Ex-CTO here. A CTO doesn't have to be a people manager. It certainly makes it easier to staff pet projects if you have direct reports (rather than having to convince a VP Engineering to give you resources). But just know that many CTOs (especially co-founder CTOs) focus on technical vision & strategy, being the engineering representative in the C-Suite and vice versa, overseeing architecture and innovation, and perhaps even write code. As the CTO you should be able to decide how many meetings you need to be in, and for that matter you could set policies that eliminate pointless meetings across the board.
Ask HN: Senior people, how did your career evolve?
41–50 of 53 posts
Re: Ask HN: Senior people, how did your career evolve?
#42I'm about 12 years in myself and can provide some thoughts on this, though I'm not 20+ years senior. My first few roles were in startups, where I got to be very hands on, learn a bunch, and mostly focus on the craft of software development and systems. I similarly felt I had a lack of higher-level understanding of business, management, product, etc. I then went to Amazon for 7 years and this is where I felt I develop…
What you say makes total sense. But for some personal reasons the social part of the job has always been my weak side and I'm just not interested in playing that game. I've had fairly positive successes in the past when being a contractor. I feel like it's easier for me to have legitimacy and influence over the project that I'm doing this way. > Lastly, make sure whatever it is you work on truly matters to the busine…
I can try to expand on this a bit, and respond to your thoughts.
> What you say makes total sense. But for some personal reasons the social part of the job has always been my weak side and I'm just not interested in playing that game.
I don't mean to imply playing politics or empire building. I've probably capped my career in some ways by not playing into that either. However, in roles I've had, I've built up good capital by being very helpful, jumping into incidents, etc. There are ways to build that social muscle without it being negative or selfish.
> That's something I have also learnt from experience, and I am more often than not the one pushing for boring tech against the last fancy trends.
I think this is valuable, and it has worked for me as well. Though the eternal struggle of taking on debt for speed is fundamental. By building up some of the social capital and trust, I think it makes navigating these discussions easier and being able to negotiate in time for projects to do things right. That's the only way I've found this piece to be successful.
Re: Ask HN: Senior people, how did your career evolve?
#43In work life as in the rest of life there is a mid-career crisis thing where you plateau and realize this is likely the best you will ever do. Crazy things can happen or you may float until there's a downturn and/or layoff but likely at some point the same old same old may appear to be a friendly shore you would not mind landing back on to finish your career. A side hustle can be a good way to do something you feel passionate about.
Re: Ask HN: Senior people, how did your career evolve?
#44It seems clear to me that you need to be leading now, not being a cog with no influence. I also resisted "being a manager, for a long time. It's like it was a dirty word and I thought it would be turning my back on what I was good at and enjoyed. But the truth is, you are no longer enjoying what you previously did and have not grown for 5 to 10 years. Being a leader is not being a line manager. Managing some people m…
Thanks for the insights. But I've already been at this kind of position in the past (tech-lead role involving managing the devs). I hated the management part and even had to recover from a burn-out of a huge and messy project. Also I care too deeply about the quality of the software being developed and am very much perfectionist, which usually translates into lots of frustration for both me and the team.
Honestly, I'd say you need to try working with more distance from the devs and work at a higher, more strategic level.
Instead of worrying about how a particular bit of software is built, you should be creating better ways of building. Enhancing processes, making the technology better, improving how dev work is delivered, rather than the minutia of a single development project.
Being a perfectionist tech lead directly managing the devs on a project sounds exhausting for yourself and the team.
Re: Ask HN: Senior people, how did your career evolve?
#45I think it is going to be difficult for you to get advice outside of the herbal "find a job you like, live a full life" I am working for 30+ years, a combination of academia, then tech until today, where I have a very senior position in a company you know. The world changed drasically over these 30 years and my path to an arguably successful career is absolutely not what I am suggesting to my children. My generation…
I’m not sure if this is good advice. The problem is that tech fashions and job market change rapidly every few years. And it takes a long time to specialize in an area. If you’re lucky and happen to be in the right place at the right time, sure, specialization works for you. Otherwise, there can be no job for you as a specialist. If you start early, who knows what the job market will look like a few years from now, l…
I am not sure either if this is the right advice, this is just my view over a convoluted 30+ years career. I have two children who are in the middle of their studies now and I had the same concerns suggesting a path.
I will try to expand a bit.
There are manual jobs that are very interesting and work well until 40-50 years old.
An example is physiotherapy, where you can concentrate on more dynamic activities when you are young, and move to softer ones later. With the demographics in Western Europe, you are good.
Another one is electrician: it is constantly evolving, with major shifts such as home automation and it is reasonably physical (the added value is that you do not keep a static position for the whole day).
Importantly, none of the above is at risk with AI or shifts in the market. You always need people to help you physically and you always need electricity. On top of that these jobs are regulated so you can't be short-cut.
One of my kids is going this way and it is great.
The other one is in Finance, in the best and most competitive school in the world. I see his future as bleak, something I would not have even thought 30 years ago.
He will live in slavery for 5-10 years, doing insane hours and without a social life at the moment when it counts the most. He will make heaps of money, without real opportunities to spend it. And he realizes that.
As I said, 30 years ago it was unthinkable, at least in my country. A diploma from that elite school was the real way to everything. Your year mates where the future ministers, president, head of national or international institutions. And the weird few who would go for NGOs.
All this means that any advice a 50yo will give is heavily impregnated with their past and that past (which was their future when they were young) is fundamentally different from the future of current youngsters. We do not live in an era of fundamental changes as we did in the 90s.
Re: Ask HN: Senior people, how did your career evolve?
#46Earlier quoted context omitted.
I’m mid 40s and took the other route. I was self-taught and decide long ago that I never wanted to manage other people. So instead now I run a small solo audio company. Never have to deal with anyone but my own customers. I consider it a craft not a startup. It isn’t for everyone but whatever LLMs end up being for us all, in this position they seem more likely to be an asset than a liability. If they are good enough…
Mid 40s consultant here and just decided not to extend my contract as tech lead with current customer for another year. Looking into meandering for a bit and regaining passion. Hopefully something small but sellable sprouts from that. Looking forward to making my own decisions based on gut and not being stuck in the swamp of big company indecision.
Got any idea what sort of tech you’ll mess around with?
Re: Ask HN: Senior people, how did your career evolve?
#47If you've not already done so, peruse the Staff Engineer¹ website and maybe get the book associated with that² or another one that I like³
It's not clear to me if you have a role with that kind of title, so if not, see if that path appeals to you.
Speaking for myself, I find that the type of colleagues I have are the most important factor in how much I enjoy my work and how much I can get done (impact). It can be tricky keeping space for hands-on work in a staff rôle though.
³ https://www.oreilly.com/library/view/the-staff-engineers/978...
Re: Ask HN: Senior people, how did your career evolve?
#48Focusing on software engineering IME isn't that great, there's only so many variations of frameworks/programming languages that can keep me interested.
I'm usually more interested in solving business problems, then I work on industries or companies that are doing interesting things. I've worked in the hardware industry, cloud start ups, visual effects, and now AI.
I feel very satisfied pushing those industries forward with technology, basically the technology being a means to an end.
I usually join the company as some senior dev (more recently already joined as snr mgr) and end up in leadership roles - which seems to be at odds w. what you want.
Re: Ask HN: Senior people, how did your career evolve?
#49It seems clear to me that you need to be leading now, not being a cog with no influence. I also resisted "being a manager, for a long time. It's like it was a dirty word and I thought it would be turning my back on what I was good at and enjoyed. But the truth is, you are no longer enjoying what you previously did and have not grown for 5 to 10 years. Being a leader is not being a line manager. Managing some people m…
Thanks for the insights. But I've already been at this kind of position in the past (tech-lead role involving managing the devs). I hated the management part and even had to recover from a burn-out of a huge and messy project. Also I care too deeply about the quality of the software being developed and am very much perfectionist, which usually translates into lots of frustration for both me and the team.
> Also I care too deeply about the quality of the software being developed and am very much perfectionist, which usually translates into lots of frustration for both me and the team.
This is at odds with business needs, very usually. So it doesn't surprise me that you feel people don't listen. Very few business are making money trying to pursue perfect software or quality software - if any.
Like security, trying to be perfectionist won't move any business need/project forward as we all have the real world to deal with, constraints on time / budget / scope are part of decision making
Re: Ask HN: Senior people, how did your career evolve?
#50Becoming a developer.
I was an experienced visual web designer. A few months after joining Travelocity I was involuntarily reassigned to a UI developer position. If I wanted to stay employed I had to learn to program. That first year I was shitty at it, occasionally broke stuff, and received a negative annual evaluation. This was 2008.
Shortly after that the economy collapsed. There were massive layoffs and a lot of good people were fired. I was not one of the good people and I was not fired. Before jQuery became an obsessive religious cult UI developers were tough to hire. The world was full of UI developers that were so much worse than me. Super incompetent was the industry performance average.
Learning to program for real.
In 2009 I was picked up for my second military deployment. I am a soldier in the Army Reserves and spent the next year in Afghanistan. In Afghanistan I learned to program for real by writing original applications. After a year of grinding I was still shitty as far as being an actual application developer, but I was orders of magnitude superior compared to the average corporate JavaScript developer.
My first career mistake.
I managed to pick up the CISSP certification at the end of that deployment. I should have done the work to transition my career to cybersecurity, but lacked the confidence to figure that out. I had a guaranteed job waiting for me Travelocity so I went back to the childish career of web developer.
I received 3 raises and a promotion the year I returned to Travelocity. I became a senior when I became the company experimentation engineer for A/B testing.
My second career mistake.
In 2014 I came back to Travelocity after another year in Afghanistan. At this point Travelocity began to internally implode so I left to explore other opportunities. I should have stayed at Travelocity. Instead I bounced around the market getting small raises at joining each new employer.
As the years went by I continued to become more experienced almost entirely due to challenging side projects. The career became progressively more shitty as my average peers seemed progressively more child-like and progressively more fearful of writing code.
After 5 years at Bank of America I left there for a work from job for a small company with complete garbage for internal code. I didn’t even make it a year before I was laid off. I made a promise to myself to never go back to the toddler daycare of JavaScript employment.
I was picked up by a defense contractor to do work on enterprise API management. Within a year the promoted me into management involuntarily. This is my current job and it’s been amazing. The people are so much more mature that the comparison is beyond words.
I wouldn’t go back to JavaScript stupidly unless it’s vanilla JavaScript work to guarantee I would be working with decent people or $500,000 to compensate for working with arrogant children.