Well, “should you”? Only you can decide that. You only get the one life, you know. It would suck to spend it only doing things because they’re “prudent”.

It seems like you’re asking for market predictions here, based on the AI and outsourcing aspects. Nobody knows what the future holds. But we can look at the past and present.

Historically, companies — both individually, and the industry as a whole — tend to oscillate between:

• “oh my god, knowledgeable people are so expensive, I don’t need someone with deep understanding, I just need more output” and
• ”oh fuck, I am drowning in output that nobody understands, I desperately need knowledgeable people”

For all the AI corpos’ talk about a revolutionary change in the way we think about work and employment, it all looks very familiar right now.

Historically, these moments, where everyone seems to agree that they want more hands on keyboards rather than more brains on call… tend to be the worst time to freelance.

It’s a race to the bottom, and you’ll probably be so busy spinning plates that you won’t be able to make any long-term strategic decisions about what you wanna learn and do next.

If you can, I’d look for a stable corpo job that you can firewall to 9-5, and keep your options open. Watch the market, and — more importantly — find something that you like, so you don’t have to ask internet strangers what to do with your life again.