Posted by TheAlchemist 1 day ago
I've been a DevOps/SRE essentially my entire career and almost always in Finance (banks, FinTech startups, multiple hedge funds etc) and most recently in crypto.
It's seemed that for SWEs the path was always something like:
- junior
- team lead
- manager
- manager of managers
- CTO (or VP of Engineering etc)
For SREs/DevOps it always felt a bit fuzzier after manager and most of the manager of managers I know ended up being that role in an "infra" department (e.g. k8s, networking etc).
I would love to know what folks with my background ended up doing later in their careers/age mid 40s and above?
(all of this is even more fuzzy due to LLMs/AI and part of me feels like it's time to start pivoting into some kind of IRL service or manufacturing role given the speed at which things are developing. e.g. maybe I should buy a bakery...)
Open to all kinds of stories and suggestions here as would most likely benefit me and also lots of other folks reading the comments.
I'm 41 now, started working in education but pivoted back to tech quickly (DevOps specifically) since tech is a better match for me.
After a few years, fell upwards into management then pivoted into Technical Program Management roles where I've remained since. Love this since I get to interact with teams of people working in my program(s) but don't have the responsibilities of a people manager.
Personally, my roles focus on infrastructure and things at least loosely related to my DevOps background. Worked at two blockchain companies (I've been into blockchain tech since 2012) but considering moving into green energy somehow.
I think in most cases including yours: choose roles based both on interest and total compensation. And it's a lot easier to get roles (especially TPM roles) if you're already technically competent in that particular field (in your case FinTech and crypto).
What helps me is keeping around my TODO.txt month by month, as well as a lot of screenshots and images of the things I find relevant for sharing in stand ups and meetings and such (as well as presentations).
So if I need to review the past month/year (e.g. when I want to update CV/site or catch up with management), it’s just a matter of going through a bunch of text and images without a lot of unnecessary fluff, like digging through Jira. Maybe if I want to get the approximate time/effort spent on particular stuff, based on the amount of activity there.
Alongside that, it’s also nice to document stuff that was particularly good, or all the ways software broke in (and what broke how often), as well as stuff that pissed me off and made me want to quit (sometimes people/mindsets, sometimes tangible code or practices).
When the default is just going with the flow and not documenting anything and doing no self reflection, every improvement upon that helps.
Typically I'll have a folder with a bunch of numbered files in the order that I want to talk about them, since it's easier to just quickly share my screen and run through then when I want to let others know what I've done, for example along the lines of:
01-migrate-gulp-grunt-to-vite.png
02-vue-prebuild-script-check-unused-translations.png
03-java-add-compile-memory-limit-ide.png
04-server-update-python-for-ansible.png
...
The job market and my visa status meant that it's either impossible or I need to make significant sacrifices.
So that's life.
Now that our kids are grown and self-supporting, it's wild how much simpler the risk calculation is. But at 52 with engineering manager being the dominant role in my CV, not particularly appealing to the small companies making big moves that I'm interested in.
Reminds me of PG's "How To Do What You Love"[1]
I've seen fear as the primary obstacle to trying something different when the current route is not working. It's really hard to step outside the comfort zone in those situations.
While you definitely need a higher than average tolerance for uncertainty, the big thing is just not seeing all the options. Many choices are occluded by the options presented to you by employers, the educational system, etc. The spectrum of careers, which is a continuous higher-dimensional blob of "things you can do to make money", is systematized in such a way that while there are paths to unusual career outcomes, most of those paths can not be expressed.
You may on some level want to reach some career or lifestyle goal, but often the path to that destination isn't obvious, and it's definitely never presented to you as an option among the things you can choose, and more than likely you'll have few if any role models or people to ask for guidance if you find yourself on that track.
What people need aren't more options. What they need is MONEY; which is the ability to obtain the options which exist. And the only way to give people more money is through political means. This is why I was interested in crypto; it seemed to get straight to the point...
I later quit crypto due to too much corruption in the space and launched a mainstream startup with a co-founder centered around helping people find 'the perfect job' but I quit as co-founder because the idea of it almost makes me want to vomit now.
The system is firing people en masse. The system itself doesn't want people to have jobs... So me, trying to work against the system by offering a solution that operates within the system feels futile and like gaslighting users and myself. It's selling a dream. There is no perfect job. Reality is our socio-economic system doesn't even have a shitty job for you... Let alone a perfect job... And most jobs seem like bullshit jobs anyway.
It's extremely hard to find an idea that's both truly useful and profitable these days. That's a shame because that's exactly what I want to do with my life but I feel like this does not align with what is possible within the current system. I cannot find any such opportunities in the tech sector.
Someone told me I should get into politics but again if I think about what the typical politician does, I feel nauseous. The only kind of politician I could possibly be is the honest kind that gets assassinated... And of course I don't want that. Besides, nobody would fund me... My hitman would probably have an easier time raising funding to 'take me out' of politics than I would raising funding to get into it.
I need to integrate with tools that prematurely deny me because I'm not a big company. I basically already lost, despite my tool being much more reasonable and maintainable (I've worked at the competitors and it was a mess).
The world doesn't care about good products, they just care about how it looks. Big companies look good, you don't. It got me demotivated early on. You really need thick skin to start selling a product.
I also think it's true; what appeals to people is something superficial. The product has to be highly optimized to generate an initial 'wow' factor. But it's almost impossible to create such 'wow' factor without sacrificing something fundamental about the product.
The goal is to make such a good first impression that people will pay for your product and then will keep convincing themselves and their friends that your product is great... When it's not because actually there are many better alternatives out there which are higher quality and provide more flexibility.
Among financially successful products, I see a lot of rigid, inflexible, low-quality products. They create a 'wow' factor by removing complexity; also removing flexibility... Targeting a specific psychological bias... These products seem 'easy' and magical at first but what makes them easy also makes them inflexible and fundamentally useless. Because flexibility is what gives a competitive edge... But flexibility also scares people away.