This as-told-to essay is based on a conversation with Dean Grey, a participant in a program by AI Commons that aims to upskill and retrain workers who have been displaced by AI alongside a monthly stipend. Grey is an entry-level software engineer who is struggling with his job search.
I never imagined I would become an early participant in what feels like a social experiment for the AI era. But after spending years trying to break into tech, only to watch entry-level jobs evaporate almost as quickly as I got there, that’s exactly where I found myself.
I grew up in Massachusetts and graduated from UMass years ago. Before tech, I worked mostly in management jobs, “just sort of trucking along,” as I like to joke — though eventually that became literal. I spent about 4 years working in trucking, but I knew I wanted something more stable and better paying, and tech seemed like the future. Shows like “Mr. Robot” and movies like “Hackers” made the industry feel exciting and creative.
So I saved up enough money to make the leap. I enrolled in Hack Reactor, a coding boot camp program, where I learned software engineering. At the time, I thought I was doing everything right.
I trained for a tech career as the market collapsed
After boot camp, I joined a training-to-hire company that promised to prepare people like me for jobs with large clients. The understanding was that we’d move directly into industry work afterward.
By the time my training ended, the market had changed dramatically. Hiring had slowed. Companies were suddenly obsessed with AI. Instead of moving directly into work, many of us were put on waiting lists for months. I waited about five months before eventually landing a contract position with Infosys.
It quickly became clear there wasn’t much future there. Our contracts were finite, and there was really no upward mobility. I had put all of my eggs in this basket, and it was disappointing.
When that contract ended, I entered what became one of the hardest periods of my life.
Hundreds of applications met with silence
Like many people trying to break into tech right now, I sent out hundreds of applications.
I got a handful of phone screenings and two Zoom interviews that never progressed beyond the first round. At one point, it was exciting to get a rejection because a lot of companies were just ghosting me.
I burned through savings, called in favors, took gig work and temporary jobs, filled out online surveys — basically anything I could do to survive. Unemployment benefits helped for a while, but not enough to build a future.
The UBI program gave me structure and hope
When the AI Commons approached me about joining a new basic income pilot program for workers displaced by AI, I was mostly grateful not to feel alone anymore.
The program provides a monthly stipend — up to $1,000 — along with technical training, mentorship, engineering projects, and community support.
The project is still so new, and the curriculum is still developing, but it gave me a sense of hope and structure again, which matters more than people realize.
Every morning starts with standups where we discuss what we’re building and what’s blocking us. I meet weekly with mentors and pair-program with more experienced engineers. For the first time in a long time, I feel like I’m moving forward instead of standing still.
The financial support has also been such a boon and life-changing. Being behind on all my bills has been a crushing stress. But with this basic income, I’m able to focus on improving my résumé, working on projects, attending meetings, and building my network.
The stipend doesn’t feel like permission to stop working. If anything, it’s the opposite. It gives me enough stability to actually invest in myself again.
Now I’m building an AI chatbot to help laid-off workers
One of the biggest projects I’m working on now is an AI-powered chatbot for people navigating layoffs and unemployment.
The idea is simple: when someone loses a job, they often don’t even know what questions to ask first. My chatbot is designed to guide them through the process, explain unemployment laws by state, connect them to resources, and eventually help direct them toward real human support systems.
I don’t know exactly what the future of work looks like. Honestly, sometimes it feels bleak. But this program has convinced me that people can adapt if they’re given enough support, time, and community to do it.
I hear a lot of criticism of UBI, mostly about how it could erode agency and meaning and might be taken advantage of.
I’m optimistic because, at the end of the day, it might just mean we transition to a new way of finding purpose, if not in what we do for a living, then in how we express ourselves or what we do creatively. I don’t think that we’ll ever run out of ways to find purpose in life.
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