The Next Step: Live (in) the World.


While kayaking on the River, I determined that the seasons, the weather, the elements are not to be conquered. They absolutely cannot be. However, just the same as a beautiful woman shouldn’t be conquered, Nature should be embraced and harnessed – a life-giving entity that empowers.

I have lived outside for roughly 22 months over the course of my life. Some of that was in the Rockies, the desert, the Himalayas, a nature laboratory, on a river, and in a barn. I understand the Earth. I have avidly gardened for six growing seasons. I sink my fingers into dirt, grind through it, and feel the inspiring pulse of life. Knees planted in the ground, while holding onto the world – literally in my hands – gives me connection to my home. The Earth element: stubbornly unmovable without a greater, more arrogant force. Planted. Ever subtly changing. Firm. Determined. Self-aware. Multi-faced among various terrains.

I know, understand, and identify with the Earth.

I poetically and intimately interacted with water for a month. I understand Water. I feel it. I move with it. It’s powerful yet elusive. It’s changing and constant. Water is always flowing, but when it’s still it is more still than any other element. Its form can morph between solid, liquid, and gas. There’s a fluid, intensely powerful forward movement.

My soul understands Water profoundly.

What is air? A breath of newness? Constant movement? Multi-directional? These are merely anticipatory guesses. I can’t identify with her; I don’t understand her…. Yet.

I want to embrace Air. I want to soulfully, internally hold Air.

I don’t want to stop. I want to always be chasing. I want to dance my beauty with others’ beauty like Wind dances and combs her way down Earth’s ribs. I want to bring a storm to the Earth – something unstoppable and bigger than life. I want to give life.

I have alluded to a grand plan; here it is. I will embrace and harness Air.

All $32,000 of my student loans will be paid off by the end of 2016. Financial freedom from the shackles of debt will no longer be a limiting factor in my travel plans. My net worth will be exactly $0, not including the few assets that I have.

Here’s my life strategy:

I will give away or sell everything that does not give my life intimate joy (thank you Katie Warner for that incredible insight). I will work for a few more months, saving a few thousand dollars per month. I will buy a seaworthy sailboat. I will learn to sail. I will pack up my bicycle, dog, books, a few pairs of clothes. I will live on the Mississippi River, fine-tuning my sailing. I will utilize my bicycle to access the hundreds of cities up and down the River (St. Louis, Memphis, Vicksburg, Baton Rouge, NOLA, etc.) When I’m comfortable with my sailing ability, I will drift to the Gulf Coast, making my way down to the Keys of Florida. I will dabble in bigger water, fine-tuning my big water sailing. I will make my way to Cuba and the Caribbean. I will kick it there indefinitely. Then I will make my way to wherever the winds take me: Australia; or Brazil; or the Mediterranean Sea with access points to Spain, France, Algeria, Libya, Italy, the Holy Land, Turkey (a dream of mine), Egypt and the Nile River…who knows.

My favorite part of this life strategy is that I’m doing nothing different than what I’m doing now – I’m just adding a sailboat. “How so?” you ask. Good question. I bet you’re also wondering how I’ll make money. There’s the answer to the “How so”.

The only ways I’ve made money and spent 50-60 hours of my weeks in the past three years have been teaching, serving, bartending – all with a splash of entrepreneurial pursuit.

  1. I’ve taught English in Vietnam and two more years teaching Stateside – I am qualified to teach anywhere in the world.
  2. Where there are people, there is celebration and despair – there is alcohol and bartending. If I can bartend, I can bartend anywhere.
  3. The more traveling I do, the more stuff I can buy. Say I sail to Cuba. You can bet your ass that I’ll buy all the cigars I can get my hands on A) to smoke and B) to sell in Italy. Same with stamps (I met a man on Halong Bay who was making $3000/week buying and selling antique, international stamps), coins, trinkets, and other high-value cultural things.
    1. Imagine a man with a sweet set-up wearing a white-brimmed boater’s hat, a white button up, boat shoes, khaki shorts with a brown belt, and a beard with long red hair standing on Mass Ave – a hip, culturally sensitive, local hangout spot for many young professionals and wealthy business people. This man has many interesting things from Cuba and Italy and Egypt and Australia would you listen to his story of travels and bought goods? I certainly would. And I’d pay a lot of money for his story and things. As the seller of those goods and a story, it would be life-giving for me to tell my story and see them inspired and interested.

Do I know how to sail? No.

Can people sail? Yes. Have people sailed solo, trans-Atlantic trips? Yes. If other people can do it then it can be done by you or me too. It’s a matter of dwelling long enough in the Deconstruction phase to come up with a strategic and successful strategy for the Execution stage.

I don’t want to be normal. I don’t want to be crazy. Imagine these two places on opposite ends of the spectrum. I want to be on the side of normal, but in a position to push the “normal” bar closer to crazy. That’s traveling roadless; that’s a fringe lifestyle. It’s not unreasonable to travel. It’s not unreasonable to be off-road. It’s weird to travel without a road, but not quite crazy. It’s not weird to kayak; It’s not weird to boat on the Mississippi River. Kayaking on the Mississippi River is mingling two normal things, forcing the bar of “normal” closer to the “crazy” end, but not officially making it absurd.

Here I am, pushing that bar again. It’s not weird to sail – in fact it’s an aspiration of many people. It’s not weird to go to the ocean – in fact; it’s many people’s vacation. Traveling the ocean by way of sailboat – not normal, not weird…but it pushes the normality of sailboating closer to weird. I will be literally and figuratively traveling roadless.

I love this life strategy just the same as I loved my first love. It makes me giddy thinking about it – so much so that I’m spending 12 hours a day thinking about this. My favorite part about this? I learn and harness the power and beauty of Air, for better or for worse. For richer or poorer. In sickness and in health. Until death do us part. In storm and in calm. In beauty and in terror. In normality and in insanity.

Just as Air has no boundaries, nor will I. My neighborhood is the horizon; my neighbors are 7.5 billion people. I’m not bound by the walls of my bedroom or a tent or riverbanks. I’m bound only by the Wind. I’m free. I will live in the world.


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