How Not To “Lose Your Sh*t” When Traveling

Because I’m absent minded, traveling is an extra challenge for me, constantly forgetting important paperwork, keys, wallet, technology, head, etc.

This way of being forces one to pay attention to details.

Even though I do hate the expression, “You can never be too safe!” (which I disagree with!), there is a time and a place to consider safety.

In my opinion, most people that obsess about safety when traveling are doing so as a reason not to travel. If you can safely say this isn’t you, then read on!


My primary considerations when I travel are:

-Losing my laptop
-Getting robbed/losing my wallet
-Losing my phone
-Losing my passport
-Getting my place broken into

1. Losing my laptop. Well I have a funny story here. I was driving from San Diego, CA to Austin, TX. I swung by a Starbucks in a stop in Midland, TX to find a hotel to stay at in the town.

Somehow, the town was completely sold out of hotel rooms that night! Surprising, considering that expression “fair to Midland”, I never thought of it as such a hotspot.

I was kind of stressing out, because it was already 9 pm and it looked like the next town was 2.5 hours away. I quickly booked something there, closed my laptop, and scrambled down some pretty sketchy highways to get to San Angeles or something like that.

I arrived, checked into my hotel, exhausted and ready to crash. Grabbed my laptop bag and…..WHAT? it  seems very light…..WTF, no laptop in bag!!! My heart dropped, I began to panic.

As I was sweating bullets, I called the Starbucks, on the off chance that they have my laptop. No answer, they’re long closed. Set my alarm for when they open, called them and….WAM!

They have my laptop! Wow.

So rather than a complete disaster, it was about a 4.5 hour detour (maybe I didn’t drive the speed limit on that portion).

Morals of the story are: Always check twice when leaving a coffee shop, be extra mindful when you travel…and if you’re going to lose a laptop, let it be Starbucks where the employees generally rock. 🙂


2. Getting robbed/losing my wallet. This is kind of multi-faceted. I have luckily never been robbed while traveling. I do, however, take some precautions. I don’t carry a ton of cash.

I always carry my wallet in my front pocket. And, I don’t keep much money in any one bank account. It’s also a good idea to keep any extra ATM or credit cards somewhere other than your wallet. If you get robbed, you aren’t completely screwed this way.

Another story. I was in Bali, and had been there a month. I was headed to the airport to catch a flight to Singapore. Whoops! I overstayed my visa by 1 day and owed the authorityes 20 bucks. Since I spent all my cash, I had to go to the ATM to get more to pay them off.

Butt…..I got to the ATM right outside the airport and…nope! My ATM card was NOT in my wallet. I had left it in one of the ATM machines in town! Wow. I quickly went to a gift shop and talked them into letting me buy a pack of gum for $50 and get cash back. I barely got everything done and caught my flight just in time.

However, not having an ATM card is ridiculously hard when traveling (what did people do before ATMs?). I was able to pull it off with the help of Western Union.

But the kicker was- when I got home from my trip, I found my “backup” ATM card in my backpack in a special pocket!

“You can never be too safe!”

Yes, you absolutely can.

3. Losing my phone. Well, my phone is now attached to me like an appendage. It’s unhealthy but I would just about as likely lose my head as lose my phone. Having said that, I have another story. In Mexico City last year, I was in a taxi coming back from Teotihuacan.

The driver was hilarious and interesting, but also a crazy driver! He kept flooring it in the city and calling pedestrians “points”. “10 points!” “20 points! HAHHAHA!” At the last second he would swerve around them and laugh.


Needless to say, I was distracted and had set my phone on the seat.

When I got back to my hostel, I realized….taxi had my phone! Luckily, the front desk had called the very taxi we were in earlier that day. So they were able to call the driver himself, who promptly turned around, and came back to deliver my phone! My life kind of flashed before my eyes this time.

Lesson learned: When chaos happens, don’t lose your head (and leave your phone where it belongs). And of course, always password protect your phone, and go with an iPhone (as they will even stand up against the FBI when push comes to shove to protect your data!)

4. Losing my passport. Luckily, this hasn’t happened to me. But as demonstrated, I am clearly prone to losing things. So I do two simple things: Keep copies of my passport, and ALWAYS leave my passport in the same pocket of my backpack.

It’s annoying that in this digital age, governments around the world continue to exist in the stone ages, and we have carry around pieces of paper to go through these imaginary lines in the sand, but it’s important to remain vigilant about passports until there’s a better way.

5. Getting my place broken into at home. I actually don’t worry about this, however, I tend to live in gated condo buildings that face little risk of break-ins.

Believe it or not, I feel safer when I Airbnb my apartment to a stranger when I’m gone, rather than leave it empty. With Airbnb’s rating system, I have always felt comfortable letting people stay in my place (for a few bucks :)).

There is zero incentive for them to steal anything or mess with your stuff, because one bad mark on the site and they will be done renting for a long time.

Alternatively, if random strangers from the internet staying at your place freaks you out, there are alternatives. You can ask your friends or social groups for referrals to housesit. This can be with or without a fee. If you live in a nice area, you shouldn’t have too much trouble finding takers here.


One more story: I did have a close call with an Airbnb experience. But it wasn’t the tenants themselves that were a problem.

Last year, I left for a a 2-week trip to Panama, and rented out my place to two different parties, each staying for a week. Around Day 5 of my trip, I got an email from my building’s HOA.

Low and behold, they said they caught wind of people renting out their places online, and this is strictly prohibited in the building, and anyone caught would be evicted! I hadn’t realized this and started to panic.

I called my tenant #2 and explained the story. We decided that he almost certainly would not be bothered, and I would not be “caught”, but we had a story ready nonetheless. All went well, no problems, no evictions. But it was my last time renting that place out when I traveled.

Another option here that I just learned about:

Now there are officially no excuses not to travel. 🙂

What do you think? Do you have any other fears or ideas around the idea of travel safety?

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Kevin Koskella

Kevin is a podcaster and writer on living free, despite the crazy world we live in. Kevin travels full time and explores the world and how to achieve and maximize freedom in life.

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