The kind of experience that ages well is operations and organizations i.e. knowing how to run the business, not technology. An advantage of having worked at many companies that can't be overstated is the exposure to many different ways of addressing myriad organizational and operational challenges in different business contexts in practice. My experience with technology 20 years ago is worthless. But my experience working in so many organizations and types of businesses is still extremely relevant -- humans don't change.
This is where working at a single company for 27 years works against you, it implies a lack of the kind of experience that makes older individuals uniquely valuable. There is little generally applicable skill around architecting and shipping software; the practical constraints on how those things can be done are often wildly different across companies and industries. Bright and capable people that have spent decades at a single company often struggle to effectively adapt their skills to an entirely different company context. There is practically a meme about Microsoft lifers only being able to work with other Microsoft lifers in Seattle, for example, because empirically it has tended to be true. What you don't have is 27 years of experience applying your technical skills across very different organizational and operational contexts, and that is valuable experience that only years can provide.
That isn't to say you can't, just that your experience doesn't provide much evidence of it. Anecdotally, as someone also getting up there in age, it has never been easier for me to find work.
It has been my experience that the mid-thirties are kind of a "golden window" for senior-level talent. Some people think of it as "older," but not that many.
We're old enough to have had the sharp edges worn away, but not yet old enough to make the management uncomfortable.
Once we start getting into the 40s (or, heaven forbid, the 50s), attitudes start changing -drastically. It's -sort of- OK to be a manager, but not a critical path engineer.
I will say that you seem to be an interesting chap, and I suspect that "the conventional rules" probably don't really apply to your work. Looks like fun.
For me, I like to make stuff that people use. I'm not particularly interested in changing the world (although I have, for a particular demographic -long story). I like getting my hands dirty, and Usability/Accessibility/Localization is a big deal. I like to put simple faces on complicated backends, and open tech to as many folks as possible. Most folks hate "computers," so I try to "decomputerize" tech. It's fun; especially when I see people using my work.
I consider myself to be more of a "craftsman," than a "scientist." It's a labor of Love; not just for my own satisfaction and work, but also for the users of my work. That's one reason I like working with an NPO. My whole family has been in Service, of one kind or another. My younger brother and I are the "redneck engineers." The rest of the family is a bit more Ivy League. My younger brother used to run group homes for kids that are wards of the state. He burned out on that, and became an engineer. He's worked at his [Fortune 20] company for over 20 years. It's a pretty big deal. He's self-taught, like me.
I was reading an article that said that age-compensating plastic surgery is very common in Silicon Valley, and that most patients prefer having the procedure done on a Friday, so they can heal over the weekend, and probably get away with it not being obvious when they get back to work.
New York's ageism problem (although many don't believe that it's a "problem," at all) is much more pronounced than SV (especially in Brooklyn). I'm wondering if a reason might be that NY has been a tech hub for a far shorter period of time, and we haven't had a "critical mass" of engineers "age out," yet.
I stopped going to (very good, and very energetic) NY meetups, a long time ago. It's abundantly clear that my just being there, is unnerving to a lot of folks. As I walk around the room, a big clear space automatically happens around me; like I'm in the eye of a hurricane. It's pretty obvious that I'm not usually a welcome addition to the milieux. And that's all before I even open my mouth. People don't seem actively hostile; but they avoid me. I don't get dirty looks. In fact, I don't seem to get eye contact at all.
Absolutely no one introduces themselves to me. I'm fairly affable, and have no problem reaching out to others. When I do that, we often have a good chat (although some, I can see, are looking for the exits).
Surprisingly, I often find that the people who avoid me the most, are the older members of the crowd.
That's interesting.
I can have some great chats with younger folks. I never try being "down with the kids," and I know better than to do an "OK boomer" thing. I'm a fairly good listener, and ask questions designed to encourage folks to talk about themselves, and their passions. That usually works well with younger folks.
Chris, I am approximately a decade younger than you, so in my 40s staring at 50. I started off my career at a pretty severe disadvantage, so it took off late. My golden age is now.
You are correct that my unique expertise affords me some significant advantages. For certain fascinating classes of computer science problem, I’m the person everyone calls. My true CV is far weirder than the public ones. But ironically, that isn’t what companies typically pay me for except tangentially. I mostly get paid to fix broken engineering organizations because apparently I am good at it and there is no version of “broken” I haven’t seen before. I still think of myself as an engineer, and remain extremely technical, but most days I am solving people and organization problems. I am valued more as an executive fixer than for my technical ability despite having some extremely unique technical capability. The market has made it abundantly clear which is more valuable.
I will always love writing code but it is more enjoyable as a (very serious) hobby and craft, albeit with an end product that has often been licensable. I’m not even sure this is a bad thing, since it allows a level of code quality that would never happen in a commercial environment.
FWIW, I’ve always been able to get on with young people and old people, whatever that meant for whatever age I was. I genuinely don’t classify people that way, I am more interested in their experience and knowledge. Especially for engineers, if you are doing cool shit age doesn’t matter.
I'm used to dealing with folks across pretty much all ages. I have an "eclectic" social circle that includes (but not limited to) kids still in high school, bikers, ex-cons, scientists, bankers, retirees, and CEOs.
This is where working at a single company for 27 years works against you, it implies a lack of the kind of experience that makes older individuals uniquely valuable. There is little generally applicable skill around architecting and shipping software; the practical constraints on how those things can be done are often wildly different across companies and industries. Bright and capable people that have spent decades at a single company often struggle to effectively adapt their skills to an entirely different company context. There is practically a meme about Microsoft lifers only being able to work with other Microsoft lifers in Seattle, for example, because empirically it has tended to be true. What you don't have is 27 years of experience applying your technical skills across very different organizational and operational contexts, and that is valuable experience that only years can provide.
That isn't to say you can't, just that your experience doesn't provide much evidence of it. Anecdotally, as someone also getting up there in age, it has never been easier for me to find work.