No rent. No bills. No boss.

Leaving our Northern Ontario home to travel the States for three months was a glorious idea. We could work from cafes, libraries, and lobbies. We were staying with friends and families all over the Eastern United States. Our expenses were going to be light. I could still get work done for all my northern clients. All I needed was my laptop and a wifi connection.

We were going to be digital nomads. We could set our own hours and be our own bosses. The Internet has freed us from the 9-5. We could travel and still make a living.

However, no border crossing guard seemed to enjoy the idea as much as we did.

We rolled up to the border crossing, ready to hand over the passports with a smile.

Let me defend myself before I make a fool of myself. Trust is easy for me. It's hard not to be honest. If everyone were upfront about their lives, the word would be a simpler place... Right?

So I was completely honest with the bearded gentleman. He looked like we could have gone to high school together. He would understand... Right?

“Where are you going?”

“All over the place. But Ohio tonight.”

He looks behind me to the back seat. Our Honda Civic was a jelly doughnut that could have burst under the pressure of his glare. I still didn't clue in.

“How long do you plan to be in the United States?”

“Three months.” I'm still smiling.

“Three months.” He lost interest, like he had heard this story before, “And how are you paying for everything?”

Right here, at this point, I could have said, “Our savings account,” and that would have been just as honest.

But I actually said, “Oh I can work from anywhere. I do copywriting and marketing so I can work for my clients from any cafe with wifi.”

I hadn't even finished my grand plan of how we were going to be digital nomads, travelling, with no strings attached. He was already writing something down on a small, white piece of paper. He handed me the paper, but kept our passports.

“OK. Park over there to the right, go in door number 2.”

I wasn't smiling anymore.

My wife and I like to travel. We travelled before we dated, we travelled while we dated, and we travelled after we got married. She had been stopped and questioned once before, when she was 14. I had never been stopped for questioning. And I went to school in the States for 2 years.

In the waiting room, I couldn't help noticing that we were the only white people. Is that racist? But it's the truth. I felt bad for the small families. Oh, there was one short, balding white guy. I think he was a truck driver and border guards didn't like what was in his truck. I didn't feel for him really.

But I felt for the family of three who hardly spoke English and had to endure the spit spray of an exasperated border guard explaining visa rules to them for the seventh time.

I tried everything to distract myself from letting our entire plan for the next 3 months flash before my eyes. People watching was one method. Luckily there was a T.V. with an American news station on it. But after 30 minutes, the news stories were repeated. This was the morning after mother nature tucked Buffalo into a long mid-winter sleep with a blanket of snow that was several feet deep. I remember watching footage of snow removal from some local high school at least three times.

When the distraction attempts failed, the possibility that all our plans could be plowed away with the snow outside made us hold on tight to each others hand.  We gave up our apartment. All our stuff was in a storage unit. What would we do if we couldn't cross? Go back? Back to a fixed life, with strings and bills? Back to real life?

Our sweaty, sore grip brought us out of the stupor. And our number was called.

The interrogating interviewing border guard was a short, middle aged lady who had put her son through proper trombone lessons and knew what it took to start a business, even though she had never started one herself.

When you cross into the States, you have to prove, beyond a shadow of a doubt, that you're not trying to live there. I don't remember how she started but it gets interesting about here:

“What's to stop you from staying here? How do I know you won't try to live here?”

I'm baffled, “Because we're Canadian. We don't want to live in the States.”

“Why not?”

I'm baffled again.

“And where do you plan on staying while you're here? Do you have an itinerary?”

“Not written out. We'll be staying with friends and family.”

At this point my wife is responding because every time I say something the lady snaps at me. I tried to offer up information at one point and she told me only to talk when I was answering a question.

“What family do you have in America?”

“My two older sisters married Americans.”

“And how do your sisters have the privilege of marrying Americans?”

I honestly don't remember how the response to that went. I know what the answer is, but I was blown away by this lady. American arrogance is something of a myth. I've lived there and never seen it, until this moment.

We explained that I went to school in the states and my wife did some missions work with a church organization in Orlando. The lady didn't believe I went to school in the states. I had to give her the schools website so she could see for herself that it was legit.

Then she says, “If I had it my way, you would be heading straight home. But it's not my decision. I'm going to talk to my supervisor.”

The fact of the matter is, when visiting the U.S., Canadians are more than welcome, but we have to prove beyond reasonable doubt that we aren't trying to live in the States. In our case, we didn't have an apartment, we didn't have a set itinerary, the essentials of our life were packed into our Civic (including camping gear, that the lady found out about), and we didn't have jobs to go back to.

There was reason for doubt.

We made it through. She gave us a lecture about working in America and a stern warning against even babysitting our nephews while staying with my wife's sister; that was considered bartering...

We were shook up, angry, confused, but when we arrived at our first stop, our hosts were embarrassed (but not completely surprised) by our story. Thankfully, the border encounter was the only shadow on that trip.

The truth is, Canadians can work in the States. You may have to apply for a visa if your staying there for a while, but to go in and out isn't illegal. Just be ready to pay taxes to the IRS like any other American business.

The digital nomad is free, but still has responsibilities. Taking advantage of the open road and open Internet comes with a few other details that you might not expect. But the freedom is still there.

There are still large pockets of society that don't understand. They think you're just “bumming your way across America” (an exact quote from border guard lady). They think you need to settle down, get a job, pay your dues and save up for retirement.

It's smart, but being a nomad connected to the digital world, free to roam the natural world is just as smart. You can still save. You can even climb the corporate ladder from home these days (tele-commuting).

This was a collision of naivete, old school determination, and new cultural exploration. It was surprising, but it was a hilarious start to an epic adventure (looking back on it, anyway).