Months ago, I announced that I wanted to help four readers plan a trip from start to finish as part of a case study project for this website. While I haven’t talked about this in a long time, it’s because I’ve been busy making it happen.

After going through 450 applications and countless follow-up calls, today I’d like to introduce you to the people I’ve been working with to help make their dream trip a reality.

People often say to me; “Well, of course you can travel. You have experience and it’s easy for you, because you’re a white male from a middle-class background, but my situation is different because (insert reason here) and that’s why I can’t do it.”

I don’t believe travel is something for the few, rich, middle class, or American, which is why I started this program. I’ve taken on these case study participants to highlight that people of varying incomes, ages, backgrounds, and nationalities can travel.

Each one of these case studies represents a different story. From those who want a two-week holiday to those looking to get away for as long as their money lasts, I think there is inspiration for everyone.

My advice is not just for those like me, it’s for everyone — and I want these case studies to inspire you and help show you anything is possible.

So, without further ado, here are the case study participants:


Jianne is 27 years old and lives in the Philippines. She currently works as a Clinical Research Associate and is looking to go away for two weeks early next year. She has limited vacation time each year and has no desire to quit her job so a long term trip isn’t in her plans.

Earning over a thousand dollars per month, Jianne’s challenge is to find ways to cut her expenses. She admits she’s not the best at saving money. In fact, her current spending levels match her monthly income. Moreover, the Philippine Peso isn’t very strong so we need to find a country where her money goes fairly far.

I’ll be helping her increase her travel fund and maximize her short time abroad. In the month we’ve worked together, we’ve tracked her expenses to determine where she can save the most and discussed strengthening the mental link between cutting her spending in order to save more for a trip.

She’s going to post motivational photos of her desired destinations and now has a “trip jar” to save her change in to serve as a constant reminder that spending now means delaying her trip. Plus, it acts as a way to watch her savings grow.

Our current goal? To save $300 a month.


Diane is a 59 year old recent retiree from Toronto who’s on a fixed income with her husband (though she will be traveling alone). Always wanting to go to Australia and New Zealand, she has finally decided it’s time to make it happen. While Diane has some savings, she doesn’t want to tap into too much of it because of her fixed income.

Right now, we are focused on switching her banks to ensure she pays no fees when she goes overseas as well as getting her signed up for a points-earning travel credit card.

Next, we’ll be coming up with a tentative itinerary so we can estimate just how much she’ll need and establish a savings goal.


Jeremy is a recent graduate living in Charleston, SC and holds two jobs: he’s an education interpreter at an aquarium and a zookeeper at a state park. He earns slightly above minimum wage and his student debt and rent payments eat up half his paycheck.

Jeremy has always wanted to travel but ends up spending his travel funds on other things. He has recently realized that there are no tomorrows and decided to make his trip happen. He’s planning a long-term trip and needs to save up enough money to make it happen, though he will work on the road to extend his trip.

Currently, Jeremy is good at not overspending. Besides occasional splurges on dining out, he doesn’t spend much money.

Our goal then is to increase his income by looking at renting his place on Airbnb, becoming a driver with Lyft, and using other sharing economy websites to find extra income.

Additionally, we’re going to get him signed up for a travel rewards credit card to start earning frequent flier miles.

Sander and Jolien

These two are a couple from the Netherlands who are quitting their jobs next year to travel the world, with no definite plans to come home. Money isn’t a terrible issue at the moment as they plan to work into early next year, and already have over 5,000 Euros saved up and are on track to save over 20,000 EUR for their trip.

Just shy of 30, they plan to make it to Australia at some point in their travels for a working holiday visa.

Since they are from Europe, they can’t benefit from any cool travel hacking techniques so we’re going to focus on keeping flight costs low and come up with a budget for their trip.

Despite their strong financial profile, we still need to lower their current expenses and create the mental link between spending and their trip (just like with Jianne) to keep their budget in line.


Over the next couple of months, I’ll be sharing more about the progress of our participants – the successes, the failures, and the lessons learned. I’m incredibly excited about this project in hopes of inspiring others of all walks of life to take the leap and travel more!

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Book Your Trip: Logistical Tips and Tricks

Book Your Flight
Find a cheap flight by using Skyscanner or Momondo. They are my two favorite search engines because they search websites and airlines around the globe so you always know no stone is left unturned.

Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use as they consistently return the cheapest rates for guesthouses and cheap hotels.

Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. I’ve been using World Nomads for ten years. My favorite companies that offer the best service and value are:

  • World Nomads (for everyone below 70)
  • Insure My Trip (for those over 70)
  • Medjet (for additional repatriation coverage)

Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.


25.06.2015 / Interviews / reader stories / success stories
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