Brief summary

'Burn the Boats' by Matt Higgins is a memoir that recounts the author's journey from a difficult childhood to becoming a successful entrepreneur and investor. It offers insights into the importance of taking calculated risks and persevering through adversity.

Table of Contents

What’s in it for me? Here’s motivation to go all-in on your dreams.

When Julius Caesar arrived on the English coast with his army, ready to conquer the island, he quickly realized that he was outnumbered. So he did something that would seem absolutely reckless to most observers: he ordered his men to burn their own boats.

Worried that his soldiers would be tempted to retreat, Caesar didn’t want to give his men any reason to hold back in battle. Burning the boats meant there was no way home. No alternative. No Plan B.

At 14, Matt Higgins didn’t know about Caesar's strategy. Yet even at such a young age, he intuited the wisdom of burning your boats. Today, Matt is a successful venture capitalist. But back then, he was desperately searching to escape the grinding poverty that he and his mother were trapped in: a tiny, rent-stabilized apartment in Queen’s, New York, with an almost-empty fridge.

He knew that his low-wage McDonald’s job wouldn’t cut it. And it would take years before he would start college and get paid college student rates. If he wanted to escape this dire situation quickly, he would have to take a leap.

Matt realized that he could drop out of high school at 16, take the GED, and then apply to college two years faster. That meant two years closer to earning college wages and two years closer to putting food in his mother’s fridge.

Matt didn’t tell a soul about his plan. He knew that his teachers would try to pull him back on course if he were merely scraping by. They had to believe he was hopeless. In other words, he had to burn his boats. So Matt stopped going to school. He failed every class spectacularly, and the day he turned 16, he dropped out.

Why is burning your boats so effective? And how can you find the courage to take similar bold action in your own life?

That’s what you’ll discover in these blinks. With the wisdom of Matt Higgins to guide you, along with inspirational stories from people who’ve built wild success and achieved their dreams, you’ll learn how Plan B sabotages your true calling. So grab your matches – and let’s get burning.

Trust yourself to take the leap.

Matt immediately recognized the genius in 26-year-old Jesse Derris. Already making partner at the publicity firm where he worked, Jesse had no trouble offering unapologetic truths to CEOs twice his age. His ability to see patterns and predict trends was practically a sixth sense.

But Matt could also see that Jesse’s talents were being squandered. So the two went for a walk one day, and as they looped around Manhattan’s Madison Square Park, Matt offered to invest $2 million in Jesse to start his own PR company.

Despite Matt’s confidence in him, Jesse was petrified to strike out on his own. Was this a good time? Was he capable? Still, his gut was telling him this was the right move, and after an encouraging conversation with his girlfriend, he took Matt’s offer.

Jesse’s story demonstrates the first key to burning your boats: Taking the leap requires trusting your instincts, even when it goes against convention.

That doesn’t mean it’s easy. When you’re about to jump into the unknown, your mind will pull out all the stops. The signs will suddenly try to point you to safer ground. Here are just a few things to remember if conventional ideas are keeping you from taking the leap.

The first is that there will never be a perfect time to act, and, in fact, it will probably only get harder later. If something is calling to you, do it now.

Second, don’t wait for validation or buy-in from others. Taking calculated risks is all about seeing opportunities where others don’t.

Third, don’t think that you have to stay in your lane. Society will tell you to stick with what you know. But consider Sarah Cooper, who had a 15-year career in tech. When her satirical blog about Silicon Valley blew up, she took the leap into comedy, leaving her cushy Google job behind. And in 2020, she landed her very own Netflix show.

Last, don’t buy into the convention of incrementalism. People will convince you to put in your time on each rung of the ladder. But some goals require a leap – or a whole different ladder. Incremental growth is just a Plan B in disguise, so don’t let it hold you back.

In short, when your instincts conflict with what the world is telling you, do not hesitate or doubt yourself. What is your vision for your life? Do you really want to miss the chance to be the most extraordinary version of yourself?

Just ask Jesse Derris. In 2022, a few short years after starting his own firm, he sold it to PR giant BerlinRosen, and is now a self-made millionaire.

When the going gets tough, chase the fear.

The journey to a rewarding life isn’t always smooth. After you take the leap and burn your boats, it’s common for fear and anxiety to set in. Crises are inevitable when you take big risks and go all-in. So it’s best to buckle up and prepare for the bumps ahead.

When the going gets tough, the temptation will be to slam on the brakes and make a U-turn. But what you should do instead is drive into the discomfort.

Consolidate your gains and burn the boats again.

Burning the boats is about owning your journey, whatever it may be. You don’t have to chase other people’s ideas of success. It all starts with a vision for your life. Maybe you want to work on your own terms. Maybe you want more financial security, or to serve an important cause.

Whatever the vision, no matter how fantastical it sounds, listen to it. When your psyche is trying to tell you something, take it seriously.