I'm in a bit of a jam career-wise. I'm afraid if I don't take some aggressive actions, I'll be one of those thirty-year veterans who can't get a job in their early fifties. And I'm sure there are plenty of other "senior" people with this problem. I need to get in a new position where I can grow technically, but my current resume leaves me with few options that do not involve a step down.
I've been a software developer for 20+ years and am employed in a small company with about 20 engineers, where I've functioned for some time as technical lead and manager. But at this point, unless the CTO vanishes, I have nowhere to go. And I've spent over ten years here. Meanwhile, having spent two years looking for other job opportunities, I've come up empty; with my leads running out, I'm now extremely concerned about my employability outside of the company.
The main problem seems to be my lack of "hot" skills and the fact that the stack I'm working on relegates me to a limited number of opportunities. The company is on an all-Microsoft stack and that's not going to change. Unfortunately, in the area I'm located, I'm having a harder and harder time finding interesting opportunities in that stack. The main business here, technology, finance and media, have all moved strongly into the Linux camp, and I'm having difficulty finding opportunities on my present stack that will not be even more limiting.
It's been a while since I had to transition to a new stack. As an intermediate developer, I had no problem finding opportunities; if you show you're capable and can learn on your own time, it's easy to get over the hurdle. As a senior person, looking at senior-level jobs, I haven't been able to do that. I've gotten quite far in interviews with a handful of companies who like my tech lead/manager skills, but I haven't been able to "seal the deal." When it comes right down to it, if a company is prepared to pay top dollar, they're also prepared to wait for an exact match. These means a match on the technology stack, even for managerial positions.
Given that, what is the right approach for pursuing opportunities on a new technology stack? The most obvious route is for me to take on a large side project, but it's an awful hard sell to my significant other to say "I'm going to spend one day every weekend over the next year on a side project that will qualify me for a job that will be a $40K/year pay cut." Has anybody been able to successfully navigate this? If you've done this successfully, I'd love to hear your experiences.