Skate across America Day 17: Entrepreneurship Leads to Freedom

Oct. 20, 2010



Total Distance for today: approx. 35 miles
Total Distance for Trip: approx. 233 miles
Current Location: Baltimore, MD


Today’s skate from Darlington, MD to Baltimore was by far the most challenging skate of the tour to date. It wasn’t so much that I skated 35 miles as opposed to the more typical 20-25. It was THE HILLS! It turns out that skating up a couple hundred feet and coming back down the same distance does not require the same amount of overall energy as just skating on a flat surface. For one, I’m not skating on space-age near frictionless skates, so most of the momentum gained while going down a hill is lost quite rapidly. Also, I don’t know what it is, but skating up a hill is far more difficult than walking or running up it. You just cannot move with proper skating dynamics (as if I’m some professional skater who always skates with perfect dynamics!). I would compare it to running uphill… in sand! Whaah! Whaah! Listen to this whining! It wasn’t that bad, and I made it just fine. The truth is: The hills are important right now for me to build the kind of stamina and leg strength I will need to carry me through the long hall.

Envisioning Freedom

I have lots of time to think while skating, and lately, I’ve been thinking about a major challenge associated with this tour: connecting the concepts of entrepreneurship and freedom for my fans. People don’t always see it. Before I can really explain that connection, it is necessary to decide exactly what freedom is. Many believe that freedom is the ability to do whatever you want whenever you want, to have no responsibility, and to basically not have a care in the world. I’ve been there, trust me, but I think this is a shallow understanding of freedom. I’m about to show you why it might actually be a form of slavery! How so? The type of zero-responsibility and zero commitment freedom I described can be fun for a while. I’ve experienced moments in my life when I didn’t seem to have a care in the world, other than having fun in the moment. That happened a little when I studied abroad for a semester in Europe. While it was definitely a growing experience that I still grow nostalgic about to this day, it lacked a certain depth that I am working toward now.


Here’s the problem I’m getting at: When we only care about feeling good in the moment, we become slaves to our emotions and to the external events that can change on a whim, without us having anything to say about it. Our freedom is not true freedom because it is dependent on the perfect alignment of external factors. The moment anything gets knocked out of whack, suddenly we are miserable and what seemed like an awesome life can start to feel pretty ugly. Do you see the problem here? Freedom that is based simply on feeling good in the moment lacks the depth that it needs to stay anchored when life throws you a curveball. It has no character!


What is freedom, if it’s not just a feeling of complete bliss in the moment? Might I suggest that freedom is what we experience when we are pursuing a life that is built around the thing or things that we are most passionate about? There’s a certain liberty that can only be found in passionate pursuit of our deepest desires; even when we have setbacks, we can still continue to face toward the direction we are trying to move. Sometimes we move closer, sometimes we fall back, and sometimes we don’t move at all, but we are always facing that direction. Such certainty provides us with a depth that is not to be found in a life lived simply for the bliss of the moment, because we actually know what we want!


There is nothing more liberating than a complete knowledge of what you want! Repeat that to yourself, because it might just be one of the most important ideas you will ever encounter. When you know what you want, without question, most of life’s nagging questions begin to fade away, because you’ve settled. You can move in your direction, even if you must step on some toes and break some “rules” to get there. The sureness of action that defines a person who has decided on a certain course is undeniable, and things seem to fall in place before him or her! Have you ever met someone who just seemed so dead-set on something that you knew nothing in the entire world could possibly prevent her from achieving it? Shouldn’t you strive for such clarity of vision and purpose in your own life?

Connect the Dots: Entrepreneurship as a Path to Freedom

The title “Entrepreneur” may not conjure up the same image in your mind as it does in mine. For me, an entrepreneur is someone who has a clear vision for their life and is passionately building a business around that vision. As we’ve already established, the person who has a clear vision, sets a clear course, and walks in that course is the most free person, and entrepreneurs who build businesses around their passions are those kind of people! That is freedom: To be passionately pursuing the things that matter most to you and creating the world you desire around yourself.


While not everyone is cutout to be an entrepreneur, the bold, independent, and creative mindset of the entrepreneur is becoming more and more essential in modern society. The old “robot” jobs that so many of us have been “trained” for are no longer available. In an increasing number of cases, they are being outsourced, automated, or eliminated entirely. “Work” is not as clearly defined as it was in the generic “Information Age.” As we move into the Creative Age, progressive employers are beginning to look for self-driven and creative people who can think independently. Nobody wants to hire someone who asks, “What should I do now?” Everyone wants to hire someone who says, “Look what I’ve done now!” This is intrapreneurship, and it’s such a revolutionary idea that my spell-check doesn’t even recognize the word! Maybe you don’t want to be a full-fledged entrepreneur, but you better start thinking like one! The future belongs to people who are bold, passionate, creative, and independent in thought. The future belongs to people who are free!


Note: If you are enjoying these posts, please do pass them on! You can help me spread this message of freedom to an entire nation! And don’t forget to subscribe (right side of website) and receive notifications of the new posts by email, if you haven’t already!

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