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Yeah, it's really difficult because a lot of the drive expressed in OP is for a new source of opportunity... The problem is that ageisms and such definitely take root in our industry, trying to work healthy hours at a startuppy place when you are older seems very precarious. I think you are on point that technical management has more availability, if that's the constraint.

If the constraint is instead that programming looks fun but you want to get exposed to as much of it as possible, I mean, I would suggest that OP’s Dad start building an indie game or so? Doesn't have to be a bestseller to sharpen thinking about design and aesthetic and underlying mechanics and state and data structures... I work in web but the amount of framework churn and such is kind of something I wouldn't force others through.

If you did want something more webby, you would want to practice with something you find interesting... If you wanted, maybe something that touches a lot of other technologies. If you think about writing your own GitHub, you start with git repositories and cloud hosting and deployment, you can move into CI/CD type workflows pretty easily, maybe that is a better way to start off web programming?

The other thing I will say is, Big Tech companies are often places where you can get one role and then ask for their developer education tracks where they teach their accountants etc how to become developers if they want to pivot. Say for example, being a manager at Google but having some 20% project that lets you contribute code and get feedback. Bigger more established companies have fewer problems with ageism, because they are much more sensitive as lawsuit targets for those sorts of things, so they have to get their s** together.

Also worth saying, the prior job history is an asset. A lot of developers do not speak business-ese. If you are a solid programmer who can talk to C-levels, you are a potential CTO at the right sort of place. Because you can translate, and because you feel comfortable walking into a contract negotiation with some client as “okay, how can I not say ‘no’ to everything but push back on the really hard problems while ‘yes, and’-ing all of the tractable stuff to get them on board.” Consultancy is one of the ways to do that, but not the only one. But worth calling out that as an asset if it helps focus the journey more.




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