Navigating The Seas: Sailing as a Metaphor for Transitions

As I’m in the middle of a career transition, I’ve been reflecting a lot about metaphors for navigating moments like this and I keep coming back to one: Sailing.?

Now, I say this as someone who has zero experience or interest in sailing despite having a father-in-law who has written 17 books on the subject. Still, when we open up the metaphor and explore its greatest depths, I suspect that you’ll find a framework for helping understand and plan (as much as you can) your next move.

You still with me? Here’s what I mean:

• The Water: This metaphor starts with understanding where we are and the state of things. Like life, water is full of constant change that is outside of your control, after all, we’re not talking about the ground here. What is the state of your water? Is it rough or smooth? What lives in the water around you? Is the water pushing you anywhere? Is it trying to upend you? Take note of the state of your water.

• The Weather: Take note of the elements outside that may be affecting your condition. Where is the wind pushing you? Is it calm? Is it cloudy? Can you see far ahead or are you navigating through fog? Maybe the weather is so bad that you’re adrift. This is ok…but it’s important to note so that you can figure out how to navigate in this very moment.?

• Your North Star: Where do you find yourself wanting to point when all feels lost? Because the North Star is up in the sky (and you don’t have a spaceship…yet) what is the thing you always find stays with you even though you may never reach it? This can be a purpose…even a calling. But you know you have a good sense of your North Star when you feel 100% unapologetic about what it is.

• Your Constellations: I think of these as your personal values. Here are mine. They are the pieces of you that help you orient when your ship is pointed in the wrong direction. They are not your North Star, but rather the elements in your sky that move around you. Sometimes your position gives you a different angle at their image, but they are unmistakable all the same. The weather can impact your view of them which is why it’s important to take a breath and notice if you can find them.

• Your Heading: Where are you pointed currently What direction is that? Does that direction reflect today’s need? Tomorrow’s need? Maybe you’re headed somewhere that you know is what will help you get to another destination. That’s ok of course, but it’s important to know where you’re currently pointed.

• Your Crew: Who is on the boat with you? Who comes for a period of your journey and then may drop off somewhere else? What jobs do they have? How are you putting your crew to work? Remember, it’s ok to put folks to work if they’re on your ship. They’ve also jumped on your ship because they trust you as the leader of YOUR ship. Simultaneously be a grateful but directive leader. And ask yourself how you recognize your crew so they know that you see them?

• Your Boat: What is your boat made out of? How does someone else along the sea recognize that it is your boat from far away? Are you a boat built for offense? For speed? To look and sail beautifully? What about your boat helps you stand out so that you’re not only distinct but also memorable??

• Your Sail: What is the driver on your boat that knows how to harness the wind? How does your sail translate that gust of wind into momentum? And, if there’s no wind to be had, how are you moving yourself? Are you rowing? Do you have an engine? Where is the fuel coming from? And, perhaps more importantly, what are you having to spend to get that energy? <— This is precisely why I like the sailing metaphor: the energy is free.

• Your Destination(s): This is related to your heading, but is ultimately where you’re trying to sail on this leg. Your heading may be how you’re using the conditions of the weather to get closer to your destination. How long is this leg going to be? Are you picking something up at the destination? Maybe you’re dropping someone off. Is your destination a harbor? An island? Maybe it’s something super cool out at sea that you just need to see for yourself.?

• Your Captain’s Log: How are you keeping track of your journey? What is the structure? How is that structure helping you keep track of your story? How are you evaluating your progress? And how do you want people to remember your story?

I truly think this brief summary barely scratches the surface of the power of this metaphor. The moment we wake up to our path the quicker we realize that the only thing harder than being on our path is being off of it knowing we should be on it.?

The moment we wake up to our path the quicker we realize that the only thing harder than being on our path is being off of it knowing we should be on it.?

Captaining a ship is not easy. There are so many conditions outside of your control that you need to balance alongside the intentions that you set for yourself. But life is no different. And when you start to understand that you are the one that controls the wheel, no matter the weather, you’ll wake up to the one reality of life:?Only you can steer it.?