STEPHEN KEY: Should You Quit Your Day Job and Jump Into Entrepreneurship?

I received a thoughtful, heartfelt email from a 24-year-old gentleman a few weeks ago. In his email, he listed the books about entrepreneurship he's read, the instructional videos he’s watched and the inspirational events he’s attended. He had decided to quit his corporate job at a large accounting firm in New York City, he told me. He was ready to take a leap of faith. He wanted to become an entrepreneur and invent products.


Boy, did his sentiments bring me back. If you’re an entrepreneur, it’s because you made the decision to be. Anyone who has dared to earn a living as a creative or who has taken an alternative career path knows what I’m talking about.


Was he sure of where he was headed? No. But he was excited to find out. What did I advise?

For years, I told my students, “Don’t quit your day job.” I thought it was wiser to spend a lot of time studying an industry before committing to a new venture, that identifying successful people and learning from their experiences was essential. I thought it made sense to take advantage of working in the field, maybe at a startup. That way, you could raise your hand at every opportunity. Get your foot in the door. Craft a game plan. Sure, doing those things would take time. But it would be worth it.

I think that advice is fine, but maybe a bit conservative. Here’s the problem: Collecting a steady paycheck is nice. You become accustomed to a lifestyle. That lifestyle is harder and harder to walk away from. Hustling takes courage.

When I was young and in my 20s, I didn’t have much to lose. My nerves were less wracked. I was single. I didn’t have a mortgage. I could try and fail and not that much would change. Sometimes I slept on friends’ couches and ate beans and rice. The years I spent selling my products on the street and at art fairs were priceless because I learned so much.

But it’s when my back was up against a wall that I was the most creative. When my wife left her well-paying corporate job, we had three kids and a large mortgage. The pressure was on. It was up to me to support us financially. I did what I had to do.

So what advice do I really have for this young man? I’m not sure. A better question might be, what’s his tolerance for pain? Having a safety net is nice. But if you get too comfortable, risks become harder and harder to take. When you have less to lose, it’s much easier. I’ve known many entrepreneurs to risk it all, and that is clearly not for everyone. So what can you live with? What can you live without? What sacrifices are you willing to make?

When my friends began buying houses and driving nice cars, I was struggling. I remember telling them, “I’m the richest man alive!” No, I wasn’t financially successfully. But I was pursuing my dreams on my own terms. I was charting my own course.

An old friend visited me recently. He was amazed to discover I had achieved what I said I would.

He said that back then, he thought I was out of my mind. But he gets it now. I wasn’t the crazy one. He understood what I meant: That for some of us, doing exactly what we want to do makes us the richest people in the world.

I determined my advice is this: Seeing your dream come to life is the most amazing feeling you will ever have. But don’t sacrifice everything to achieve it.