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The Giving Trip: Showing Up for Someone You Love

What if you used your vacation to offer someone else a break? Here's how one woman did that, plus the unexpected results.

I’m breathless as I book our flight. Partly because I do everything in a big rush, but also because—California. We’ve wanted to visit our friends in San Diego for years but never made it to their coast. We pack and drag carry-ons full of swimsuits and sandals through the airport. On the plane, my daughter, who’s almost 13, sparkles with anticipation. We New Yorkers can already feel the sand between our toes.

At baggage claim, two sun-kissed tween-age twins greet us with smiles, hand-lettered signs, and utter excitement to see my wide-eyed travel mate. The kids’ mama, Insa, waits out at the curb in a white SUV. She’s grinning. And for good reason.

Excited to see me? I think so. Like our kids, she and I have been friends for years. But there’s more happening in her heart, and it stirs up joy for me, too. She looks in my eyes and mentally cracks a window—the fresh air flows in, or at least it feels like it. She needs to cut loose from single mom-hood. And I’m here to help her do it. I’ve traveled thousands of miles as a way to help out a friend.

Ways to Help a Friend: It Starts With Saying “Yes”

It all started simply enough, with me throwing out the idea of a spring-break visit to see Insa, and her texting back that our dates worked with her family’s schedule. As plans took form, we hopped on the phone one day, and she made a brave request.

“Would you be okay with me going to Seattle for a few days while you’re here?” she asked, explaining that an old friend, en route to the Pacific Northwest on a sailing trip around the world, would stop for a rest in Puget Sound around the time of our visit.

Would you be okay with me going to Seattle for a few days while you’re here, my friend asked me. She needed the time away. Of course, I said yes.

“Yes,” I said, immediately onboard. I mean, what’s a gal pal if she can’t back you up while you rendezvous with a sailor?

A Time for Generosity, Reciprocity

“For me, time away is an absolute gift,” says Insa. “It was going to be the first time for me since I had kids—that I had no kids,” she says of the Seattle getaway. The boatman was actually a treasured friend from graduate school whom she’d been dying to see for a while.

To friends like me, Insa Simon-Graham is a role model and an absolute pro of a single mom. But to her clients she’s a crackerjack holistic executive and life coach. She built her mobile company Coach on Walkabout, so she could travel, work and worldschool—an educational concept where kids learn through travel and cultural exposure—on the go. She never stops going. Her superpower is helping people live their best lives, and do their best work, without losing themselves. Now she was making room in her life for her.

I trust and appreciate my friend as a listener, an advisor, a reliable doer. Our children met as grade-schoolers when hers, now 12, discovered mine pumping her legs on a tree swing in a raspberry-flecked forest somewhere. From that storybook setting, a magical bond grew. When we are together, I feel like family lines blur. I think I could ask her for almost anything, and felt glad she knew I’d jump to be there for her. 

I stood there and considered the kid-sitting, laundry-doing vacation I’d agreed to. Stupid, right?

In San Diego, Insa showed us a wonderful first weekend of beach fun and barbeque. Then she handed me the house and car keys and took off according to plan. I stood there, American Gothic pitchfork in hand, and considered the kid-sitting, laundry-doing vacation I’d agreed to. Stupid, right? I saw myself sweeping sand from her vehicle and shrilly begging her kids, alongside mine, to shut down the iPhones . . . okay, I can do this. 

Traveling to Support a Friend: Servitude’s Perks

I inhaled the ocean breeze and let myself freak out. Then I considered the flip side. She’d left a full fridge and scheduled the housekeepers for later that week. I’d snagged seven days with her awesome children, whom I love like my own, and for my daughter, two kind and well-trained temp-siblings, a sister and a brother. (We call her the separated-at-birth triplet.) And I was in San Diego! In April! Her neighborhood’s clubhouse has a pool and a hot tub.

“I always enjoy the amenities,” says my friend Marcia, who roadtrips regularly to her son and future daughter-in-law’s place in Saratoga Springs, New York, to care for Pickles, their Garfield of a cat, while they’re away. The community where the kids live has pickleball courts and a pool, and their new apartment none of the clutter or weekend chores of the house Marcia and spouse have owned for 34 years.

I was in San Diego! In April! Her neighborhood’s clubhouse has a pool and a hot tub.

“I read more, I sleep better, and I bond with the kids,” she offers as reasons why she enjoys helping out, even though a cat allergy limits her to treat-giving and photo-taking. (Her husband offers grandcat Pickles plenty of cuddles.)

Having cared for pets for friends as well, I agree it’s a great sort of helping-hand getaway—often with free lodging. Other occasions to consider volunteering as a support traveler? A second-child babymoon, a gnarly breakup (bartender in the house!), or a mobility-limiting injury.

The Undeniable Upside of Traveling to Support a Friend

Here’s what actually happened during my spring break. I joined my NYC zoom yoga class from Insa’s sunny patio while my brood sparred and cleared breakfast dishes inside. I rode the coasters with them at SeaWorld like I was a teen again. I came to terms, once and for all, with my inability to spawn multiples. One’s a charm!

At least one evening, I lounged on the terrace, taking in the resort-caliber view and drinking a spiked seltzer while the “triplets” cuddled up inside. “Sometimes it’s easier to take care of your own kids if you have other children around,” Insa says, reminding me that my daughter, forced by her vacay siblings to take her turn loading the dishwasher and resplendent with all new hair products, hardly needed any parenting at all.

The week was a success, totally worth the beach read and Swedish massage it cost me.

From Seattle, we got regular updates laced with mischief and gratitude. Insa had taken her older daughter along and dropped her to visit with a friend. With the sailor and a girlfriend who showed up, she jetted around on electric scooters and inhaled fancy sushi. “It felt like empty-nest shock therapy,” Insa says, “but it was really relaxing and fun.” It takes a village for a responsible mother to get some real time off.

I think what Insa and I both got out of the deal was the satisfaction of giving and receiving heartfelt care in this day when we’re so stretched that spontaneity, and saying yes, can feel out of the question. The Mom Swap week was a success, totally worth the beach read and Swedish massage it cost me. And don’t forget, one good turn deserves another. The next triplet fun-fest, with the other mom in charge, is already in the planning.

By Carole Braden

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