Find Your Why: The Psychological Guide to Starting Up

June 7, 2013

11:00 am

This post is part of Tech Cocktail’s “Psychological Guide to Starting Up” bringing you insights on the psychological and emotional challenges of startups throughout June.

It’s as basic a question as it is indicative of an entrepreneur’s likelihood for long-term success.  Why do you do what you do?

Simon Sinek gives us all the reasons why “why?” will help you recruit better talent, connect with customers, and thusly improve the bottom line.  Undeniably this matters.

But even in an ideal scenario, a favorable bottom line is a long ways off.   Starting up is a game where failure is the rule.  What separates the exceptions?

Money, connections, maybe a superior idea?  

Perhaps, but these are tangible byproducts that involve much blood, sweat and luck.  What qualities allow an entrepreneur to get this far?

Persistence, determination, hustle?

Yes, but only indirectly.  Staying determined for determination’s sake is rarely a reliable tactic- and is likely the reason why you’re willing to trade in the comfort of your 9-5.  So what lies at the nucleus of the successful entrepreneurial cell?


Asking yourself why you’re doing what you’re doing offers a window into your purpose.  Living with purpose is the biggest predictor of success.

Appalachian Trials

Although I’ve successfully exited as many startups as Dan Marino has championship rings (zero, for the non-NFL fans), I have completed an endeavor with a similar failure rate: thru-hiking the Appalachian Trail, a footpath that extends from Georgia to Maine.  Roughly four in five attempting thru-hikers quit prior to covering the full +2,180 mile distance, with the majority falling off before the halfway point.  On paper, I was destined to join this unfortunate majority, as the AT would be my first backpacking trip.  Of any distance.  Ever.  I had slept in a tent twice in my life, pitched my first only three days prior to embarking, and built zero campfires.

My unlikely success stemmed from finding my purpose.  Before leaving for the trail, I asked myself three very basic questions and wrote the answers down in my trail journal.  They were:

  1. Why am I doing this?  Here I wanted to accurately uncover all the reasons someone with no backpacking experience was going to spend the next half year in the woods.  There were many.
  2. What benefits will I get from following through? These answers would reveal the personal benefits I hoped to acquire from completing this journey.
  3. How will I feel about myself if I quit?  Similarly these answers would reveal all the negative emotions I would undoubtedly live with if I fell short.

As part of the exercise, I forced myself to dig deep into my psyche, unearth some uncomfortable emotions, and honestly examine what was pushing me onto the trail.  “Because it seemed exciting” was the surface answer, but underneath that was a desire to build confidence, be more interesting, and refuse mediocrity.

From that point forward, my options weren’t merely to keep walking or go home; my fork in the road lead either to lifelong happiness or self-loathing (maybe a bit extreme, but you get the point).  I found my purpose.  When confronted with a lightning storm above tree-line, pitching a tent while being pelted with hail, or putting on sweat-soaked underwear in the morning for the 50th time, it becomes far too easy to lose sight of your purpose.  Most thru-hikers do.  And as it turns out, the same is the case for entrepreneurs.

Entrepreneurial Trials

The steeper the climb, the more important finding this purpose becomes.  A half year backpacking trip is a pretty audacious challenge.  Starting a business in many ways is an even greater challenge, as there is no guaranteed finish line.  Your hail storms can persist years, and may never let up.  Ask any entrepreneur who’s failed to raise a round of funding, lost a pivotal member of their team, been hit with an unforeseen lawsuit, had a product launch that’s fallen far short of expectations, etc.  I guarantee “why am I doing this?” has crossed through their minds at least once, and likely often.

Those who rebound with full strength (or even come back stronger) are those who have a compelling answer, whether they’re consciously aware of it or not.  Their fork in the road likely presents similar destinations. They live with purpose.

Find Your Purpose

Why are you doing this again?  The question will present itself whether you’re equipped with an answer or not.  Early in the game it might be easy to recall, but after repeated blows, it becomes increasingly easier to forget.  Let’s not leave anything to chance.

Take at least twenty minutes to consider all of the reasons you’re starting your own business. Ask yourself the same three questions and write your answers down:

  1. Why are you doing this?  Focus on your current state of affairs.  Maybe your current job doesn’t challenge you. Perhaps not pursuing your passion brings about greater pain than the idea of venturing into the unknown.  Maybe it’s mission specific – you feel compelled to build the world’s best marketplace for (service/product X).
  2. What benefits will you get from following through? Include as many reasons as possible.  There’s something not satisfying about your current way of life, how will starting up change that?  When you look in the mirror, what person will you see?  How will you benefit financially?  How will it effect your career?  Your family?  Your friends?  Go deep.
  3. How will I feel about myself if I quit?  Similarly how will you feel if you throw in the towel after six months or a year of lackluster traction?  How will you feel having to tell your family and friends that you couldn’t cut it?  

I encourage you to really dig deep when asking these questions.  Let your emotions run wild.  Focus on being too thorough without fearing redundancy.  It’s important to uncover your most compelling reasons before getting into the thick of it – at the height of your conviction.  This snapshot will serve as startup fuel when others’ tanks are running dry.

Purpose = Profit?

I’m not crazy enough to claim that knowing your purpose is a guarantee to a profitable future.  There’s a lot that goes into a startup’s success.  Purpose, however, will allow you to stay in the game long enough to make good on your passion when those without direction will be more likely to throw in the towel.

I have not failed.  I’ve just found 10,000 ways that won’t work.”  – Thomas Edison

If you want more behind the psychology of taking on a monumental challenge, check out my book Appalachian Trials: A Psychological and Emotional Guide to Thru-Hiking the Appalachian Trail.


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When Zach Davis isn't getting lost in the mountains, he is hustling from Boulder, CO as Tech Cocktail's Director of Marketing. He is the author of Appalachian Trials, a book chronicling the mindset necessary for thru-hiking all 2,181 miles of the Appalachian Trail, a feat he accomplished in 2011. Zach is a green tea enthusiast, die-hard Chicago sports fan, and avid concert-goer. Follow Zach on Twitter: @zrdavis.

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