I Left Corporate America Three Times to Pursue Entrepreneurship

The first time I quit corporate America, I was 25.

I didn’t have much in savings, but I had a big vision and the naïve belief that pure drive would be enough. I wanted to do more good in the world, and I thought entrepreneurship was the way.

Six (6) months later, the money ran out. I had to swallow my pride, return to corporate, and face the fact that vision alone doesn’t pay the bills. But I came back wiser.

The second time, I lasted one (1) year. I was a little more experienced, a little more prepared. And when I returned again, something surprised me: the leaders I worked for didn’t look down on me. They respected the fact that I had bet on myself. They valued the risk I had taken, even if I hadn’t “made it.”

The third time was different. I stayed out for three (3) years. By then, I had savings, partners, and multiple ventures in motion. This was the leap I thought would stick. And in many ways, it did but it also nearly broke me.

The financial stress was relentless. Even with my largest cushion, life eroded it quickly. I developed hives and eczema from the pressure and these health issues still linger today. I learned the hard way that you don’t think clearly when survival is at stake. If I were to do it again, I’d build enough traction to replace at least 80% of my income and benefits before leaving. Stability buys clarity.

And yet, that third leap created the most lasting results. One venture has been running for over 14 years, creating jobs and supporting youth sports. Another is a cash-flow machine, paying me like a rental property every month. A third is still “baking,” but I expect to recoup my initial investment in the next 2-3 years (fingers crossed).

Lessons Along the Way

Looking back at three exits and three returns, here’s what I’ve learned:

• Corporate will always be there. When you leave, your peers keep moving...promotions, homes, families. But the door doesn’t close. You can return, and good leaders will respect the risk you took.
• Entrepreneurship changes you forever. After getting punched and kicked in business, corporate challenges feel small. You’re more grateful, less entitled, and harder to rattle. And while a paycheck is steady, nothing compares to the dopamine rush of closing a sale you created from scratch.
• Financial stress can break you. Set a hard number you’re willing to burn. Live lean, but don’t cut all joy from life...get the coffee, grab a drink with friends. You can only cut so much, but your earning potential is uncapped.
• The opportunity cost is real. Walking away means giving up wages, promotions, and employer matches. You have to build something that outweighs all of that.
• Key person risk matters. In small business, if the whole venture depends on one person, it’s fragile. Build systems, not bottlenecks. Ironically, corporate rewards the same thing and leaders respect when you make yourself redundant.
• You’ll learn more than any MBA. Running a business for a few years is like a crash course in leadership, finance, marketing, and resilience. You don’t need a degree, you need the mindset to try.
• You can’t do both well (In most cases in my experience but I know people who've done it). Straddling corporate and entrepreneurship rarely works. At some point, you have to commit 100% one way or the other.
• Ego is the enemy. My best return to corporate came when I went back to the very company I had left. I already knew the people, the role, the challenges and was able to hit the ground running without having to establish it all again. Sometimes the smart move is the humblest one.
• Corporate isn’t always the villain. Sure, some companies work you to the bone. But there are also places that offer flexibility, autonomy, and great compensation. If you find one, don’t take it for granted.
• Use corporate to build assets. Leverage your W2 income to buy assets before you leap. Those assets will cushion you when you’re ready to take the plunge. If you can, buy assets that spit out cash flow!
• There’s no perfect age. It’s not about when rather about mindset. Though truthfully, it’s easier when you’re younger and have fewer responsibilities.
• Focus on what you do best. In both business and corporate, your greatest leverage is your strengths. Build around them, and find partners to cover the rest.
  

The Human Side

Your friends will cheer you on. They’ll be inspired by your leap. But your family feels the weight differently. They carry your stress, and if you lean on them too much, you risk becoming a burden. Protect them as best you can.

And while the money and stress dominate the story, the real return is often the people you meet. Running businesses put me in rooms with self-made entrepreneurs, operators, and dreamers I never would’ve met in corporate. Some became mentors. Some became partners. Some became lifelong friends.

These relationships are priceless. They give you perspective, challenge you to grow, and open doors you didn’t know existed. Even if you return to corporate, those relationships and that perspective stay with you forever.

The Truth

If you stay in corporate long enough, you’ll either get the itch to leave or you’ll trade your fire for stability. Neither path is wrong.

I’ve left three times, returned three times, and gained more each round. The money wasn’t always there, the stress was real, and the sacrifices were heavy.

But I don’t regret a single leap. Because even though I came back, I know the feeling of pure freedom. And that’s something most people will never experience.

Checklist: Preparing to Leave Corporate for Entrepreneurship

Financial Preparation

☐ Build a runway that covers 12–18 months of living expenses.

☐ Ensure 80% of your current income and benefits can be replaced through savings, assets, or early business traction.

☐ Leverage your W2 income to acquire assets (stocks, BTC, real estate) before quitting.

☐ Set a hard "burn number"—the maximum amount you’re willing to invest or lose before re-evaluating.

Business Readiness

☐ Validate product-market fit—don’t leave just to “figure it out” blindly.

☐ Minimize key person risk—the business shouldn’t collapse if you step away briefly.

☐ Build relationships with mentors and peers in your target industry.

☐ Focus on what you do best—line up partners or hires for everything else.

Mental & Personal Preparation

☐ Discuss your plan with family and shield them from full financial/emotional burden.

☐ Prepare for financial stress and create routines to maintain health and resilience.

☐ Commit to a start date and a review date to assess progress objectively.

Checklist: Is It Time to Return to Corporate?

Financial Indicators

☐ Your runway is running out and you can’t invest in growth.

☐ The business cannot support you without draining savings.

☐ Financial stress is affecting your health (sleep, anxiety, medical issues).

Business Indicators

☐ Product-market fit isn’t there after significant time and pivots.

☐ The business relies entirely on you—too much key person risk.

☐ Your partners or team are burning out or leaving.

Personal Indicators

☐ You’ve lost the passion that fueled you.

☐ You’re avoiding hard decisions just to keep it alive.

☐ Returning to corporate feels like a strategic move, not a failure.

Re-Entry Mindset

☐ Ego isn’t stopping you—you’re open to the right company or role.

☐ You’ve maintained relationships and can leverage your experience.

☐ You’re ready to keep the business alive in a passive role, if possible, while regaining stability.