Bad Girl, Good Business

The 100 Years Club Installment #30: HoboBougie

Reading Time: 4 minutes

“Hobo” is a word we don’t hear much anymore.

(It is, however, a handbag style.)

The technical definition (according to Wikipedia, the source of all truths) is someone who  “travels and is willing to work.” By contrast, “a tramp travels, but avoids work if possible; a bum neither travels nor works.”

The new moniker for people who live and work on the road is “digital nomad.” Although technology is a big part of my travel life, it doesn’t always define it. And “nomad” implies wandering through the desert. But I often leave the desert to do my wandering.

Now that I’m done being all professorial about monikers for roamers, let’s talk about what I actually do when I hit the road.

Perhaps it can serve as a guidepost for other people >50 (and younger, of course) who are no longer tied down by work schedules, school calendars, and daily responsibilities for kids, spouses, and parents.

You may have heard of “Eat, Pray, Love.” I suppose I do all of those three things. But when the book was published in 2006, the concept of a single woman hitting the road was fairly novel.

I left Arizona about a week ago, and although my adventures didn’t involve an ashram or a hot Italian lover, I:

  1. Survived a tornado warning in Philadelphia, getting drenched and windblown on a short walk across Rittenhouse Square
  2. Took a relaxing and beautiful drive through Amish country, marveling at the cows and fields. Sometimes the simple things are the most powerful
  3. Rode roller coasters (including a water coaster, where I hung off the front of an inflatable mat). Despite the occasional panic and nausea waves, I was committed to modeling fearlessness for my seven-year-old granddaughter and her five-year-old brother. (I also drank a chocolate martini after they left. When in Hershey….)
  4. Fulfilled my NY flagel craving and burned off the calories with an intense barre class
  5. Hid out in the woods — knitting, reading, and binge-watching series (“The Offer” and “Painkiller,” to be precise)
  6. Worked, wrote, and had a few ZOOMs (because I’m a hobo and not a tramp or bum). Committed to launching a podcast this year and made progress on the reboot of my travel website (which I first launched in 2017, when remote work was still a novelty)
  7. Rocked out at a fundraiser for the Retreat at Stephen Talkhouse

And, of course, I wrote this post.

I still have a full two weeks to go before this summer excursion is over, and I return to the adult equivalent of the “back to school” season. However, I have no intention of sitting at the same desk every day. And although I learn from all the people around me, I no longer have to follow the rules of authority figures or serve detention for bad behavior (which I never did when I was a student because I was really good at discretely circumventing rules.)

In fact, I’m already planning my September road trip, and I even mailed my passport for renewal before I left Arizona.

This Hobobougie lifestyle agrees with me.

The bougie part simply refers to the creature comforts I sometimes enjoy while on the road. But it’s all about the simple and meaningful things.

I find myself being more:

  • Spontaneous
  • Fearless
  • Curious (which includes reading about the history of the places I visit or the real backstories behind Netflix series)
  • Chatty (because talking to strangers can lead to amazing things!)
  • Productive (being super-efficient with my work time so I can enjoy my playtime)
  • Grateful for the little moments in life and the world around me

As of this writing, I have 11,869 days to go until my 100th birthday. (See below for how I figured that out.)

Assuming I’ll be traveling for about a quarter of them, that’s a whole lot of wandering and ruminating!

If I had to come up with my own equivalent of “Eat, Pray, Love,” it would probably be “Experience, Connect, Give.” It may not be turned into a major film, but it can be pretty entertaining and gratifying.

Let’s celebrate the new >50 hobos and give new meaning to the word!

Pack your bag with these fun facts!

BGGB.OkeyDokey-fred Where the word “hobo” came from.

Hobos even had their own conferences and media outlets.

BGGB_ShakingHands It’s a fact. We’re more likely to talk to strangers when traveling.
BGGB_Thumbs-Down-fred Don’t overpack! I am very proud that I didn’t overdo the shoes this time.
BGGB_Pointer Calculating time between dates (for those of you who like to plan)!





  1. Nancy! It’s always wonderful to get on the road, see new things, jog your brain into a different direction. Thanks for sharing your strength and your delight in GOING ON THE ROAD, Beth

  2. I guess I’ve been a hobo (without as much go) for a couple of decades. I definitely intend to inject more travel into my freelance life!

  3. Love your positive, uplifting attitude! You caused me to look at my own accomplishments this summer, most quite modest. But when you put them all together, it feels like something more somehow. Thank you for that!

  4. “Experience, Connect and Give” will be infinitely better than Eat, Pray Love. I’m probably in the minority, but I really didn’t like that film! The idea of having to leave to ‘find’ oneself does not sit well with me!
    Lovely post, Nancy! Here’s to modern hobo-ing!


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