Miles and Points Make Jason’s Goal of Traveling Full Time a Reality!
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Welcome to the next installment of our Reader Success Series where Million Mile Secrets Readers share how they booked a trip with miles & points to get Big Travel with Small Money! This interview has been edited for content and clarity.
Jason is our newest reader success story to show folks it’s possible to travel without spending a lot of money. If you would like to be inspired by more stories like this one, take a second to subscribe to our newsletter!
What’s your name and how long have you been involved in the miles & points hobby?
To start, the only credit card I had was the Southwest Rapid Rewards® Plus Credit Card. I put every purchase I made on it and got a few free flights a year. I did that for the first 3 years I was in the hobby. I never thought much about it and didn’t realize I was only scratching the surface of the miles and points hobby.
I really stepped up my travels in the last 3 years. My friends and family took notice of my travels and needed to know how I was pulling this off. That’s how I got into coaching others about travel rewards.
Fast forward to now, and I have been coaching others for ~2 years. It’s my favorite thing in the world. Helping others learn about travel rewards brings me so much joy, it’s almost surreal!
What was the goal of your trip?
My experience is a bit different than most. Since April 2017, I have been traveling full time and living the digital nomad life. I have been using miles and points every step of the way to cover my travel expenses, even paying rent with points on more than one occasion.
The purpose of my trip was to see more of the world than I could with a “normal” job. I have always worked in digital marketing from home, so the next natural step for me was to quit my job, become a full-time entrepreneur, and of course, travel the world!
Since April 2017 I have explored 18 countries and 4 continents. Some of my favorite destinations included Canggu, the Perhentian Islands in Malaysia, Barcelona, and Ho Chi Minh City.
How long did it take for you to collect the miles and points needed for your trip?
I applied for a number of different credit cards in the 12 months leading up to my full-time travels. Honestly, I had way more miles and points than I needed, and I still do! It has been more of a hobby than a need at this point. Most of my spending falls under “travel/dining” or “business expenses” so I’m always using credit cards to maximize my rewards.
Which points did you save to take your trip?
My strategy is to try and always have a stash of miles from American Airlines, United Airlines, Delta, and Alaska Airlines! I feel this gives me access to the top 3 US carriers as well as 3 airline alliances that are the most important for my international travels (oneworld, Star Alliance, and SkyTeam).
Of course, keeping flexible points such as Chase Ultimate Rewards, AMEX Membership Rewards, Starwood, and Citi ThankYou makes booking tickets much easier. I’m all about keeping everything in my life as flexible as possible!
I like transferring Chase Ultimate Rewards points to travel partners like United Airlines and Hyatt. I like to use AMEX Membership rewards to book flights on airline partners like Emirates and Etihad. And with the Starwood and Marriott merger, there’s access to even more airline transfer partners!
Which cards would you recommend to open for a trip like yours?
This is the hardest question anyone has ever asked me! Honestly, with the great offers on many of the Chase small business cards right now, I would try to get all the Chase cards that earn Ultimate Rewards points. But I’ve also included a few cards from other banks, and some cards that I might choose if I could not qualify for a business credit card:
- Chase Sapphire Reserve® or the Chase Sapphire Preferred® Card
- Chase Ink Business Preferred Credit Card
- The Platinum Card® from American Express
- Hilton Honors Aspire Card from American Express or the Hilton Honors American Express Surpass® Card
- Bank of America®️ Premium Rewards®️ credit card or the Capital One® Venture® Rewards Credit Card
The information for the Hilton Surpass card has been collected independently by Million Mile Secrets. The card details on this page have not been reviewed or provided by the card issuer.
How did you search and find the award flights?
Ah yes, my least favorite part. Award Hacker is probably my favorite tool around at the moment. I also use a combination of Google Flights, Expert Flyer, and Seat Guru!
How did you find your hotel accommodations?
I prefer to travel to places for 1 to 3 months at a time, so I don’t stay at a ton of hotels. I usually book Airbnbs or rent apartments from locals. I feel like it’s a much more authentic experience because it’s more like living somewhere permanently. And sometimes, I use flexible points to pay my rent with Airbnb, which is pretty cool.
When I do book hotels, I try to use Hyatt, IHG, or Chase Ultimate Rewards points. And if I do have to pay for a hotel room, I try to look for deals on Hotels.com and Booking.com.
What was the most challenging part about planning your trip? How did you solve it?
Booking international award flights can be a bit tricky sometimes. Especially when you have to call in to make the booking! Also, navigating unfamiliar airline websites, language barriers, and time differences make it more difficult. But it’s all part of the adventure. And when you’re traveling nearly all the time, there’s not much time to complain!
Tools like Google Translate have helped me a lot. And having lots and lots of patience and keeping a smile on my face!
Give us a few recommendations or tips for what to do at your destination. Parks, restaurants, hidden gems, etc.
- Get Scuba certified in Malaysia
- See all the architecture, and enjoying the drinks, wine, and tapas in Barcelona
- Experience the MAGIC of Bali, my favorite place on Earth!
- Visit the Cliffs of Moher in Ireland
- Eat EVERYTHING in Vietnam
- Eat ceviche in Columbia
- Go surfing in Nicaragua
What did you learn about yourself on the trip?
I learned all I need to be happy is warm weather, good surf (warm water only) and good Wi-Fi. I’m still trying to find a place that excels at all 3, but I settle for 2 with a smile.
What would you say to folks looking to plan a similar trip? Or to those who haven’t taken a miles & points trip yet!
If you’re interested in becoming a digital nomad or long-term traveler, just do it! Sure, you’ll have to line up some stuff in your life first, but just book the ticket and take the trip.
I see people stalling their dream trip for years (mostly out of fear) only to see it never become a reality. Traveling and living in another place, even for just a few days, is an amazing experience and teaches you a lot about yourself.
Life is short. Book the ticket. Take the ride! Just book the ticket with miles and points, or pay for it with a card so you can earn even more miles and points!
Want to Share Your Story?
If you’d like to be considered for our reader success story series, please send us a note! We would love to hear about how you travel with miles and points! And if you want to get more stories like this one delivered straight to your inbox, please sign-up for our email list!
Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)