Two years ago, during a solo trip to Portugal, I booked a spot on a group tour to the coast. A national park, wine country, castle ruins, and a beautiful seaside town were all listed on the booking. As were seven other people.
Until everyone canceled. Every single person.
Manuel, my guide, met me outside a shop in Lisbon the morning of the tour. He was apologetic but optimistic when he told me the news: “It’s just us today, and the tour company will refund you if you’d rather not have a private tour. I’m okay with continuing if you are.”
Let me be honest: There was a time in my life when the thought of an eight-hour, one-on-one tour would have made me slink into the bushes like that Homer Simpson gif.
This was not that time—it was somewhere further along, a stop on a long growth arc where I was yes-and-ing everything that made me uncomfortable. Boy, did the idea of nonstop conversation with this stranger—sorry, not a stranger, Manuel—make me uncomfortable.
So I got in the van.
This ended up being the beginning of a perfect day. No, we didn’t fall in love, as the followers on my Close Friends story hypothesized. (Manuel is married with a beautiful family and is the president of his HOA. Come on now.) But in terms of life skills, the day taught me something I wouldn't have learned from a quote on Pinterest or a listicle: some lessons only become real when you're forced to practice them.
I thought of this memory this week as I was reviewing a few of our recent polls. In early June, we asked readers to share how lessons they’ve learned while traveling have impacted their careers.
One person, perhaps my long-lost twin, said: “I am a solo traveler, and have been doing so since my early twenties. Now that I am in my thirties, I learned the skills of managing, logistics, people skills and more. Nothing ever goes 100% right on a trip (at least my travel style), you have to learn how to manage unforeseen situations that can pop up, navigating a local language and people can be overwhelming.”
Others shared their experiences with culture shock, meeting kind people everywhere they went, and adopting healthier boundaries through cultural values they admired. I loved reading how revolutionary travel has been for so many.
Then I began looking at our other June survey responses. Lately, we’ve been asking a lot of advice-centered questions:
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What’s an unspoken rule in your workplace or industry that you’ve come to understand over time?
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What advice would you give someone who discovers a pay disparity in their workplace?
The goal with these, of course, was to gather feedback that could help more women successfully navigate their own life and career questions. As I read through the responses (which are good, by the way—I hope you’ll skim them), I found myself thinking about Manuel and the eight-hour tour, because there are some lessons you understand intellectually for years before you actually believe them.
The thing is, I’d started that tour thinking: How am I going to keep conversation going for eight hours? As if it was all on me to make the conversation interesting, to keep the ride from feeling awkward.
But Manuel was sharp. A geologist turned guide, he rattled off history, chemistry, politics, and pop culture throughout the journey. He stopped the van in the countryside because he said I needed to touch the cork trees, and I asked him to explain the etymology of some words he’d mentioned, which he did, because… naturally, he also knew everything about that, too.
The conversation was good—so good that somewhere outside Sesimbra I realized the “burden” of connection wasn’t assigned to me. He wanted the day to succeed as much as I did, and we were in this together.
By the end of the tour, it was me who was asking Manuel to stop the van—to pull over so I could touch a wheel from the Roman Empire that he’d pointed to in a field. “Of course,” he said. He believed history should be felt. I was ready to participate.
If someone had responded to our travel survey saying, “On a solo trip to Portugal, I realized that the things that make me anxious or uncomfortable aren’t mine alone to solve,” I probably would have nodded, thought, that's lovely, and moved on with my day.
But living it is what made it click.
All that to say, sometimes we don’t need more advice. Sometimes we need practice.
No listicle, newsletter, or survey response can do that for us. They can only point us in the right direction, but eventually we have to get in the van. The rest is participation.
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