Imagine that today is your lucky day. It is just one of those days. Everything is going your way and it almost seems too good to be true. You are in the airport waiting for the flight to your all inclusive beach front resort and you say “what the heck? I’ll ask if they can upgrade my seat because I am feeling lucky.”  You begin your casual stroll to the check-in counter and all of a sudden, pearls of sweat begin rolling down your palms. Am I really about to ask for an upgrade? You think to yourself, as a butterfly flutters through your stomach. And there it is – that feeling – pride. You turn around half way and decide that you’ll just have to settle for what you have. Thank you. It is people like you, that open up the magical world of upgrades – for people like me.

Getting the golden ticket to sit in God’s arms is similar to scoring a suite in a posh hotel, or a better table at your favorite restaurant. Getting the latter free of charge – is absolutely magical. In the last year, I flew business 3 times, and economy comfort plus (via Delta & Air France) 3 times, and I scored a suite at a 5 star hotel in Abu Dhabi (just to name a few). Did I pay for any of these things? No, not a dime.

While I focus primarily on flight upgrades in this post, the majority of these rules can apply to … well, anything.

1. You Have Nothing to Lose. 

First ask yourself: What is the worst that can happen? Then prepare to accept it. Then proceed to improve on the worst. – Dale Carnegie. Let go of your pride, and rid yourself of the burdens that come with your fear. Chances are, you will NEVER see those people again, so what are you embarrassed of ? What’s the worst that can happen? They’ll say no. And hey, that’s alright because you miss all the chances that you don’t take. Pat yourself on the back, you just finished your first practice round.

2. Remember that a person’s name is to that person the sweetest and most important sound in any language. 

Stop what you’re doing and open this link. I will be quoting Dale Carnegie a lot here because the key to life (and more free upgrades) is found in his books – & you don’t even have to read between the lines. Thank me later. Always be kind to the people you are speaking to, especially since you want them to do something for you. If someone has a name tag, always address them by their name. You can even sweeten your opening line by saying “Hi Jane, is it ok if i call you by your first name?” If there is no name tag, well then ask for their name. Now you established friendly and more importantly respectful grounds.  Look, these people are working as real life customer service agents. Can you imagine how many complaints and requests they get throughout the day? If you take the approach that projects, “you work here, you owe this to me, I am the customer” – you are shit out of luck (excuse my French). No one will even attempt to help you, even if they can.

3. Compliment. 

Start a conversation with a simple “Nice watch, wow where did you get it?” or “I love your hair, do you get it done like this for work every day?” 

Sincere compliments are, of course, the best compliments to give. But I get it, sometimes you need to sugar coat it – and thats ok. You just made that persons day – and now he or she will at least try to help you.

4. Know Whom to Ask.

Whenever I book a flight in advance, I always give a quick call to customer service just to get my foot in the door. I call to ask if they can offer me better seats, perhaps seats closer to the front of the plane, a bulkhead seat, or an aisle seat – free of charge of course. This has to be done more than 24 hours before departure – when customer service still has control of your seat. Just because you’re not speaking to someone in person, doesn’t mean you shouldn’t follow steps 1, 2, and 3. As a matter of fact, if you’re a little shy, following steps 1, 2, and 3 should now be a breeze for you. Nothing to be embarrassed of. While on the phone, you can get a good idea whether your flight is full or not (I’ll explain the importance of this later). At the end of the call I always say something along the lines of, “Can you add a note to my name, maybe there will be an upgrade available” . The answer almost always will be no. But I have nothing to lose.

5. Full Flights are Good Flights. 

Airline companies carefully plan by how much they oversell flights. You’d be surprised how many people are no-shows or cancel last minute. I heard this theory before but I didn’t believe it until Air France randomly bumped me up to business class on my flight from Paris to New York City. Many airline companies now use automated systems to upgrade people randomly when a flight is full. I got randomly chosen for upgrade on that flight, but the woman that sat next to me, who also got upgraded, was at the gate early and asked the staff. To her luck it was a full flight and she was upgraded. Moral of the story: just ask.

6. Be REASONable.

Airline employees, restaurant employees, and hotel employees are all people. They all celebrate birthdays, perhaps anniversaries and other events. If you mention that it is your special day for whatever reason, you will gain some heartfelt sympathy. Its a win-win for both parties. If you’re happy, you may leave a good review, recommend to a friend, and most importantly come back. So give a reason … even if there may not be one. Shh.

7. Complain.

Ah, the art of complaining. I hate to say it: aside from complimenting, complaining can increase your chances of getting a complimentary upgrade, almost exponentially. I mean lets face it: you are the consumer, you paid for it – and if “it” is broken, spoiled, dirty, or misrepresented, you should be compensated for it. Sometimes one reason to complain is more serious than another – but who’s to say ? A lone hair on the bathroom floor of your hotel may be a bigger deal to me than to you. That is why complaining works. There are no guidelines to determining what is a valid complaint, and what isn’t. If you can find any reason to complain, do it. On a flight, flight attendants  have little mobility when it comes to changing your seat. If its an empty flight and your TV is broken, they will happily move you within the same cabin- but you will never get moved to a higher cabin by a flight attendant, even if your cabin is full and business/first is empty. You will have to deal with not having a working TV. Dont worry, come home and draft a short email to the airline complaints department – or better yet, give them a call. If you follow steps 1,2, and 3 – you will get some free miles added to your account, a discounted rate for a future flight, or even a credit for your flight. This goes for hotels, and restaurants, and any other place where you are getting serviced.

8. Be Loyal.

With most airline companies, you dont have to pay a dime to sign up for their mileage or loyalty program. Its only a matter of filling in some information and thats it, you’re done. You don’t have to do anything after that, as the miles will pile up on their own as you travel with the same airline. Even if you think you’ll never travel with that airline again, you should still sign up. It’s free and the more the merrier. Being a loyal member of an airline puts you above those that aren’t – especially when it comes to getting an upgrade. Use your frequent flier number when booking your next trip, even if you’re using a third party company like Expedia and look for flights with specific airlines. Sometimes overpaying a reasonable amount to fly with your frequent flier airline, is worth it in the long run.

9. Become a Known Traveler. 

It costs only $85 to become a known traveler. Do you ever wonder how it feels like to not have to stand in a 30 minute line to go through the airport security check. Having the little “TSA PRECHK” line on your boarding pass makes your travel experience more enjoyable and more predictable. You technically don’t even have to be in the airport two hours in advance, you don’t have to take off your shoes, jacket, belt , lap top and 3-1-1 liquids. You breeze through security, and comfortably stroll through a duty free to your gate. Having a TSA PRECHK line on your boarding pass also gives you more credibility. Now, the person you are asking for an upgraded seat sees that, although you may not be a gold or silver frequent flier, you will potentially be flying a lot. So this upgraded seat that they may give you, can make you a loyal customer in the long run. It’s a win – win.

10. Dress to Impress.

 Dress for the upgrade you are trying to get. In other words, you have to fit in. I can’t imagine being in jeans and a button-down on a flight over the Atlantic – but if that’s what everyone in business class is wearing, then you may have better luck by wearing the same thing (and then quietly changing in the bathroom to some cozy sweats and a tee). You might think it’s crazy but a person traveling in a nice pair of slacks and fitted shirt, does not want to sit next to someone in some baggy sweats and ripped converses (and the people working the gate know that). Be comfortable, throw on some of your best accessories and walk the walk, then talk the talk. My two favorite place to shop for the top names in fashion at discounted prices are Designer Daydream & AZ Shades.  Happy Shopping !

11. Upgrade in Disguise.

 As soon as you hear the magic words: “Flight Attendants, boarding is now complete” – look around for empty seats. in a 3-4-3 layout airplane you might be one of the lucky people who sees an empty four seater and jumps on it. This happened to me 3 times last year. And to be honest, I think it is a better deal than business class. A whole row all to myself ? at 5’6″ – I can lay entirely stretched out, with four pillows under my head, four blankets, and four different shows that I can watch simultaneously. This is one of those things that you dont even have to ask the flight attendant for.  Well, you can out of respect. But dont lose any time and move as soon as boarding is complete. It is also a good idea to ask if there are any empty seats available when you’re checking in. Always ask to see if there are any two seaters or four seaters currently empty – and jump on them. Especially on a long-haul flight – so worth it.

12. Wait. 

If you have some extra time and can wait to get on a flight thats two hours after yours, you are more likely to get the golden ticket. If the latter is your case, ask the staff member at the gate if someone is waiting on standby to get on your flight. Express your willingness to take a later flight so that someone who is desperate to fly out, can have your seat. Your chivalrous act will likely be rewarded.

13. Pay for One Upgrade – Not the Other. 

This one worked for me one time. But hey, like I said earlier, whats the worst that can happen ? I paid for an upgraded seat on my Air France flight from New York City to Paris (and then Paris to Kiev). I sat in the Economy Comfort Plus seat on my way there but I haven’t paid for the same seat on the returning flight. When I was returning, I got my boarding pass (which had a regular seat) and I went directly to the customer service counter. Because of our language barrier, and me showing them the proof of purchase on my delta app – somehow it worked out in my favor. They put me into what they thought was my purchased seat, another Economy Comfort Plus seat. But really I only paid for it once.

Bonus: 14. Desperate for a Flight Change? 

Always go to the airline office or desk at the airport. Not the check-in desk, but the actual office. Customer service over the phone has little mobility when it comes to changing flights on the same day. On most airlines, even an emergency situation allows you to get on a later flight, not an earlier one. If you want to take an earlier flight on the same airline, go to your airlines office at the airport, plead your case (it’s ok to lie) – use steps 1,2, and 3 and watch how quickly your ticket gets changed , given that there is room on an earlier flight. This is also a good place to ask if your seats can be upgraded, FYI.