I’m so glad you said yes and noticed this pattern. This is the undoing of your societal conditioning. It will take you many more months, if not years, to undo most of it. Trust me, I understand full well what you are going through. Just keep making sure you enjoy the places you visit. Even if you can return to them someday, they will never be the same.
Thanks for this, Jill. Something is changing starting a few weeks ago that is so profound. We’re about 8 months in, & my relationship with time is the noticeable thing that’s shifting. Since I wrote this article, I feared I may revert to old habits, but actually it turbocharged everything I wrote about here. Productivity is such an outdated concept out here on the water… & that might be my favorite thing to let go of, honestly. We have our basic needs met! And we’re enjoying life. What’s more to want?
Cory... This landed hard — especially “I had changed faster than my goals.” That’s such a clean, unsettling truth, and one most driven people don’t catch until they’re already resentful or numb.
I recognize that moment you describe — saying no to the thing that was the whole point — and realizing the cost only afterward. It’s sneaky how easily “freedom” turns back into self-imposed structure if we don’t actively protect leisure as something sacred, not leftover.
Defining enough feels like the real work here. Not as a finish line, but as a living boundary that needs revisiting as we change. I love that you’re treating it as an experiment, not a declaration.
And yes — saying yes to the reefs feels like a quiet rebellion against an older self who thought aliveness had to be earned.
Thanks for writing this one. It feels like a permission slip a lot of people don’t know they’re allowed to write for themselves.
Thanks Kelly! So thrilled that you enjoyed this & got so much out of it.
In this life, pretty much everything I know is constantly being tuned & refined. But one of the things most stable is how important it is to regularly check-in with myself on this question: is this even the life I want?
We’re in the process of doing this on our sailboat & it’s coming to some extremely powerful revelations. We’re deploying all this about goals & “enough” & letting ourselves get super honest about what emerges.
Our answer now is something like “Yes, but….” And we’re building cool stuff off that foundation. Still in the baking phase, but I’m excited to share what we’re working toward over the next few months :)
I love this framing — especially the “Yes, but…” phase. Nigel actually brought up the question of what’s next the other night, and we both just kind of sat there realizing we don’t have answers yet. That’s genuinely where we are.
We do have plans mapped through the start of 2027, so there’s plenty of runway for things to evolve without forcing conclusions. For now, we agreed to let that be enough.
Very curious to see what’s cooking for you both — excited to watch it take shape!
Super relatable, Cory. We put so much pressure on ourselves to keep moving, keep progressing, worried that our moments of leisure are setting back our goals timeline and we end up forgetting to live in the present moment too. It always never seems enough, and this is a good reminder to accomplish your goals, and not at the expense of a moment that may not occur again. The goals will still be there, will that specific snorkeling bay?
As usual Cory, you are speaking directly to what I am feeling! Accepting that we don’t need to constantly strive to reach goals that older versions of ourselves made can almost feel like failure. But it’s not, it’s growth. A perfect example is my desire to make my bed this morning. I was getting ready to head out to grab some lunch and I looked at my bed all disheveled from last nights sleep. In that moment I thought to myself, ‘a successful, driven person would make his bed before he did anything else’, and for an instant, I almost started making my bed, but something inside me said “who tf cares if I make my bed this morning?”. I sure don’t. I had the realization that I’m not that person who needs or indeed thrives on constantly seeking productivity or perfection. I literally have one driving force these days, and that is happiness. I really could not care less about large checking/saving balances or people’s perception of me as ‘successful’ or ‘driven’. I just want to do my best to be a person that people will remember as kind, loving and adventurous. At the risk of getting too philosophical, I am accepting that in the end, most of the things that society has told me are important, really are not.
Such a great reflection, Thomas! We have all these “productivity” and “success” gurus telling us what we need, and though I do think some of it’s useful, ultimately that is for all of us to decide for ourselves. I know I’d probably get further in my writing if I told people, “DO THIS,” but really the only thing I want to say to people is: (1) choose your own rules, and (2) live accordingly. Sounds like you’re on the way. These realizations are critical.
I love this article Cory! I’m glad you’re realizing this now while you are on this amazing adventure. While I am goal oriented, I have so many different interests that I don’t overdo any one of them. You could say that I live my life in moderation. That’s what drew me to a government career, the need to have balance between work and play, while also earning a decent living. I’ve always strived to work effectively (smarter, not harder) so I never felt guilty about leaving work on time and using my vacation time throughout the year. But too much leisure time is not a good thing for me either. After just spending two weeks on a Caribbean cruise, I was ready to get back to my home and work routines. I think that’s why I’m struggling with the idea of retirement. Without the satisfaction of productive work, will I be able to appreciate my leisure time? I think the answer will be to create goals that will fill that need and still allow me the freedom to enjoy whatever leisure adventures I decide to pursue.
You nailed something super important here, and it’s a question we all need to answer for ourselves. Your ability to moderate — to work hard but also leave on time (and take vacations) — is so admirable! And it explains why this recipe still works for you!
I wonder if instead of creating new goals, it’s really about creating a way of life that works & trusting that the right goals will emerge from that, not the other way around?
I’m with you, though. Even if I had $100 million, I wouldn’t want to be just sitting around all day on a beach. I would absolutely be pursuing my interests though, including in philosophy, conversation, & helping others. It’s intimately tied to my idea of success, which is really what makes me feel most alive.
I’m with you on that last point! Btw, if you end up in the western Caribbean, we discovered a great little island on our cruise last week. Caye Caulker, just off the coast of Belize. It was very laid back and had an authentic island feel with several cute local bars and restaurants. I thought of you since there were a number of sailboats docked alongside the place where we had lunch (The Lazy Lizard). And being near the Belize Barrier Reef, the water is stunning and easy to see all sorts of marine life just wading in a few feet of water!
Amazing, John! Thanks for the rec, and wow, so cool you got to see that. We’re leaning toward heading that way next — specifically Guatemala — so Caye Caulker will be within reach!! Another point for that region of the world!
This was great, Cory! It made me think about the patterns and juxtapositions in my own life—the enough and the more--and I had an a-ha moment of my own while crafting a comment. That comment turned into a whole essay, so I'll spare you that and just say: thank you! 😆
Wow, thanks for the comment, Kat! I’m still in a learning period myself, and I’m finding that there’s a huge difference between understanding it in theory & putting that theory into practice. But also, I think the key word is practice. Like meditation or anything else worthwhile.
So glad this led to some big insights for you. I’d actually love to hear if/only if you want to share.
It’s surprisingly hard to define enough. It’s more of a feeling, not a hard & fast number. But as I quote in the article, if we don’t define enough for ourselves, we’ll always default to more. It truly believe this is a source of regret.
Fantastic article! I’ve found that I’m the best mom and partner when I’m living in the moment and not ruled by my goals. Otherwise every second feels like a wasted moment to achieve vs. time to enjoy moments with my son/family that are so unique to this time of life only.
Thank you Rose! You’re so dang right! I read a really powerful article by Hunter S. Thompson recently that argued goals are OK, and being the type of person who achieves goals is important, but goals should always be secondary. Sounds like you perfectly identified what should be primary!
In much of the modern West, the dominant orientation is never enough. Time, money, attention, and even identity are treated as resources to be fully optimized. “More” is equated with freedom, and pressure is normalized as the price of ambition. Enough is provisional — a pause, not a destination — because satisfaction threatens momentum. The system works by keeping desire slightly ahead of fulfillment, which fuels growth and innovation but also produces chronic scarcity of calm, presence, and meaning.
By contrast, the Japanese sensibility of 余裕 (yoyū) centers on margin. Yoyū is not abundance or excess; it is the intentional preservation of space — in schedules, emotions, relationships, and environments. It allows room for error, for slowness, for the unexpected. A life with yoyū can still involve effort and aspiration, but it resists total saturation. Where the Western mindset asks, “How much can I fit in?”, yoyū asks, “What space must remain?” Not as a retreat from striving, but as a condition for durability, dignity, and grace.
Isn’t “never enough” some sort of battle cry? Wild. You nailed it, Brent.
It’s funny — the people arguing “more means freedom” are onto something, only if they actually cash in. But 90% don’t. They buy more crap & raise the ante. They may be rich but have no wealth. They might even reach “retirement age” with less optionality than someone who made 20% their top salary. Doesn’t sound like freedom to me.
I also love what you said about the system working because desire > fulfillment. Queue the commercials.
Love the part about yoyū, too! Thanks for educating people on that!
You are learning some of the most important lessons. Slow down and let yourself be in the moment-especially enjoy the beauty all around you right now! When you return, you will be a kinder soul, ready to help others find the same way. Proud of you.
Honestly, I felt so alone in this quest until pretty recently, and I’m so glad you share the same philosophy, Katherine. I’m in total agreement — we need to let our new experiences change us. It might end up being the most important lesson in my wild chapter at sea.
This, this!, is what we all need to take a moment and evaluate for ourselves. I firmly believe the beast of American capitalism would come to a screeching halt if every one of us knew what our “enough” was. Thanks for writing this, Cory!
I totally agree, Niquelle. I’ve started posting on LinkedIn & though I’m finding my niche of well-adjusted people, I’m pretty shocked how many people are preaching the complete opposite of “enough.” I also can’t help but think about how many of them will come to their own realizations about burnout & excess in a few years, decades, or on their deathbeds. A lot of it, I think, comes from how precarious it all feels — even wealth & success. But everyone treating their youth, then middle age, like they’re sports players who are going “age out” are actually preventing these important questions. And they’re doing nothing but feeding the beast.
I truly hope I can keep my independence, my balance, & still meet all my needs. But this is one huge experiment!
Defining what we consider to be enough, wrestling with our definition of success and not letting our goals define us is constant work! Especially in today's world where society is always telling us that bigger is better and we need more, more, more! I believe that if we are already asking these questions and engaging in these conversations, then we are already on a more soul-aligned path. Being more aware does not make our lives easier but it most certainly makes them more delicious!
Thanks Lisa! Ironic, isn’t it, that defining success for ourselves & resisting the hammer of more goals requires more work!? But it’s some of the best work we can do. You and I are totally aligned, including on the role of society in this quest. Keep on living this way though & we’ll undoubtedly have a fulfilling and more-delicious life.
Man, the importance of reclaiming aimlessness, that space where wonder and real living can take hold. Here here. Goals are almost a drug, they feel so good and compelling, like a bodily high. I've noticed how snippy I am with the kiddos when I have a rigid goal, how little time I spend meandering aimlessly about the garden. Especially in this world of ours, which is obsessed with goals and productivity, which is oriented toward efficiency and not "wasting" any time. Claw back spaciousness.
I’m so glad you said yes and noticed this pattern. This is the undoing of your societal conditioning. It will take you many more months, if not years, to undo most of it. Trust me, I understand full well what you are going through. Just keep making sure you enjoy the places you visit. Even if you can return to them someday, they will never be the same.
Thanks for this, Jill. Something is changing starting a few weeks ago that is so profound. We’re about 8 months in, & my relationship with time is the noticeable thing that’s shifting. Since I wrote this article, I feared I may revert to old habits, but actually it turbocharged everything I wrote about here. Productivity is such an outdated concept out here on the water… & that might be my favorite thing to let go of, honestly. We have our basic needs met! And we’re enjoying life. What’s more to want?
You’re giving me so much more to look forward to!
Enjoying life!! YES! That is what it is all about!
Cory... This landed hard — especially “I had changed faster than my goals.” That’s such a clean, unsettling truth, and one most driven people don’t catch until they’re already resentful or numb.
I recognize that moment you describe — saying no to the thing that was the whole point — and realizing the cost only afterward. It’s sneaky how easily “freedom” turns back into self-imposed structure if we don’t actively protect leisure as something sacred, not leftover.
Defining enough feels like the real work here. Not as a finish line, but as a living boundary that needs revisiting as we change. I love that you’re treating it as an experiment, not a declaration.
And yes — saying yes to the reefs feels like a quiet rebellion against an older self who thought aliveness had to be earned.
Thanks for writing this one. It feels like a permission slip a lot of people don’t know they’re allowed to write for themselves.
Kelly 💛
Thanks Kelly! So thrilled that you enjoyed this & got so much out of it.
In this life, pretty much everything I know is constantly being tuned & refined. But one of the things most stable is how important it is to regularly check-in with myself on this question: is this even the life I want?
We’re in the process of doing this on our sailboat & it’s coming to some extremely powerful revelations. We’re deploying all this about goals & “enough” & letting ourselves get super honest about what emerges.
Our answer now is something like “Yes, but….” And we’re building cool stuff off that foundation. Still in the baking phase, but I’m excited to share what we’re working toward over the next few months :)
I love this framing — especially the “Yes, but…” phase. Nigel actually brought up the question of what’s next the other night, and we both just kind of sat there realizing we don’t have answers yet. That’s genuinely where we are.
We do have plans mapped through the start of 2027, so there’s plenty of runway for things to evolve without forcing conclusions. For now, we agreed to let that be enough.
Very curious to see what’s cooking for you both — excited to watch it take shape!
— Kelly
Super relatable, Cory. We put so much pressure on ourselves to keep moving, keep progressing, worried that our moments of leisure are setting back our goals timeline and we end up forgetting to live in the present moment too. It always never seems enough, and this is a good reminder to accomplish your goals, and not at the expense of a moment that may not occur again. The goals will still be there, will that specific snorkeling bay?
Exactly, Tamara! Glad you enjoyed this! I still have a lot to learn myself, but I’m on the way.
As usual Cory, you are speaking directly to what I am feeling! Accepting that we don’t need to constantly strive to reach goals that older versions of ourselves made can almost feel like failure. But it’s not, it’s growth. A perfect example is my desire to make my bed this morning. I was getting ready to head out to grab some lunch and I looked at my bed all disheveled from last nights sleep. In that moment I thought to myself, ‘a successful, driven person would make his bed before he did anything else’, and for an instant, I almost started making my bed, but something inside me said “who tf cares if I make my bed this morning?”. I sure don’t. I had the realization that I’m not that person who needs or indeed thrives on constantly seeking productivity or perfection. I literally have one driving force these days, and that is happiness. I really could not care less about large checking/saving balances or people’s perception of me as ‘successful’ or ‘driven’. I just want to do my best to be a person that people will remember as kind, loving and adventurous. At the risk of getting too philosophical, I am accepting that in the end, most of the things that society has told me are important, really are not.
Such a great reflection, Thomas! We have all these “productivity” and “success” gurus telling us what we need, and though I do think some of it’s useful, ultimately that is for all of us to decide for ourselves. I know I’d probably get further in my writing if I told people, “DO THIS,” but really the only thing I want to say to people is: (1) choose your own rules, and (2) live accordingly. Sounds like you’re on the way. These realizations are critical.
I love this article Cory! I’m glad you’re realizing this now while you are on this amazing adventure. While I am goal oriented, I have so many different interests that I don’t overdo any one of them. You could say that I live my life in moderation. That’s what drew me to a government career, the need to have balance between work and play, while also earning a decent living. I’ve always strived to work effectively (smarter, not harder) so I never felt guilty about leaving work on time and using my vacation time throughout the year. But too much leisure time is not a good thing for me either. After just spending two weeks on a Caribbean cruise, I was ready to get back to my home and work routines. I think that’s why I’m struggling with the idea of retirement. Without the satisfaction of productive work, will I be able to appreciate my leisure time? I think the answer will be to create goals that will fill that need and still allow me the freedom to enjoy whatever leisure adventures I decide to pursue.
Thrilled that you enjoyed this, John!
You nailed something super important here, and it’s a question we all need to answer for ourselves. Your ability to moderate — to work hard but also leave on time (and take vacations) — is so admirable! And it explains why this recipe still works for you!
I wonder if instead of creating new goals, it’s really about creating a way of life that works & trusting that the right goals will emerge from that, not the other way around?
I’m with you, though. Even if I had $100 million, I wouldn’t want to be just sitting around all day on a beach. I would absolutely be pursuing my interests though, including in philosophy, conversation, & helping others. It’s intimately tied to my idea of success, which is really what makes me feel most alive.
I’m with you on that last point! Btw, if you end up in the western Caribbean, we discovered a great little island on our cruise last week. Caye Caulker, just off the coast of Belize. It was very laid back and had an authentic island feel with several cute local bars and restaurants. I thought of you since there were a number of sailboats docked alongside the place where we had lunch (The Lazy Lizard). And being near the Belize Barrier Reef, the water is stunning and easy to see all sorts of marine life just wading in a few feet of water!
Amazing, John! Thanks for the rec, and wow, so cool you got to see that. We’re leaning toward heading that way next — specifically Guatemala — so Caye Caulker will be within reach!! Another point for that region of the world!
This was great, Cory! It made me think about the patterns and juxtapositions in my own life—the enough and the more--and I had an a-ha moment of my own while crafting a comment. That comment turned into a whole essay, so I'll spare you that and just say: thank you! 😆
Wow, thanks for the comment, Kat! I’m still in a learning period myself, and I’m finding that there’s a huge difference between understanding it in theory & putting that theory into practice. But also, I think the key word is practice. Like meditation or anything else worthwhile.
So glad this led to some big insights for you. I’d actually love to hear if/only if you want to share.
I'm sure snorkeling was amazing. As I watch snow fall....
I’ve heard about the incredible snow! Where do you live, Ted?
It may sound funny in this moment but I actually miss the snow in Denver! That meant play in the mountains, especially with a AWD car :)
Just west of Philadelphia. Denver knows how to deal with snow. We don’t usually get this much!
I hope you’re staying cozy!
“The feeling that I need more is because I hadn’t bothered to define enough.” This says it all. It’s one of our biggest struggles. When is it enough?
It’s surprisingly hard to define enough. It’s more of a feeling, not a hard & fast number. But as I quote in the article, if we don’t define enough for ourselves, we’ll always default to more. It truly believe this is a source of regret.
Fantastic article! I’ve found that I’m the best mom and partner when I’m living in the moment and not ruled by my goals. Otherwise every second feels like a wasted moment to achieve vs. time to enjoy moments with my son/family that are so unique to this time of life only.
Thank you Rose! You’re so dang right! I read a really powerful article by Hunter S. Thompson recently that argued goals are OK, and being the type of person who achieves goals is important, but goals should always be secondary. Sounds like you perfectly identified what should be primary!
In much of the modern West, the dominant orientation is never enough. Time, money, attention, and even identity are treated as resources to be fully optimized. “More” is equated with freedom, and pressure is normalized as the price of ambition. Enough is provisional — a pause, not a destination — because satisfaction threatens momentum. The system works by keeping desire slightly ahead of fulfillment, which fuels growth and innovation but also produces chronic scarcity of calm, presence, and meaning.
By contrast, the Japanese sensibility of 余裕 (yoyū) centers on margin. Yoyū is not abundance or excess; it is the intentional preservation of space — in schedules, emotions, relationships, and environments. It allows room for error, for slowness, for the unexpected. A life with yoyū can still involve effort and aspiration, but it resists total saturation. Where the Western mindset asks, “How much can I fit in?”, yoyū asks, “What space must remain?” Not as a retreat from striving, but as a condition for durability, dignity, and grace.
Isn’t “never enough” some sort of battle cry? Wild. You nailed it, Brent.
It’s funny — the people arguing “more means freedom” are onto something, only if they actually cash in. But 90% don’t. They buy more crap & raise the ante. They may be rich but have no wealth. They might even reach “retirement age” with less optionality than someone who made 20% their top salary. Doesn’t sound like freedom to me.
I also love what you said about the system working because desire > fulfillment. Queue the commercials.
Love the part about yoyū, too! Thanks for educating people on that!
You are learning some of the most important lessons. Slow down and let yourself be in the moment-especially enjoy the beauty all around you right now! When you return, you will be a kinder soul, ready to help others find the same way. Proud of you.
This old Mom Mom
Honestly, I felt so alone in this quest until pretty recently, and I’m so glad you share the same philosophy, Katherine. I’m in total agreement — we need to let our new experiences change us. It might end up being the most important lesson in my wild chapter at sea.
Also, thanks for being proud :)
This, this!, is what we all need to take a moment and evaluate for ourselves. I firmly believe the beast of American capitalism would come to a screeching halt if every one of us knew what our “enough” was. Thanks for writing this, Cory!
I totally agree, Niquelle. I’ve started posting on LinkedIn & though I’m finding my niche of well-adjusted people, I’m pretty shocked how many people are preaching the complete opposite of “enough.” I also can’t help but think about how many of them will come to their own realizations about burnout & excess in a few years, decades, or on their deathbeds. A lot of it, I think, comes from how precarious it all feels — even wealth & success. But everyone treating their youth, then middle age, like they’re sports players who are going “age out” are actually preventing these important questions. And they’re doing nothing but feeding the beast.
I truly hope I can keep my independence, my balance, & still meet all my needs. But this is one huge experiment!
Great article, Cory!
Defining what we consider to be enough, wrestling with our definition of success and not letting our goals define us is constant work! Especially in today's world where society is always telling us that bigger is better and we need more, more, more! I believe that if we are already asking these questions and engaging in these conversations, then we are already on a more soul-aligned path. Being more aware does not make our lives easier but it most certainly makes them more delicious!
Thanks Lisa! Ironic, isn’t it, that defining success for ourselves & resisting the hammer of more goals requires more work!? But it’s some of the best work we can do. You and I are totally aligned, including on the role of society in this quest. Keep on living this way though & we’ll undoubtedly have a fulfilling and more-delicious life.
Man, the importance of reclaiming aimlessness, that space where wonder and real living can take hold. Here here. Goals are almost a drug, they feel so good and compelling, like a bodily high. I've noticed how snippy I am with the kiddos when I have a rigid goal, how little time I spend meandering aimlessly about the garden. Especially in this world of ours, which is obsessed with goals and productivity, which is oriented toward efficiency and not "wasting" any time. Claw back spaciousness.