6 Ways to Doubt Yourself and Do it Anyway

Using fear of failure to drive your business further

In my short time as an entrepreneur, I've begun to understand the people that describe running your own business as a rollercoaster. Like most cliches, it comes from truth: in any moment, the grandieur and surety of your world-changing vision vanishes, replaced with doubt and the sinking feeling that you’ve made a horrible mistake, your parents were right, you should have stayed in that boring, stable job, and disaster is imminent.

In those moments, your resolve is tested. While there may be some crazy, delusional souls capable of feeling nothing but confidence for years on end with no feedback or direction, for the rest of us, we need to find mental toughness we didn’t know we had. Below are some of the tricks I’ve told myself to make sure I got back up every time I knocked myself down:

Your bad decisions don’t matter; you’ll be dirt soon anyway (or “If he’s so smart, how come he’s dead?”). John D. Rockefeller is widely considered the richest person in human history. Just about every business decision he made was the right one, and he amassed a great fortune. But just like everyone else in history, he died, and the company he built is gone. The world kept turning.

On the flip side, consider your own life, and the worries you have about your company. Even if your worst fears come true, no business decision you make will (probably) be bad enough to change the course of human history. It’s a bit morbid to think in these terms, but to me, it means freedom. It’s easy for some decisions to feel catastrophic sometimes, and it keeps things in perspective when you remember that your life is short and inconsequential.

Whatever you do, the world will keep turning. Be a bit of a nihilist. Personally, I think nihilists get a bit of a bad rap. Nothing I do matters? That means I can do anything! There are no rules! While some people may get discouraged by this lack of meaning, I find power in it. Whether or not your life is meaningful only comes from one place: you. If you find meaning in what you’re doing, then it’s worth doing. If you don’t, then change it. Nothing else matters.

Similarly, this perspective makes it easy not to sweat the small stuff. Existence is meaningless? Guess that makes worrying about this expense report pretty silly. Guess there’s no sense agonizing over this minor design tweak. Guess I should just go for broke and see what happens. Failure is temporary. I’ve heard this said before, but it’s never more true than for an entrepreneur. One of the biggest differences between running your own business and working for someone else is the cost of failure: if you fail at the latter, you get fired and try to find yourself the same job somewhere else. If you fail at the former, you move forward to something new, building on the experiences that you had before. You get to move forward whether you succeed or not! Maybe it’s a pivot for your business, maybe it’s a new venture that came from the last venture’s demise, maybe you made a connection that leads to the next adventure. Any way the chips fall, it’s progress.

Of course, I’m not oblivious to the financial consequences of your own business failing, especially when it’s personally guaranteed. But those fears are omnipresent either way. You might as well balance them with a view to the positive takeaways of this particular project not working out. Don’t feel bad for hedging your bets. I’ve met some entrepreneurs who feel like anyone who thinks of anything other than the singular domination of their company is destined to fail. I think that’s unfair to yourself, both now and in the future. You can have faith in your business while remaining open minded about possible pivot points, or different directions to take it. Could your B2C idea have a B2B element to it through licensing? Could your freemium model be better served as a subscription service to a smaller but loyal market? Maybe you’re staying in touch with your old employer, and after a while they come to view your experience as unique and they want to bring you back in a new, more appealing position. Or your network of contacts brings you in touch with someone who presents a job offer that makes you happier than your own company ever made you in the first place.

Looking elsewhere doesn't have to mean being disloyal to your vision; it can mean having your eyes and ears open to every opportunity available, both for your company and for yourself. There are no prizes for being ordinary. Before I started my company, I was fortunate to have a secure, decent paying job in a field that made use of my qualifications. I don’t minimize the rarity of that, and anyone who is happy with that path should stay on it.

But don’t go down that road because your friends/family/educators/everyone you’ve ever met are telling you to. Eventually, all that helpful advice starts to burrow into your brain, and it starts to feel comfortable to just follow the path of least resistance. Keep reminding yourself that this comfort is a mirage. It doesn't guarantee happiness, or a pot of gold at the end of the rainbow. Regret is the alternative, and that’s worse. If you never follow your dream, there will come a day, maybe a year from now, maybe 30 years from now, when you will wonder what could have been. Worse, someone else may have wild success with something similar to your idea, and you’ll wake up every day thinking, “That could have been me.” Compared to that, failure is a cakewalk.

When you’re running your own business, you can be your own worst enemy. As I’ve slowly come to learn, a positive mental state can be more useful than any connection, any press coverage, any website traction you have. Use whatever tools you have to find one.

If you have more ways to keep pushing through those moments of doubt, please drop me a line!