13 scary doubts about success as a self-made businessperson

We all crave success in some way or another. I thought succeeding as an entrepreneur — on two continents, no less — would somehow put me at peace with the question of whether or not I am “enough.”

Well, it hasn’t. It’s not the fault of entrepreneurship or the industry I’m in, or being oppressed by anyone — it’s just a natural spring of self-doubt from deep within.

In fact, becoming successful seemed to do the opposite of what I’d always anticipated. Instead of quelling doubt, it fed it. Having learned (somewhat) to feel good about myself and my accomplishments in spite of it, I now derive great joy from encouraging others. I want those coming up in the ranks to press forward in their ambitions — but also be aware that success doesn’t mean the end of self-doubt.

Here are 13 negative thought patterns that can occur after you’ve already achieved a major success. These can be disconcerting if you think that you shouldn’t be thinking them. My point here is that it’s both natural and normal to have any of the following thoughts:

• What’s next? When you fail, you just repeat the last step. When you succeed, sometimes it’s unclear where you’re supposed to go next.
• I did it wrong. It’s hard to give yourself credit. If I succeeded, I must have missed something along the way … right?
• Nobody cares. If I really accomplished something, why am I not being recognized for it? Where’s the fanfare? Do I deserve any? Speaking of that …
• I don’t deserve this. Who exactly do I think I am, anyway?
• My friends will resent me now. I know — you’re not supposed to care whether others are resentful or not. “If they were really your friends, …” et cetera, et cetera. But they are my friends, and I do care. Will success get in the way?
• I can’t hack it. Success isn’t a Cinderella story. It’s sweat and tears — I’ve already spilled plenty of both. Will I be able to keep going?
• What if this is the ceiling? Can I learn to be content with what I’ve achieved? What if I don’t ever achieve more?
• Can I ever be happy? Success hasn’t seemed to unlock any secrets. Will I ever be able to accept that happiness is a journey, not a destination?
• I’m lying to myself. This isn’t true success. The other shoe is going to drop any moment now. I should prepare to be disappointed.
• If I fall, I’ll never get back up. Getting here was too difficult. I’ll have to hold on to this, no matter what toll it takes.
• What if people turn on me? I’m human — not perfect. Sooner or later I’ll make some big mistake, and then what will happen? I could lose everything.
• I’m not sure who I am anymore. Success changes people … or does it? Do I need to somehow reinvent myself in order to maintain my new standing?
• I’ve been wrong about everything. Becoming successful didn’t do everything for me that I thought it would. What else am I wrong about? Relationships? My purpose? My whole life?

We can’t stop these kinds of thoughts, even if we learn to be mindful of them. But we don’t have to believe them. In fact, imagining everything we think is true would be the height of narcissism, right?