8 Rule-Bending Travel Hacks That Help You Fly Like a Boss A newly nomadic entrepreneur shares his tips to be more comfortable without spending that much more.

By Andrew Medal Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


I love bending rules. I'm the type of person that seeks creative ways to do new things. Recently, I packed up all of my stuff in storage and have been traveling to different destinations two to three times a month. In the past four months I have gone to Playa Del Carmen, Cozumel, Austin, Boston, New York, Las Vegas, San Francisco, Costa Rica, Phuket and Bangkok, Thailand, and Hong Kong. I have many more trips planned (including a speaking engagement in Barcelona!).

I'm officially a nomadic entrepreneur. Needless to say, I'm flying all of the time. I've learned tons of travel hacks, and use them while booking flights, flying and once I land at my destination.

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Here's a short list I came up with while flying to Thailand:

1. First Class/Priority

As you're walking through security, the first class/priority lines are always much faster. No matter what ticket you have, make sure to use those lines. More often than not, they just let you pass, and if they stop you, tell security you're planning on upgrading at the terminal (which in my case is always the truth).

2. Upgrade

I've had much better experience upgrading at the terminal. By the time you're at the terminal it should be getting close to flight, and I've been able to get better prices because the attendants have a better idea of how much availability there is. The risk is that you get there and the flight is totally full. Even if this is the case, they typically accommodate a better seat, as agents now know you were willing to pay more for the upgrade and they couldn't fulfill that request.

3. Armrest war

Since the beginning of human flight, the armrest war has raged. I can picture Orville and Wilbur Wright fighting over armrest position at Kitty Hawk. Whether window, aisle or middle, there's always a need to secure your position on the armrest early on.

If you are the first in your row, you can lock down the vantage point. That is rarely the case in my experience, however, and the trick if you are facing early defeat is to be the first person to recline your chair. This reclined angle will allow you to supersede any arm position said opponent may have had early on, and allow you to claim victory. You're welcome.

4. Charge your phone faster

Make sure your phone is in airplane mode to expedite the charge time. This is not just a travel hack, but a useful life hack. It works well. My phone charges 20 percent faster. I know because I timed it both ways.

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5. Hydrate

It's easy to become dehydrated while flying. Plus, the stale circulated air and close confines can make you more susceptible to illness. I drink tons of water when I fly, which helps me stay hydrated and keeps my immune system strong. Rather than drink small cups of water, I always ask for the full bottle. I've never been turned down, and rather than pay a premium while in the airport for the water, I put the cost on the airline.

6. Musical chairs

Depending on the airline, your flight and other variables, you may be able to move around the plane once in flight. For example, as I'm writing this, I am flying to Thailand. When I got to the terminal to upgrade, an agent told me the flight was full and I couldn't pay for an upgrade. I was given an exit row seat with double the leg room, which was a nice courtesy. So I stayed there the first part of the flight and slept. Then, upon waking, I walked to business class, found a pod that was clearly empty and sat down to write this article. I'll spend the remainder of the flight here, and will go back to my seat when we are close to landing.

7. Make friends

I always make friends with at least one flight attendant. Having an ally in flight is a major advantage. This ally can help with your musical seat objective, can provide you refreshments, extra snacks or simply make your flight more peaceful.

For example, when I traveled to London on Virgin Air I made friends with all of the flight attendants serving the first class pods (where I was sitting that trip). The benefits were that they gave me extra food, provided me with extra snacks, offered free premium alcohol (which I politely declined because I don't drink) and allowed us to move our seats to a better pod at no cost.

8. Restrooms

Always use the business and first class restrooms. They are kept cleaner with better materials. For example, I'm flying Cathay Pacific currently while writing this article, and general seating restrooms have one-ply toilet paper, while business class has two-ply. Your behind deserves the best.

Push the boundaries in life. Ask for what you want. If you don't get it, ask someone else. Be persistent. Be creative in your thought process, and be the person that bends the rules. Those rules are targets for people who think outside the box to break. Oh, and for the record, I was kicked out of my comfy business pod. But there was less than an hour left on my flight, and I didn't get in trouble. I spent about six hours enjoying myself, writing and reaping the benefits of a more spacious airline seat.

Related: 6 Tips on How to Get Work Done While Traveling

Plus, I'm going to make a complaint because I wanted to upgrade anyway, and was told there wasn't any room, but I debunked that myth by sitting in a seat that was, in fact, empty. I'll probably get a free upgrade on my return flight by explaining this situation. Win-win.

What are your best travel hacks?