Jeff Keen

Making future plans is an effort for me usually, and I can often get wrapped in the days so much that I miss the weeks and months flying by.

Since I quit the 9-5 thing and started playing the self-employment game I’ve been able to work from anywhere, but for a while I didn’t really take advantage of it like I wanted to. So somewhere around the beginning of this year I decided to try and travel somewhere every month in 2016.

A modest goal. And it’s a goal I stuck to.

In January I was in San Francisco to visit my friend Stephen, and then we went to Tahoe to go skiing. Also went camping in Colorado bend State park.

In February I went to New Orleans for a bachelor party, and I was in Houston at a client onsite meeting for a week.

In March I was in Portland for a conference and for fun.

In April I had a magical long weekend in New York City.

In May I had no plans and the month slipped right by. And then on the 28th, realizing if I didn’t act fast I would have failed, I looked for last minute flights to anywhere to keep up this goal. Flights to Denver are always cheap, so I called up my friend Knox to see if he was available.

“I love how stressed out you're getting over this arbitrary goal you set.” —Knox Lively

He was available. So I went to Colorado, talked to some strangers, made last minute plans to visit some family friends in Fort Collins, stayed with Knox in Boulder, and got a lot of work done. Overall I had a fantastic time and had it not been for the arbitrary restriction I might have never pulled the trigger on that trip.

Moral: constraints are good.

For June, I chose Montreal. Cooler weather to escape from this Texas heat, some Bagels I wanted to try, bikes, and it came highly recommended. Bonus: getting out of town for 4th of July weekend. Solid. Booked the flight and even worked in an overnight in Philly to see some things there because I’m crazy. Booked the hotel, found the places I wanted to visit, bought a guidebook, researched international data plans, and had my bag packed a full 24 hours before my 5:50am flight time (tomorrow, as of this writing).

But I just canceled all of it because I have a ridiculous sinus/ear infection. I went to my doctor today to get the standard run of antibiotics (the worst/best), and she advised that I don’t fly unless I want to burst an eardrum¹. I’m not risking ear damage, so I called it off.

But now what? Two days left in June, trip canceled, can’t fly, and feel pretty crappy right now. What’s happening to this travel goal? Who is judging this at the end of the year? What are the rules?

So far the only “rules” I determined just made the goal harder:

1. An overnight stay is required to count it as a trip.
2. A single trip cannot count for two months. I was in Portland from the end of March to the beginning of April, but that doesn’t check the March and April box.
3. No repeat cities within a calendar year.

My brother added the last one and it might have to change because I want to go back to New York, and I want to go back to San Francisco. In the current rules I could do that, but it wouldn’t count as a trip. Writing this out makes me realize how bullshit (and expensive) that rule is.

Also, I’m a little unclear on how multiple cities in one trip (San Francisco and Tahoe, Denver and Boulder), and multiple trips in one month (New Orleans and Houston) count towards the overall goal. Can I pay it forward? With eight cities so far and it only being June, can just stay home during Austin’s worst months knowing that June, July, and August have their travel box checked?

Who’s defining this box? It’s me. Do I own the box? Yes. Can I change the box if I want? Sure.

So maybe I’ll take June off. Or… maybe I’ll go check out San Antonio² on the 30th.