The Conquest of Your New World

"And as the moon rose higher the inessential houses began to melt away until gradually I became aware of the old island here that flowered once for Dutch sailors’ eyes—a fresh, green breast of the new world. Its vanished trees, the trees that had made way for Gatsby’s house, had once pandered in whispers to the last and greatest of all human dreams; for a transitory enchanted moment man must have held his breath in the presence of this continent, compelled into an æsthetic contemplation he neither understood nor desired, face to face for the last time in history with something commensurate to his capacity for wonder." - F. Scott Fitzgerald, The Great Gatsby

That's pretty reading, but it's pretty crappy history. Fitzgerald is projecting the modern man's paralysis in the face of unlimited opportunity on the discoverers, colonists and conquistadors of yore. But he has done me a service, providing a powerful illustration of the contrasting ways you can approach the seemingly infinite horizon of financial freedom.

Fitzgerald's imaginary Dutch sailors react as so many of us do the prospect of financial independence: with starry eyes, whispered tones and breathless reverie. It should be obvious that none of these childlike expressions of awe are consistent with the Herculean efforts it took to reach those fertile shores in the first place. The men who discovered and tamed the New World were not dewy-eyed dreamers but ruthless venture capitalists and religious zealots driving half-mutinous crews of hardened men halfway across the world in search of fortune and glory.

They were not compelled into "aesthetic contemplation they neither understood nor desired" at the sight of the New World. To the contrary, it was exhaustive contemplation on matters that they thought they understood and desired more than anything that led them to compel the Americas and their inhabitants to submit to their careful designs.

If you remember from part I of this series, it is rage against the tyranny of debt and wage-slavery that leads us to attack our financial bonds. But once those shackles are gone and those tyrants are slain, how do we keep feeding the tree of liberty? What do we do with this freedom? The first trick is not to fall into the Fitzgerald wonder trap and slip into an aesthetic contemplation.

The Fitzgerald wonder trap that he ascribed to the explorers is probably a better description for the reaction of the natives to the new arrivals. The sight of the Spaniards trigger an existential crisis on the part of the previously invincible Aztec elite. The Incans, conquerors themselves, were lulled into strategic retardation by Pizarro.

The better models, in strategic behavior if not morality, are the colonists and conquistadors. They manfully resisted Fitzgerald's compulsive contemplation and sprang into action. It was their lightning decisiveness that gave them the advantage again and again over their native foes, leading to their amazingly rapid blitzkrieg style conquests of huge empires.

Viewed from the conquistador lens, the horizon is not infinite - it is a border, and behind that border are territories held by other men, some friendly, some neutral, some hostile. You cross that border not with unlimited resources, but a relatively pitiful handful. After all you are brand new to financial independence. Most of the people in front of you have been there for generations.

Time is short, money is short and your only safety net is heading back into wage slavery or debt with your tail between your legs. It's time to do as Cortes would do (Hernan Cortes, but Alexander Juan Antonio Cortes works too).

1. Plant Your Flag: On his arrival in the New World, Cortes still had to sever the clinging ties of the Old World. He did so by formally incorporating his own settlement and electing himself Captain-General. While the settlement was little more than hot air when he announced it, it established his claims to ownership. It was the scrap of territory that would grow into an empire. In the same spirit, if you want to conquer, you have create a wedge to conquer from. This means picking a specific starting point and putting down some roots. It means giving yourself a clearly defined role with associated responsibilities. And it means putting in a claim for what you eventually want to make yours.
2. Scuttle the Ships: After dealing with a mutiny, Cortes scuttled his fleet to force them to commit to conquest. Similarly, just because you're entering a new world of financial freedom, doesn't mean you aren't still the sum of a lot of old world parts. A lot of you is still going to want the security of a boss and a McJob. A lot of you is still going to want the stuff that doesn't matter and will be willing to go back in debt for it. So if you want to conquer, close off the escape route. 
3. Recruit Allies: Climbing out of debt doesn't always require getting help, but waging a war of conquest in occupied territory certainly does. A huge key to the transition from the freedom "froms" to the freedom "tos" is finding people with shared ambitions to partner with. Cortes found the unpronouncable Tlaxcalans. The only things they had in common were warlike dispositions and a desire to take down the Aztecs, but that was enough to forge a lethal strategic partnership.
4. March on the Target: Even with an outpost established, no way back, and allies at his back, it still took guts for Cortes to commit to taking on the strong man in the room - the Aztecs. But his ambitions were such that there was no other way. If you don't want to settle for less, than chances are you are going to be facing down strong men who currently possess what you want - market share, property, a media megaphone, political power, etc. Even if your ego is soaring, it's still an intimidating prospect. But you can't win if you don't play. So commit to the competition.
5. Be the Bigger Man: You might think of the bigger man as the guy who takes a slight or a loss with more dignity, but I mean it as a contest of stature. Cortes vs. Montezuma (and his later successors) was not decided by dignity. It was decided by who was better able to play the hand they were dealt. Montezuma lost not because he was outgunned - he enjoyed huge advantages in several respects. Nor did Cortes win because he hit a phenomenal lucky streak - he had to deal with an enemy conquistador in the middle of his campaign. Rather the man most capable of weathering and adapting to overwhelming adversity survived long enough to win the day. Let that be you.