Burn the Boats summary

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.