Someone whom I consider a good friend and good person graced my inbox today with his very own blog-like post. He wasn’t sure what to do with the text spiraling around in his head and hard drive and asked if I would like to post it here. Giving it wings to fly into the world and be heard. Given I had been twiddling my thumbs lately on a similar themed post, I decided it was perfect timing.
Please enjoy this first, guest blog post:
Why I’m Okay with Being the Dumbest Person on the Team (Again)
The Career Doom Cycle

Recently, I discovered that I’m absolutely clueless at work. I could probably compete with the interns over who makes the better coffee. Ten years into my career, and suddenly I have no idea what the heck I’m doing anymore. You might wonder how I even managed to get the job in the first place if I’m that bad at it. The funny thing is… it wasn’t always like this. In fact, a few months ago, I felt pretty confident in what I was doing. So what happened?
Over the last six months, our department went through a major restructuring. Managers rotated, teams were reshuffled, and with new leadership came a completely new product vision. Overnight, the things I knew best suddenly weren’t the things that mattered most anymore. New processes, new architecture, new ways of working. You name it. It felt like someone had hit the reset button on everything I’d spent years learning, and I was back to figuring things out one question at a time.
That’s when it hit me: this isn’t the first time I’ve felt like this. In fact, it seems to happen every time my career takes a meaningful turn. You get comfortable, you know what you’re doing, and then something changes. A new role, a reorganization, a different project. Suddenly you’re asking what seem like embarrassingly obvious questions again. Little by little, you figure it out, build your confidence back up, and eventually become the person others turn to for help. Then the next big change comes along. Boom. Back to square one. That’s the Career Doom Cycle. No matter how experienced you become, there’s always another reset waiting around the corner.
So, why am I okay with being the dumbest person on the team again? Because I’ve realized that feeling clueless usually means I’m learning something new. Every time I’ve gone through this cycle, I’ve come out of it knowing a little more than before. The real doom isn’t getting thrown back to square one every now and then. It’s staying in your comfort zone. If you never feel out of your depth, chances are you’re not stretching yourself anymore. I’ve come to realize that the people with the best careers aren’t the ones who avoid the Career Doom Cycle. They’re the ones willing to go through it more times than everyone else. As for me, I’ll happily make another cup of coffee and start asking the “stupid” questions again. I’m sure it won’t be the last time.
