What is your biggest career mistake? What did you learn from it?

Staying in the same job for too long, I felt comfortable and had lots of control over what I did but no job is forever and eventually it will end so be ready for it.

My skills atrophied so it was very hard to get a new job once I had to look for one.

Tech moves fast so you need to keep up to stay competitive or work your way up the career ladder. The best way is to look for a new job. If you're lucky you can do it within the same company.

Side note: I believed that by focusing on my tech skills, I would be promoted. Big mistake, tech skills are a small part. You need leadership and relationship skills which are a huge part of getting projects done.

Not allowing myself to be more like George Clooney, at last as relates to working for unethical / sleazeball / just plain dishonest employerss:

Unruffled as the silver hair on his head, Clooney leans forward, as if he is about to confide in me. “Well, yeah. I was offered $35m for one day’s work for an airline commercial, but I talked to Amal [Clooney, the human rights lawyer he married in 2014] about it and we decided it’s not worth it. It was [associated with] a country that, although it’s an ally, is questionable at times, and so I thought: ‘Well, if it takes a minute’s sleep away from me, it’s not worth it.’

https://www.theguardian.com/film/2021/dec/03/i-was-offered-3...

Do I really have to pick one mistake?

- I accepted an ever increasing span of responsibility without commensurate increase in compensation or real authority (promotions).

- I deceived myself into believing that giving up vacations, personal time, education, working through illness, etc was ok because “senior executives” were asking me to do so and I was a “critical team player” in the corporation's success.

- I didn't appreciate until too late that as a technical person in a technical role in a non–technical organization I would be evaluated on KPIs/OKRs/PBCs which were important to the non-technical organization but meaningless to technical peers and useless when trying to move on to future roles.

Oh man I can think of so many I’m not sure.

- Accepting the first offer I get. Hell I still do this, mostly because if the money is right, I get sick of interviewing. Not doing this likely could have yielded me the money I’m making now, years ago.

- I think the biggest mistake though wasn’t even really intentional. I just didn’t have a good enough understanding of the files, and the intricacies, strategies, and realities of having a career in the field. Looking back, I should have just grinded leetcode and tried for FAANG from the start. I’m stuck in a certain, generally disliked sector of the industry and getting out is very difficult. No one seems to be interested in anything I’ve done except for my past professional work history.

Listening to the likes of Gartner.

They pretty much said words to the effect of software development would all be outsourced to India back in 2001 and I took my hands off the keyboard and focused on the process side of things.

Fast forward 20 years and devs are in crazy demand.

Probably not working a more different types/sizes of companies sooner, and on a related note working at one company too long.

I think the best thing was probably going into a co-op program. I worked at so many places and got to do a lot of interesting things. Interns often get handed great misc things that full-timers are too busy doing big projects to do.

My greatest mistake was going into consulting, it really did not suit me at all. I was also really bad about doing paperwork which is required to get paid, keep up on giving the government their due, etc. It paid a lot, but not learning as much in that time isn't worth it to me in retrospect.

Discovering working at growing startups was very refreshing. Get to/have to do many things fast but still well if you have any sense of craftsmanship or empathy. At first wrote off, and eventually found that a larger company can still do decent engineering and offer a great work-life balance and challenge. Unless a startup keeps growing at a good pace, usually top-out/get bored and move on in about 2-3 years. When bored, side projects to try out new stuff either at work if you can, or at home helped.

Even working at multiple companies being too focused on my favourite language/framework/stack at any given time wasn't that useful. Accidentally getting into other langs/frameworks was worthwhile and so should have been more open to them sooner. I'd still like to know how using OCaml/F# on a real project goes.

There have been two major fork-in-road decisions that I have taken and I do not know whether they were ghastly mistakes or the correct decision: (1) Switch from development into technical marketing. (2) Switch from scientific software to general software development. I didn't take either fork and while I like the result, "the grass is always greener".

On a larger scale, the choice of a scientific PhD vs. a CS masters was an earlier/larger decision. Again, I went with the former and remained in the smaller pond. Others might view this as a mistake and it was from a $$ perspective.

Finally, after some time as a project leader, I returned to the bench as it were. I prefer doing rather than talking about doing, but that's also a power and $$ loss if that's what you're into. But I managed, for the most part, to do what I wanted to do. Yeah, I had to move more than we wanted, but that turned out ok.

Work is what you do to have the resources to do what you want. If you fully identify with work, then how can you retire or exit the game - you would have no identity?

When grazing youtube, look for Lennon's quote in Yesterday about living.

I think that a really big career mistake that some people make is changing jobs in a lateral transfer when you should be looking to a position which represents an increase in responsibility.

This doesn't mean a title change as in Programmer to Senior Programmer --titles are often bullshit-- it means changing from a staff responsibilities to a lead responsibilities or lead responsibilities to executive responsibilities.

Staying at the same position too long and allowing myself to become bored at my job. I naively assumed that if I was performing well with my technical skills that I would be handed more interesting projects but that certainly wasn't the case. It seems obvious now, but the biggest lesson I learned was that I needed to put time and effort to steer my career in the trajectory that I want and that I wasn't as stuck as I thought.

Not understanding, "good enough".

I am a hard worker. I was stressed down the years managing a busy infrastructure. I made success too much about me. If the network was a problem, I was the problem.

I now work in education and realise that sometimes good enough is just getting through the day. I can give the greatest lesson ever. This won't stop one of my students making farting noises.

I wish I had more good enough days in saas as networks fart too.

Not studying computer science at a prestigious university. Missed out on a lot of career head start by not doing so.

Not going solo earlier. I earn more, work less and no one bats an eye if I change assignments every 6 months.