Corporate vs. Startup: I’ve Lived Both
5 years in a suit. 3 years building from scratch. Both made me question everything. This one’s for anyone wondering which path is “right.”
Jack Boudreau
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Main Story:

Corporate vs. Startup

This isn’t some “escape the matrix” post. It’s not about how corporate or J.P. Morgan is evil and startups are freedom. It’s just the truth. Because if you’ve only lived on one side, it’s easy to believe the grass is greener. And let me tell you it’s not. The grass is just different.

For context, I started the first five years of my professional career as an analyst and associate at JPM, but departed right when my compensations began to skyrocket ($250k+/yr)

Why? Keep reading…


The Corporate World: A Masterclass in Predictability

I started at a big bank. Publicly traded. Highly respected. Basically the Navy SEALs of neckties and Excel. If you weren’t in court or law school, this was as old-school corporate as it got.

For perspective, it was “progressive” that it wasn’t a requirement to wear a tie every day. Yet, we kept extras in our desks “just in case.” Zoom wasn’t a thing. Paper was king. And the tech stack was PDFs and maybe a few Excel macros if you were feeling spicy. But I didn’t care, because I was young and hyped on kool-aid.

At first, the structure felt like safety. There were ladders to climb. Roles to respect. Expectations were clear. I got to travel. I got to meet people. I felt like I was building something stable.

But it didn’t take long for the cracks to show. Everything felt life-or-death. You could mess up nothing, but also… do nothing of actual substance. I would spend hours fixing one f**king slide for a client presentation that would get a 5min glance before it hit the trash.

It was about looking busy. Sounding important. Playing the part. There were meetings about meetings. There were performance reviews that judged you on politics, not progress. You learned quickly that it wasn’t about being the smartest, it was about who could navigate the maze without pissing someone off.

And I was good at it. But the better I got, the more I realized how soul-numbing it was.

Corporate teaches you consistency, but numbs you to the fact that nothing is really changing. You’re just getting better at playing the game.


The Startup Shift

Then I left (2022).

No parachute. No roadmap. Just an idea and a gut feeling that I needed more. I walked out of a salary, a team, benefits, a 401k—all the things people dream of—and jumped into a world where nobody gives a sh*t what your resume says.

Suddenly I had to earn my relevance every single day. I had no idea what I was doing. There were weeks I thought I had hit rock bottom. Months where I didn't know if I’d get paid. Days where I genuinely questioned if any of this would work.

But I kept going. Waking up, trying, failing, fixing, trying again.

That’s the secret no one tells you: You don’t find confidence before you leap. You build it one terrifying day at a time.

And eventually, I started building something that mattered. Not just to me but to real people. I could see it. Feel it. It wasn’t a PowerPoint slide anymore, it was real, messy impact.

But startup life? It’s not glamorous. It’s chaos. No one holds your hand. And if you don’t thrive in uncertainty, respectfully, this life will eat you alive. Every day is a new puzzle with no instructions and a timer counting down. You get good at making fast decisions with limited info. You learn what actually matters, fast.

Startups force growth through fire. If you can handle it, the reward is feeling truly alive in your work. But it will never feel “safe.”


Stress is Universal

In corporate, stress comes from politics, perception, pretending to care about things that don’t matter. It’s slow-drip anxiety.

In startups, stress is faster. Louder. You’ll have moments where you wonder if you’re ruining your life. But it’s your own stress. You own the outcome. That makes all the difference.

In corporate, you become numb to the consistency. The predictable, plodding rhythm of emails, decks, meetings. In startups, you become numb to the uncertainty. Every day feels like you’re either three steps ahead or three steps from disaster.

Pick your poison. There is no stress-free path. Just a version you can live with.


The Identity Whiplash No One Talks About

One of the weirdest shifts? How people see you.

Saying “I work at JPMorgan” made conversations easy. People got it. You got the nod. Saying “I’m building a startup” makes people tilt their head like a confused dog. You feel like you need to prove you’re not unemployed.

Even I still catch myself downplaying it. I’ll tell strangers I work in sales or “at a startup” just to avoid the explanation. Because early-stage startup life isn’t always sexy. There are no press releases. No big exits. Just you grinding it out, hoping you’re not insane.

But the best part? You start to build an identity that isn’t tied to a logo. You define yourself by what you do, not where you work.

Leaving corporate means leaving the validation too. But you gain a version of yourself you never got to meet before.


So… Which Is Better? Honestly, I Don’t Know.

Some days I miss the structure. The benefits. The clear boundaries of a “real job.”
Other days, I can’t believe I ever traded my time for PowerPoint politics and lunch-and-learns.

There’s no right answer. Just tradeoffs. If you offered me $50k/yr more to go back to a stable job that felt like sleepwalking, I’d lose my mind. Because work is a big part of my life. It gives me purpose. But that’s me.

For you? Maybe purpose comes from parenting. Or writing. Or volunteering. Maybe work is just the thing that funds the life you actually care about. That’s cool too.

You just have to know what you need. Because neither corporate nor startup life will hand you peace. You have to define it, then build around it.

You don’t figure out what’s right by thinking. You figure it out by trying. That’s the only way.


Final Thought: I’m Grateful I’ve Lived Both

I don’t know what the future holds. I still wake up some days unsure what the hell I’m doing. But I’ve lived two radically different lives before 30 and I wouldn’t trade that perspective for anything.

  • Corporate gave me stability. Startups gave me freedom.

  • Corporate taught me discipline. Startups taught me grit.

  • Corporate showed me how to play the game. Startups showed me how to build my own.

They both matter. And they both mess with your head in different ways. But I’m glad I’ve lived them both. Because now, at least, I’m choosing my path with my eyes wide open.

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What’s Coming Next?

So now that I’ve spilled the beans on Morningstar, I plan to write up my opinions about attending conferences, events, and the balance between “is this a f**king waste of time” vs. the huge advantages that can stem from them.

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