Starting a new dream: how I navigated a mid life career change and found my path in my 30s (and a few practical tips on finding yours, too).

Note: This article picks up where the 2016 article, “Letting Go of a Dream: Why I left Professional Speaking” leaves off.


April 2015, Washington DC: I’m getting ready to go out to a trendy U-Street bar where the drinks are too expensive, the lights are too dim, and the music is too loud. Nice watch, rolled sleeves, a few days of stubble, cologne, stylishly messy hair – you know the drill.

I’m blasting LCD Soundsystem as I get ready. Without warning, one of the lyrics seizes my attention and doesn’t let go:

“If you’re afraid of what you need / look around you / you’re surrounded / it won’t get any better.”

The epiphany stabs me in the heart: my life is off track. Not just that, but I’m quietly miserable and afraid of trying to change. Regardless, the pain I’ve denied for years is suddenly and vividly undeniable.

My speaking career gives me everything I thought I wanted – money, status, standing ovations, photo ops, world tours, and more access than anyone should give me.

I’ve been working towards this for 23 years. I first stood in front of a small crowd to do magic tricks when I was six. Now I stand in front of large crowds to give speeches. Am I really expected to give this all up, everything I’ve worked my whole life for, if I want to be true to myself?

And by the way, who the fuck am I to want more from life? As far as I can tell, almost everyone has it worse than me. I have no right to be miserable. Who am I to acknowledge the pain that I feel, let alone believe I’m worthy of being free of it?1  

I don’t know what to do with all of this, so I meet up with my girlfriend and go to the bar while trying to ignore the unignorable.


I never chose to be a working magician as a child. Someone else knocked over the first domino without asking me. Everything else in my professional life was just inertia and it never occurred to me that I could stop the chain reaction. I spent 23 years on stage. Twenty-three years of work. Honestly, until that moment listening to LCD Soundsystem, it never occurred to me that I’d want to do anything else. Now I understand that I have to make a change if I want to be happy in my work life.


The next year is a blur: I leave my life in DC, travel for a while, move to Denver, start this blog, quit touring, get a tattoo, and work as a consultant and coach to make ends meet.

I am lost.

But at least I know I am lost.


Fall  2016: I’m on a silent retreat at an ashram hidden away in the Rockies when it hits me: no amount of meditation, self-help, or Tony Robins bullshit has managed to solve the persistent psychological problems in my life.

Anxiety and depression are always lurking in the shadows. And despite my best efforts, my walls prevent me from really letting love in. I promise myself that when I get home, I’ll book an appointment with a therapist.


Booking the initial appointment required wrestling with tons of shame and resistance. I’m so glad I overcame it. My therapist, P*, was a Godsend. I worked with her for three years and in a very real way, she gave me my life back.

Healing and finding a stable sense of happiness and self-worth was such a profound and unexpected experience that I wanted to help others the way P* helped me. I knew how to build business and didn’t want to go back to school, so I started flirting with a crazy idea: raise capital and open a chain of boutique mental health spas.


Spring 2018 part 1: It’s all a manic blur as I start to build the mental health spa business. Jet planes, investors, clothing that makes me look way hipper than I really am, conversations about fancy scotch with fancy people, and an endless tornado of meetings.

We need a few hundred thousand dollars and angel investment. Somehow I assemble a team of investors.

Oh, shit. I made a big mistake. We need $2.3 million and venture capital.2 I explain my error to the lead investor. I’m sure he’ll pull the plug. There’s no way we can pull that number off. A few days later he calls…

…We can pull it off.

Somewhere amidst the blur, my Dad mentions, “You know, I’m not sure that making a lot of money is motivating for you. You’ve had chances to do that, and you’ve always chosen other things. If you take on investors, you have to focus on money. And I’m not convinced that you’d like the high intensity and unbalanced nature of running a venture backed startup. You cherish your life outside of work.”

I file that under #parentsjustdontunderstand.


Spring 2018 part 2: I’m at the gym talking to G*. G* used to be a professional athlete. Now he’s back in school studying to become a psychologist.

I ask, “What’s it like to leave sports and go back to school?”

“Ya. It’s fucking hard. But here’s the thing: if I don’t make changes, then this is as good as it gets. It’s flashy to be an athlete but it doesn’t last forever. And it’s not really me to be honest. I want to be a psychologist. It’s kind of simple.”


Spring 2018 part 3, several weeks later: I’m back at that ashram and it hits me just like that LCD Soundsystem lyric: My Dad is right. G* is right. I don’t want to build this mental health spa, become beholden to investors, and work adjacent to mental health.

I want to be a clinician. I want to roll my sleeves up and work with a small group of clients to help them transform their lives the way P* helped transform mine.

This is hard to accept. I don’t want to go back to school. I don’t want to let my investors down. I don’t want to give up the status that my work as a speaker, consultant, and (almost) founder conferred upon me. I don’t want to trade my big dreams for smaller ones.

And yet…

I know what it’s like to ignore my heart. I’ve done that for most of my life. It will be jarring to stop the fast-falling dominoes, but I think it’s the only way for me to be truly happy.


Winter of 2018: I accept a spot in Fordham University’s accelerated Master of Social Work program. I am going to become a therapist.


March 2021: I’ve been working as a clinician for about a year (2.5 if you count my internships).

I’m at the beginning of a new dream and, holy shit, do I love it. I never knew it was possible to adore your work.

Switching from something I was an expert in but disliked to something that I’m a novice in but love was one of the hardest decisions I’ve ever made. It was also one of the best. 

For the past year I’ve been working by referral only and keeping my caseload small. There’s been a lot going on in the background:

  • Tying up loose ends from the old businesses before closing them
  • Completing the first two phases of licensure
  • Obtaining a shit ton of post grad training3
  • Completing a 2.5-year meditation teacher training
  • Finding an excellent consulting therapist to study under
  • Finding an excellent consulting meditation teacher to study under
  • Rethinking the direction of this blog
  • Moving to a new apartment
  • Developing the marketing for the therapy practice4

With most of the above either complete or nearing completion I am officially opening the (digital) doors to new clients. If you or someone you know in the State of Colorado needs a therapist, I’d love to chat. If I’m not the right provider, I’ll do my best to connect you with someone who is. You can learn more about working together here. And if you’d like to receive notifications for upcoming classes, groups, meditations, and in person events (when the world allows) you can sign up for my newsletter here.

PS: A few tips for finding your path

For those of you who are also searching for your path, I want to share a bit about what I learned along the way. A note here: my path, admittedly, was long, winding, and chaotic. It is not always like that.

1) It’s basically guaranteed that you’ll have to do a bunch of shit you don’t want to.  The last thing I wanted to do in my early 30s was leave an extremely high-status, lucrative job so that I could become an unpaid, poorly-treated intern. And yet, that was the only way forward. In most cases, if you aspire to make a significant change, but have been struggling to, you’ll eventually realize that getting from A to B requires doing things you’d rather not. With the advantage of hindsight I can tell you this: it was 100% worth it. And I expect it will be for you too. 

1.5) You may also have to face your fears. If there’s something you’ve been yearning to do, and you’re not held back by some form of systemic oppression (and far too many are), then there’s a good chance you’re being held back by fear. That was the case for me. At some point, the only way to grow is to strategically lean into those fears. If this is the case for you, go gently and slowly. But also, go forward. 

3) Your inner child may have a pretty good idea of what you should do with your life. When I was 12, it was so clear to me: I wanted to be a therapist. But the dominoes of being a magician kept falling and the inertia swept me away. It took years to recall who I really was.

I only remembered my childhood dream after I started grad school. However, you may be able to speed up the process by thinking back to your childhood ambitions. Even if they’re not on the nose, they may lead you in the right direction.

4) Most people will give you bad advice. In the beginning I talked to everyone about how to figure myself out. With time, I noticed that most people were thinking about the problem incorrectly. They weren’t asking, “What is the best move for Jason?” They were asking, “If I were in Jason’s shoes, what would be the best move for me?”

  • The friend who never went to college but was successful told me education was a waste of time and money
  • The friend who works as a coach but has no formal training in psychology or mental health told me that education and licensure doesn’t matter (he’s dead wrong about that, by the way)
  • The friend who has been lost forever told me that finding your path is a myth
  • The friend who runs a venture backed startup told me I’d be insane to walk away from my investors

Eventually, I noticed that only my deep inner circle took the time to ask, “What would be right for Jason?” After I understood what was happening, I stopped talking to everyone else. I needed the silence and skilled perspective to get clear.

5) Put a bit of thought into your overall life strategy. There are a handful of jobs I think I would love as much as I love being a therapist: hospital administrator, chaplain, and fruit vendor on the Pacific coast of Costa Rica (genuinely) among them.

But the path forward with these careers are tough. There is a far greater supply of administrators and chaplains than there is demand. Moving to Costa Rica to sell fruit would require too much sacrifice across too many spheres. Working as a therapist threads the needle better than anything else. It helps people, it’s interesting, I love studying it, and it fits neatly into my personal and social life. Is it everything to me? Not really. I miss the chaos and adrenaline of speaking, and I still feel that void. But even so, I’m far happier in my career than I imagined possible.

And to get ahead of a tricky conversation: not everyone’s path will lead them to making money. If you realize you’re in this position, I urge you to ask the question, “How can I do both?” In many cases, the answer is some version of: take a generic job that leaves you with enough time and energy to pursue the things you love.  

6) Allow yourself to be slow, messy, and playful. I put a lot of pressure on myself to ace my quarter life crisis (or is it a mid-life crisis? Let’s pretend I’m still young enough for it to be quarter life, ok?).

In hindsight, some of that pressure served me; I’m glad I worked my ass off and finished my masters in half the amount of time it normally takes.

But most of the pressure did not serve me.

For a while, I had no idea what I wanted to do with myself. Instead of embracing my inner bohemian, it felt important to catch up with everyone else.

As mentioned above, I seriously considered working in hospitals as a chaplain or administrator. To see if it was right for me, I shadowed contacts who worked in the field. Instead of luxuriating in the beautiful chaos and manic logistics of hospitals and healing, stress made me narrowly focused on whether or not this career made sense for me. I missed the forest for the trees.

While I am ecstatic about where my path has led me, I wish I slowed down to enjoy the scenery. For those of you searching for your path too, I hope you learn from my mistakes. I hope you sink into the experience of being in between things and trust that with time and persistence, you’ll figure it out (though I know this is easier said than done).


  1. Looking back there were two dramatic flaws with my logic here. First, pain is pain. Full stop.

    Yes, there is a horrifying amount of systemic oppression in modernity. Working to overturn the straight white male supremacy is a singularly important task. But this isn’t done by denying your pain. This is done by healing your pain. Real health highlights a critical truth: we belong to one another.

    Second being true to ourselves often makes us better equipped to help others, not worse. Though I make less money and have less time now than when I was a consultant, I give away more of both. I’m not plagued by the sense of scarcity and lethargy that gripped my life when I was off course. I am also far better equipped to help others as a licensed therapist and meditation teacher, than I ever was as a speaker / consultant. At first glance this may appear to be unique to me, as I moved into healthcare. In practice though when we heal and become truer to ourselves, we naturally start caring about others more. We can’t help it. 

  2. You know how pop culture makes it seem amazing to be a young, funded entrepreneur on the bleeding edge of your industry? Ya. It’s not like that at all. If I accepted the investment my salary would be somewhere around $40,000 / year for the first few years. And I wouldn’t own the company anymore either; the investors would take a considerable amount of control and ownership. Along the way I would be expected to work at least 60 hours a week for years. This type of arrangement is borderline abusive. It’s also the norm.
  3. Fun (and exhausting) fact: since graduating a year ago, I’ve accumulated nearly 150 post grad / continuing education credits. To put that in perspective, my master’s degree required 66 credits.
  4. One huge problem with therapy – in addition to it being cruelly stigmatized – is that most therapists have horrible marketing and business practices. This makes things worse for everyone. My aim is to buck that trend from the get-go. I hope you like the new site!

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