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This post was written enroute to Skip Winter Conference — A little conference that almost didn’t happen. (I’ll write about that in a few days).

I write this as I sit on the plane, enroute to join 10 close friends in Mexico.

The sound of laughter is resonating from the seats in front of me.

My friends Jenny Blake and Allie Mahler are giggling about something in a magazine.

I assume the magazine is Cosmo, but it very well could have been the economist. Those two are smart cookies. ;)

As I gaze through the small slot between their seats — it hits me — this is what life is about.

Right then and there, somewhere over the Atlantic Ocean I was able to see what is truly important in life.

Stunned, I start typing in an effort to record the thoughts that were flying through my head.

I created a simple document to jot down the key elements I had just identified that were special about that moment.

Here is the list:

The Most Important Things in Life

  • Deep Connections with Family and Friends
  • Unique Experiences
  • Continuous Growth
  • Leaving a Legacy

The Keys to Happiness

Cliff Jumping during the 'Chasing Happiness' years.

Upon creating this list, I sat for a moment and realized that this list is similar to something I had created in college.

Immediately, I begin to sift through my ancient documents and stumble upon my original list titled “Keys to Happiness.”

I quickly opened the document and instantly I am taken back to the blue glow of my college computer and my “ramen profitable” dinner of two PB&J’s and a protein shake.

During this time, I remember being immensely unhappy and I wanted that to change… badly.

I as I wrote the first list, I promised myself that from there on out, I would only focus on what made me happy.

Not money, not fame, not what other people wanted, but happiness.

I remember feeling like it was time for a reinvention… and it was.

The following years after writing the initial list where just that… a massive reinvention or series of reinventions that brought me to where I am today.

I call those years the “Chasing Happiness” years and will probably write about them at some point.

(The photo above is from those years. The idea of “Cliff Jumping” means a lot to me both figuratively and metaphorically and it’s cool to have a picture of me jumping off one of my highest cliffs ever.)

What’s Changed: A Focus on Legacy

With the hum of the jet engine roaring over my headphones, I compared my newly written list with the original list.

I quickly realized all of the key elements were exactly the same except the last one.

“Leaving a Legacy”

Shocked, I reread this line over and over as I reflected on all that had happened since college.

As I sit here over 30,000 feet in the air, I am left with the scary feeling that a BIG change is on it’s way.

There may be some turbulence and some times of doubt but deep down I think a shift has happened.

Just as the years after the first list where focused on happiness, I can see that the years to come will be focused on the important things in life such as legacy.

#0F

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A few weeks go I got a text from my friend Nik at 6pm that read “Do you wanna go to St Maartin tomorrow morning?”

My immediate answer was something to the effect of “No Way”

Less than 24 hours later we had hopped on a private jet down to a private villa in the Caribbean.

Our crew of 6 consisted of people from all walks of life but each of us had “jobs” that allowed us the flexibility to travel spontaniously.

This trip really reminded me of the reason I work so hard to keep my overhead low and my flexibility unlimited.

It also wouldn’t have been possible without tools like, Tripit, VRBO, Skype, and Hipmunk.

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Entrepreneurship and College – Is Dropping Out the Right Choice?

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Just recently, I was invited to the White House to speak with college students and aspiring entrepreneurs on the importance of mentoring. The event was hosted by MTV, the Obama Administration and the Young Entrepreneur Council (which I am apart of.) At the event there were a few students who were debating about dropping out [...]

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How To Get Started in Affiliate Marketing

Affiliate Marketing 6 comments

“How do I get started in Affiliate Marketing?” This is one of the most common questions I get asked and my answer is always the same: Learn the basics of mutual value,  create a unique strategy, and sell a product that benefits your customer. At a fundamental level this is all there really all there is to it… …but [...]

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Sean Power's Laptop and the Girl in the Purple Sarong (Day 4 in NYC)

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So tonight was interesting to say the least, after making it home from a party for Jenny Blake’s new book, I was hanging out with Lewis Howes. We decided to go meet a few people down in SoHo. After 5 minutes of looking for a cab (it was brisk) we decided to catch the train. We walked [...]

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Audible Review – Free Audio Book Inside

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I started using Audible in March 2006. Since then I have listened to over 90 audiobooks ranging from self development classics such as “Rich Dad Poor Dad” to fiction novels from the “Enders Game” series. Much like Amazon changed the way people purchased books, Audible is changing the way people “read” books. Over the years [...]

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Decisions Define You

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It is the opportunities you don’t take that define you and your career. Marvin Acuna shared this adage with me and for some reason it stuck. If you are someone who is actually up to something, something big, you will be exposed to more opportunities than you are going to be able to pursue. It [...]

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Interview with Willie Jackson

Becoming Bold 7 comments

Willie Jackson is a true rising star. Willie exploded onto the WordPress scene in 2010 after leaving his comfortable corporate job. Willie is now working on the Domino Project with Seth Godin which seeks to revolutionize the publishing industry. I see nothing but big things in Willie’s future so I was extremely excited to interview [...]

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The Passion To Do Things Others Only Talk About

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This post is a particularly personal post. Just this past week, in the rush of packing for our 2 month trip to Central & South America and wrapping up an awesome project. My grandfather passed away. My Grandfather had battled a brain aneurysm vigilantly for 6 months when it was finally his time to go. It is [...]

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Interview with Steven Place

Becoming Bold 1 comment

Today’s interview is with Steven Place. Steven is driving force behind the very successful Investing with Options. If you have ever thought about learning options, Steven is the man to follow.

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