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Why Some Succeed

A strong sense of “why” can produce surprising success.



My friend Cindy Werhane is preparing for the challenge of a lifetime. As I write, she is less than 24 hours away from starting a 38-mile swim around Oregon’s Sauvie Island. As part of a support crew, I’ll be on a sailboat alongside Cindy, observing, cooking, cheering, spotting barges at night – even swimming alongside at times.

What would it feel like to cover 38 miles over 25 hours? It’s hard to imagine, particularly the mental aspects. Even as we’re determined to help her finish, few of us aboard will truly know what she’ll endure.

Cindy likes to say “know your why,” which reminds me of Simon Sinek saying, “People don’t buy what we do, they buy why we do it. Find your why.” And it reminds me of Viktor Frankl’s “Those who have a ‘why’ … can bear with almost any ‘how.’” 

What I’ve learned from watching ultra-endurance athletes – and great businesspeople – is that purpose is infectious. But more than anything, that a strong sense of why can produce surprising success from surprising people. 

What’s hard about this, in my experience, is that from the cozy confines of a climate-controlled room, it’s easy to craft a reason to persist in difficult times. Yet, when hardship occurs – when the water is colder than you expect, when your hoped-for nighttime kayaker has to work instead, when you’re tired and sore and nauseous – well, it gets harder. 

Company owners that I’ve seen who “have it” often have a story. Their business is solving a problem they encountered, or it’s offering an opportunity to those whom others might shun as employees. Some owners are finding success as first-generation Americans, with a nod to their parents’ sacrifice. Other times, they’re keeping the legacy of a family business alive. 


“Making money” is never the sole secret to success. You need something that encourages you to stand up when it feels like the heavy foot of the world (or, sometimes, the bank) is on your shoulder. That can be internal. It can also be from your own support crew, people you’ve let into your dream. People who have seen your vulnerabilities and doubts, and who can shake you out of a funk.

I love Sinek’s TED talk; search his name and “find your why” on YouTube. Then, spend some time searching yourself. Why wake up in the morning? Why do what you do? What would inspire you when the opportunity comes to tackle the challenge of a lifetime?

You may be surprised to find – once you’ve discovered your why – that the opportunity is already here.



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