Why We Can’t Do Hard Things Alone
What life on a boat taught me about community and how it connects to our work lives, too
This week, I turned on the chat feature here on my Substack page so community has already been top of mind. But something else happened, too, and it sent me even further down the community rabbit hole.
First, a little context:
For much of the year, I live on a sailboat. We have a land base in the mountains of North Carolina, but over the past two years, our boat has become our primary version of home. Life afloat is incredible. It’s mobile, full of adventure, and genuinely a lot of fun (despite the hefty dose of effort required to make it all work).
Cruisers, by nature, are migratory. We chase warmth and good weather—heading one direction in the winter and another in the summer. That’s why, right now, we’re working our way south to tuck our beloved floating home into a safe harbor for hurricane season. Once she’s secure, we’ll head back to the states for a much-needed stretch of rest, recharge, and dry land.
There’s so much to look forward to: running water we don’t have to make, a break from anchors and dock lines, and precious time with family that’s hard to see regularly when flights and easy access are few and far between.
But there’s one part that’s always hard: the “see you laters.”
It’s what we tell our kids (and ourselves) to say when we part ways with cruising friends rather than goodbye. Sometimes it’s just for a few weeks or months with the hope of reuniting down the line. Other times, it’s open-ended—or even final—as friends head for far flung horizons or leave the cruising life altogether.
This part of the season is full of those goodbyes, and this week brought an especially hard one. The little trio of cruising families we’ve been traveling with for nearly a year has now separated. There were lots of tears, promises to stay in touch, and a deep sense of gratitude for what we have shared over the past year.
These are the people who helped us succeed at living on a boat.
They offered wisdom from their own mistakes. They helped puzzle through unexpected problems (which are plentiful when your home floats). They celebrated our wins—and we celebrated theirs.
We’ve met people who didn’t take to the cruising life and returned to land fairly quickly. Their stories are all unique, but there’s often a common thread: they didn’t find their people. Without community to bolster them through the hard times and share the joy of the good ones, the isolation becomes overwhelming.
Because community is the difference.
The people in your corner are your teachers. Your cheerleaders. Your co-problem-solvers. Your truth-tellers. And when you're walking an unfamiliar path—like we are, and like so many of you are in your careers—community isn’t a luxury. It’s essential.
So the timing of these reflections, right as I launched the chat feature, feels meaningful.
They’re both reminders that when you’re doing new or hard things, you shouldn’t have to do them alone.
Whether you’re living on a boat or rethinking your relationship with work, there will always be challenges, quiet stretches, and tough decisions. And just like in cruising, the difference between enduring and thriving often comes down to who’s walking alongside you.
As we head into the weekend, I invite you to pause and consider:
Who’s in your corner right now?
Who are your thought partners, your cheerleaders, your sounding boards?
What kind of support do you need as you explore a more intentional, sustainable relationship with work?
And if you’re not sure, if you’re searching for that support, I want you to know: I’m in your corner.
Every meaningful relationship I’ve built on the water started with one small thing in common—and then grew into something more. Our shared thing might be the desire for work that feels energizing instead of depleting, aligned instead of forced, whole instead of fragmented. That’s a pretty fantastic place to begin.
Let’s build from there.
Join the chat or share in the comments.
Or reach out directly. I'm always up for a good virtual coffee.
Here’s to the weekend. And to not doing this alone.
Ashley Regan Burke is the founder of Beyond the Break, a space for professional women navigating career transitions, burnout, and reinvention. She’s a coach, writer, and liveaboard sailor who believes in building intentional lives—and careers—that feel aligned, sustainable, and joy-filled.
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