The Secret of Success (According to a Middle-Eastern Philosopher and an American Cartoonist)

The Philosopher and the Cartoonist

The Middle-Eastern philosopher is Nassim Nicholas Taleb.  Taleb is a Lebanese-American author, academic, statistician, and philosopher.  He achieved riches in bond trading and fame from his best-selling books Fooled by Randomness and The Black Swan.  He is pretentious, overbearing, and arrogant.  He believes he has the world figured out and he sometimes openly mock his critics in his writing.

The American cartoonist is Scott Adams, creator of the Dilbert comic strip.  Adams is also a best-selling author.  He is sarcastic, self-deprecating, witty, and he openly mocks himself in his writing.  He says things like “I’m…not an expert at anything, including my own job.  I draw like an inebriated howler monkey and my writing style falls somewhere between baffling and sophomoric.  It’s an ongoing mystery to me why I keep getting paid.”  To destroy any remaining credibility he adds, “I’m not too proud to admit that given a choice between saying what’s true and saying what’s funny, I’ll take the path with the greatest entertainment value.” 

Taleb and Adams could not be more different in profession, personality, or writing style.  The one thing they have in common is success.  By just about any measure, financial or otherwise, each has been wildly successful.

In their latest books Taleb (Antifragile: Things That Gain from Disorder) and Adams (How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life) disclose the secrets of their success.  The books are as different as the authors, but despite their differences the philosopher and the cartoonist have remarkably similar theories on how to succeed.    

Taleb’s Philosophy of Success

Taleb’s success philosophy is based on two concepts: “the barbell approach to risk” and “asymmetric payoff.”

The barbell approach calls for taking very little risk in most areas of your life coupled with extreme risk in select areas.  Taleb describes this as “aggressiveness plus paranoia.”  Everything is either very low risk or very high risk, with almost nothing in between – thus the barbell analogy. 

The risks you do take should present the opportunity for “asymmetric payoff,” meaning potential losses should be limited while potential gains should be unlimited.  At the risky end of the barbell you should focus less on the probability of success and more on the consequences.  If you can sufficiently minimize potential losses while exposing yourself to unlimited gains a risk might be smart even if the probability of success is low.

In investing the barbell approach might consist of putting 80-90 percent of your money in very safe investments and then taking extreme risk with the other 10-20 percent.  Using options to limit downside risk while creating exposure to unlimited gains is one way to accomplish this.      

The barbell approach can be implemented on a broader scale by choosing a very safe, secure profession and then taking risks on the side that cost very little but have the potential for huge payoffs.  Taleb calls this “tinkering.”   As examples he cites the extraordinary number of scientific breakthroughs during the renaissance which were made by Catholic priests.  This was possible because the priests had secure, well-paying jobs that allowed them the free time and flexibility to work on projects of their choosing on the side.

Failing His Way to Success

Adams describes his book as a “tale about a guy who failed his way to success.”  After graduating from college in New York he bought a one way ticket to California where he secured a safe, boring job at a bank.  Eight years later he left the bank for a similar job at a large phone company.    

With the safe side of his barbell weighted Adams immediately started trying to strike it rich with one high-risk/high-reward plan after another, all of which failed spectacularly.  With each failure he learned skills and gained contacts that made future success more likely.  Most of his side projects didn’t cost him much more than time. 

Adams eventually stumbled onto the idea for Dilbert, which allowed him to combine his intimate knowledge of corporate culture with some of the other skills he had developed along the way.  The rest, as they say, is history.    

Adams is completely unafraid of failure.  He believes that, “failure is your friend.  It is the raw material of success.  Invite it in.  Learn from it.  And don’t let it leave until you pick its pocket.”  In other words, on the risky side of the barbell don’t be afraid to take longshots if potential losses are small and potential gains are large.

Adams sums up his philosophy on success as follows:

“I find it helpful to see the world as a slot machine that doesn’t ask you to put money in.  All it asks is your time, focus, and energy to pull the handle over and over.  A normal slot machine that requires money will bankrupt any player in the long run.  But the machine that has rare yet certain payoffs, and asks for no money up front, is a guaranteed winner if you have what it takes to keep yanking until you get lucky.  In that environment you can fail 99 percent of the time, while knowing success is guaranteed.  All you need to do is stay in the game long enough.”

Think of the Successful People You Know

When I think of the most successful people I know it is clear that many of them employed the techniques taught by Taleb and Adams.  For each one I can name several “failures” in their lives, and yet they are undeniably successful.  This is because their failures weren’t all-or-nothing gambles but calculated risks with asymmetric payoffs.  They just kept yanking the handle on the free slot machine called life until it paid out.     

Think of the successful people you know and tell me if you see this same pattern.  My guess is that you will.  Success is never guaranteed, but using the concepts of the barbell risk approach and asymmetric payoff greatly increases the odds.  It certainly worked for a Middle-Eastern philosopher and an American cartoonist, so keep yanking on that handle.