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My Worst Mistakes (And Why You Should Learn from Them)

I think that if you’re a small business owner or entrepreneur and you can say you haven’t made mistakes or screwed things up now and then, well, you’re not taking enough risks.

I’ve screwed up plenty. Some small things. Some big things with even bigger consequences. That doesn’t make me a bad business owner. In fact, I think it makes me a pretty damn good one. I may not have always made the best decisions, but I have learned from every single one of them. And at the end of the day, I can call myself a successful small business owner and feel good about where my company is now and where it’s going.

I’m launching a series of posts where I talk about some of the biggest mistakes I’ve made, why they were wrong, and what I learned from them. Why am I going to bare my failures as a business owner? Fair question. There’s a few answers, I guess.

First, there’s a lot of ego in business. There’s a lot of pressure to seem like you’re perfect and have never faltered. But you have. And will again. And that’s ok. It’s good to remind ourselves sometimes that perfection is a nice goal but it’s not attainable.

Second, I want to help other companies be better. Learn from my mistakes. They certainly aren’t exclusive to the software industry—most are pretty widely applicable. These mistakes were hard on the business and my employees. If I can help even one business owner avoid them, I’ll count it as a win.

Third, it’s a reminder that no matter what, you have to keep going. I made some blunders at the beginning of LeadMD that could have tanked us. But I was committed to pushing through the difficulty and coming out the other end stronger than ever. And we have.

Read these posts when they’re published. Cringe in all the right places. Feel fear. Take notes, too. Know that you’re still going to make mistakes. But you don’t have to make mine.

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