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Re:How do you handle your Aging in IT? by prewett on Monday February 01, 2021 @06:21PM (#25995501)
You might consider contracting. I've been doing that the past few years and loving it. One of the things is that I get to (have to, in fact) choose my projects, so the clients I say yes to are ones whose projects I am interested in at a level beyond just "you'll pay me". They also tend to be in my specialties (UI, graphics, C++, iOS, in my case). I find that I learn a lot more, too, because generally the projects last about 6 months, and inevitably they use things I don't know about. In the past few years I've learned: TypeScript, WebGL, WASM/Emscripten, CMake, "github workflow", pybind, basic Ruby, basics of physically based materials (PBR) rendering, new UX patterns, how to convert Bezier curves to renderable line segments, basic image processing with OpenCV, Dear ImGUI, and vector graphics with OpenGL. I did not know any of these when I applied for the contract in question (in fact, a contract I thought was going to be a C++ or at least C# contract ended up being TypeScript, which was a tad scary for a day or two), but they start to accumulate and make me even more valuable. I think being a generalist as a contractor is an advantage, it gives more areas where you can demonstrate "I did this". I also think clients value age in a contractor more than employers do in an employee, because you can show a long list of similar things you have delivered and it's clear that you have experience successfully solving problems like yours.
Re:How do you handle your Aging in IT? by throwaway98az8 on Monday February 01, 2021 @06:46PM (#25995728)
Any advice for how you bootstrapped this and started to get clients? I find that the hardest part about taking the leap and leaving a full-time role.
Re:How do you handle your Aging in IT? by prewett on Tuesday February 02, 2021 @11:03PM (#26010472)
The easiest way is with an agency. I've used Toptal a lot, and moonlight.com seems promising. I had a really wonderful client through the HN monthly freelancer thread. My current geographical area does not have much in the way of software, so I probably need to move to get local clients.

I would normally worry about finances, but I happened to be forced into it due to some (non-tech) classes I wanted to take, which was helpful because I'd already decided I was going to be burning money that year. And the previous year I was working on an iOS app on my own in Asia (= low cost of living), so I'd already discovered--a little to my surprise--that the sky didn't fall in if you don't have an income. I've discovered it usually takes me about a month to find a new client, but I'm sure that depends on the developer, experience, and subfield. If I wanted to do webdev it'd probably be a lot faster. If you want a conservative plan, I'd recommend saving 6 - 12 months of expenses, line up a client with the understanding that you would not be able to start for 2-4 weeks, and then quit. Or maybe you could arrange with your company to transition out more gradually. At some point, though, the water isn't going to get any warmer, you just have to jump in the pool and scream underwater for a few seconds until you get used to it :)

Re:How do you handle your Aging in IT? by nickthemagicman on Monday February 01, 2021 @10:09PM (#25997050)
Agreed. I think just about anyone would choose to work for themselves if it was easy to get the clients if I'm not mistaken?
Re:How do you handle your Aging in IT? by Damogran6 on Tuesday February 02, 2021 @12:10AM (#25997632)
I was temporarily under employed and called up a contracting firm. (Robert Half, experience was fine.)

I had an income 48 hours into the experience. You’re expected to know what you’re worth, but there’s a certain freedom and nearly none of the job hunt bullshit.