Pioneers, Privateers & Adventurers

In all ages, there come times when the epoch shifts from one to the other. In these moments of historical fecundity, where the ideas that will shape the coming era are writhing and fighting with each other to be born, there are vistas of great opportunity.

The Age of Exploration, the Industrial Revolution, the Nuclear age; these are some of the few poignant eras of this ilk in the past that we are most often familiar with. There are many others like them throughout the annals of history.

And these moments warrant a closer look indeed. Not only for their own sake, which I would advance is always a worthy endeavor, but because gentlemen, I would wager we are on the cusp of just such a similar age.

For many of you, this will be self-evident. The ‘Vibe-Shift’ is much talked about and conspicuously palpable. Executive orders abound and Elon is on a fat-trimming tear. But for those of you who need some convincing, try this on for size.

There is a discernable pattern in all previous ages where there is a dramatic shift (a revolution of some kind), just like the ones previously mentioned. First, there is a transitional period of great cultural torpor and retrenchment of fanaticism. The old ways are no longer sufficient, or they have created intractable problems that are swept under the rug by the current ‘system’, whatever that may be.

Catholicism prior to Martin Luther is exemplary. Regardless of your religious leanings or otherwise, the Holy Roman Empire and the Catholic church had massive problems that were fracturing much of European society. It took the spark of a precocious and fiery monk to light the tinder of a powder keg waiting to blow.

The reformation precipitated a massive shift in European political, spiritual and technological life. An entirely new era was created out of the ashes of an old, thanks to the coinciding of technological (the printing press), political (the independence of the German princes and protestant nations), and spiritual (Luther’s 95 theses and the derivative doctrines) innovations.

This sudden schism, from the old to the new, created an era of transformation. These eras are massive opportunities for those of talent, character and skill to study the zeitgeist and make great their fortunes in the burgeoning reality.

Now granted my history of the Reformation was incredibly truncated, but the pattern is illustrative. See if you can’t see the great historical rhymes from this era in what we are approaching now… if you look I’m sure you’ll see parallels.

We might, God forbid, find ourselves locked in the trenches fighting for the freedom of the island of Formosa (while our gen Z comrades give away our positions to drones via TikTok).

Or, God willing and probably more likely, we’ll find ourselves in an era likely approximating the Regan 80s… AI, drill baby drill, divestment from Blackrock, DEI schemes and the CCP, deregulation, etc… Pent up money, energy and ingenuity will be flowing in torrents.

There will be wide open vistas. Stakes to claim. Fortunes to be won and lost.

So, it is with this more probable and optimistic future in mind that I offer the lives, in a very much cherry-picked gashion, of three great adventurers from days of transformation gone by.

Not only is it deeply inspiring to see just how bad-ass our ancestors were (thereby pointing to the potential within ourselves), it is also deeply instructive to study the lives of history's great men to learn from their successes and failures.

So, let’s examine the life and times, in brief, of Sir Walter Raleigh, Captain John Smith and General Andre Massena. These men all lived balls-out, adventurous, extremely interesting lives. They did so in times when the very lines of history were being authored by men through their actions, noble or otherwise. In this spirit, they will likely prove worthy fodder for reflections on our own paths to success and happiness in this new era of adventure.

In order to avoid getting bogged down in unnecessary biographical detail, I want to lay out the scope of our essay to keep us focused on the material necessary for fruitful contemplation.

These men were adventurers and so I’m going to define what an adventurer is, using illustrative data from their lives. Then I’ll offer some examples of the high and low corruptions of an adventurer. Once we do this, then we can take each man’s life and examine it in turn through these lenses. This will, hopefully, make productive use of our time and mental energies. So, without further ado, let’s begin.

As with most issues of understanding along these lines, an adventurer is made from both nature and nurture. They generally start out seemingly primed to lead a life of daring. This was the case for all three men.

Sir Walter Raleigh had already fought in the War of Religions on the side of the Huguenots by the time he was a teenager. John Smith had been a pirate, successful soldier, captured, enslaved, and escaped from slavery all the way from Russia back to England by the time he was in his early 20s (wtf!!). Massena ran away from home at 13, became a sailor, then was soldier by the time he was 19, where he rapidly advanced in the enlisted ranks.

By the time these men were in their late 20s/early 30s, they were tough dudes who demonstrated extraordinary abilities across a range of situations. Mostly ones involving death and combat. So, we can already see, there is both a natural inclination to plunge into a life of adventure from an early age, but also the discovery and development of the skills and characteristics needed to survive and thrive through the journey. As we said, on the cusp of their early-middle adulthood, they’re primed for great things.

It's important to note as well that these men all found the vehicles necessary in the world to channel their adventurous spirits and hone their capable energies.

For Smith, it was leadership on the battlefield (and God knows what else to escape from slavery in Russia in the late 1500s). For Raleigh, he attended college after his early experience in war; where he learned law, philosophy and mathematics, all of which would serve him greatly in the future. Massena found the military where he rose through the ranks in peacetime quickly. His penchant for coloring outside the lines would never leave him either - even when he retired briefly pre-revolution (1789), he quickly took up olive oil smuggling to replace his King’s coin. Point being; they all found existing institutions or enterprises to participate in and shine.

We’ve seen their innate quality and how they grew their capacity, but what actually makes an adventurer successful? How do they execute their deeds? The answer is: a variety of ways, but it’s often leadership. Leadership comes from having both vision (as I’ve written about here) and the ability to bind men together in service of accomplishing that mission through it's end.

It can also come in a variety of other forms. For John Smith it was his military expertise that gained him initial leadership roles on the Jamestown expedition, but it was his diplomacy ability that propelled him into true leadership and secured his enduring legacy. He managed to trade with the Powhatan’s for the beginning two years of Jamestown, securing the colony’s initial survival.

Massena showed incredible endurance in the nascent days of the French Revolution when the Army of Italy was led by one incompetent general after another. He fought alongside the soldiers and ensured the army stayed together, despite the tumultuous political and leadership situations over the years. Eventually, Napoleon took command and he was able to subsume himself to a commander under whose leadership he thrived.

An adventurer must bring something exceptionally valuable to the table, we must work to discover and hone those qualities and capabilities within ourselves.

Finally, to round out our fulsome understanding of an adventurer, what is the ends of an adventurer? What is he really all about?

It’s simple really - an adventurer is about the new, he’s about victory. He’s about the intrepid. The charting of the frontier, the next critical invention, the next army on the horizon, the avant-gard artistic school. The ends of the adventurer is innovation and advancement. This is of course when all goes well, the ideal ends.

We’ll get to the pitfalls soon enough.

We now have a solid understanding of an adventurer from multiple angles, time and space, internal and external. He’s called to fulfill his potential from an inner knowing. He heads out into the world, finding a venue where he can test and develop his stuff in myriad ways. From there he hones his skills that differentiate him from the many other functionaries and bystanders in his midst. And all this is at the service, when the ideal matches reality, for a greater cause that brings forth the tides of history for the betterment of humanity, his compatriots and himself.

So how do things in the life of the adventurer tend to go wrong? What are some common pitfalls that we can look out for in our own lives?

As a student of philosophy (the real kind, not the fake academic stuff...check out Plato or Aristotle sometime if you don’t believe me), I like the dialectic between the high and low corrupted forms of an ideal.

If our ideal adventurer has already been laid out, how might forms of decadent and debased corruption of this ideal manifest? Well, I’m glad you asked dear reader, because I have some examples for you to ponder.

First, we’ll start with the low, the debased.

For the adventurer, this can often manifest in mercenary-ism or criminality. A mercenary can be independent-minded, enterprising and adventurous. A criminal may be charming, courageous and intelligent in the right circumstances. But it is the ultimate ends that he serves that truly differentiates an adventurous man from a mercenary or criminal.

It is ultimately a selfless, generous form of love that the adventurer must take to heart to separate himself. Love of health, life and goodness. In this way he will utilize his unique character and skills for the good, and steer away from perhaps tempting mercenary or criminal interactions.

This principle, however, is not always clear in reality. For example, John Smith took up piracy in the Mediterranean briefly on his way to join the Holy Roman Empire’s troops in the late 1500s. Though piracy was much more common in those days, and Smith was shipwrecked, then rescued by pirates en route to join the Austrian army, it could be argued that a more principled man would have refused this arrangement.

Far be it from me to judge a man of action in his dealings with 16^th century pirates, but it’s fair to say that this type of situation can still present predicaments in the modern world. A modern equivalent could be something like working in health insurance, an industry notorious for its dubious attitudes towards patient health. A mercenary, and arguably criminal enterprise in certain instances - max Novocain limits during surgery anyone? I digress.

Another version of this can be seen in the mid-career burnout of General Massena. He had a long victorious and valorous career, but by the time the early-Napoleonic years rolled around, something had changed. Who could blame him, he’d been a soldier nearly his whole adulthood, almost never resting from a life filled with dangers. However, this exhaustion started to take its toll.

In 1798 he was ordered to occupy the Papal States. However, things started to fall apart rather quickly. He was reported to spend much of his time womanizing and looting. This was a common practice in those days, especially in the Army of Italy as they needed to fund their own coffers with loot from the lands they conquered. But on a mission as diplomatically sensitive as this (Revolutionary France occupying the seat of European conservatism and religiosity) it was too much. It even got so bad that his troops became openly hostile to him, shocking for a man who had been a hero for so long. He was recalled from the mission and forced into temporary retirement.

This goes to show that even after a lifetime of honorable service, no one is perfect and getting tired will breed negative consequences if it’s not handled with care.

So we’ve seen some of the lows, let’s swing our sites to the high horizons. What does a decadent adventurer look like? How do successes and losing balance at the top of life manifest?

One such instance from Walter Raleigh’s life is instructive. Raleigh was famously Queen Elizabeth’s favorite. Through his power of charm and individuality, he seduced the Queen. This garnered him several monopolies and the backing for numerous colonial expeditions. However, this seduction was a two-way street that came with gilded fetters (more on that later).

Regardless, Raleigh became accustomed to receiving backing for his visions. Unfortunately, these voyages to the ‘New World’ and the glory and bounty sought in them became increasingly tenuous. The inability to execute on his visions culminated in two failed expeditions to modern day Venezuela, where Raleigh almost died from fever and was arrested by a displeased King upon his return.

The particular relationship between Raleigh and Queen Elizabeth, as well as the following discord with the proceeding regime, illustrates another point where adventurers can err. Their individual charisma can be both a boon – the seduction of the Queen and monopolies, and a liability - possessiveness of the Queen and alienating the court of King James.

One must be cognizant and prudent in order to wield one’s personal charisma effectively, especially at such heights. Failure to do so could put you with a view you don’t want, like the one Raleigh had from the Tower of London for 13 years before his eventual execution.

An extreme example no doubt. But consider the ways that you could smooth out your rough edges so as to avoid unnecessary rancor with those who would otherwise be neutral or perhaps even supportive of you.

Overall, we’ve explored a good deal of what the flesh on the bones of a life of greatness and adventure can look like. Far from the Hollywood caricatures, there are many important aspects of the good and bad, desirable and undesirable, that one needs to be aware of and manage effectively if one wants to live up to their own potential as an adventurer. And avoid the common pitfalls. Your life, after God and luck are done with it, is in your hands after all. Best to tend to it wisely. And have a little fun while we’re at it.

I hope this was edifying food for thought that evolves into wise and beneficent action. Thanks for reading. Much love.