In 1992, Bruce Springsteen delivered an song called “Local Hero” that has one of the best lines he ever wrote. It goes like this:

These days I’m feeling alright, ‘cept I can’t tell my courage from my desperation.

This is true for most of us, isn’t it? Our moments of genuine courage are also moments where there doesn’t appear to be any other choice. This isn’t meant to downplay courage—only to clarify its origin. We can all be courageous when necessary.

You see it regularly: a news reporter interviews someone who performs an act of heroism. They ask the hero why they did it and the hero often says, “It’s what anyone would have done.”

The humility is deeply admired. And I like to think the statement is true.

Courage is hard, however, when we have a choice. If there are options at our disposal, then maybe it’s best to examine this situation a little while. Let’s talk it through. Let’s find a more creative (i.e., less fearful) solution. Such is the attitude that emerges when, again, there are choices to weigh. So Bruce’s song lyric has a real chord of truth to it: courage and desperation have a lot in common.

Want to become courageous? Eliminate your options.

Alea Iactca Est

Almost 2,070 years ago, Julius Caesar led a legion of troops over a river in Northern Italy called The Rubicon. As rivers go, the Rubicon is a bit narrow and quite shallow. But Caesar knew the depth of his action once he had crossed its banks. In doing so, he had stepped out of the Gallic provinces and into official Roman territory. With his army following behind him.

To lead troops into Rome was a violation of the Roman law of imperium. Caesar had no right to do this. It was a flagrant act of rebellion. Civil war ensued and the rest is history.

Again, all because of a single act that could not be undone. Upon his crossing of the Rubicon, stepping past the point of rescue, Caesar reportedly stated the latin phrase: Alea iacta est. In English, this translates to “the die is cast”. There was no going back.

The Road To Tenochtitlan

Centuries later, the Spanish conquistador Hernan Cortes faced his own Rubicon on the shores of Mexico. Though he originally ventured to Mexico to settle the town of Vera Cruz and return to Cuba soon after, the Spaniard appears to have suffered a damaged fleet when his crew made landfall. Cast upon on the shores, with a settlement to build and repairs to be made, there was no chance for him to leave any time soon.

As the settlement began, a group of Aztec emissaries visited from the nearby villages. Eventually, even the great Montezuma dispatched his own band of messengers. Cortes learned more about this native people and soon discovered that he was only a few days’ ride to Tenochtitlan, that fabled city of gold.

It was the chance of a lifetime. Armed with this knowledge, Cortes felt he had no choice.

Many of his men wanted only to repair the ships and return to Cuba. Cortes, however, knew that there would be no better chance for him to find glory and wealth. The crew resisted, a mutiny nearly erupted, and Cortes quickly acted. Rather than tempt his men with any further thoughts of a retreat, he burned the boats.

With no possibility for retreat, no other options, the die was cast once again.

Most Things Deserve Optionality. For Now.

If Caesar and Cortes had failed their missions, the talk of Rubicons and boat-burnings would be a cautionary tale. We would view it as an example of the worst sort of hubris: the brash, indulgent kind. I would quote Ralph Waldo Emerson’s line to Oliver Wendell Holmes:

When you strike at a king you must kill him.

I would also write about exit strategies. How there must always be a backup plan. I would highlight the manner in which every engineer, regardless of his confidence, keeps a redundancy or three.

This is the stuff of management. I’ve written about it ad nauseum. Distributed risk, barbell strategies, asymmetric small bets in power law dynamics, incremental change through upside risk, small dances with uncertainty. Test multiple options. Don’t jump blindly.

This is how most things should be done. Robert Greene’s study of The 33 Strategies of War explains the idea clearly enough, too:

The essence of strategy is not to carry out a brilliant plan that proceeds in steps; it is to put yourself in situations where you have more options than the enemy does.

But this wisdom does not apply at all phases of a new venture. And if you read it the wrong way, you might find a contraction with this and other strategies that Greene shares in this great book. Cultivate options, sure, but don’t bury yourself in optionality? What does this mean?

Small bets and experiments are a fine way to either determine where we go or how we get there. But if we don’t operate from an all-or-nothing, no-turning-back level of commitment, we’ll fold when things get hard.

To that end, it’s important to remember how these courageous moves and intelligent tactics come together. Any new venture that we might call “entrepreneurship” is a Rubicon-esque endeavor. It is an effort that requires one to burn their boats. Forget the probabilities, the distributions, the error rates. This is calculus, not  statistics.

Smart Courage for Big Bets

In a recent interview on the Tim Ferriss podcast, the writer and educator Jim Collins talked about his own Rubicon when he stepped out of the safe comfort of academia and into the world of creative entrepreneurship. Years of teaching business and entrepreneurship to students at Stanford University kindled a yearning within him. He wanted to take the leap himself. This is fascinating to me since Collins already had a dream job. Professorship at Stanford? Who would ever want to give that up?

Might as well ask why Cortes would want to venture into the heart of Mexico.

But Collins was smart. Collins had a master’s grasp of management theory and practice and knew there would be value in keeping some connection to Stanford in the event that his new business venture failed. In talking to a colleague, Irv Grousbeck, about his launch strategy, Collins recalls:

I asked Irv, “Do you think I should keep enough capital alive here at Stanford that if this doesn’t work out, I could come back?” Irv said to me, “An option to come back has negative value.” I said, “I thought options always have positive value.” He said, “No. Not on a creative path.”

This already echoes the wisdom from Ben Horowitz. Collins continued to recite the rest of Grousbeck’s advice:

“If you have the option to come back, it will change your behavior. You’re doing a low odds game, which means you have to put all in, 100 percent, full cannonball, go off that cliff. Otherwise, you’re going to hold something in reserve. When it gets really scary, you’re going to pull back. Option is not in your interest.”

It should be noted, however, that this was not a big, dumb leap into the unknown. Collins was able to make a big bet like this because he had developed a deep, rich understanding of his audience, his market, his service, and his book. He had built this knowledge with a practice he refers to it as “Fire Bullets, Then Fire Cannonballs.”

The idea here, featured in his book Great by Choice, is akin to setting sights on a target. To do so, a marksman first spends some time firing small (i.e., cheap) bullets at a target, calibrating the optics and trajectories, learning the distance and necessary gunpowder. After a number of adjustments, accuracy is gained and the target can be reliably hit at-will. With this “calibrated line of sight”, it’s time to fire the big cannon. The big, expensive launch.

Options: Use With Caution

This is akin to the best principles of Lean Management and it’s orthogonal to great design thinking. The idea here is that you make a big bet only when there is enough signal and information to justify the big bet as a safe bet. Optionality helps to determine the direction in this case prior to a leap. Optionality also helps in changing course (slightly) after the leap when obstacles are encountered. But the leap still must occur. The idea that there is no additional options, no backup plan, is still necessary.

For Collins, this effort of “firing bullets” took nearly seven years. His big leap was a long time in the making.

For Caesar, the crossing of the Rubicon came after several successful campaigns in Gaul, the culmination of years of study, leadership, and a pattern of victories that turned him into a national hero.

For Cortes? Well, he appears to have been a bit more desperate. He was facing criminal charges from the Governor of Cuba, severe debt for burning the boats, and the potential mutiny of his men. Great startups have been born under less pressure. But not much.

This gets to the other aspect of Greene’s tactics and insights from The 33 Strategies of War. Remember, I previously cited a passage of his that advises you to develop options. At first glance, this next passage appears to contradict those words:

Because you think you have options, you never involve yourself deeply enough in one thing to do it thoroughly. Sometimes you have to become a little desperate to get anywhere.

That was Cortes. And if that wasn’t Caesar, I bet it was Caesar’s troops. Additionally …

Often we try too many things at one time, thinking that one of them will bring us success–but in these situations our minds are diffused, our efforts halfhearted. It is better to take on one daunting challenge, even one that others think foolish. Our future is at stake; we cannot afford to lose. So we don’t.

I don’t know about you but that last passage, about trying too many things at once, is probably the biggest problem I face. To try multiple things, start multiple endeavors, is to barely dip one’s toe in the “waters of uncertainty”. Again and again. Never leaving dry land.

To try one thing, in multiple ways, is to wade deeper into the water. Eventually finding a way to swim. This is what Greene is referring to when he mentioned the need to “involve yourself deeply”.

So how should one burn their boats properly? Perhaps by taking the calculus approach (there is a single answer; you must find it; here we go) and, secondary to that, the statistics approach (I’ll develop and calibrate my search for an answer in these structured ways).

Rome wasn’t built in a day. The right answer isn’t found overnight. The best approach, it seems, is to give yourself the luxury of time to find the right answer without the luxury of abandoning the problem.

To have the desperation and courage to start, with the wisdom to build options ahead of every obstacle, while powered by the persistence that comes from an inescapable necessity for a certain outcome, seems to be the best strategy of all.  

To close, I’ll offer another line from another Springsteen song: No retreat, no surrender. It’s the banner of many a foolish venture. Greene’s book is full of examples. It’s also the banner of many a success. Burn the boats. But not until you find a path to the city of gold first.

Image by Miguel Gonzalez, Wikipedia