Almost three years into my job and haven't been fired yet...is it time to move on anyway?

The top technical guy at our division got laterally moved to an executive VP position. I think you have to be a lot better to get to that level on a technical track than a management one, but I’m biased.

It depends on the culture. Some places prefer to promote from within, some prefer to hire. I’ve never worked at a place with partners so I can’t comment on that.
My son-in-law is definitely in a high management position in a Fortune 50 company, which he moved into from outside.
None of this helps in deciding what is a good job, but I’m not sure anyone can help with that.

New York does has a pretty big and diverse market. Well diverse in different flavors of finance or tech or fintechs. But it’s also insanely expensive and competitive and sort of makes you feel like you screwed up if you aren’t making a million dollars a year. Or perhaps more accurately, since I’m not making a million dollars a year running a hedge fund or whatever, I don’t really need to be in NYC.

I’m not sure your “build/consolidate/protect your career” model actually works all that well. Yes, in your 20s and 30s you should be building up the skills, education, contacts, and experience to get established.

By your 40s, you should have established some degree of seniority and credibility.

The questions is, how does one “protect it”? I think maybe for one, it’s not giving the appearance that you’re the “old guy” digging in and just protecting your career so you can ride it out until retirement. I think you need to be constantly building your career.

let me expand on that / rephrase it:

in your 20ies or early 30ies … you might agressively pursue carreer changes every 2-3 years and move into a riskier “make me or break me” position - b/c when things go south, you normally rebound faster/better being a single and eating ramen for 3 or 6 months than being 50 and having to pay for 2 kids in expensive schools and a mortgage on the newish house.

Being beyond 45 (used to be 50) … and making a bad carreer move means often that you have to ride it out - often for years … as your options are no longer so great.

Again, that might be less of a problem in a constant-movement, mercurial jobmarket like NY, but in other (less “liquid”) jobmarkets you do want to take extra care to not paint yourself into a corner with a job-change …

I think it’s sometimes hard to tell if you’ve “painted yourself into a corner”. I’ve had a lot of jobs over the years that seemed promising but ultimately didn’t pan out for one reason or another.

Plus people often don’t have a choice whether they get laid off or restructured out of a company.

I’m on a new long term project now, so I’m inclined to ride my current job out a bit longer. Because all things being equal, longevity looks better than job hopping IMHO. Unless of course you are just doing the same dead end bullshit day in and day out (which I don’t believe my job is).

But 50 or not, I do feel like I need to evaluate whether my company will be stable for the next couple of decades. But then who the fuck knows that shit these days.

True, true.

So you have a Plan A if you can keep working there, but you keep your eyes open for a Plan B in case you want/have to jump ship.

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That sounds like something from my dad’s generation.

He was in WW2, and worked in the same industry for his whole life. So I’m in my '70s. But even I had a much more flexible “career”.

Well, “careers”… from medicine to ministry to media producer to designer to creative director (ad agency) to art teacher…

Some changes were because a firm went under, some because I really wanted to work with specific people, and the last one because I was working 60-80 hrs/wk and wanted to get to know my kids.

I owe a lot to a flamboyant ad guy who’d help with our high school church youth group. He told us not to expect loyalty from a company, and that our only “job security” would be our skill sets. The more diverse, the better. That advice made a diverse work life a lot more fun!

Exactly.

And FWIW I’ve changed jobs 4 times since turning 45.

The problem with the “collection of skills” model IMHO is that it does position you to be an interchangeable cog. That is to say, yes, you are employable if someone needs a particular skill set. But you’re just as fireable if the needs of the business change. Plus you end up in a commoditized pool of people with similar skills. I see this a lot in my profession with IT resources. “I need a java developer” I need a big data cloud specialist".

What makes career changes challenging as you get older (IMHO) is that there often needs to be a business case for hiring someone with 20 to 30 years of experience. Like you probably should be at management level or at least had management experience (at which point it’s less about your collection of skills as it is demonstrating your ability to make organizations successful). If you’re not management, then you maybe need to demonstrate something like 20 years of solid relationships (if in sales) or that your a freakin’ grand master at whatever technical specialty. And if you’re not one of these things, a hiring manager might be inclined to wonder why and if they weren’t better off hiring someone younger (and cheaper) who might be better positioned to grow into the role.

I think this decision is being made WAY before a hiring manager enters the picture.

"We need a full-stack-scrum-master-black-belt-six-sigma guy and can pay a yearly remuneration of $50,000.00 … "

→ With a brief like that, the hiring manager never gets to see somebody w/ 20 years of experience

So, the gatekeeper is already implicitly the brief, not the hiring process.