Overcoming Self Doubt

When not listening to the gut pays off.

When I first thought about starting my entrepreneurial journey, I was working primarily on gut feel. The gut screamed at me to make a change and I listened.

I quit my job with a lot on the line and made the leap primarily because of the ruckus coming from the belly.

Where things get weird is, not long after I was out on my own, my gut was screaming something else. In fact, the damn thing turned on me and I started a year long battle with self doubt. I lost my mind.

I thought my wife and family had turned on me and that I was no longer relevant to them, or heck, to myself. I was depressed, paranoid and tied myself to the desk with the lights off as I tried to work through it. I isolated myself from everyone because I felt like such a failure even though monetarily it was starting to work.

That year was kind of numbing to me but I believe what finally brought me out of it was when I let my kids shave my head. Literally, shave my head.

I don’t know why, but I walked to them with the clippers and said go for it. It took some convincing but they did it.

Great now I’m worthless and Bald. Wonderful choice there buddy.

But something about that shaved head experience woke me up. It snapped me out of that spiral just enough to realize self-doubt is real and a part of the journey. I had read all about it before starting the business, but there’s something funny about doubt—you can’t really see it clearly until you’re out of it. It’s like trying to navigate in fog, and realizing you’re in the middle of a corn field once its lifts.

The journey of starting a business is overcoming self doubt. Not quitting your w2 job.

Some of the things I remember going through at that time.

• I questioned every decision no matter how small it was: Self-doubt can make you feel like every little thing is life or death, and I ended up spending countless hours overthinking them.
• I felt Extreme Isolation: No one understood the pressures I was going through. I found it extremely hard to relate to people or seek business advice because people just didn’t understand. It was my problem to fix and they can’t help.
• I sabotaged myself: I turned down a lot of handouts for help without knowing it. Friends and family knew I was struggling and they would invite distractions or opportunities that I would turn down so I wasn’t a burden.
• Any small successes felt terrifying, not exciting: I remember not being able to enjoy the small wins. Instead of being happy I remember thinking they were going to be taken away. Like I couldn’t maintain them. Each little success raised the bar to a level I couldn’t possibly reach.

It took about a year before I was able to come out of it. I think in the end, what I learned most, was that overcoming self-doubt is the real game here. The key isn’t to avoid it, but to recognize it, live with it, and push forward anyway.

Shaving my head was just stupid and honestly not that big of a deal. But what it did do is make the emotion of self doubt, real. I could now touch it and see it every time I walked by a mirror.

Now that it was real.. I could whoop its ass for the beating it gave me.

I think what I learned most during that year was….

Starting a business isn’t just about walking away from your old life; it’s about facing down that voice in your head that tells you you’re not good enough—and proving it wrong, day after day.

I wouldn’t trade that year for anything. It made everything real.