> I feel like between AI and offshoring I might just need to do something else all-together.
Let me address this one upfront, both for you and for the other job seekers out there fretting over the same thing. AI won't replace a competent Engineer anytime soon, and offshoring/outsourcing is a continuous part of any business cycle. While tech companies are very much in the early days of outsourcing and offshoring, non-technical companies are actually at the opposite end - looking to bring talent back in house after years of outsourcing with decreasing satisfaction or results.
It's just a part of the cycle, really, if you're looking to transition into "stable" work. Companies will always be chasing fads that claim to make everything better while also lowering costs, be it AI, some hot new tech hub in a cheaper economy, leveraging MSPs, or just flatly trimming headcount and "increasing velocity". You're gonna have to learn to roll with those rhythms and punches if you want to thrive.
> I feel like a freaking loser given my age and my relative career stagnation / my inability to actually turn my mildly above average skills into any real money.
Imposter syndrome sucks. From my perspective as one of these technical "normies", I'd consider you more successful by simple fact you actually sold a company - not an easy feat! Think of it as just switching to a different "lane", with different expectations; you're not a failure, you're just growing in a different way with different challenges than you're used to.
With all that being said, and without really understanding your specific skills/fields, here's some generalized advice about the "normal" tech world:
First, figure out where you want to work in terms of "vertical", as tech is often divided into "enterprise" or "business" technology (as in, the folks supporting how business gets done), and "product" technology (the folks making and supporting the way the business makes money). Some companies may try to combine the two, but they're often like oil and water in that they don't mix well.
* BizTech is often a slower pace because you generally want people to do work, not figure out how to do work, and so there's a stronger emphasis on stability, reliability, and repeatability.
* Product tech is more fast-paced and focused on solving new problems, building new things, and delivering on roadmaps. This sounds like it might be more directly transferable skills-wise since you're coming from Startup World, but that market is a hot mess right now thanks to Big Tech layoffs and AI hype.
Next, identify where your existing skills fit within that vertical, and rewrite your resume to highlight those capabilities.
* Focus on the specific technical achievements with all the buzzwords you used along the way. Don't pitch stuff like "delivered an app with 10k concurrent users and five-nines uptime on a budget of $X", because most companies don't care about your company. They want relatable achievements, like "Built ArgoCD Pipeline to orchestrate production Kubernetes clusters using GitHub Actions."
* For developers, focus on languages known and share your GitHub. For Infrastructure/Network/Storage/Systems folks, focus on vendor suites and how you stitched products together with automations.
* Two big topics in companies right now are cost discipline and flexibility in hires. Play up both, since you have them from your startup days. Highlight cross-domain shoestring budget deliverables in particular, companies will eat that up as it shows you're both multi-disciplined and cost-conscious.
* Consider some certifications to shore up your bone fides, especially if you're going into BizTech/IT. Those almost always get preferential treatment by employers, at least for interviews.
When you get interviewed, make sure you're asking questions about the company's operations (within reason). This shows you're aware of the requirements of the business world. Stuff like:
* Is there an on-call rotation?
* What's the organization's roadmap over the next two years?
* What challenges are they having? (Which you can hopefully then explain how your skills help them address that challenge)
* For multi-national firms, how do they support their global workforce or customer base? Is it a follow-the-sun model, shift rotations, or something else?
The most important thing to remember is that you're no longer selling a company, you're effectively selling yourself. You need to identify what problems they're facing, and then position yourself as the product to address their ills.
One more thing: leverage your existing network to find some good recruiters, as they can help you get your foot in the door and your resume at the top of the pile. Some recruiters focus on specific industries, while others focus on specific roles.
You can do this! The "normie" technology job market is still forecast for substantial growth globally and domestically over the next decade, especially in Engineering and Architecture. Keep at it, and you'll find your way in due time.