For the past couple of decades, I’ve traveled 60-75 times a year—mostly for public speaking, client visits and occasionally vacation. My trips are mostly independent and domestic, with Vegas, Orlando and New Orleans topping the list. My goal? Get it done as fast and affordably as possible. Eyes down, earbuds in, mouth shut, mind your own business — especially on business trips.
If you’re a frequent business traveler like me, here are 10 lessons I’ve learned to make travel easier, cheaper and less painful:
1. Lean into loyalty
Even if you only travel a few times a year for business, it’s critical that you join the loyalty program of the airline that most frequents your local airport, as well as one hotel and one rental car brand program. There are some cases where you may pay a little more. There are other cases where you might not get the best flight or location. But you’ll make up for these potential inconveniences by building up points which can then be converted into free rooms, flights and car rentals, and the payback will be greater than what you paid. Some loyalty programs offer other rewards, such as discounts on partner brands, which will save you more.
Also, as your status rises, you’ll get free upgrades, better seating and baggage allowances without fees and — to me, most importantly — special attention like fast re-booking when things go wrong. Lean into these loyalty programs, eat the dog food and over the long term, you’ll benefit both from cost and productivity.
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2. Avoid airline and hotel travel cards
Airline and hotel credit cards aren’t worth it. Sure, it can seem enticing when they offer lots of miles upfront for signing up or expedited boarding. But the interest rates and fees on these cards will, over the long term, be higher (in my experience) than those of their competitors. Also, you’re limited to only choosing flights and hotels with that brand, which significantly limits your choice of available flights, and you’ll be blacked out during high-volume periods.
If you’re a business traveler, choose a card that’s tied to an independent travel service. I’ve enjoyed the Citibank Thank You program for years because I accumulate points both for my business and personal cards, am able to combine those cards, and then can convert those points into travel with their agency that books on just about any airline or hotel I choose. Another trick: I’ll stay at Marriott (my preferred hotel loyalty brand), charge everything to the room, including meals and drinks, get points for the hotel and then pay the bill with my Citibank card so I earn points on the card as well — double dipping. Double the benefits.
3. Subscribe to a travel newsletter
There are a few great travel newsletters that you can search and subscribe to (I like The Points Guy), which can help you figure out the best travel and let you know quickly when there are programs or special deals launched. Like grocery coupons, some people go crazy with this stuff, and yes, they do save money (although I’m not sure how much time they’re spending in return for the benefit). Regardless of how much you lean into these services, they’re helpful to keep you aware of potential discounts that, if the timing’s right, can save you money that you weren’t expecting to save.
4. Do not wait in rental car lines
Thank God we don’t live in the days of our parents, when renting a car required sixteen forms of identification and a strip search. Some of the better rental agencies (I like National Car Rental) let loyal users bypass the check-in process, go straight to the garage, jump into a car and then drive away by just showing their driver’s license. And on return, you get out and go. I find this experience to be cost-efficient, productive and frankly, exhilarating. It’s all about time, and I pity those people standing in long lines waiting to be approved to drive.
5. Eat at chains
If you’re not a frequent traveler, eating out can be fun. But for the rest of those who travel many times a month, we need consistency and affordability. So when it comes to food, I generally stick to a chain restaurant. Unless I’m entertaining clients, which I rarely do, I’m happy to get a filet at Outback Steakhouse for $40 that includes fries and a salad rather than paying $125 for the same meal at the local steakhouse. Chain restaurants tend to be reliable, faster and more affordable than other restaurants. Other times, I avoid the $30 hotel burger and get Uber Eats delivered. You want to go local? Find a diner. Or otherwise stick to your hometown.
6. Use expense management apps
I’ve wasted countless hours doing expense reports over the years. But no more. Thanks to great (and inexpensive) expense management applications like Expensify, SAP Concur, Ramp, and Zoho Expense, business travelers can, just by snapping a photo, have their expense time sheets done with minimal involvement, which saves time and mistakes. I’ve got my car rental, airline, hotel and rideshare apps all connected to the service I use, and when I eat out or take a taxi, I upload a quick photo. When my trip is over, my expense report is done for me. If your business has a team of travelers, it’s a great way to manage their expenses and, after integrating the app with your accounting system, save a significant amount of back office time. Thanks AI!
7. Tip generously
Tipping doesn’t save you money. It’s just the right thing to do. Carry some cash and take care of the people who clean your rooms with $10 per day. Give the valet another $10. Never tip below 20% on a restaurant bill. And yes, add an extra buck to the $8 cup of coffee you bought in the casino lobby. It’s not their fault that the price is ridiculously high. And you can afford it. Tip more if you can.
8. Consider taxis for speed
Whenever I arrive at my home airport, I always block and tackle through the masses of people waiting for their rideshare and go straight to the taxi area, where there’s always a line of cabs waiting. I mostly do this in other cities, too. Generally, taxis still cost more than rideshares. And some of them aren’t as comfortable a ride. But it’s all about time, and whatever gets me to my home or my destination faster so I can finish with the travel experience is, to me, worth the added cost.
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9. Double down on your security
Don’t be stupid with your data when you travel. Don’t reveal your private work to the guy sitting next to you on your flight. Buy a laptop privacy screen, a piece of plastic that makes it impossible for anyone not directly in front of your screen to see what you’re doing. Make sure you use a VPN service to encrypt your data when on a hotel or airport Wi-Fi.
Better yet, don’t use the hotel or airport Wi-Fi and use your mobile hotspot whenever and wherever you can for the best security. Don’t do any banking or financial transactions when you’re on the road if you can avoid it. Bring an extra battery pack so that you don’t run out of power mid-trip when you need to get work done. And bring three separate power cords in your bag because these things fail (and so do you when you forget one in your room).
10. Roll your clothes
Checking a bag not only incurs extra charges but also extra time at the carousel. To avoid these fees and get on and off the plane (and in and out of the airport) as quickly as possible, my advice is to roll. Yes, roll. Roll as many of your non-wrinkle clothes (socks, underwear, shirts, etc) and align them in your carry-on bag, starting on the outside and working your way in. You’ll be shocked at how much more stuff you can fit in your bag that way. Make use of the hotel iron if needed.
20-plus years of travel. 60-plus separate trips per year. And I’m still not in the higher echelons of the business road warrior. Thank goodness. Regardless, this is what I’ve learned. You’re welcome.
