Member-only story

Burn Your Boats! (Or maybe, don’t)

Cortés had second thoughts. You will too.

Paul Ollinger
5 min readMay 26, 2021
Is this image a little too ‘on-the-nose’? (iStockphoto)

Quit your job.

That’s what the cult of potential-achievement wants from you. They dare you to pull the ripcord, probing on their podcasts: “What would you do if you weren’t afraid?” (thus implying that anyone with a steady paycheck is a corporate cream puff).

Modern ninjas, they preach, live awesomely off-the-grid through entrepreneurship, the arts, or kite-surfing-mountain-climbing-veggie-juice-fasting in Bali. To make the point, these performance provocateurs cite historical badassery such as Spanish conqueror Hérnan Cortés who, upon landing the fleet in Mexico, demonstrated his commitment to the mission by torching his ships. This, you must agree, was the most rad bro-tivational move ever because in 1519 there was no uberX, let alone an uberFLOTILLA.

Six years ago, I abandoned a very lucrative career in digital media to pursue life as a writer and stand-up comedian. So I know a little bit about the tenacity of dreams and the realities of boat-burning. My informed point-of-view leaves me convinced that the Cortés headline (“Conquistador Blazes Barges, You Should Too”) tells only half the story, and that, in a moment of post-combustion clarity, Cortés summoned his second-in-command (Joe) to inquire on the state of his fleet. Here’s how it…

--

--

Paul Ollinger
Paul Ollinger

Written by Paul Ollinger

Comedian. Host of the Crazy Money podcast. Proud former Facebook and Yahoo! sales person/leader. http://PaulOllinger.com/podcast

Responses (5)