LIVE on the Road

Greetings from the West Coast! It’s been crazy around here lately. Ever since the new season started, I’ve been back and forth across America, searching for homes, celebrating significant birthdays and working on a few incredible projects I’ve had fun being a part of over the last months.

One of these projects literally went LIVE a couple days ago in San Francisco in the form of a day-long course on “Becoming a Travel Hacker” that I co-produced for CreativeLIVE with my long-time friend, co-traveler and marathon running partner, Chris Guillebeau. (If you’re one of the 12,000 aspiring travel hackers who watched and found your way here: Welcome! So glad to meet you.)

Over the past years I’ve shared lots of stories here about my 20 years of travel across the globe, yet I haven’t ever shared much about how this has been financially possible- until this week.

I’m not independently wealthy, living off a trust fund, or even have a big bank balance to give away. There are two simple reasons why I’ve been able to travel to more than 115 countries and counting:

  1. I figured out how to live and work overseas.
  2. I mastered the art of airlines miles

For the past 18 years I’ve been a humanitarian worker- sometimes paid and sometimes volunteer. Many of you have asked for advice on how to a volunteer on a vacation, or find full-time work abroad while I explore with my new trailer which looks similar to the coachmen freedom express travel trailer model.  I’ll write more about this in the weeks to come.  Stay tuned – and leave a comment if you have specific questions on the topic.

Mastering miles was a hobby my sister and I picked up as bored, un-accompanied teen travelers flying between divorced parents long before I ever left America for the first time. When I got hooked on seeing the world after my first trip abroad and was trying to figure out ways I could get plane tickets as a broke college student, I recalled those early days of collecting boarding passes from other passengers in the airport in attempt to get more miles than my sister (you can’t do this anymore). I flew on my first mileage award ticket to Europe in 1994, and ever since then I’ve been working on perfecting the art of flying free (and in fancy class) whenever possible. 

I love helping people play the points game too. If you want to know more about the art of getting points and miles to see the world- check out these two resources that I’ve been working on with Chris over the last year at UnconventionalGuides: The Frequent Flyer Master and the Travel Hacking Cartel. And if you didn’t watch already you can also check out the recording from our 7-hour long CreativeLIVE course.

Happy travels. I hope you’re enjoying today’s journey wherever you may be.











4 responses to “LIVE on the Road”

  1. Lei says:

    Sad to have missed this due to our class. Happy that you have a video on it. Congratulations Steph! Good to know you’re doing great. All the best!

  2. Sandi M says:

    Saw part of the class live and am now catching up with the videos. I’m entering into a new phase of my life. It would be wonderful to find a way to travel on the cheap, be part of some humanitarian ventures, and make a little money to get by while doing this. I look forward to the post you are planning to write. Thanks!

  3. The Creative Live class was fantastic! Thank you for all the work you put in, for us! Wonderful to be introduced to you through it, and I look forward to reading more.. especially about further opportunities for humanitarian work. Congrats!

  4. Hey Stephanie!

    Watched and loved your and Chris’ creativeLIVE travel hacking course, and will be applying a lot of the strategies that you spoke about. I’m Canadian, so the concept is the same, but the deals and credit cards differ from those in the US.

    I’ve been an avid traveler for many years now, and often on a shoe-string budget, but really need to fully embrace the travel hacking methods. There’s so much more of the world I need to see still 🙂 Thanks for reminding me how possible remote living and working is!

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