They say you should live your life without regrets and I would agree with them. I was doing well with this notion until I sat down at a deli with the CTO of a local high tech startup. It was then I had my first regret in my career.

We were very seriously discussing the idea of completely re-writing a Microsoft based software stack to Ruby and Linux. It sounded challenging, kind of crazy, but immensely interesting. They had great business reasons for doing so and I was already offering up ideas for how to start shifting things.

The conversation thoroughly convinced the CTO I would be a great fit, but there was one catch. At the end, he explained this would be a leadership position. The existing Microsoft based team would be re-trained to be Ruby developers and within a specific timeframe, we would have to migrate all services over to this new technology stack. I panicked a bit because this was my first legitimate shot at being a software development manager, something I had been wanting lately in my career. After the meeting, I wrote back to the CTO about his offer and politely declined, offering to connect him with a friend who was looking for a lead position.

I’m not sure what specifically made me decline that offer, but it was my first big regret of my career. I was on the edge of my career knowledge gap, looking to leap up to leadership. When an offer like that was in front of me, I freaked out and started to doubt myself. Imposter Syndrome striking again, making me think I’m not capable, I’ll screw it up, they’ll think I’m a fraud.

More than 6 years past that moment in my career, I’m finally headed back to that path. The fork in the road that lead me into one of the best jobs in my career at DNSimple. This time, I would be ready to walk the scarier path towards leadership. Lots of therapy has helped me find my inner voice and strength to shut that voice up inside me that doubts I can do this. I was very up front in my interviews with Packet about wanting to take this step and they were all too happy to welcome me to take that path.

As of July 1st, I’ve started work at Packet to a warm welcome from my team and the company. Much work to do, but everyone has been very enthusiastic thus far. Even as I push into this job initially as a Senior Software Developer, the more managerial tasks I take on, the louder that little voice gets inside my head. This next chapter in my career will be an interesting one and I promise to keep you all posted about my journey.