Over the last 15 years, I’ve flown more than 4.5 million miles—conferences, clients, colleges, and more. Along the way, I’ve built a reliable system that makes travel less stressful, more productive, and surprisingly affordable.
Here’s my personal checklist—the exact things I do to travel like a pro.
1. Build in Buffer Time
Even with a locked-down travel system, I always give myself breathing room. Here’s why:
- Leave room for the unexpected: meetings run long, flights change, or something goes sideways.
- Some of the best experiences happen outside the schedule—local food, spontaneous conversations, and hidden gems.
- One time in Costa Rica, my car broke down. I was a full day from civilization. That buffer saved the trip.
Even when I cut it close, it’s intentional. Like this:
- Left my house at 11:32 a.m. for a 12:25 p.m. flight out of Las Vegas.
- At the airport by 11:45.
- Through security by 11:48 (thanks to PreCheck + CLEAR).
- In the lounge by 11:52.
- Ate two bowls of soup, three sandwiches, and a latte.
- Left at 12:02 and still made it to my gate at 12:11.
- Boarded early and got my favorite aisle seat.
It only looks risky if you don’t understand the system.
2. Stack the Right Programs to Save Time
To move fast and skip lines, I stack these:
- TSA PreCheck: essential for domestic flights.
- CLEAR lets me skip to the front of PreCheck.
- Global Entry + Nexus: saves a ton of time re-entering the U.S. and Canada.
- TripIt: automatically tracks all my flights—I’m at 11 million miles and counting.
If you travel internationally even once or twice a year, these are a must.
3. Never Check Bags (Even on Long Trips)
Here’s what I pack for a month-long trip using only a carry-on:
- 22-inch expandable TravelPro roller board.
- Backpack (fits under the seat).
- Two dress shirts.
- Two pairs of pants.
- Several t-shirts.
- Running shoes.
- Spare shirt and pants rolled up in the backpack in case I’m forced to gate-check.
Why? Because I’ve shown up to meetings in gym shorts before, once with the CMO of California Pizza Kitchen. That won’t happen again.
Also, never use a neck pillow. It screams rookie. Flight crews use TravelPro for a reason—durable, discreet, and efficient.
4. Use Airline Loyalty and Credit Card Hacks
I fly Southwest a lot, and here’s how I use it:
- Southwest Companion Pass: once I hit 110,000 points, I can bring someone for free on every flight.
- Book multiple flights in advance to give myself flexibility, then cancel all but one at no charge.
- Standby for earlier/later flights—Southwest lets me shift, even outside the two-hour rule.
- Always ask for the whole can of soda—three times the drink, no extra cost.
On top of that:
- Priority Pass Elite (via Southwest credit card): free lounge access + 2 guests, no limits.
- I eat more meals in lounges than I do at home.
- Lounge access means food, Wi-Fi, showers, quiet workspaces, and meeting rooms.
- I used to use Admirals Club access via American, but they now require an AA boarding pass.
All of this together gives me flexibility, comfort, and control at every stage of travel.
5. Work on the Go
Just because I’m flying doesn’t mean I stop working. My system keeps me productive from anywhere:
- Use lounges as remote offices—I’ve hosted team interviews, investor meetings, and strategy sessions right in the Admirals Club.
- Preload videos with YouTube Premium to stay productive even when there’s no Wi-Fi.
- Carry all chargers, adaptors, and backup batteries in my backpack.
- If there’s no outlet? No problem. I’ve already planned for it.
Every minute in transit is either productive or restful by design.
I don’t just work alone either—my business partner Jack Wendt and I have produced content right from airport lounges. We’ve outlined strategy decks, recorded one-minute videos, and built entire course modules while waiting for our next flight.
The produced content is automatically uploaded to my Google Photos, where VAs turn it into blog posts, snippets, and training materials using our 4-stage Content Factory process. It’s how we scale what we do—on the move, without slowing down.
6. Always Travel with Purposeful Gear
Everything I pack serves a function:
- TravelPro roller board and backpack.
- Chargers and a power bank.
- Goggles (hotel pools).
- Frisbee (easy to pack, great exercise on the go).
- Gift cards and giveaways for flight attendants or team surprises.
- Ring lights (I give these away when someone films a great one-minute video).
- Rubber chicken (yes, seriously—it’s a great conversation starter).
This combo lets me stay light, mobile, and fully prepared.
7. Choose Hotels That Match Your Routine
Not all hotels are created equal.
- I pick hotels with 24-hour gyms—especially if I land late.
- I avoid places like Vegas that shut down their gyms early.
- Fitness, rest, and reliable Wi-Fi are non-negotiable.
- The hotel is my base, but it has to support my workflow and wellness, not distract from it.
8. Leverage Every Route and Program
In addition to Southwest:
- I use Frontier’s GoWild pass when they have direct flights—unlimited travel for $299/year.
- I used to fly from DFW to LA to visit my mom for $7 as an American Airlines employee.
- First class used to be $21. I’d only pay it if there was a meal.
- An international first class on AA cost me $100 and included caviar, Häagen-Dazs, and lie-flat seats.
That’s what I mean by “first class on a coach budget”—not cheap, but strategic. It’s about value per dollar, not frills.
9. Go Places People Don’t Expect
One of my favorite trips ever? Almost the North Pole.
- Flew from Oslo to Svalbard, a town at the 78th parallel.
- Glaciers, polar bears, ice caves, Northern Lights.
- Cold, remote, unforgettable.
You don’t need luxury. You need curiosity—and a system that gets you there.
Final Thoughts: Make It Repeatable
People say what I do is risky. Or impossible. But it’s not.
It’s a checklist. It’s a system. And I’ve been using it to travel the world for over a decade, personally and professionally.
If you want to travel more, spend less, and stay productive along the way, copy the checklist above. Then test, tweak, and make it your own.
I don’t spend more than most people on travel. In fact, I’d bet my monthly travel costs are lower than your rent or mortgage.
But I’ve built something that works. And you can, too.
What’s one hack from this checklist you’ll actually use on your next trip?
