Refining the Course

Cruising taught me to embrace fluidity. Now I’m applying it to my career.

Years ago, when we first started seriously contemplating becoming cruisers, I developed a very narrow definition in my head of what constituted a “real” cruising family. This family needed to sell everything they owned, wave goodbye to all the pieces of life they knew, hop onto a boat (specifically, a monohull blue-water sailboat), and push off from the dock to circumnavigate. It sounded romantic and exciting, but the pragmatic side of me wondered if it was really something we should (or more importantly wanted to) do.

Pretty quickly, however, I learned that there is no narrow definition of cruiser. Some cruisers do indeed do the legitimately awe‑inspiring version of cruising that I describe above. But the spectrum is wide. Some are seasonal cruisers who have a full‑blown land life for half the year and cruise for the other half. Some run up and down the same parts of the world over and over, enjoying years in the Caribbean or Sea of Cortez. Some, like us, are winging it and seeing what happens from one season to the next.

In all of these iterations of cruiser, there is a common thread. We all learn to do really hard things and be proud of ourselves. We all learn to hold on loosely to the beauty of life because it is fleeting and changes constantly, and that’s actually totally okay. We all learn to say see you later to incredible people we may not ever see again, and we learn how to manage the excitement when we do unexpectedly cross paths.

And if there’s one trait I’ve come to associate with life aboard more than any other component that makes a “real” cruiser, it’s this one:

Fluidity.

In order to live as a cruiser, you must not only accept, but actively embrace the fact that each day is different, that the plan you have is more of a suggestion to Mother Nature, and that the future is always a kind of shady mystery. You have to be fluid.

I love a good definition break. Here’s how the dictionary describes fluidity:

flu·id·i·ty
/flo͞oˈidədē/
noun
the ability of a substance to flow easily.
smooth elegance or grace.
the state of being unsettled or unstable; changeability.

Fluidity is both a blessing (easy, elegant, graceful) and a curse (unsettled, unstable). I tend to think it leans more blessing, but those less complimentary traits can serve as cautions. This life has a fair share of unsettled in it, even if it can be a lot of fun.

At first, I thought fluidity was just a cruising thing, something to adapt to tides, weather, seasons. But the longer I’ve lived this way, the more I realize it’s become part of how I define myself. Or at least how I want to. And yet, when I look at how I’ve approached my professional life this past year, I realize that I have not been bringing fluidity into the conversation. Instead, I’ve been trying to shape my career into something rigid and labeled based on my perception of what I “should” be doing now. In fact, I think I’ve been resisting the very fluidity that serves me so well in such a huge part of my life.

I’ve built the same sort of narrow definition for this next phase in my career just like I did when we first started thinking about cruising.

When I quit my full‑time job at the end of January, I wasn’t sure what I wanted to do next, but I had some good ideas about things I didn’t want to do. Over those first few months of soul‑searching and writing and talking and thinking, some direction emerged.

I knew I didn’t want to experience the rug‑pull feeling that came from a company I loved being acquired by a company I fundamentally disagreed with on many levels. I knew I didn’t want to find myself doing work that did not inspire me and instead drained me. I knew I wanted to feel like I had flexibility to engage with my family and the world around me in addition to work. I did not want to spend 60+ hours at my laptop making money for some shady corporate shareholder.

Eventually, I developed a perception that the thing I needed was to not work for corporate organizations anymore, at least not as a full‑time employee. I determined that I needed to “go it alone” and be my own boss. So I’ve tried that. I’ve partnered with a small business consultancy, picked up a contract with a smaller-than-big-tech corporate organization, posted roughly a million posts on LinkedIn to build a coaching business, and written creatively here in this space while also being published in a professional publication. I’ve spent nearly 11 months outside of a true full‑time job, though I’ve certainly worked more hours than a full‑time job by having three or four jobs.

And here’s what I’m learning: just like the definition of cruiser, the definition of a fulfilled professional version of me doesn’t have to look a certain way. The ground I’ve gained in flexibility and in a focus on aligned work doesn’t require me to define myself narrowly as someone totally independent and on her own. I don’t have to be so rigid as to say I can’t go back to a corporate organization or that I must be a certain kind of consultant, freelancer, or contractor. I don’t have to do work I don’t find joyful or inspiring just so I can say I’m a consultant. And work for a corporate entity (regardless of status) can be aligned if I’ve found the right company.

All in, I think my biggest takeaway nearly a year into this journey to find the next phase of my career has been that it is, for me at least, less about how I work — whether as a full‑time employee or a consultant or something in between — and more about my relationship with the work itself.

Maybe this isn’t mind‑blowing. Maybe if you’re still reading this, you’ve gotten here and are disappointed with my takeaway.

It’s taken me a while to see it, but I think I’ve been asking the wrong questions. Not “What’s the job title?” or “What box do I fit into?” but “Does this way of working let me be who I want to be?”

And so, as I make decisions on my next steps, I’m making sure that I’m thinking about the answers to the questions that matter. I’m reminding myself that fluidity means that nothing is set in stone and that I can keep trying on different things until I find a good fit. And I can decide that a good fit isn’t one anymore when it isn’t. I don’t need to stick to a definition that doesn’t serve me just because I somewhere along the way decided it should. Fluidity for the win.

The future isn’t a fixed point. It’s a current. And I’m learning to flow with it.

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Hi, I’m Ashley. I write Beyond the Break. This is a space for honest storytelling, identity-in-motion, and the messy middle of personal and professional growth. Through storytelling and reflection, I explore what it really means to build an intentional, sustainable, and meaningful relationship with work and life.

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