Cory, I don't think I can even explain how much this piece resonates with what I've been thinking about recently. Our pursuit for freedom, but then getting lost in the vast sea of possibilities, and the draining fatigue of constant decision-making if we have no proper obligations (or as you framed it, constrains) that give us some much needed perspective. All of these things can turn out to be counterproductive if not directed towards a goal beyond freedom, and I love you named is as choosing things that have a heart. I am going to take a moment to digest everything you described but I will (maybe delusionaly) take it as a sign to finally focus on things that I wanted to pursue for so long without keeping all the options open. Thank you.
"Lost in the vast sea of possibilities" & "the draining fatigue of constant decision-making". Very very relatable. Also love this idea of the "goal beyond freedom"! As I say in the essay, it's not about collecting freedom for its own sake – it's about using it toward something exciting & meaningful. And that by definition means more constraints. But that's also where the beauty lies.
I've been thinking a ton lately about also developing certain rules – even as someone who hates rules! – but I call them "principles." They help us bridge our reality & our values. And they matter because they save energy & prevent drift. So for instance, "To thine own self be true" is a principle that helps ensure authenticity; or "I don't need permission to do what I know in my body, mind, & soul is right" is a principle that helps ensure freedom, adventure, self-development.
Best of luck to you as you continue exploring the path with a heart :)
Just catching up on this one Cory and it absolutely resonated with me as I consider when to retire from my government career. I’m afraid of wasting my unlimited free time without constraints or productive purpose. But maybe by choosing constraints and making a pact with myself I can (paraphrasing you here) “create room for more serendipity that makes me pulse with overwhelming elation!”
Yessss you can!! First there’s an exploration phase, though. I’m in one of them right now as we take a little break from the sailboat & go explore inland — including my next professional interests. But something I’m telling myself often: it’s totally OK to explore, & it’s OK if that exploration looks like wandering.
But then you dig a lil deeper & a commit a little more. So even now, I’m doing some teaching & coaching and really loving it! But I know it’s not the end, because I have so many more interests. It’s fun & rewarding, but it can’t be the end!
We can always redirect. That’s something I’m also dealing with now as we consider whether to even go back to the boat! It has become so much of my identity. But I also think that’s unproductive thinking, because it’s too rigid. We contain multitudes & keep discovering more!
I think the biggest thing is to develop a different relationship with “productivity”, & that will probably take a little bit of time — for you & me. A good investment though! Because there are many other ways to measure a life.
I know you’re going to do great, & I’m ALWAYS here if you want to chat! (It would be a pleasure, honestly!)
I'm like Aunt Pam. I missed you on Sunday but I still continued following my own path. Your ability to drill down to the essence is what makes your writing so compelling. You always give me that pep talk when I need it ... even if it's not directed at me. Thanks Cory. Just keep your mind open to the possibilities...
I like that quote comparing total freedom to constraints. I think most people, me included, need some form of time or energy limitation to get things done more productively. Dreaming is fine, but it needs to convert to action at some point.
Absolutely, Brad! There was a huge irony writing this up because I actually started on Wednesday for a Sunday due date (I usually start Friday). So what happened? I took the WHOLE time writing up what could've been done (albeit maybe a bit differently) in 2 fewer days. I'm still learning all this myself.... and then relearning haha
I recently read a lot from fellow sailor Nikki Henderson. She recently wrote an article titled "Freedom is an inside job". Although she does not even begin to unpack concepts as you do, it resonated deeply in me, the title sentence, because it is in every way an inside job.
I do think sailors have a lot of freedom, even though this freedom is indeed costly. A boat will take everything you have, and then some. I mean money wise, yes, but you may also throw your sanity in there if your can't adapt.
To me, the constraints of mother nature on a sailboat are far more glorious and doable than the one she throws at land lubbers, such as the monotony of shoveling a driveway, the urgency of fleeing a forest fire or the stupidity of poor human infrastructure trapping cars in traffic in heavy rain, overflowing drains & imposed detours on the way back to what one calls home... When I stop and wonder, I find our floating home (Columbia 56 1980), with it's challenges, is rewarding in the weirdest way.
Dayyyum amazing comment, Marie!! A fellow sailor with a GLORIOUS boat. Are you full-time? And if so, where at?
I’ve also LOVED the constraints of sailing & living on this sailboat the past 11 months. It’s 1 of the most clarifying & thrilling periods of my life. Yet there are some very difficult challenges since my husband & I are both working to start businesses. We have this indescribable urge to BUILD, & need the protected period to allow deep work. At a marina, it’s much easier than at anchor (especially now that we got some extra fans & sunshades). We’re navigating it well for now… But it’s POSSIBLE we’ll need to choose different constraints sometime soon.
We bought the boat in Mexico in July 2023. We left for French Polynesia a couple months after purchase, end of April 2024. It was not the initial plan. Truth be told, we had no plans, aside from tossing aside land life. Now, we're going backwards, East, but with a different route and different end point. Easter Island, Chile, Cape Horn, maybe the Antarctic, then going to Canada by the middle of the Atlantic: South Georgia, Tristan de Cunha, Santa Helena... That's the 2 years and a half plan.
My husband and I have slowly come to discover that, unbeknownst to us, what our lives truly needed most, aside from the abstract purpose we already had but were naturally slow to fulfill, was many more adventures than we used to have tucked in our rural town. Our relationship is better in immeasurable ways. Our wedding rings shine in contact with tuna blood, bilge water and salty lines.
Unlike some people, we didn't have a pile of cash set aside for this. But, we're lucky, I work from the boat. My coffee breaks and weekends are much better than they used to be. My work allows us to keep our bellies full, the boat afloat and particularly safe because of our precious cargo: our 4 kids. This open ended trip has been a relief to those young souls as well. They make friends everywhere. They are constantly exposed to problem solving and very patient in the face of situations that require nothing other than patience. In turn, we're privileged to have front row seats to see them grow up into proactive, emphatic little human beings.
Of course, I feel compelled to share some of the wisdom gained in our adventures, especially when you mention you guys might have to choose different constraints soon. Naming that possibility is wise though, I admit.
We came onto this behemoth of a sailboat from our previous boat, an 18 footer. At least we could check this one box: knows how to sail. That was great because wind is indeed wind. As you might have noticed, sailing is the easy part in this sailing lifestyle. We were really green. The real challenge lay with the unknowns about the boat, all the boat systems, how you have to fake it until you make it every time something breaks. That was a very steep learning curve, of which you are undoubtedly aware.
We're now finally more in a preventative maintenance mindset rather than a reactive one. It took a while. Last fall, so, after some 2 years, we came to this conclusion that we were finally appreciating the lifestyle instead of feeling like we were in some sort of self inflicted kafkaesque boat reality, which we tolerated because of the accompanying highs... My advice would be to not switch constraints before the 2 year mark. Many constraints will evaporate. Maintenance, now mostly on top. Anchor trust issues? Gone. Even the lack of space. I felt it much with 4 kids, now it's more than okay. I don't know how to explain this... Repetition, acceptance, plasticity of the mind? Budget is tight, but I don't think that will ever stop being a constraint, for us anyways.
Always looking forward to reading your next article, although, I still have some catch up to do!
Wow, thanks so much for sharing this epic story Marie!! What a life & adventure you're on. And your plans are so cool. Sounds like you're in a very good spot for yourself & thriving – even with what people say are the king & queen constraints: kids & finite money. So inspiring honestly that you're making this work.
We're starting some big convos tonight actually about what we want going forward, & of course continuing our sailing adventure will be on the whiteboard. We gotta consider everything though, & all we've learned along the way so far. It's a wild thought but honestly I feel like I've never had a big regret about a direction I take, because it always works in the long-run. So the question might even be – what do we want to spend the next year exploring? There are just some adventures that feel mutually exclusive with sailing life...
A boat, with tiny constraints; the ocean, less tiny but navigability constrained by weather, currents, wind, supplies…it was interesting to think about Corey’s engineering thoughts with yours about constraints. Thank for the engaging read!
So thrilled you enjoyed this, Erin. Tiny constraints, big constraints — still constraints! Super curious if you have reflections from your own life about this framing: fixed vs. chosen constraints & how you move forward in a direction that thrills you
Well Cory, after a life of roaming I just bought an 11 acre farm in Michigan. And all my writing and creative energy is back online after a long hiatus during the early years of childrearing.
I had always thought my boundless energy needed a boundless container. And it turns out it needed a physical one that demanded a commitment to a place. And maybe I did need the freedom to roam when I was younger so I could burn off some energy and learn on a bumpy road, but middle age called me to the largest single commitment I could ever imagined - a farm.
I love that you ended with a quote from The Teachings of Don Juan--I loved that book. The crack between the worlds and twiight as being that pivotal 'doorway.' Dusk has always been my favorite time of day. Maybe I'm looking for an opening into 'the other.' Also, in your post, it reminds me of when you're working your buns off, it seems you can always find time to squeeze in just one more thing. Like, what is that? I think having more free time than we're originally used to takes getting used to. It's like we've got to roll into it. imho.
Amazing reflection here, & thanks for reading all the way to end! Sunset is an obsession of mine, & given it’s so damn hot in Rio Dulce, I’m also getting to see sunRISE lately too… and I often meditate looking at the water. But you’re SO right that more free time takes more getting used — i think especially if you have a fire to do “something.” I hear from lots of people who say they’d just love 1 year to do NOTHING (& I hear from others saying, “Just chill Cory, you deserve it!”). But I appreciate you taking a diff tack: we gotta roll into it our own ways, & I think it’s becoming more clear as I experiment & NARROW :)
So happy you enjoyed this. I’m planning to keep exploring these topics of freedom & constraints, so if there’s anything you want to know, or think I should explore, I’d LOVE to know
Cory, I don't think I can even explain how much this piece resonates with what I've been thinking about recently. Our pursuit for freedom, but then getting lost in the vast sea of possibilities, and the draining fatigue of constant decision-making if we have no proper obligations (or as you framed it, constrains) that give us some much needed perspective. All of these things can turn out to be counterproductive if not directed towards a goal beyond freedom, and I love you named is as choosing things that have a heart. I am going to take a moment to digest everything you described but I will (maybe delusionaly) take it as a sign to finally focus on things that I wanted to pursue for so long without keeping all the options open. Thank you.
"Lost in the vast sea of possibilities" & "the draining fatigue of constant decision-making". Very very relatable. Also love this idea of the "goal beyond freedom"! As I say in the essay, it's not about collecting freedom for its own sake – it's about using it toward something exciting & meaningful. And that by definition means more constraints. But that's also where the beauty lies.
I've been thinking a ton lately about also developing certain rules – even as someone who hates rules! – but I call them "principles." They help us bridge our reality & our values. And they matter because they save energy & prevent drift. So for instance, "To thine own self be true" is a principle that helps ensure authenticity; or "I don't need permission to do what I know in my body, mind, & soul is right" is a principle that helps ensure freedom, adventure, self-development.
Best of luck to you as you continue exploring the path with a heart :)
Yes, I will return to it and savor it bit by bit as I carve a new path. 🩷
At the end of the day…the absolute bottom line necessity is motion.
This is where a sailboat is such a clear image.
You can flip that till back and forth like crazy, but if you don’t have forward motion, you don’t turn.
In fact you just look kind of silly.
Far too often we try to decide where first, contemplating while in a safe harbor…what should we do? All the while life rushes by us.
The irony is most of the time when we reach our destination it’s also different than we expected.
The point…the only point is life demands motion.
Couldn’t agree with this more, Brent!!
Just catching up on this one Cory and it absolutely resonated with me as I consider when to retire from my government career. I’m afraid of wasting my unlimited free time without constraints or productive purpose. But maybe by choosing constraints and making a pact with myself I can (paraphrasing you here) “create room for more serendipity that makes me pulse with overwhelming elation!”
Yessss you can!! First there’s an exploration phase, though. I’m in one of them right now as we take a little break from the sailboat & go explore inland — including my next professional interests. But something I’m telling myself often: it’s totally OK to explore, & it’s OK if that exploration looks like wandering.
But then you dig a lil deeper & a commit a little more. So even now, I’m doing some teaching & coaching and really loving it! But I know it’s not the end, because I have so many more interests. It’s fun & rewarding, but it can’t be the end!
We can always redirect. That’s something I’m also dealing with now as we consider whether to even go back to the boat! It has become so much of my identity. But I also think that’s unproductive thinking, because it’s too rigid. We contain multitudes & keep discovering more!
I think the biggest thing is to develop a different relationship with “productivity”, & that will probably take a little bit of time — for you & me. A good investment though! Because there are many other ways to measure a life.
I know you’re going to do great, & I’m ALWAYS here if you want to chat! (It would be a pleasure, honestly!)
I'm like Aunt Pam. I missed you on Sunday but I still continued following my own path. Your ability to drill down to the essence is what makes your writing so compelling. You always give me that pep talk when I need it ... even if it's not directed at me. Thanks Cory. Just keep your mind open to the possibilities...
"Just keep your mind open to the possibilities..." couldn't say it better myself, Darren!! Thanks for the awesome reflection. i really appreciate it!!
I like that quote comparing total freedom to constraints. I think most people, me included, need some form of time or energy limitation to get things done more productively. Dreaming is fine, but it needs to convert to action at some point.
Absolutely, Brad! There was a huge irony writing this up because I actually started on Wednesday for a Sunday due date (I usually start Friday). So what happened? I took the WHOLE time writing up what could've been done (albeit maybe a bit differently) in 2 fewer days. I'm still learning all this myself.... and then relearning haha
I recently read a lot from fellow sailor Nikki Henderson. She recently wrote an article titled "Freedom is an inside job". Although she does not even begin to unpack concepts as you do, it resonated deeply in me, the title sentence, because it is in every way an inside job.
I do think sailors have a lot of freedom, even though this freedom is indeed costly. A boat will take everything you have, and then some. I mean money wise, yes, but you may also throw your sanity in there if your can't adapt.
To me, the constraints of mother nature on a sailboat are far more glorious and doable than the one she throws at land lubbers, such as the monotony of shoveling a driveway, the urgency of fleeing a forest fire or the stupidity of poor human infrastructure trapping cars in traffic in heavy rain, overflowing drains & imposed detours on the way back to what one calls home... When I stop and wonder, I find our floating home (Columbia 56 1980), with it's challenges, is rewarding in the weirdest way.
Dayyyum amazing comment, Marie!! A fellow sailor with a GLORIOUS boat. Are you full-time? And if so, where at?
I’ve also LOVED the constraints of sailing & living on this sailboat the past 11 months. It’s 1 of the most clarifying & thrilling periods of my life. Yet there are some very difficult challenges since my husband & I are both working to start businesses. We have this indescribable urge to BUILD, & need the protected period to allow deep work. At a marina, it’s much easier than at anchor (especially now that we got some extra fans & sunshades). We’re navigating it well for now… But it’s POSSIBLE we’ll need to choose different constraints sometime soon.
We are full time, currently in Tonga. https://www.predictwind.com/tracking/SV-Seamer
We bought the boat in Mexico in July 2023. We left for French Polynesia a couple months after purchase, end of April 2024. It was not the initial plan. Truth be told, we had no plans, aside from tossing aside land life. Now, we're going backwards, East, but with a different route and different end point. Easter Island, Chile, Cape Horn, maybe the Antarctic, then going to Canada by the middle of the Atlantic: South Georgia, Tristan de Cunha, Santa Helena... That's the 2 years and a half plan.
My husband and I have slowly come to discover that, unbeknownst to us, what our lives truly needed most, aside from the abstract purpose we already had but were naturally slow to fulfill, was many more adventures than we used to have tucked in our rural town. Our relationship is better in immeasurable ways. Our wedding rings shine in contact with tuna blood, bilge water and salty lines.
Unlike some people, we didn't have a pile of cash set aside for this. But, we're lucky, I work from the boat. My coffee breaks and weekends are much better than they used to be. My work allows us to keep our bellies full, the boat afloat and particularly safe because of our precious cargo: our 4 kids. This open ended trip has been a relief to those young souls as well. They make friends everywhere. They are constantly exposed to problem solving and very patient in the face of situations that require nothing other than patience. In turn, we're privileged to have front row seats to see them grow up into proactive, emphatic little human beings.
Of course, I feel compelled to share some of the wisdom gained in our adventures, especially when you mention you guys might have to choose different constraints soon. Naming that possibility is wise though, I admit.
We came onto this behemoth of a sailboat from our previous boat, an 18 footer. At least we could check this one box: knows how to sail. That was great because wind is indeed wind. As you might have noticed, sailing is the easy part in this sailing lifestyle. We were really green. The real challenge lay with the unknowns about the boat, all the boat systems, how you have to fake it until you make it every time something breaks. That was a very steep learning curve, of which you are undoubtedly aware.
We're now finally more in a preventative maintenance mindset rather than a reactive one. It took a while. Last fall, so, after some 2 years, we came to this conclusion that we were finally appreciating the lifestyle instead of feeling like we were in some sort of self inflicted kafkaesque boat reality, which we tolerated because of the accompanying highs... My advice would be to not switch constraints before the 2 year mark. Many constraints will evaporate. Maintenance, now mostly on top. Anchor trust issues? Gone. Even the lack of space. I felt it much with 4 kids, now it's more than okay. I don't know how to explain this... Repetition, acceptance, plasticity of the mind? Budget is tight, but I don't think that will ever stop being a constraint, for us anyways.
Always looking forward to reading your next article, although, I still have some catch up to do!
Wow, thanks so much for sharing this epic story Marie!! What a life & adventure you're on. And your plans are so cool. Sounds like you're in a very good spot for yourself & thriving – even with what people say are the king & queen constraints: kids & finite money. So inspiring honestly that you're making this work.
We're starting some big convos tonight actually about what we want going forward, & of course continuing our sailing adventure will be on the whiteboard. We gotta consider everything though, & all we've learned along the way so far. It's a wild thought but honestly I feel like I've never had a big regret about a direction I take, because it always works in the long-run. So the question might even be – what do we want to spend the next year exploring? There are just some adventures that feel mutually exclusive with sailing life...
woah, I want a peek at that whiteboard now… ;)
A boat, with tiny constraints; the ocean, less tiny but navigability constrained by weather, currents, wind, supplies…it was interesting to think about Corey’s engineering thoughts with yours about constraints. Thank for the engaging read!
So thrilled you enjoyed this, Erin. Tiny constraints, big constraints — still constraints! Super curious if you have reflections from your own life about this framing: fixed vs. chosen constraints & how you move forward in a direction that thrills you
Well Cory, after a life of roaming I just bought an 11 acre farm in Michigan. And all my writing and creative energy is back online after a long hiatus during the early years of childrearing.
I had always thought my boundless energy needed a boundless container. And it turns out it needed a physical one that demanded a commitment to a place. And maybe I did need the freedom to roam when I was younger so I could burn off some energy and learn on a bumpy road, but middle age called me to the largest single commitment I could ever imagined - a farm.
Thanks for asking :)
thanks for the reflection, Erin!!
I love that you ended with a quote from The Teachings of Don Juan--I loved that book. The crack between the worlds and twiight as being that pivotal 'doorway.' Dusk has always been my favorite time of day. Maybe I'm looking for an opening into 'the other.' Also, in your post, it reminds me of when you're working your buns off, it seems you can always find time to squeeze in just one more thing. Like, what is that? I think having more free time than we're originally used to takes getting used to. It's like we've got to roll into it. imho.
Amazing reflection here, & thanks for reading all the way to end! Sunset is an obsession of mine, & given it’s so damn hot in Rio Dulce, I’m also getting to see sunRISE lately too… and I often meditate looking at the water. But you’re SO right that more free time takes more getting used — i think especially if you have a fire to do “something.” I hear from lots of people who say they’d just love 1 year to do NOTHING (& I hear from others saying, “Just chill Cory, you deserve it!”). But I appreciate you taking a diff tack: we gotta roll into it our own ways, & I think it’s becoming more clear as I experiment & NARROW :)
Hi Pineapple!
Great advice. I really appreciate your experience and wisdom here. Yum, Guatemala!!
So happy you enjoyed this. I’m planning to keep exploring these topics of freedom & constraints, so if there’s anything you want to know, or think I should explore, I’d LOVE to know
I will! I can’t stop thinking about the best Guatamalen refried black beans I ever had…… yum.
Your writing always makes me think. Thank you, amigo.
So glad it was received like that! Thanks Brandi