I was standing on the sidewalk in Charlotte, getting ready to head to the airport for a flight home after a few days at a conference. I was about to hail a cab when I received a notification that the first leg of my flight home had been delayed, eliminating my layover and causing me to miss the second leg of my flight home. A year ago, I would have panicked. But now, I'm prepared.

I've got a folder of travel apps on my phone for exactly this purpose. Within 15 minutes, while standing on the sidewalk, I was able to cancel my delayed flight, secure a refund, confirm it had processed, book a new flight home with another airline, check-in, and hail myself a ride to the airport. Piece of cake. 

I've written before about the  less tangible lessons I've learned from living so much of my life on the road, and offered a few packing tips, but this column is a bit higher level. This is about two big travel lessons I learned the hard way, and recommendations for the things you should invest in to make traveling a better experience for you. Because if you're going to be on the road, you might as well enjoy it. 

Invest in a good suitcase. Seriously. 

I traveled with a crappy suitcase for a long time. Too long. First it was a duffel bag, which I used largely because it was light and never got flagged for mandatory gate check-in, saving me from having to wait in baggage claim. But it didn't have wheels and it was no fun to cart around. I upgraded, only slightly, to a cheap rolling suitcase. This got flagged for gate-check more often, but it was easier to roll this around than to carry a duffel on my shoulder. Until the wheel broke one day into a 4-day trip and I wound up carrying that too... 

Recently, at the suggestion of a fellow road warrior, I upgraded to a "Bigger Carryon" from  Away luggage, which is small enough to be a carry on, but comes with four sturdy wheels for easy rolling and--the true savior--a charging pack built in for keeping phones and other devices fully charged on the go. I can't tell you how much stress this saves me at the airport, knowing I don't have to jockey for an outlet under a table somewhere to pull up a mobile boarding pass. I wish I'd done it much sooner. 

Banish dead batteries with duplicate chargers.

On one of my first big trips to present at a conference, I had a panicked moment at the gate where I realized I'd forgotten my laptop charger. My dwindling 15% charge wasn't going to last me through a 4-hour flight, a full rehearsal, and a one hour presentation. I emailed the event organizers to ask about a spare, tweeted to some friends in the area begging to borrow, and even tried (very desperately) to book a TaskRabbit in my destination to go buy one and drop it at the venue before I arrived. No luck. 

I got lucky. My flight got delayed. I ran out to the curb and pled my case to a cabbie who agreed to drive me to a local Best Buy, wait outside for me to buy a replacement, and rush me back to the airport before my new departure time. It worked, but it was one of the most stressful and hectic mornings in recent memory. (It was also an expensive lesson: A $70 replacement charger and a $60 cab ride to get it.)

I vowed it would never happen again.

As soon as I got home, I bought a copy of every piece of tech I travel with: phone charger, international power adapter, and other assorted dongles, cords and adapters. I put those (and my new duplicate laptop charger) all in a nice zipper pouch that stays in my suitcase, ready to go. 

And I'm always adding and updating it. I recently added my own Logitech slide advancer/clicker to the pouch, and I just ordered The SideWinder, an attachment that neatly coils that cumbersome backup Apple charger to make it easier to transport.

Now that I know I won't have to struggle with my bag, or worry about forgetting a charger, I can focus on other things: catching up on work,  rehearsing my speeches, making new friends and finding the best possible coffee and ice cream in each city I visit. If you can identify the elements and variables that make travel stressful for you, and take steps to render them impossible (or at least improbable) you can spend more time enjoying your travel, and less time worrying about it.

Published on: Oct 16, 2017