Some Milestones Deserve Witnesses. What Volleyball Taught Me About Traveling Together

I signed up for volleyball because I needed another way to stay active and maybe meet some new people. That was it. No grand plan, no deeper meaning. A month later, I'm sitting in the parking lot after a game, and I can't stop thinking about birthdays.

You know how milestone birthdays hit differently? Not the party part, but that weird space before them where you start taking inventory of your life. What you've accomplished, what you've let go of, and who you've become. I've watched clients book these trips around these moments for years, the 35th birthday solo adventure to Iceland, the divorce celebration in Malaysia, the career change sabbatical through South America. Volleyball gave me that same feeling, except I wasn't turning 50 or getting divorced. I was just learning to spike a ball without falling over.

There's something about marking time through shared experiences that hits different than marking it alone. Every Tuesday night for the last three months, I showed up to this court with the same group of people. We witnessed each other's terrible serves evolve into slightly less terrible serves. We celebrated the first time one of our team members actually got the ball over the net. We groaned collectively when another team member inevitably dove dramatically for balls that were clearly out of bounds. If you're following me on social media, you'll hear it in the background. These weren't life changing moments though. But they were our moments.

It made me think about the milestone trips I've taken solo. Each one was exactly what I needed at the time. Solo travel has this incredible ability to meet you where you are and give you space to become who you're meant to be next. But volleyball showed me something, that there's a different kind of change that happens when you mark time with others who are also in their own process of becoming.

I started thinking about the clients who come to me not just wanting to escape or discover, but wanting to celebrate something specific. The friend group planning a 40th birthday trip who've grown apart but want to reconnect. The mother-daughter duo marking a graduation or retirement. The recent widow ready to travel again but not ready to travel alone. These aren't people who need to learn how to be by themselves, they're people ready to honor a moment by sharing it intentionally.

What struck me most about our current volleyball season wasn't the improvement (though my serves have been getting better). It was how we accidentally created this container for witnessing each other's growth. Nobody was performing their best self or hiding their struggles. We were just showing up consistently, week after week, and letting time do its thing.

And that's what the best milestone travel feels like too. Not forced change or manufactured breakthrough moments, but simply creating space for whatever wants to emerge when you step out of your regular routine and pay attention differently.

I've been solo traveling for over a decade, and I'm not about to stop. There's still nothing quite like having a conversation with yourself in a foreign place, making decisions based purely on your own curiosity, discovering what you're drawn to when no one else's preferences are in the mix. But volleyball reminded me that some moments deserve witnesses. Some phases of life are worth marking with people who understand the significance, even if they can't fully understand your specific journey.

Maybe you're in one of those in between spaces right now. Leaving something behind, stepping into something new, or simply wanting to mark where you are in a way that feels intentional. Maybe you've done the solo work and you trust yourself completely, but you're sensing that this particular moment, this birthday, this transition, this celebration, wants to be shared.

I'm curious what that looks like for you. What are you celebrating or transitioning through that feels significant enough to mark with travel? And what would it mean to honor that moment in exactly the way it wants to be honored, whether that's completely alone or with the right people in the right place?

Because sometimes the perfect trip isn't about finding yourself, it's about celebrating who you've already become