Sometimes You Need to Love Being Lost

Photo by Denise Jans on Unsplash

“I have no fucking idea where I’m going next,” I explained to Nathan, my no-bullshit coach friend. “I don’t know what I’m doing.”

“You’re being lost! That’s what you’re doing,” he said with loving conviction.

I was explaining to him that, after travelling different parts of Central America and Europe for the past five months, I didn’t know how to determine my next destination. But not only did I feel geographically lost, I felt mentally lost too.

“Everybody has these thriving businesses — new programs, retreats, coaching practices — whatever they’re doing. I just don’t. Fucking. Care. Anymore. And now I’m on the road with no direction.”

Okay, some context.

Almost 10 months ago, my fiancé died. Not after a long, hard disease — not that that makes things easier, just different — he died suddenly in an accident, right next to me, the day after we arrived in Thailand to work with a client in an intensive. (We were both transformational coaches). Ever since that day my life has been… Well, I don’t really have a word for what my life has been since. I’m not the same.

But this piece of writing isn’t actually about that part (the devastation, heartbreak and grief part) of my life. It’s about the aftermath, the reality that life goes on and bills need to be paid, and my cognitive dissonance with my identity and my business. Of course, though, the devastation, heartbreak and grief are the reason why I was thrown into this whole inquiry anyway. In response to my loss, I decided to get lost intentionally and travel the world. And although needed, it was proving to be damn hard.

“Nathan, I don’t know where I should go on the map, but I also don’t know how to gather up the energy to grow my business back in the direction it was going,” I said. I was — and still am — running my coaching business while working from a laptop and travelling — which, to some people, is kind of living the dream. But to me, it’s sometimes like living a different kind of dream — the kind of dream that isn’t real life and you’ll wonder when you’re going to wake up. When am I going to wake up? When is my fire going to come back?

“I have a question for you,” Nathan said.

Obviously the question was going to be brilliant, knowing Nathan, and obviously I was going to answer. I told him to ask away.

“What’s your relationship to being lost?”


“Some days, I can be lost. I love it,” I began to answer. “Then a few days later, my brain says ‘WHAT ARE YOU DOING?! YOU IDIOT! WHAT ARE YOU EVEN DOING?!’” And it’s this roller coaster up and down: embracing lost, then hastily trying to be found, then again on repeat.

Nathan first responded with a pretty brilliant point.

“You have a freedom that most people don’t have. You see that you are lost. The people who admit that they are lost are the ones on the verge of being found. You just have to let yourself be lost for longer than your inner dialogue can stand. Get out of your head, and feel your heart. Your heart can lead you, and your head is the one that keeps saying, ‘what are you doing?!’ But this isn’t necessarily something your head can solve.”

Then he said something I never, ever, ever would have thought of by myself.

“Imagine how many people are successful right now, and therefore don’t have the time to be lost and figure out what it’s all really about for them. You don’t know what you’re doing right now? Leighann! You are completely lost. That is what you’re doing right now. That is invaluable. You’re figuring out what it’s all about for you, from the new perspective you have after living through one of the worst things imaginable.”

I started picturing my life later down the road. A life where, after wandering and intentional lostness, I had the deep experience of being found.

This opened the floodgates for an even bigger concept: that being lost is invaluable not only for yourself, but for the people around you in your life: the people you love. You see, when a life event hits you that propels you into a state of being lost, and you bring intentionality to being lost, the more you find who you really are, then find what you really love, then do what you really love. And when you do what you really love, the people who love you are not only happy for you, they are inspired to do the same (if they dare). This creates an inspirational domino effect of discovering and living who you really are and doing what you really love. In short, being lost can eventually allow many people to be found.

The crazy part is that I’ve noticed some people view intentionally lost people as irresponsible or “in their own little world.” But what if these people are being the most responsible? What if these people come out of the other end of their lostness a happier, more fulfilled human being on this planet?

So maybe being in your “own little world” for a while makes our shared world happier.

This is where it gets funny.

“So… If you were in my shoes,” I asked, “what would your next action be?”

But he caught me.

“Where’s that question coming from?”

Long pause.

“…I’m trying to be lost as correctly as possible.”

“Yeah. Which is still you being in your head.”


And so, with that, I have chosen to be lost. My head is along for the ride, but I am doing my best to let my heart lead the way. And the things I’m discovering, well, they really are invaluable. I just needed to develop the patience to allow them to unfold, and still be unfolding.

The metamorphosis of my upcoming book, the changes in my coaching practice, the discovery of new passions or the deepening of old ones, the mastery of self, all of it — it’s all so worth surrendering to lostness.

The difference between you — potential lover of lost — and me, is possibly that a tragic event didn’t prompt your lostness. Maybe it’s a different loss. Maybe it’s a break-up. Maybe it’s the loss of your job. Maybe it’s a fight in your family. Maybe it’s that you’re studying in school and you’re not particularly bothered by what you’re studying but you’re not waking up thirsty and lit up every day.

The most famous part of The Riddle of Strider poem from the Lord of the Rings is: “not all who wander are lost.”

But what if it was also, “not all who are lost wander”?

What if what we really need is a strong dose of wandering?

And, if you can’t be totally gone-with-the-wind lost like I chose to be, lostness can be a practice integrated in your daily life.

How many minutes a day can you allow yourself to explore the unexplored? New hobbies? New events around the city? Doing a weekend trip to a part of your world that you’ve never seen? Learn a new language (like I’ve had to)?

How could you make lostness a daily practice to see if there’s something else you really need to find?

I wish you a wild adventure.


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