This is the opposite of what helped me to stop feeling lost in life. I grew up very goal oriented and executed towards those goals with focus and determination. Around when I turned 40 I realized I wasn't all that happy and I'd spent my entire life so far living for rewards that would come in the future. The problem is that those rewards didn't give sustaining satisfaction. They pass remarkably quickly when you get to them. I stopped feeling lost when I gave up trying to plan my life out and gave up setting goals. Instead I now just trust my instincts and follow what seems interesting or meaningful to me right now. This keeps me living more contentedly in the present and I still get things done.
Having said all that, I came to this realization only after ticking a whole bunch of societal and cultural expectation boxes which means I can afford to take my foot off the gas. Trusting your instincts is a much scarier proposition earlier in life, but I still think it's probably the right thing to do.
My experience would be the opposite. I'm not goal oriented
> Instead I now just trust my instincts and follow what seems interesting or meaningful to me right now
for me that means watching anime, playing video games, reading HN and social media, and maybe writing small programs like solving S.O. questions, And now I look back, have accomplished nothing of significance, and have huge regrets. Regrets that I didn't set goals and work toward them so that I'd be in a better position in my life than I am now.
Not sure the OPs method will change that. In fact the OPs method sounds like using the waterfall method for life planning. That also doesn't sound like it would work for me
Your comment actually suggests that your instincts tell you those things are not as valuable, but you might just be following habit and dopamine loops at the current moment.
Which I guess is to say that GP's "follow your instincts" can also be as difficult as "set goals and hit them", just in different ways.
I feel you. I cannot offer much more than that, but if you care for a friendly advice from someone who is still in the same situation and very much still working on it, setting goals became another way to procrastinate for me.
It is cliche, but system over goals has helped me.. or I guess you could see it as microgoals one does not need to think about much.
Write code for at least X hours per day, read a book for X amount of time, exercise X days a week.
It gives me a checkbox to tick and no overhead in thinking about what goals are achievable, what are desirable.. etc.
I am also used OPs method and it is the reason I now work in a technical job despite having studied art. I just followed my curiosity and that lead to an expert-level understanding in some fields (I later got some formal proof of said expertise).
I don't think that "follow your instinct" is good advice for everyone, but maybe you should understand it more as a "follow your instinct which productive thing you want to do next".
In your examples, writing small programs is the only truly productive thing, the others are consumptive. I learned all I know about programming (I program for a living) from such projects, some of which took weeks of my time. The trick about the instinct thing is that I trust my instincts when I should move to another productive thing that interests me more. So I may be working on a long term programming project, then my instinct tells me when I continue I will start hating it, so I go and work on a hardware project I haven't finished. Before I can switch I need to ensure a state at which I can pick up later on, so I do that before. This way I have a high number of parallel projects each of which is always left in a state where switching between them feels managable.
Of course finishing them is a goal sometimes, but since I am working on many things and always work on the thing that feels good I finish things regularly and have a good time doing it. I also abandon/trash projects, especially if my understanding of a domain has expanded and my initial idea turns out to be misguided. That is okay, I learned something from that which should be your ultimate goal anyways.
I think there's a middle ground between trying to follow a path you set for yourself and thoughtlessly wandering by gut feeling: set a direction you want to go, not a destination.
You'll find that it doesn't require much thought at decision points to choose the options (in aggregate) that push you in that direction. As they say, it's about the journey, not the destination.
With that said, it's still difficult because you have to learn to forego long term expectations and/or acquire discipline not to just "stay put" lest you fall back into the habit of stressing over end goals or the comfort of a stress coping loop (anime, video games, etc), respectively.
Functionally, not completing goals with a long outset is the same as not setting goals. You were banking on completing those goals and not having them just be a myriad of things you've done (which, as you've said, you've already done).
Thank you for sharing this. I am truly glad to hear that this works for you. This resonates a lot with me, and I hope to acquire the same wisdom.
Similarly, as a goal-oriented person I used a variation of the "Waffle House" method, until I turned 40 not long ago. I still have tons of pages in my personal Wiki with life goals, 5-year goals, goals by year, objectives, GTD lists, etc. It served me well, and I am convinced that it is a valid method, up to a point. In big part thanks to this method I also ticked some "societal and cultural expectation boxes". I would cautiously recommend it to younger people too, provided that it matches their personality.
Then, this goal-orientedness fell apart from about age 38 to 40. Having achieved a number of the goals (reasonable ones, nothing to an excess), suddenly all other "goals" turned into a set of stressors. Some - because I doubt I can ever achieve those, others - because I question whether those are what I really want. I accepted the former, but the latter is harder to figure out. This resulted in a 2-year-long haze. The instinctive approach appeals a lot - I would like to think that I have built enough core values to navigate through life intuitively and respecting who I really am. But it also scares, because it sounds like giving up some some control.
Would love to hear the thoughts of those who went through this already. And with all my love, I sincerely wish everyone who reads this to figure out the life!
> Having achieved a number of the goals (reasonable ones, nothing to an excess), suddenly all other "goals" turned into a set of stressors. Some - because I doubt I can ever achieve those, others - because I question whether those are what I really want.
I'm 25 and I relate to this in a funny way. I see todo list apps like this. People say they get a high when ticking off a task but for me once you keep ticking off things, daily, things start to feel not worth it. Life starts to feel like checkboxes.
Going through the same thing. The body knows what it wants, but you can't always be an unthinking autonomaton grabbing stuff willy-nilly off the store shelf. So just feel it out when you need to just sit on the curb and do whatever, or put yourself in a sandbox and say: "I'm going to go... ___to the boardwalk___, then whatever happens, happens."
I went through a very similar thing at around the same age, and one of the insights that really helped me was meditating on impermanence, and cultivating more mental proprioception (awareness of one's subtle thoughts, "mindfulness", whatever you want to call it.
Put simply, it's fine to have goals. But chasing achievement can be unfulfilling. Why? Because all experiences are fleeting. Even if you train for 5 years and win the gold medal, you get to stand on the podium for a few minutes and then life goes on.
It's easy to get people to agree with this intellectually, but you have to really see it on a deep level. There is nothing really to achieve in life. We make goals and cast them out ahead of ourselves in the future, but if that future comes, it doesn't last. We put ourselves on a treadmill of achievement and becoming, then wonder why we feel stressed.
Instead of imagining some future state of completion, work on being aware of how your mind is moving, all the time. Don't chase goals as a way of disproving some fundamental negative assumption about yourself. Don't make happiness contingent on external conditions.
I have the same experience. Until 30 I was one of those people who schedules every hour of their life, used habit trackers religiously, set SMART goals and recorded metrics of how I spent time. I got settled financially/professionally/personally and over the past few years have dropped the old productivity methods. This year I decided to drop the last of them entirely, with great results. Focusing on the moment at hand and following my instincts has made me a lot happier so far, and is still leading to great opportunities.
Maybe it works because we kept our heads down until we were settled, and loosened up after gaining enough experience to develop good instincts? Interesting to hear someone else has taken a similar path with similar results!
idk man, I have the opposite experience. I've always followed my instincts, and am now stuck with consequences of bad decisions that are not easy to undo. My life is good, but I feel like I squandered a real shot to be world class and am now stuck in the top echelon of mediocrity, maybe permanently.
This tracks with my career - highly goal oriented and highly stressful until I sacked it all off for a less intense, more code-focused role a couple of years ago.
What I will say is that the previous decade of goal-driven learning has given me a broad skill set that makes it a lot easier to follow my instincts to success.
I’m not goal oriented and follow my instincts. There’s no way you could get me to write a 5 year plan for myself.
But I will never pick the fork on the road where I will probably be worse off in 5 years. I won’t take a job where I make good money but sit in a corner doing little, for example. I will regret it.
I personally resonate with this take, being a high achiever student in early life and ambitious career seeker into adulthood. While I had my own 'meta' for how to mine certain decades for value (skill buffing, exploration, etc) it is still both scary and liberating to take a step off the planned path knowing deep in your bones it is for the better.
All this middle age crisis stems from having fewer children and even fewer grandchildren.
How to find meaning as childless person: help your relatives (Gen Z and Alpha are in crisis right now), help your community, donate blood, help disabled people, volunteer as firefighter. But above all, focus on doing it to people who are themselves pro-social.
Avoid sociopaths and alert people being abused. Just telling them something along the lines of "be careful with that one" is often enough to break the spell.
I am not sure I agree with not having kids being the cause of mid-life crisis. But for balance, as the GP, I will say that I had two kids through the time that I adjusted my approach to life to this less goal oriented approach. They do provide direction to life, make many decisions easier (since I just choose what’ll be best for them) and provide constant distraction from consumption. They also provide an additional tension if you remain goal oriented though since now you have less time to sit and think about your goals and plans and that’s stressful too.
This may work for the author, and for other people, but I would never give this advice. It supposes you are able to articulate where you want to be in five years, and have the ability to break that down into actionable tasks. Most people just want to have a stable job, apartment/house, and good relationship. Any further breakdown is often guessing, unrealistic, or outright fantasy.
My advice to people in this situation varies tremendously given their background and what they're trying to learn, but it tends towards the same general method: start with something ultra simple and achievable, repeat it a bunch of times (perhaps with some minor variations) until you're relatively comfortable doing it on your own, then begin to branch out. If you're stuck for ideas, show it to somebody else and see what they think; having a training partner or mentor can help you feel less overwhelmed.
Yeah I especially would not expect a lost college student to be able to plan what a solid footing in the industry looks like. If you don't know what a "product manager" is, you're not going to have any idea what a reasonable career path might involve.
It's much better to understand your current position and which direction you're heading in than to have a long-term plan. Good questions for juniors to be asking are stuff like, "how can I get my foot in the door," "how can I tell a good offer from a bad offer," "what can I do to stop being a 'junior' (i.e. how can I become an asset instead of a gamble)"?
I agree. Looking back five years, I couldn't have imagined where I am today.
I like the idea of "effectual" / "working forwards" (rather than "causal" / "working backwards") especially when the future is uncertain. To quote Cedric Chin quoting Saras Sarasvathy (via https://commoncog.com/when-action-beats-prediction/):
> If you use causal thinking, you’ll say something like “ok, we’re making carbonara tonight” and then you will work backwards from the end goal (carbonara for, say, five people) to checking for ingredients in your kitchen, to purchasing the ingredients you don’t have, to prepping and cooking carbonara for your dinner party.
>
> If you use effectual thinking, you’ll say something like “ok, what ingredients and tools do I have right now, and what can I make tonight?” You work forwards from existing resources; the end product is unknown.
>
>In a business context, causal thinking is “we need to increase sales by 12% by the end of the quarter, what levers do I have available to do that?”; effectual thinking is “we have some spare capacity next quarter: one designer and three software engineers, what crazy new thing could we build that might have value for the company?”
It's not for everyone but it works for me - my path has been very path-dependent and I'm glad to be able to chase interesting and unplanned opportunities.
It's worse than that, it assumes that where you want to be in 5 years won't change during that time.
My experience is that our needs and wants change over time, and they are shaped by our actions. Overcommiting to a future that we think we want can end up quite badly in my experience.
The author is working out his personal demons through planning actualization. I hope it works out for him and I would be interested in a followup. In my own experience the best laid plans remain just that..... life is what happens to you while you are busy making other plans.
Did not expect chez cora to make the front page of HN.
People underestimate how important just setting some time aside to think about and commit to a goal is. That part of this post I like, people often overlook that a big part of making a big decision is that commitment and putting yourself in the mind space. The part that I don’t like is trying to pack 5 years of planning into 48 hours and breaking it down to daily goals. If you weren’t overwhelmed before you are now. You don’t know what you don’t know, a week or a month go by and you realize there is a better path or a different but related goal that is actually what you want. Would recommend instead: do the vision quest or whatever you want to call it to either decide you don’t want to do what it is your doing or commit to what it is you are doing. if it is the latter decide on one impactful thing you can start today to get yourself closer, reflect at the end of the week and adjust as needed until you die.
I wrote a toy program once, in which an agent should navigate on its own through a 2D platformer environment. Jump over obstacles/holes, climb stairs, etc.
The idea was that the agent would first receive a goal like "go to tile (15, 28)", then use Dijkstra's algorithm to create a "movement plan" - like "move 2 tiles to the right, trigger a jump, move 3 tiles to the left while in the air", etc - and then execute that plan.
My main takeaway was that even in this small toy world, with clearly defined goals, very simple, deterministic "physics", complete information and an "executor" that is 100% reliable and never gets tired or distracted, it didn't work.
The simplified assumptions about the "physics" in the plan-making stage didn't match how the environment actually behaved, and the agent ended up in a different place than planned after a small number of steps.
What worked was to only execute the first few steps of the plan, then throw the rest away and make a new plan from the new location, then repeat, etc etc.
If this stuff didn't even work in a toy world, with a computer, I can't imagine that making detailed steps for a 5 year period in the real world would work, with the planner having even less knowledge about the world to base their plan on.
I don't think so. A* just let's you add domain knowledge to the process of selecting the next candidate to explore.
But all (classic) pathfinding algorithms "teleport around" in the graph in some way, either switching between different candidate routes or backtracking from a dead-end. That makes it impossible to run the algorithm "live", I.e. have the agent navigate to a location as soon as the algorithm got to it.
In my experience, the best case scenario for students (or anyone) who do these elaborate planning rituals is that it serves as a catharsis that moves their anxieties from their brain to some paper. Relieved, they loosen up and get back to making progress while forgetting about their detailed 5-year plan
The worst case is when this ritual produces a rigid set of unrealistic goals that the person almost immediately fails to achieve. This new sense of failure is compounded on top of existing anxieties and now they’re making even less progress than before while being even more sad about it.
Having supervised high-achieving students in undergrad research settings, I just tell them to chill out, be a whole person with friends and hobbies, and lots of things will just fall into place. The fact that they're where they are (i.e., fancy university, research group, yadda yadda) shows they're the kind of person to take initiative. The fact that they worry shows that they care. They're already way ahead.
The real gains at that point are in connections, reputation, and getting into the habit of physical exercise.
I think the key word here is undergrad research setting. Having an advisor or a department or DGS or Dean breathing down your neck and tumbleweeds in your bank account is an entirely different can of worms.
It seems to me creating a 5y list of daily goals is a recipe to immediately be behind on 1000s on tasks within a few weeks. The thing about estimates is the best case scenario is they take 0 time, worst case is unlimited. When you are planning 5y of tasks when you don't really even know what you're doing, a large majority will completely explode once you dig into them. I've never seen a detailed 5y plan hold up in any area, I'm sceptical to what extent the author has actually done so.
My advice to young people: focus on activities that have some combination of the traits: eventually mandatory, reduce uncertainty about the future, leave open further choices that interest you, benefit you if accomplished sooner.
Yeah this is how it works for me, for sure - as much as I like to frame my penchant for planning and scheduling and lists, the underlying truth is it’s a coping method for anxiety.
There are definitely times where I don’t NEED to plan things out in such a strict detailed way, in order to achieve a good outcome; but i do it anyway because it soothes me.
And as you say, internalizing that ‘approach, not outcome’ and ‘journey, not destination’ outlook is definitely what makes this little arrangement ‘work’ for me. It really helps failures to feel more like learning opportunities, less like let downs or blows to my self-worth.
Grinding out your goals in a 48-hour vision quest-esque process like this, especially for someone early career or facing larger questions about trajectory, seems odd. Five years is an infinite amount of
time for some people and especially so with pace of change and uncertainty these days.
I suppose this might work for some, but it comes
off as excessively performative and not actually practical.
I did something like this a while back, although it didn't take 48 hours. The point is to move you from that infinite five year timeline where decision paralysis is stopping you from doing anything, and taking you back to three years, then one year, then next month, then tomorrow.
I agree with you that five years might as well be a lifetime. The point of this exercise is to define how you want that lifetime to end, then step backwards through it until you know what you're doing tomorrow. The plan for five years ("be a CTO") only matters insofar as it tells you your plan in three years ("be in a position where you report to the board"), one year ("be a lead engineer"), one month ("be confident in passing a job interview and be sending my CV out"), and tomorrow ("message Todd and ask if he'll run a mock interview for me, do some leetcode, message the Acme group chat").
You honestly might as well throw out any plans beyond the one year mark. Either they're important and you can recreate them, or they've changed and you should recreate them. The process of planning is more important than its output.
Readit News
Having said all that, I came to this realization only after ticking a whole bunch of societal and cultural expectation boxes which means I can afford to take my foot off the gas. Trusting your instincts is a much scarier proposition earlier in life, but I still think it's probably the right thing to do.
> Instead I now just trust my instincts and follow what seems interesting or meaningful to me right now
for me that means watching anime, playing video games, reading HN and social media, and maybe writing small programs like solving S.O. questions, And now I look back, have accomplished nothing of significance, and have huge regrets. Regrets that I didn't set goals and work toward them so that I'd be in a better position in my life than I am now.
Not sure the OPs method will change that. In fact the OPs method sounds like using the waterfall method for life planning. That also doesn't sound like it would work for me
Which I guess is to say that GP's "follow your instincts" can also be as difficult as "set goals and hit them", just in different ways.
It is cliche, but system over goals has helped me.. or I guess you could see it as microgoals one does not need to think about much.
Write code for at least X hours per day, read a book for X amount of time, exercise X days a week.
It gives me a checkbox to tick and no overhead in thinking about what goals are achievable, what are desirable.. etc.
I don't think that "follow your instinct" is good advice for everyone, but maybe you should understand it more as a "follow your instinct which productive thing you want to do next".
In your examples, writing small programs is the only truly productive thing, the others are consumptive. I learned all I know about programming (I program for a living) from such projects, some of which took weeks of my time. The trick about the instinct thing is that I trust my instincts when I should move to another productive thing that interests me more. So I may be working on a long term programming project, then my instinct tells me when I continue I will start hating it, so I go and work on a hardware project I haven't finished. Before I can switch I need to ensure a state at which I can pick up later on, so I do that before. This way I have a high number of parallel projects each of which is always left in a state where switching between them feels managable.
Of course finishing them is a goal sometimes, but since I am working on many things and always work on the thing that feels good I finish things regularly and have a good time doing it. I also abandon/trash projects, especially if my understanding of a domain has expanded and my initial idea turns out to be misguided. That is okay, I learned something from that which should be your ultimate goal anyways.
You'll find that it doesn't require much thought at decision points to choose the options (in aggregate) that push you in that direction. As they say, it's about the journey, not the destination.
With that said, it's still difficult because you have to learn to forego long term expectations and/or acquire discipline not to just "stay put" lest you fall back into the habit of stressing over end goals or the comfort of a stress coping loop (anime, video games, etc), respectively.
Similarly, as a goal-oriented person I used a variation of the "Waffle House" method, until I turned 40 not long ago. I still have tons of pages in my personal Wiki with life goals, 5-year goals, goals by year, objectives, GTD lists, etc. It served me well, and I am convinced that it is a valid method, up to a point. In big part thanks to this method I also ticked some "societal and cultural expectation boxes". I would cautiously recommend it to younger people too, provided that it matches their personality.
Then, this goal-orientedness fell apart from about age 38 to 40. Having achieved a number of the goals (reasonable ones, nothing to an excess), suddenly all other "goals" turned into a set of stressors. Some - because I doubt I can ever achieve those, others - because I question whether those are what I really want. I accepted the former, but the latter is harder to figure out. This resulted in a 2-year-long haze. The instinctive approach appeals a lot - I would like to think that I have built enough core values to navigate through life intuitively and respecting who I really am. But it also scares, because it sounds like giving up some some control.
Would love to hear the thoughts of those who went through this already. And with all my love, I sincerely wish everyone who reads this to figure out the life!
I'm 25 and I relate to this in a funny way. I see todo list apps like this. People say they get a high when ticking off a task but for me once you keep ticking off things, daily, things start to feel not worth it. Life starts to feel like checkboxes.
Put simply, it's fine to have goals. But chasing achievement can be unfulfilling. Why? Because all experiences are fleeting. Even if you train for 5 years and win the gold medal, you get to stand on the podium for a few minutes and then life goes on.
It's easy to get people to agree with this intellectually, but you have to really see it on a deep level. There is nothing really to achieve in life. We make goals and cast them out ahead of ourselves in the future, but if that future comes, it doesn't last. We put ourselves on a treadmill of achievement and becoming, then wonder why we feel stressed.
Instead of imagining some future state of completion, work on being aware of how your mind is moving, all the time. Don't chase goals as a way of disproving some fundamental negative assumption about yourself. Don't make happiness contingent on external conditions.
Maybe it works because we kept our heads down until we were settled, and loosened up after gaining enough experience to develop good instincts? Interesting to hear someone else has taken a similar path with similar results!
Grass is always greener, I guess.
Indeed. Everything has to find their own path.
What I will say is that the previous decade of goal-driven learning has given me a broad skill set that makes it a lot easier to follow my instincts to success.
But I will never pick the fork on the road where I will probably be worse off in 5 years. I won’t take a job where I make good money but sit in a corner doing little, for example. I will regret it.
That’s basically my compromise.
How to find meaning as childless person: help your relatives (Gen Z and Alpha are in crisis right now), help your community, donate blood, help disabled people, volunteer as firefighter. But above all, focus on doing it to people who are themselves pro-social.
Avoid sociopaths and alert people being abused. Just telling them something along the lines of "be careful with that one" is often enough to break the spell.
My advice to people in this situation varies tremendously given their background and what they're trying to learn, but it tends towards the same general method: start with something ultra simple and achievable, repeat it a bunch of times (perhaps with some minor variations) until you're relatively comfortable doing it on your own, then begin to branch out. If you're stuck for ideas, show it to somebody else and see what they think; having a training partner or mentor can help you feel less overwhelmed.
It's much better to understand your current position and which direction you're heading in than to have a long-term plan. Good questions for juniors to be asking are stuff like, "how can I get my foot in the door," "how can I tell a good offer from a bad offer," "what can I do to stop being a 'junior' (i.e. how can I become an asset instead of a gamble)"?
I like the idea of "effectual" / "working forwards" (rather than "causal" / "working backwards") especially when the future is uncertain. To quote Cedric Chin quoting Saras Sarasvathy (via https://commoncog.com/when-action-beats-prediction/):
> If you use causal thinking, you’ll say something like “ok, we’re making carbonara tonight” and then you will work backwards from the end goal (carbonara for, say, five people) to checking for ingredients in your kitchen, to purchasing the ingredients you don’t have, to prepping and cooking carbonara for your dinner party. > > If you use effectual thinking, you’ll say something like “ok, what ingredients and tools do I have right now, and what can I make tonight?” You work forwards from existing resources; the end product is unknown. > >In a business context, causal thinking is “we need to increase sales by 12% by the end of the quarter, what levers do I have available to do that?”; effectual thinking is “we have some spare capacity next quarter: one designer and three software engineers, what crazy new thing could we build that might have value for the company?”
It's not for everyone but it works for me - my path has been very path-dependent and I'm glad to be able to chase interesting and unplanned opportunities.
My experience is that our needs and wants change over time, and they are shaped by our actions. Overcommiting to a future that we think we want can end up quite badly in my experience.
This is gold. :)
Did not expect chez cora to make the front page of HN.
The idea was that the agent would first receive a goal like "go to tile (15, 28)", then use Dijkstra's algorithm to create a "movement plan" - like "move 2 tiles to the right, trigger a jump, move 3 tiles to the left while in the air", etc - and then execute that plan.
My main takeaway was that even in this small toy world, with clearly defined goals, very simple, deterministic "physics", complete information and an "executor" that is 100% reliable and never gets tired or distracted, it didn't work.
The simplified assumptions about the "physics" in the plan-making stage didn't match how the environment actually behaved, and the agent ended up in a different place than planned after a small number of steps.
What worked was to only execute the first few steps of the plan, then throw the rest away and make a new plan from the new location, then repeat, etc etc.
If this stuff didn't even work in a toy world, with a computer, I can't imagine that making detailed steps for a 5 year period in the real world would work, with the planner having even less knowledge about the world to base their plan on.
But all (classic) pathfinding algorithms "teleport around" in the graph in some way, either switching between different candidate routes or backtracking from a dead-end. That makes it impossible to run the algorithm "live", I.e. have the agent navigate to a location as soon as the algorithm got to it.
The worst case is when this ritual produces a rigid set of unrealistic goals that the person almost immediately fails to achieve. This new sense of failure is compounded on top of existing anxieties and now they’re making even less progress than before while being even more sad about it.
The real gains at that point are in connections, reputation, and getting into the habit of physical exercise.
My advice to young people: focus on activities that have some combination of the traits: eventually mandatory, reduce uncertainty about the future, leave open further choices that interest you, benefit you if accomplished sooner.
There are definitely times where I don’t NEED to plan things out in such a strict detailed way, in order to achieve a good outcome; but i do it anyway because it soothes me.
And as you say, internalizing that ‘approach, not outcome’ and ‘journey, not destination’ outlook is definitely what makes this little arrangement ‘work’ for me. It really helps failures to feel more like learning opportunities, less like let downs or blows to my self-worth.
I suppose this might work for some, but it comes off as excessively performative and not actually practical.
I agree with you that five years might as well be a lifetime. The point of this exercise is to define how you want that lifetime to end, then step backwards through it until you know what you're doing tomorrow. The plan for five years ("be a CTO") only matters insofar as it tells you your plan in three years ("be in a position where you report to the board"), one year ("be a lead engineer"), one month ("be confident in passing a job interview and be sending my CV out"), and tomorrow ("message Todd and ask if he'll run a mock interview for me, do some leetcode, message the Acme group chat").
You honestly might as well throw out any plans beyond the one year mark. Either they're important and you can recreate them, or they've changed and you should recreate them. The process of planning is more important than its output.
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