Kim Wensel

Episode #056

Book Talk: Do You Really Have To Burn The Boats?

Do you really have to burn the boats to make a meaningful change?

Matt Higgins’ book, Burn the Boats, argues that keeping a Plan B can get in the way of fully committing to what we want. I expected to disagree with a lot of it. I did—and I was surprised by how much I agreed with, too.

For the first Book Talk episode of 10,000 Tabs, I’m digging into self-trust, instinct, risk, boredom, blank space, and knowing when it’s time to stay with an idea long enough to see what happens.

Why I Almost Didn't Finish This Book

This is the first Book Talk episode, spelled out, "not to be confused with BookTok TikTok." I've read a lot of nonfiction over the years, mostly business strategy and personal development, and I've since added far more fiction, which I recommend to anyone whose brain never fully switches off.

For the first title, a book about pivoting or reinventing yourself would have sat too close to my own book coming out. So I picked up Matt Higgins' "Burn the Boats," which I'd abandoned around page 60 a while back, and read the whole thing with a blank slate.

I went in hesitant. Books "written from a middle-aged white man in venture capital" who is telling you how to become successful tend to arrive with a predisposition — politically, socially, business-wise — and this one does.

Success here is largely defined by acquisition, or a $100 million company. He introduces a business partner by way of an $11.6 billion net worth. At one point he asks why you'd bother with a project that wouldn't force you to update your biography.

Finding the Line That Changed How I Read the Book

The opening pages go where you'd expect: To accomplish something great, you have to leave yourself no escape route. The act of building a safety net is precisely what forces you to need one. Hesitation kills more dreams than speed ever will.

Then, somewhere around page 17 or 32, unbolded and unmarked, he writes that the entire book is about not becoming hesitant when your instincts don't match what the world is telling you to do. I snapped up when I read it. We stop ourselves because we already know the thing won't make sense to anyone else.

"So what Matt is actually talking about is self-trust," I say on the episode — a considerably harder sell than tossing your Plan B and sealing every exit.

Which raises the question of where instincts come from. There's no course for it. Personal development and therapy are about the only places I know of where you learn to hear your own voice clearly. "We're not learning that in school. We're certainly not learning that in business school."

And if you're first into a market, there's no data proving any of it will work. "When you rely solely on data, there's so much opportunity to second-guess yourself."

Watching Someone Else Act on Your Idea

Choosing a non-traditional path means there are very few people ahead of you doing the thing you've imagined. I've cobbled together a handful of examples of the life I want from people who each have one piece of it. That's disorienting, and it's part of why I've gassed out on my own writing before — I knew the choices wouldn't make sense to anyone watching. "No matter how self-assured you are, and no matter how much support you have, we all want to be understood, and we crave belonging."

Then comes the other version of it: you see somebody else do the thing you had in your head, and you think, why them? They're not even that good. I could have done it better. The only difference is that they decided to do it before anyone confirmed it would work.

But my own pattern is the harder one to break. "When I know that there's room for improvement, I hold back instead of saying this has to see people in order to keep getting better."

What It Costs to Move Before You Have Proof

I'm doing this work myself right now, in relationships and in professional decisions, in conversations I'd rather not have. The practice is making the decision as soon as it enters my awareness. "It's fine, I can handle it, it'll get better, I'll just wait a little longer." And how often does it?

Higgins names the mechanism that keeps us in place. Most of us feel worse losing $100 than we feel buoyed by gaining $100. Applied to changing direction, that becomes the years already invested, the degree, the loan still outstanding, the salary that arrives every two weeks. He asks whether you're looking behind you or ahead of you, because you can't look both ways.

There's also the story of him catching COVID early on, isolating for a month, and writing this book instead of resting, because he'd regret the idle time. I read a lot of the book as written from a fear of getting behind. I spent about 30 years motivated that way myself.

Discomfort is worth something. Hard as the baseline of a good decision is not. "I've seen too many people make changes based on what they don't want instead of getting clear on what they do want."

Where I Am in the Messy Middle

I gave the book an 8.5. The positioning I understand — edgy, attention-grabbing, a very specific point of view — and underneath it Higgins gets somewhere real about trusting yourself over public opinion on your own life.

Which is exactly where I'm standing. The Multi-Hyphenate Dilemma is available for preorder now and arrives October 13, 2026. Writing it is finished. Marketing it, making meaning of it, pitching myself for podcasts and stages — that part is in front of me, and it has been scary some days and boring others. What I keep telling myself: "People aren't going to understand it on the first time."

Consistency, as I understand it, is staying with something past the boredom and past the conviction that nobody wants it. Under a year, under two, people simply haven't caught up yet. There's a retraining period, whether you're building a business or introducing yourself in a new way.

I'm also holding the opposite instruction — blank space every week, outside of vacations and holidays, because I can't hear my own voice in hustle mode.

We can "exhaust ourselves building the thing and gassing out before the thing even reaches the world," and this is the milestone I don't want to gas out before.