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Last Thanksgiving, my dad and I were sitting on his back porch, and he was telling me about a new supplier he’d found for his shop. He was genuinely excited. Not startup-pitch excited. Not Series-A excited. Just… quietly, deeply engaged in a problem he’d been solving variations of for three decades. And something shifted in me that I’m still processing months later.

I looked at him — 67 years old, same business, same town, same routines — and for the first time in my life, I didn’t feel an ounce of pity. I felt envy.

That’s a weird thing to admit when you’ve spent your entire adult life building the opposite. I sold my first company at 27. A mobile app for small business appointment management. It wasn’t a massive exit, but it was enough to make me feel like I’d outgrown my father’s world. Like I’d cracked some code he never had the ambition to try.

I was wrong. Spectacularly, embarrassingly wrong. And it took a failed startup, deep debt, a relationship that fell apart because I was emotionally unavailable, and about fifteen years of therapy to understand why.

The story I told myself for twenty years

In my twenties, I had a narrative about my dad that felt airtight. He was a good man who played it safe. He had talent — the guy can fix anything, talk to anyone, solve logistical problems that would make most people’s heads spin — but he never “went for it.” He never scaled. Never hired a growth team. Never pitched investors. He just… ran his business.

I genuinely believed ambition was binary. You either had it or you didn’t. And the evidence of having it was constant expansion, constant disruption, constant movement toward something bigger. My dad’s contentment looked like stagnation to me.

Here’s what nobody tells you about that mindset: it’s not actually about ambition. It’s about identity. I needed my father to be the cautionary tale so that my choices — the risk, the chaos, the burnout — felt justified.

Psychologists have a term for this. Research on self-enhancement motivation shows that we routinely construct narratives about others — especially parents — that protect our sense of self. We don’t just compare ourselves to people. We need certain people to be less than us so our own trajectory makes sense.

My dad wasn’t my inspiration. He was my foil. And I didn’t even see it.

What actually happened when I chased “more”

After selling the first company, I immediately started another one. Eighteen months later, it was dead. Investor money gone. I was in deep debt, gaining weight, not sleeping, not exercising. I’d lost my girlfriend because I couldn’t be present for a single conversation that wasn’t about runway or burn rate.

I traveled after that. Rural Thailand. Mexico. I told people I was “finding myself,” but honestly, I was hiding. I’d built my entire identity around being the guy who was going somewhere, and suddenly I was the guy who’d arrived at nowhere.

You know what my dad did during that period? He kept running his business. He fixed a drainage issue in his shop. He renegotiated a lease. He went to my cousin’s wedding. He lived his life.

At the time, I remember thinking: must be nice to not care about anything bigger.

God, the arrogance.

The psychology of “enough” — and why we can’t see it in our twenties

There’s a concept in psychology called the hedonic treadmill — the idea that we adapt to improvements in our circumstances and return to a baseline level of happiness regardless of external gains. It’s well-documented. But there’s a related and less-discussed phenomenon that hit me harder when I finally encountered it.

Research by Kennon Sheldon and Sonja Lyubomirsky on sustainable wellbeing found that people who pursue intrinsic goals — things like personal growth, community contribution, and meaningful relationships — report significantly higher long-term life satisfaction than those chasing extrinsic markers like wealth, fame, or status. Not marginally higher. Significantly higher.

My father, without ever reading a psychology paper, had been living this for thirty years. His business wasn’t a failure to scale. It was a vehicle for exactly the kind of engagement that research consistently links to deep satisfaction: autonomy over his days, mastery of his craft, and genuine connection with the people around him.

Sound familiar? It should. That’s basically Self-Determination Theory, developed by Edward Deci and Richard Ryan — the framework showing that autonomy, competence, and relatedness are the three core psychological needs driving human motivation and wellbeing.

My dad had all three. I had none of them during my “ambitious” years. I had external validation, anxiety, and a really expensive watch I bought to feel like I was winning.

7 things I finally understand about my father’s choices
1. He wasn’t avoiding risk — he was managing it differently

Running the same small business for thirty years isn’t the absence of risk. It’s a continuous, daily negotiation with uncertainty — suppliers, customers, weather, recessions, pandemics. My dad survived 2008. He survived COVID. He adapted constantly. He just didn’t need to narrate his adaptation on Twitter for it to count.

2. He chose depth over breadth

I used to think pivoting was a sign of intelligence. Sometimes it is. But my dad’s decision to stay in one domain for decades gave him a depth of knowledge and relational capital that I’ve never come close to in any single venture. His customers trust him in a way that no amount of growth-hacking can manufacture.

3. His identity wasn’t contingent on external markers

This is the one that gets me. After my first exit, I bought designer sneakers and started going to restaurants I couldn’t really afford. I needed people to see my success. My dad drives the same truck he’s had for years. Not because he’s cheap — because his sense of self isn’t tied to what strangers think of him. People who gracefully accept aging tend to share this quality — they stop performing and start actually living.

4. He understood that consistency IS the flex

We glorify the pivot, the disruption, the dramatic comeback story. You know what’s actually harder? Showing up to the same place every day for thirty years and still giving a damn. Research published in the European Journal of Social Psychology found that it takes an average of 66 days to form a new habit. My father built a life of habits that sustained him for decades. That’s not boring. That’s extraordinary discipline disguised as routine.

5. He protected his relationships by protecting his time

When I was building startups, I missed everything. Birthdays. Holidays. The slow, unremarkable Tuesdays that actually make up a life. My dad closed his shop at the same time every day. He was home for dinner. He coached Little League. It looked ordinary. It was actually a radical act of prioritization that I was too blind to recognize.

6. He didn’t confuse motion with progress

This is the trap I fell into hardest. I was always doing something — pitching, networking, iterating, hustling. The motion felt like progress. But motion without direction is just anxiety with a business plan. My dad moved slowly and deliberately. His progress was real, even if it was invisible to someone obsessed with velocity. I’ve written before about destructive habits that erode happiness over time — and mistaking busyness for meaning is near the top of the list.

7. He knew who he was — and that was enough

I spent my twenties and most of my thirties trying to become someone. My dad, somewhere along the way, just became himself. There’s a quiet power in that I couldn’t appreciate until I’d exhausted every alternative.

What changed for me

I’m not going to pretend I’ve fully arrived at some enlightened state. I still live in Austin. I still work from my home office. I still write in 45-minute blocks with a kitchen timer and work out five or six days a week. I still have ambitions.

But the ambitions have changed shape.

These days, I’m less interested in building something impressive and more interested in building something sustainable. Less interested in what scales and more interested in what lasts. My therapist would probably say I’ve started integrating the parts of myself I used to project onto my father — the parts I labeled as “small” because they scared me.

Here’s the kicker: my dad never once criticized my choices. Not when I sold the first company. Not when the second one failed. Not when I showed up at his house broke and pretending I was fine. He just kept being who he was and let me figure it out on my own timeline.

Research on midlife psychological development suggests that this kind of reappraisal — where we re-evaluate our parents’ choices through a more nuanced lens — is actually a hallmark of healthy psychological maturation. It’s not regression. It’s growth. The ability to see complexity where you once saw simplicity.

People who age well tend to share something in common: they stopped chasing someone else’s definition of a life well-lived and started honoring their own. My dad figured that out at thirty. It took me until my forties.

Last Thanksgiving, sitting on that porch, I finally told him something I should have said years ago. I said, “I think you built something really good, Dad.”

He looked at me like I’d said the most obvious thing in the world.

“I know,” he said. And went back to talking about his supplier.

That’s the thing about people who are actually content. They don’t need you to see it. They already know.