I’m still in my twenties (barely) and confident enough to say that I’m not mediocre at a couple skills at least. I have worked in several jobs both supporting “

I’m still in my twenties (barely) and confident enough to say that I’m not mediocre at a couple skills at least. I have worked in several jobs both supporting “legacy” business needs, and at a couple startups. Two things: First, I think you’re being unreasonably pessimistic. I know programmers who just got started learning the craft in their forties, without any special aptitude for the work, and they’re doing fine. If I wasn’t hand-crafting custom stacks for my work now, and had less ability to do so, there would still be an enormous demand for just stitching together functional services for the rest of my career. Probably a lot of Microsoft tech would be involved, and this work is stigmatized as “boring” a bit too often, but ASP.NET and related tools are pretty solid these days and you can add enormous value to organizations in many industries just by integrating this kind of infrastructure with their existing processes. Second, I like the idea of branching out and finding new projects, but why abandon the computer side of it? This century will continue to see amazing new ways of doing business that were never possible before. Commodification of computing continues and shows no sign of stopping in my lifetime. Why not learn a new domain and then bring what you already know about technology together with that knowledge? That is as close to a guaranteed recipe for success as anything I’ve ever heard of.