The 7 Deadly Sins of Travel Hacking

seven deadly sins painting-558483_1920
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The travel rewards world is filled with amazing experiences. But it can also be full of pitfalls that get in the way of maximizing the value of your miles and points. Everyone is familiar with the Seven Deadly Sins that were first quoted by Pope Gregory I and made into the movie Se7en starring Brad Pitt. But have you thought about how these sins are affecting your miles and points strategy?

Pride (aka Know-it-all)

With Pride, you’ll experience an unrealistic sense of your accomplishments. In the travel hacking world, remember that you’re never too experienced or knowledgeable to know it all.

Continue attending conferences like FTU and Chicago Seminars to network with other travelers and hear speakers present on their area of expertise. I go to these conferences as often as I can and always come back with more new friends and tips expected.

FTU Seattle 2019 Sharps Roast House group dinner
Group dinner with new friends at Seattle FTU in March 2019.

Greed (aka Unwilling to share)

The hotels, airlines, and banks designate some of their best minds towards optimizing their loyalty programs. None of us can counter this expertise alone. Our communities work by sharing information with others.

Many people will say that sharing tips and tricks “kills” the opportunity. While that may be true to a small degree, what really kills deals is when people get greedy and abuse the rules to the point that companies have to act.

Be willing to share secrets with your fellow travel hackers. By bringing others into the deal, you can build friendships with others that share the same interests. And you never know when your goodwill will result in someone else sharing an awesome tip with you the next time around.

Lust (aka Obsessed with status)

There are plenty of things in this world that we all want. But it can become an unhealthy obsession that can interfere with your enjoyment of “normal” travel experiences.

The insatiable desire to earn top-tier status can blind you to the other joys in life along the way.

In many cases, the elite status and benefits offered by credit cards are significantly better than top-tier status when you factor in the time and money involved in achieving that status.

Don’t get me wrong. Elite status can be worth it in the right situations. Just keep in mind what you’re giving up (in time and money) when you’re doing yet another mileage or mattress run to achieve that elite status.

best credit card offers - Kimpton Sir Francis Drake 2016-06 Starlight Suite
Upgraded to the Sir Francis Drake Starlight Suite thanks to Kimpton Inner Circle status.

Envy (aka FOMO)

In today’s age of social media, it is impossible to not be envious of someone’s flight, hotel, or experience. I see pictures of friends flying First Class, staying at five star hotels, and doing cool things like hiking to Machu Piccu, snapping a selfie with a tiger, or enjoying a 3-star Michelin meal.

We all need to stop the envy.

With the power of miles and points, any of these experiences can be ours. Every single one of us could make any of these trips happen. Simply pick the flight, hotel, or experience that you are envious of, then make a plan to earn the rewards to do it yourself.

It is possible! If you need help, book a free 30-minute consult with me or take my free seven-day email course.

Gluttony (aka Earn but never use)

As fun as it is to earn miles and points, you need to actually use them. Nobody is impressed if you have 10 million miles sitting in your account.

Those miles are becoming less valuable by the minute. Airlines, hotels, and banks devalue their loyalty programs on a regular basis.

You need to earn and burn. Pick a destination, figure out how you want to fly, and where you want to stay, then focus on those rewards until you have enough saved up. Book that vacation, then start earning and saving towards the next one.

American Airlines First Class Pre-Boarding Drink
You know you want to sit in First Class and enjoy a long flight. Put them miles to use!

Anger (aka Overly critical)

Traveling is a lot of fun, until it isn’t. Flights get delayed or canceled. Customer service agents are unhelpful or unresponsive. And airport security lines are getting longer by the minute.

Whenever something goes wrong, just remember that no plans go 100% according to plan. Stay flexible and treat people with kindness even when your blood is boiling.

While everyone else is freaking out, being calm and flashing a smile will work wonders. Try alternative channels of communication to resolve the issue.

There have been plenty of times where I’ve been in line to talk with someone, while simultaneously Tweeting the brand and waiting on hold with customer service. When I got stuck in Atlanta coming back from the Cayman Islands, Rene from Rene’s Points suggested that I speak with Delta’s customer service in another country. I literally had someone on the line within two minutes of calling via Skype.

Delta Atlanta waiting to talk to agent
Stuck in line waiting to talk to a Delta agent.

Sloth (aka Unorganized)

If you’re going to earn miles and points, you need to have a good system to keep track of them. It is far too easy to lose track of rewards that could have been used instead of cash or to have them expire without realizing it.

To track my miles and points, I’ve been using AwardWallet for years. They send me a weekly email alerting me to changes in my balance and have an awesome mobile app so I can check my accounts any time of the day or night. Use my referral link to get the premium version of AwardWallet free for six months.

For those of us who dabble in credit cards, you have to be even more cautious. It is so easy to harm your credit if you aren’t paying attention. That damage can last for years and affect your ability to get a mortgage, buy a car, or even get a job.

Many services and banks offer free credit scores and reports via websites and apps. I recommend checking on your credit at least once a quarter to ensure that everything is ok.

The Bald Thoughts

When you’re involved in the miles and points world, it pays to follow some simple concepts. By avoiding the Seven Deadly Sins of travel hacking you’ll enjoy better experiences and have great vacations that you can share with your friends and family.

Of the Seven Deadly Sins, I’m most guilty of envy. I have so many friends in the travel world that I follow on social media that it’s hard to not experience FOMO (fear of missing out). But then I realize that I can earn just as many miles and points as they can so I, too, can take awesome vacations.

Now, it’s just a matter of deciding where to go next…

Which of the Seven Deadly Sins of Travel Hacking are you most guilty of? How do you conquer them? Let us know in the comment section below.

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  1. This is a MUST read! Great conversation points, Lee. Travel. Miles. Points. Status. And so much more. If our hobby intrigues you, this is a #tidbit + +

  2. This is great advice all around. I am not as heavily into the points game as many people are, but I can still relate to some of the sins. I am going to use this as a checklist to keep me in line.

    • Thanks, Jeff. As you’re getting more into rewards, these lessons will help keep you on track. As a beginner, it pays to have a goal for your rewards so you can work towards a specific vacation. This will keep you motivated and help your spouse understand why you’re doing things a certain way. Let me know if you have any questions!

  3. Your referral link I went to directly to award wallet shows it costs $30 immediately. You have to put in a credit card and it shows you will be charged $30. Nothing about 6 months for free anywhere.


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