So in today's deep dive, I want to talk about the long game. What you can do right now to avoid five or 10 years in the future having regrets or looking back and saying, what have I actually been doing with my time? In other words, what can you do right now so that when you get to the next major milestone in your life, whether that's turning 25 or 30 or 40, you can be content with how things have been going.

This type of advice is different than the type of advice we typically cover on the show. Typically on the show, we're talking about what you can do right now. How do you become more organized right now? How do you avoid distraction in your life right now? How do you make a key career decision that is looming right now?

But when we look to these longer time horizons, how do we make sure that in five years, you're in a place you're really happy about? The advice feels a little different, requires some more patience, requires a little bit more long-term strategy. So that's what I want to do. I have three big ideas I have collected that are all about maximizing where you're going to end up in the intermediate future, making sure that when you get there, you don't feel like the last five or 10 years were wasted, something that just went by on autopilot.

The first idea is annual planning. This is a key bridge between various other scales of planning that we talk about commonly on this show. So probably the most common type of planning we discuss here is multi-scale planning, which is at the key to my advice of staying on top of your various initiatives in your professional life.

So for those who don't know, multi-scale planning talks about three scales. You make a plan at roughly the quarterly or seasonal scale. Here's what I'm working on this fall. That's my goal for this fall. You look at that plan every week to build a weekly plan. All right, here's what I'm working on this week.

The weekly plan is also where you make some adjustments in your calendar. It's also where you see, okay, these are the days I have open time. These are the busy days and you figure out how to make the most of the days actually in front of you. And then your weekly plan is what you look at each day when you make your daily time block plan.

So quarterly, weekly, daily, that's multi-scale planning. That's a key rhythm to being on top of things that need to get done in work and not just being reactive. Approaching each day with your inbox or Slack channel, just driving everything you do. So that's relatively small scale when we're talking about timelines.

We also often talk about on the show a much, much longer time horizon, more abstract type of planning, which we often call lifestyle centric career planning or lifestyle centric visioning where you create this big picture, somewhat abstract vision of where you want your life to eventually be. And it's not just your work, it's where you live, what your day is like, what you're doing with your time, both professionally and non-professionally, your connection to community.

What is your, is it a vision in which you are in a small mountain town having a long walk in the woods with your dog each morning and writing in your field skin notebook? Or is it a vision in which you're in Manhattan and at the interesting underground bar where there's an art show going on and you're connected to this culture of alive art?

You just get this visceral sense of what you want your life to look like, feel like, taste, smell like, all the different senses. And that can be a good guide when you then figure out how you want to make decisions about your life. So that's really future thinking, almost abstractly future thinking.

So we have like, what am I doing in like the weeks ahead? Where do I want to be in the non-specified future? Annual planning is how you actually build a bridge between these two things. As the name implies, it's something you do once a year. I do it on my birthday.

My birthday is in early summer, so that's a good time. Early summer is a good time, late summer, early fall is a good time. Some people do this on New Year's, but you have a consistent time where you do this, and you're able to step back, look at your big picture, lifestyle-centric vision, and say, "What am I doing this year to make bold steps closer to that vision?" And there's two types of things you're going to do in annual planning.

One is going to be making big decisions. This is the right scale to make big decisions that will move you drastically closer to your vision. It is also the time for you to lay out big picture projects or efforts for the year ahead that will also move you more closer to your decision.

So for example, the type of decision you might make is, "I want to change something significant about my job role. I'm going to do that this year. It's going to take me months of setting things up and working on this project over here and sun setting these projects, and I want to start the conversation about this by four months into the year." And this is something that a big decision that might happen on the annual scale.

There might be a major new project you decide, "Okay, now is the time. This year, it's going to take me all year. I'm going to launch this side hustle business venture that's part of this, get me closer to this bigger picture vision where I'm going to move remote or part-time, but this is, I'm going to start this whole project, or this is the year in which I'm going to try to sell my book." And there's a lot of steps that go into that, but I have this sort of big vision for what's going to happen.

Another thing that might happen when you're doing this annual planning is not something you're adding, but something you're taking away. You know what? This thing I'm spending a lot of time on is getting in the way of things that are more important. It's not moving me closer to my big picture lifestyle-centric vision, so I'm going to shutter that side business.

I'm going to sunset this incredibly time-consuming hobby that I've been doing for years, but now is taking more time than it's going to help. At work, I'm going to leave these committees and sort of drastically change what it is that I'm agreeing to work on over here. I'm going to shut down a whole research direction.

So it could be adding something or simplifying, but these are where you make these major decisions and initiate these major projects that are going to move you closer to your vision. So annual planning is a key bridge between the abstract big picture and the very concrete, "What am I working on this week or this month?" That's how you don't get stuck with the vagueness of, like, "I know what my life wants to be like one day," but you're stuck just going through the motions on where it is right now.

The annual planning is the lever that gets you out of that proverbial ditch. Idea number two, leveraging slow compounding of activity. This is something that is true for lots of highly valuable pursuits. To reap the benefit of that pursuit typically requires a large amount of time. In that time, you have to be making consistent action towards that pursuit.

The right way to think about this is like compounding interest. If you look at one of those charts of, "I have $100 and it's compounding monthly at a particular interest rate, how is my money going to grow?" We're used to seeing those charts, those of us who have looked at a financial book or a website, and you see that it grows really slow, and then after a while that picks up steam and then it grows really fast.

As the amount that's compounding gets larger, the amount being added by compounding grows, so the size of the amount of money grows, and then the compounding leaps again, and you have these charts where it takes off pretty quickly after a long period of relatively slow-looking growth. Well, that's the same for a lot of activities that you might undertake.

To adopt the mindset of, "This is a three-year play," and actually for the first year of consistently taking action on this particular interest, objective, or plan, I might not even see large notable returns, but I'm building the base on which the fast compounding is going to happen in the future.

That mindset is critical. That's one of the key ways to take advantage of the five-year window is, "I'm going to launch a small number of actions that I'm going to take consistently for years." That's the type of thing that can really unlock big changes that five years from now you say, "Wow, I'm pretty happy with how things are going." We're used to this in fields that are non-professional.

Eating and exercise is classic. We sort of know this. If we do Chris Hemsworth's diet or exercise plan that he did for the Marvel movies, it's eating a lot of rice and chicken and they exercise two hours a day, two weeks in, you're not going to feel much different, eight months in, you're going to look a lot different.

We're used to it with that. Changing how we eat and exercise, we know the scales there are large. It's not going to be something we'll see in a week, but if we look at the year scale, we're going to see good things. Musical instruments is the other touch point people have familiarity with.

If I practice my guitar once a day, give me two weeks and I'm still going to be pretty bad at guitar. Give me two years, people are like, "Oh, this guy can jam. This guy's pretty good at guitar." We're used to that. We just need to expand that same model to other types of activities that we're not used to thinking about it that way.

For example, building up the ability to read high volume of complicated, interesting material. Here's a 600 page book. Let me get into it. I can read it. I can read it in a week. I can pull out really interesting stuff from it. Here's another book. Let me dive into it.

That is something that you build up with practice. If you have a regular reading habit and you systematically over time increase both the volume and complexity, give that a year and you're going to be a much more adept reader. Mastering a new technology or refining a useful professional skill.

It could be the same thing. I'm working on this a little bit every week. A month from now, I might know a little bit about it. But if I put in this consistent action over a year or two, I could be an expert at this statistical analysis technique, this new microelectronics building and engineering, programming a computer.

Whatever it is, consistent effort over a long enough period of time can get you a really big return. Same thing for even building an intellectual foundation. Hey, it's Cal here. I just wanted to mention, if you want to have help taking action on the type of ideas we talk about in this show, sign up for my email newsletter.

The link is right here below in the description. Two to four times a month, I send out detailed articles about the types of ideas we discuss here. It's the best way to stay connected to me and my audience's quest to live a deeper life. So sign up below. Imagine having a couple of years from now, a really deep and informed political or philosophical or theological foundation on which you're able to pull great insight, shape your understanding of the world and make useful contributions to yourself and the world.

This sounds really appealing. How do you get there? It's effort to learn again and again and again over a long period of time. At first, you're reading a lot of stuff. You don't know a lot of stuff. You don't understand it, but you stick with it for a year or so.

Activity compounds. Expertise grows. That's the second idea. If you don't want to live with regret, then you have to really lean into what can be gained by consistent action over longer time periods than we're comfortable thinking. To do this, you need to make it regular. It needs to be in your weekly plan.

You always remind yourself, this is what I'm doing. The more regular and ritualized it is, the more likely you're actually to keep doing it. Remind yourself every week of why you're doing it. Focus on the process, not the outcome, because it could take a while before the outcomes are good.

Finally, be willing to adjust your approach on roughly the quarterly scale. Look back and say, "Is the rituals I'm using to get better at mastering philosophy or computer programming or microelectronics, is this working or am I spinning my wheels? How can I adjust? Maybe I need to move over to a course or I need to raise the level of challenge." Really at the quarterly scale, constantly be adjusting so that you make sure that you actually are making progress.

The activities you're doing are making progress. The key is give yourself a year or two of this type of consistent, constantly tweaked effort. You'll get good at things. The third idea about making sure you don't end up with regrets is not fearing failure. I often imagine that our lives fall into these grooves on the landscape of possibilities that are low energy.

What's the path of least resistance forward from where we are now? It's like a nuclear particle falling into the lowest energy state. Now it's possible that this least resistance path you fall into is going to lead somewhere deep and satisfying and five, 10 years from now, you'll be happy where you are, but it's relatively arbitrary, so it's probably not going to.

So to get out of this groove, you have to expend a lot of energy. It's going to take a lot of energy to try to push yourself out of this groove and into another one. So you have to be comfortable taking swings in your life in terms of projects you undertake or goals that you pursue that are really difficult and require a lot of energy.

Because if you're not expending a lot of energy, then you have no way of actually getting out of the groove that you're currently in. Things that require a lot of energy, however, tend to be higher stakes. You might succeed or you might fail. If you knew you were going to succeed with it, it's not really that much energy probably that needs to be extended.

It's the idea that I'm taking a swing at this. I'm going to try to take on this new competency in my job that's going to open up a lot of options and it's really hard. I'm going to put myself on the line and say, "Trust me to do this and hold me accountable.

See how much money I brought in. Your stakes here, you could fail. I'm going to try to sell this book. I sold a book. I'm going to write a book. I need to sell a lot of copies of this book. I might not. I might fail at that." It's a higher stake thing.

Higher stake things, you have a symmetry there. The possibility of failure gives you bigger rewards on success. From a psychological perspective, you should be more comfortable undertaking initiatives that have a real risk of notable failure, failure that you would not want to happen because it'd be public or embarrassing or high cost.

If you don't on a semi-regular basis have pursuits of this type, then you are not expending the intensity of energy needed to really change your trajectory in the landscape of possibilities. If you're not expending that energy, there's no way that you're going to be able to easily move yourself into cooler, more interesting tracks.

This is more psychological than I think it is tactical. Just being comfortable with it. "Yeah, I'm going for this. If this fails, I don't want it to, so I'm going to spend a lot of energy." A few of these things will fail, but it's in the expending of energy to avoid failure that you're going to find the successes that actually dislodge you from where you're stuck at the moment.

This is launching a side hustle business, serious attempt to sell a book, maybe outside of your work trying to get a community organization and a community that's important to you up and running successfully. It's hard. This might not work. Try to gather people and be a leader and have this group make a difference.

It might not work. If you're not expending energy towards something where the stakes are high, your chances of having control over where you end up is going to be low. Those are my three ideas if we're thinking about how to avoid regret five years from now. We'll just summarize them.

Use annual planning to bridge your abstract values, ideas, and visions with your concrete planning in the short term. Leverage slow compounding of activity. You want to be willing and comfortable saying, "I'm going to do this for two years regularly, this work or activity or practice because what I want is two years from now where I'm going to be two years from now." That's leveraging compounding of activity.

That's how you get cool things, cool abilities, autonomy, a lot of career capital. That's one of your best tools for doing that on the intermediate time scale. Finally, stop fearing failure. You need to go after things where you don't want to fail because that's the only thing that's going to motivate you to expend enough energy that you have a shot of actually getting unstuck from the grooves where you actually find yourself traveling through life.

Those are my ideas. It's a little different, Jesse. I mean, it's similar to stuff we talk about, but wanting to have an effect tomorrow is a different style of advice than wanting to have an effect on five years from now. The annual planning was a big one for me because otherwise there's such a gap between your abstract vision.

My strategic plan for work, my semester plan, has this vision at the top. It's five properties, but they're abstract, like autonomy and impact. It's these things that are very abstract. I wasn't making progress towards that. If I was, it was haphazard. The annual planning has been such a big change.

Like, "Okay, I'm going to make this move in my career. I'm going to do this with my company this year. I'm going to start this company this year." The annual scale is when that stuff could happen. Some of these big decisions that moved me closer to my vision are too big for, "What am I going to do this fall?" So having that annual scale made a big difference.

You've been doing the annual for how many years? A long time. 20? Probably. I don't know when I started associating with my birthday. I think that was after I had kids because I would consciously take a day on my birthday. What I wanted to do on my birthday was to bring my notebooks and go on a long hike or walk to go through and go through that planning.

So I think once I started having kids is when I really shifted that to my birthday, but it's made a big difference. Now you bring your Remarkable? Now I bring my Remarkable. All the notebooks are there. I think I now have over 20 notebooks in my Remarkable. So it's adding up.

All right. So we want to get the questions here in a second. First I want to talk about one of the sponsors that makes this show possible, and that is our friends at Shopify, a global commerce platform that helps you sell at every stage of your business. We're talking from the launch your online shop stage to the real life store stage, all the way to the did we just hit a million order stage.

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And the customers might not even realize that Shopify technology that's running it. So if you found yourself buying something from someone online and really enjoying the experience, they're probably using Shopify. I mean, I think if we were ever to start an e-commerce corner of our little media empire here, I think Jesse and I both agree it would be Jesse Skeleton related merchandise.

I mean, I think a shirt with like the Jesse Skeleton head and the microphone would be a big seller. Yeah, I think. Right. I mean, I think it'd be awesome. I want like a, either like a shepherd fairy style, like with Obama or like a Che Guevara style poster type thing on the shirt, but it's Jesse Skeleton.

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This is the razor that I use. I love the Hinson guys because their, their course expertise, we've talked about this before, but their core expertise before they got into the razor game and it continues to be one of their core expertise is today is precision milling of parts for the aerospace industry.

We're talking about parts on the Mars rovers or the international space station. So they have these high precision CNC routers that can mill metal to incredible precision. This allows you to build a much better razor. So the Hinson razor is this sort of beautifully milled, I believe it's aluminum where you can put just a standard 10 cent blade, screw it into their razor body.

And because of the precision in which this is manufactured, there is just a less than a human hair width worth of blade extending past the razor body. This gets rid of the wobbly diving board effect that creates nicks that gets things trapped. And so with just one 10 cent blade, you can get a very close shave.

So Hinson razor is what I use because I love having a beautifully constructed tool as opposed to something disposable or plastic. I love that it's cost efficient. You spend more upfront to get this beautiful razor, but because you're using just 10 cent blades and not the 27 vibrating laser power plastic contained blades you buy at the drug store and subscription services, it's very cheap to maintain the razor.

In fact, we will give you if you use a promo code, we'll talk about here in a second, two years worth of blades just for free. When you buy this razor, you won't have to touch shaving equipment for two years because the blades are really cheap. So the cost of running this razor ends up being much less.

So anyways, a big fan of Hinson, love well made tools, love things that also save you money over time. So it's time to say no to subscriptions and yes to a razor that will last you a lifetime. Visit hinsonshaving.com/cal to pick the razor for you and use the code CAL and you'll get two years worth of blades free with your razor.

Just make sure you add the two year supply of blades to your cart. When you go and enter the promo code later, the cost of those will go to zero when you check out. That's 100 free blades when you head to H-E-N-S-O-N-S-H-A-V-I-N-G.com/cal and use the code CAL. You should get the Hinson folks to do, as we build out our Jesse Skeleton store, if we're going to have medallions, which I think we should, like Minto Mori's type medallions, they can mill them to incredible precision.

Because I think that's important. Important use of their material. All right, enough of this nonsense. Let's do some questions. Jesse, who's kicking us off today? Hi, first question from Sophie. What habits do you set up in your life to remind you of how short life really is and not to get trapped in the rat race?

See, this is why we need a Jesse Skeleton Memento Mori medallion that you can just stare at every day and remind yourself life is short. Actually, I think it would have the opposite impact that people would stare at that. It would remind them that entities like Jesse Skeleton exist in this world and they would say, I'm going to go drink.

Like, you know, I might as well just start drinking. That would have the opposite effect. Good question, Sophie. Obviously, this fits with the theme of the today's show, which is how do you avoid looking back with regret on the period of life you just came out of? There's three things I can suggest.

One thing I'm going to point out from our deep dive and two new things I didn't mention in the deep dive. So from the deep dive, you're going to take one thing from that deep dive to make sure that you don't just end up trapped in the rat race and having some regrets is do the annual planning.

All right. Once a year, step back and say, what are what are where am I? Take stock. What are the major decisions I want to make this year that's going to have a drastic change in the trajectory of my life? What major projects or initiatives am I going to work on all year to again have a major impact on the direction of my life?

That's how you avoid getting trapped. In a complacent spiral where years pass by and you say, what did I what was I doing? Why didn't I change things? Annual planning is going to be your best tool there. Here's a couple more tactical things you can do as well. Read heavily.

Good stuff. Interesting stuff. I think exposing yourself to the world of ideas, philosophy and general history, theology, politics, but interesting pushing yourself, complicated stuff. Not the polemical book where someone is like, why the other team is the worst, but, you know, reading the original thinkers that the people that the political books are citing were influenced by this type of thing.

So just exposing yourself to the beauty of ideas and the world and the possibilities that goes a long way to not just getting stuck complacent because it allows you to see the world through an eye of much more sophistication. And then that allows you to pull much more and appreciate much more out of the world.

So you don't want your just as you don't want your decisions to keep you trapped in complacency. You don't want your mind to get trapped in a confined, non-interesting world, abstract cage of mediocre ideas. So read heavily. The third thing I'll recommend is expose yourself to art. And I'm using the word art here a little bit.

Generally, I mean, things where you have incredible creative talents working at their highest level to try to produce things of great value to those who encounter it. So this could be visual arts like painting. This could be really good fiction. This could be movies, for example, which I'm, of course, very interested in.

It could be music. It could even be a really deep appreciation of athletics. There's something about building up a connoisseur like appreciation of something that touches the human spirit when it's executed at the high level that pushes you away from complacency. This is why, for example, I'm very interested in movies and I'm sort of an amateur cinephile and I watch a lot of movies and read a lot about movies.

I derive a lot of inspiration from especially directors who I admire. Just seeing them pushing themselves to create these works that end up having a real impact on people who watch it and build off these prior inspirations pushes me in the other parts of my life. Pushes me out of the tendency like let's just get complacent and publish the deep work for toddler workbook and just sort of get stuck in the wheels.

You see this a lot where people just get stuck in the wheels of like, I don't know, just making my online numbers high. It pushes me out of that. To be exposed to people in a completely other field doing something artistic and really pushing themselves just for the sake of it being more interesting pushes me forward in what I'm doing.

So expose yourself to art as well. The only caveat I would get there is if you are in a creative field, expose yourself to art in a different field. I write about this in my new book, Slow Productivity, which is coming out in March, specifically about my use of movies to help me with my writing.

When you're looking at great work in your own field, that's important to do, but it's not as motivating because it's too close to home. So the motivation also gets covered with other feelings of why am I not doing that? Well, why did that succeed? Oh my God, I'm never going to be able to do that.

There's a real value to actually looking at the art in a completely different field than you're involved in. So you can just appreciate the mindset and the pursuit without getting distracted by the details in the weeds. All right. So annual planning, read heavily, expose yourself to art. All right.

Who do we have next, Jesse? Next question is from Arthur. What are some of the warning signs someone could, should perhaps question their current life, career or happiness? All right. Warning sign number one. If you put a non-trivial amount of time into creating jesseskeleton.com, I think it's a warning sign, Jesse.

That's something you need to reevaluate your life. No, you need to applaud yourself. Let's be honest about that. No, serious question. Okay. How do you know that a change is needed? Well, of course, I'm going to recommend first lifestyle centric career planning. So you want to create this visceral vision of what you want every aspect of your life to be like that resonates with you.

So this involves like what you're doing, where you live, what your day is like, where, who you're interacting with. You have to have this visceral, like you're almost filming a stay in the life scene of a movie of what you want your life to look and feel like. You're looking for concrete scenes in this vision that give you that feeling of, oh yeah.

And it's different for different people. Again, we talked about this earlier in the show. We gave the same example. I mean, for some people, it's like the scene that resonates is they've walked out the door into a trail with their dog to a pond in the middle of these woods where they're going to sit down and they're working on writing something, a notebook.

And other people, it's this, you know, they're in the city and there's this energy to it and there's, they're at a club and listening to this new jazz musician. And there's just different fields, different fields to it for different people. It's these concrete scenes that resonate. So you want to fix that.

You have your lifestyle, ideal vision, ideal lifestyle vision. Now we can decide our major changes needed because probably you're going to find yourself in one of two situations at this point. Situation number one, there is no obvious way to move from where you are right now, close to that vision.

There is no, okay, in what I'm doing right now with where I live, my work, my life, if I can tweak my compass a little bit and make some good decisions, I'm going to move towards that vision. You might be in a situation where like, no, I'm nowhere near it.

I want to be in the woods with my dog writing, you know, Mary Oliver style in a field notes notebook next to the pond. And I'm a banker in Manhattan and it just in the small part, I have, there's no connection from this to that. So you're like, great, let me just tweak this.

And if I do this at my next, no, you're very far from it in that situation. Then yeah, major changes will be needed. Now you know what those changes are aiming for. And you begin to think about, okay, given the career capital I already have given my existing skills, but also my opportunities, like my company, maybe where else do they have satellite offices?

What other types of things can you do with my skills? Where do I have family that, you know, you think through all of your different assets here, metaphorical assets, not financial and figure out how do I best leverage these to move my life closer to the vision and major changes are needed.

I need to lead banking in Manhattan, but I can use these economic skills to do this type of work consulting, you know, whatever is the books for nonprofits. And I could go do this for this company that does it remotely. And if I do this for five years, I could then probably have my own shop after that and get a lot of autonomy.

So if I move from this to this, then I could move after two years to here. And then after five, you start making the plan based on the assets and career capital I have, how do I get closer to the vision? The other situation you might find, however, after identifying your ideal vision is that, okay, I'm proximate.

This is not working for me. This is not working for me. This is working for me. Let's start making some tweaks to get us closer there. I need to take this off my plate, add this. I need to move from this office to that office. I need to, this is fine, but we need to move from this house in the suburb to this house farther out in the countryside.

Okay, that's going to take, I'm going to need a little bit more money in this and that. Okay, that'll take about two years, but I see how this is all going to work. So that's the other case. Like, great, I just need to keep my plans going and my tweaks, but it's not a major change.

I'm just, I see the four or five tweaks I need to make and now I'm much closer to my vision. The key is all of this, both of those scenarios and the specific decisions made in both those scenarios is all driven backwards from a vision. If you're just trying to move forward, what don't I like?

What might I like better? Do I, I don't like this job. What, why I like that job better? If you're just looking down the road and said, I want to turn here, turn there, just looking forward from where you are to the immediate time horizon forward, you have no real focus to these decisions.

You're leaving your path to go on nearby paths. You're haphazardly wandering and hope that you end up somewhere better. But when you're working backwards from this vision that's so visceral and resonates, then you can really make these smarter decisions. And whether it's a major change or not, all that will be very clear because they're for a purpose.

So work backwards from that vision and then you'll see exactly, exactly where you should be. All right, what do we got next, Jesse? Next question's from Max. Most people at the government institution I am working at are comfortable and there are zero expectations of me. I like a lot of things about my working conditions.

I can exercise, work from home, stuff like that. My problem is that now I am under stimulated and I think my potential is slipping away. My vision of deep life is unclear and I feel lost. How do you think I make a vision of the deep life I'm excited for and how do I get my old drive and discipline back?

Well, given your current situation, so your job is easy, you don't mind it, right? So it has none of what in my book, So Good They Can't Ignore You that we call disqualifiers, properties that means you got to get out of this job. It doesn't have any of that.

You're fine with it. I would say let's spend at least a year really working on the other parts of your life. Take advantage of this flexibility that you have in your current job to really get the other parts of your life in order. And really the right way to do this is going to be the deep life stack strategy.

I think it's the right thing to do here. Reclaim your discipline. Okay, here's a I want to reshape yourself as someone who's disciplined, that can do hard things, even if they're not immediately necessary. Do this in multiple parts of your life. Then you want to retune up your values.

What am I really about? What do I care about? What are the rituals that help remind me or connect me to these values? What's the code by which I live? So let's get more serious about this. It's a good time in life to get very serious about this. Then you want to organize.

Okay, now let me get my act together. Let me organize my life at work, my life outside of work. Let me our finances, how we work on household projects, how I sort of organize, pursue, leisurely pursuits, get control over what's going on. You control your time. You control your activity load.

Now you're opening up options. And after you've gone through all of that, now you can say, let's start planning for the remarkable. And even here, I would say, choose one or two things non-professional, remarkable pursuits, and go after that full out. A leisure pursuit, a community pursuit, philosophical, theological, political pursuit.

Have something that's really now taking up your energy that is driving you somewhere remarkable. Do that. Okay, we've moved all the way up to the stack, all the way to the top. Now I would say, let's step back and reassess what's going on with work. And here's where you can really step back and do lifestyle-centered career planning and say like, okay, is there a major change in job that's needed to move me most closer to my ideal lifestyle?

Or is it like, let me just tweak what I'm doing in the government to get rid of some attributes I don't like and kind of move my way towards a position that's just the sweet spot for me. Like I like the work, it's flexible, and just let that be my financial foundation.

I have all this other stuff going on. All that you can work out, I would say, after you go through the deep life stack. What you don't want to do is if your life is ungrounded, to start with a job. That is the concern I have. It is why we introduced a whole deep life stack methodology, is that if you're ungrounded, you've just been wandering through life.

You focus first on your job because that's how you spend most of your time. But to use that as the fulcrum, like, well, this is what's going to heal me. If I make a big swing here, quit the government and start a skeleton medallion company. Big swing, the change itself is going to make me feel better.

This is the key. This is my job is not right. And you haven't worked on any of these other parts of cultivating the deep life. You just end up with a lot of overpaid bills, a garage full of skeleton medallions, and you're just as unhappy as you were before.

The deep life stack methodology is like, let's get a foundation under us. What are we all about? Let's get discipline and control over things. Let's practice pursuing remarkable things and we have that efficacy. Okay, now let's figure out the big vision. And again, you will get clarity once you get there.

I bet you'll end up with tweaking your job. You know, I want to move from here to here. I don't have a managerial role. That's like a lot of meetings, but I could move over here if I'm good and make the right moves. This is like a non managerial role that is going to be better suited.

It's a little bit more autonomous, but also maybe a little bit more interesting. And you can just tweak in there. You're like, this is great. And this is fine. Or maybe you know, you see a vision that involves you doing something completely different. You know, who knows? But I just would say don't start with that.

Start with everything else and then return to return to the job piece. So in the deep life stack methodology, that's why all these changes to your jobs are pretty high up in the stack. It's not that it's not where you start. So I do think that's where people get into trouble sometimes.

All right, let's do a call, Jesse. Yeah, we haven't done a call in a while. Let's cross our fingers. The tech is not easy to live stream these pre-recorded calls, but I think we're gonna make it happen. All right, let's do a call. I'm excited about this. I haven't heard this yet, too.

So this is going to be... Hey, Cal, Philip here. I have a question about how you differentiate between obligations and ambiguous ideas in your weekly planning and task boards. One of the problems I've been having is I've been building a software project that has this ambiguous space of different problems I could be working on.

And mixed in with that are some obligations that have clear, unambiguous problems, like click this button and the page is broken. That's an unambiguous problem. But speed up the site is more of an ambiguous problem. And one of the issues I've been seeing is that my past self can go in and take these ambiguous ideas and turn them into unambiguous tasks to do.

But that when I go in to actually do those tasks, my thinking might have changed or I sometimes went from this problem space to the solution space too quickly. So I wanted to ask, how do you handle some of these ambiguous problems? And at what point do you go from the kind of problem space to the solution space?

I think this could apply to how do you write a book and at what level of ambiguity do you keep things in your task list? And is it okay for there to be a lot of ambiguity in terms of more problem space definition than solution space as you're doing your weekly plans?

Thank you. Well, it's a good question because it does apply to a lot of different types of large projects that have ambiguity about the right way to execute them. So not just software development, he mentioned book writing and there's any other number of problems in there as well. So I think what's key here is you don't want to move from the ambiguous to the concrete too early or too expansively.

So where you get into trouble is where you try to generate a large number of concrete tasks from some sort of ambiguous initiatives and you really populate out your task list with dozens of things. And in some sense, it's weeks of work that you're trying to put into the task list.

Because as you say, it's very difficult to predict ahead of time what are the right things to work on. And your brain knows this. And after a while, these tasks you generated go stale. And then your brain is saying, do I really want to work on this? Is this really important?

This just seems now like an arbitrary game of task whack-a-mole. Here's a task that I put on a list. I get a buzzer and my points go up if I whack it back down. So what you want to do is have a much shorter cycle of concrete task generation.

This is what I'm working on this week. This thing right here is very concrete. I want to find out, here's my load time and I want to make some of these concrete changes to see if I can make my load time better. I can do this in a couple sessions.

This is what they figured out in software development starting in the early 2000s with what's known as agile methodology, where they realized trying to plan out entire software projects from scratch. This and then we'll do this and then we'll do this. They use these things called waterfall diagrams that had the dependencies.

You could have years worth of work all laid out and how long they're going to take. And you could use this to build these detailed budgets of how many hours, programmer hours it was going to take and what the exact timelines would be. And these things never worked. And you would get about a month into these projects.

And then you were just either grimly following these now out of date or stale plans or having to rewrite them. So agile came along and said, just work on one thing at a time. What's the most important next thing we could do right now? Just go do that for like three days and come back.

And let's ask again, what's the most important thing we could do right now? Keep it very short cycle between identifying of a problem, action and back to it. So these more ambiguous things you're talking about should not exist on a task list. This is probably going to be if you use multi-scale planning on your quarterly or some seasonal plan.

Okay, we're working on this software project this fall. We have a vague, vague-ish place where we want to be by the end of the fall. We want a minimal viable product that is available and people are testing it. And that just sits there in your quarterly plan. Then when it comes to your weekly plan, it's like, okay, so what are we working on this week that's going to help us make progress towards this bigger goal?

Well, let me just survey the landscape of issues and come up with one that we can make progress on right now. And then that's just all you're doing and all you care about till that's done. And what they do in Agile methodology is they have a place to collect ideas for this.

So you could have this in your seasonal or quarterly plan. You start collecting ideas. Well, we need to work on loading speed and we need to fix the, here's a button, here's an issue. And you can collect those somewhere. That's fine. You can collect those somewhere, but don't think of those as tasks.

These are just putting pins in various things that might be useful. And you just trust yourself on the small scale when it comes to the weekly scale that you can kind of survey all the different stuff that's out there that you've jotted down that you need to work on or is important that you'll be capable in the small scale of saying of all this stuff, this is a good one to do next.

And let me just do this next. Because one of the things that Agile realizes, you can only do one thing at a time anyway. So it doesn't help to say, I'm doing these five things. It makes you feel better in the moment because you imagine having those five things done, but you can only do one thing at a time.

So might as well do one thing at a time. This applies to a lot of projects. You can collect somewhere your notes or ideas about what needs to happen or issues that need to be resolved. When it comes to having concrete tasks that you're scheduling and they're in your list, it should be what you can work on next.

All right. So just trying to create a huge list of concrete tasks and have them all on your list. I just think that creates a waterfall effect stress. So be okay with these larger projects. Be okay with only a small number of things will make it onto my to do list at a time from this project.

And I trust myself each week to figure out what the best next thing is to do. I don't need everything to be in here. I don't need some more complicated long term planning as well. And so be a little bit more Agile. I think that'll work better. All right.

So as our final part of our question segment here, I want to do a case study. This is where someone writes in explaining or talking about how they applied some ideas from our show in a way that is interesting or successful. The case study I want to report today comes from Mark.

All right. So here's what Mark says. I'm writing a book. It's an academic book in my field, which is musicology. And I've been using Cal's approaches for a couple years now. I've gone from a haphazard researcher writer to a true professional using his approaches. I added a fun new element.

I designed and printed custom writing t shirts for myself. They are just plain black t shirts, but I made a secret label on the inside. It says this black shirt is for creating. And I added a small logo on one sleeve. The rule I have set for myself is that when I put on one of these t shirts, I can't go to sleep again until I do significant writing.

At least an hour, but usually deep work sessions of two to four hours. I definitely don't need these shirts to write, but just like the countless examples Cal has given of other creators going to great lengths to signal to themselves that it's time to create such as Brandon Sanderson's underground layer, which is where he wrote Name of the Wind by the way.

These shirts have been a fun way to get work done and go deep. I've submitted a book proposal, edited two chapters, completed drafts of two more chapters, and I'm halfway through the third chapter now. I have never had more momentum. Well, I appreciate that case study Mark, because I think it does underscore a point we talk about a lot.

Ritual and setting matters when it comes to trying to do hard things with your brain. This is not natural for the human brain to concentrate on symbolic or abstract notions for extended periods of time. So everything we can do to help put our brain into that setting, the better.

So things that seem weird from the outside, a black shirt that has a hidden label that says the shirt is for creating, it seems weird. But you know what else is weird? Sitting down to write a textbook on musicology. This is not something that the Paleolithic human spent a lot of time caring about.

We don't have an evolutionary pressure for it. So the more we think about deep work as a noble, but unusual and demanding activity, I think the more we can embrace unusual rituals and settings to help try to induce those states. So I love hearing these types of examples of people going increasingly over the top to help put themselves and their mind into a deep work mindset.

I think the Brandon Satterson example is great. That's one of my favorites. We talked about this on the show before, but the fantasy writer Brandon Satterson in his suburban house, suburban Utah, in a cul-de-sac, he owned a lot next to it, underground, built this essentially giant bunker, multi-room bunker, completely decked out in a high-end sort of Victorian Gothic decor in which he writes, he has a movie theater down there, he podcasts down there, they have meetings down there for his companies.

I mean, it's completely over the top and unnecessary and just fantastic. If that's your job is to write fantasy, why not have a fantastical place to do it? I mean, just to go to a grim home office and it's just generic and you're at the white desk and you have, you know, laundry baskets in there.

I mean, that's just adding ankle weights to the basketball player. It's an unforced error. You're making the cognitive work you're about to do harder. It doesn't have to be. So embracing the cool and the unusual, I'm always here for that, Jesse, so I'm glad that people send in examples.

So I want to get to a final segment, cool study I want to talk about. First let's mention another sponsor that makes this show possible. This episode is sponsored by BetterHelp. So as we, as we get into in the show a lot, the life of the mind is its own important thing.

I mean, we were just talking about this in the last case study, how the mind is fickle and to do something like convince it to think deeply about a novel for a few hours is something that requires a lot of work. Well because the mind is so fickle, it can also fall into states or configurations that can hold us back.

You might have, for example, constant ruminations, negative ruminations on things that have happened or anxious ruminations of things that are going to happen in the future. You could have these thought patterns that really are making your life harder, making it harder for you to do the things that you really value, that make you feel bad more than you want to feel bad.

Well there are something you can do about this. It turns out that professionals know how to work with your mind and build, rebuild a more comfortable, happy relationship, more sustainable relationship with your mind. This is what you get from professional therapy. Now the problem that a lot of people have, even if they know they could use some help, they want to improve their relationship with their brain is how do I find a therapist?

Is there someone in my town? I mean, what if they're don't take my insurance or they're expensive or they're booked and this is true, especially these days that a lot of therapists, you'll call up their offices and they'll say, we have no openings. How do you get into this world without this huge amount of difficulty up front?

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That's betterhelp.com/deepquestions. Also want to talk about our friends at ExpressVPN. Let me put on my computer science hat for a moment. I wonder what a computer science hat would actually look like. I mean, it would probably have Vulcan ears and somehow a circuit board involved. I don't know. But just imagine I'm wearing a computer science hat because I'm about to get real computer sciencey with you.

You need to be using a VPN. Because what happens is when you connect to the internet, people can see what sites or services you're talking to. If you're in a public wireless access point, anyone nearby can be reading your packets out of the airwaves and know that you are spending an inordinate amount of time on Jesse Skeleton.

And if they figure that out, they're going to call the authorities as they probably should. Same thing even when you're at home. You feel like you have privacy there, but your internet service provider can see what sites and services are you using. They can collect and sell that data to advertisers and believe me, they do.

A VPN protects you from that. With a VPN, instead of connecting directly to the site or service you want to use, you connect instead to a VPN server. You then tell that server with an encrypted message, "Here is who I really want to talk with." And the VPN talks to that site or service on your behalf, encrypts the response and sends it back.

So now the person at the coffee shop or your internet service provider knows nothing about what you're doing other than you're protecting your behavior using a VPN. So you need a VPN. If you're going to use one, I suggest you use the one that I use, which is ExpressVPN.

They've got servers all around the world. There's probably one nearby wherever you happen to be. Or maybe you want to look at content that's only accessible in a certain region. You can connect to a server in that region and get access to that content. So hint, hint, wink, wink.

They have a lot of bandwidth and their software is real easy. You click to turn it on and you use your sites and services, your apps and browsers like normal. All this is happening automatically in the background. So if you want to get three extra months of ExpressVPN for free, when you go to, you will get three extra months free if you go to ExpressVPN.com/deep.

So it's the /deep will give you three extra months for free when you sign up. So it's expressvpn.com/deep. All right. So now we've got to our final segment, a CalReact segment, find something that someone sent me or discovered that I think is worth discussing. And I want to talk about an academic paper that's making the rounds.

Multiple people sent it to me. It has an interesting mathematical idea that I think helps explain a lot of things we experience in real life and gives us some ideas about solutions. So I'm going to load this on the screen. And again, if you're just listening to the show, you can see the show at the deeplife.com/listen episode 271.

The videos are at the bottom of the episode page. All right. So what I have loaded on the page here is a, an economics paper. I don't know if this has been published yet or if it's about to be published, but anyways, the name of the paper is when product markets become collective traps, the case of social media.

I'm going to read you a few sentences here from the abstract. They're going to sound a little bit like academic gobbledygook, but then we're going to decipher them and it's actually going to be somewhat profound. All right. So let me get my, my pen out here. All right. So here we go.

In large scale incentivized experiments with college students, we show that while standard welfare measures, we're over here, suggest a large and positive surplus, our measure accounting for consumption spill overs indicates a negative surplus with a large share of active users deriving negative utility. We also shed light on the drivers of consumption spill overs to non-users in the case of social media and show that in this setting, the fear of missing out plays an important role.

Our framework and estimates highlight the possibility of product market traps where large shares of consumers are trapped in an inefficient equilibrium and would prefer that the product not exist. I'm going to put a box here around the word inefficient equilibrium because I've been using this phraseology quite a bit in my recent talks on technology.

So what does this all mean? Well, these are economists that we're studying in this case, social media use. And they were saying it's confusing. It's confusing sometimes when we directly study the individual user and we see how much they value social media, is the impact positive, is the impact negative?

And it's confusing why we find so much usage. Like why are people using this? If for example, we can measure there's like a negative effect, it's making them less happy. We can see this. And what they're arguing here is, okay, you also have to measure if you really want to understand consumer behavior for a large population, you also have to measure the impact of not using.

And when you integrate the impact of not using, interesting dynamics arise. And their model that they work out here mathematically for social media based on data from experiments with students and incentives and seeing how much they value social media, the model that they derive here says, okay, here's what seems to be happening.

People do not like a lot about social media. We can measure that it directly makes their life negative in many ways. But there is also, especially for talking about young people, a really big cost to being the only person you know, not using it. So the non-user has a big negative cost as well.

And is that non-user cost, which if we're going to use a rational economic model is outweighing the negatives of using it. And that's why we find people stuck on the platform. Now why is this called a collective trap or an inefficient equilibrium is because that negative cost of not using is only incurred if you're the only person to stop using it.

So actually the better configuration in which the total amount of happiness is maximized is one in which most people stop using it. Because then you avoid the negatives you get from being on social media. And if most people are not using it, the negative cost of not using social media dissipates as well.

They point out here in particular with the college students, they study fear of missing out being the main negative cost. If you're not missing out, not being on social media, you lose that negative cost. Then you might as well get rid of the negative cost of using social media.

So why we have so many people using it at the same time that they're so unhappy about it is because they are in an inefficient equilibrium. Now this terminology comes out of the game theory work, the nonlinear dynamics of John Nash, Nobel laureate John Nash, subject of the Russell Crowe movie, A Beautiful Mind, and of course the Sylvia Nassar biography on which that movie was based.

This was the key contribution. This is what won John Nash the Nobel Prize in economics is that he figured out in game theory what happens is you get stuck in these equilibriums, meaning there's no change any individual can make to their strategy to make themselves better off. But the equilibrium is not the best possibility for everyone.

In other words, no one person can make their situation better, but if we all change together, we could be in a better configuration. We're stuck. We call it an inefficient equilibrium because we're far from the maximum positive value that we could be creating, but we can't get to the maximum possible value because no one person can make the change on their own.

If one person leaves, things get worse. This is what social media is in this model. It's an inefficient equilibrium. People are not happy that they're on TikTok all the time or Instagram all the time, but no one individual can make their situation better by leaving the service because then they're missing out because everyone else is on it.

So we're stuck just being mildly unhappy because we want to avoid the even bigger unhappiness of being the odd person out. But this configuration doesn't maximize our possible happiness. We'd all be much happier if we just didn't use it at all. Our total happiness would be much higher, but no one person can get there.

It's inefficient equilibrium. Collective trap is another way of describing this. We're trapped using something we don't like because there's no easy way for us to unilaterally escape it without making things worse. Now, where I think this is particularly relevant in social media, like what is the particularly relevant corollary to this result, is that it really should change the way we think about social media and youth.

We know I've given talks on this. I'm deep into this research literature we've talked about on the show. I have a YouTube video about this. We know there is now a strong signal. There's less debate about this now than there was three years ago. A strong signal that shows increasing social media use leads to increasing mental health negative outcomes for adolescents, especially prepubescent girls.

We know there's this negative impact between social media and youth. And we know that the self-reports from youth say, "This is making me anxious. This is what's making us anxious. It is social media. I don't like social media." Studies like this help us understand why they get stuck because it is an inefficient equilibrium.

It is very difficult for a teenager to be the only teenager in their class who's not using social media. That's even worse. They have to use it and incur these negativities. So if we want to break these collective traps, this is where we can come in and say, "Well, how do we get more than one person not using this?

How do we come in and get most people not using it or large swaths of people not using it? How do we get rid of the negative cost of choosing to say no?" That's where we should put a lot of energy. And this is where schools, for example, being very aggressive about, "We really don't allow phones and we really do not think that kids should have access to social media until they get to this age." And this is where we should be really clear about it matters.

They're not going to change every mind, but if you change 20% of the mind, you can reduce the negative cost of not using and therefore free people from the collective trap. This is where I think cultural suggestions like the current surge in general saying, "You should be 16 before you have unrestricted access to the internet and in particular social media." This is where this is really important because individual students otherwise get stuck into this collective trap where everyone is unhappy and they can't get out of it.

So one way to break the trap is to say, "Okay, let's spring it. No one can use this until they're older." And we've massively increased the positive utility of everyone's experience. There's other places where we see these collective traps or inefficient equilibriums at play in tech and society. The place that I have highlighted often in my work is email in the workplace.

For various reasons, we stumbled into this collaboration style that in my book, "A World Without Email," I call the hyperactive high find where everything is worked out with ad hoc back and forth messaging. This causes huge amounts of problems that I detail often on the show and in my book.

Why does this persist however if it makes people so miserable? Well, it is an inefficient equilibrium. It's a collective trap. If this is how everyone is organizing their work at my office, which is back and forth ad hoc emails, me leaving this unilaterally is going to make things even worse for me because now I'm slowing up decisions.

People are mad at me. My job might be in jeopardy. So the cost of me leaving the hyperactive hive mind by myself is even worse. So I just stick there. The only way to spring the trap in this context is to have the organization itself come in and say, "Enough.

We don't collaborate with back and forth email. Email is for delivering documents. Email is for questions that can be answered with one message. Everything else, here's how we do it." You have to get everyone out of the trap together or we all stay mired in it forever. And so I think collective traps are an important way of understanding techno-social behaviors, especially with a techno-social behavior where we all kind of agree this is bad and it's making us unhappy.

But no one seems to be able to easily leave it. This often is the explanation going on. So this particular paper, again, "When Products Markets Become Collective Traps, the Case for Social Media," interesting paper. I think they're touching on something that is true. For years now, I've been trying to teach audiences about inefficient Nash Equilibriums as an explanation for some of these collective behaviors we see.

So I'm glad there's actually some mathematics now. There's some experimental economics as well that says maybe I was onto something. All right. So that's all the time we have for today. Thank you for listening or watching. Remember, leave a positive review if you like it because we know that helps other people discover it.

We'll be back next week for our Halloween episode of the show. And until then, as always, stay deep. Hey, so if you liked today's episode about playing the long game, I think you might also like episode 254, which is called "The Laws of Less," where we get into how some of the most interesting, impactful, and happy people in the world systematically try to reduce the number of things they're working on.

I think you'll like it. Check it out. So let's make that today's deep question. Why should I do less?