3 Questions Living Rent-Free Inside My Head

Greg Robleto
2 min readApr 12, 2023


These are three topics that I can’t stop coming back to again and again and much of my reading, listening, and ruminating falls back into these questions.

#1: What will happen next with AI?

In 2007, I was at SXSW when Twitter was unveiled and adopted it early to share essential musings like getting BBQ for lunch. Those were the honeymoon days before it was weaponized.

In 2023, I think we are in the early “I’ll be at Iron Works after this panel” days of this new technology. We’re still basking in the novelty and quirkiness of getting straight answers from an AI, but it’s a honeymoon, and I am fascinatingly curious about what comes next.

#2: Are we giving up on User Experience Design?

I took the family to Disney World this past week and had to Google, YouTube, and ChatGPT to learn how to maneuver the confounding Genie Plus / Fast Pass process.

One more example of a massive shift I’ve been seeing away from valuing design and an intuitive user experience. Evolution isn’t smooth, and I’m hopeful UX will return when progress plateaus, but until then, I see a race toward function at the cost of form.

#3: Where are all the tech jobs?

I know multiple talented Design and Developer colleagues who have been out of work for a year. The Wall St. endorsed tech layoffs are flooding the supply side of the market, and in a remote working world, you are competing for jobs with everyone everywhere all at once.

Had I the option to take a 12-month severance package, I’d decline; it’s ludicrous to say, but I don’t see that as enough runway. For the first time in my professional life, I would be unnerved to be a tech professional out of work.

I don’t have any answers, do you? What do you think?



Greg Robleto

Creative leader at the intersection of design, product, and tech. Writing mostly about design, CSS, product strategy, leadership, investing, and more.