I Really Don't Know WTF I'm Doing

A letter to anyone in the in-between

In the in-between

On Wednesday, I felt like an enormous disappointment.

People reach out to me all the time saying I’m living the dream. Often, that I’m living THEIR dream.

But that afternoon, I was strolling around Zone 4 in Guatemala City — past all the colorful walls, delicious foods, & laid-back way of life — feeling like my dream was… in the past.

“I really don’t know wtf I’m doing.”

The evening before, I had a 101.2 degree fever. I sneezed so hard I threw out my neck. I laid in our new apartment — the 1 with the fluffy towels & the big TV & the 10 new places for our 18yo cat, Pineapple, to lay around — & I couldn’t sleep.

I wished to be tired. But being sick wasn’t enough to counteract an overactive imagination & longing.

I laid there staring at the ceiling until at least 2am, fantasizing that I’d feel a new, exciting-enough direction if I just closed a few of the 12 people who had booked coaching intro calls with me the week before.

Why was I so stressed?

The reality of my world then was that only a few things were crystal clear: (1) that I was so f*ing happy I quit my job 13 months ago & went sailing, (2) that I was definitely NOT going back to life as it was, & (3) that I was unsure where to move next.

On the sailboat, I also didn’t know where I’d be in 1 month — let alone 6. The not-knowing was a feature. We still sailed through 11 states, 4 countries, & 4,500 miles of salty water.

And at least I knew I was sailing.

Now I know I’m living in a foreign city with my husband & our old cat. Money is only a pressing concern when I remember the gaping hole in our savings after 2 years of putting everything into our former floating home.

But we’re not going to starve.

And despite how much I’m enjoying my new digs, I couldn’t help thinking, “Yea, but what’s it all FOR?”

Honestly, I thought I’d be writing to you saying sorry that I wasn’t as inspiring as I used to be.

Then I chilled out.

Zone 4 in all its glory

Before I quit my job to go sail, literally everyone — OK, fine, like 9 out of 10 people — told me I was doing the exact right thing. Waiting till I was older would’ve been a mistake.

“GO NOW.”

But in the days before I put in my notice, I felt crazy for giving up my dream job. So I scheduled a meeting with a mental health professional at work. “Was I crazy?!” I needed an objective opinion.

When I told her over the phone what I was about to do, she got quiet.

I asked, “Are you still there?”

She said, “Yea, you’re just making me think about my dreams, too.”

I took it as 1 of many crystal-clear signs I was on the right track.

Then I moved onto that small sailboat, scared but excited af, & we sailed from North Carolina to Guatemala. Long-term readers will know it was hard for me — often feeling like learning to run a 100k without knowing how to walk. And yet, I had the time of my life.

But then, it was no longer enough.

And there was no new dream to share with anyone.

If I told you how I spent my days in Guatemala before Wednesday, you might’ve told me to go out & do something completely different. “Just enjoy yourself!” “Take your time!” “Chill tf out!”

But I tried that & no matter how loud I yelled at myself, it didn’t help.

And honestly, it felt terrible, especially waking up in a beautiful city, in a beautiful apartment, next to a beautiful person I love most in the world (& my cat) — & feeling like I was lost.

When I wrote about leaving Chérie 2 weeks ago, a reader said we don’t grieve the dream so much as the version of ourselves that belonged to it. I agree. I wasn't grieving the sailboat — I was grieving the dude who knew that he needed to sail.

And even though I had at least 20 years of crawling up mountains — from the pits of addiction to first-generation college grad to PhD scientist to a job advising Congress to an ocean sailor — it didn’t confer any more confidence than I had as a scared 19yo kid.

It felt like scrolling job boards at midnight thinking, finding ones that sounded moderately interesting, & then throwing the phone across the bed thinking: "who would even hire me?"

After all I’d done on this journey & in my life before, I still disqualified myself before anyone got the chance to reject me.

Someone commented yesterday: “You’ve learned to stop chasing material stuff but appear just as dissatisfied in life nonetheless.”

Ouch.

It stung because part of me believed it.

But I had turned a corner.

From my apartment

I could’ve kept this from you.

I could’ve continued projecting the confident nomad, venturing boldly through the unknown, so you could keep believing that if you ever took your leap, you’d come out the other side permanently glowing.

The photos would’ve backed me up. Big smiles in front of street art. Colorful scenes of the neighborhood. Volcanoes on the horizon.

But long-term readers will know I’ve never pretended to always be happy, & I’m not starting now.

There’s a saying: “No matter where you go, there you are.”

Most people will use this as a warning. Meaning, if you’re depressed in Denver, you’ll be depressed in Bali.

Sure. True enough.

But I’ve been experiencing a different side of it.

If you’re someone who’s always trying to suck the marrow out of life — Thoreau’s line, & the story of my whole existence since I could make decisions for myself — then “there you are” is sometimes the most exciting fact of your life.

You’ll get yourself into amazing & beautiful situations. You’ll find an incredible bone & crack it open. And for a while you’re intoxicated on the marrow. It’s the best thing you’ve ever tasted. You won’t even want to wipe your face.

For me, that was a 31-foot sailboat, 1 year at sea, & being the dude who knew that he needed to sail.

Then in May, stuck living in 100 sq. ft., in a rural Guatemalan marina in the 100˚F heat, with challenges even finding a doctor who could communicate with me clearly when my stomach was rumbling from an intestinal parasite – the marrow was finally gone from that bone.

But it wasn’t because the dream was a mistake or because I’d been faking it the whole time.

Because I’d sucked it dry. Exactly like I set out to.

And then you’re standing there, hungry again, holding a clean bone, with no idea where to find the next one.

More of my ‘hood

I thought I was uniquely lost until I posted a note last week telegraphing my angst & I started reading some replies from credible people COMPLETELY validating my confused state.

A sailor who moved off her boat 2 years ago told me she STILL has no idea wtf she’s doing. She said going back to “normal life” was harder than quitting everything to go sail — because when you leave to sail, it’s a massive risk, but at least you know what you’ll be doing. She said, “Going the other way is just mostly question marks with nothing specific on the horizon (pun intended?), and it feels less exciting because of that — so it just feels hard.”

I feel that.

A woman who spent her 20s adventuring around the world — including 2 years on a cruising yacht through Guatemala — told me “in the end it all felt superficial - like watching television.” She’d stretched herself. She had the stories. But she missed, “Making a contribution at multiple scales - personal interactions, community volunteering, work.”

This is a large part of the reason I moved off the boat.

A backpacker who lived in Lima for an extra year after traversing South America, not ready to go back to Canada because she’d changed so much, told me she still spent most of her days wandering the boardwalk consumed by existential dread. She paid a designer to build a brand kit for a solopreneur business she never started, because it felt important to be “working on something.” She said, “It’s only when I got back [to Canada] that the pieces started falling in place a bit.”

There were dozens more stories like this, just in response to 1 post.

And almost all of them from people who’ve been told they’re “living the dream.”

But does this mean NOT to pursue your dreams?

F*ck no.

This is what happens to searchers.

At 22yo, Hunter S. Thompson wrote to his friend Hume, “As your experiences differ and multiply, you become a different man… every significant experience alters your perspective.”

For better, then for worse, then for better again.

The marrow runs out because the dream WORKS.

It changes you, which is exactly what you asked it to do.

I still can’t believe I did it

If you’re now even more scared to make your leap because some feverish & sneezing ex-sailor dude in Guatemala just admitted he was a little lost — please hear me.

GO.

The marrow is real.

It’s the best thing you’ll ever taste.

And I’ve never met a single person in my decades of adventuring who regretted following the dream that they were obsessed about — no matter what it cost them on the other end.

But I get messages like this constantly:

Someone with a high-profile policy job who told me there’s NO WAY they can keep going till 60. Why? They really want to live on a farm & travel more.

Someone making multiple 6 figures who says their colleagues 5-10 years ahead of them look dead behind the eyes & their biggest fear in the world is to end up like them. What do they wanna be doing instead? High school math teacher.

Someone whose life photographs beautifully, & their LinkedIn profile would make you think they’re in the top 1% in terms of fulfilment, reached out to me saying, “I’m exhausted.” What do they wanna be doing instead? I don’t know because they ghosted me for our call.

These are the people who are risking regret.

So even if there’s confusion on the other side of whatever you’re dreaming, that’s really because you sucked that bone for as long as the marrow lasted. And that’s a good problem to have.

Flowers at the underground market in Zone 1

Yes, I had a stressful week. I was sick. I was legitimately unsure what I was doing then & next. I felt bad that this upcoming edition of the newsletter was gonna be a depressing one. And those facts were extremely unsettling for me.

I feared becoming a person who wouldn’t find another bone.

But thankfully, I slept much better on Thursday, Friday, & Saturday.

How, you might ask?

4 ways:

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First, I started feeling more patient & gentle with myself.

I’m writing constantly.

I’m talking to friends & telling them, “Hey, I don’t know wtf I’m doing!”

They all tell me, “That’s OK, dude! You just did something amazing & you’re in a transition period.”

I think, “Duh,” & it feels good, not disappointing.

A paying subscriber reminded me: “You are safe and you have options. Those are the big wins. The rest is gravy. Let time do its thing and soon the next moves will be evident.”

I’m meditating each day.

I’m breathing in & out.

My fever subsided.

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Second, I’m letting myself explore.

I made a big decision: I’m going to stop chasing new coaching clients. I don't think coaching is what I'm building toward. So I’m taking a big step back.

Anne-Laure Le Cunff would call it doing tiny experiments (she wrote a book by the same name). She introduced me to the idea of a pact, which I’ve talked about before, but basically it helps me try certain new things for set periods of time & stay accountable to them & myself.

I’m doing all that & feeling damn good about it.

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Third, I’m finding more things to love right here.

A fellow sailor named John once told us, “if you can’t find 1 thing to love in every place you’re at, you’re never going to be happy.”

So I’m eating quesabirria tacos. I’m walking around the old cathedrals & underground markets in Zone 1. I’m having more virtual film clubs with my good friends Matt & Martin (we’ve watched 118 films together & last week we discussed Close Encounters of the Third Kind 🤯). Last night, I had arepas with Corey & some great British sailor friends named Kate & David. I’m chatting with my parents way more often. I’m practicing my Spanish.

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And fourth — carefully, steadily — I’m following a new glimmer.

In the past week, something has started pulling at me in a way nothing has since I first found sailing. I’ve caught myself excited for tomorrow again. Not a fever this time. A new bone.

I’m not ready to say too much yet, but I’m considering leaning back into my love for science & teaching.

More on that in a future newsletter.

I’m also truly enjoying the World Cup from Latin America

A reader told me last week: “Once you wake up from one dream, you get to have the next one.”

Then she said, kindly, “It’s easy to forget that when you’re in the very beginning of waking up.”

I’m just barely waking up.

Yesterday, Pineapple found a new patch of sun on our bed in our 6th floor apartment & stretched out like she’d lived here 18 years instead of 2 weeks.

She doesn’t know what comes next either. She just knows the sun feels good, & her people are close.

That’s 1 thing to love.

I’ll continue walking forward from there.

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Thank you from the bottom of my heart to all my paying subscribers. Radical Paths is 99% funded by subscriptions. I can continue to pour my heart into this project because of my paying readers (thanks so much to all of you!). And even as we leave sailing life behind for now, the adventure will continue.

If you've been enjoying the journey & want to see where it goes next, consider upgrading for $5/month or $50/year.

La Piña already found her next right thing

If you’d like to chip in with a tip to support this project, every bit helps keep the boat floating (er, metaphorically) & the story going. Thank you 🙏

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Until next time,

–Cory