When you’re in a good position, there are multiple ways for you to win. When you’re in a bad position, there’s only one way for you to win, and it requires some divine intervention.
This analogy is balanced out by ancient wisdom: The night before a critical battle, an army’s general ordered them to burn the boats that brought them there. There would be no turning back, only moving forward. It was victory or death. The army fought with desperation and won the battle, and the war.
You want to create multiple paths to succeed. Burn the boats only when you’ve committed to a path, and decide there’s no turning back.
Deciding when to burn the boats is a matter of judgment. What’s right for you could be wrong for someone else. Here are some signposts to help you decide:
There are two types of options: live ones and dead ones. It costs money, time, and energy to keep an option alive. If you’re keeping too many options alive, you will not be available to nurture any of them meaningfully. You will not recognize their potential. If you find yourself struggling to focus, it’s time to consider burning the boats.
If an opportunity falls into your lap, with a huge margin of safety to try something new, it’s worth at least exploring it further. Could you shape the option so that pursuing it for even just a few weeks or months would be worth it?
When I worked independently, clients approached me to join their company full time. I declined until one particular option came with a very sizeable salary, which felt like a margin of safety to me. Until then, I was very focused on succeeding independently. Looking back, if I had been more open to some of those prior opportunities, that could have been interesting as well.
A backup plan is fine until maintaining it eats into the main plan. If it does, and there is a clear path for your main plan to succeed—it just requires more of your focus—you may need to decide to burn the backup plan and go all-in. Make sure your backup plan doesn’t mess up your main plan.
If you don’t see a clear path to success, and you’ve run out of resources, don’t burn the boats. Don’t take on more risk. Quit. Turn around and re-evaluate your options.
A few years ago, I wrote full-time for several months. I ended up writing a book, and many good articles. However, these projects didn’t generate enough income for me to sustain it. I was considering liquidating some stocks to buy more time—in other words, burning the boats. There was no clear path to success for me at that point—no big payout, no book advance, no huge audience growth. So I quit writing full-time. I considered my options, and signed up for a full-time job. I also looked for opportunities to write outside of that. While it felt like a painful decision, it was also one of the savvier ones I’ve made, and my writing is actually better for it.
Maybe a more succinct way of describing the previous story: you can only burn the boats so many times, and that definitely didn’t feel like the right time for me. I’m certain there will be a better opportunity to burn the boats in the future.
Sometimes you need to take a precursive leap of faith on yourself. Make sure you can afford to take the risk.
When I quit my job, friends asked me what I was running away from and what I was running toward. If you’re running away from something, sprint. Half stepping will cause you to stumble. If you keep looking backwards, you’re going to trip moving forwards.