Roadmapping is one of the most underrated factors in highly regulated industry product success.

The greatest product idea, the most eye-catching marketing plan, and the most well-coded, secure, compliant product will fail if it lacks a thoughtful roadmap.

A roadmap isn’t just a list of features—it’s your strategy for surviving the constraints and still delivering something users care about. For founders, the question isn’t just what to build—it’s what to build first, and what to leave out for now.

There’s a trap visionary founders fall into all the time: assuming users are buying the same thing you’re building.

They’re not buying secure email. They’re not buying multitouch screens. They’re buying a story about themselves. They’re buying a feeling.

In this installment, we’re looking at one of the clearest case studies in tech history: Apple vs. BlackBerry. Both had vision. One built a product. The other built an identity.

What captivates visionaries about the latest crop of AI tools is the promise of combining the best of technology (speed, accuracy and consistency) with the best of human ingenuity (compassion, creativity and nuance). That’s what users want and hope for from AI. It’s supposed to be like a computer, but softer. Like a human, but more knowledgeable. The very best we, collectively, have to offer.

Of course, as with any tech revolution, the path to achieve this is not trouble-free.

You’ve poured heart, soul, and probably a few too many late-night snacks into your next big release. But launch it the wrong way, and brace yourself for the Two Weeks of Ire — that stretch of time when users react like you’ve rearranged their kitchen drawers during a dinner party. There’s fascinating psychology behind this resistance to change (especially when it’s forced), and a near-magical technique that can flip the script. In high-stakes industries like finance, healthcare, and insurance, it can mean the difference between angry support tickets and genuine adoption.

Bonus: A Venn diagram, Sade, and why your neighbor won’t stop talking about his new truck.

If you’re like many people, you may think of UX (and by proxy, emotionally connected design, which is a big chunk of what we mean when we talk about UX) as the domain of ‘fluffy’ products like social media apps, games and self-improvement products. If you’re in a highly regulated industry like insurance, finance or healthcare, you may have assumed this wasn’t your sandbox in which to play.

To that I say, sit right down and grab a bucket shaped like a tower. We’ve got a castle to build.

There comes a time in every visionary’s life when the ever-present gentle push in the back of the mind to make it bigger and better becomes instead an oily whisper of “You haven’t done enough.”

There was an awkward pause. Our visionary, the client organization’s CEO, was uncomfortable. I could tell by the way she drew up her shoulders and tried to steer the conversation in a different direction as quickly as possible.

The truth is, to make an impact through tech, you simultaneously have to care a whole lot and not at all about the audience. You have to care deeply about their problems but not at all about their praise.

Somewhere right now, someone is holding up a solved math problem, a 3D-printed baby Yoda, or a plate of perfectly cooked gnocchi and saying, “Look!”

That’s the magic moment: progress. Humans are wired to make things better. We tinker, we refine, we toil—and sometimes we even smile through the struggle—because we’re chasing that spark of wonder.

Yesterday I wore my Bob Ross shirt. It says “No mistakes, just happy accidents.” While not a mentality I’d advocate for the implementation phase of a project, it captures a philosophy I like for the early stages of design, because it makes space for innovation to take root.