Planes, Points, and Packing Cubes- Confessions of a Frequent Flyer
By Claire Brady
I love what I do. As a higher education consultant, I get to partner with incredible professionals from campuses all across the country. But let me be clear: while I love being on the road, I just tolerate the getting there and back.
After 30+ trips a year, I've fine-tuned a travel routine that keeps me sane, efficient, and ready to show up at my best. The math is compelling: my system saves me 100-150 hours annually—that's nearly three full work weeks I get back every year. I make no apologies for the rituals, products, and hacks that make business travel feel like an extension of my real life, not an interruption.
Here are my seven non-negotiable travel rules that have transformed 30+ annual trips from survival mode into a sustainable lifestyle:
Prioritize Safety Over Everything
Late-night Uber over sketchy transit? Yes. Hotel with interior corridors and well-lit parking? Always. Rental car from the main lot instead of the economy shuttle pickup in the middle of nowhere? Absolutely. No shortcuts here. Ever.
The Power of Ritual: Small Habits, Big Impact
Consistency creates calm. When everything else about travel is unpredictable—delays, cancellations, that mysterious hotel room smell—having non-negotiable rituals keeps me grounded.
My travel rituals are simple but sacred:
Always sit near the front, always choose the aisle. Front of the plane means faster boarding and deplaning. Aisle means bathroom access without climbing over strangers and easier overhead bin access.
Pack light, pack smart. I can fit everything I need into my carry-on because I've curated my travel wardrobe down to pieces that work hard and play well together. Less stuff means less decisions, less weight, and less worry.
Wear my travel uniform. The same high-quality, trusted pieces every time—clothes I know won't wrinkle, won't fail me, and will keep me comfortable from departure to destination.
Unpack the moment I reach my hotel room. Before I check email, before I grab dinner, before I do anything else. It signals to my brain that I've arrived, I'm settled, and I can shift from travel mode to work mode.
Loyalty Pays Off—In Points and Mental Energy
Stick to one airline, one hotel chain, and one rental car company as much as possible. I'm loyal to Marriott, Hilton, and Hertz. However, I fly all over the country, which makes airline loyalty tricky. While I'd love to rack up elite status with one carrier, the reality is that I prioritize direct flights and reasonable prices over loyalty points. A two-hour direct flight on any airline beats a four-hour connection on "my" airline every time. It's not only about loyalty—it's about reducing friction and maximizing ease. Every little convenience compounds into a more sustainable travel life.
Time Is Money—and Peace of Mind
I've calculated that not checking bags, eating in the airline lounge, walking straight to a rental car pick up, and having grab-and-go toiletries saves me 5 hours per trip. Multiply that by 30 trips a year, and I reclaim ~150 hours annually—up to 19 workdays. That's not a luxury. That's sanity. And it's the difference between dreading travel and simply getting on with business.
Never Check a Bag. Period.
Unless you absolutely must for truly essential reasons (think medical equipment), don't do it. I checked a bag exactly once this year—on a small regional jet to Mobile, AL. Plot twist: another passenger on my 30-person flight had identical luggage. I grabbed his bag, drove to my hotel, and only discovered the mix-up when I opened it to find men's clothes and someone else's prescription medication. Cue the panicked calls, the drive back to the airport, and the delayed evening prepping for the next day.
Systematize the Packing and Unpacking Process
Here's my counterintuitive secret: I keep duplicate toiletries in a permanently packed bag. This system cost me about $200 upfront to duplicate everything, but it's eliminated the "Did I pack my phone charger?" panic forever. Future me is always grateful.
Invest in the Right Gear—Your Back and Sanity Will Thank You
If you're going to live by the carry-on-only rule, your luggage needs to work as hard as you do. After testing many brands, I swear by my Away carry-on. It's lightweight, durable, and the wheels glide on every surface.
But here's what nobody talks about: you need a quality backpack too. A quality backpack keeps both hands free for the million small tasks that pop up during travel—from showing boarding passes to grabbing snacks to actually being able to text without dropping everything.
Clothes matter more than you think. I've ditched anything that wrinkles, restricts movement, or requires special care. My travel uniform is all about layers: layers that look professional but feel like pajamas. The goal is looking put-together while feeling comfortable enough to sleep in an airport chair if needed.
Shoes can make or break a trip. I converted to Hoka sneakers for travel days and haven't looked back. They're comfortable enough for a full day of walking and supportive enough that my feet don't revolt after 12 hours of travel.
The backup-to-the-backup rule: I travel with multiple sets of headphones (wired and wireless) and at least two wireless chargers. Technology fails at the worst possible moments, and there's nothing worse than being stuck on a delayed flight with dead earbuds and a dying phone. Redundancy isn't paranoia—it's planning.
Unpack Immediately
I don't want to see my suitcase a second longer than necessary. It signals to my brain: you're home, reset. The transition from travel mode to life mode happens instantly instead of lingering for days.
My Best Travel Investments:
Loyalty program fees and status matches: $400
Duplicate toiletries and comfort items: $200
Quality carry-on luggage & backpack: $400
TSA PreCheck and Global Entry: $150
Annual return: 100-150 hours reclaimed, countless stress headaches avoided, and the ability to show up as my best professional self instead of a frazzled traveler.
What's Your Biggest Travel Pain Point?
Whether you're in education, consulting, or any field that has you living out of a suitcase, I'd love to hear what's helping you thrive while on the road?
