When the student is ready, the teacher appears. And man, did you time this right. Your article really hit home for me. Something I'd like to add, when truly facing your regrets, it also creates an opportunity for gratitude, for the things you did right, for the choices you made that were the right ones. I'm going to pledge to your kickstarter, and look forward to getting my calendar in the mail. (speaking of which, there's a postal strike up here in Canada, just fyi). I only need the last chunk of it (!) but that just makes it all the more urgent. thanks for this, Dave. it's just what I needed.
Hi Laurie, thanks for reading this and glad it home for you. And thanks for pledging for the Kickstarter, I appreciate it! Hopefully the strike will get resolved before the posters ship next year. I like the concept of trying to integrate gratitude somehow. The Tiny Habits author advocates for celebrating your small steps every time you do them. But then in the life-long time frame, it can be nice to review all the good things that happened over the course of your life. Many people have difficult lives but I think everyone can also find things to be grateful for, which is a nice counter-balance to the regrets. Thanks for stopping by!
"Regrets are insights come too late" -- Joseph Campbell
Good stuff as always Dave. 👏 Check out Ernest Becker's "The denial of death" for more about how we distract ourselves from our own mortality.
Rather than thinking about death, using something like your BIG calendar to drive home the finiteness of our life time is a better approach. Dividing life up into four 20 year chapters provides interesting focus and motivation.
Your crisp visuals are very useful to people. Keep goin'!
Thanks Baird! I have not read Becker's book but heard about it, as well as "Terror Management Theory", which gets my vote for the worst branding for a field of psychological study :), especially if you want to scare people away from much needed further research on a subject.
Death is truly a puzzling subject, and depending who you ask, you will receive wildly different feelings about it. "Being in denial" about something is typically frowned upon in psychology, but we seem to make an exception for pondering mortality.
I haven't thought about life in 20 year chapters, but slicing it that way does make for some interesting thoughts about which season you are in, and what one might typically be dealing with during that season.
Very thought provoking. I particularly like (and agree with) befriending time. Words are powerful and finding the correct phrase to generate the best response (the one you want) is imperative. I have worked as a funeral arranger and have a MA in Death, Religion and Culture, as such look at death from a different perspective. But like you, it is a way of befriending time and admitting, then facing, your truth so you can move on unshackled. I am reading Atomic Habits at the moment and must say I am impressed. Motivation that is only obtained from an external source can never be maintained (because it needs a continuous input from said external source- like your Tony Robbins follower). Habit and motivation must come from the inside. Then it can be sustained. James Clear is bang on the money when he talks about how we go about it all wrong with setting goals, the goals are not enduring, it is about changing our identity. Instead of 'I am trying to lose 2 stone' I phrase things now, 'I am a healthy person, would a healthy person eat this'... I shall be dipping back into this article so big thank you Dave. P.S. sorry for the length of my reply!
Through your work and MA I'm sure you've seen the many ways people respond to death. Bronnie Ware's book might be of interest if you haven't read it already.
I am coming to grips with befriending time, it's historically felt like "there's never enough" and "I waste too much of it", but I'm coming around to accepting what it is, and also how I've spent my life thus far. There is an unexpected freedom in befriending it, which has also reduced my feelings of not being and doing enough compared to other people.
Atomic Habits was rightfully a best seller, it debunks common falsehoods about life change and offers some practical tools. It didn't necessarily address my more existential questions about what I should be doing with my life, but deserves a slot for giving people the practical systems needed to actually execute on day to day habits. I did like the self-talk/identity shift improvements too.
I haven't read anything by that author so I will definitely take a look. I think time for me is definitely something I struggle with. My ex used to call me the white rabbit lol. Certainly it would be nice to improve upon that relationship. I am embarking on a 'mosaic career ' as my now partner calls it (he's incredibly supportive). I belive this is another term for your Octopus way and I have heard multipotentialite as well. I breathed a sigh of relief to realise that being like this was 'ok' 😃 thanks for taking the time to read and reply.
Hi Kym, I have not heard the term "mosaic career" but I like it! It does sound like another way to describe an octopus career aka portfolio career. I think interest in these kinds of careers is growing, as people embrace generalism more as a way of being and working. You are not alone :)
It was just something my partner and I had made up 😊 I had not heard of Octopus Career before today. I am really looking forward to seeing more of your articles 😊
Totally agree with the pitfall of refuelling your motivation tank from external sources. Not a big fan of the "weeks before you die" char though, unfortunately :) So much to unpack in this post, thank you!
Hi Evelyn, thanks for reading, glad you found this interesting. Am curious what you don’t like about the calendar, does it feel overwhelming or create anxiety for you? I’m wanting to understand people’s reactions to it better if you have a moment, thanks!
Fair enough, death is an uncomfortable subject for many people. What if I marketed it more like a celebration of life? Sort of like a life scrapbook? I have a friend who wants to use it with his kids to record all the vacations they've taken together, sort of like a travelogue.
That's definitely an angle you can experiment with. I have seen a product exactly like yours online BTW, but it is meant to be a poster only, not a usable calendar/log.
This was great. I think I would add to the list Jed McKenna - he dissects the power of memento mori in his third book, Spiritual Warfare... have you read is books by any chance?
Also check out Arman Khodadoost's recent post on near death experiences for a similar but unique take on this!
Hey Zan, thanks for the recommendations, I have not read either of these authors. That spiritual warfare book sounds interesting and a bit strange too, do I have to read the first two books in the trilogy to understand this one? I also can’t tell if it’s fiction or not-fiction.
Thanks Mia, it is indeed a tough, almost brutal sort of honesty to ask yourself that question, but it's definitely worth doing. Better to do it now while you can do something about it, than on your deathbed when it's too late. Glad you found this interesting!
I like what you've said here, Dave, especially the parts about an 'inciting event'. I think nearly every 'successful' person I've learned about has some form of this, and it's usually traumatic. And of course, I can see it in my own life.
But I see 'befriending time' a little differently. Counting it (in my head, on a chart, wherever) turns me into a clock-watcher, not a time-befriender. Drawing a box around time to represent 'my life' feels like just another way to try and grapple with time.
I saw Burkeman's '4000 Weeks' and just shrugged.
Memento mori? Yes, very useful. The Stoics are onto something.
But I think the Buddhists did it one better: *be present*. In other words, as Ram Dass said: *be here now*.
That's the key to befriending time--because you step *out* of time. Past-time and future-time exist only in your head--they're not real. If you want to befriend time and accept death, the present truly is all that matters.
Hey James, nice to see a fellow small bettor here.
I'm still wrestling with the whole time thing. I get what you're saying, by pondering it too much, it can become its own sort of negative tyranny. But by ignoring it too much, you may regret that you didn't spend it wisely when it's too late to do anything about it. I suppose there's a happy medium somewhere, that probably differs for everyone.
I like the *be present* mantra though, that's definitely something grasp-able.
I'm not sure I know how to optimize 'spending it wisely', you know? How do you define that? And that's worrying about the past and the future, which is the circular trap of anxiety and stress.
But really, being 'present' to me means the ultimate wise use of time, because you're making the most of this very moment. Not that planning doesn't matter, but it's not the primary thing.
Yeah I think the real balance is being in the present while preparing for the future. The past is impossible to change so while you can learn lessons from it, it's less valuable in a sense than the present or future.
I do think some people who only "live for the moment" but do so thoughtlessly fall into a different kind of trap, where they may find themselves in a place they never wanted to be because they were not thinking at all about the future.
But people who can live in the present mindfully (and people interested in Buddhism would presumably fall into this group), might enjoy a rich and meaningful life.
Just getting to grips with your Octopus life and I love the theory, definitely something to ponder.
However, as somebody with an unhealthy amount of anxiety about my mortality that calendar makes me want to curl into a ball, shake and cry until someone invents the means to live forever!
After internal reflection I've aggressively cut down my social use so your plan to reply to each and every substack comment horrifies me. Please look after yourself, you don't need that level of interaction in your life. I would advocate reading Digital Minimalism by Cal Newport, pausing, and then taking a good look at what you get from your technology use.
Thanks James, I appreciate the concern. It's not that onerous to reply to *almost* every comment because I don't get that many, but someday it will definitely become unsustainable, at which time I will pull back. For now I'm enjoying the interactions with people, and do not feel stressed doing it. The moment it becomes a tyranny is the moment I will slow down.
Regarding the calendar I know a lot people don't like to think about death, for a wide variety of reasons. So I don't think the calendar or things like Memento Mori are for everyone. I'm curious why you have such an apprehension about death? Maybe it's too long or complicated an answer for Substack comments, if so that's ok. I've been finding the reactions to the calendar interesting. Some people think it's fascinating and helpful, for others it creates a lot of anxiety.
Great quote! Easier said than done, but I think this is the right lifetime aspiration and place to start. I'd also allow for many other things in life that aren't "death worthy" e.g. fun hobbies. The issue is that most people spend a lifetime distracted by things not really worth living for, then end up regretting it on their death bed.
Yes. It doesn’t have to be sinister or risky . It just has to be something that makes you feel alive and drives you. However, I am familiar with highly competent people in Special Forces or social /community service that have this . They have a drive with a sense of calm . Zanshin , meaning “peaceful readiness “ is the closest I’ve come to it . You can also be driven by other people you love or even your favourite hobby . Might be skiing for some ?
Never heard of Zanshin but I like the sound of it, paired with the Chinese idea of wu-wei (“do without doing”, roughly akin to Flow) is an interesting combination.
Although I still wonder if similar to Ikigai, our western adaptations of these concepts is flawed when viewed through our western lens.
Nevertheless I generally like these ideas of “effortless effort” where due to mastery and preparation, etc we become highly capable at something without much thought and effort.
You hit the nail on its head when you talked about motivation, and how silly it is to go from one motivational speaker to another. The self help industry thrives on people never taking action, and simply letting their brains trick them into thinking they’ve accomplished something just by hearing someone speak. I could go on.
What I really like about this piece is how truthful it is. It’s not easy to come out and say “hey let’s focus on deathbed regrets!”. It’s not easy to hear. But guess what? The fact that people do have deathbed regrets means somewhere along the way, the conventional way of living went wrong. Today’s society tells me to work hard now and enjoy when I’m 60. Well the truth is I may be dead by then. So why wait?
Thanks Nat, it is uncomfortable thinking about death, but when I pondered the discomfort of the regrets I'll likely have at the end of life, it made me realize the discomfort of those regrets will be worse than the discomfort of thinking about death now.
At the Fortune 100 company I worked at, the CEO was a super successful businessman. He was CEO for around 20 years, worked really hard and was well rewarded. He finally stepped down a couple years ago, ready to enjoy a well deserved retirement. But the year he retired, his wife passed away. They were super wealthy, could've traveled or lived anywhere in the world, took up any hobby, bought anything they wanted but she didn't survive long enough to enjoy retirement with him. I don't know them personally but it made me sad that all their plans to live a long and happy retirement wouldn't be materialized. There is no guarantee any of us will live a full life, so we may as well enjoy what we can while we can.
it's also really interesting how different cultures approach/view death (our own and others) - a mortician, Caitlin Doughty wrote books on that (recommend)
Hi Mia, thanks will look Caitlin up. Definitely fascinating about the cultural views on death, I was in Mexico for Day of the Dead, they view death so differently than in the US, if you saw the movie Coco it does a decent job explaining it. And of course religious/spiritual beliefs about the afterlife also add flavor to the mix.
"driven not necessarily from a healthy place, but one of desperation to reverse the esteem-crushing effects of being abused" - oh yes, I feel this as someone who was mentally & emotionally abused by family 🙋🏼♀️
Hi Jessica, sorry to hear about your experience, I don't think this is talked about enough in the context of motivation, drivenness, achievement, etc. as it definitely can play a role. Glad to see you are on a journey of self awareness and growth.
When the student is ready, the teacher appears. And man, did you time this right. Your article really hit home for me. Something I'd like to add, when truly facing your regrets, it also creates an opportunity for gratitude, for the things you did right, for the choices you made that were the right ones. I'm going to pledge to your kickstarter, and look forward to getting my calendar in the mail. (speaking of which, there's a postal strike up here in Canada, just fyi). I only need the last chunk of it (!) but that just makes it all the more urgent. thanks for this, Dave. it's just what I needed.
Hi Laurie, thanks for reading this and glad it home for you. And thanks for pledging for the Kickstarter, I appreciate it! Hopefully the strike will get resolved before the posters ship next year. I like the concept of trying to integrate gratitude somehow. The Tiny Habits author advocates for celebrating your small steps every time you do them. But then in the life-long time frame, it can be nice to review all the good things that happened over the course of your life. Many people have difficult lives but I think everyone can also find things to be grateful for, which is a nice counter-balance to the regrets. Thanks for stopping by!
"Regrets are insights come too late" -- Joseph Campbell
Good stuff as always Dave. 👏 Check out Ernest Becker's "The denial of death" for more about how we distract ourselves from our own mortality.
Rather than thinking about death, using something like your BIG calendar to drive home the finiteness of our life time is a better approach. Dividing life up into four 20 year chapters provides interesting focus and motivation.
Your crisp visuals are very useful to people. Keep goin'!
Hah! Shrinks are the worst at marketing. They're ambivalent about success!
Here's my 5 chapter life model FWIW:
https://bairdbrightman.substack.com/p/the-chapters-of-your-life
Thanks Baird! I have not read Becker's book but heard about it, as well as "Terror Management Theory", which gets my vote for the worst branding for a field of psychological study :), especially if you want to scare people away from much needed further research on a subject.
Death is truly a puzzling subject, and depending who you ask, you will receive wildly different feelings about it. "Being in denial" about something is typically frowned upon in psychology, but we seem to make an exception for pondering mortality.
I haven't thought about life in 20 year chapters, but slicing it that way does make for some interesting thoughts about which season you are in, and what one might typically be dealing with during that season.
Thanks for reading as always!
Very thought provoking. I particularly like (and agree with) befriending time. Words are powerful and finding the correct phrase to generate the best response (the one you want) is imperative. I have worked as a funeral arranger and have a MA in Death, Religion and Culture, as such look at death from a different perspective. But like you, it is a way of befriending time and admitting, then facing, your truth so you can move on unshackled. I am reading Atomic Habits at the moment and must say I am impressed. Motivation that is only obtained from an external source can never be maintained (because it needs a continuous input from said external source- like your Tony Robbins follower). Habit and motivation must come from the inside. Then it can be sustained. James Clear is bang on the money when he talks about how we go about it all wrong with setting goals, the goals are not enduring, it is about changing our identity. Instead of 'I am trying to lose 2 stone' I phrase things now, 'I am a healthy person, would a healthy person eat this'... I shall be dipping back into this article so big thank you Dave. P.S. sorry for the length of my reply!
Hi Kym, no worries, I like long replies :)
Through your work and MA I'm sure you've seen the many ways people respond to death. Bronnie Ware's book might be of interest if you haven't read it already.
I am coming to grips with befriending time, it's historically felt like "there's never enough" and "I waste too much of it", but I'm coming around to accepting what it is, and also how I've spent my life thus far. There is an unexpected freedom in befriending it, which has also reduced my feelings of not being and doing enough compared to other people.
Atomic Habits was rightfully a best seller, it debunks common falsehoods about life change and offers some practical tools. It didn't necessarily address my more existential questions about what I should be doing with my life, but deserves a slot for giving people the practical systems needed to actually execute on day to day habits. I did like the self-talk/identity shift improvements too.
I haven't read anything by that author so I will definitely take a look. I think time for me is definitely something I struggle with. My ex used to call me the white rabbit lol. Certainly it would be nice to improve upon that relationship. I am embarking on a 'mosaic career ' as my now partner calls it (he's incredibly supportive). I belive this is another term for your Octopus way and I have heard multipotentialite as well. I breathed a sigh of relief to realise that being like this was 'ok' 😃 thanks for taking the time to read and reply.
Hi Kym, I have not heard the term "mosaic career" but I like it! It does sound like another way to describe an octopus career aka portfolio career. I think interest in these kinds of careers is growing, as people embrace generalism more as a way of being and working. You are not alone :)
It was just something my partner and I had made up 😊 I had not heard of Octopus Career before today. I am really looking forward to seeing more of your articles 😊
That’s because I made that term up as well! That’s the nice thing about coming up with new ideas, you get to call them whatever you want! 😀
Totally agree with the pitfall of refuelling your motivation tank from external sources. Not a big fan of the "weeks before you die" char though, unfortunately :) So much to unpack in this post, thank you!
Hi Evelyn, thanks for reading, glad you found this interesting. Am curious what you don’t like about the calendar, does it feel overwhelming or create anxiety for you? I’m wanting to understand people’s reactions to it better if you have a moment, thanks!
The calendar feels too morbid.
Fair enough, death is an uncomfortable subject for many people. What if I marketed it more like a celebration of life? Sort of like a life scrapbook? I have a friend who wants to use it with his kids to record all the vacations they've taken together, sort of like a travelogue.
That's definitely an angle you can experiment with. I have seen a product exactly like yours online BTW, but it is meant to be a poster only, not a usable calendar/log.
You've helped me kick-start my Substack planning
Thank Sue, in what way? What are you planning to do with your Substack in 2025?
This was great. I think I would add to the list Jed McKenna - he dissects the power of memento mori in his third book, Spiritual Warfare... have you read is books by any chance?
Also check out Arman Khodadoost's recent post on near death experiences for a similar but unique take on this!
Hey Zan, thanks for the recommendations, I have not read either of these authors. That spiritual warfare book sounds interesting and a bit strange too, do I have to read the first two books in the trilogy to understand this one? I also can’t tell if it’s fiction or not-fiction.
Hey Dave - great questions. It’s a “fictional” story but deals with non-fictional ideas - a bit like a chautauqua.
I suggest reading the books in order, so yes do read the first two before spiritual warfare!
Thanks for this Dave - I added a new question to my nightly project tracker form: If I died tonight, what would I regret?
It'll be really interesting to both contemplate more (and really get in there, not to cop out) and see past answers over time.
Thanks Mia, it is indeed a tough, almost brutal sort of honesty to ask yourself that question, but it's definitely worth doing. Better to do it now while you can do something about it, than on your deathbed when it's too late. Glad you found this interesting!
Such a great summary of the ideas of the authors. I have read them myself and your framework is beautiful.
I like what you've said here, Dave, especially the parts about an 'inciting event'. I think nearly every 'successful' person I've learned about has some form of this, and it's usually traumatic. And of course, I can see it in my own life.
But I see 'befriending time' a little differently. Counting it (in my head, on a chart, wherever) turns me into a clock-watcher, not a time-befriender. Drawing a box around time to represent 'my life' feels like just another way to try and grapple with time.
I saw Burkeman's '4000 Weeks' and just shrugged.
Memento mori? Yes, very useful. The Stoics are onto something.
But I think the Buddhists did it one better: *be present*. In other words, as Ram Dass said: *be here now*.
That's the key to befriending time--because you step *out* of time. Past-time and future-time exist only in your head--they're not real. If you want to befriend time and accept death, the present truly is all that matters.
Hey James, nice to see a fellow small bettor here.
I'm still wrestling with the whole time thing. I get what you're saying, by pondering it too much, it can become its own sort of negative tyranny. But by ignoring it too much, you may regret that you didn't spend it wisely when it's too late to do anything about it. I suppose there's a happy medium somewhere, that probably differs for everyone.
I like the *be present* mantra though, that's definitely something grasp-able.
I'm not sure I know how to optimize 'spending it wisely', you know? How do you define that? And that's worrying about the past and the future, which is the circular trap of anxiety and stress.
But really, being 'present' to me means the ultimate wise use of time, because you're making the most of this very moment. Not that planning doesn't matter, but it's not the primary thing.
Yeah I think the real balance is being in the present while preparing for the future. The past is impossible to change so while you can learn lessons from it, it's less valuable in a sense than the present or future.
I do think some people who only "live for the moment" but do so thoughtlessly fall into a different kind of trap, where they may find themselves in a place they never wanted to be because they were not thinking at all about the future.
But people who can live in the present mindfully (and people interested in Buddhism would presumably fall into this group), might enjoy a rich and meaningful life.
Just getting to grips with your Octopus life and I love the theory, definitely something to ponder.
However, as somebody with an unhealthy amount of anxiety about my mortality that calendar makes me want to curl into a ball, shake and cry until someone invents the means to live forever!
After internal reflection I've aggressively cut down my social use so your plan to reply to each and every substack comment horrifies me. Please look after yourself, you don't need that level of interaction in your life. I would advocate reading Digital Minimalism by Cal Newport, pausing, and then taking a good look at what you get from your technology use.
Thanks James, I appreciate the concern. It's not that onerous to reply to *almost* every comment because I don't get that many, but someday it will definitely become unsustainable, at which time I will pull back. For now I'm enjoying the interactions with people, and do not feel stressed doing it. The moment it becomes a tyranny is the moment I will slow down.
Regarding the calendar I know a lot people don't like to think about death, for a wide variety of reasons. So I don't think the calendar or things like Memento Mori are for everyone. I'm curious why you have such an apprehension about death? Maybe it's too long or complicated an answer for Substack comments, if so that's ok. I've been finding the reactions to the calendar interesting. Some people think it's fascinating and helpful, for others it creates a lot of anxiety.
Thanks for stopping by.
‘Find something to die for , then go live for it ‘
Spot on. Motivation and willpower run out. You need a more intrinsic perpetual fuel source.
Great quote! Easier said than done, but I think this is the right lifetime aspiration and place to start. I'd also allow for many other things in life that aren't "death worthy" e.g. fun hobbies. The issue is that most people spend a lifetime distracted by things not really worth living for, then end up regretting it on their death bed.
Yes. It doesn’t have to be sinister or risky . It just has to be something that makes you feel alive and drives you. However, I am familiar with highly competent people in Special Forces or social /community service that have this . They have a drive with a sense of calm . Zanshin , meaning “peaceful readiness “ is the closest I’ve come to it . You can also be driven by other people you love or even your favourite hobby . Might be skiing for some ?
Never heard of Zanshin but I like the sound of it, paired with the Chinese idea of wu-wei (“do without doing”, roughly akin to Flow) is an interesting combination.
Although I still wonder if similar to Ikigai, our western adaptations of these concepts is flawed when viewed through our western lens.
Nevertheless I generally like these ideas of “effortless effort” where due to mastery and preparation, etc we become highly capable at something without much thought and effort.
Yes, the scientists call it ‘ transient hypofrontality’ 🤪
Not sure if this is better or worse than zanshin/wu-wei 😀
Learn something new everyday!
Beautiful
You hit the nail on its head when you talked about motivation, and how silly it is to go from one motivational speaker to another. The self help industry thrives on people never taking action, and simply letting their brains trick them into thinking they’ve accomplished something just by hearing someone speak. I could go on.
What I really like about this piece is how truthful it is. It’s not easy to come out and say “hey let’s focus on deathbed regrets!”. It’s not easy to hear. But guess what? The fact that people do have deathbed regrets means somewhere along the way, the conventional way of living went wrong. Today’s society tells me to work hard now and enjoy when I’m 60. Well the truth is I may be dead by then. So why wait?
Thanks Nat, it is uncomfortable thinking about death, but when I pondered the discomfort of the regrets I'll likely have at the end of life, it made me realize the discomfort of those regrets will be worse than the discomfort of thinking about death now.
At the Fortune 100 company I worked at, the CEO was a super successful businessman. He was CEO for around 20 years, worked really hard and was well rewarded. He finally stepped down a couple years ago, ready to enjoy a well deserved retirement. But the year he retired, his wife passed away. They were super wealthy, could've traveled or lived anywhere in the world, took up any hobby, bought anything they wanted but she didn't survive long enough to enjoy retirement with him. I don't know them personally but it made me sad that all their plans to live a long and happy retirement wouldn't be materialized. There is no guarantee any of us will live a full life, so we may as well enjoy what we can while we can.
it's also really interesting how different cultures approach/view death (our own and others) - a mortician, Caitlin Doughty wrote books on that (recommend)
Hi Mia, thanks will look Caitlin up. Definitely fascinating about the cultural views on death, I was in Mexico for Day of the Dead, they view death so differently than in the US, if you saw the movie Coco it does a decent job explaining it. And of course religious/spiritual beliefs about the afterlife also add flavor to the mix.
"driven not necessarily from a healthy place, but one of desperation to reverse the esteem-crushing effects of being abused" - oh yes, I feel this as someone who was mentally & emotionally abused by family 🙋🏼♀️
Hi Jessica, sorry to hear about your experience, I don't think this is talked about enough in the context of motivation, drivenness, achievement, etc. as it definitely can play a role. Glad to see you are on a journey of self awareness and growth.
This was a fantastic and well synthesized read, love all your work. I can’t wait to try out the worksheet
Thanks Marco, glad you enjoyed it, and let me know if you have any feedback on the worksheet!