Fortune Favors the Bold

Just a couple of years ago, Matt Damon appeared in a Super Bowl commercial promoting Crypto.com. "Fortune favors the brave," he told us. This was before the days of Sam Bankman Fried and FTX, and before Crypto.com faded into the land of broken promises. Many people lost LOTS of money. This leads us to question the premise - does fortune favor the brave and bold? History is replete with examples illustrating the merits and pitfalls of boldness and caution.

The Bold: Catalysts of Change
Boldness often propels individuals and nations to achieve extraordinary feats. Alexander the Great epitomizes this philosophy. In the 4th century BCE, his audacious vision led to the creation of one of the largest empires in history, stretching from Greece to India. His daring military strategies and relentless pursuit of conquest left an enduring legacy of Hellenistic culture, blending Eastern and Western civilizations. However, his early death at 32 underscores the potential risks of such audacity. For a time, he literally ruled all the world he knew - none could have had a larger fortune.

Similarly, the Age of Exploration saw intrepid adventurers like Sir Walter Raleigh and Ferdinand Magellan embarking on perilous voyages. Their boldness led to the discovery of new worlds and the establishment of global trade networks. The resulting exchange of goods, ideas, and cultures fundamentally transformed societies, though often at great human and environmental cost. However, Magellan was killed on his trip around the world while fighting natives in the East Indies - he was 40 or 41 years old. Raleigh was arrested and kept in the Tower of London for many years and was eventually beheaded. These men were both very brave and both amassed a fortune, at least for a while.

The Cautious: Architects of Stability
Conversely, caution has been a cornerstone of sustained success and stability. The Roman Empire, for instance, thrived for centuries due to its strategic conservatism. After initial phases of expansion, Rome focused on fortifying its borders and integrating conquered peoples through a blend of military might and diplomatic savvy. This cautious approach allowed the empire to maintain stability and prosperity over an extended period.

The Venetian Republic, flourishing for over a millennium, is another testament to the virtues of caution. By prioritizing trade, diplomacy, and a balanced governance structure, Venice navigated the tumultuous waters of medieval and Renaissance Europe. Its cautious policies ensured economic prosperity and political stability, enabling it to withstand external pressures that toppled many of its contemporaries. It was not until Napoleon subjugated the city-state that its self-rule came to an end.

Applying the Principles
There are many young people who live by the motto "YOLO." They are Thrillseekers who jump out of planes, bungee jump, BASE jump, and free climb buildings, mountains, and cliffs. They are certain brave, and they share their go-pro captured adventures on social media. Unfortunately, there are many tragic stories, especially recently, of the accidental deaths of these adventurers. When you risk death, sometimes death is victorious. Bailee Mulholland was 26 years old when she died free-soloing Blitzen Ridge in the Rockies. There are dozens, if not hundreds, like her falling while attempting to capture the perfect selfie.

On the flip side, there are billions of people who settle into their comfortable lives never to venture into territory outside their comfort zone. Their biggest thrill was changing their regular order at Chili's. Do they enjoy life? Probably, at least a little. However, they do not know what they are missing. Which leads to a philosophical question. Is it better NOT to know the adrenaline rush of the Thrillseekers? Perhaps the doomed climbers would still be with us today if they were not always searching for the next hormonal rush. The addictive nature of brain chemicals is powerful. It leads to many dangerous emotions - including the most lethal of all - love. It is said that all addictions (from cigarettes to heroin) are about finding a replacement for love. Is it truly better to have love and lost than to never have loved at all?

I digress here. Back to the main point. Fortune does indeed favor the bold. No one ever got superrich without taking a risk. Getting a 9 to 5 job and saving for retirement might yield you a "comfortable" retirement and a stable life, but you will not become "rich" - a powerful mover and shaker. Musk, Bezos, Zuckerberg, and even Trump took risks to get where they are, and they often failed. But is the kind of success they have achieved a good thing? It seems that these successful people are often the most miserable. They cover up their shaky emotional state with toys, trips, and sex. They generally have more failed relationships than "normal" people, commit suicide at higher rates, and often times their children resent or even hate them.

I recall Jordan Peterson discussing the lack of women in CEO positions at Fortune 500 companies. I paraphrase, "The question," he said, "isn't why there aren't more women in these positions, but why anyone would want one of these jobs at all." CEOs of these companies are under constant stress. They have no real time off. Global companies operate 24/7. They are always on the chopping block if things go wrong and all for what? A great compensation? Studies have shown increased income beyond enough to cover middle (perhaps upper-middle) class living expenses, retirement savings, and a nice vacation every year does not increase happiness. So why pursue this? To win the game of life?

In the 1980s, time of the Yuppies, there were t-shirts and bumper stickers that said, "Whoever dies with the most toys wins." Ah, materialism at its finest. In reality, deathbed confessions reveal that people's biggest regrets include working too much. Nowhere to be found in the biggest regrets was not accumulating enough toys. What a stupid slogan.

Perhaps the point here is this: Yes, fortune favors the bold, but is "fortune" what you really want anyway? Wouldn't it be better to be a little more cautious so you can be around a little longer to enjoy the things that actually provide happiness? Family, friends, travel, and adventure. These are the things that give our lives meaning.