Should You Leave Corporate for a Startup? What No One Tells You
From Fortune 500 to startup chaos. My honest guide to making the jump.
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Should You Leave Corporate for a Startup? What No One Tells You
You're sitting in another meeting about meetings, pretending to take notes while secretly updating your LinkedIn.
Is this really it?
The pay’s good. The benefits? Fine.
But every day feels like Groundhog Day, minus Bill Murray's charm. Buzzword bingo, and routines that numb the soul faster than your morning commute.
But corporate life has its perks.
My first job was in digital media at a big American eLearning company. The people were great. I made amazing lifelong friends. For a while, I loved it. I had money for the first time. I spent nights in bars I couldn't afford during college, pretending I understood wine beyond "red" and "white."
But the shine wore off fast. The hangovers hurt more, and the work meant less. It was box-ticking masquerading as progress.
No passion. No urgency.
Just keeping the cogs turning in a machine nobody really cared about.
Like Peter in Office Space, I had nearly eight different bosses. Unlike him, I didn't need a hypnotherapist to snap me out of it.
Then came that fateful email at 4pm. All our jobs were being outsourced to India.
By 4:01, I knew I was done.
I couldn't spend another day pretending that updating slide decks was changing the world. I wanted something messy. Something worth losing sleep over.
So, I jumped into my first startup, dreaming of being my own boss, setting my hours, and making enough money to buy Liverpool FC (I didn’t).
Instead, I traded 40-hour weeks for 80-hour chaos. Late nights, countless hats, and solving problems I didn’t know existed. It was messy, exhausting and addictive.
Over the years, I’ve worked at three more startups and even gone back to Fortune 500 companies a couple of times.
Here’s what I’ve learned about startups and why they might (or might not) be for you.
Normal People Need Not Apply
Normal people follow the product roadmap.
You'll be pivoting that roadmap at 1am because customer feedback just torched your core feature.
Normal people have job descriptions.
You? Last week you were optimising ad spend. This morning you're rewriting user stories because your PM quit after that heated argument about "feature bloat."
Tomorrow? Who knows.
I once got sign-off on a website design late Friday. The founder was ecstatic. 'Perfect,' he said. 'Get it live.'
Monday morning? Same founder, same design. 'Who approved this? It's all wrong. Start over.'
That's the thing about startup life. You're always one founder's mood swing away from a pivot. Remember it's the founder's business. They can do whatever they want. And that's ok.
Tolstoy said:
“All happy families are alike; each unhappy family is unhappy in its own way.”
Same with startups.
The successful ones tell the same story: product-market fit, hockey stick growth, smooth sailing to exit.
The failures? Each one's a unique flavor of wrong decisions, bad hires, and burned runways.
Your Monday starts with your conversion rate dropping by 40%.
By Wednesday, you're stuffing swag bags because your $1m customer is visiting.
Thursday? The founder's dog pukes on the floor during a board meeting about your missed quarterly OKRs. You don't flinch. You grab a mop and keep updating your OKRs.
Normal people would run screaming. But maybe you're not normal.
Maybe seeing a 10% drop in retention gets your problem-solving gears spinning. Maybe you do your best work when your North Star metric is plummeting. Maybe you're the kind of person who sees a negative NPS score and thinks "challenge accepted" instead of "not my problem."
One day you'll feel unstoppable, watching your DAUs hockey stick. The next, you'll question your life choices while staring at enterprise PM job listings.
But if this resonates? If this sounds more exciting than terrifying? Welcome aboard, weirdo. You'll fit right in.
If not, stick to corporate. Normal jobs exist for a reason.
Your Work Will Keep You Up at Night
I once spent weeks on a 125-slide deck that no one read. In corporate, that's just Tuesday.
In startups, everything you touch matters.
Launch a campaign, and revenue doubles. Miss a deadline, and payroll's at risk.
That bug you ignored? It just crashed the site during a demo with your biggest client.
The stakes turn sleep into a luxury.
Not because someone's forcing you to work late, but because your brain won't shut off. Did you double-check that deployment or campaign performance? Will that new feature retain users? Should you have pushed back harder on that founder's "brilliant" marketing idea?
There's nothing like seeing your work directly impact the bottom line.
Customers love it or hate it. There's no lukewarm. Your code, your marketing campaigns, your decisions can make or break next month's numbers.
It's terrifying. Addictive too.
Each win feels like scoring the winning goal. Each failure hits like a punch to the gut.
Sure, equity might make those sleepless nights worth it someday.
You'll screw up. The founder will let you know, probably in front of everyone.
But hey, at least you're not making another slide deck nobody will read.
Startups Will Ruin Regular Jobs For You
The first time I went back to a corporate job after startup life, I felt like Milton watching his red stapler get moved again.
Everything moved in slow motion.
Three approvals for a tweet. Two weeks to update button copy. A month-long discovery phase for a landing page.
In corporate, success means not rocking the boat. In startups, the boat better be rocking or you're doing something wrong.
Startups don't attract paycheck-chasers.
They attract people who light up during whiteboard sessions. Who read documentation for fun. Who actually give a damn.
This energy is rare in corporate life.
When everyone believes in the mission, work becomes something else entirely. Late-night brainstorms feel electric. Victories taste sweeter. Even the pub celebrations hit different. You're not drinking to forget your job, you're celebrating something you built.
But startup passion burns out fast if leadership isn't careful. Even the best startups have weeks that stretch you further than any job should. You'll question everything, including that cushy corporate offer you turned down.
If you want comfort, startups aren't for you.
But once you've experienced work that actually matters, with people who actually care, regular jobs never feel quite right again.
You’ll Get a Crash Course in Entrepreneurship
Think of it as an MBA, minus the $150k debt and plus actual real-world experience.
At a startup, you don’t just watch the sausage get made. You grind the meat. You season it. You clean up the mess.
You’ll see how founders raise money, pivot, and close deals. You’re there when ideas are born, deals are won, and strategies shift.
You’ll also learn what not to do. A bad pitch, a rushed hire, a feature that flops. These lessons are foundational if you dream of ever starting your own thing.
And it’s never too late to learn.
If you’re in your 20s or early 30s, startups can feel like an exhilarating ride.
But what if you’re further along in your career, with a family, mortgage, or other responsibilities? The chaos might seem like a hard sell.
Even if the startup fails, the experience changes you. Going back to corporate after startup chaos is like coming back from Navy SEAL training.
You’re sharper, tougher, ready for anything.
Startup Culture Is a Love-It-or-Hate-It Affair
There's no such thing as "easing into" startup culture.
You either jump in headfirst or you drown in the shallow end.
Forget corporate politics and layers of approval. Startup culture is fast, messy, and unpredictable.
In corporate, you survive by keeping your head down and playing it safe. In startups, staying safe means you’ll sink the ship. One world rewards silence, the other succeeds on noise.
For some, startup life is thrilling.
For others, it’s a nightmare.
Policies? Rare.
Processes? Improvised.
If you crave order and predictability, startups will drive you mad.
But if you love solving problems on the fly, startups might be the most rewarding environment you’ll ever work in.
My Final Thoughts
Look, both worlds have their place.
Corporate teaches you structure and how big organisations work. The coffee's better too.
Startups teach you to build things from scratch and solve impossible problems. The coffee's terrible, but the problems are real.
Early in your career? Try a startup.
You've got nothing to lose and corporate jobs will always be there. You'll learn more in one chaotic year than three safe ones.
More experienced? Startups need you.
They're desperate for people who've seen how things work at scale. And that "startup leadership" experience looks great on a CV. Whether you stay or go back to corporate.
I've done both. Multiple times. Each taught me different things.
But if you're still reading this, wondering if you should make the leap.
What would you regret more?
Until next week,
Martin
P.S. This week's soundtrack: "Life on Mars" by David Bowie.
Tool of the week - Google AI Deep Research
Remember those six-figure consultancy reports that took months to deliver? Google's Gemini does the same research in minutes. I've been using it to validate startup ideas and market research. The data quality is impressive.
Just don't tell your consultant friends.
Book of the Week
Disrupted: My Misadventure in the Start-Up Bubble by Dan Lyons
Grab a copy of "Disrupted" by Dan Lyons. It's the most honest (and hilarious) account of what happens when a tech journalist meets startup chaos.
Great read Martin!