What Athletic Challenges can Teach Us about Entrepreneurship

The Dolphins Cancer Challenge, is a 180 mile bike ride to raise money and awareness for cancer research here in South Florida, that I participated in this past year.  Having barely trained, prior to the event, the ride was going to be challenging to say the least.  But as imperfect as things were, I just had to start.


It was a day of contrasts, in the morning there were 1000s of riders, police waving us through red lights, cheering crowds. The second half of the day was tiny groups of 5 to 10 riders, fending for themselves, against a 20mph headwinds and a sea of angry motorists through the streets of Miami and Fort Lauderdale, no cheering crowds, no police escorts. I fell exhausted into bed at 7pm, wondering how and even IF I was going to ride the next day.



Waking at 2am with blinding headache from dehydration, I lay there until dawn wondering if I should ride. Every excuse came to mind, exhaustion, dehydration, wicked headache, significant pain. There was no penalty for not finishing, no one would even know, they weren’t checking us in for goodness sake! I had already ridden half of it, wasn’t that enough? A little voice in my head said NO, that’s not enough! You made a commitment, finish it! So I got back on my bike, (second day is always the worst, hate that saddle) and rode back to Dolphins Stadium.

So what does all this have to do with being an entrepreneur? I made some observations along the way.

Just Start and you will figure it out

I felt unprepared for this ride; we often feel unprepared to start a business.  We need to read more, train more, watch one more webinar, consult one more expert.  While education/training are important, you do eventually have to “get on the bike”. So this is my first blog post, I have been thinking, planning, wondering what to write about, wondering who to write for – enough is enough.  There is power in action – it feels so great to just start!

You make the difference

You may never know the impact your message, your smile, your kind gesture, your blog post, your comment. My first big weekend ride was the Pan Mass Challenge (that has raised a staggering half a $billion for cancer research and care).  I had the flu, fever, cough, aches, the whole bit. I was riding alone for the most part, doing everything I could to just reach the next water stop, (actually feeling pretty sorry for myself, which is amazing considering who I was riding for!)  At the final stop with 25 miles to go, I nearly gave up.  A happy, healthy 12 year old girl was standing with a picture of her younger self, bald and scared obviously during her cancer treatment.  The sign read “I’m alive because you ride – You make the difference!” The effect was profound.  I wish I could find that girl and tell her what a difference she made in my day, in my life.  She literally carried me across the finish line that day, and she has many times since.


Real commitments are the ones we make to ourselves – these are the most important. As entrepreneurs there is no one to answer to, no one “check you in” we have to answer to ourselves. There is no finish line, no performance review, no one measuring your failure or success.  It’s just you; just you and your promise to yourself.


When riding with more experienced riders, or working with more experienced people, we often look to others to provide leadership.   This weekend I was often at the front, pulling our little group home.  As we rode past a struggling rider, my husband yelled “jump on the back, momma duck is leading us ducklings home”.  You don’t have to be a leader of the whole world, you can be a leader in a tiny group;  build your skills, help a larger group; build more, help more.

Looking for the best in people, brings out the best in people

For a time this weekend, I rode with a woman, who was steady, consistent and gave lots of notice if she was changing pace or direction.  I complimented her on her riding style, she smiled and thanked me.  And you know what, she sat a little straighter, tried even harder to be the best she could be.  By contrast when experienced riders blow by yelling “Hold your line” (i.e. don’t wobble or swerve) or critiquing style, it creates animosity, embarrassment and leaves both parties diminished.  Focus on peoples strengths.

Laser focus on a goal is the key to success

I was laser focused on Dolphins stadium, I had one goal, and I was getting there if I had to crawl.  And strangely that focus made it so much easier.  In business there are so many distractions, so many claims on our time, it is easy to lose focus.  If you write your big goals down, commit to them, focus on the end result.  Don’t worry too much about seeing all the steps along the way, and just “ride to the next water stop” .  As the indomitable Les Brown says “You have greatness within you!”.

Caro Doughty Small





email: Caroline@carolinedoughty.com

Skype: carolinedoughty

PS. Download my free book, “How to Make People Fall in Love with Your Brand”  at carolinedoughty.com

Please note: I reserve the right to delete comments that are offensive or off-topic.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

14 thoughts on “What Athletic Challenges can Teach Us about Entrepreneurship

    • Thank you Jacqueline, that is one of my favorite phrases – how many lines came out of Jerry MaQuire?

  1. Caroline! Thank you for your beautifully honest and inspiring post. I’m glad to know you and be on your list. I’m smiling thinking of the girl holding up the sign :O)

    • I wish I could find the photo of that girl, I can still see her. Its true she does carry me across the finish line often 🙂

  2. What an inspiring story you’ve told here, Caroline! Thank you for sharing your trials and your successes. I particularly appreciate your insight on leadership – “I realized, you don’t have to be a leader of the whole world, you can be a leader in a tiny group; build your skills, help a larger group; build more, help more.” And thank you for the reminder: “I realized the real commitment was the one I had made to myself – that’s the most important.”

    • Thank you Kristin, it was a great ride for a great cause. I am so honored to be able to do this, and to meet the amazing people along the way.