“If It Paid Weekly, I Did It”: My Instagram-Friendly Life On The NZ Road

I couldn’t afford to holiday in Queenstown, but if I cleaned toilets and made coffee, I could pretend to holiday on my days off.

The Cost of a Weeklong Bike Tour

Seven days on a bike tour—from Sioux City to Davenport.

Friday Chatting About Planes, Which Are Miracles, and Airlines, Which Are The Worst

“I dress warmly for planes. I’ve done that ever since the horrific nighttime American Airlines flight I took once where they pumped the AC until it was about 55 degrees in there and then told passengers we were free to pay for blankets.”

The Rise of Traveling Alone

Aspiring to be the kind of person who can take off on a trip somewhere far away and feel comfortable with being alone.

Try Out a New Life By Going on Vacation

Each planned vacation I’ve taken in the past year or so has also felt like an effective way of trying out a new life.

It’s Never Been Easier To Freelance From Abroad

These days any place with an Internet connection can be a workspace, whether it’s in New York or Thailand.

The Cost of a Trip to Africa

In 2014, I took the most expensive and amazing vacation of my life. I visited Namibia, Botswana, Zimbabwe and Zambia with my best friend.

Would You Buy These Plane Tickets Today?

When you’ve been working at paying down your debt, taking out any new debt seems like the biggest possible financial mistake, even if you have every expectation of being able to pay it off at the end of the month, and even if it will save you $100 or more.

The Cost Of First-Ever-Plane-Flight FOMO

My frugal upbringing made me very thrifty. The idea of spending any sort of money on travel, which was an intangible moment rather than a tangible good, was ludicrous.

How Not to Lose All Your Money on a Work Trip in Las Vegas

Each day when the tradeshow ended, we had no choice but to pass through the slots and the lights and the booze as we headed back to our hotel room.