A Month of Travel, A Year of Adventure

During the first few days of that change in my life that I like to call The Great Reset, one of the decisions I made was to re-incorporate travel into my life. My then-boss John Oxley understood what I was going through and was only too happy to oblige when I came into his office and said “Put me on the road, man. Put me on hardcore.” He did, and in the first three months of 2011, I travelled far and wide on Microsoft’s behalf (as well as their dime), going to Montreal, Austin and Vegas, as well as Seattle twice in a month.

Between the Great Reset and a couple of personal discoveries made during the two Seattle trips (which includes a long night of the soul, where I took advantage of the hotel’s “three chicken tacos and three Coronas in a bucket of ice for 20 bucks” room service special and stared at the highway to Portland), I decided that I needed the big life-reset needed to be complemented by a big job-reset. A very lucky break landed me a job at Shopify, and with it came even more travel. Between all the flying about (see this entry for a partial list of my trips) and spending the summer doing Shopify immersion in Ottawa, 50% of my time was spent on the road. Hence my current catchphrase, “Home is a nice place to visit.”

This week marks the beginning of a month of travel. Here are my destinations…

Montreal (Tuesday, February 28th – Saturday, March 3rd)

My last jam session at the Montreal metro, back in 2009. The story is here.

I’ll be going to Montreal attend ConFoo, a “web techno conference”. I’ll be there to represent Shopify as well as to give a presentation on the Ruby programming language titled Ruby as She is Spoke (Thursday, March 1st at 11:00 am). I’ll also be there to provide moral support for my coworker David Underwood, who’ll be giving the Mo’ Money, Less Problems with ActiveMerchant talk (Friday, March 2nd at 8:30 a.m.). I have every intention of enjoying the city’s wonderful night life while I’m there, but I’ll be back in Toronto on the afternoon of Saturday, March 3rd to catch up with local friends.

Austin (Thursday, March 8th – Wednesday, March 14th)

Having a great time on some bar patio at last year’s SxSW. Photo by Kris Krug.

After a short stay in Accordion City will come a fortnight of warm weather. For the first week, I’ll be in Austin to attend the South by Southwest Interactive conference! This will be my third; I attended my first in 2008 as an employee of b5media, my second in 2011 as an employee of Microsoft and now I’m going as an employee of Shopify.

If you’d like to know what hijinks I got up to during SxSW 2008 and 2011, see this entry.

This will also be my first time as a speaker. I’ll be on a panel titled 5 Brands Travel the US Inspiring Entrepreneurship, where I, along with my fellow members of the BarCamp Tour, will talk about our experiences and lessons from last year, when we crossed the country as very active and participatory sponsors of BarCamps in several cities. This presentation will take place on the Sunday, March 11th, but at least it will happen at a hangover-friendly time slot: 3:30 – 4:30 p.m..

This trip will have one more first: my first time making use of AirBnB. My coworker Edward Ocampo-Gooding and I will be staying at a really nice apartment just down the river from the Austin Convention Center, and the owner of the place has been especially nice to deal with.

Tampa (Wednesday, March 14th – Wednesday, March 21st)

I still haven’t blogged about the evening we went to Tampa’s big goth bar!

You see, there’s this girl. There’s also St. Paddy’s Day, which happens to fall on a Saturday this year. Finally, there’s a party, and my presence is expected.  It’ll be work during the day, and definitely-not-work in the evenings.

Ottawa (Monday, March 26th – Saturday, April 1st)

Some of us Shopifolks: me, Harley Finkelstein and Brennan Loh,
hanging out at Shopify’s Toronto office last week.

I’ll be checking in at HQ this week. While my job at Shopify coupled with my “travel anywhere” bag o’ gear gives me extraordinary amounts of freedom to work just about anywhere, there’s still no substitute for face-to-face contact with the coworkers at the home office. Hence this trip to touch base with the Shopifolks. I’ll be back in Toronto for April Fools’ hilarity Saturday afternoon.

Pleased to Meet Me

A self-portrait I shot in the mirror of my room at the Queen Elizabeth hotel,
a few days into The Great Reset. The original blog entry is here.

“If you travel long enough and far enough,” the saying goes, “you will eventually meet yourself.” Over the past year, I’ve done just that, and while the self I’ve met could always stand some improvement, he’s turned out to be pretty cool. I’ve discovered that I can go pretty far with just a few essentials: a computer, a camera, an accordion and a change of clothes. I took more chances in the past year than I did in the previous five. I have had more heart-to-heart conversations in a Starbucks in the past year than I have in the previous ten. I lost 30 pounds. I learned just what I’m capable of when the limitations are few and I put my mind to it. I’ve surprised myself – in the good way.

And oh, the experiences! I’ve been perp-walked into a “we have to talk” meeting with a Microsoft CTO and faced down a non-date gone terribly, terribly wrong – in the same 48 hours. I’ve used my accordion to win a karaoke contest in Austin, lead a Bastille Day parade in New Orleans’ French Quarter and charm ladies in a few cities. I have written code, given presentations and frightened room service in hotel rooms, I have created documentation and signed my Shopify contract in bars and I have put together demos as well as a letter of resignation in airport lounges. I have ejected loose women from a Quonset hut where I was staying and have myself been ejected from a lake by action-seeking casino cops. I have snuggled with someone in the nicest and crappiest hotels I’ve stayed at in the past 12 months. I made many new friends and acquaintances. I met a girl.

I have not yet tired of travel. Last year was about getting back into the swing of it; this year is more like that phase of having a sports car where you say “Okay, I’m comfortable with the controls…now let’s see what this thing can really do.”. This should be an interesting month in an interesting year, and I hope to share a lot of it here on the Accordion Guy blog.