Breaking free from a life that doesn’t fit

A story of pain, purpose, and redemption [The Other Side of Enough: Interview #3]

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The Way of Work explores stories of where we fit in the world of work. This is part of the new series, The Other Side of Enough, exploring what life is like when you have enough to never work again.

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What happens when the purpose we’ve pursued our whole life starts to feel like someone else’s dream?

Jordan Grumet had a clear purpose early in life: he wanted to be a doctor, just like his father. It fueled his childhood and early adulthood, creating a vision of who he could become.

But was this his purpose?

Fast forward to today, Jordan is doing very little doctoring and is instead thriving as an author and podcaster. He’s financially independent, having reached his version of “enough,” but he still works about 40 hours every week on what he wants.

What happened in between? From fulfilling his purpose as a doctor to living life as an independent creator?

This is a powerful story of how early signs of purpose can serve us so well, but potentially lead us astray.

But rather than leaving us with more questions, Jordan comes bearing answers to the riddle of how to get to the other side of enough. Through his own journey and research, he has landed on (in my humble opinion) the core challenge that so many of us face: we want to feel purpose in our lives, but rarely seem to grasp it. He’s got an idea how to fix that, and his own story shows us how.

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Purpose forged in pain

“Purpose” can sound like such a positive, pleasant word. But sometimes its origin can be bitter and brutal. For Jordan, the birth of his purpose to become a doctor, began as dark and disastrous as it comes:

“When I was 7 years old, my father died suddenly. He had a brain aneurysm. He was a doctor. He was literally rounding at the hospital when he got a severe headache and collapsed. Taken down to the emergency room.

Within a day or two, they said ‘he's brain dead. We need to remove all the life support.’”

How he processed this event would define the next few decades of his life. 

“At the age of 7, I very much thought it was my fault, like 7 year olds tend to look at the world through their own lens.

And so I really struggled with feelings of enough, of being a good enough kid.

But I eventually came to the conclusion that the way to fix this cosmically bad thing that happened to me was to become a doctor like my father. Literally, walk right into his shoes.”

He admits that this purpose gave clarity to his life, where he could funnel his effort and ambition.

“And this is what I'm gonna do. And it actually very much filled me up.

This feeling of being meant to be a doctor carried me through college, medical school and residency, and then, becoming that doctor. I always dreamed of it. And it was very purposeful.

I really did embrace that identity until I was practicing for a number of years. When I realized: I don't love this. It doesn't feel like me.”

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When purpose turns against you

While the shadow of this purpose was initially a guide, it later became a weight he’d carry into adulthood. He describes one of the defining nights of his career—the moment he realized his dream of being a doctor might not be what he had imagined.

“I can tell you the exact moment. My second year of residency, I was alone at night in the ICU (Intensive Care Unit), taking care of deathly ill patients.

We had a patient get more and more short of breath, and I had to intubate them, put the tube down their throat. And I struggled to do it, and the anesthesiologist never came, and finally we got the patient intubated, but they died quickly after.

Then, I had to tell this person's family that he died. By myself, a second year resident, at 2:00AM, sitting at a table with 10 family members. And then the next morning, I had to get on the phone and talk to 3 separate daughters and tell them that their parent died.

I remember just the utter devastation of that. That was the beginning of what eventually would be a decade or two of burnout, of dealing with these situations that were incredibly difficult, not really feeling that payoff, not feeling like I was helping people, being inundated with paperwork and menial tasks that didn't seem important, and not feeling like this was who I was really meant to be.”

What he had long called his purpose began to feel like something else—a mask, perhaps, or a heavy burden he was carrying. That unsettledness would stay with him for years to come.

“So it started on that night, but it was a slow, burning process that changed me, that turned me into kind of a cold, unhappy person.

In the process of coming out of that, after having kids, starting to feel me again, and starting to kind of heal from some of that trauma, I just started to realize, look, this is not the thing that I think I was meant to do, and it's no longer fulfilling me.

And so the most natural question was: ‘how do I get out?’”

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Letting go of the legacy

Stepping away from being a doctor must be a difficult thing to do. It’s a profession with a respected social identity, strong community, and a healthy income.

But what if you were not only walking away from being a doctor, but also walking away from what connected you to the memory of your dead father?

“All of a sudden I had to confront all these issues of stepping away from a sense of purpose and identity, and a connection to my father… the only things I've ever known.

And so what does that mean? Who am I? If I step away from this thing that I've spent my whole life becoming?

I had to start saying, ‘what does enough look like? What's enough money? What's enough life? What’s being enough of a person?”

Many of us are so focused on our career goals or financial milestones that we rarely stop to consider a more fundamental question—what will be enough?

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Peeling away an old identity

The process of dissolving his old identity wasn’t quick or easy. Layer by layer, Jordan set down pieces of himself that no longer felt like him.

“It took me a long time to come to terms with this idea of not being a doctor, and I slowly got rid of things I didn't like doing. I had a private practice. I eventually got rid of that. I didn't like working nights and weekends. I was working in nursing homes. I got rid of that.

[Over about 4 years] I'd gotten rid of everything but hospice work. That was something I really enjoyed and loved doing, and so I knew that that felt like part of my new identity as opposed to my old. So I kept that.”

By subtracting parts of himself that didn’t work, he created the space to add back parts that did.

“I got rid of a lot of things that were taking up my time. And so I now had 40 hours a week to do whatever I wanted. And I realized they were these things that I always wanted to do or always fit into little cubby holes of time, because I never had enough time. Things like writing or public speaking, which eventually became podcasting.

I loved doing all these things, but I never gave myself permission to spend time doing them. So now I could.”

Rather than being new endeavors, writing and speaking were “something that was always a part of me.” Reaching enough just enabled him to add them into his life, eventually becoming his new purpose.

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The mirage of money

Along with the topic of purpose, Jordan spends a lot of his time talking about money. Despite having reached financial independence himself, he thinks its pursuit should not be our primary focus.

“Most of us set up money as our main goal, instead of a tool. And so we put all of our energy into making money, and then we get there and then have to confront the fact that we never thought about what we actually wanted to use that money for.

So a big part about things like purpose and enough is to really try to get people to realize that we're getting the order wrong.

We're building a financial framework and getting to financial independence. And then we're trying to decide what purpose looks like in our life.

[Instead,] we should start with purpose, identity, and connections. Really dig deep into those and then build a financial framework. Unfortunately we don't. And so we hit that cliff. When we figure out our finances and realize that we didn't invest in purpose, identity, and connections which are ultimately, I think, what leads to happiness.”

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Prioritizing the right purpose

We all know that purpose is important. And while the world may tell us how to find it, for some reason we can’t seem to grasp it. Jordan has an idea why:

“The studies are really clear. Purpose in life is associated with health, happiness, and longevity.

On the other hand, up to 90% of people get what's called ‘Purpose Anxiety’ at some point in their life. The search for purpose is daunting, makes them anxious, makes them feel depressed, and they don't feel good about it.

So there's a paradox: how is purpose both the most important thing, as well as incredibly anxiety provoking?”

Reflecting on his journey and backed by research, Jordan uncovered a valuable insight: not all purpose is the same. He distinguishes between two types of purpose:

“I named the bad one, big ‘P’ Purpose, and the other one little ‘p’ purpose.

Big ‘P’ Purpose is the kind that makes us feel stressed and anxious. It is usually very goal oriented. And it's usually very big and audacious. We have these huge ideas of changing the world like curing cancer, becoming president, flying to Mars, being the founder of a $1B company.

All of those things we're programmed to think should be our purpose. If you can dream it, you can build it. We've been taught this. It's the American ethos, and it gets plunged into our head through marketing, TV, and social media, etc.

The problem with that is that goal-oriented purpose, especially when it's big or audacious, you generally don't have agency to achieve it. Instead, you have to be the right person, at the right time, saying the right things, with a lot of luck, and maybe the right genetics.

And the truth of the matter is 99.9% of people won't have that. And so if [your purpose is] goal-based and it's one of these big goals, most likely you're going to end up disappointed.

This is a very scarcity-oriented version of purpose. It's win or lose. All or nothing. Winner takes all. There can only be one president at a time. So everyone else loses. So that's probably gonna leave you feeling pretty lousy.”

Right now, some of you might be wondering: wait, how can purpose be anything BUT goal-oriented and ambitious? There’s no other kind!

Well, Jordan makes an important distinction, with an insight I have found true for myself:

“Contrast that to little ‘p’ purpose which doesn't worry about goals as much, but it's much more interested in process. This is very abundance-oriented.

How many things can you do that you enjoy doing? Well, they're countless.

And once you stop worrying about the goals and just enjoy doing what you're doing, it becomes so much easier. So it's not winner-takes-all. It's not all-or-nothing. It's kind of like all-or-all. Everyone can do this. Everyone can succeed. There's no such thing as failure.

Little ‘p’ purpose becomes a really good way of spending my time in such a way that I know it's fulfilling. And I'm not just waiting on some goal that I might or might not get to.”

This is why Jordan backed away from the big purpose of being a doctor, a purpose that seems extraordinarily worthy, but ultimately not for him. And it’s why he leaned into writing and podcasting, not because they were audacious or bold or another fill-in-the-blank “should” that comes from other people. But simply because he enjoyed the act of doing them, not being them or the outcome they could achieve.

Can we redefine purpose—not as a distant goal but as a daily practice that offers fulfillment, without requiring perfection?

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Rewriting the legacy

I want to end with a thought exercise:

What kind of purpose do you think Jordan’s father would want for his son?

The one that made him feel eternally indebted and never enough? Or the one that lights up his soul; that energizes, enriches and fulfills his every day?

Jordan’s journey reminds us that purpose doesn’t always look the way we imagine. For much of his life, his sense of purpose was tied to big, almost mythic aspirations of fulfilling his father’s legacy (and maybe even an attempt to rewrite the past). The goal was grand, even noble, but also impossible to achieve.

“And so I see this in my own life all over the place. My big ‘P’ Purpose was saving the world because my dad died and I couldn't save him. So I was going to become a doctor and save everyone else.

You know, it was just too hard. I couldn't save everyone else, and a lot of times I was just disappointed.

On the other hand, there are all these versions of little ‘p’ purpose that fill me up and make life a lot better. Like I love podcasting and every time I get in front of my microphone and get to interview someone, I lose myself. I lose track of time.

It's worthwhile, even if no one ever listens to that episode. So the goal doesn't matter. It's the doing that's really exciting.”

In the end, I like to think that Jordan’s father would be proud of his son’s path to his own purpose.

His story shows us that sometimes, when we let go of striving endlessly for an ideal we can never reach, we can discover something richer: a life full of meaning that matters just as much, if not more.

Special thank you to Dr.

Jordan Grumet

for sharing his story. He agreed to not be anonymous. To learn more about Jordan’s work:

• Preorder his upcoming book: The Purpose Code: How to unlock meaning, maximize happiness, and leave a lasting legacy

• Check out his first book: Taking Stock: A Hospice Doctor's Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life

• Subscribe to his newsletter:

  The Purpose Code

This interview was transcribed, then summarized and edited for clarity; any emphasis is mine.

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Bonus Questions

What are resources that have helped you in your transition?

• The White Coat Investor, by Jim Dahle

What has been your best purchase, since hitting enough?

• Yearly vacation with his kids to Mexico

What has been your worst purchase, since hitting enough?

• Whole life insurance policy

Before & After - on a scale of 1-10 (10 being best), how would you rate the following before and after enough:

• Health: 6 → 8 (+20%)

• Stress (10 is low stress): 1 → 8 (+70%)

• Creativity: 6 → 10 (+40%)

• Relationships: 8 → 9 (+10%)

• Impact: 7 → 9 (+20%)

• Meaning: 5 → 10 (+50%)

• Work Hours/Week: 60 → 40 (-20%)

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This is part of the series, The Other Side of Enough, exploring what life is like when you have enough to never work again.

Intro: The Other Side of Enough

Part 1: Everywhere But Home: The search for belonging after reaching financial freedom at 32

Part 2: Expectations Never End: Finding freedom after enough

Part 3: Breaking free from a life that doesn’t fit

Part 4: Will you get what you want, after reaching financial independence?

Part 5: Waiting Decades to Finally Follow Your Dreams

Part 6: After ‘Happily Ever After’