

So much of the process was revisiting what mattered to me - again and again - and asking myself what I was actually willing to do in service of those things.

As a lawyer, building a practice, I asked, “Who do I want to work with? What types of problems are the most interesting to me? Where will I be able to, most likely, marry my interests with the profession I was trained in - and make a living doing it?”

As an artist, it was largely the same questions - “What story do I want to tell about myself and my work? What feels like an honest expression of my feelings on the world and the work I am doing?”

Even now, whether I am entertaining producing a project, developing a workshop, or assessing whether to work with a person or firm, the questions often feel the same: “Is there alignment between what matters to me and this person/team/company? Are the challenges that are presenting in this case areas of life that I am not only interested in, but also, am able to be of service to? Do I feel something when I am considering this person/project?”

Of course, the answers to these questions are not fixed - much as the questions are not fixed themselves. They changed as I grew, as my practice evolved, as life changed.

The biggest shift was, of course, when I decided to leave law. I had struggled for a long time with “being” a lawyer (I use “being” in quotes intentionally - because it’s partially a way of being, but also, a job - it just sounds weird to say I’m “doing” law. But, that is a topic for another day.) Because, at that point, what mattered for me had changed.

It didn’t feel like me - it hadn’t for a very long time. I’m not sure it ever did. And I still struggle with that question — what is really “me”? I’m not entirely sure. And, might not ever be. But, this feels like it’s getting closer.

Which brings me to the nut of this whole “How did you do it?” question - I finally began the process of letting go of the fight with myself.

2. The Practical Side: Conversations and Curiosity

On the practical front, I spoke to a lot of people. A lot of people. That’s usually the advice I give to anyone starting a legal practice (or any business, frankly): network your face off. Do it without a specific target in mind. I didn’t know what my legal career was supposed to look like. I vaguely knew I wanted to be near the arts. Entertainment law sounded like the obvious bridge. But I had zero expectation it would actually happen.

So I talked. I asked people a lot of the same questions I am highlighting in this article:

What’s it like? What do you actually do? How would I even get into this? Who else should I talk to?

Networking turned out to be a real skill for me — one I enjoy and one I teach now. And exploration became the backbone of every transition I’ve ever made. It required being open, curious, and, frankly, willing to tolerate a lot of uncertainty. That part was uncomfortable. Painful, even. But that discomfort was the price of admission.

And, it continues to be - in every facet of work that I do. Most notably, it is also the most important part of getting out - of a career, a job, a relationship. Talking about it is not enough on its own, but it leads to clarity. Be selective about the inputs, of course - we have the power to make decisions for ourselves, after all - and we are accountable only truly to a very small list of people.

But, the “What’s it like?” conversation is just as powerful for the exit as the entrance (and reminds us, like William Bridges, that changes really happen on a continuum and are not simply distinct events). It gives us the sense that, while we may not really know what it’s like until we are doing it - until we are “there” - it at least lets us prepare on some mental, emotional or psychological level - and, to strategize.

3. Leaving Law Was Scarier Than Entering It

If getting into law required courage, getting out required more. I had to trust — in the Ray Bradbury idea — that if I jumped, I’d grow wings on the way down. I didn’t fully believe that.

In fact, it took the repetition to me by a number of people I trusted that, yes - it would be OK. But, would it?

This is where I think the hardest part of the process comes in. Faith. Hope. The belief that, yes, this is really hard and you are saying goodbye to a whole “thing” that you’ve built up (and everything that comes with that), and it’s going to hurt and be a loss which, at least on some level, you will need to mourn and grieve for some as yet indeterminate period of time.

But, on the other side of that period is a time and place where things will improve and will be better than where you’re at now.

Perfect? Of course not. Guaranteed success? It would foolish to believe that.

But, different? Shifted? Perhaps, maybe, better?

Yes, absolutely. If you’re an optimist.

It’s true that your faith - your ability to hope - will continually be tested. But, learning to be an optimist - learning to trust not only in the process but also that it’s OK to hope and be disappointed - are crucial.

4. “Did you know what you wanted to do next?”

Now, it’s one thing if you know what you’re aiming for when you decide to make the switch. I think that could make it a bit easier because, if you know the destination, you can at least start to assemble a path there. It may not be the final path, or the perfect path - but the first steps are visible.

But, when you don’t know? When you really have no idea? That’s a different challenge. And one that, I am learning, is so much more common that most of us are led to believe.

When I decided to leave practice, the only things I knew were:

• I needed something more creative.

• I wanted to keep working closely with people.

• I didn’t want to live in a high-liability profession anymore.

• I needed more flexibility — more life, less being on-demand 24/7.

• I didn’t want to “sleep with my work,” which was basically how I operated as a lawyer.

There are lots of jobs that could have given me some or all of those things. Sometimes I still think about those. But this kind of coaching/consulting/advisory work ended up being the right combination of ingredients.

For now.

And, yes, that is an important one to flag.

I think many of us approach our next phase of work or career as, “Well, this time, this is going to be it. I’ve finally figured it out.”

But, did you think that when you chose the first profession?

If so, then perhaps you were wrong? And perhaps you could look at this shift as temporary as well?

Because, in all likelihood, it will be.

Accepting that actually makes it easier to make the move. If it’s not final - if it’s not the “be-all, end-all” - then it takes so much pressure off the choice - because it can be undone.

It’s one thing to consider your identity as relatively permanent. You sometimes see this with artists - at their soul level, they are artists - regardless of whether they paint or draw or make a living as artists.

But it’s another to think your work is unchanging. And I don’t mean your work in life - your mission, calling, vocation. I think that probably stays pretty consistent.

Which kept me coming back to this question of, “Who am I, really?” I’ve always been the kind of person people open up to, unprompted. I’ve been told I’m disarming. Someone recently told me, “That’s a gift — use it.” That was true in law, and it’s still true now.

So the work became less about following some prescribed “should,” and more about using what I’m actually good at or have a gift for - listening, connecting, helping people make sense of their inner worlds.

5. “How did you build the business?”

I don’t have a clean answer to this (which, by this point, should not surprise you). Everyone builds differently.

I think the trick — if there is one — is to lean into your gifts. If you love networking, do that. If you enjoy speaking into a camera, do that. If you like writing, lean on writing.

For me, in all the work and jobs I’ve done, it was talking with people. Getting a million lunches and coffees. Joining

For you, that might be something different. And if you don’t know what that is, ask less “What am I good at?” and more “What is fun?”

Marketing and business development have to be fun or you simply won’t do it.

For instance, if you hate cocktail parties - the classic networking scenario - then don’t go. Unless you can learn to like them and enjoy them and feel natural in them - don’t use them as your method of business development and building the business.

And when it’s fun, you also show up more naturally. More relatable. And people fundamentally want to work with someone they can relate to — whether that’s a coach, a therapist, a lawyer, an accountant, whatever.

6. “Why make the changes?”

To put it simply: there’s only so long you can deny yourself.

I could tell a longer story about the exact moment or the circumstances around leaving law, but the real answer is already buried in everything above: something was itching for so long that I just had to scratch it and I couldn’t any longer pretend it wasn’t there anymore.

Which leads me to the question I would invite you to consider (if you’ve read this far): What have you been denying yourself? If you have a feeling, a thought, an ominous sense that you’ve been rejecting a call to do something that, for some reason, seems to just “work better” for you - then at least look at it. You don’t need to make any drastic changes - you don’t need to burn it all down (take it from me, that way is much harder). But, you owe it to yourself to really wrestle with the question and get some clarity on the answers.

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