I Travelled with My Toddler Cross-Country While Launching a Business from My Trunk

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By Jocelyn Newman

We decided last summer that we were ready for a leap of faith, a new chapter, and a little bit of crazy. We gave up our San Francisco apartment, sold and donated nearly all our possessions, and set off to travel and enjoy more time as a family and in the outdoors. 

The timing wasn’t exactly “perfect,” if there’s such a thing as perfect timing. We had a one-and-a-half-year-old with a blossoming personality and a strong desire to leverage his new walking, running, and climbing skills. I had just launched a new baby and toddler clothing line called First Peak, inspired by our own adventures and travel outdoors.

Jocelyn travelling with her toddler and pup

While my husband and I are privileged to have about ten years of experience working in tech, a highly remote-friendly industry, we both had to give up our nine-to-fives to make this a reality. 

Perhaps fueled by years of pent-up pandemic energy or crazed by the exhaustion of raising a toddler, we felt bold, and we dove in. We kicked off our journey with a cross-country road trip from the Bay Area to New England, leaving a few sentimental items in the smallest storage unit we could rent and packing our car with everything else we owned.

Our toddler and dog shared the backseat, and about 40% of our trunk was devoted to all my First Peak inventory (I’m lucky that baby clothes are small). 

Jocelyn travelling with her toddler

In our near-month of driving, we spent most of every day outside, enjoying the long summer days and warm, gushing waterways. We hiked each morning, drove a long stretch during naptime, and broke up the afternoon with pit stops, parks, viewpoints, and more driving.

We learned the most efficient ways to travel, load and unload a car while entertaining a toddler and dog. We became experts in the “goblin meal,” throwing together a hodgepodge of leftovers and snacks to compose something nutritious and kid-friendly. We were grateful for the hospitality of many friends and family members who offered us cozy beds and hot showers. 

Perhaps the most memorable part of the journey was one we didn’t plan: at some point in western Montana, I had the idea to post about our trip to a Facebook group of outdoorsy moms.

I shared that we were travelling across the country with a trunk full of sustainable adventurewear for babies and toddlers from a growing, mom-owned business that had just launched.

I asked for recommendations for hikes but also if anyone would be interested in meeting up, trying the clothes with their kids, giving feedback, and taking a few photos. 

The response blew me away. Over the course of our drive, we met about 20 families, and all had the opportunity to try First Peak. This fledgling business that I had dreamt of for so long was suddenly reaching communities that I was getting to know firsthand.

At each stop, we’d ask the locals to recommend a great hike, and we’d arrive and pop the trunk. Families could touch, react, and pick out their favourite First Peak items, and we found wonderful, hidden hikes we’d never have discovered otherwise. Our son had a chance to play with (and frankly, quietly watch) many new kids, and we were able to meet and spend afternoons with like-minded parents.

At the end of each hike, most families would purchase a few additional items. Many would offer to post and share with friends. A special few we’ll keep in touch with many trips and adventures to come.

Three and a half weeks later, upon arriving to see my in-laws in Boston, there was certainly a sigh of relief: the relief of staying in the same place for more than three nights, the relief of fully unpacking (and washing) the car; the relief of home-cooked meals that someone else was cooking. But we also mourned the end of that segment of our adventure, and itched for the next leg. 

We went into our trip expecting challenges, and we certainly encountered them: flat tires, surprise thunderstorms, multiple lost baby shoes. But we also realized how normal, safe, and special it could feel to settle into family time in nature every day.

In many ways, our adventure further inspired and fueled my business, and the clothes themselves enabled more adventuring — my son wore First Peak each day and having clothes purpose-built to dry fast, block the sun, and resist odour made a world of difference when a washing machine was a rare amenity.

We’re still figuring out what’s next, but that feels consistent with how the past few months have gone. At the very least, we’ll remain bold, optimistic, and adventurous and remember that community can be built and enjoyed even when on the move. 


Jocelyn Newman is a mom, entrepreneur, and adventure traveller. She’s the founder of First Peak (www.firstpeak.co; @firstpeakbaby), a line of sustainable adventurewear for babies and toddlers, inspired by her travel adventures with her own son. All First Peak clothes are designed and manufactured in California using eco-friendly fabrics that are purpose-built to handle mess, moisture, and mayhem. 

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