Summer adventuring, Part 4: The One with the Roadtrip

Last summer I almost Scrooge McDuck’d my way out of the chance to travel to Southeast Asia with my friend Tiffany.  That is to say, (if you’re not into ’90s cartoons)  I almost stayed back because I didn’t feel like I could justify spending a chunk of money on smething just for, you know – fun.  If you’re thinking of money purely in terms of dollars and cents ROI, it’s pretty easy to arrive at this conclusion.

Then my coworker Courtney knocked some perspective into me.

“I really can’t imagine going on a trip and in hindsight feeling like it was a waste of time.  But if you don’t go, I can absolutely see you looking back with regret.  So when you have the chance to take a good trip, go! And live it up, because these opportunities just don’t happen everyday!  So, I’d say you should do it, and buy as many awesome souvenirs as you can fit in your bag and have money for, because they’re going to remind you of that one time you went on an amazing trip somewhere, and you’re going to love the reminder.”

You know, it seemed like she had a point.  By and large I’d been saving and investing doggedly for the past decade or so just for the sake of saving…but maybe travel would be a different type of investment, like in memories or experience or something that sounds pretty soft but could actually be important in life. 🙂  (I know this is a really simple lesson from Being a Human 101, but it was still a revelation to me.)  

So I took off for Cambodia, Singapore and Bali, and just like she predicted – I never looked back.  Because sitting here a year later, even though the money’s missing, there’s no sting, no actual feeling of loss from the fact that I’d spent the money to go.  The only thing I feel now, is totally deeply thrilled and grateful to travel to a new part of the world with a great friend, to swim in the Indian Ocean, barter my way through the markets of Phnom Penh, have rooftop drinks alongside a fascinating Brit ex-pat with the best view of a beautiful city.  (Technically city-state, I think, but you get the idea.)   That’s the funny thing about travel, I guess…you seem to feel what it adds to your life much more than what it takes away.  

Not like you can just pay for travel on dreams and wishes and then get back and pay your rent in memories and Cambodian elephant pants: you’re still making a tradeoff, and most of us can’t just go whenever, wherever.    But we’ll get into more of those practical concerns later. 🙂

After last year’s adventure to Asia, it only made sense to Tiffany and me to tack on a New England roadtrip to my next round of East Coast travels. A good-living, really low-budget roadtrip. 

If I had to build a friend from scratch, Tiff would basically be the starting point.  She’s the type of person who can teach you about child participation in international development theory in one minute and then quote friends of rock out to Taylor Swift the next.  The type of person who packs you a picnic lunch as a thank-you for taking her to LAX, who offers to let you live with her and her husband for a bit if things ever get too tight financially.  She’s the type who will drive over at a moment’s notice to comfort you about your break-up and/or irrational fear that you might become permanently, irreversibly unemployable (hypothetically, of course). Tiffany is the type of person that is so accepting, honest, loving and authentic that you feel okay about letting your guard down and be your goofy, receipt-scanning, prancercizing, no-makeup, incessant elephant-pants wearing, full-disclosure self.  And she’ll still be excited to hang out with you.  
Suffice it to say, she’s the type of person that you’re lucky to spend time with.  Given the chance to hop in a car and tour New England with her,  I’m in.  Plus, we’re launching a side venture designing+building jewelry this Fall, and the getaway was the perfect setting for concentrated inspiration and brainstorming time.

So, there we were – The One with the Roadtrip. 

7 days, 6 states, 1,174 miles, and more or less an amalgamation of this:

Sweet potatoes. Scenic roads. Poor cell reception.
Making plans. Farmers markets, Co-ops.
Tiny charming towns. Quoting Friends.
Lots and lots of Google Maps.
Bread and pastries. Moving near always.
Handmade jewels. Blueberries, seafood.
Inspiration gathering. Freshly minted airbnb hosts.
Rivers and ponds. Dining al fresco.
Counting our steps. Soba noodles, Kucicha tea.
Still-forming ideas. Fresh air.
Wildflowers, and more wildflowers—
—and hey, “why not.”

I dropped Tiff off at the Portland, Maine airport, and pored over photos from the past week, before making the solo drive back to Manahttan.  It was one of those weird times when you’re sitting in public, smiling like an idiot, about a split second away from just exclaiming to the random people walking by that “how great is life!?!”  Surely you’ve been there?

If I wanted to evaluate things purely pragmatically, the getaway with Tiff trip cost money I didn’t have to to spend, and added one more week to the resume gap I’m creating with this time off.  But when I look back, I’m not going to think about any of that. I’m going to remember what we saw, and ate, when we laughed, what we said, and I’m gonna think – “God, is life good.”

Next time you’re on the fence deciding whether to stay put or travel, I hope you take the trip – whether it’s Asia, a few states, or just visiting something new in the town next door.  Seems doubtful you’ll regret it. 🙂

Madison Square Park, NYC
Brooklyn Bridge by rental car


New Haven, CT

Stockbridge, MA

New Haven, CT and. Stockbridge, MA
Plainfield, VT
Marshfield, VT
Waterbury, VT
Groton, VT

Newmarket, NH


Kennebunkport, ME

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