You know the adage “if it sounds too good to be true, it probably is”?

That doesn’t apply to today’s post.

I’m going to share with you a process that I used last year to increase my enjoyment of life by like, thiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiissssss much. It enabled me to do a boatload of what makes me super happy in life – travel – more than I ever thought I’d be able to. And I did it for free!

What I learned to do, was Travel Winning.

What is Travel Winning? Travel Winning is the art of collecting frequent flyer miles and/or travel points by taking advantage of special credit card offers.

On the interwebs this process is commonly referred to as “Travel Hacking”. But I’ve found that, in explaining the process to people, the term “hacking” turns them off. It sounds creepy, nefarious and tedious. So I decided to change the term to Travel Winning, since that’s really what we’re doing here: getting a big W in life.

Here is what Travel Winning allowed me to do last year:

• Take a round-trip flight to L.A. for a retreat I was speaking at (April).
• Fly round-trip to my hometown of San Luis Obispo, CA for a buddy’s wedding (May).
• Fly from NYC to Sao Paulo, Brazil to visit a client/friend, fly from there to Reno, NV for my cousin’s wedding, then fly back to NYC after spending time with my family at Lake Tahoe (June).
• Fly one-way to San Luis Obispo to start my epic summer road trip (July)!
• Buy a plane ticket for a dear friend who greatly needed a vacation (August).
• Fly one-way from San Diego to NYC at the end of my road trip (September).
• Fly home and back, and spend two weeks with family + friends for the holidays (December)
• AND DO ALL OF THAT SHIZZ FOR FREEEEEEEEEE!

By sharing the above I’m not trying to shout from the top of a mountain, “LOOK AT HOW AWESOME MY LIFE IS!” And if it comes across as such, that’s a risk I’m willing to take. I simply want to give you as much evidence as possible to show you that, if travel is something you want more of in your life, you can absolutely have it.

Which brings me back to this free guide. While it’s possible to earn as many miles and take as many trips as I did last year by Travel Winning, that’s not where most people will start. It took me a fair amount of trial and error to learn how to do this effectively, and I made my fair share of boneheaded mistakes along the way. My goal with the guide is not to make you an expert but to give you enough information to, at minimum, earn yourself one free flight this year.  Once you get the hang of it, you can take it as far as you want!

With this guide you’ll learn more about what Travel Winning is, why it’s awesome and how it actually works. I answer common questions such as “Won’t opening/closing credit cards hurt my credit score?” and “What about the annual fees?” that keep people from getting started. You’ll also find a detailed checklist so you don’t skip any important steps as you go through the process for the first time of earning yourself a free flight!

Why am I doing this? Why create this guide in the first place? Because when I look back on the past year and reflect on how many amazing people I was able to meet, friends I was able to see and experiences I was able to have, I realize that very little of it would have been possible without the benefits of Travel Winning. And I want you guys to have the same opportunity!!! If I can help remove the obstacle (money) that keeps many people from pursuing their passion for travel, then that’s a big W for me, personally. Giving: it gives you the high of drugs but without the hangover!

Download the Travel Winning Guide!

I would love to know what you think of the guide and welcome any/all feedback you have. Share your success stories too, so I can know how it’s having an impact on your life.

Thank you, as always, for trusting me with your eyeballs and time. Getting to do what I do every day is a gift, and you all play a huge part in making that possible.

Love,
Former Vice President Al Gare