Toronto-to-Tampa Road Trip, Day 1

day 1

Friday, March 7th: After delaying the trip a day to finish off some client work, it was time for me to make the move to Tampa. After dating a wonderful Tampa-based girl (some of you have met her) long-distance for the past two and a half years, one of us had to relocate. I had the flexibility, and hey, I was due for a little shake-up and change of scenery, anyway.

Since I am not a rock drummer, I figured that I should be employed while living with the girlfriend. Through my financially disastrous mobile tech consultancy, I’d been working in partnership with a Massachusetts-based mobile tech company called GSG. We got along so well that they offered me work where I’d actually get paid. I could even work out of a home office in Tampa!

The job description falls under one of the professions that lets Canadians work in the US under a NAFTA provision called “TN status”, and my work experience and schooling qualify me for that status for periods of up to 3 years. All I had to do was bring the necessary paperwork and pass the interview at the border.

Rhonda the Honda CR-V in Ottawa.

The car is king down here. Yes, there’s a lot of great cycling around here, but in most cases, you should be doing it on the sidewalk, which very few people use anyway. Yes, there’s public transit, and the less said about it, the better. Luckily for me, I’ve got Rhonda, a reliable, well-maintained 1998 Honda CR-V with barely 140,000km (87,000 miles) on her odometer. My plan was to load her with my stuff and drive her down to Florida. I treated her to a new timing belt, tires, spark plugs, and a full tune-up before the big trip. As a reward for her 16 faithful years of service (she’s old enough to drive herself!), I was giving her the Canadian dream: to spend her final years leading a relaxed life in Florida.

Rhonda saw her last snow on the morning of our departure:

car at start

Along for the ride was my friend and copilot for the journey, Eldon Brown:


I’ve known Eldon since 1989, when we were both engineering students at Crazy Go Nuts University. He’s done the Toronto-to-Florida run before, and he helped plan the route. I like his approach to road-tripping: if there aren’t any hard deadlines to meet, keep it down to under 600km (375 miles) a day, and go to a brewery, brew pub, or distillery and a nice restaurant at the end of each day. He’s got a lot of road miles under his belt, both of the two- and four-wheeled variety, he was ready to take the wheel whenever I needed a break, and he was also more than happy to shoot some pictures of whatever accordion hijinks ensued.

It was great having Eldon along for the trip. He knew which places to check out along the way and where to see something interesting. It was also good to have someone else to check the GPS, keep an eye on my stuff, take the wheel, and have a conversation with. Over the whole of our trip, there was maybe only an hour or two of dead air; we spent most of the time talking.

The border

Our first stop was the last stop before the border: the Peace Bridge Canadian Duty Free Store to use the bathroom, get some breakfast, and take a quick look around. As part of a Crown Royal promotion, they’d set up a throne, crown, and cape for people to pose in, and sadly, no one was taking them up on their offer. I’m not the type to pass up a photo-op like this, and having had more than my fair share of Crown myself, it was only proper that I should try them on for size:

I also had to have a farewell meal. I thought these were rather appropriate:


I have a NEXUS pass, so I usually breeze through the US/Canada border crossing. However, since Eldon wasn’t a NEXUS member and I wasn’t just visiting this time, I had to drive up to the regular lanes and tell them that I wanted to do an interview for TN status. After waiting a surprisingly short time, it was our turn at the booth:

cbp at peace bridge

The CBP (Customs and Border Protection) agent at the booth took our passports, directed us to park in the lot near the CBP office, and told us to be prepared to wait a while. “It’s spring break,” she said, “so there are a lot of vacationers ahead of you waiting to be cleared.”

us customs

All customs waiting rooms, whether American or not, have the same general vibe: a sense of impatience, coupled with boredom punctuated by worry. The room was like a model United Nations: packed with people from everywhere, with each waiting party being called by name and nationality. As we took our seats and settled in for a long wait, one particularly unhappy-looking guy was being escorted with all his luggage by three uniformed men into a separate glassed-in interview area.

For Canadians, the TN isn’t even a visa — it’s just a status under which you’re allowed to work in the States for a temporary period. The interview process is very subjective: as an applicant, it’s your job to convince the CBP officer that the position you’re taking fits one of the approved NAFTA professional job descriptions, that you qualify, and that you’re not going to contribute positively and not do any harm to the Land of the Free and the Home of the Brave. I brought printed copies of my job offer letter and resume, my diploma from Crazy Go Nuts University (still in its frame), and my university transcripts, which not only specify my degree program, but also make for hilarious reading.

I had three separate chat sessions in total with the CBP officer to whom I made my case. I understood that he was just doing his job, which wasn’t easy, since among other things, he had to assess my fitness for the position for which I was applying for TN status. Some of the job descriptions are very specific, such as “disaster relief insurance claims adjuster”, “apiculturist”, and “soil scientist”, while others are pretty broad: “management consultant”, “mathematician”, “engineer”, and the slot for which I was applying, “computer systems analyst”. The list of approved NAFTA professions covers a wide range of careers, and a CBP agent has to somehow determine in a single interview if the job you want to perform in the US fits the definition, and if your education and work background make you qualified to do said job.

Getting approved depends greatly on the interviewer you get, and possibly the mood that s/he’s in. That’s why I chose to do the interview at the Peace Bridge; if I got turned down, it was a 90-minute drive home to work on Plan B.

I spent a good chunk of my interview explaining my position and the sort of work I’d be doing, which involved:

  • Going over what GSG does, which at its essence, build software that helps businesses manage their mobile and landline phones as well as the expenses that go along with them.
  • Walking him through GSG’s site — without being allowed to look at his computer’s screen — and providing explanations when needed.
  • Explaining that GSG’s formal name, Global Sourcing Group, is a holdover from an old line of business and isn’t an outsourcing company.
  • Going over my role, which is working with partner companies like Enterprise Mobile, IBM, Pomeroy, and Stratix, helping their sales and sales engineering teams understand what they can do with the GSG cloud platform, and how they can tie in GSG’s offering with their own to serve their customers.
  • Making it clear that my primary role would not be as a programmer, which CBP agents have been told is not admissible under “computer systems analyst”. I used a construction analog: “Programmers are like welders: they work directly on building the thing. I’m more like an architect,” and his eyes immediately flashed recognition.
  • Defining terms that were unfamiliar to him: platform, cloud computing, mobile device management.
  • Explaining certain parts of my resume that seemed weird to him: “Technical evangelist? What’s that?”
  • Giving him GSG’s CEO’s mobile number, who he called and had a conversation involved enough that he pulled over his car rather than do handsfree.
  • Doing little things like going over my university transcript and counting the number of computer science-specific courses. I didn’t even know that number; it turns out that I have 20.
  • When he was checking why his phone was taking so long to charge, I gave him this “power user tip” which always blows laypeople away: “They charge faster on airplane mode/ You’ll miss any incoming calls, but you will get charged faster.”

In the end, he pulled out a small slip of paper, stamped it, and stapled it into my passport. It says that I’m approved to work in the US for GSG as a Partner Technical Analyst until March 10, 2016.

He’d seen the salary I’d be making in my offer letter and suggested “You know, you could probably ask for a little more.”

“I’ll be sure to tell them that an official working for the US government said that. Thanks!”

“You’ll just have to head on over to the cashier and pay the processing fee,” he said. “It’ll be fifty-six bucks.”

The real first leg of the trip

west of buffalo

We lucked out with good weather: relatively warm temperatures, considering the rather chilly winter we’ve been having, and clear, nearly cloudless skies. Satellite radio was providing the music, my new iPhone 5S on T-Mobile’s unlimited-everything was acting as our GPS, and Eldon was navigating. The plan was to make it to Morgantown, West Virginia by the end of the day.

dash highway view

mark dalton trucker detectiveThe next time you’re in a truck stop, go to their store and check out the CD selection. There are usually a good number of audiobooks on CD, and chances are you’ll find the Mark Dalton, Trucker/Detective series. Yeah, they’re pulp fiction, and you’ll see the plot “twists” coming from a mile away, but they’re great, non-distracting, driving entertainment that helps pass the time on the road. Eldon and I listened to the first two installments on the way down.

Here’s a quick taste of Mark Dalton, Trucker/Detective that I found on SoundCloud. It doesn’t capture the full Mark Dalton experience, but it’s a start:

eldon and joey

We made it to Morgantown by nightfall and had dinner at the Mountain State Brewing Company: a large spicy pizza cooked in a wood-burning oven, washed down with a couple of pints of their homebrew.

mountain state brewing company pizza oven

“Not a bad start,” I said, toasting Eldon with my glass.

Next: The accordion comes out!

3 replies on “Toronto-to-Tampa Road Trip, Day 1”

It’s supposed to be Crown Royal, but you look like Burger King!

Congrats on your new salary, and your relocation! /rd

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