When the Wind Shifts
Notes on Change from Life Afloat SV Dawn Treader
Life on a sailboat connects you to nature’s rhythms in ways few other lifestyles can. We are in tune with the wind and the weather. With the tides and the currents. And with the way the topography of the places we visit impacts where we do—or do not—want to drop our anchor.
On the water we are as intimately acquainted with these elemental components as we are with seasons of change, both literal and emotional.
It’s a beautiful (even if at times frustrating—see here for more on that) way to live.
The cruising community is largely migratory. We move with the seasons to avoid cold and bad weather (including the ever-present summer and fall fear of hurricanes). We chase the elusive goal of sunshine, warmth (but not too much warmth), and just the right amount of wind for our sails.
And now, as full-blown summer sets on the Caribbean islands, our relationship with nature is on high display. Hurricane season is here. Our always-warm days are getting warmer. Squalls and windy weather have increased.
These shifts in the weather bring shifts for us as well. So, pardon the pun, we’re entering a new season here on SV Dawn Treader.
In the coming days, we’ll begin our last passage of this cruising season, moving from our current idyllic anchorage in the remote islands of St. Vincent and the Grenadines down to the industrial hustle and bustle of Trinidad. There, we’ll stow away our boat and head back to the U.S. to visit family, recharge, and prepare for more adventures ahead.
This change is good.
We need the time to reset and rest from adventuring. We miss family and friends we haven’t seen in months (or longer). And we love the alternate version of our lives lived tucked away in the North Carolina mountains.
That said, this change is also incredibly hard.
We’re leaving behind a very special piece of our hearts when we fly north in a couple of weeks and leave our floating home behind. We’ll miss our nomadic life until we return to it again—when the winter cruising season calls us back with better weather and gentler winds.
That’s the thing, isn’t it? Change rarely brings just one set of emotions.
Even when we know in our bones that something is good for us, heck, even when we’re excited about it, making a change comes with stages of grief, too.
This is just as true in life as it is in work.
In my work supporting women navigating career transitions, I see this duality play out often. Maybe a new job brings better pay, better hours, or more alignment with our values, but also brings the ache of leaving behind a team we’ve worked with for years. Maybe a big career pivot gives us the exciting challenge of proving ourselves in a new space, but also the frustration of being the “new gal” when we were used to being the expert.
Even the most exciting transitions at work often come wrapped in discomfort.
One of my favorite managers often quoted a familiar phrase: the test of intelligence is “the ability to hold two opposing thoughts in one’s head at the same time and still retain the ability to function.”
It sticks with me because I think it’s true.
Dealing with change is often the shaping activity that pushes us to grow. Change makes us stronger and better at something. It teaches us to work through discomfort to get to something richer on the other side.
And here’s the thing about change, especially the big, meaningful kind:
Just like that quote about opposing thoughts, change often asks us to hold joy and grief in the same space.
When we’re going through big transitions, we have the incredible opportunity to celebrate what’s ahead without denying the ache of what we’re leaving behind.
That tension we feel in those moments? It’s not a sign that we’re doing it wrong. It’s a sign that it matters.
As we prepare to pack our bags, stow our sails, and shift into the next season of life ashore, I’m reminding myself to feel it all. To honor the goodbye and the hello. The anchor we lift…and the new horizons ahead.
This is what growth looks like in life and in work. It’s not always clear-cut, it’s never perfectly timed, but it is 100% deeply human.
What season of change are you in right now?
What are you leaving behind, even temporarily, and what are you headed toward?
If you’re standing at the edge of a shift in your own professional life—considering a change, navigating the unknown, or charting a course back to yourself—I’d love to hear what season you're in. You’re not alone in the transition.
Come chat with me about it in the comments or over in the Beyond the Break community space. I’d love to hear what transitions you’re navigating.
Hi, I’m Ashley. I write Beyond the Break—a space for women navigating career transitions with intention, honesty, and heart. Through storytelling and reflection, I explore what it really means to build a sustainable, meaningful relationship with work.
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