Q&A: What Has Been Your Biggest Career Mistake?
My biggest career mistake was staying in one job for far too long before working up the courage to move on to something better.
At that point in my career, I was working at a company where I had a hand in nearly everything within the day-to-day operations, from top to bottom. I was the one getting in early and working past the time when the managers went home for the night. However, despite the amount of work I put into that company, I still felt like a pawn in someone else’s game because I was blocked from contributing to the “big picture” decisions that guided the company’s direction. “Business is fine as it is. Don’t make waves. Just stick to the script.”
I was so damn bored.
I decided that if I was already essentially running my own business, why shouldn’t it be my name on the sign?
Now, wait just a second because I know what you’re going to say. No, this wasn’t about ego or money. The reason I wanted to start my own business was that I, more than anything else, wanted to the ability to make those big decisions that I wasn’t allowed to make when I was working under someone else. I didn’t want to be constrained to “the way it’s always been done.” I wanted to be free to take risks and to challenge myself.
However, it took my a long while before I could shake that nagging voice in the back of my head telling me that I wasn’t good enough. I can’t tell you how happy I was once I finally overcame that fear. It was like the chains came off, and I could actually live my life the way I wanted to. It may sound strange to some people, but I was so excited to finally be free to fail. At least if I failed, I could learn something new. I could do something different. I wasn’t bound by anyone else’s rulebook.
I just wish I had done it sooner.
While I say that it was a mistake to stay as long as I did at that company, I also believe in finding the silver lining.
These days, a lot of entrepreneurial people don’t give themselves the time to learn about the nitty-gritty details of the business world before they dive in. They’re so excited to finally be their own boss, that they don’t entirely understand everything that goes along with it.
You may, for example, know everything there is to know about fixing computers, but you don’t know the first thing about actually running a computer repair shop. In that case, it’s best to take a job at a place where you know you can learn the ropes of running a business before striking out on your own.
While I regret staying as long as I did, I don’t regret learning everything I could from that job before moving on to the next phase of my career. At the same time, I’d urge everyone not to stay at a job if you feel like there’s nowhere left to go.
At a certain point, everyone outgrows their current position. You just need to have the self-awareness to know when you’ve reached that point and the courage to take a leap into the next phase of your career.