Entrepreneurship: There will always be a reason not to make the leap

As an industry, we are so focused on speaking to founders that we often ignore the people who fancy themselves entrepreneurs but who haven’t ever taken the leap.

When we do address them, we chide them for being wannabes and for not having courage and grit. In fact, few have criticized them more harshly than I have. But I want to take this opportunity to address this group, not as a critic, but with the intention of perhaps providing the spark that might help them make the jump.

If you’ve dreamt about being an entrepreneur, or dreamt about anything really, know this: There will always be a reason not to do it. There is no such thing as the perfect time, no magic moment when everything lines up and makes the decision to quit your job feel easy. If you’re waiting for that moment to come, you’ll likely wait forever. And no matter what credentials someone has or how much money they’ve made, nobody can remove the uncertainty from an inherently uncertain path.

Instead of fearing the unknown future of taking a chance, entrepreneurs fear the known future of not taking a chance. Ask yourself what scares you more — continuing what you’re doing for the rest of your life, or the possibility of losing what you have in pursuit of something greater. How you answer this question will tell you if you are cut out for entrepreneurship.

Just before my 30th birthday, after spending my 20s as an entrepreneur, I decided to go corporate. For a while it seemed like the best decision I had ever made. The lack of stress, generous expense account, and solid paycheck seemed like a great deal and made my earlier efforts to run my own business look downright foolish. But everyone around me seemed like they just weren’t happy. There was always talk about doing something else, and of course lots of complaining about the boss. I remember the exact moment, looking at our 50-year-old vice president of sales working late for the umpteenth time, and thinking, “If I stay on this course, this is my future.”

Unless something forces your hand, the future of well-worn paths is easy to predict. For example, nearly 15 years later, the friends I’ve maintained from that corporate stint are in the exact same situation they were in then, just a few levels up the pay ladder. Every day you spend saying there is this reason, or that excuse, why tomorrow or next week or next year will be the time something happens is another day you are doing nothing.

As Gretchen Rubin wrote, “The days are long, but the years are short.” If you’re in your 20s, it’s easy to think you have forever to make something happen. But if you have the benefit, or the curse, of time under your belt, it’s likely this quote rings loudly with frightening truth. If you don’t make the decision to do something soon, to do something now, the years will fly by. Time won’t wait for you.

As for me, the risks of entrepreneurship have never been a problem. I think I just really hated living life in cubicle-land. But a few months ago I started thinking about what the next 10 and 20 years looked like if I stayed in Los Angeles. While my life in L.A. was easy and comfortable and safe, the future also looked like more of the same, and that wasn’t what I wanted. So I sold my house and now I’m writing this from a hotel room that is currently my new “home.” Only time will tell if it’s the right move, but I rest easy knowing that I’m doing something instead of doing nothing.

If you’ve been on the fence about making the leap to entrepreneurship, or something else you want to pursue, but can’t find the right time, remember there will always be a reason not to. You just have to decide what matters more: those reasons, or starting on a new path for the rest of your life.