Last week I was excited to record a Design Shift podcast interview with my good friend and former colleague…a person my wife calls my “pawtnah,” Eric Fain. Eric works at the intersection of design, product strategy, and systems thinking. We spent years working closely together at Autodesk, where he led design on some of the company’s most important platform and collaboration efforts, helped shape its first generative AI strategy, and built alignment across teams at massive scale. Over a 20+ year career, he’s consistently taken products from zero to one while navigating the complexity of enterprise environments.

This conversation (and my write-up below) is about what happens when you take that depth of experience and apply it on your own terms…where design becomes less about artifacts and more about judgment, leverage, and the confidence to build.

Read on for my main takeaways from our conversation. 🎧 And…listen to the recording of our full conversation on the Design Shift podcast on Spotify and Apple and the Design Shift YouTube channel.

— Justin Lokitz

Though my podcast interview with Eric was compressed into just an hour, much of the same conversation has unfolded over the hours and miles we have spent hiking together in both the Bay Area and parts of the John Muir Trail.

From all of those conversations, what I think is more interesting (and even comforting) is that Eric’s slow hunch, after leaving Autodesk, was NOT to pursue a single big idea. He left to run experiments.

Today, Eric is building a portfolio of products, like Bikehealth, Sideline HQ, and others in progress, not because he’s unsure or even wishy washy, but because he understands that the fastest way to find traction is to put things into the market and learn. There’s a discipline to not getting too attached to any one idea, especially when the cost of building has dropped so dramatically.

At the same time, the problems he’s drawn to have shifted…certainly since we worked together many moons ago. Earlier in his career, like many of us, there was an appeal to big, category-defining ideas…the “Google for X” mindset. Now, he’s much more interested in what he calls “blue-collar problems.” These are real, grounded problems/opportunities with clear demand and a defined set of users (which echoes what I often hear from entrepreneurs interviewed for Starter Story, a YouTube channel I follow). They’re not always flashy, but they’re often where the most meaningful opportunities exist.

For Eric, the move from design leader inside large organizations to independent builder was a gradual realization (read: slow hunch) that the constraints he had internalized no longer applied. That moment came while building Bikehealth, when he moved beyond designing interfaces and started integrating with external systems like Strava, a popular social fitness-tracking app.

And…as I’ve written and interviewed people about before, in this new AI-builder paradigm that we’re living in, Eric-the-designer has become Eric-the-builder, wherein, via a direct connection with Strava (via an API) and vibe coding platform, like Cursor, he could actually build and connect the entire system. That’s when something shifted. The dependency on others to execute started to disappear.

This is where his perspective on design becomes especially relevant. From Eric’s point of view, design is more about framing than craft. The ability to stage a problem in a way that surfaces hidden assumptions, clarifies disagreements, and sets up the right path forward. In his words, most problems aren’t actually that complicated once they’re framed correctly. The complexity often comes from misalignment, not from the problem itself.

That way of thinking shows up in how he builds now. The tools have changed, but the underlying approach hasn’t. Instead of coordinating across teams, he’s working directly with AI agents; each one is focused on different domains like design, branding, or go-to-market. He routes questions, compares perspectives, and makes decisions. In many cases, he gets what he needs quickly. But…the real work is in knowing which direction to take and when to change course.

That’s where judgment and taste come in. As execution becomes easier, the value shifts upstream. It’s less about whether something can be built and more about whether it should be built, how it should work, and how decisions will play out over time. Eric talked about this as the ability to hear multiple responses and choose a direction, or to recognize when a workflow needs to be rethought entirely. It’s also about understanding that AI will often validate whatever direction you’re leaning toward, which makes independent thinking even more critical.

At one point, he described what it feels like to build today as “feeling like a god.” It’s a striking phrase, but it captures something real. The barrier between idea and execution has collapsed to a degree that would have been hard to imagine even a few years ago. That doesn’t mean the work is any easier! In fact, in many ways, the work of design must be even more focused than it was a few years ago. And…at the same time, it does change what’s possible for an individual builder.

So why don’t more designers (both with a capital D and a lowercase d) take advantage of that?

Eric pointed to two things: the first is financial risk, which is real and requires planning. The second is fear…specifically the fear that nothing will work. That fear shows up as hesitation, as waiting for the right idea or the right moment. His advice cuts through that pretty quickly.

Build something, anything…right now! Start small if you need to, but get it out into the world. The act of building is what changes your perception of what you’re capable of.

Interestingly (at least to me), I received the SAME advice 13 years ago, during a guest lecture in grad school! The guest lecturer was Chris Waugh, who at the time was Ideo’s practice lead for Health and Wellness. And…while vibecoding tools were still a decade away, his advice to all of us designers was to build something and launch it on Kickstarter, just to see how it all works (in the real world).

A year ago, Eric saw himself primarily as someone who led teams that built. Today, he’s in the code, working across technologies he hadn’t touched before. That shift isn’t just about new tools, like Cursor, Bolt, Gemini, or Lovable! It’s clearly about a different belief in what he can do. As he put it, the biggest change is that he now believes he can do anything he sets out to do.

That’s the real takeaway from this conversation. Not that everyone should go solo, or that AI changes everything overnight, but that the gap between what you think you can do and what you can actually do is smaller than it’s ever been.

Want more? Connect with Eric and tell him Justin sent you! You can check out some of Eric’s work here.

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