In a few days, I’ll be traveling to Wisconsin to tell my family about my plans to travel the world. I may be 45, but I’m still going into the trip with a fair amount of trepidation. Since they’re not big travelers, I’m anticipating some interesting discussions.

To facilitate the announcement, I agonized over a nice letter that summarizes my plans and thoughts. Eventually I came up with this:

Dear family,

I’m leaving my job and everything I own to travel the world.

Hugs and kisses, Joel

image credit: Foxtongue via Flickr

I’m hoping that really kind of says it all and we’ll just go back to playing cards with the dulcet tones of Shep Smith and Fox News in the background.

In case it’s not enough, I’ve put together a little list of the questions I figure might come up.

Are you fucking crazy? Why are you doing this?

I’ve never really had a “bucket list.” My general lack of impulse control means that when I decided I wanted to do something, I just went out and did it. That’s led to some fantastic adventures – cycling through Italy, a triathlon in Malibu, seeing the running of the bulls in Pamplona, dancing in the Carnaval parade in Rio and lots of other wonderful experiences.

There is one thing I’ve had on my list for over 12 years now and that’s to travel the world. Not one country or city at a time during extremely limited vacations but to see as much of the world as possible in an in-depth way. The concept of a “gap year” in which you travel the world is common in many places, but unheard of in the United States.

My dream is to spend a month or more in every country I can, exploring the small towns, the culture, the food and the people. If I can stretch this trip out to 10 years (and still enjoy it), I will.

Did you win the lottery?

Hardly. Between my constant gadget obsession and a lifestyle that had me blowing money throughout my 30s (see: Ways to Save Thousands) I only started saving in the last 3 or 4 years. Originally, I was socking away cash to purchase a house but I could never commit to buying. My heart just wasn’t in it, no matter how many people told me what a “good investment” it was. It wasn’t MY dream.

Then how can you afford to do this?

The thought of this will make some of my friends cringe, but I won’t be staying at the Four Seasons or Burj Dubai and then moving on to the Fullerton in Singapore. I’ll be getting along inexpensively, at costs significantly lower than my daily life in Los Angeles. Settling into small towns by renting a room for a month at a time is far cheaper than the rents and expenses I’m used to, even with a shitty exchange rate. Cycling from place to place means my transportation bill is little more than a big plate of pasta.

I’m also lucky to have made wonderful friends in several places around the world – in England, Thailand, Portugal, Greece and elsewhere. If I can stop and enjoy time with them for a while (without putting them out), all the better.

What will you do for money?

Anything that makes sense. I’ve always wanted to write, and while making a living writing about travel is something only a select few can really do, there are other niches that need some love. While I travel I’m open to adventure, even if it’s a unique experience at a short term job. Whenever I can pick up a few bucks and do something interesting for a while, I’ll jump at the chance. Hell, I’ll eat a bug on a dare if it makes me 20 quid.

How can you leave a stable job?

In Southern California, we don’t have leaves that change color, so Autumn is the season when jobs die and fall off the trees. At a lot of companies, lay-offs happen every year in October or November. Whether for financial reasons in a bad year or a corporate re-org in a good one, people lose their jobs all the time. That constant state of fear was a wake-up call that no position is certain and you are the only one who controls your own destiny.

What will you do when you get back?

I have no clue, but I have a couple of years to figure it out. It’s unlikely that I will attempt to pick up where I left off. My hope is that travel will open my mind up to new possibilities for the next stage of my life.

The guy made a million dollars!!

A big part of my career success has been developing new businesses where they didn’t exist before. Along the way, I scrawled down dozens of ideas I thought would be interesting to pursue as small business opportunities – online or otherwise. Having a year on the road will allow me to sort through some of those ideas and see if any of them actually make sense.

Isn’t all this very loose and largely unplanned?

Yes, by design. I’m embracing the unknown. Because the known is kinda dull.

More Q & A to come…

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