Hey Rick, we discussed this topic a while back on one of my posts, at the time I suggested Freedom was the highest aim, you suggested Meaning was. Well like you, after nearly 2 years of "freedom" I have come around to your way of thinking. At the time I was trying to define freedom not as time/money freedom, which is what most people think of, but I was trying to frame it as existential freedom. But after thinking (and living) it out, I think what I was really trying to define was in fact Meaning. I do still differentiate time/money freedom vs existential freedom as a material vs spiritual contrast, but at the end of the day, there can be no existential freedom without some kind of undergirding meaning.
Put more simply: a person without freedom but who has meaning can live a rich and rewarding life, even if it's a struggle at times. But a person with freedom and no meaning is destined for ennui, listlessness, purposelessness, etc which are all a form of privileged existential suffering.
In practice I'm still working out what all of the above mean for me, I find myself oscillating between enjoying my freedom but wrestling frequently with what to do with said freedom. At many points over the past couple years I've found myself asking, "What am I doing here?", (not geographically but existentially) which is a meaning question, not a freedom question.
It's a privileged problem but I ended up in a situation where I didn't need to work anymore after years of hustle and grind as an entrepreneur. I didn't know what to do with myself, I still don't to some extent and find myself pursuing projects that I don't care about that much, only to abandon them as I don't have the drive as don't need to earn. But then feel like I'm not productive if I'm not developing something new and creating a business. There's no side project that is really meaningful if you don't need the money in entrepreneur world (who wants to build an AI tool for fun, like why? And so on). I'm now trying to reframe my life and see just daily routines such as cleaning my home, walking my dogs, taking care of my family, and so on as my aims. But it's hard, I identified with your article alot.
Thanks Carrie for your comment. Your situation sounds very familiar to mine...
I'm not good at doing nothing either and had the is-my-side-project-meaningful-enough conundrum, but after stumbling around for awhile, have really settled into writing (esp now fiction writing).
One thing that helped me was lasering in on the question: "what part of business building did I enjoy the most/brought flow states?" Then it was about finding DIFFERENT activities that fulfilled that in NEW contexts, and NOT trying to replicate it within the business world.
E.g. for me it was understanding I lean to "creative thinker in solitude." I like working on constantly evolving problems, alone/in my head, and creating something original = writing.
For someone who likes building software, that could be a solo/weird/creative/artsy software project that makes $0. Or Mike Karnjanaprakorn is an example of someone who wants to build with others: https://newsletter.mikekarnj.com/
No idea if that helps you or not, but that's just how it worked for me.
Thank you so much, I got lost down a hole for days reading Mike's newsletter you suggested, it hit exactly right so thank you for the recommendation. It made me realise what a gift a well timed and perfectly on target reading recommendation can be to someone - it leads you in all different directions. Because of it I read lots of articles he has then recommended in his newsletter with thought altering ideas and signed my son up to an AI maths tutor he recommended.
If you've not read it, Wanting: Memetic Desire by Luke Burgess and Jenny ODell how to do nothing are good reads around this topic 👍
Really appreciated this read. It’s a good reminder that aimless wandering won’t bring more fulfillment than grinding 90-hour weeks, but having the freedom to pursue meaning on your own terms is what makes all the struggle worthwhile. Excited to see where your book project goes!
I'd like to see an unpacking of what meaning is . I understood your reframe by observing my father who has retired and struggles to figure out how to use his time.
Yet, I wonder if words like meaning and purpose are too loaded with alternate meanings/baggage to get the point across. Another framing I've been thinking about is challenge and finding your own tension.
Every story needs intention and obstacles, that create tension. If there are obstacles that feel impossible, the difference between a tragedy and adventure is if they are overcome or not.
But if there are no obstacles, the story is flat and boring.
What's difficult about defining meaning is it's one of those "you know it when you have it" feelings.
Kinda like love... e.g. can you define "love"? If you fall in love or if you feel love from a parent/family member, you know exactly what I'm talking about. But how would you explain it? Deconstruct it? That's a problem poets have been working on for centuries 😅
You're tension point is interesting, and I'd be curious to hear more about what you think. Every story does need obstacles, but that is a GOOD STORY. Is that the same as a GOOD LIFE? E.g. if you ever fall in love w/ someone, do you need massive obstacles to overcome in order to experience that love? I'm not so sure... But I'd be curious to hear more.
It seems to me that the underlying question of this article is "how can one feel happy in a sustained way, joyful, satisfied with one's life, whole". The mind's tendancy is to search for an answer externally which will always end up failing, or get only part of the answer. Because the mind is it's own source of misery. True sustained happiness is found within, and does not depend on circumstances. It is not by doing something that one becomes happy.
I am bringing this up because having been financially free for the last 8 years, the fundamental shift that made all the difference and checked all those boxes has been internal, not external. Once that shift occurs the question of meaning (and most self oriented question) become less important. You think about having fun and helping others, as bonus, not as a means to an end. Hope it helps, it comes from a place of love.
The thing is, freedom enables you to pursue meaning. For many, it is the stepping stone and true path to meaning. Most people are too tied to soul-crushing jobs or the daily grind to find meaning, other than some sort of rationalized acceptance that their cubicle was in fact their destiny.
I like this framing. Though the popular frame of "freedom" (e.g. financial independence, escape from system, etc.) doesn't usually include your definition of freedom, or would you disagree?
I agree. It's interesting, when I read your article again, you state a few times that you experienced freedom in the sense of financial freedom. So it fits the popular frame of freedom as you state in the comment. We all tend to assume freedom is the ability to choose to do what we want. If what we want is financial independence or escape from the system, very few of us will ever become free. But if we want the highest good, we can all be free right now. We just have to change what we want.
You nailed what I was trying to say - probably more clearly stated than my post 😅
Then again, most people hand-wave me off when I say this and go back to chasing financial freedom, only to delay the real problem a few more decades...
It's human nature. It is much easier to chase the external than to work on our interior life, because it's much easier to gripe about external things than to blame ourselves.
Very well stated. I think it becomes more apparent the older we get, too. You can palpably sense it in older people. The cumulative result of our choices to either blame the external or cultivate an interior life. We get either bitter or better the older we get and I believe it is the direct result of consistent choice between these two postures.
Thanks Rick for such an enjoyable read, funny and to-the-point👌It really hit. If this "freedom" we seek means endless resources, no commitment to anything and a perpetual care-free feeling, then that kinda sounds like a life out of touch with reality. Being a blissful butterfly the whole time isn't really possible. We just got to try and create a life that makes sense to us, and is fullfilling enough to keep us going through the not so great parts of it, in touch with the world around us.
I appreciate this perspective. I've always thought of freedom as an end unto itself, but maybe it functions more like a means to an end than I originally conceived. There's both freedom from (doing something) and freedom to (do something). In both cases, it's an enabler of something else. Definitely something to reflect on further!
Most people’s closest concept of “freedom” = vacation, and when that vacation is so constricted (e.g. max 2 weeks), it’s hard to envision anything different beyond those 2 weeks.
Yes!! Thanks for writing this, Rick. I was also one of those people who sought after freedom as the highest form of wealth. But man, I never realized that freedom --> letting go and that means embracing a void if you don't make up for it with meaning.
I think I'm on the side of wanting to pursue work worth doing all my life (or at least while I derive meaning from it, but work not as in a job but work as in the thing I want to keep doing for the rest of my life).
I happened to be chatting with GPT about my discovery of meaning. Born in a hellish country, freedom was never innate. I burned myself for it, rebuilt my personality, and chose the meaning of my existence. I call this whole process metamorphosis.
Here's my summary:
A person is born carrying a basket.
At first, the basket is filled by others — family, society, the environment. It grows heavy with things that are not truly theirs.
One day, the person feels the weight and decides to set the basket on fire.
The flames consume everything: the borrowed beliefs, the false identity, even the mask they wore as a “self.”
When the fire dies, they stand in the ashes.
Some people pick up only what survived the flames, the few things that are real. Others return to the ruins and rebuild the same basket again, filling it once more with what never belonged to them.
Those who are brave enough may burn it again, and again, until finally the basket holds nothing but what they have chosen for themselves.
This is transformation:
• To discard what was given, even if it feels like losing yourself.
• To pick up only what is true.
• To repeat the fire as many times as necessary until nothing false remains.
Only then do you walk out of the flames, not with what you inherited, but with what you are.
—-
I hope my unique experience can help you. I believe we all live in a shell from birth, and it is the environment that gives us this shell. I think your "meaning" is the feeling of knowing clearly what you need. Thank you for your wonderful article
Where I'm less sure (haven't thought through it enough), is whether we need to completely discard 100% of what is given to us. It almost seems impossible, e.g. we inherit so much that we take for granted, and there might be places where we should accept what others give us without discarding it (simple example is scientific truths that I, in no way, will try to refute).
Have you thought about this? When you say "discard what was given," are there any places you shouldn't discard it?
Very true, Rick! I feel the search for meaning is not so common and I guess it will have it's own quandaries on the emotional journey it'll take one through. Reading your post reminded me of some of this post which I had come across https://offpisteinvesting.com/howard-stevenson-whats-enough/ and I would also recommend some of Alfred Adler's insights from the book "The Courage to be Disliked" of meaning and happiness "Happiness is the feeling of contribution without the need for recognition"
Hey Rick, we discussed this topic a while back on one of my posts, at the time I suggested Freedom was the highest aim, you suggested Meaning was. Well like you, after nearly 2 years of "freedom" I have come around to your way of thinking. At the time I was trying to define freedom not as time/money freedom, which is what most people think of, but I was trying to frame it as existential freedom. But after thinking (and living) it out, I think what I was really trying to define was in fact Meaning. I do still differentiate time/money freedom vs existential freedom as a material vs spiritual contrast, but at the end of the day, there can be no existential freedom without some kind of undergirding meaning.
Put more simply: a person without freedom but who has meaning can live a rich and rewarding life, even if it's a struggle at times. But a person with freedom and no meaning is destined for ennui, listlessness, purposelessness, etc which are all a form of privileged existential suffering.
In practice I'm still working out what all of the above mean for me, I find myself oscillating between enjoying my freedom but wrestling frequently with what to do with said freedom. At many points over the past couple years I've found myself asking, "What am I doing here?", (not geographically but existentially) which is a meaning question, not a freedom question.
Damn... you nailed it Dave.
Your middle paragraph really nails what I see as a fundamental error in American (at least) thinking: that freedom alone is the answer.
(just like money-alone is the answer, or health-alone, etc.)
Many would be much better off, yes pursuing freedom, but simultaneously pursuing meaning because the former may not come until too late / not at all.
It's a privileged problem but I ended up in a situation where I didn't need to work anymore after years of hustle and grind as an entrepreneur. I didn't know what to do with myself, I still don't to some extent and find myself pursuing projects that I don't care about that much, only to abandon them as I don't have the drive as don't need to earn. But then feel like I'm not productive if I'm not developing something new and creating a business. There's no side project that is really meaningful if you don't need the money in entrepreneur world (who wants to build an AI tool for fun, like why? And so on). I'm now trying to reframe my life and see just daily routines such as cleaning my home, walking my dogs, taking care of my family, and so on as my aims. But it's hard, I identified with your article alot.
Thanks Carrie for your comment. Your situation sounds very familiar to mine...
I'm not good at doing nothing either and had the is-my-side-project-meaningful-enough conundrum, but after stumbling around for awhile, have really settled into writing (esp now fiction writing).
One thing that helped me was lasering in on the question: "what part of business building did I enjoy the most/brought flow states?" Then it was about finding DIFFERENT activities that fulfilled that in NEW contexts, and NOT trying to replicate it within the business world.
E.g. for me it was understanding I lean to "creative thinker in solitude." I like working on constantly evolving problems, alone/in my head, and creating something original = writing.
For someone who likes building software, that could be a solo/weird/creative/artsy software project that makes $0. Or Mike Karnjanaprakorn is an example of someone who wants to build with others: https://newsletter.mikekarnj.com/
No idea if that helps you or not, but that's just how it worked for me.
Thank you so much, I got lost down a hole for days reading Mike's newsletter you suggested, it hit exactly right so thank you for the recommendation. It made me realise what a gift a well timed and perfectly on target reading recommendation can be to someone - it leads you in all different directions. Because of it I read lots of articles he has then recommended in his newsletter with thought altering ideas and signed my son up to an AI maths tutor he recommended.
If you've not read it, Wanting: Memetic Desire by Luke Burgess and Jenny ODell how to do nothing are good reads around this topic 👍
Thanks for the recs!
Really appreciated this read. It’s a good reminder that aimless wandering won’t bring more fulfillment than grinding 90-hour weeks, but having the freedom to pursue meaning on your own terms is what makes all the struggle worthwhile. Excited to see where your book project goes!
You nailed it right there.
I needed this in my inbox today. It hit home. Thank you.
Glad it resonated, Michael. Curious what made this hit and/or relate to your life?
I'd like to see an unpacking of what meaning is . I understood your reframe by observing my father who has retired and struggles to figure out how to use his time.
Yet, I wonder if words like meaning and purpose are too loaded with alternate meanings/baggage to get the point across. Another framing I've been thinking about is challenge and finding your own tension.
Every story needs intention and obstacles, that create tension. If there are obstacles that feel impossible, the difference between a tragedy and adventure is if they are overcome or not.
But if there are no obstacles, the story is flat and boring.
Thanks Ved. Maybe not perfect answer to your question, but I do expand on the meaning of meaning here (plus old vs. new versions):
https://newsletter.thewayofwork.com/p/frontier
What's difficult about defining meaning is it's one of those "you know it when you have it" feelings.
Kinda like love... e.g. can you define "love"? If you fall in love or if you feel love from a parent/family member, you know exactly what I'm talking about. But how would you explain it? Deconstruct it? That's a problem poets have been working on for centuries 😅
You're tension point is interesting, and I'd be curious to hear more about what you think. Every story does need obstacles, but that is a GOOD STORY. Is that the same as a GOOD LIFE? E.g. if you ever fall in love w/ someone, do you need massive obstacles to overcome in order to experience that love? I'm not so sure... But I'd be curious to hear more.
It seems to me that the underlying question of this article is "how can one feel happy in a sustained way, joyful, satisfied with one's life, whole". The mind's tendancy is to search for an answer externally which will always end up failing, or get only part of the answer. Because the mind is it's own source of misery. True sustained happiness is found within, and does not depend on circumstances. It is not by doing something that one becomes happy.
I am bringing this up because having been financially free for the last 8 years, the fundamental shift that made all the difference and checked all those boxes has been internal, not external. Once that shift occurs the question of meaning (and most self oriented question) become less important. You think about having fun and helping others, as bonus, not as a means to an end. Hope it helps, it comes from a place of love.
You can decide what YOUR highest form of wealth is, but you don’t decide for anyone else.
Thought-provoking though. Thanks
People certainly can choose on their own. But I’d argue they don’t always choose well.
And yes, this is more about my own evolution. As I say in the footnote, there may be something else on the other side of this that I may be missing.
The thing is, freedom enables you to pursue meaning. For many, it is the stepping stone and true path to meaning. Most people are too tied to soul-crushing jobs or the daily grind to find meaning, other than some sort of rationalized acceptance that their cubicle was in fact their destiny.
You're not wrong... freedom can enable the pursuit of meaning. And being trapped in soul-crushing work is hell.
But note what you said there: it's a "stepping stone."
If freedom is a path to meaning, then meaning is the higher thing. (I also don't think you must have freedom for meaning to exist)
My main argument is people frequently mistake the stepping stone for the summit.
I agree to a certain point. To me, freedom is the ability to choose good (good used in the philosophical sense).
I like this framing. Though the popular frame of "freedom" (e.g. financial independence, escape from system, etc.) doesn't usually include your definition of freedom, or would you disagree?
I agree. It's interesting, when I read your article again, you state a few times that you experienced freedom in the sense of financial freedom. So it fits the popular frame of freedom as you state in the comment. We all tend to assume freedom is the ability to choose to do what we want. If what we want is financial independence or escape from the system, very few of us will ever become free. But if we want the highest good, we can all be free right now. We just have to change what we want.
You nailed what I was trying to say - probably more clearly stated than my post 😅
Then again, most people hand-wave me off when I say this and go back to chasing financial freedom, only to delay the real problem a few more decades...
It's human nature. It is much easier to chase the external than to work on our interior life, because it's much easier to gripe about external things than to blame ourselves.
Ironically, we think we have more control over the external > internal, even if the opposite may be true.
Very well stated. I think it becomes more apparent the older we get, too. You can palpably sense it in older people. The cumulative result of our choices to either blame the external or cultivate an interior life. We get either bitter or better the older we get and I believe it is the direct result of consistent choice between these two postures.
Thanks Rick for such an enjoyable read, funny and to-the-point👌It really hit. If this "freedom" we seek means endless resources, no commitment to anything and a perpetual care-free feeling, then that kinda sounds like a life out of touch with reality. Being a blissful butterfly the whole time isn't really possible. We just got to try and create a life that makes sense to us, and is fullfilling enough to keep us going through the not so great parts of it, in touch with the world around us.
Well said!
Same as when you wished all year for summer vacation and then… boredom hits you straight in the face!
Fun fact… one high school summer break I watched Shawshank Redemption 4 times in 2 days 😱
Ahahah impressive!
I appreciate this perspective. I've always thought of freedom as an end unto itself, but maybe it functions more like a means to an end than I originally conceived. There's both freedom from (doing something) and freedom to (do something). In both cases, it's an enabler of something else. Definitely something to reflect on further!
You’ve got it.
Most people’s closest concept of “freedom” = vacation, and when that vacation is so constricted (e.g. max 2 weeks), it’s hard to envision anything different beyond those 2 weeks.
Yes!! Thanks for writing this, Rick. I was also one of those people who sought after freedom as the highest form of wealth. But man, I never realized that freedom --> letting go and that means embracing a void if you don't make up for it with meaning.
I think I'm on the side of wanting to pursue work worth doing all my life (or at least while I derive meaning from it, but work not as in a job but work as in the thing I want to keep doing for the rest of my life).
I happened to be chatting with GPT about my discovery of meaning. Born in a hellish country, freedom was never innate. I burned myself for it, rebuilt my personality, and chose the meaning of my existence. I call this whole process metamorphosis.
Here's my summary:
A person is born carrying a basket.
At first, the basket is filled by others — family, society, the environment. It grows heavy with things that are not truly theirs.
One day, the person feels the weight and decides to set the basket on fire.
The flames consume everything: the borrowed beliefs, the false identity, even the mask they wore as a “self.”
When the fire dies, they stand in the ashes.
Some people pick up only what survived the flames, the few things that are real. Others return to the ruins and rebuild the same basket again, filling it once more with what never belonged to them.
Those who are brave enough may burn it again, and again, until finally the basket holds nothing but what they have chosen for themselves.
This is transformation:
• To discard what was given, even if it feels like losing yourself.
• To pick up only what is true.
• To repeat the fire as many times as necessary until nothing false remains.
Only then do you walk out of the flames, not with what you inherited, but with what you are.
—-
I hope my unique experience can help you. I believe we all live in a shell from birth, and it is the environment that gives us this shell. I think your "meaning" is the feeling of knowing clearly what you need. Thank you for your wonderful article
I like this mental image. Thank you for sharing.
Where I'm less sure (haven't thought through it enough), is whether we need to completely discard 100% of what is given to us. It almost seems impossible, e.g. we inherit so much that we take for granted, and there might be places where we should accept what others give us without discarding it (simple example is scientific truths that I, in no way, will try to refute).
Have you thought about this? When you say "discard what was given," are there any places you shouldn't discard it?
“ Or maybe what you really want is to transcend death in a metaphysical form, but woah!, that’s way too heavy.”
Pretty much. Just waiting and curious to see how it ends.
Likely exactly how it looks like.
The ultimate question!
Very true, Rick! I feel the search for meaning is not so common and I guess it will have it's own quandaries on the emotional journey it'll take one through. Reading your post reminded me of some of this post which I had come across https://offpisteinvesting.com/howard-stevenson-whats-enough/ and I would also recommend some of Alfred Adler's insights from the book "The Courage to be Disliked" of meaning and happiness "Happiness is the feeling of contribution without the need for recognition"
Thanks for the recommendations! Will check them. Out.