I can’t tell you the exact point in time when I knew I wanted to sail around the world…

But I can tell you that for my whole life, I’ve had a yearning to be free.

And sailing your own vessel around the world’s oceans always seemed like the epitome of freedom to me.

Growing up under the thumb of an oppressive U.K. educational system in the 1970s – and being forced into my first group home at the age of 8 and foster care at 13 – impressed upon me the vital need for self-determination and self-sufficiency…

In short, freedom… But freedom isn’t free.

You have to fight for it. You have to earn it.

And even when you think you’ve won it, you can wake up realizing you’ve placed yourself into a different type of bondage.

That’s what happened to me after 15 years on Wall Street.

Sure, Wall Street gave me money, skills, and connections… But it also gave me a desire for material possessions without reason to obtain them other than “wanting” more.

I put “wanting” in quotes because I don’t know if I knew what I wanted at all.

Wall Street turned me into a rat in a maze… addicted to the cheese at the end of the puzzle but never thinking whether I was still hungry or not.

If the cheese was there for the taking, it was my duty to get it. Or so I thought.

And so I found myself trapped in another form of imprisonment outside of what I had consciously chosen for myself.

So today, getting clear on what I want – and why I really want something – is a constant iterative process for me.

I ask myself, “Do I really want this? Why do I want this? What do I hope this will bring?”

When I ask those questions now, my answers differ from those I had 10, 20, 30, and 40 years ago.

At the end of the day, I now consciously realize I want my life to have meaning. I want my life to matter.

Chasing Freedom

On a parallel track with that, I want to be the one who makes the decisions on where my life goes.

I don’t want to depend on any human, government, job, or business. That kind of freedom either takes a lot of money or the ability to live a very simple life.

And I’ll admit to you now, the trappings of wealth still ensnare me…

I love staying at 5-star hotels. Eating at Michelin-star restaurants is a thrill for me. And I thoroughly enjoy flying on private jets.

It’s tough to admit, but flying first class feels like I’m slumming it.

(I know, I know… Boo-hoo, what an entitled SOB I must be…)

I didn’t say it was rational, and I’ve never claimed to be perfect, but that’s the truth of it right now.

As I’ve gotten older, I think real freedom is a combination of things…

  • It’s the ability to feel gratitude no matter your circumstances.

  • To consciously choose your own opinions and beliefs regardless of their popularity.

  • And the ability to pick the path you want to follow in life no matter what the world may think of you.

The good news is that type of inner freedom doesn’t require a penny in spending.

I know I’m not there yet… I’m still clinging to the idea I’ll find all that while sailing the world on a $2 million boat.

But while I may not find all I’m seeking from this current adventure, I won’t let that stop me from trying.

The Finnish Word I Live By

Sailing my boat around the world is something I have to get out of my system.

As I write this, I’m lying on my bed on my boat while moored in one of the Canary Islands called Lanzarote.

In a few days, my captain and I will take Sisu, my red-hulled 50-foot Privilege 510 Signature Catamaran, across the Atlantic and into the Caribbean.


Sisu, Teeka’s catamaran

(“Sisu” is a Finnish word that loosely translates to mean “grit.” But even that doesn’t do the word justice. To have “sisu” is to have an inner fire that pushes you forward despite overwhelming obstacles.)

Our first stop will be in Barbados. It’s a 3,000-plus-nautical-mile sail that will take the better part of 20 days to accomplish.

So the deal I’ve made to myself is this:

If you still want to chase this dream of sailing around the world after 20-plus days at sea, go for it.

But if you find yourself kissing the ground of Barbados when you arrive, then just enjoy cruising the Caribbean… Sell the boat at the end of the season… And chalk up the whole episode up to a scratch well and truly itched.

Permitting yourself to try something that may not work and talking about it publicly is another type of freedom.

So to hell with the naysayers… This is your life… Go live the life you want.

Let The Game Come To You!

Big T

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