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Having short tenures (is 2 - 3 years short?) allowed me to be an IC for cool projects, to be CTO at a bootstrapped company, to be CTO of a VC backed company, to work on amazing projects around the world with interesting people, consult in big projects, to learn so many technologies and ways of doing things and on top of this to make so much money doing things I love, and have the autonomy to make my own life decisions.

This has happened while some people I know have been working on and maintaining the systems they got hired 15 years ago to build. Power to them. But they get paid like shit and I can’t really talk to them about the current technological landscape as they’ve been doing the same thing, in the same way without any disruptions. You’d expect them to be domain / tech-vertical masters, but unfortunately when you’ve been sliding in comfort for a decade, there’s a chance you lost most of your edge.

In my experience, there’s two (relevant to the point) kind of devs; the comfortable ones that you can rely on to basically almost never leave - they might be interested in politics but usually it’s just skimming the surface for that little extra cash or that little promotion; and the ones that need constant simulation, that mostly play politics with themselves and are a flight risk.

Ultimately, as a hiring manager you must make a decision knowing that whatever you choose you leave something on the table.



My worry when I read your first paragraph is that you haven't stayed anywhere for long enough to see the consequences of your actions. Especially for senior positions: there's a reason why "seagull management" is a cliche.

It's a real problem, though -- as you say, there's no money or glory in building something for the long term.


> My worry when I read your first paragraph is that you haven't stayed anywhere for long enough to see the consequences of your actions.

This would be a valid concern, and truth be told I haven't, apart from on/off maintenance of the systems I built for various clients. While I agree that this is a problem, in my experience a decently built system is not going to need some amazing maintenance that only a select few senior engineers can do. It's usually run of the mill maintenance. 80% small changes to the application that realistically can be undertaken by most mid-level developers, and the occasional 20% larger changes to modules, architecture, deployment and / or infrastructure, which might indeed warrant more senior roles, and it's usually when I get a call to be involved. If anything, in my "n = 1" I have found that management is a lot more powerful in both setting up consequences, as well as handling them, than your junior / mid / senior ICs.

> Especially for senior positions: there's a reason why "seagull management" is a cliche.

I've helped build teams that are still performing long after I am gone, with mostly procedures put I consulted with, after seeing so many teams fail / win. But you are right, I wouldn't hire myself for a senior managerial position out of the box because I am just too much of a flight risk and I don't have a visible track-record for this role; I would also not disregard my skillset and breadth of experience when it's needed just because I don't tick a certain pattern.

My plan, whether stupid or not, is to continue accumulating experiences and knowledge for another 5 - 10 years (dare I dream 15?), moving to different projects (1 - 3 years) that suit my fancy, then move on and climb the ranks in a corporation from the bottom, all the way to top technical leadership. I feel a lot of companies will disregard me because I have this kind of fractured CV, but the one that won't might get a person with broad experience that also wants to 'settle down'. I am also very upfront and honest about my outlook.

> It's a real problem, though -- as you say, there's no money or glory in building something for the long term.

One of my most beloved projects (that I was involved in, not mine alone), is also one that I was paid the least amount of money on, and also I feel brings me the most glory; it involves a solution that saves lives daily. It's been running since a decade in production and the maintenance team has slowly dwindled down to only two people (one if I'm being realistic), and I don't think they'll need much more unless a revamp is required. Even though I love the project, my career would have looked a lot different if I chose to stay there and maintain the solution.




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