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.

Design patterns have limits. When you need to go to the moon, even the greatest paper airplane will not do.

We have a fake ID and we’re 18! There was a mix-up at the Secretary of State’s office, and it shows our business creation filing as April of 2006 but I am sure it was 2007. So, as we see it, we get to pass for 18 as long as the bouncer doesn’t ask us any tricky questions about our height or birthday (wink).

That’s pretty cool, because at 18, a young person in this country gets to do some exciting things: namely, vote. When I turned 18 (for real), it was also the legal age to use tobacco, so I bought a cigar, attempted to smoke it and promptly vomited in a trash can. Voting would have been more dignified, but there wasn’t an election handy and I wasn’t a patient girl.

Of course, what makes voting dignified is knowing what you stand for. That’s one reason we don’t get to do it until we come of age - we need time to understand the world and what matters to us.

Here are 5 things ET would vote for if it could:

There’s a finely tuned tension between the drive to get things done (of which entrepreneurs often have an amplified dose) and the patience required to not make an absolute mess of things.

Last week, I wrote about unsolvable problems almost always being due to missing information.

In practice, this also stems from a general intolerance of that period of uneasy toiling when we’ve identified that there is a problem to be solved, but haven’t yet solved it.

I’ve been chewing on the same infuriating question since before the holidays. I knew I needed to solve it, and yet it resisted all attempts, and I churned.

I tried to think this question out. It would not be thunk into submission.

I tried to diagram it. It sneered in the face of my circles and arrows.

Thus affronted, I pulled out the big guns: I threw math at it.

We live hundreds of corporate lifetimes through our clients, and of course those are piled on top of the undercurrent of our own cycles.

Because of the velocity with which we as advisors experience these ups and downs, we get to see it with a little perspective. We know that although we do this every day, for our clients, it’s a rarer event, so we have the luxury of a little longer view on these things – namely, that sometimes it all feels big and heavy and people don’t always talk about that enough amid all of the highlight reels.

A lot of what I write is strategy on how to have a bigger impact, keep your investment working for you longer, and generally do tech experiences better.

Today’s not going to be about that, because I’m getting to the age where I want it all to mean something.

If I’m going to spend a good share of my waking hours investing gobs and gobs of energy into something, I need to feel that it has a purpose in itself. And I’ve concluded that it does, but not in the way that my 25 year-old self expected.

This is the story of how a small software team (us) crafted a ticketing system for a savvy client that drives faster agent response times than Zendesk and kept that advantage for 10 years with minimal updates.

When I was a kid, I fell in love with a PC game called Heaven and Earth. The graphics were gorgeous. It was peaceful (a nice alternative to Wolfenstein 3D which was too scary for me) but had enough tension and variety to keep me engaged. A couple of years back, swept away by nostalgia, I went on a mission to find and play this game again. In the thirty years since, I have never found a game that made me feel the same way.

In the early 1990s, Windows released a surprise standout program. Users flocked to it, spending more time on it than the much-vaunted Word or Excel. This program was developed by a bored intern named Wes Cherry on a lark and included by Windows ostensibly only to train users on how to operate this newfangled thing called a mouse. This program yielded no visible benefits to the user; it did not produce spreadsheets or documents. It did not allow the user to read email or the news. But it had one thing that trumped all of these shortcomings in attracting and keeping users: an absolutely killer cascading card animation at the end.

It is surprising how often motivation is forgotten in the drive for change. We assume that merely by supplying the means, people will bend their behavior to our designs. “If you build it, they will act.” But they generally will not, unless supplied with motivation that bests their existing motivation, and therein lies the rub.

In this article we explore how we use feedback to drive behavior, and provide some general guidelines anyone can use to be more successful at motivating change.