Why Your Freedom Isn't Working

A letter to anyone who hates constraints

Complete freedom wasn't what I thought it was

For the past 11 months, even while rolling through treacherous conditions at sea, I’ve remained steadfast to writing my weekly newsletter. And it has made for an insanely more enriching life.

Even the time I was at anchor in storm-force winds that kept me up all Saturday night, I wrote an essay while I was on my 3-6am watch, pounding words onto my screen while peeking at the GPS pin to ensure we weren’t washing ashore. Because I needed to publish by 9:39am ET that morning.

Or same when we pulled into Guatemala 3 Saturdays ago, and I needed to morph my messy iPhone notes into something legible (& hopefully interesting) within the 4 hours after dinner & before waking up early to move further upriver. And there was something actually quite easy about that.

Why?

First, because I was swimming in high levels of specific inspiration. Yes, my seafaring world has required enormous mental & physical investment, but in return the floodgates blasted wide open with new insights, breakthroughs, & perspectives. My world literally fluid & therefore, week-to-week, I got exactly what I wanted when I first chose this life: more serendipity & less predictability.

The sailing stories often wrote themselves.

But also, I put myself inside a box. “How the HELL do I balance all this?!” A simple rule for myself (1 essay per week), & limits on how many resources I would invest (the essay was going out Sunday morning!), which often made my life incredibly more challenging.

A few of you may have noticed that last Sunday — even from the relative comfort of my marina in the Guatemalan jungle, with a table that was NOT trying to launch my laptop across the sailboat — I did NOT send out an essay.

And that decision made my skin crawl with discomfort.

I felt bad for not sending my weekly correspondence to the handful of readers who I knew had become accustomed to my essays on Sunday (hi Auntie Pam).

But ultimately the guilt didn’t get my creative juices flowing.

I’d been so excited for marina life for exactly this reason — that when I finally got to land, I could write about ANYTHING I wanted.

No more automatically writing about the wild sailing adventure from the week before. I had my sights on much more than a sailing blog since day 1. And this was my chance.

But my relatively uninspiring & unfocused life in the marina offered no obvious material. And even with the weekly newsletter pledge staring me down, it wasn’t enough to deliver.

Paradoxically, I needed more constraints.

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The sailboat is my good box

People tell me all the time: “Man you got so much freedom on that sailboat!”

I’ve heard countless sailors mention too that this is why they chose sailing.

But in reality? We can’t do whatever we want.

Mother Nature & our finite bank accounts have much greater say over our day than any willpower we can muster.

And for me, my sailing adventures were only possible if I chose a floating plastic hull the size of a parking spot with few extras. No working fridge. Weeks at a time without fresh produce. Cleaning up sewage the morning before setting sail. Sitting in a trough between 10-foot waves thinking: "OMG when will I wake up?!"

Completely free? Not even close.

But that’s not what I actually wanted.

I wanted to do something meaningful — & ASAP.

My chosen box has made that happen for me.

We moved aboard without knowing how to sail or thrive at sea, so we HAD to learn. We had a mission to get through the Caribbean before hurricane season, so we HAD to keep moving. And I had this crazy idea of writing a weekly newsletter to share my journey in real-time, so I HAD to figure out a way.

But I got super creative — & I found immense fulfilment, even among the madness.

We sailed 4,500 miles in 11 U.S. states & 4 countries. We met countless new friends along the way.

And my writing pact forced me to relay stories that would've otherwise sat forever in the recesses of my memory — never processed, never articulated, never shared.

This was NOT total freedom. But it was a type of freedom.

It’s the type I needed to get somewhere worthwhile to me.

My sailboat is small but she has taken me far

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I had complete freedom once & it was terrible

Until I was 22yo, before I started community college, I could technically do anything. But actually I just worked a job I hated & complained a lot.

I lived in Los Angeles & went through a short period when I told people I wanted to work in the film industry.

While I was sweeping the floors 1 day working at Starbucks, a film executive chatted me up & asked me a super confrontational question: “Why not sweep floors at a film studio down the street?”

Honestly the idea was solid, but I got red & defensive.

“Because I want to keep my options open.”

What a shitty answer.

Keeping your options open sounds smart. But open for what, exactly?

I never got anywhere truly exciting until I poured all my energy into something specific. Until I started making decisions that narrowed my options further in a direction that was more interesting.

But I didn’t really understand this until I found a loving partner who inspired me & held me accountable (hi Corey), & we moved to an environment that better suited my personality (rainy & cloudy Portland, Oregon). Then I decided to commit to the often-annoying & totally-optional path of more school.

Any American who has started college with limited cash & without a plan learns quickly that the system (plus all the subsequent debt) forces you to narrow your path quickly. And if you’re not sure what you want, it’s scary.

But I took a quick sampling of all the classes that sounded interesting, I gave them my all, & within 3 quarters I heard my biology instructor describe THE REASON leaves change colors every fall. I had never heard something more captivating — or more beautiful. I needed to know more.

After my PhD & getting a cushy government biologist job — just before sailing — I had tons of freedom again. I could technically do lots of things I can’t do today on my sailboat. I could influence projects at a dozen federal agencies. I could find a different 9-5 job if I wanted. I could sleep on a queen-sized bed. I could watch films with theater quality surround sound. I could drive my AWD Subaru on Saturday mornings to a nearby hiking trail in Denver, or to the Safeway at 1am for honey mustard & onion pretzel bits. I could earn enough cash for fancy dinners, clothes, new furniture, & airfare wherever…. when I got time off work anyway.

Yet I don’t really miss all that stuff.

My freedom had expanded, but not in the optimal directions.

I needed a path that was more mine.

And I could’ve stayed stuck for decades if I didn’t identify better constraints.

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The sailboat is only 1 type of freedom

Every time I've had too much freedom in life, I've drifted. Every time I've chosen better constraints, I've gone somewhere worth the time.

I spent years accumulating financial freedom, career freedom, & freedom of movement. But I wasn’t using them in the ways I really wanted, & I was starting to slide into a life I definitely didn’t want. I had more stuff than ever. And I was about to empty my savings on a renovation for a house — & take out tons of debt — because I didn’t really have a better idea.

I still thought I was keeping my options open.

In his book Inside the Box: How Constraints Make Us Better, David Epstein writes:

“Because the brain is naturally inclined to avoid effortful thinking and to rely instead on familiar patterns, complete freedom tends to lead to unoriginal ideas, simply repeating what is known. Constraints push the brain beyond its default tendencies, forcing it to engage in deeper problem-solving. Total freedom, then, is the enemy of creativity, and constraint its companion.”

I was making more money, but didn’t know what to do with it. I was earning more work experience, but not leveraging it toward the work I wanted. I was collecting credit card miles, but didn’t have enough time to use them.

I was learning that freedom is worth nothing if you’re not moving in a direction that meets your needs.

What I needed was a clearer set of rules — or else I risked big regrets.

I just had to choose smartly.

In her book Tiny Experiments: How to Live Freely in a Goal-Obsessed World, Anne-Laure Le Cunff explains to people who are feeling unsure about how to proceed that you need to consider a course of action that YOU think is

1. appropriate,

2. exciting, &

3. doable

After we discovered the world of sailing, I knew my actions needed to take me on a path where I could leave my 9-5 job, buy the smallest & least expensive sailboat that could cross oceans, & learn how to sail. Then see what else this insanely abundant world had to offer if I kept going.

It was also to write up my stories & publish them. And then see where that led.

These decisions would narrow my freedom in some important ways, but they also created room for more serendipity that made me pulse with overwhelming elation.

Yes, we needed to spend 10 months refitting the sailboat ourselves. Then negotiate the sailing schedule with Corey that allowed me to write. Turn down invitations from friends & other sailors along the way. Often shut myself alone because my new commitments were more important than anything else on a given day.

Complete freedom would’ve caused us to NEVER set sail, & I would’ve skipped much more than 1 week of my newsletter — guaranteed.

And I would’ve certainly missed a calling that emerged after months of putting my work out there (coaching others through their radical paths) — which has made this journey feel worthwhile in ways I’m only starting to articulate.

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Constraints you choose vs. constraints that choose you

My husband Corey is a mechanical engineer & knows a TON about constraints.

When I told him I’ve been thinking about “chosen constraints,” he pushed back. His argument: most constraints aren’t really chosen. They’re facts based on the reality around you. Like the properties of metal or needs of a customer.

We only had so much money, so we needed to figure out what path & timeline to take given that reality.

The no-fridge situation wasn’t a philosophical choice initially — it was from finite cash & the desire to leave NOW. Same with taking our 18yo cat. We didn’t choose to love her so damn much. We just did, & so she came with us.

But you design around certain constraints. And you get creative within them.

He's right. But there are still constraints within our direct control — & these are the ones worth choosing carefully.

One type is a pact: a voluntary constraint you design yourself, carry out with no one checking on you, and that creates direction, accountability, & forward motion within your specific reality.

In Tiny Experiments, Le Cunff says:

“Compared to linear goals, a pact fosters an experimental mindset — an attitude of openness and curiosity, a willingness to learn with a sense of receptiveness, and a lack of preconceived notions.”

A well-designed pact looks like this:

“I will [action] for [duration].”

Like: I will post on Substack every week for 12+ months.

Or: We will work on this sailboat in this dusty-ass North Carolina boatyard 6-7 days per week until we & the boat are capable.

That boatyard wasn’t anywhere close to the picturesque life you imagine when you think of sailing. We spent 10 months through rain, snow, & uninspiring humidity. Fiberglass dust on everything, learning skills we may never need again, making mistakes we'd have to undo & redo. Some days I'd look at our half-dismantled boat & think: "What the HELL are we doing?" But we'd made a pact. And the pact got us out of that damn boatyard.

Pacts help you learn something new — even when you don't want to. They help you try something before quitting your job. They absolutely feel like constraints. They definitely limit freedom.

But they ARE chosen. By YOU. And they also help you move forward.

Then it’s up to you to re-evaluate your pacts & do 1 of 3 things. Either:

• persist if it’s still rewarding,

• pause if it’s currently unfulfilling, or

• pivot based on what you now know

When we committed to sailing, we did it within our fixed constraints (limited money, lack of experience, our elderly cat) & told ourselves:

“We will live on this damn sailboat for 1 year whether we hate it or not.”

It felt long enough for us to figure out how to sail, thrive aboard, & see if the path was sustainable long-term. We could get past the honeymoon period. And it could help us determine exactly what we needed & didn’t need in our specific sailing reality.

Every pact is a chosen constraint. And our lives are full of them, whether we think of them that way initially or not.

The question is: Which constraints are just part of your reality — & which ones can you actually choose?

Doing whatever I want was never the point

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The right pact at the right time

My situation has changed since sailing to Guatemala. And last weekend, no matter how guilty or terrible I felt, I just couldn’t do it. My options were limitless. Yet I couldn’t coalesce around an idea. So I skipped the newsletter.

I know it doesn’t matter in the grand scheme of world events. I know that few people other than my Aunt Pam probably even noticed. But to me, it was an Earth-shaking event because it made me realize something important:

I needed to reconsider my precious pact.

So I’ve been thinking a ton about how to engage on Substack going forward. And as Le Cunff suggests, I’ve been reflecting on what about it is rewarding, unfulfilling, & may need to change given my evolving circumstances.

But I know I still need to write. I just want to keep exploring wtf Radical Paths is about now that I’m not sailing every week.

Kierkegaard wrote about the “dizziness of freedom” that comes from infinite possibilities — & that this produces intense anxiety in people. He wrote:

“What I really need is to be clear about what I am to do, not what I must know… the thing is to find a truth which is truth for me, to find the idea for which I am willing to live and die.”

Instead of writing last week, I spent time reading about freedom & constraints, and thinking through what to do about all of it. But it didn’t feel productive in the moment (it didn’t lead to a newsletter last Sunday). And after reading Kierkegaard, I honestly ended the day feeling way more confused.

But I got 2 days closer to understanding the next idea for which I am willing to live & die.

Reevaluating your pacts takes some courage, especially when you’re not sure what you’re doing instead. But if your pacts aren't creating room for exploration, they've become the wrong box. And there’s a huge missed opportunity to find that seed that could blossom into something more interesting than what you’re doing today.

We may decide to keep sailing beyond the 1 year mark.

I may decide to persist with my weekly newsletter. (I know my Aunt Pam will be happy about that.)

But clearly not all chosen constraints are good constraints. Some — like immediately making some new commitment just for the sake of filling the gap — would be the worst decision possible.

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Choose the path that has a heart

Certain constraints are fixed realities. Gravity. Our body’s dependence on fresh water. Our 80ish year life expectancy. Aspects of our personalities. Our savings, debts, skills, & dependents today.

You design around these.

And they force you to get creative — or get further & further stuck.

But some constraints you CAN choose. Pacts. Principles that help you live according to your values. Rules you consent to fully. And these are the ones worth getting right.

The person sweeping floors at Starbucks in Los Angeles, sitting in a cubicle in Denver, & feeling claustrophobic on a sailboat in Guatemala are all constrained. The difference is whether they’re moving toward their own vision or someone else’s.

You don’t need to blow up your life to find out. You just need to be honest about which box you built — & whether it still has a heart.

“Look at every path closely and deliberately. Try it as many times as you think necessary. Then ask yourself and yourself alone one question. Does this path have a heart? If it does, the path is good. If it doesn’t, it is of no use.”

-Carlos Castaneda, The Teachings of Don Juan*

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*Thanks to my new friend Matt who shared this with me last week, exactly when I needed it.

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Until next time,

—Cory