Nathan Tanner

You Don’t Have to Burn the Boats. Do This Instead.

In 1519, the Spanish commander Hernán Cortés arrived in the new world with grand ambitions of conquering Mexico. The story is told that before entering battle he gave instructions to destroy the ships his men had used to sail to the Americas. This audacious act sent a clear message: There is no turning back. We will conquer or we will die.


This story of Cortés burning his ships has become the stuff of legend. I still remember the first time I heard it. I was in awe at Cortés’ boldness and left with the lesson that if I was to find true success, I need to go all-in and burn the proverbial boats. 

Of course, there’s something to be said of a grand act that signals to both you and others that you mean business. Burning the proverbial boats is inspiring. It’s radical. It’s courageous. But for most, it’s unwise and it’s unnecessary. 

Take Richard Branson, an entrepreneur widely viewed as someone willing to bet the entire farm to win. In the early 80s, Branson was anxious to meet his romantic interest in the Virgin Islands but his flight got canceled. He then marched to the back of the airport, handed over his credit card, and hired a plane.

Borrowing a blackboard, he wrote “Virgin Airlines one-way: $39 to the Virgin Islands” and filled up the flight with all the bumped passengers. The next day he called Boeing, shared that he’s thinking of starting an airline called Virgin and asked if there were secondhand 747s for sale. He struck a deal with Boeing and founded what came to be known as Virgin Atlantic. 

Branson’s actions were bold and audacious. We may think, “Now that’s a man willing to burn the ships and really swing for the fences!” But as it turns out, there’s more to the story. 

Branson was already the successful CEO of Virgin Records and had a lot to lose by entering the capital-intensive airline industry. In an interview with Tim Ferriss, Branson shared that the leadership team at the record company thought his idea to start an airline was crazy. They were worried he’d risk everything. 

“Look,” Branson told them, “I promise that I’ll only go into the airline business on one condition and that is if I can persuade Boeing to let me hand the plane back at the end of the first year to protect the downside. So I knew the worst that could happen would be there would be six months of the profits of Virgin Records we would lose if it didn’t work out. Boeing agreed to it.” 

We tend to think that true success requires a risk-it-all, conquer-or-die mentality. Some may take this approach, but you don’t have to. Instead, you can mitigate the risk from big decisions taking an experimental mindset. 

Let’s say you’re a financial analyst thinking about becoming a software developer. The burn-the-boats approach is to quit your job and get a master’s degree or enroll in a coding boot camp. The experimental approach is to do an informational interview with your engineer sister-in-law, read a book on programming languages, or take a free coding course. 

Or maybe you’re at a Fortune 100 company and the startup world seems to be calling you. The burn-the-boats approach is to quit your job and move to San Francisco. The experimental approach is to attend tech meetups, find part-time work at a startup, or simply take a visit to San Francisco. 

You’ll never fully escape the risk-reward tradeoff, but small tests will help you achieve the greatest reward with the least amount of risk possible. It’s about unlocking the upside while capping the downside. Little experiments give you the data you need to make the big decision. 

Cortés may have achieved success by burning his boats, but you don’t have to.