Quitting your Corporate Job: Myths vs. Reality
What it's like to leave the corporate world in your 30s to build your own thing
Recently, some friends who are also in their 30s have been asking me what it’s like to quit the corporate path to start a company. They want to, but they’re scared of failing, of losing their footing, of not being able to come back to stability again.
I was in this position not too long ago.
At 33, I left my big tech job to start a company with a friend. We had no funding, no customers, and no salaries at first, just pure optimism. I’d romanticized entrepreneurship my whole life and I wanted the creative freedom, the challenge, the thrill of putting ideas into the world. But I also had real fears going in. Would it be lonely? All-consuming? Insanely stressful?
Now, a year and a half later, here’s what’s actually true.
Preconception 1: It’s lonely
Verdict: False
I’ve found the opposite to be true. Once you start a company, people will naturally want to get to know you. And if you’re in SF or New York, there are endless founder dinners, investor talks, and conferences to attend.
Friends and former coworkers will reach out to check in, offer intros, or ask for advice on their own projects.
And more than ever, your friends and past coworkers will reach out to check in on you, weigh in on your idea, offer intros, or ask you for advice on their own projects (pitch decks, marketing copy, etc).
Rather than being lonely, the bigger adjustment for me was learning to politely decline invitations. Early on, I attended almost everything I was invited to, and quickly realized that endless networking doesn’t move the business forward. Focusing on distribution and building your product do.
I’ve also noticed that my social and professional circles have blended together more than ever. When you’re thinking about your company all the time, you’ll naturally gravitate towards people who are on the same path. There’s a natural camaraderie in that; rarely does it feel lonely.
Preconception 2: It’s mentally draining
Verdict: Somewhat
The startup path carries more mental load than anything I’ve experienced in corporate.
There’s been heated cofounder debates about company direction, anxiety about competitors (or Anthropic building your replacement), investors passing, customers ghosting after months of trial feedback — these are the classic lows of an early-stage startup.
But the highs are even higher.
The moment we signed one of the largest consulting firms as a customer, getting into our top choice of accelerator after being passed on, being in SF around some of the most intensely driven founders I’ve ever met. These are things you’d never experience in the corporate world.
In corporate, any promotion, slack shout out, or launch feels a bit more dull simply because it’s not yours. When it’s your company, there’s a level of intensity that you’ll feel that’s on another level.
The lows are lower, but the highs are much, much higher.
Preconception 3: It requires significant lifestyle sacrifice
Verdict: It depends
There’s a stereotype that being a founder means living on ramen, sleeping on a mattress, and working 996 hours.
From my experience and friends also running startups, that culture is pretty exaggerated.
Granted, my experience is different from someone who’s building a startup straight out of college. I left at 33 after an 9-year tech career, with a financial cushion and a professional network. That runway let me focus on building without panicking every time progress slowed.
The actual tradeoffs I made were:
no health insurance for a few months before we raised (COBRA is $700/month, which is insane)
cooking at home more
taking the subway and walking instead of Ubers
That’s about it. I didn’t miss any weddings or important family moments. I still had hobbies and a life.
If anything, the financial constraints proved useful. I wasn’t struggling to the point of sacrificing a safe neighborhood or healthy food, but there was enough pressure to instill urgency. I need to build the product, get customers, and raise capital fast.
A bit of urgency isn’t a bad thing, but this is a marathon, not a sprint. Burning out in year one helps no one, least of all your company.
Preconception 4: It means facing constant negativity
Verdict: False
Entrepreneurship is deeply embedded in American mythology and the founder is often depicted as an underdog who bets everything against all odds and wins.
Implicit in that story is the idea that nobody believed in them, that founders persevere through everyone around you saying your idea sucks. I held this idea in my head from a lot of the entrepreneurship memes and hustle content I saw on the internet, and clips where Mark Cuban is brutally roasting people’s work on Shark Tank.
The reality is that rejection is part of any competitive path, and startups are no exception. For me, breaking into tech out of grad school took hundreds of job applications. I’ve probably faced more rejection applying for jobs in my 20s than in all of fundraising and sales combined.
In fact, most nos from investors and customers aren’t delivered as blunt rejections in the way an interview rejection is. They’re more of a “not yet, come back when you’re further along.” There will always be the VC investor who wants to power trip or a customer having a bad day, but those are the exceptions. Most people are genuinely supportive of someone doing a hard thing, and even tough interactions usually just point you in a new direction.
The support network is what actually catches you off guard. Friends wanting to angel invest, people rooting for you that you didn’t expect.
More than wanting to prove the haters wrong, you might find that you’re driven to prove your early supporters right.
Preconception 5: It requires genius level intelligence and charisma
Verdict: False
When you hear stats about who starts companies and how many fail, it’s easy to wonder: am I cut from that cloth? Do I need some innate level of talent, connections, or charisma to pull this off?
Honestly, no. The one thing I’ve noticed that separates people who succeed on their own versus in corporate is that they’re not afraid to try. They’re not afraid to ask for the intro, send the cold email, or publish a hundred pieces of content that flop in front of all their old coworkers before they get their first hit.
They have less shame about failing, and an irrational level of self-belief that things will work out.
Once you jump in, you’ll quickly realize what Steve Jobs once said is true: everything around you was built by people no smarter than you.
So would I make the same choice again?
Yes, and I don’t plan on going back.
This experience has enabled growth in ways I didn’t expect. I’ve picked up skills in sales, growth, and doing more with less. It’s also forced me to confront some old habits, like perfectionism and the need to control every outcome.
Most of all, this taste of freedom has been a genuine life unlock. Owning your time, work, and living with the consequences of your own choices is addictive in the best way.
I do sometimes wish I’d left corporate sooner, but there are advantages to starting this journey in your 30s. For all the ways Silicon Valley glorifies the 22-year-old dropouts, the experience I gained from four years at Robinhood has been invaluable. I’m still in touch with friends I made during that job, many of whom are also founders now, and we regularly swap tips, make intros, and help each other with strategy.
If you’re deciding whether to quit your corporate job, I’ll leave you with this:
The biggest barrier to entry in entrepreneurship isn’t talent or connections. It’s the willingness to get started, to go all in.
Some people have a head start, the right network, the right upbringing, the early wins that build self-belief. But once you’re in the game, that levels out faster than you’d think.
Business is still one of the most meritocratic arenas there is in life, and the only way to find out if you’re cut out for it is to jump in the deep end of the pool.
And who knows?
Maybe you’ll find that you were born to swim there.