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Posted by on Jun 21, 2015 | 0 comments

Overcome Hesitation by Thinking Like a Billionaire

Overcome Hesitation by Thinking Like a Billionaire

“Some prophecies are self-fulfilling,
I’ve had to work for all of mine…”

The quote above is a favorite lyric of mine, from the song “Lawrence, KS” by Josh Ritter, a New York based Singer Songwriter originally from Idaho. Beyond this post, (for which this verse will have particular meaning), I highly recommend both song and artist.

Recently, on a train to Manhattan I read a short story about Richard Branson and this lyric came to mind. The story was about how Branson made the decision to start Virgin Airlines. A quick summary:

While still in his mid-twenties, and a relative unknown, Branson was at an airport awaiting a flight to the Virgin Islands when it was cancelled due to maintenance concerns. “I had a pretty girl waiting for me and I was determined to get there on time,” Branson says.

With this determination in mind Branson made arrangements to charter a plane. With no money to pay for it, Branson quickly crafted a sign that read, “Flight to Virgin Islands, $29” and approached the group who’s flight had just been cancelled. Within minutes he had sold all available seats, paid for the flight and turned a small profit for his effort. Within a few years, Virgin Airlines was a brand and Branson was a billionaire.


Lately, I’ve found myself giving a lot of thought to the word “Effort”. In recent posts I’ve talked about innovation and initiative and passion and fear. Today, with Branson’s story in mind, I’d like to talk about Effort and, what I believe to be its polar opposite, “hesitation”.

For those who have read previous posts, you’ll understand why I consider “Hesitation” the opposite of “Effort”, rather than “Laziness” or “Passivity”, “Idleness” or “Inactivity”.

“Hesitation”, unlike its synonyms, implies a conscious and calculated assessment of the situation, rather than merely a blasé unwillingness to act. This may seem like splitting hairs, but it is a critical difference when dissecting the nexus of effort, or as we explore the unique differences that exist between those who consistently act, and those who choose not to.

What’s so interesting about effort is that life, as tied to any specific instance or scenario, rarely demands much of it. That’s not to say that hard work is not, or will not, be required but only that the first step (especially in hindsight) is never as complex, daunting or vigorous as we imagine at the time. Nor, for that matter, does effort often owe itself to bursts of inspiration for which few are capable.

Branson’s decision to charter a flight took very little effort and wasn’t particularly brilliant.

In the wake of a cancelled flight, how many of us have contemplated alternatives, mulled over the options, weighed the cost-benefits of each scenario, only to shout at the customer service representative and grudgingly leave the airport?

Ultimately, it is this very act of contemplation, of asking our minds to sort out the “pros” from the “cons” that gives any effort undue weight and convinces us to hesitate, to accept the hand we’ve been dealt.

By contrast, people like Branson, who have trained themselves to act, don’t spend any real time developing a strategy. They are constantly looking for an opportunity to do something, rather than waiting for a chance to decide. In this way, strategy and tactics follow action, not the other way around.


One of my favorite books, “The Alchemist” by Paulo Coelho, is about a young man who receives a prophecy from a fortune-teller that he will discover a great treasure if he believes ardently enough. Throughout the story, providence consistently rears up and pushes the young man closer to achieving his dream.

Many have interpreted this story through the lens of “The Secret” or The Law Of Attraction, which concludes that we have the power, through intense focus, to influence the universe around us. I disagree with this interpretation.

Rather, I read it as the story of a man who makes a series of very simple decisions that most would chose not to make, and which build the foundation for providence, the fulfillment of prophecy. None of his decisions are critically difficult, but each is rooted in a willingness to take action (bolstered by self-worth) where others would accept circumstance.

And so we come back to Ritter’s lyric and figures like Branson, for whom hesitation rarely occurs and who refuse to ask one of the most damaging questions we may ask ourselves: “How?”

“How” is a dagger that plunges Hesitation into the heart of Effort and kills the innate ability we all have to identify creative solutions to life’s common problems. “How” asks the mind to discover logical reasons to justify an act of will. The next time you find yourself asking “How” something can be accomplished, tell yourself “Why” it should be accomplished and take action, instead. This may not always be met with success, but you’ll be no worse for the wear and you’ll train your mind to act when it matters most.

Most of us ask “How”. We build thought bridges that lead to nowhere. We ask our prophecies to self-fulfill. We leave the airport and board taxis that will conveniently deliver us to our destinations tomorrow while people like Branson stand up, walk to a different counter and charter a plane that will take them where they want to go, today.

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