Forget Habit Hacks. Here's What Real Change Actually Requires.

On Change, Getting Stuck & What Actually Moves You Forward

There's a creek in my woods that used to be a road. In the twelve years I've been walking these trails, I've watched it transform completely — the topography reshaped, the path erased, the water claiming what was once solid ground. But here's what I keep thinking about: the change isn't finished. Some days the creek is dry. Some days it's rushing. It's in constant motion, even when the big transformation is long done.

That creek has become a physical manifestation of everything I've been reading and thinking about lately. About change — what it actually is, how it works, why it's so much harder than we expect, and why that difficulty doesn't mean we're doing it wrong.

There's no single path through

The most research-grounded book I've found on this subject is Katy Milkman's How to Change: The Science of Getting from Where You Are to Where You Want to Be. Milkman is a behavioral scientist at Wharton, and what I love about her approach is that she doesn't just tell you to build better habits and send you on your way.

It's more like a compendium — a whole menu of evidence-based strategies depending on what kind of change you're trying to make and what's getting in the way. Fresh starts. Temptation bundling. Social commitment devices. The specific obstacle matters, and the approach should match it.

This mirrors what I see in my coaching work every day. There's no one-size-fits-all path — for lawyers or anyone else. The self-awareness piece — knowing your particular flavor of stuck — is what makes any strategy actually work. Without it, you're just picking tactics at random and hoping one lands.

Why knowing isn't enough

Let's start with time entry. The data is unambiguous: lawyers who enter their time daily capture significantly more of it. Everyone knows this. Most firms remind their attorneys regularly — often via increasingly exasperated emails from Accounting. And yet.

Why doesn't knowing the right path mean walking it?

Chip and Dan Heath's Switch: How to Change Things When Change Is Hard offers a metaphor I keep coming back to. Imagine a Rider on an Elephant. The Rider is your rational mind — analytical, strategic, always planning three steps ahead. The Elephant is your emotional self — your habits, your fears, your energy levels, your gut.

The Rider holds the reins. But the Elephant has all the power.

Most high-achievers are extraordinarily well-developed Riders. Which is exactly why change can feel so baffling.

You've done the analysis. You've heard the argument. You know what to do. And yet — nothing moves. That's not a willpower failure. That's a Rider trying to drag an Elephant.

Lasting change, the Heaths argue, requires working with your Elephant: making the right behaviors easier, finding the feeling that actually motivates action, and starting small enough that the challenge doesn't feel overwhelming before you begin.

There's a related concept from Dr. Ronald Heifetz at Harvard's Kennedy School that I find equally clarifying. He distinguishes between technical problems — those with known solutions implemented with existing expertise — and adaptive challenges, which require something harder: changing beliefs, behaviors, or underlying assumptions.

Lawyers are trained to be masterful at the former. The latter? That's where the Elephant lives.

Being stuck is not a personal failing

Here's the reassuring — and slightly uncomfortable — thing: getting stuck is not a sign that something is wrong with you. It's a predictable feature of any meaningful pursuit.

Adam Alter makes this case compellingly in Anatomy of a Breakthrough: How to Get Unstuck When It Matters Most. The researchers, artists, athletes, and executives he studied all hit walls. The question isn't whether you'll get stuck. It's whether you recognize it for what it is — and know how to move through it.

What I learned is that stuck-ness often signals that your current approach has run its course — not that you have. (The creek didn't fail. It transformed.) Breakthroughs rarely come from pushing harder. They come from changing the conditions — a new environment, a different collaborator, a question you haven't thought to ask yet.

And sometimes the most important thing you can do is just… keep moving. Literally. Which might explain why so many of my best ideas arrive on dog walks.

What's actually keeping you stuck

Most change efforts fail not because people lack information, but because they're trying to solve an adaptive problem with a technical solution. They read the book, attend the seminar, download the productivity app — and then wonder why nothing shifts.

The gap isn't knowledge. It's the values, beliefs, and emotional patterns operating underneath — the ones that don't respond to logic, no matter how compelling the argument.

And here's what Milkman, the Heaths, and Alter all agree on, even if they arrive there differently: the approach has to match the obstacle. There's no universal fix. What works is the strategy that fits your particular version of stuck — which means the first step is always the same. Figure out what's actually in the way.

I've been watching this play out in real time with clients. Super smart, motivated people who know exactly what they want and still find themselves circling back to the same place. Not because they're not trying. Because they're trying in the wrong direction.

The creek in my woods is still changing. Some days there's barely a trickle. Some days my feet get wet trying to traverse it. The big transformation — road to creek — is done. But the smaller ones are infinite.