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by seer 1889 days ago
I was climbing up the ranks as a dev of a web agency. The owner just got into the startup scene abroad and wanted to be part of it. So he spun up a separate company, and I ended up as a lead dev there. And as the senior dev I ended up with the CTO role.

No experience with that whatsoever, and no support structure to lean on as we were basically one of first gen IT startups in my country. No established processes and we had to invent them as we go. I had read zero books on technical leadership and didn’t know anyone who I could talk to. Didn’t know which books I even had to read as there wasn’t anyone to talk to. HN was my only solace.

I was working like crazy and putting out fires, but instead of helping my colleagues I leaned too much into doing the technical challenges myself.

And it all came crashing down when I went on a long overdue summer vacation. On the first day I start receiving emails in the form of “um we seem to be having a problem, not sure how to deal with it”. It kept escalating day by day, and at one point the CEO just told me “sorry mate but we need you back” and I had to cut my vacation by half and get back to work.

On the bus ride home I kept thinking “never again” and when I got back took a _much_ more serious effort to make sure I wasn’t the single point of failure and actually be a CTO.

Read some books, took some steps back, mentored people, and most importantly actively took less challenging things so others could shine too.

And it worked, I mean I wasn’t that great a leader I’m sure, but there wasn’t a problem that my team couldn’t handle without me afterwards.

Ended up quitting a couple of years later as I was burned out and not happy with the direction of the company overall, but the team is still there more than five years later and growing.

What I learned was that you have to take new responsibility seriously and try to teach yourself for it, not expect things to just “work out”.

1 comments

Thanks for sharing your story.

I‘ve had/have a similar experience. No seniors here to learn from but got it up to top performance with reading (joelonsoftware was a great inspiration back then), investing lots of time (but rarely overtime) and being ambitious.

I believe you also learned that you shouldn‘t be the single point of failure. I‘m still actively working on that. Though it‘s hard to relay to others if they just can‘t get it done or don‘t share your ambitions, vision or views of quality and customer focus. But there‘s always hope.

This is what I also think Antoine de Saint-Exupéry, author of The Little Prince was after.

“If you want to build a ship, don’t drum up your men to collect wood and give orders and distribute the work,” he said. “Instead, teach them to yearn for the vast and endless sea.”

Heard that recently in Julia Galef’s TED talk which I think was awesome.

But I also struggle with that last one myself too. At least now I know inspiration is more about emotions than rational arguments.