I just need to start

I used to be a very productive person. Relentless at work and enthusiastic to take on new challenges. Little did I know, there was an obstacle being masked by my performance but even more so, my role. And advancing my career would be the shock that I needed to expose it: I had trouble starting.

Being handed tasks and urgent troubleshooting work masked the fact that I had trouble jumpstarting things on my own. Working in the software industry, it always helped that I was constantly being handed tasks that were already on fire and it was part of my job to put them out. I took pride in being good at those kinds of tasks and had made a career out of it. Calm under pressure, composed amid the chaos.

A critical issue in production that need to be solved within the hour? Got it. An executive escalation from a partner having trouble with one of our products? Solved. A new and exciting project that requires learning an unfamiliar technology in a short amount of time? Sign me up. Remember to log your daily work hours for routine time tracking? Crickets.

If it wasn’t dripping with adrenaline and nicely wrapped with a bow reading “Emergency”, the chances that I would pick that task up are slim. In retrospect, it made sense that my first two jobs were both at fast moving startups with highly visible products.

But then I moved to consultancy that forward deployed me to one of the countries biggest and oldest banks: timelines were in quarters and milestones were in months. Yawn. I didn’t even last six months. Combine that with a global pandemic that raised everyone’s baseline of what is important and by extension, what is urgent, the energy required to get over the hump of getting anything started shot up significantly higher. And it wasn’t just work, it had started to spill over everywhere.

Hacking into the deficiency

This is how Conan O’Brien often quotes how his father finally understood his brand of comedy and his career. It took me several more years, but everything clicked and made sense when I finally realized what was happening.

By then, I had already accumulated a number of habits and patterns that helped mask my tendencies. I had rebuilt my reputation on my strengths to overshadow my weaknesses. Setting aside the curse of knowing and the growing impostor syndrome, the fear of “being found out” became newfound fuel that stoked the ever growing wildfire of my own perceived productivity.

Moving out of leading software teams towards more strategy and practice governance, the bar I had to clear continued to climb. More time on my hands, more say on what “success” looked like, the boundaries between tasks blurred even more.

I had to learn even more techniques to manage on my own. Chunking, time blocking, personal kanban boards, body doubling (pair-programming, working sessions, etc.), name it, I’d probably tried it. It’s hard work but it’s annoying that it’s also obvious that they work so I have to keep at them.

Have I won?

I don’t think I’ll ever permanently win. It’s one battle after another, no way around it. And it’s hard work. There are days you win, there are days you get reminded of the full weight of the responsibility — some days more than others.

When I started that first post and outlined it, I definitely lost. I know because I’m writing this and this is my first post.

It’s a tightrope walk between self-blame (“I should just try harder.”) and learned helplessness (“I’m broken, so there’s no point in trying.“). It’s not a moral failing or an issue with my own identity, it’s simply a different set of constraints. It’s the landscape I’m navigating, not the driver at the wheel.

What I build, write, or thoughts I have are still mine, there’s just a different set of obstacles I have to maneuver to bring myself to start.

And here, at the end, is where I start.