Road Trip Diaries: Losing My Shit In Canada

Would you lose your shit driving across the country for a month?!

On August 8th, I kicked off a road trip with my business partner, taking our podcast, Discover Your Inner Awesome, on tour around the country.

So far, we’ve hit Kansas City, Denver, Seattle, Portland, LA, San Francisco, and I am currently writing to you from Las Vegas. Next up, we check out Austin, Houston, and Nashville.

If you’d asked me at the beginning of the trip where I thought things would get the most crazy, my mind would have burst forth with tales of Vegas flashbacks. Like the time I blacked out and stole a cop car, strapped a baby to my chest, returned a tiger to Mike Tyson, and found my friend stranded on the roof of our hotel with no water and a wicked sunburn with hours to spare before his wedding.

...wait, that might have just been the movie The Hangover. I can’t remember.

Regardless. What I did not expect was for Canada to be the place where I completely lost my shit!

What Happened?!

Over the weekend, we took a break from the road trip. Raj went to Tahoe, and I went to Ontario, Canada to celebrate my friend’s wedding. To get there, I flew from LA to Chicago, then drove with my friends across the border.

It was supposed to be a fun weekend break from the busyness of the road trip. But, as with most of life, plans don’t pan out quite as you’d expect.

For me, it was a crash-course in learning how to roll with the punches.

Now, when I say I lost my shit in Canada, I don’t mean that I embarrassed myself singing, dancing, toasting, and celebrating love. Although I did a lot of that at the wedding too.

...yep, that's me in the corner.

What I mean is that my bags got stolen and lost everything!

Including my…

  • iMac
  • iPad
  • External Harddrive
  • iPen (no, not the fancy new apple one, but still a nice stylus)
  • Passport
  • Drivers License
  • Bluetooth Keyboard
  • All my credit cards
  • Transit Card
  • Pebble Watch Charger
  • Shorts
  • Shirts
  • Swimsuit
  • Jeans
  • Belts
  • Brand new OR foldable hat! (loved that hat!)
  • Socks & Underwear (enjoy my undies thief!)
  • Hoodie
  • Toothbrush & Toiletries
  • Notebooks
  • Sunglasses
  • ...and pack of almonds (you monsters!)

How the hell did that happen?!

In hindsight, there were many things that could have been done to avoid losing so much so quickly. But, for a variety of reasons, those safety measures didn’t happen. Thus, I found myself bringing all of my bags along with me to the wedding.

No, I didn’t bring them to an old Canadian church. The wedding was at their parent’s home and was an amazing backyard celebration overlooking lake Huron. I’d brought everything with that morning to be prepared for whatever they might have planned for the day.

I spent the day raking the beach (we made a big sand heart! ...insert "awwwww"), helping my friend practice the best man speech, and brainstorm last-minute vows with the groom. Then...the wedding began!

We celebrated, boogie-oogied, broke-it-down, and even did the stanky leg, before grabbing my bags and hopping on a bus back to the hotel.

At the hotel, I stopped to chat-it-up in the lobby before heading up to the room, but when I finally got to the stairwell, oh no! I realized I didn’t have a room key.

Knowing that Canada is the land of unlocked doors and friendly neighbors, I figured it wouldn’t be an issue to put my bags down for just a minute while I ran back to the front desk to get a new key. (smart right?!) Plus the security guard was like 10 feet away. What could happen?!

I was gone for a minute-in-a-half, but when I returned to the stairwell, as though they were Keyser Soze, poof! They were gone!

There I sat, in the lobby, with nothing but a suit bag and the clothes on my back.

The hotel staff and the police were no help. I’d almost call them incompetent, but then again I am the guy who left his shit in the stairwell next to an exit, so I’ll hold my throwing stones for now.

Rolling With The Punches!

My bags were gone, my passport and ID were never coming back. It was now time to roll with the punches. I had a minor panic attack while calling my parents in the morning, but overall I kept a fairly good “shit happens” outlook on the whole thing, trying to find the humor where I could.

For instance, you should have seen how stylish I was while we were getting breakfast in the hotel. I wore my best...well, my best friend Dave’s sleeping clothing. Including his deep-v-neck shirt, running-short-shorts, and the colorful dress socks and brown dress shoes I had on at the wedding.

...I looked hot, ladies (insert kissy face emoji)

I spent the morning trying to figure out how to get back into America without a passport, calling the police, the Canadian Border Patrol, my credit card companies, and anyone else who would listen to me. It was a holiday weekend in both America and Canada, so most of them were screening my calls.

Fortunately, I managed to escape the clutches of Canada and return to the red, white and blue. Unfortunately, my glasses broke at lunch… rolling with the punches, right?!

I made it back to Chicago and pushed my visit to Vegas a few days so I could get new ID, cancel all my credit cards, figure out what to do for a computer and money, and get my life back in order. (Thanks for letting me borrow your computer Mom!)

I boarded the plane on Wednesday morning to get the car in LA, after 2 days of visiting every DMV and security hotline I could find, and thus ended the Losing My Shit in Canada fiasco!

5 Things I Learned Losing My Shit in Canada.

  1. Canada does have crime. Or, at least one thief that I know about!

  2. ou should always keep your passport on you at all times, even if you’re sweating it up in a suit on the dance floor.

  3. No matter what happens, try to find the funny. Even if the funny thing is just walking around in dress shoes and short shorts.

  4. Save everything important to the cloud. Always.

  5. Keep Calm Carry On!

Keeping it Calm in Vegas!

After 15 hours of flying and driving, I made it to Las Vegas yesterday. Right now, I am writing this email in the windowless business center of the Monte Carlo hotel, where I’ve spent most the day, working on my mom's Windows PC, while the city parties at the pool downstairs.

It isn't as crazy as Canada, and ain't no Hangover Part II, but it is life and I am rolling with it.

Have you ever lost your shit and had to roll with the punches?

Reply to this email with your story and how you handled it!

Also, check out Idea Lemon's most recent podcast with The Unmistakable Creative, where we ironically talk about “Rolling with the Punches”, despite this episode being recorded days prior to my bags mysteriously disappearing.

 Keep Rolling,