Well, it’s that time of year again.

Summer is wrapping up. Kids are picking out their clothes for the year ahead. Parents are very ready for kids to go back to school. Or is that just us?

That time when you see a new schedule coming up.

And with it, the need to potentially shift how you’ve been doing things for the past few months.

In other words - the need to re-align.

It’s a word that has been coming up regularly in my conversations lately.

The idea that there is an opportunity to shift things around to align more with what really matters.

Subscribe now

But, what does it mean to “be aligned”?

We talk about it all the time:

• Align yourselves to your values.

• Re-align your work to your deeper needs.

• Your back is out of alignment (this one might just be me).

I have a client who I was speaking with last week who used the expression that he is not feeling aligned in his work.

So, we spent some time looking at what it is he’d like to be aligned with.

In the case of this client, he kept coming back to the way in which he wants to work in the world.

To feel “aligned,” he needs:

• to be with people more

• to be at an office more

• to be in conversation with others more

• to feel like he is having more impact

In other words, his ways of being aligned with what matters rely on his doing things.

Just, doing them “more.”

And isn’t that always how it feels?

I say this as a guy who leads a group coaching program called Pursuers of More, but seriously - is “more” always the right answer?

This “do more to get more” thinking is nothing new.

Yes, in many ways, this might reflect the Puritan work ethic that North American society is completely awash in - and perhaps, founded on.

But this view also aligns (no pun intended) with the thinking of many other writers, teachers and thinkers. Small-time intellectuals like Friedrich Nietzsche, Jean-Paul Sartre and Herminia Ibarra.

Sartre: “Man is nothing else but that which he makes of himself.”

Alignment with what matters comes from constructing our lives into something more. We are not enough on our own - we have to mold our lives, and our Selves, into something greater.

Sounds like a lot of work.

For many of us (myself included) this just makes sense. I can tell you without one shred of untruth that this might be my own personal biggest struggle. Every time I think that something needs to change - that I am out of alignment - my instinct is to just do more. Work harder. Pay more attention to something. Read another book. Listen to another podcast.

Surprise: none of that works.

Which makes me think: hmmm. Maybe this is about doing less somehow.

Turn to Herminia Ibarra: “Our working identity is not a hidden treasure waiting to be discovered at the very core of our being […] we tend to latch on to authenticity as an excuse for sticking with what’s comfortable.”

Great. So now getting aligned is not exactly about doing anything specifically, but rather, getting uncomfortable? As in, “it’s not you being authentically yourself that is going to get you to your working identity. Rather, you need to do things to get more uncomfortable and turn away from what you think is really at your core.”

This is confusing. What I think Ibarra means here, though, is that spending time looking at our values is really not going to help us, because there is nothing to uncover. The answer is right in our faces. The challenge, rather, is that we can’t see what’s right under our noses. “Thinking and introspection should follow experience — not vice versa.” Meaning - go out and do. Then - and only then - will you see what is hiding in plain sight.

And what about Nietzsche?

His view was that we want to become those we already are - human beings who are new, unique, incomparable, who give themselves laws, and (a lot like Sartre) create ourselves. To that end, we need to become the best learners, discovers and doers of everything that is necessary in this world to more fully become our Selves.

There it is again. Doing.

But didn’t we get into this discussion precisely on the premise that the doing of more is exactly the thing we are trying to avoid?

The thinker I rely on most in respect of this question, though, is Parker Palmer. Palmer, a Quaker writer, teacher and the author of many insightful books including Let Your Life Speak and The Courage to Teach, says:

“Before you tell your life what you intend to do with it, listen for what it intends to do with you.”

In other words - what you’re supposed to do with your work is something given rather than chosen. What you were born with, not what you constructed yourself to be, in order to be approved of.

Contrast that with Nietzsche and Sartre, who hand you a chisel and tell you to carve yourself into being. Palmer doesn’t think you need a chisel yet. He thinks you need to put down whatever tool you’re already swinging - the busier calendar, the new morning routine, the fourth podcast this week - and actually listen to the life you already have before you decide what to build next.

Palmer’s alignment is subtractive. Most of the genre says: find your values, then build a life to match them. Palmer says the life is already speaking and you’ve been talking over it. “Vocation does not come from willfulness. It comes from listening.” The Quaker “way closes” language matters here — his closed doors aren’t failures, they’re data. He got fired, dropped out, sank into two major depressions, and reads all of it as information rather than detour.

I said earlier that “re-align” has been showing up everywhere in my conversations. Here’s my honest read on why: it’s a word people use when they can feel something is off but the only verb they have access to is “do.” Re-align gets used the way “optimize” does — as if the fix is always a better system, a smarter routine, one more adjustment. But an adjustment to what? You can’t align to a target you haven’t actually located. And you can’t locate it by adding more inputs. You locate it by getting quiet enough, for long enough, to hear what’s already there.

Which brings me back to my client. When we dug into “more people, more office, more conversation, more impact” — none of those were wrong, exactly. They were just downstream. They were the four things he could act on by Monday: buy a train pass, book a desk, put a lunch on the calendar. What he hadn’t done yet was ask what those four things were actually pointing at. When we slowed down, it wasn’t more of anything. It was one plain sentence he’d been talking over for the better part of a year: he built a career that rewards him for being right, and he misses being around people who let him be uncertain out loud. That’s not a doing problem. You can’t add your way to that. You can only stop long enough to hear it, and then decide what, if anything, changes.

So here’s what I’d offer instead of a new fall routine. Before you build the new schedule — the earlier alarm, the reorganized week, the “this is the season I finally get serious” plan — try Palmer’s move first. Don’t ask what you should add. Ask what your life has already been telling you that you’ve been too busy doing something about it to hear.

Then build the schedule around that. Not before.

Jordan Nahmias is a vocational strategist and the founder of Unstuck Consulting - a coaching business for high achievers doing the work they were “supposed” to do, but (perhaps not so secretly) want to design and build careers and businesses that more truly reflect who they are, what matters to them, and live on their own terms a little more every day.

→ Take the Beyond Success Assessment.

→ Join the Community.

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

Subscribe now

There’s a phrase that I am very familiar with:

“I could do it if I tried.”

And, while it often sounds like confidence, it’s really a very fancy way of staying stuck.

Imagine you are rock climbing. You are staring up a sheer face and thinking: “
Man - that’s really high.”

And, then - you don’t climb. You might think, “I could do it if I really tried, but…no need for that now.”

And, there’s no shame in that. It’s just a nothing burger - a non-event.

And, I think, that’s the issue with it.

Because, enough nothing-burgers add up and you start to notice.

The same thing happens with careers, and it usually arrives in one of three outfits:

It’s not worth the effort. Where I am isn’t that bad. I’m afraid of what it would take.

Notice what none of them say: not one of them is “I can’t”.

Rather, it’s “I won’t”.

And, when we phrase it that way, we realize that we are actually putting effort into - trying - something very different.

But, what is “trying” anyway?

To me, the first obvious answer is cost.

In the case of a career change: Four more years of school. A pay cut. Starting at the bottom of a ladder you already climbed before.

This is real, but is this “it”?

You have done harder things, certainly, and for worse reasons. So, if cost were the only obstacle, you could get over that realy easily.

The next answer then, might be, fear of failure.

But, are people really afraid of failing? Or, rather, is it failing in front of the people who know them?

Kishimi and Koga make this argument in The Courage to Be Disliked - that nearly all of our suffering is relational, and that freedom has a price, which is the willingness to be thought less of.

In other words, being “disliked” is not a failure. It’s actually a sign that you are succeeding.

When I was leaving law, the time it took to change paths had little to do with logistics. I knew the numbers. I knew the next phase, as uncertain as it was, would be very psychologically taxing.

What kept me stuck most was: what will people think? Will they think I failed? That I couldn’t cut it?

But, in the end, here’s what happened. Nobody cared.

Most people were happy for me. Some might have worried a bit.

But not one person thought less of me. I have never once, in the years since, met the critic I spent so long negotiating with in my head.

Now, I’m not saying, “Go for it because nobody cares.” That way disaster lies.

What I am saying is that we need to be careful of confusing approval for belonging.

If I change - my title, my career, my identity - am I still accepted? Do my friends still respect me? Do people still take me seriously? Does my wife still love me?

That’s not vanity. That’s a fear of loss, and it’s a different fear than the one you think you have.

Which brings me to the only question I think is worth asking.

Not can I do it?

But, rather, “What do I need in order to really try?”

That question isn’t answered by motivation. It’s answered by things that are far simpler (in many ways): inventory; runway; the conversations you’ve been postponing; permission to be bad at something again after a decade of being “good”.

And while you can’t necessarily answer the question of, “Am I brave enough?”, you definitely you can answer the questions raised on that list.

I can’t tell you what’s on your list. Which is why you need to write it. And, when you do, notice - the change you have in mind stops being a referendum on your character and simply becomes a set of logistics.

And logistics, you can definitely do.

I’ll be speaking at the quarterly PodCast Alliance Meet Up.

Details below, and you can sign up here if you’re into that sort of thing:

https://e.sparxo.com/Podcast-Alliance-August2026

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.

→ Take the Beyond Success Assessment.

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

Subscribe now

“We fear ugly, so we never start. We fear that it will never get better. We see no promise that our truly rough first attempts might become the thing we hoped for, the thing that we feel pressured to make perfect. We’re scared others will see us and judge us; that our ugly first efforts will reflect back upon us.”

This is a quote from David duChemin’s “Start Ugly” - a fantastic read I just completed on the perpetual challenge of creating.

duChemin ostensibly approaches his topic through the lens of the creator - the artist - who is continually challenged by the prospect of the thing being made ending up “ugly”.

Share

And, so, his thesis is, summarily, that if we can just agree to “start ugly” - meaning, accept from the get-go that this thing we are making may simply not end up how we so desire - then it gets easier to start.

And this is important because, as duChemin puts it: “the beginnings […] are the most important part of the creative process.”

Reading duChemin, I was taken back to another book that I adored when I read it. Ichiro Kishimi & Fumitake Koga’s, “The Courage to Be Disliked”.

Based on the work of Alfred Adler (who we’ll get to later), Kishimi and Fumitake take on the same challenge as duChemin - the challenge of not starting because, to fail would essentially mean to be disapproved of.

Or, in Adlerian terms, to be inferior to the prototype to which we aspire.

For instance, take this parable from Kishimi and Koga:

“I have a young friend who dreams of becoming a novelist, but he never seems to be able to complete his work. According to him, his job keeps him too busy, and he can never find enough time to write novels, and that’s why he can’t complete work and enter it for writing awards. But is that the real reason? No! It’s actually that he wants to leave the possibility of ‘I can do it if I try’ open, by not committing to anything. He doesn’t want to expose his work to criticism, and he certainly doesn’t want to face the reality that he might produce an inferior piece of writing and face rejection.

He wants to live inside that realm of possibilities, where he can say that he could do it if he only had the time, or that he could write if he just had the proper environment, and that he really does have the talent for it. In another five or ten years, he will probably start using other excuses like ‘I’m not young anymore’ or ‘I’ve got a family to think about now.’

He should just enter his writing for an award, and if he gets rejected, so be it. If he did, he might grow, or discover that he should pursue something different. Either way, he would be able to move on. That is what changing your current lifestyle is about. He won’t get anywhere by not submitting anything.”

What’s this guy’s issue? Would it be so bad to write something that was not necessarily liked, or approved of, or widely accepted?

Yes. Yes it would.

Subscribe now

That is exactly the point. From the outside, we can easily say to someone, “Look, your life won’t fall apart. The sky won’t fall. It’s OK to fail.”

But, when we’re in it, we lose that sense of objectivity. Because, the sense of fear that we feel in the face of the prospect of failure, or being disliked, or not meeting our own (or others’) expectations of our potential, can be (and often is) completely overwhelming.

And, so - like the author Kishimi & Koga cite above - we just stay stuck.

Now, this is not for lack of ability. Most of us know that, even when it comes to the challenges or changes which seem the most out of reach, that is not a comment on whether we are actually able to make that change or meet that challenge. (If you're not yet sure the change is even yours to make, these are the six signs you've already outgrown the career you're in.)

So what keeps us stuck then?

Fear.

I see this all the time with people I work with. I see it with myself too. Here are some examples:

• The fear that my idea might not work out as well as I hope if executed.

• The fear that a client’s desired career path will not only not work out, but that that failure will result in embarrassment and shame (compounded fears).

• The professional who fears failing in his career, and so, always overworks — the logic of pushing through, right up until the pushing itself becomes the thing that takes him out of commission.

• The bright child that always fears that she might not gain the highest grade in exams, and so, hesitates to do her best work and, as a result, doesn’t succed.

duChemin spends considerable time addressing fear, and concludes as follows: “…the best antidote to an all-consuming fear of failure is the repeated experience of failure itself […] the more we fail, the less we fear that it will harm us.”

So, to recap, we need to be unafraid to fail, and the antidote to the fear of failure is…to fail?

This begs an interesting question - what do we need to do or be in order to be willing to fail?

According to Adler: “If people are courageous and suffer defeat they are not hurt so much, but shy [read: less than courageous] people tend to make their escape to the useless side of life as soon as they see difficulties ahead.” (Adler)

Aha. So, we need courage to fail willingly.

And, what is courage? duChemin defines it in two distinct ways, and in both cases, by telling us what it is not:

1. “Courage isn’t the absence of fear. It’s not the feeling of bravery. It’s turning to that part of us that is screaming, ‘What if this is a horrible failure?’ and saying, ‘I have no idea, but let’s find out.’”

2. “Courage isn’t something some of us have and some do not. Courage is a choice to listen to the fear and to act in hopes of proving it wrong, and it is available to all of us, though ‘available’ has never meant ‘easy.’ For most of us, it doesn’t look like the stuff for which we win medals. For some, it’s just getting out of bed or writing the first lines of the new novel. For others, it’s sending the email or pressing publish on a blog post.”

So, this is all great - but what do you do with this discovery?

Turning back to Adler - if we think of what we fear (and avoiding what we fear) as actually serving a goal (i.e. the young novelist isn’t blocked by fear; his not-writing is for something), then fear becomes something else - a signal as to direction. If fear takes you towards an end that does not serve you, then acting counter to the fear (i.e. doing the thing you are afraid of) opens a doorway into what you actually need to do to get where you want to go. In Adler’s words: “The road that seems the most difficult is in fact the most direct.”

So, here’s the invitation:

Take five minutes. Now. Write down a list of things you’ve been avoiding - things that you aren’t necessarily afraid of doing (although, those would work too), but rather, actions as to the outcomes of which you are uncertain and, perhaps, are scared of not ending up as you’d most hope.

It could be that social media post you wanted to write.

It could be approaching that potential client for lunch.

It could be turning down work that you know won’t help you build your business.

Whatever is on that list - pick one. And do it. See what changes, what becomes possible and how your relationship to fear - and courage - shifts in that choice to act.

And, if you want, tell me about it.

P.S. Starting in September, the Pursuers of More is going to be exploring the courage it takes to navigate your next challenge when you’ve checked off all the boxes and are wondering “Now what?” There are 2 spots left. Sign up here.

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.

→ Take the Beyond Success Assessment.

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

Subscribe now

There is an interesting phase of when you decide it’s time for a career change that I refer to as The Abyss.

On the face of it, it sounds scary, right?

A bottomless hole that you fall into, never knowing whether you can climb out, or, if there is actually an exit somewhere deep down in there.

I’ve noticed that this Abyss - the period of falling uncertainty with little direction besides downward - is the reason many folks avoid the challenge of making a major (or even minor) career change.

In other words - if we suspect the Abyss is forthcoming, we get scared. And what do we do when we get scared?

We flee.

At least most of the time.

There are, of course, times in life when we are scared and, yet, we keep going.

Roller coasters. Haunted houses.

In those cases, we know there is an end point in site. And, so, we realize that the period of fear is temporary. For some reason or another, that makes it easier to stick with it.

Subscribe now

Not so with the Abyss. Because, despite the fact that on some level we know it really can’t last forever, when we’re in it, it does not feel that way at all. It truly feels like the Abyss has no bottom. Much like scuba diving, when you hit a certain depth, you can’t tell which way is up and which is down, and both seem to go on forever in either direction.

It’s completely disorienting.

I distinctly remember entering the Abyss in my own career.

It was the beginning of 2022, I had just left my law firm, and had quite literally no idea as to what I was going to do next. And, no amount of advice or comfort or third party insight helped the fact that I was certain I was falling into a hole with no discernible exit point.

It was terrifying. And, yet, I knew it was also necessary. I don’t know how I knew, but I just knew.

And, so, I stuck with it. And it sucked. At the time, much like sitting through a really painful first date, I wished it would just end. And, in this case, I couldn’t even ask for the bill and leave.

That Abyss lasted for a period of about a year. It was better at times and worse at times. But, it was a year of really bumping around in the dark, waiting for clarity, trying new things, and quite seriously just having no idea what was really going to happen.

And, I don’t know if there is anything that could have made it go quicker. People will tell you that you can do things or think things or feel things to make it pass more rapidly, but I seriously don’t believe that.

These things have a way of simply having their own schedule. Which really doesn’t jive nicely with how most of us are wired - we want things to happen quickly, we value efficiency above almost all else, and if we don’t see productivity, we are convinced something is wrong.

And, so, being patient - sitting in my dirty diaper for that long (as my old therapist would put it) was simply necessary. As Rumi may have put it, the wound was the work.

Share

It took the time it needed to take for me to come to my own realizations and knowledge. That included enjoyment but also suffering, learning about myself and what I really cared about, and making enough mistakes (and having enough successes) to have a better idea of to what I could turn next.

And, for better or worse, there is no way I could have expedited that.

The real question then is - if we know we can’t make time move faster - how can we make the time that we are in the Abyss feel better?

Well, let’s go back to fear. In a weird way, we need to want to be in the space we’re afraid of. We need to want to be in the Abyss. We need to reframe the thing we’re afraid of into the thing that we actually want more of. We have to want to go through it and know that, at some point, it will end - and - we’ll be better off for having gone through that.

That may require a leap of faith. And any leap of faith - any jump across a chasm in the Kierkegaardian sense - requires courage.

I often tell folks in my workshops (drawing on the work of David Whyte) that the root word of “courage” is “coeur” - the French for “heart”.

Meaning - if we have courage in the face of fear, we are learning to have a heart for - or love, if you want to get mushy about it - the thing that we have been avoiding - the thing that we have been afraid of.

And, ultimately, I think that’s the real job here. To learn to love what is happening for us - even when it’s in the shitty, deep, dark, scary, annoying, frustrating Abyss. Because, since we can’t get out of there any faster than time will allow, we might as well love it while we’re in there.

P.S. The next cohort of our community, the Pursuers of More starts in September. There are 2 spots left.

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.

→ Take the Beyond Success Assessment.

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

Subscribe now

Last week, HBO premiered a documentary series about Burning Man, The Man Will Burn.

I’m not here to review it.

But watching the first episode got me thinking about the place itself - what it is, what it means, and what it actually does for the people who go.

I went for the first time in 2018.

My friend Mike had been on me for years at that point. He kept saying, “Jordan, this really is the place for you. You will love it.”

Now, Mike wasn’t off in his instinct. Say what you will about Burning Man - and plenty has been said - it is a place of wonder and awe, experimentation and art.

To put it succinctly (which is hard): it’s a temporary, fully functioning city that exists for one week in the Black Rock Desert of Nevada. Roads, addresses, a postal service, bars, cafes, a DMV, status, communities, cliques, trends - and a very long list of rules. A whole civilization, built to code, gone in a week.

Share

And, like any city, it tends to attract a certain type of person.

The people I went with, the people I already knew going, and the people I met out there all had a striking similarity:

They were looking for a place where they could ditch their work identity and fully inhabit their “true” identity.

This is not what I expected to learn going to “The Burn” (that’s what those in the know call it).

In fact, I didn’t really expect to learn anything.

I expected to party for a week, get really dirty, get really tired - but also get inspired by the art and the music and the way of life out on the Playa.

And then there it was again - everyone I met, quietly leaving their work identity at the gate.

But what did that mean for me?

I walked away from that first Burn knowing something simple: you don’t need anyone’s permission to do your thing. You can just go and do it.

That’s hard for most of us. We spend our lives running someone else’s checklist - how we’re supposed to work, parent, create, live. The shoulds.

So what happens when you land somewhere with no expectations on you at all, beyond a few rules everyone agreed to just to keep the peace?

A lot, it turns out.

You get more creative. You dance how you want. You wear something absurd, or nothing at all. You take a new name - plenty do. You get to set down the whole identity you walked in with, because no one out there is asking you to keep carrying it.

But here’s the part people miss: it isn’t a vacation. You still have responsibilities out there - to your camp, to the people around you, to the work of keeping a city alive. You don’t get to drop those. You just get to meet them as whoever you actually are.

That’s the thing. Not freedom from your obligations - freedom inside them.

So why am I telling you all of this?

Subscribe now

Because, despite what most folks believe, Burning Man is really no different than the rest of life. It isn’t the exception. It’s the mirror.

There is no list of shoulds dictating how you’re supposed to work, or parent, or create, or live. And wherever you think you’ve found one - well, maybe there’s a separate question worth asking: Where did this come from? And why am I still following it?

Does this mean you need to escape? No.

Does it mean you need to quit anything? No.

But it does mean you can start doing things your own way and see what unfolds - without waiting for anyone to say go.

For me, in 2018, the should I finally set down was that I should be anything other than my creative, entrepreneurial, risk-taking, and often rule-breaking self.

What’s one you could quietly test this week?

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.

→ Take the Beyond Success Assessment.

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

Subscribe now

When Do You Know It’s Time to Fold?

I recently started playing mahjong. I really like it. Particularly because, like poker, there comes a point during certain hands when your odds of winning go to zero and you know you can’t win.

So is it time to leave the table? Or just change things up?

In all cases, it’s your choice. And that’s what makes it so hard. As a lawyer facing burnout, you likely haven't been told it's okay to pivot or rebuild. Instead, the traditional advice is, “Grin and bear it,” or, “This is just how it is, so you better get used to it quickly.” And, many do. Miserably.

But instead of considering what you should do, what if you ask what you could do? Framing it that way, is leaving the only answer?

Four ideas changed how I think about this: when to fold, what to try, why we cling, and what actually sustains us.

The Competency Trap: Success as a Cage

Oftentimes, the first real challenge when considering whether to change or leave practice is the thought that, “I’m good at this (and, they pay me pretty well to do it). Why change anything?”

This is what Herminia Ibarra in the excellent Working Identity: Unconventional Strategies for Reinventing Your Career, calls the “competency trap.” Proficiency triggers both an internal sense of mastery, external validation and rewards. The thing you’re best at also becomes the most limiting factor about your work life.

In law and the other professions, this trap cuts deep: you're earning well, you've built years of expertise, yet you feel trapped by burnout. This isn't normal stress - it's a signal that your skills and expertise have become a cage instead of a path to the freedom you thought they would lead you to.

But, is that enough to make a change?

Share

Why Professionals Quit Too Late

In her book Quit: The Power of Knowing When to Walk Away, Annie Duke (a former poker player) argues that most of us quit too late, not too early, because we overvalue grit, underestimate uncertainty, and ignore the hidden cost of sticking with the wrong things.

Herein lie two more traps.

The first: As long as there feels like a chance of things turning around, it will always feel too early to give up or make a change. When you are good at what you do, the “maybe it’ll improve” story is always kept alive.

The second: the sunk cost fallacy. This is the idea that, if I quit now, I’ll have wasted all that time/money/energy/etc. But is this actually true? How much of that will you waste going forward if you don’t quit/change paths? Imagining the future signals that would tell you it’s time to leave, and writing them down, increases the chances you’ll cut your losses when you should.

The real question isn’t whether a career change is inevitable - it’s when you’ll pursue one intentionally rather than in crisis.

You can hear more of Duke on her thinking here (courtesy of McKinsey & Co.):

How Career Transitions Actually Happen

But, even if you do decide it’s time to leave - or change it up - the question most folks get hung up on is, “To where do I go? What could I do as well as this, and how can I even figure that out?” Ibarra’s research on how legal career transitions actually happen challenges the all-or-nothing narrative.

Ibarra posits that it’s not about figuring out what you want and then jumping. In fact, it’s entirely the opposite. Try things - experiment constantly - until you have effectively invented your new future.

This makes sense. From a scientific perspective, knowing is the result of doing - not thinking - so, running small experiments rather than making one terrifying, all or nothing jump (which I know a thing or two about) can make the transition not only more easily attainable, but feel safer.

Which is important. The idea that this is an “all or nothing” thing can leave you entirely paralyzed. But, what if you were to look at change as a longer period of transition, rather than a simple on/off switch? To this point, Ibarra suggests a period of “oscillation” - holding on to past work while also letting go of it at the same time - and living with the contradictions that introduces (as hard as that might be), rather than simply jumping to a premature resolution (which, in all likelihood, will result in either returning to the old path or a prolonged state of panic).

Subscribe now

The Real Question: Wholeheartedness, Not Rest

So, let’s recap: just because you’re good at it, doesn’t mean it’s right or your future; know when to quit and have criteria for doing so or else it really can be too late to fold; run a lot of experiments and don’t be afraid to straddle two (or more) paths as long as necessary.

But, what about “passion”? Or energy? Or, simply ensuring that the next thing doesn’t lead to more burnout?

David Whyte, the author and poet, exhausted running a nonprofit and privately wrestling with whether to leave, asked his friend the Benedictine monk Brother David Steindl-Rast to “speak to me of exhaustion.”

The monk’s answer: the antidote to exhaustion is not necessarily rest - it’s wholeheartedness. Whyte was tired because he couldn’t be wholehearted about the work he was doing. His whole heart was really in poetry.

So, what is it to be whole-hearted? Is your current work 25% of the way there? 50%? Something else?

To quote Whyte, “You are only half here, and half here will kill you after a while.”

Whyte writes that our sense of success in life can imprison us as much as our sense of failure. You can spend a lifetime defending a success rather than finding out who you actually are. For lawyers especially - a profession where identity fuses with work - burnout often signals not that a career change is inevitable, but that your relationship to law needs to shift.

The research bears this out. The ABA and Institute for Well-Being in Law reports that 36–44% of lawyers report depression, anxiety, or substance-use symptoms - often rooted in misalignment between their work and what they care about.

So, what can you be wholehearted about? Well, I think it’s less about what and more about when. We so often tell ourselves we’ll get to it when the kids are grown, when there’s enough money in the bank, when we’re retired…but, we need to ask what we are wholehearted about now.

That is the direction to which the change needs to pivot.

Identity Foreclosure: Why Professionals Burn Out

But, being “whole-hearted” is not enough on its own.

In Amy Wrzesniewski’s “Jobs, Careers, and Callings”, she found that people relate to work as a Job (financial necessity), a Career (advancement and prestige), or a Calling (fulfilling, socially useful work that’s an end in itself). Roughly a third fall into each.

She also noted that callings can turn sour - or, in other words - those most likely to burn out are those who narrate their calling as identity - “I am this thing” - so that when conditions make it impossible to live up to, the failure cuts at the self.

Take lawyers for example. For many (though not all) the profession is not just what you do, but what you are. When that kind of pressure falls on your work and career, and you aren’t doing it in a way that is wholehearted or in a way that meets your own self-expectation of joy, performance or satisfaction, that’s when things fall apart.

Psychologists call this identity foreclosure - a high commitment to a role reached through premature identification, without prior exploration or crisis. Hence, the need to experiment and try more things, along the lines of Ibarra’s thinking, while also, in Whyte’s thinking, pursuing those experiments that give to your heart the most - and allow your heart to express the most.

Is Burnout Different from Stress?

What about Mahjong?

Back to the table. In mahjong, the hardest hands aren’t the ones you clearly lose - they’re the ones you could still win, if the right tile falls, if you play it perfectly, if you’re willing to wait just one more round.

That’s the trap. Not the losing hand, but the winnable-looking one that ends up costing you the game.

Your career rarely hands you a clean signal to fold. What it offers instead is a question you can ask at any point, and the earlier the better: Am I still wholehearted here or just still good at it? You don’t have to answer by leaving. You answer by paying attention, by running the small experiment, by writing down the signals now so the sunk cost can’t talk you out of it later. The choice was always yours.

The only real mistake is waiting until it isn’t.

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.

→ Take the Beyond Success Assessment.

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

Subscribe now

I love summer camp.

Absolutely love it. Probably the best years of my life were at camp (don’t tell my family that).

I think you can have the most formative experiences of your life at camp. You make new friends, you discover new interests - you feel real independence without the gazing eyes of your parents. Camp truly is a magical thing.

And, the other thing that is magical about it is the community that arises out of the coming together of a bunch of kids (and a few adults) in a shared place.

What I mean by community is the shared sense of purpose, experience and meaning that can happen when a bunch of like-minded folks get together to work on common projects, share their own challenges amongst themselves, and utilize the individual and collective wisdom present to do greater things - in work and in life.

That’s what led me to create “Pursuers of More”.

Apply Now

Here is what we’ll do together in Pursuers of More:

• Bi-weekly open conversations, facilitated discussion, live group coaching, reflection

• An async space for intersession talk/accountability

• Homework (the good kind)

• A discounted 1:1 add-on if you want to go deeper

• Paid, with flexibility on pricing. I don’t want money to be the reason the right person stays out.

But above all, this will be about coming together to zone in on who you are, what you’re good at, how you’re moving - and, to where.

Today, 6/10 spots are full. It’s actually filling up, with exactly the kind of people I hoped would raise their hands.

Professionals who are excellent at what they do and quietly itching to do something 𝘮𝘰𝘳𝘦 with it.

People who are done pretending the question isn’t there.

And the best/strange part is: nobody’s in crisis.

Meaning: things are going well and something is still missing.

Which tells me two things:

1. people want this

2. you can put ideas out there sometimes and they just land - and you can really have no idea why.

If you’ve felt that and couldn’t quite name it, then maybe - just maybe - this is for you.

So yeah, that’s it.

There are a few seats left. If you think one of those is yours - click below to apply.

Apply Now

Still unsure? Take the Pursuers Assessment to see if it’s the right time for you.

Take the Assessment

And, if you think this will resonate with someone you know, please - share it.

Share

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.

→ Take the Beyond Success Assessment.

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

For many of us, there comes a time when we look at what we’re doing, and we wonder, “Really? This is what I chose for my work?”

And, the answer as you all know is, “Yes. Yes you did.”

It’s not like anyone forced you to do what you’re doing. No one forced me to be a lawyer (even though it is easy for me to say that someone did and then shirk all responsibility for not taking the path that would have been scarier and, more likely, more fulfilling).

No one forced you to do what you’re doing either. And, yet, if you’re here there is likely some sense that, maybe - just maybe - you’ve outgrown what you chose to do. The old you chose it, but now there is the today you - and the today you is thinking, “Meh.”

Now, let me be clear: choosing it wasn't a mistake. It probably gave you exactly what you needed for a long time. Outgrowing something is not the same as regretting it.

So, if you’re looking for some clarity here, then perhaps these 6 signals might sound familiar and might be inviting you into some bigger questions.

Subscribe now

You could do this job in your sleep — and increasingly, you do

You are doing your best work ever. Everyone is so happy with what you are delivering - you are a total rockstar. Promotions are guaranteed. 50% bonus? Yep. It’s yours. The most prestigious files? Of course - you are the one that gets them because you are the best.

And, you aren’t even trying.

You are, in fact, so detached from the work that you are just doing this on auto-pilot. There is, really, nothing in it at all for you besides a pay check. And, so, you keep delivering - excellently - because, despite you not caring at all about the work, you need to do it well to keep the job that keeps you fed (and, likely, then some).

This is a different beast of a trap, because in this scenario, there is no chance the bottom is going to fall out. It is all on you to make the decision to leave. Which is, of course, that much harder.

You’re excellent at your job - and - completely indifferent to it

The other side of this is that you simply don’t care how things turn out. You are apathetic. You couldn’t care less whether the client is happy or sad with the outcomes. You are happy to submit, let’s say, “less than optimal” work product. It doesn’t matter to you whether the company goes belly up in the next 6 months. In fact, you secretly, desperately hope that it does, just so that you don’t have to quit but can finally be rescued from what you likely already know is work that you are very much over.

Most people take this to mean that they have lost their mojo - they are just getting worse at the work, and so, they double down - more training, more education, more ways to refine their skills so they can get back to being really good at this thing that they don’t care about at all.

Does the lack of care and poor performance have anything to do with skill? Or, does it have everything to do with lack of connection to the work itself?

Your professional reputation is for work you no longer find meaningful

Or, this situation. You are the person that everyone goes to for a certain task. Let’s say it’s design work. Or, a specific area of law. Let’s say you are the only person who knows how to engineer a very specific type of garage door for über high-end homes. You have a clear dominance of the market, and, you are paid handsomely for what you deliver. You are good at it - and - you’re basically the only one who knows how to do it. If you stop doing it, someone else will jump in. You are known for this - your entire professional reputation is at stake if you stop doing what you are doing. You’d be crazy to give this up!

So, why do you want to give it up so badly? Clearly, there is no reason (at least on paper here) that indicates this would be the right choice. But, what if - yes, what if by some outside chance - you would be able to develop that same reputation, make just as good of a living, and - wait for it - feel deep, personal satisfaction - doing something else?

That last part is so often the missing ingredient for folks who are really good at what they do - it just so happens that they are really good at the wrong thing.

You close the deal, win the case, make the sale - and feel nothing

The Hedonic Treadmill. We all know it. It’s been talked about to death.

So, why do we keep doing it? Is it escapable?

I think so. Because, as soon as you really become aware of it, you start to realize, “Wait a minute. I’m not going to feel any better about my work, even when I land this next huge client/close this exhaustingly long term deal/finally get my long awaited Executive Producer credit?”1

And, then, once you know, you start to not do those things. You start to shy away slightly from the things that, even though you think are going to give you long term satisfaction, are hollow. They are shells of the things that once gave you much longer lasting joy. On the treadmill, every next hit gives you just that much less satisfaction because it’s hedonistic - it is pleasure pursuing only.

Is it possible for the “hits” to be things that really mean something to you? That aligned with your values? That lit you up in a way that was beyond simply making more money (despite, yes, the fact that we all need money and you can not simply put that aside and you can’t ask these questions unless you are at baseline safe in terms of finances), or, more reputational prestige, or more “more”?

I’d bet it would take less hits to feel satisfied - and, maybe, you could get off that treadmill for a bit.

Find Out What's Next

The version of you who chose this path no longer exists

Whoa, Jordan. Now you’re just going for the jugular.

Some of you might be thinking that. But, so what? Have you really not asked yourself this question in some other way?

For example:

“I liked this when I was younger, but now? Not for me.”

Or,

“This is not how I thought it would turn out when I was planning for my future.”

These are all variants on the same theme - namely - that there was once a person - who had the same name as you (maybe slightly different hair and face), but for sure, the same name as you, and they chose this path. They chose it knowing that, at some point, “today you” would be there. But, they didn’t really know “today you”. So, was it fair for them to choose it?

NO. NO IT WASN’T.

The problem is that they really couldn’t have known any better. They were doing the best with the information they had at hand. And, so, they decided.

Now, be that as it may, that doesn’t mean you are stuck with their choices. Because, “today you” is not the you of the past. That person is dead. Sorry. But it’s true.

So, you are free. You are free of the “you of the past” to make a decision. Sure, you will suffer some of the consequences of the decisions of “old you”, but you are also the only person who is in a position to make more changes that are an improvement on the decisions of “old you”. No one can do that for you.

Stop working for the dead you.

Share

What you actually want now would surprise the people who think they know you

Speaking of “the dead you” - how many people really know what the today you really would rather be doing?

How many times have you told the people in your life that you don’t really believe what you are doing is what you are meant to be doing any longer - and, that you believe you actually could do something else - something more meaningful and connected to you as a person?

Would they be shocked?

Maybe. But, you can’t know unless you actually tell them.

And, I’ll bet - especially for those people who really know you - they won’t be shocked at all.

When I decided to leave law, almost no one was shocked. In fact, one lawyer I know specifically called me to say, “So, you finally woke up!” It’s like he had been waiting for it.

And, that was a huge relief.

For two main reasons: 1. I realized that not only were people not disappointed in me making such a huge change, but were actually happy for me, and in fact, had secretly been hoping that one day I would know what they knew about me; and, 2. I realized that despite my best efforts, its really hard - in fact, pointless - to keep secret the things that we care about most - the things that we have longings for and wish that we could make real, if only the circumstances or timing or money or - whatever - were better.

The question isn't whether you've outgrown your career. It's how much longer you're willing to pretend you haven't.

Find Out What's Next

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.

→ Take the Beyond Success Assessment.

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

A person climbs Everest. A person runs a marathon. A person finishes a thesis.

In all cases, they have gotten somewhere.

Subscribe now

Except, in many ways, they feel like they haven’t gotten anywhere.

It’s a weird thing. The sense that, “Once I get to this place, then things will be better.” And, then you get there. And then things are not worse, but kinda the same.

Psychologists call this the “arrival fallacy”.

If you’re reading this at an hour you wouldn’t admit to, with a career most people would envy, here’s the first thing worth saying clearly: there’s nothing wrong with you.

You are paying attention. But, even with all you’ve achieved, you can’t really name - put a finger on - that weird sense of hollowness that is hanging around, even with all you’ve managed to do and make and be.

Keep paying attention. It’s information you are getting.

Let me tell you what it’s actually telling you.

Is it burnout, depression, or something else?

Making the distinction here is key, because, where you go from here really does matter.

First, Burnout. Generally speaking, burnout is a problem of load. Depletion as a result of answering demands beyond capacity. The usual (although not always) fix is rest. If two weeks off would fix it, it’s likely burnout.

Depression is a problem of capacity for feeling. Everything is flat - not just work, but the things you love, the people you love, the food you used to taste. It doesn’t discriminate and it follows you everywhere. This requires help. Therapy. If you are feeling this way, please, find a good therapist who can help.

There is, however, a third thing, and it’s probably the one that brought you here. Let’s call it misalignment. This is a problem of direction. You’re not depleted and you’re not numb - you feel things, maybe most sharply right after a win, when the feeling that was supposed to arrive doesn’t. And, performing better doesn’t seem to improve it. The problem is that you’re succeeding at the wrong thing, beautifully.

Misalignment is the only one of the three that achievement makes worse instead of better. If that’s the one that landed, keep reading. (If you’re genuinely not sure which it is, I’ve drawn the line more carefully here: How burnout takes away your MOJO)

Share

So, why does achievement stop feeling good?

There’s a mechanism underneath this, and understanding it takes some of the shame out of it.

Achievement runs on anticipation. So, when you finally “arrive”, it’s like a note in a song that is clearly. So, your nervous system starts hunting again for another song htat will, hopefully, sound better. Psychologists call it the hedonic treadmill; you’ve called it “okay, what’s next” so many times you stopped noticing you were saying it.

For most people, for most of life, this works. The treadmill turned you into someone formidable. The restlessness was an engine. But an engine in a car that doesn’t really know where it’s going just burns gas. It doesn’t do much else. At some point - usually after you’ve collected enough of the proof you thought you needed - the question quietly changes from can I drive there? to why am I driving there?, and the old engine has no answer for the second question. Because, engines generally don’t ask why.

So the emptiness isn’t a sign the achievement was worthless. It’s a sign you’ve outgrown achievement - the destination - as a reason. The problem is you can’t get to the next destination - your why - on the same fuel that got you here.

What Carl Jung understood about the second half of life

A hundred years ago, Carl Jung drew a line through the middle of a life, and almost nothing has described this feeling better since.

The first half, he said, is for building the ego - the career, the credentials, the social self, the persona you present to the world. This is correct and necessary work. You’re supposed to do it. You’re supposed to find out what you can achieve, who you can become in the eyes of others, what you’re capable of carrying.

But somewhere around the middle, the task inverts. The second half of life isn’t about adding more to the structure you built - it’s about asking who’s been living inside the structure itself. Jung’s word was individuation: the slow, often disorienting work of becoming who you actually are, underneath who you were rewarded for being.

Here’s why this matters for you: the emptiness you feel is not the absence of success. It’s just the first signal of the shift that is happening - that in the second half of life, what worked in the first half - what you strived for - just doesn’t give the same rewards. And, the part of you that the structure couldn’t account for in the first half is now asking for it’s turn behind the wheel.

Most high performers misread this signal completely. They assume the emptiness means they need a bigger first half - more achievement, a harder goal, more wins. So they double down on the exact strategy that produced the emptiness, and wonder why it deepens.

This, of course, doesn’t work. Because it’s not honest.

Take the Free Assessment

What to do when the feeling won’t go away

So, what do you do?

Be more honest. Particularly, with yourself.

Now, here’s the part where most articles hand you a list of affirmations. I’m not going to insult you with that, because you’ve likely already tried the things that fit in a list, and you’re still here.

What this actually requires is harder and simpler: you have to stop optimizing the structure and start questioning it in a way that produces an actual decision you can act on.

That means doing three things you probably haven’t done, because until now, you never really had to:

Name the “borrowed goals”. Which of your ambitions did you actually choose, and which did you inherit - from a parent, a mentor, an industry, a younger version of you who needed to prove something?

Separate your identity from your output. Ask yourself who you are at 8pm on a Sunday, when no one is evaluating you and nothing is due. If that question makes you uncomfortable, that discomfort is the work. The enmeshment of self and performance is the specific knot the second half of life is trying to untie — and it’s deep enough that I gave it its own essay on untangling identity from career.

Distinguish a real decision from endless rumination. Most smart people don’t have a clarity problem — they have a too many possibilities and no framework problem. The mind alone can’t resolve this, because the mind is the thing that’s stuck. You need an external structure and, often, another person who has stood where you’re standing and isn’t afraid of the question.

That last point is where I do my work.

A place to start, when you’re ready

If the misalignment description fits then you don’t need years of self-help. You need focused clarity, a framework for thinking it through, and someone in your corner who’s been there.

That’s exactly what I do, and every engagement begins the same way: with a Free Coaching Call. It’s a candid, no-pitch conversation about where you are, what’s not working, and whether coaching is even the right move for you right now. And, if it’s not, I’ll tell you.

Book a Call

Not ready to talk yet? Start with the Beyond Success Self-Assessment — a short, free diagnostic that tells you whether what you’re feeling is burnout, misalignment, or something else, and what the next move actually is. It takes about ten minutes and you’ll have a clearer read on yourself by the end of it.

Frequently asked questions

Is it normal to feel empty after achieving a major goal? Yes — it’s one of the most common experiences high achievers don’t talk about. The striving generates the feeling of momentum; the arrival doesn’t sustain it. A brief flatness after a big win is normal. A persistent emptiness that deepens with each new success is a signal of misalignment worth examining.

How do I know if it’s burnout or something deeper? Burnout responds to rest — time off restores you. Misalignment doesn’t; it often gets worse with more achievement, because the problem is direction, not depletion. If genuine rest hasn’t touched the feeling, it’s likely not burnout. If the flatness covers every part of your life and won’t lift, speak with a mental health professional.

Can you feel unfulfilled in a career you’re good at? Absolutely — being good at something is one of the strongest reasons people stay and one of the weakest reasons to. Competence and fulfillment are different things. Excelling at work that no longer fits you is precisely the trap that produces this kind of emptiness. (More on this: signs you’ve outgrown your career.)

What is individuation in simple terms? It’s Carl Jung’s term for the work of the second half of life: becoming who you actually are, underneath who you were rewarded for being. The first half builds the outer structure — career, status, persona. The second asks who’s been living inside it.

Should I quit my job to find purpose? Usually not as a first step. The clarity has to come before the exit, or you risk leaving one misaligned situation for another. The more useful sequence is to understand what’s actually misaligned, then decide what changes — which may or may not mean quitting. I’ve laid out the right order here: should you quit to find purpose, or find purpose first? And if you’re already past the question and wondering what’s on the other side, start with what comes after success.

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.

→ You can get in touch with him by email or at his website.

→ Take the Beyond Success Assessment.

→ Check out real live coaching sessions.

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

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).

Share

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.

Subscribe now

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.

→ You can get in touch with him by email or at his website.

→ Take the Beyond Success Assessment.

→ Check out real live coaching sessions.

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

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.

Subscribe now

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.

Share

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.

But, if you need some help…

→ Take the Best Next Move Assessment here.

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

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.

Subscribe now

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.

Share

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…

→ Take the Best Next Move Assessment here.

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

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).

Subscribe now

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.

Share

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

And, if you want to, you can…

→ Connect with me on LinkedIn.

→ Take my free Next Best Move Assessment.

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

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.

Subscribe now

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.

Share

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.

→ Connect with me on LinkedIn.

→ Take my free Next Best Move Assessment.

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

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.

Share

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.

Subscribe now

The professionals I work with know this feeling

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

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

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

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

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

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

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

What I know to be true

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

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

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

Here’s what I want to know

Not rhetorically. Genuinely.

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

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

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

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

→ Take the Best Next Move Assessment here.

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

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

You’re good at what you do.

Actually - you’re probably really good at it.

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

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

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

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

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

The Taxonomy You Never Heard Of

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

The levels, simplified:

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

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

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

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

Where Most Professionals Get Stuck

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

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

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

Then competence arrives.

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

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

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

The Stages of Competence

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

Here’s how it basically looks:

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

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

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

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

The Connection Between Learning and Meaning

Turning back to Bloom’s Taxonomy.

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

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

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

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

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

That’s the dissociation people mistake for burnout.

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

Climbing Again

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

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

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

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

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

What does that look like?

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

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

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

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

→ Take the Best Next Move Assessment here.

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

“But, I already have a therapist.”

I hear this a lot.

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

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

From my end, both are worth taking seriously.

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

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

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

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

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

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

1. left legal practice

2. started a legal practice

3. pursued art, film and other things

4. gotten married

5. had children

6. left law again

7. do what I do now

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

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

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

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

Well, yes. In a way.

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

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

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

Here’s how1.

Share

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.

Share

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.

Share

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.

Subscribe now

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

But, it still stings.

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

It had.

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

And, they had rejected my proposal.

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

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

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

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

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

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

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

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

But this isn’t law anymore.

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

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

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

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

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

→ Connect with me on LinkedIn.

→ Take my free Next Best Move Assessment.

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

I have always loved magic.

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

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

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

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

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

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

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

And so, most don’t fool them.

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

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

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

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

And yet.

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

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

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

That’s what we do, isn’t it?

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

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

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

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

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

Jared Kopf was performing.

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

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

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

And he was extraordinary.

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

He had become something.

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

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

But it was different this time.

It had shifted from envy into something closer to awe.

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

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

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

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

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

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

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

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

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

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

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

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

It was a man who had become something.

That’s the whole game.

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

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

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

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

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

Leaving law does not answer the question underneath the question.

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

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

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

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

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

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

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

What is it pointing at?

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

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

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

→ Connect with me on LinkedIn - I share more thoughts like these there.

→ Take my free Next Best Move Assessment.

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

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.

→ Connect with me on LinkedIn - I share more thoughts like these there.

→ Take my free Next Best Move Assessment.

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