It’s the end of the year.

The school year, anyway.

The weather is getting warmer. Kids are hanging around various malls and convenience stores and parking lots more. A sense of temporary, unbridled freedom is just around the corner.

For some.

For many others, its the end of the freedom. It’s time to buckle down, get to work, start down the road of the long and winding career path that almost inevitably starts the minute you finish your last exam.

It’s an interesting time - a liminal period, if you will. A time where you can really miss the cues for what will be a fulfilling, meaningful career - and, instead, just go for what “should” be your work instead.

Here are ten ideas that I often share with people at this juncture (and that, if I were speaking to my self 20 or so years ago, would have shared with young Jordan as well).

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Life is long.

Yes, right now, you are probably thinking - “Shit. This better be it. I need to be sure I am making the right choice for myself, my life and my future. This needs to be the career that today me and future me will both love.” Let me tell you something - the odds of that being the case are slim to nil. Some numbers to bear in mind:

• People swap careers roughly 5–7 times in a lifetime

• The average American holds 12 jobs over their lifetime, with an average tenure of about 4.1 years

• Roughly every 3rd or 4th job is also a career change

• The average age for a significant career shift is 39

This means that, even though yes, life is short, it is also long. Really long. So long in fact that you have time to change careers 5-7 times and still be OK. So, don’t rush. You have time.

You will change.

And, of course, with life being so long, you are going to change. Change is inevitable - despite the fact that our typical education and career training seems to imply that you take on one career “identity” based on what you study, and that is a fixed thing. The reality is, nothing is fixed. Your tastes will change. Your interests will change. Your relationships will change. And, the world will change. So, be prepared to shift in response to those changes - not as a way of denying your fixed self, but actually, as a way of embracing your changing self.

No one knows anything.

I remember a guy I knew who used to come to a yoga class I taught. I was freshly finished articling at a law firm and was considering my choices - at the time, I was not planning on going back to law. This guy knew a bit about me and I knew a bit about him - he struck me as really successful, knowledgeable, well connected and very much an expert in his field. After class one day, he pulled me aside and asked me, “So, Jordan - figure anything out yet?” And, I said, “No, not really.” To which he replied, “Yeah, me neither. I still haven’t figured out what I want to do when I grow up.”

He was 65.

My point being - he represents the average, not the exception. 20-35% of people in their 30s-50s report career dissatisfaction. It is a lifelong condition for the majority of people.

The question just changes shape: from “what do I want to be?” to “is this still who I want to be?” But, regardless of how the question is phrased, the answer is still the same so often: “I don’t know.”

So, if you don’t know, don’t beat yourself up about it. You are the norm.

Pursue interests.

In other words, focus less on what you “should” do, and more on what you “could” do.

Do you like art? Is it interesting to you? Do you notice that when you are “doing art” everything else seems to fade away or become less important? Good. Do more of that.

Do you like Excel spreadsheets? Are they interesting to you? Do you notice that when you are “doing Excel” everything else seems to fade away or become less important? Good. Do more of that.

See what I did there? This has nothing to do with money or prestige or what your parents think you should be doing with your life. It has everything to do with you. And what you are really, truly into is almost certainly something that you are, or will be, good at. And, when you are good at something and you find it fulfilling, you are increasingly like to get paid - well - for doing it. But, the pay is secondary. The fact that it feels natural is the important part. That’s the part that says you are moving in the right direction.

The direction of vocation and not simply a “j.o.b.”

So, pay attention to your interests. Don’t ignore them. Don’t put them aside for what you are “supposed” to be doing. That way lies disaster. Or, at minimum, a lot of boredom.

Make mistakes. A lot of them.

As someone who has made a lot of mistakes, I may be biased here. But, please take my word for it. You don’t learn by getting things right. Actually, you learn by falling on your face, embarrassing yourself, and picking yourself up to keep doing what you were doing when you fell - but, differently.

Now, of course, making mistakes sucks. It feels bad. Even when we know that we learn by making mistakes - that still doesn’t take away the sting of it.

In a way, we need to learn how to want to make mistakes. To want to take chances. But, taking chances is scary.

I know, I know. Who wants to be scared? No one. Well, except for roller coaster junkies, or horror movie enthusiasts, or skydivers.

But, as Joseph Campbell has said, “The cave you fear to enter holds the treasure you seek.”

So, if you are afraid of making mistakes (as most of us are), remember. The mistake is the way to the success - not getting it right.

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Don’t ignore the signals.

Over the course of your long life, you are going to receive signals. Yes, signals.

These could be messages from people you trust. Or, feelings. Gut feelings. Physical feelings. Emotional feelings.

Or, these signals could be actual people. That keep popping up in weird, unexpected places.

Or, the signals are opportunities. Chances to do things that are interesting to you or that mean more to you than what you are currently doing. Or, that simply seem fun.

Do not ignore them. They are important. And, they are annoying.

So annoying, in fact, that when you do ignore them, they will keep coming back. Louder and more irritatingly. Telling you, “Listen to me! I am trying to tell you something! For the love of God, why can’t you just hear what I’m trying to tell you!”

And you will say, “Yes, but later. I am busy right now. I have priorities that I need to address. Can’t you see that I am doing the thing that you told me to do earlier?”

That’s the challenge. The signals might change their mind from time to time. And, so, you might also be called to change your mind. That’s OK. Go with it. The signals aren’t there to trick you - they are there to teach you and lead you to what is calling you forth. So, listen.

Make mentors.

I attribute 99% of my success (or whatever you might call whatever it is I have done with my life) to having had the most unbelievable mentors in my life.

These are people that decided, for whatever reason, that I was worth spending some time with (and on), letting me into their worlds, and imparting the wisdom they have from their deep and interesting lives, on to me.

But - and this is key - they didn’t simply decide one day to be my mentors. No, I had to turn them into mentors.

How does one do that? Well, let’s turn to the words of Rabban Gamliel (a first century A.D. Jewish scholar):

“Make for yourself a teacher.”

But, what does this even mean?

You have to choose actively. Wisdom doesn’t come to you passively. You construct the relationship through intention and effort.

Your teacher may not know they’re your teacher. You can designate someone as your mentor unilaterally - by studying them, following them, returning to them - and they may never even know you did it. And that’s totally cool.

The act of choosing is itself formative. Deciding who you want to learn from forces you to know what you value.

So, go. Make yourself a mentor. They will have more impact on your career than I could ever try to explain here.

Use your hands.

Literally. Just do stuff with your hands. Build things. Make LEGO. Carve wood. Paint. Draw. Sculpt. Swing a bat. Throw a ball. Play an instrument.

But.

Do all these things without your phone. Without a screen. Without a distraction.

And, then, notice: “What am I paying attention to right now?”

Because - and I am willing to bet - in those moments you will be paying attention to your hands and what you are making. And, when you demonstrate to yourself that you can make things with your hands, imagine how much agency you can have in making a career that really works for you?

Go slowly, on purpose.

I touched on this above, but really - don’t rush. There’s a lot of time - even if it feels like there isn’t, and you had to have everything figured out yesterday.

But, there is additional value to going slowly. A lot like working with your hands, but differently. Going slowly forces us to pay attention to what is happening around us and in us. Going slowly allows us to hear the signals more clearly, to get into states of flow, to be really, fully, truly engaged in our work.

Ever notice when you are in a rush to get somewhere, you miss the turn to the place you’re trying to go? It’s because you are not moving slowly enough to notice it.

I am sure there are a lot of things you don’t want to miss - in your career and, perhaps more so, outside of it. So, slow down.

Be a kid.

Laugh about what is going on. Get emotional - and don’t apologize for being emotional.

In other words, play.

There’s this experiment that I refer to in some of my presentations where kids were asked to build a tower out of spaghetti and a marshmallow, and the marshmallow had to be on top at the end of 18 minutes.

Long story short - kindergarteners consistently built taller towers than lawyers, Stanford MBAs and CEOs. Why? Because they were having fun with it. They weren’t concerned with how tall it was going to be at the end. They were only concerned with what was possible, what they could try making, and what would happen if they put a marshmallow on top. They didn’t care if it fell over. In fact, they were happy to make mistakes. Because each time they made a mistake and the tower fell over, a) they laughed and b) they learned what worked and what didn’t, and tried again.

It was simply fun for them. And, because it was fun, they were successful at it.

So, whatever it is you are doing, make sure it is fun. While I’m willing to bet you will be more successful at that than the thing that is less fun for you, I know for certain that you will enjoy it more. And, that’s worth a lot.

One more thing.

Whatever you do - whatever path you choose, abandon, rediscover, or stumble into - remember that you are not behind. You are not late. You are not doing it wrong.

You are, in fact, right on time.

Even if you can’t see it yet. Maybe, especially if you can’t see it yet.

Now go make some mistakes and have fun (and, not necessarily in that order).

Jordan Nahmias is the founder of Unstuck Consulting, an executive coaching practice for lawyers and other professionals. A former entertainment law partner in Toronto, he helps high performers navigate burnout, career transition, and identity.

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About 9 years ago was the last time I showed my photography. On a relatively public scale anyhow. It was at The Artist Project, a Toronto annual art fair that usually has a good assortment of interesting work and people.

Historically, it had been a good show for me. I would show up, fill my booth with my work, and sell most of it by the end of the weekend. It wasn’t necessarily a money maker. Art fairs are really expensive, particularly if you are giving up your time at your other job.

But it was satisfying. I got to meet lots of people, talk about my work, and see how it impacted the people who would look at it and engage with it.

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That really is, I think, the real satisfaction of making art. You put something out there that you — and perhaps only you — find interesting.

And then, sometimes, someone else finds it interesting and they ask you about it.

And in talking about the art, you really are talking about yourself.

But in so doing, you connect with the other person. You find some commonality that, without the art as provocateur, would likely never have been found.

At that 2017 show, the difference was I didn’t sell one piece. Not one. It was devastating. And I decided then and there: I am not going to show my work again.

It was a ridiculous decision. One that I am probably still getting over. I, effectively, cut off a part of my creative life in that moment that was entirely to my own detriment.

What was so devastating was not just the fact that I had spent so much money printing and framing the work and had no one buy it. Although that did really suck. What was worse was that it felt like a rejection of me. That my work was no longer good enough — for the buyers, for people’s interest. It felt personal. Especially because, historically, that style of work would sell well.

So what happened?

I doubled down on two sure things: a) practicing law paid better and b) my work was never rejected as a lawyer.

Now that I’ve had almost 10 years to think about it, I think what happened was that I was putting work out there that I thought I “should” be putting out — what I thought others wanted. And in so doing, the work had less and less of me in it. It felt less honest. Less truthful.

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The work I was making for the market was for the buyer. And they knew it. And so they didn’t want it.

It’s weird how that kind of thing comes out in all sorts of ventures and careers. When you are doing something because you are “supposed to,” people can tell. They don’t engage with it. Because what they’re sensing (and I think people always sense this) is that someone is just not being truthful about who they are.

Maybe this was a habit I had. Mistaking self-protection for self-knowledge. Maybe I still have it.

Earlier this week, a proposal I had out for a law firm workshop was rejected. Thirty minutes before we were scheduled to speak, the learning leader sent me a note. No longer interested. No real explanation.

It felt like a gut punch. I could use the income. But more importantly, it felt like: this isn’t working. Maybe it’s time to pivot. Maybe it’s time to double down on something more certain.

The challenge here though isn’t really whether I’m good at what I do. I know I’m good at it. It’s more: Is this as truthful to myself as it can be?

And sitting with that question, something became clear.

Maybe what I am most interested in doing actually has nothing to do with law firms, or lawyers, or any specific group at all.

Maybe, instead, it is people who have done all the things they thought they were supposed to. Who were good at it. Who did well. Who are successful. And who are now asking - now what? I want more. More success, more meaning, more purpose, more life.

Returning to the photography - one thing I’ve noticed lately is that I am way more into sharing my work than I have been in years. Perhaps it’s the sense of unraveling that apparently takes so long once you leave a profession that was not truly who you were, and you start bravely going down the path of figuring out what truly is.

To quote the work of Mark Epstein: maybe it’s allowing yourself to fall to pieces without falling apart.

And that is a scary, yet I think, incredibly brave and honest, choice.

If you’re reading this and you’re wondering, “I wonder what it would be like to be less afraid of failing, and more able to pursue success on my own terms,” then have that conversation with someone you trust and see what happens.

Unsure what to do next? Looking for more certainty? Welcome to the club.

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What would it take to get on a roller coaster that had no clear end in sight?

Not a coaster where you can trace the full track from the line. The kind where you can see where you board, where you return, and roughly what you’re in for.

I mean one where you get on, the ride starts and you have no idea where it ends.

My guess is that that coaster would have a very short line.

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This is what I was wondering about yesterday while waiting in line for a roller coaster with my daughter at Canada’s Wonderland. It’s a theme park. Near Toronto. Where I live.

My visit to Wonderland coincided with a day on which I was also speaking with a coaching client of mine. A lovely, creative, entrepreneurial person who was facing a specific dilemma:

Do I embark on a new aspect of her business? One that will require considerable investment, and potentially, considerable rejection? And, even more significantly - failure?

Now, the classic advice is, the classic advice is, “nothing ventured, nothing gained.” Right?

And, it’s true. But, it’s also entirely unhelpful. Because it doesn't tell you what to do with the fear that nothing might be gained at all regardless of what chance you take.

Here’s what I’ve come to know: There is no certainty. Ever.

Consider the roller coaster again.

The track and the little house that you enter to get onto the train acts like a sort of permission structure. It lets you say yes to the fear because you can see where it ends. That doesn’t make the ride any less scary or fun - in fact, you can probably let loose more knowing where you are going to end up once the ride ends. But, it does make it that much easier to get on board the ride in the first place.

The problem for my client - and the rest of us, of course - is that our careers don’t have tracks or those cute little huts. The same thing goes for building a business, or really, for making any decision that matters at all. You just don’t get to see the ride play out before you commit.

And, that is often very frustrating. And paralyzing.

Because, what we are really looking for here is a certainty in outcome.

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So, how can you continue to move forward while still not knowing how things will turn out?

You stop focusing on how things will turn out, and just focus on the decision instead.

Simone Stolzoff, in his new book How Not to Know, puts it this way: separate the quality of your decision from the quality of your outcome. They are not the same thing. A good decision can produce a bad outcome. A bad decision can get lucky. What you control is the former. Almost never the latter.

Why I like this approach is that it focuses you on what’s actually in front of you - the information you have, the values you’re acting from, the decision you can make right now - rather than a future you can’t see (and, even if you could, couldn’t guarantee anyway).

I’ll tell you how I used it today.

This article is a day late. It’s nowhere close to perfect (or even ideal). I’m not sure the roller coaster metaphor will land. I’m genuinely uncertain whether anyone reading this even has strong feelings about theme parks.

But I what I do know is this: writing it was the right decision. Not because of what it might produce (the readers, the reach, whatever business might follow). But because it was the honest, present, best-available-information thing to do today.

That’s it. That’s the whole thing. And, if my theory proves correct, if I just continue to make decisions this way, then everything will work out just fine.

Remember: You don’t get the certainty before you board. You get it - if you get it at all - only at the end.

Unsure what to do next? Looking for more certainty? Welcome to the club.

But, if you need some help…

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This week I have the treat of sharing an interview I did with the lovely on her podcast Non-Billable Hours (which you should all subscribe to, right now).

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We spoke about:

• the choice of law school as “the thing that smart people do when they don’t know what do to with their lives”

• the path that you can end up on, and the pressure to stay on it, once you are in (and out of) law school

• identity and questioning the definition of success

• embracing creativity

• how to build a meaningful career and what it sometimes really takes to get there

Oh, and the story of how I had to give up talking for a month.

If you’ve got 45 minutes or so, IMHO, it’s definitely worth the watch or listen.

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

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There’s a funny thing that happens in life.

You’re good at something and so, people start telling you - or you start telling yourself - “Hey, I’m good at this. I should do this more. Maybe I can make a living off of this.”

Or, there is something you think might make a decent career, and so you look at it, and explore it, and study it, and eventually realize, “Oh, I’m good at this. I guess this is what I’m going to do.”

Either way, you end up in the same place:

You are doing something that you are good at.

The common thread through all of these, though, is that at no point did the person in question stop to wonder, “Just because I’m good at this, does that mean it’s the right thing for my career?”

It’s easy to overlook that question.

We are so focused on being good at things - at being productive, at performing well, at achieving high grades or other accolades, at making money and living a comfortable life - that we neglect to ask whether the way in which we are doing these things is the most suitable to us at a deeper level.

You could call it soul. Or your core. Or your spirit. Or your calling. I’m not really fussy about which you choose.

In my case, I like to use the word “calling”. I always knew that being a lawyer wasn’t my calling - and others knew it. But, I was good at it.

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And, for a long while, I was so good at it, that even as I ignored the question of “calling”, I started to think: “Man - I really don’t like this. But what else would I be as good at?”

That question is a self-made trap.

In the language of psychology and coaching, it’s what we might call a “limiting question.” It might feel like an open question — but it’s not. Because it implies the foregone conclusion that there actually isn’t anything you could do this well.

So, why bother?

I had a friend who used to say this all the time. He was a lawyer (of course). He would often say how much he hated what he was doing — the work, the firm. But the answer to his own question was always, “Yeah, but what else would I do?”

Well, fast forward a few years.

He left law. Tried consulting. Tried entrepreneurship. Found a company he liked. Bought it. Transformed it. Sold it for a hefty sum.

Now, you might be saying, “So what? That could be anyone. Not me though.”

I get that. I said the same thing for longer than I’d like to admit.

It was along the lines of, “Jordan, you’re pretty good at this law thing. Sure, you could do some other things - and maybe even be good at them - but, who are you kidding? No one is going to pay you to do anything else that you are good as much as this.”

But here’s what my friend, and others I know, have figured out: competence at something is not the end. It’s the beginning.

The problem isn’t that you’re good at what you do. The problem is that you’ve let “good at” stand in for “right for.” They’re not the same question. They’ve never been the same question.

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Barbara Sher spent decades watching talented people trapped in exactly this spot — not because they lacked ability, but because no one had ever asked them to aim that ability somewhere that actually mattered to them. She was onto something. You’re not broken. You’re just aimed wrong.

The theologian Frederick Buechner had a phrase for the place you’re trying to get to.

“Where your deep gladness meets the world’s deep need.”

Not just where you’re useful but where you feel you’re most alive.

I was asked about this yesterday in a podcast interview actually. What did it mean to be “alive” in my own work? My answer, meandering as it was, ended up summed as follows: it was when I felt like I was just “doing me”. No pretence, no posturing - really, just being myself in my work, noticing that I was continually drawn towards it, and seeing what came of it.

That’s the question underneath the question. Not “what else could I do?” but “where does what I do best connect to something I actually care about?”

So here’s my push for today:

Write down the last three times you felt genuinely good at the end of a workday. Not productive. Not praised. Actually good. What were you doing? Who were you helping? What problem were you solving?

That’s your data. Not a personality test or an assessment (although, if you want to take one, go here). Just your own memory, reminding you of something that you know you already know.

You don’t have to blow up your career to answer the question. You just have to stop letting competence be the only answer you allow yourself.

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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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.

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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.

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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.

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

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.

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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.

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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.

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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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