How to Know When It's Time to Go

I was not obsolete. A big company like Apple, there are always things that need taken care of.

I assumed with iOS, Swift, etc., maybe the guys on the Cocoa team were obsolete? Of course not. That code is still there, still needs maintaining, interoperability with the new languages, frameworks, etc.

I'm more surprised they want to stay on.

And that is in fact why I left Apple: the job had changed, the "career" had changed. The engineers were no longer steering the ship. It had been that way when I started in 1995 though. A "team", let's say the graphics team, would figure out what API to revisit, what new ones to add — perhaps how to refactor the entire underlying workflow. The "tech lead" (who would regularly attend Siggraph since we're talking about the graphics team) would make the call as to what got priority. Marketing would come around after the fact to "create a narrative" around all the changes to the OS. I hate to say it, but many, those were the good ole' days.

(And let's be clear, in the 90's, Apple's customers were more or less like the engineers, we also loved the machine for the same reasons they did — so we did right by them, made changes they would like because we wanted them too. You can't say that as convincingly for the phone, being a mass consumer device.)

Marketing took the reins long ago though — especially as Apple began to succeed with the iPhone (which, someone can correct me if I am wrong, but I think was an engineer driven project initially — I mean most things were up to that point).

I stuck around nonetheless though because there was money to be made and kids still to raise.

When the last daughter flew the coop though, so did I.

The problem is, I have a family and finding fulfilling work that you have no experience in, in this country, at 50, is close to impossible.

So for now I consider myself lucky and try to rediscover the fun things in programming.

Right now I feel like I'll never want to stop making things, but that if I were rich enough and good enough at creating in a different medium other than code, I completely understand the desire to walk away from the terminal and never look back. Few things have been as frustrating to me as programming. Yet since few things have been so rewarding, I persist.

It's a great article because it's making me think about my own life. I'll keep pondering. Thanks for posting it.

Instead I now program in a great language, Elixir, working on projects that I want, and reading books that I’ve been putting off for decades.

Can relate. I've been "retired," since I was 55, and SV was nice enough to let me know that I was too old to play in their pool.

Pissed me off, something fierce, but, in the long run, it's the best thing that ever happened to me.

I could have made millions -for other people- maybe for me, as well, but I have never really been interested in that kind of thing. The work and the technology has always fascinated me.

I've found that what I really enjoy, is making UI tools for nontechnical folks. That's what I do, these days. I make free software for folks that can't afford the kind of stuff I do.

https://www.youtube.com/watch?v=nQxsG9Vcndw

There's also a Guy Lombardo and a Louis Prima version but I like this one.

I've been singing this at work for a year or so, trying to give people a gentle hint about my future.

> It's not worth working and being miserable.

Agree 100%. I've quit several jobs after the environment becomes more stressful than fun. Over the years my tolerance for BS has lowered, possibly to the detriment of my bank account. But I've never regretted my decision to leave. The weight off my shoulders is priceless.

> Age and ability are not correlated.

I wonder how subjective this is. Cognitive decline with age is real, but maybe keeping the brain active with programming can help keep it at bay. A study about this would be interesting.

I like programming computers, but just not 2000 hour a year. I can afford not to do that, so I don't.

I hit a point in my 30s where I could sock away a year's worth of savings in 3-6 months of contracting, so that's pretty much where my full-time phase ended. I came back "out of retirement" when the first kid was born and worked 5 years semi-fulltime to save up enough for houses, college, etc., ramping down to 4 day weeks for the last few years because I really value my free time.

Since then, I've done the odd 3-6 month/year stint (since programming and working on a good team that can ship is still pretty fun.) Recently I've been doing that part time, 2-3 days a week, a few months a year.

I don't know what most people would call my situation. I call it Retired as I want to be at any given moment. I expect I'll keep doing it for the dozen-odd years between now and when I hit "Retirement Age". But maybe not. It's almost more of a hobby at this point.

I guess the point is that it seems like a silly idea to do something all day every day for most of your life, then suddenly drop it completely. If it was fun, do more of it. But on your own terms, and only enough that it's still fun.

Ha I know lots of retired programmers. I was one for a while, but like most I really wanted to get back to work

It's been a challenge for me to adapt to the new reality of coding as a game of busy-work and lock-in through complexity.

It has become a bit of a theatre for me, unfortunately. I know I could do something in a way that's 100x more efficient but it would negatively impact my job security so no thanks. Also, if I do the right thing, taking all the risk upon myself, nobody will appreciate. I'll stick to inefficient popular tools and methodologies. I'll play the game of Whac-a-mole... Like a bad gardner who pulls the weeds out by the leaves and leaves the roots behind. That's the smart move.

I tried the other approach, doing my very best, outperfoming and it couldn't have worked out worse. The manager class feels nothing but contempt for people who outperform. "Good boy! Here, have a pat on the back... Sucker."

But I'm basically semi-retired to a degree in my field. I'm doing the bare minimal to get by at this point. I ultimately would love to quit some day, and pivot into a different career, not entirely related to coding. I'm not at that point yet financially though, and am spending energy elsewhere

I would love to start a non-coding related business one day though.

I have more Project experience but technically I dont know much more about Cloud, JS frameworks, modern DBs etc than someone 30 years old. Ironically my main advantage seems to be I can focus more and work longer hours than younger people who seem to value WLB much more than we used to.

A former boss of mine retired early once he decided he was done with the politics required to navigate his work. He fully unplugged from corporate life and got comfortable delving into his passions... cycling, woodworking (so much woodworking), etc. He seemed to be having a blast from what I could see. I recently caught up with him, and it turned out after about a year off, he'd just accepted a job at a fintech that his former boss reached out about. I guess for him it was time to go from that specific job but maybe not quite from engineering in general.

I do get how you can burn out, especially on the business side of things. A lot of jobs just aren’t important. The trick is to avoid them if you can and leave them as soon as possible if you can’t. Every non-startup / non-economic boom job comes with some degree of Kafka, and you’re either going to learn to not care about it or go crazy. I’m not sure that is especially unique for programmers though, this seems to be most things. Unless you’re extremely talented at the HR part of organisational politics (which most programmers aren’t) you’re also going to have to build some really stupid stuff during your career because change management is hard. So hard that it’s virtually impossible for talented HR staff to do when the direction is upwards, which it’ll always be for programmers. Again, it’s something you either learn to laugh about or burn out on.

The change in technology, however? Isn’t that part of the fun? If it isn’t, is that because you don’t have the time for it? Because if don’t (and a lot of jobs won’t give you this) then you’re frankly in one of those “leave as soon as possible” positions. Even so, niche work rarely dies. The author mentions mainframe work, but mainframe work is still some of the highest paid work in the world because those grey beards who actually know and want to do it are so retired that a lot of them are frankly dead. I’m not sure how you could ever work on mainframes for 40+ years and then not be able to get paid handsomely by banks.

Anyway to each their own. It’s a nice perspective, and it offers you a few insights into just how much of a cog in the machine you’re going to be in virtually any job. Even one where you’re extremely well liked and rewarded. I think the best thing I learned from my stint in management is how everyone, and I do mean everyone, is replaceable. It’s just a matter of cost. Which can sound depressing, but it’s also very liberating because it teaches you to not get overly attached to jobs or employers.

Ended up hanging around for a year effectively working part time. Not sure that was the right idea or not (had lots of vacation which I pretty much all took) but year+ passed by and it was pretty obvious at that point I couldn't drag my feet any longer and didn't have the interest or need to do a job search.

"If the struggles outweighs the pleasure you should stop doing it".

I heavily relate to this line in the article:

> Some time ago, I knew a programmer with the same number of years of experience as me. Yet he seemed unable to comprehend what was required of him, and I had to review everything he wrote because it rarely worked

I made some of these mistakes. I didn't have anyone to help me avoid them. Now I can help but .... I cannot help. Only after the balls up and even then often not.

If I had a nickel for every leader I've worked for who didn't know when it was time to go... I'd have 3 nickels, which is still a surprising amount

And if I’m lucky enough to get laid off (around retirement time), that would be a huge windfall to move me toward retirement.

Programmers planning to work after 50 are fools.