Freedom Skate Day 7: Your most Interesting Day

Sept. 12th, 2010

It rained today… All day. It wasn’t a very exciting day, but I had one moment of sheer bliss! I was thinking about the trip up until this point, when it dawned on me: My life is marvelously ridiculous! Just one month ago, I was dutifully serving tables at a local restaurant back home. I was also busy getting ready for this journey, but it was mostly predictable and reasonably normal. Since then, I have done the following (with help of course):

1. negotiated a business deal with my investor, APV, for start-up funds that would ultimately be greater than the entire sum of money that I made while serving tables between the months of February and August (just enough to get started with this skate 🙂 )
2. purchased a 1989 motor home (with random subwoofer pre-installed), and proceeded to have the sides plastered with Freedom Skater images.
3. drove said motor home through the streets of New York City and literally camped out on the corner of 2nd Avenue and 81st street for two nights.
4. skated with Dillon and the investor right down 5th Avenue, as if driving a vehicle.
5. arranged for interviews with multiple high level entrepreneurs and one minor celebrity for the documentary.
6. was scheduled for a talk at Yale, and my awesome helpers are working on setting up three to four more talks at other Ivy League Schools.
7. co-founded an innovative company that might just change the way start-ups are born (details coming as soon as it’s public knowledge)
8. met and worked with more amazing people than I can list here.
9. felt completely out of control and out of sorts the entire time!

Shouldn’t your life be interesting?

I tell you all of this not to brag but to make a point: Great opportunities come when we have the courage to do things that are “too big.” None of the opportunities listed above would have even existed had I not made a choice to do something crazy and skate across the country just a little over three months ago. These things also would not have happened, if I had not kept my mind open to crazy and impossible new ideas. The fact that I felt out of control the entire time is a symptom of great change. My feathers were rustled, because my life was changing faster than my mental state could keep up with. It was challenging, it was intense, but most of all, it was interesting and exciting.

In his absurdly popular book, The Four Hour Work Week, Tim Ferriss makes an interesting distinction: He claims that the opposite of happiness is not sadness. In fact the difference between these two emotions can be difficult to discern sometimes. Instead, the opposite of happiness is boredom! It makes sense really, and I tend to agree. Most of our miserable days do not come as a result of some tragic occurrence; rather, they come because we are discontented with the level of fulfillment we get out of life. It has no spark. Wouldn’t it be amazing if you could wake-up every morning with a buzz and energy running through your veins? And no I don’t mean a caffeine buzz. The truth is you can, but the only way to make it happen is to spice things up a bit! If you always play it safe and never put yourself out there enough to explore new possibilities, most of your life will be spent in dreary days that you will scarcely remember. Your choice to play it safe so often will ultimately prove to be the bigger risk, because you will miss out on so much of what life has to offer.

I want to challenge you to make your life interesting. If you’re not chicken, I dare you to try this:

Pick a day within the next week which shall be “the most interesting day of your year thus far.” Your assignment on that day is to mix things up enough to ensure that you get to the end of the day thinking, “What the hell just happened?” I want you to be lying in your bed laughing about the manic hysteria that was your day. You don’t need to choose to skate across America. You don’t even need to plan it out. All you need is that attitude, and every time you get tempted to play it safe and stick to routine, just remember your mission. You might just find that the experiences of that day alone will be the inspiration for some choices that will alter the course of your life forever. I make no promises or guarantees other than this: You will have an interesting day, and you won’t be bored.

Don’t come back to this blog until you have completed your homework assignment and picked a day. And don’t you dare pick a day and only give it a half effort. I may not know, but you will! I want your stories in the comment section below.

BTW: Here’s a fun little video from my skate yesterday: (It’s taking forever to upload. It’ll be posted early in the day Monday… It’s late, and I’m tired.) 🙂