An Unusual Success Strategy

Here’s an unusual success strategy you should consider when balancing the risks of failure against the possibility of taking action.

An Unusual Success Strategy

When I was young, I loved riding around the countryside in a pickup truck with my father.  We traveled frequently to and through Farmersville, Kentucky, the small, rural community where my dad grew up. 

Time and again, while passing through, my dad would point out a specific parcel of land and comment, “I should’ve bought that farm when your Mother and I first got married.  It could’ve been ours for almost nothing then.”  Upon delivering those words, his voice would usually drift off, giving way to silent, wistful thinking.

My dad never bought that farm.  And I’m sure he never stopped regretting it.  My dad’s gone now, but I still think about those truck rides.  And almost every time I pass that farm I remember his words.  They’re as clear in my mind today as they were fifty years ago when I first began hearing them.  

I Should’ve Bought That Farm

“I should’ve bought that farm…” Those truck rides and my dad’s reminiscing left their marks. His experience cemented an unusual success strategy I regularly embrace and employ.

It’s an unusual success strategy, but one you might consider. Here it is:  If I am to fail, I choose to fail aggressively.

This choice took root in my consciousness years ago, while I was reflecting on my Dad’s lifelong regret over not buying the farm.  Though there’s no way of knowing for sure, I’ve concluded that it would’ve been preferable for my father to have borrowed the money, bought the farm and ultimately, lost the farm for any number of reasons rather than endure decades of lamenting “what might have been.”  

Now, I am not condoning a foolish fiscal attitude that would lead you to buy what you cannot afford, without a legitimate plan for repaying the debts you incur.  That’s not a common sense success strategy.  We should always stand responsible for the commitments we make, be they financial or otherwise.    

unusual success strategyWhat I am suggesting is this. The power of regret can be more debilitating than the embarrassment of failure. I’ve watched its effects firsthand.

Here are four questions to ask yourself as you encounter situations that might seem a bit risky on the surface.

My Unusual Success Strategy: Fail Aggressively

In view of that, I’ve decided  I would rather fail aggressively than passively. In other words, I would rather fail trying to make something happen, instead of sitting on my hands watching things happen, or regretting the lost opportunity. 

Humorist Mark Twain sounded a serious note when he penned the following words regarding risk and regret. 

“Twenty years from now you will be more disappointed by the things you didn’t do than by the things you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream.”  

That’s good advice.  But there’s one other important point that needs to be made concerning the act of “sailing from the safe harbor.” Once you choose to try, and you commit to moving forward, taking action — you may be pleasantly surprised to find failure is not a given after all.  

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Failure is not inevitable.  Once committed to something, most people are able to summons up the will, imagination and find multiple strategies to succeed.  Losing the farm was not a given for my dad.  I’m convinced he and Mom would have found a way to make the purchase successful.   

Nineteenth century author, poet, historian, and philosopher Henry David Thoreau put it this way.

“If one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with success unexpected in common hours.” 

I happen to agree with Thoreau.  I’ve found that many people succeed in their personal and professional pursuits because they don’t fear failure and move confidently forward, discovering success at various stages throughout the process.    

What About You?

In the pursuit of success, how willing are you to embrace or tolerate your own failure? Are you…

  • Low Risk: I always play it safe.
  • Med Low: I hedge all my bets.
  • Med High: I’ll take a hit or two.
  • High Risk: If I fail, I still win!

Curious what other people say? Take the LinkedIn poll and see.

For more unusual success strategies like failing aggressively, check out Leaders Ought to Know: 11 Ground Rules for Common Sense Leadership.



Phillip Van Hooser
Author: Phillip Van Hooser
Phillip Van Hooser, CSP, CPAE is committed to helping organizations transform their business outcomes by building engaged employee relationships. He is an award-winning keynote speaker and author on leadership, service and communication. His popular book, “Willie's Way: 6 Secrets for Wooing, Wowing and Winning Customers and Their Loyalty” recently hit #1 in Customer Relations on the Kindle store. Connect with Phil on LinkedIn and Facebook.

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