Looking Back to Travel Smarter Going Forward

As we look back at the past twelve months, it’s clear that 2025 was a bit of a rollercoaster for even the most seasoned travelers. We saw unprecedented challenges, from the major software update failure in January that grounded over 5,000 flights to the nationwide technical outage that disrupted United Airlines hubs just this past August.

If you felt a bit of “travel fatigue” this year, you’re not alone. It is a lot to manage when the digital systems we rely on—everything from crew scheduling to baggage tracking—feel a bit more fragile than they used to. Even air traffic control staffing struggled under the weight of external pressures this autumn.

The good news is that these “tech hiccups” gave us some of the best travel intelligence we’ve had in years. We’ve learned exactly where the gaps are and, more importantly, how to navigate them. By looking at what went wrong, we can better prepare for what goes right in 2026.

In this week’s wrap-up, I’ve pulled together the most effective strategies we learned in 2025. These aren’t just productivity tips; they are “sanity savers” designed to keep you comfortable, connected, and protected no matter what the monitors at the gate are saying.

1. Strategic Seating

Long before you head to the airport, the quest for a smooth trip begins with the seat map. Most travelers choose a seat based on how close they are to the restroom or the exit. But if you want to maximize your comfort—especially on a long flight—try choosing your seat based on whether you are right-handed or left-handed.

For Right-Handed Travelers:

• The Best Seat: An aisle seat on the right-hand side of any section.
• The Advantage: Your dominant arm is free to move into the aisle space. This makes it much easier to eat your meal, use a tablet, or reach into your bag without knocking elbows with your neighbor.
• The “Pro” Choice: In a large 3-3-3 plane, pick the right-side aisle seat of the middle section. This gives you arm freedom and reduces the chance of a seatmate asking you to move.

For Left-Handed Travelers:

• The Best Seat: An aisle seat on the left-hand side of any section.
• The Advantage: You gain that same “infinite elbow room” for your left arm. It’s a small change that significantly reduces “cabin claustrophobia” during a long trip.
• The “Pro” Choice: On the left side of the aircraft, the window seat is often preferred by those who want to lean their left side against the wall to sleep, but the left-side aisle is where you’ll find the most physical freedom for tasks.

2. The Power Struggle

Whether you’re planning to use the in-flight Wi-Fi to check your hotel status or just want to listen to a favorite audiobook, your phone’s battery is your lifeline. One of the biggest lessons from 2025 is that airplane power outlets are notoriously inconsistent. Some seats have a standard plug, some have USB, and some—frustratingly—have nothing at all.

Even when a seat does have power, the physical ports are often “tired” from thousands of passengers. If you’ve ever plugged in your cord only to have it fall right back out, you know the feeling. 

To stay ahead of the game, I suggest a two-pronged approach for your carry-on:

• The “Squid” Cable: Instead of carrying three different cords, look for a “3-in-1” cable that has USB-C, Lightning, and Micro-USB ends. This ensures you can charge any device, and more importantly, it usually comes with a USB-A to USB-C adapter. This is vital because while newer planes are moving to USB-C, many older aircraft still use the traditional USB-A ports.
• The “Insurance” Battery: I never board a flight without a small, portable power bank. If your seat’s outlet is broken—which happened more often than not this year—having your own “mobile wall plug” means you won’t land in a new city with a dead phone and no way to call a ride.

It’s a small bit of preparation that removes one of the most common stressors of modern travel. When you know your battery is secure, you can actually relax and enjoy the flight.

3. Staying Connected in the Clouds

In years past, we often viewed the “Airplane Mode” switch as a forced digital detox. After the recent disruptions, however, many savvy travelers are finding that staying connected is a helpful way to stay one step ahead of the crowd. It’s not about working while you’re on vacation; it’s about having the tools to keep your trip on track.

Be aware that you can now take advantage of the free messaging offered by many major carriers. It’s a low-pressure way to keep family updated on your progress or coordinate a pickup if your arrival time shifts. It’s a nice “safety net” to ensure you don’t go entirely dark the moment the cabin doors close.

For longer-haul flights, you might even think about the paid Wi-Fi. It’s certainly not a requirement, but it can be a real “sanity saver” if you expect a tight connection or are concerned about weather delays. Having access allows you to monitor live flight updates or send a quick note to your hotel or car service to let them know you’ll be arriving late.

Pro tip: Major chains (Marriott, Hilton, Hyatt) have “Chat with the Front Desk” features built right into their apps. Many boutique hotels and international properties list their WhatsApp number on their website or in the confirmation email. If you have the app and Wi-Fi, you can message the desk directly. 

Think of it as a small investment in a smoother arrival—only if it feels right for your travel style, of course. It’s much more relaxing to handle those little “logistical ripples” from the comfort of your seat than to land and realize you have a problem to solve at the luggage carousel.

4. The Biggest 2025 Travel Insurance Lesson

If 2025 taught us anything, it’s that even the best-laid plans can be undone by a single system outage. While our in-flight hacks help you manage the experience of a delay, travel insurance is what manages the cost. This year, the “Trip Delay” benefit truly became the MVP (Most Valuable Player) for savvy travelers.

Many travelers don’t realize that if you are delayed for a covered reason—like a tech meltdown or a weather event—your policy can reimburse you for “incidental” expenses. We’re talking about the hotel room you didn’t plan to book, the taxi to get there, and even the meals you had to eat while waiting for the next available flight.

Here is the secret to a successful 2026: Keep your digital paper trail. 

Remember that in-flight Wi-Fi we discussed? Use that time to take a screenshot of your flight delay notice. If you have to buy a sandwich or a toothbrush at the airport, snap a photo of the receipt immediately.

Most insurance providers now allow you to start a claim right through their mobile app. By the time you finally board your rebooked flight, you could already have your claim documentation submitted. It’s the ultimate way to ensure that a tech glitch doesn’t become a permanent dent in your travel budget.

5. Landing with a Clean Slate

Before we close, there is one final “sanity saver” I’ve adopted this year.

On the flight home, while you have a few hours of downtime, take a moment to do a quick “digital sweep” of your phone.

Delete the blurry photos, the screenshots of maps you no longer need, and the duplicate shots of the same sunset. Create one folder titled with your trip name and move only your favorite memories there.

Pro tip: If you’re like me and take before and after videos of your rental car and leaving pics of your hotel room to avoid unexpected charges later, consider creating a subfolder and loading those assets there. You only need them if you get an unexpected bill, so they don’t need to be junking up your phone.

You’ll find that landing with an organized phone makes the transition back to “real life” much smoother. Instead of a cluttered camera roll reminding you of the stress of travel, you’ll have a curated collection of the moments that made the trip worth it (and the ‘evidence’ to protect yourself if you get a surprise later).