3:00 p.m. EST on Saturday, your boy is pulling up to the Canadian border in Michigan after six hours of car time logged. I’m exceeding Wooderson rolling up to a high school party levels of pure, unadulterated excitement.

Fueled by a Teddy Roosevelt daily intake of coffee, beef jerky, trail mix, and key lime pie-flavored protein bars, I reckon it’d be difficult for any onlooker to ascertain whether I was excited or mainlining Monster Energy drinks.

In the same ballpark? Meh.

I roll the windows down and promptly switch my Spotify from Empire of the Summer Moon (a fascinating listen about America’s war with the Comanches) to my “Happy Feel Good” mix and, what do you know, I’m rewarded with none other than Low Rider.

I hit the volume up a few notches and pretend I still have my luscious, long hair and that the wind is blowing all up through that bitch.

I’m a mullet, mustache, and sleeveless stone-washed jean jacket away from blowing the top off this popstand.  Or Rav4 as it were.

In short, I have arrived.

I creep up to the first stop in the border crossing process and go through the standard rigmarole of questions.

As I’m answering the simple “Where are you going? Why are you here? What are you doing?” routine, I realize that my speech is clipped, hurried, and frankly a little chaotic. The words in my mind are not forming exactly how I’d like them to come out of my mouth.

I guess that’s the result of saturating myself with coffee and road trip snacks for six hours straight.

Needless to say, the first checkpoint was not to be my last. I was directed to pull to the right toward the customs and immigration building, where someone would give me my next instructions.

This is the moment when I realized that I’d researched every aspect of launching my nomad life in Montreal with a fine-tooth comb.

Except for the most important part.

Does Canada allow people to meander around their country while working remotely?

Two Border Control officers point to a spot and ask me to get out of the car and hand them my passport. Their stares are a combination of stink eye and anticipation for the loads of contraband they were certain to find.

The extensive search of my vehicle and all my life’s belongings commenced.

Blessedly, I am sober and no threat to be transporting drugs of any kind. Weapons are not my thing. They could’ve taken the whole bloody car apart piece by piece and they’d have found nothing.

The gusto with which they examined every inch of the inside of my luggage and every pocket in every bag made me think they just might do that. And throw in an anal cavity exam for good measure. It certainly felt as though they were expecting to find the mother lode of something. I felt like I’d been transported directly into a scene from Blow.

Twenty minutes later, with much chagrin and disdain, they gave me my passport back and sent me inside to speak with Immigration.

“They will decide whether or not you can work in Canada.”

So you’re saying there’s a chance… that I won’t be able to???

My bubble hadn’t burst this dramatically or quickly since Cliff Bruckner returned the “Do you like me? Circle yes or no.” note that I slipped to DeeDee Cada in the fourth grade.

She circled no.

Not unlike today’s unsolicited dick pic tactic, at some point in time a young lad sent such a note to the romantic object of his desire and it paid dividends. We men are copycats and simpletons. If it’s easy and works for one man, the male general population will shamelessly copy, paste, and repeat.

I shuffle in the door to find no other travelers in the building. Just me and five or six ornery immigration officers casually chilling at their computers.

This concerned me.

I did not want to be the big fish on the slow day.

I quickly went to my comfort in moments of uncertainty and ignorance… and called on Gloria (ChatGPT).

I relayed the details of my dismal situation to her, and she told me not to fret. This was all above board, and they were likely just concerned about me doing business in Canada.

Okay, phew.

I’m not a salesman. I am no threat to steal any business or commerce from Canadian establishments. I’m just an American working with my American clients and hoping to do so on Canadian soil.

After a few minutes, the interrogation begins.

And boy, did he frickin’ interrogate.

As though I were El Patrón himself.

During the course of the shakedown, I had to pull out my work laptop and show him an email with my corporate signature, take him to my company’s website, and show him my Airbnb and coworking space reservations.

My whole digital nomad plan flashed before my eyes. Everything is built on coming into Canada first. The possibility of being turned away at the border hadn’t even crossed my overstimulated mind.

My jittery nervousness skyrocketed to a state of full-blown catastrophizing faster than the line forms at 7-Eleven on Free Slurpee Day.

The interrogation even entered into inappropriate territory. I had told him my home base address in Chicago is my parents’ home (it is. That’s where my car is registered). He went so far as to ask, “So what are you going to do after Canada? Just go chill at your parents’ house?”

First of all, what in tarnation does that have to do with me being in Canada?

Second of all, no. I’m going to travel through New England and then head south when it gets cold.

Third of all… so what if I am?

Aren’t we feeling a little high and mighty from your throne of judgment?

After about twenty minutes of questioning, the officer finally looks at me and spits out, “I see no problem with this. We let people come here to work. Just do what you told me and we’ll let you back in next time.”

Great Odin’s ravens… it took a solid two hours for my stress levels to rev back down after this malicious attack on my nervous system.

Planning on coming to Canada from America to nomad?

Prepare for all the smoke, fire, and maple syrup Molotov cocktails.  And maybe go easy on the coffee.  Or at least eat lunch.