Ep 97: Imposter syndrome and the fear of failure

I’ve closed on dozens of self-storage facilities, millions of dollars of property, and hundreds of thousands of square feet of storage. Most of the cash is deployed from investors I met online. My portfolio is booming. It’s madness, but it’s awesome and I’m having a ton of fun. But I also have a lot of insecurity when it comes to this stuff.

Even saying all this, I feel a huge sense of imposter syndrome. If this is so easy, why isn’t everybody doing this? What if I’m wrong about my educated guesses and logical decisions? What if I’m just another guy who makes his first million and loses everything? There’s a guy on my shoulder constantly yelling at me that the world will find out that I’m just an average guy with below-average intelligence.

But when I think about the 30+ employees who depend on me, and the 200+ investors who have trusted us with their capital, there are a lot of people counting on me. And it’s scary as heck. I feel like I’m flying a full plane, we’re off the ground, there’s no turning back and there are no parachutes. There’s something very unique and scary about taking risks when the downside lands on my shoulders. If we lose, it’s my fault, and there’s nobody else I can blame.

Every now and then my logic kicks in. I think about all the underwriting I do, all the reports I read, all the information I absorb, and gain my confidence back. I realize there are a lot of small things that can go wrong that still result in us making good money. And every time I’ve felt that imposter syndrome, good things have happened. Sure I’ve made mistakes, lost money, and some things have gone wrong, but I’ve grown, gotten smarter, and become a better leader, and things have turned out better down the road because of it.

My default when I get stressed out is to work harder. When things get stressful, I put my head down, push people out of my way, and work like a madman. But that’s not the right way to work through this, I end up working on the wrong shit. Instead, I need to step back and think about what to work on. I need to ask myself what the most valuable use of my time is at this moment, and that usually means zooming out and looking at the bigger picture. Too many entrepreneurs ignore the hard stuff and focus on the easy thing, which is pushing people out of the way and filling time with low-value work.

Thankfully, acute stress is rare in real estate. Our business usually takes long, slow paths and turns. Problems are rarely immediate. In real estate, problems are bigger and manifest over time, but if you focus on them you can find how to avoid them. You can steer the ship.

We all battle insecurity, and it has its place. It prevents us from getting greedy and thinking that we can’t lose, which too many entrepreneurs end up doing after they win a bit. But beyond humility, insecurity is a hindrance. It keeps you from doing your best work, it makes you emotional, and you need to squash it to do your best job.

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About Me

I started the Sweaty Startup in December of 2018 because I believe the Shark Tank and Tech Crunch culture is ruining the real spirit of low-risk entrepreneurship.