Living A Life Without Regret: 3 Big Things You Need To Know Before 30

00:00:00.000 | So in today's deep dive, I want to talk about the long game.

00:00:06.000 | What you can do right now to avoid five or 10 years in the future having regrets or looking

00:00:13.340 | back and saying, what have I actually been doing with my time?

00:00:15.840 | In other words, what can you do right now so that when you get to the next major milestone

00:00:20.240 | in your life, whether that's turning 25 or 30 or 40, you can be content with how things

00:00:26.240 | have been going.

00:00:28.600 | This type of advice is different than the type of advice we typically cover on the show.

00:00:33.460 | Typically on the show, we're talking about what you can do right now.

00:00:35.720 | How do you become more organized right now?

00:00:38.120 | How do you avoid distraction in your life right now?

00:00:40.560 | How do you make a key career decision that is looming right now?

00:00:44.760 | But when we look to these longer time horizons, how do we make sure that in five years, you're

00:00:51.040 | in a place you're really happy about?

00:00:52.360 | The advice feels a little different, requires some more patience, requires a little bit

00:00:57.320 | more long-term strategy.

00:00:58.600 | So that's what I want to do.

00:00:59.760 | I have three big ideas I have collected that are all about maximizing where you're going

00:01:05.520 | to end up in the intermediate future, making sure that when you get there, you don't feel

00:01:10.480 | like the last five or 10 years were wasted, something that just went by on autopilot.

00:01:17.120 | The first idea is annual planning.

00:01:22.200 | This is a key bridge between various other scales of planning that we talk about commonly

00:01:29.000 | on this show.

00:01:30.120 | So probably the most common type of planning we discuss here is multi-scale planning, which

00:01:34.920 | is at the key to my advice of staying on top of your various initiatives in your professional

00:01:40.720 | life.

00:01:41.720 | So for those who don't know, multi-scale planning talks about three scales.

00:01:44.960 | You make a plan at roughly the quarterly or seasonal scale.

00:01:49.680 | Here's what I'm working on this fall.

00:01:51.440 | That's my goal for this fall.

00:01:52.760 | You look at that plan every week to build a weekly plan.

00:01:55.800 | All right, here's what I'm working on this week.

00:01:58.280 | The weekly plan is also where you make some adjustments in your calendar.

00:02:01.160 | It's also where you see, okay, these are the days I have open time.

00:02:04.200 | These are the busy days and you figure out how to make the most of the days actually

00:02:07.520 | in front of you.

00:02:09.040 | And then your weekly plan is what you look at each day when you make your daily time

00:02:13.320 | block plan.

00:02:14.320 | So quarterly, weekly, daily, that's multi-scale planning.

00:02:19.200 | That's a key rhythm to being on top of things that need to get done in work and not just

00:02:23.640 | being reactive.

00:02:24.640 | Approaching each day with your inbox or Slack channel, just driving everything you do.

00:02:29.080 | So that's relatively small scale when we're talking about timelines.

00:02:33.520 | We also often talk about on the show a much, much longer time horizon, more abstract type

00:02:38.680 | of planning, which we often call lifestyle centric career planning or lifestyle centric

00:02:44.400 | visioning where you create this big picture, somewhat abstract vision of where you want

00:02:49.120 | your life to eventually be.

00:02:50.640 | And it's not just your work, it's where you live, what your day is like, what you're doing

00:02:55.160 | with your time, both professionally and non-professionally, your connection to community.

00:02:59.360 | What is your, is it a vision in which you are in a small mountain town having a long

00:03:05.000 | walk in the woods with your dog each morning and writing in your field skin notebook?

00:03:09.240 | Or is it a vision in which you're in Manhattan and at the interesting underground bar where

00:03:16.000 | there's an art show going on and you're connected to this culture of alive art?

00:03:20.000 | You just get this visceral sense of what you want your life to look like, feel like, taste,

00:03:24.720 | smell like, all the different senses.

00:03:27.320 | And that can be a good guide when you then figure out how you want to make decisions

00:03:30.320 | about your life.

00:03:31.320 | So that's really future thinking, almost abstractly future thinking.

00:03:36.120 | So we have like, what am I doing in like the weeks ahead?

00:03:38.640 | Where do I want to be in the non-specified future?

00:03:42.640 | Annual planning is how you actually build a bridge between these two things.

00:03:47.560 | As the name implies, it's something you do once a year.

00:03:51.600 | I do it on my birthday.

00:03:53.680 | My birthday is in early summer, so that's a good time.

00:03:56.080 | Early summer is a good time, late summer, early fall is a good time.

00:03:58.660 | Some people do this on New Year's, but you have a consistent time where you do this,

00:04:02.800 | and you're able to step back, look at your big picture, lifestyle-centric vision, and

00:04:09.560 | say, "What am I doing this year to make bold steps closer to that vision?"

00:04:15.200 | And there's two types of things you're going to do in annual planning.

00:04:17.480 | One is going to be making big decisions.

00:04:19.180 | This is the right scale to make big decisions that will move you drastically closer to your

00:04:23.440 | vision.

00:04:24.560 | It is also the time for you to lay out big picture projects or efforts for the year ahead

00:04:28.160 | that will also move you more closer to your decision.

00:04:32.080 | So for example, the type of decision you might make is, "I want to change something significant

00:04:38.600 | about my job role.

00:04:40.640 | I'm going to do that this year.

00:04:42.400 | It's going to take me months of setting things up and working on this project over here and

00:04:48.280 | sun setting these projects, and I want to start the conversation about this by four

00:04:53.480 | months into the year."

00:04:54.480 | And this is something that a big decision that might happen on the annual scale.

00:04:58.720 | There might be a major new project you decide, "Okay, now is the time.

00:05:02.600 | This year, it's going to take me all year.

00:05:04.900 | I'm going to launch this side hustle business venture that's part of this, get me closer

00:05:08.560 | to this bigger picture vision where I'm going to move remote or part-time, but this is,

00:05:12.400 | I'm going to start this whole project, or this is the year in which I'm going to try

00:05:15.700 | to sell my book."

00:05:17.680 | And there's a lot of steps that go into that, but I have this sort of big vision for what's

00:05:21.120 | going to happen.

00:05:23.380 | Another thing that might happen when you're doing this annual planning is not something

00:05:25.960 | you're adding, but something you're taking away.

00:05:29.360 | You know what?

00:05:30.440 | This thing I'm spending a lot of time on is getting in the way of things that are more

00:05:34.600 | important.

00:05:35.600 | It's not moving me closer to my big picture lifestyle-centric vision, so I'm going to

00:05:39.800 | shutter that side business.

00:05:41.920 | I'm going to sunset this incredibly time-consuming hobby that I've been doing for years, but

00:05:46.840 | now is taking more time than it's going to help.

00:05:49.800 | At work, I'm going to leave these committees and sort of drastically change what it is

00:05:55.080 | that I'm agreeing to work on over here.

00:05:57.120 | I'm going to shut down a whole research direction.

00:05:59.400 | So it could be adding something or simplifying, but these are where you make these major decisions

00:06:05.080 | and initiate these major projects that are going to move you closer to your vision.

00:06:09.720 | So annual planning is a key bridge between the abstract big picture and the very concrete,

00:06:14.120 | "What am I working on this week or this month?"

00:06:17.520 | That's how you don't get stuck with the vagueness of, like, "I know what my life wants to be

00:06:22.780 | like one day," but you're stuck just going through the motions on where it is right now.

00:06:25.880 | The annual planning is the lever that gets you out of that proverbial ditch.

00:06:33.560 | Idea number two, leveraging slow compounding of activity.

00:06:42.160 | This is something that is true for lots of highly valuable pursuits.

00:06:48.920 | To reap the benefit of that pursuit typically requires a large amount of time.

00:06:56.120 | In that time, you have to be making consistent action towards that pursuit.

00:06:59.680 | The right way to think about this is like compounding interest.

00:07:03.680 | If you look at one of those charts of, "I have $100 and it's compounding monthly at

00:07:09.280 | a particular interest rate, how is my money going to grow?"

00:07:12.720 | We're used to seeing those charts, those of us who have looked at a financial book or

00:07:16.080 | a website, and you see that it grows really slow, and then after a while that picks up

00:07:20.600 | steam and then it grows really fast.

00:07:23.600 | As the amount that's compounding gets larger, the amount being added by compounding grows,

00:07:28.040 | so the size of the amount of money grows, and then the compounding leaps again, and

00:07:32.400 | you have these charts where it takes off pretty quickly after a long period of relatively

00:07:37.920 | slow-looking growth.

00:07:38.920 | Well, that's the same for a lot of activities that you might undertake.

00:07:43.640 | To adopt the mindset of, "This is a three-year play," and actually for the first year of

00:07:49.360 | consistently taking action on this particular interest, objective, or plan, I might not

00:07:54.280 | even see large notable returns, but I'm building the base on which the fast compounding is

00:07:58.760 | going to happen in the future.

00:08:00.000 | That mindset is critical.

00:08:01.920 | That's one of the key ways to take advantage of the five-year window is, "I'm going to

00:08:05.800 | launch a small number of actions that I'm going to take consistently for years."

00:08:11.600 | That's the type of thing that can really unlock big changes that five years from now you say,

00:08:15.400 | "Wow, I'm pretty happy with how things are going."

00:08:19.960 | We're used to this in fields that are non-professional.

00:08:23.480 | Eating and exercise is classic.

00:08:25.760 | We sort of know this.

00:08:28.040 | If we do Chris Hemsworth's diet or exercise plan that he did for the Marvel movies, it's

00:08:34.560 | eating a lot of rice and chicken and they exercise two hours a day, two weeks in, you're

00:08:38.880 | not going to feel much different, eight months in, you're going to look a lot different.

00:08:42.200 | We're used to it with that.

00:08:43.760 | Changing how we eat and exercise, we know the scales there are large.

00:08:46.680 | It's not going to be something we'll see in a week, but if we look at the year scale,

00:08:49.280 | we're going to see good things.

00:08:51.160 | Musical instruments is the other touch point people have familiarity with.

00:08:55.180 | If I practice my guitar once a day, give me two weeks and I'm still going to be pretty

00:09:01.440 | bad at guitar.

00:09:02.880 | Give me two years, people are like, "Oh, this guy can jam.

00:09:06.280 | This guy's pretty good at guitar."

00:09:07.960 | We're used to that.

00:09:09.020 | We just need to expand that same model to other types of activities that we're not used

00:09:13.600 | to thinking about it that way.

00:09:14.720 | For example, building up the ability to read high volume of complicated, interesting material.

00:09:20.360 | Here's a 600 page book.

00:09:21.520 | Let me get into it.

00:09:22.880 | I can read it.

00:09:23.880 | I can read it in a week.

00:09:24.880 | I can pull out really interesting stuff from it.

00:09:26.920 | Here's another book.

00:09:27.920 | Let me dive into it.

00:09:29.360 | That is something that you build up with practice.

00:09:31.440 | If you have a regular reading habit and you systematically over time increase both the

00:09:37.240 | volume and complexity, give that a year and you're going to be a much more adept reader.

00:09:41.640 | Mastering a new technology or refining a useful professional skill.

00:09:44.200 | It could be the same thing.

00:09:46.480 | I'm working on this a little bit every week.

00:09:49.320 | A month from now, I might know a little bit about it.

00:09:51.320 | But if I put in this consistent action over a year or two, I could be an expert at this

00:09:55.120 | statistical analysis technique, this new microelectronics building and engineering, programming a computer.

00:10:03.880 | Whatever it is, consistent effort over a long enough period of time can get you a really

00:10:07.880 | big return.

00:10:08.960 | Same thing for even building an intellectual foundation.

00:10:11.440 | Hey, it's Cal here.

00:10:12.760 | I just wanted to mention, if you want to have help taking action on the type of ideas we

00:10:18.080 | talk about in this show, sign up for my email newsletter.

00:10:22.120 | The link is right here below in the description.

00:10:24.960 | Two to four times a month, I send out detailed articles about the types of ideas we discuss

00:10:30.640 | here.

00:10:31.800 | It's the best way to stay connected to me and my audience's quest to live a deeper life.

00:10:36.960 | So sign up below.

00:10:39.800 | Imagine having a couple of years from now, a really deep and informed political or philosophical

00:10:45.520 | or theological foundation on which you're able to pull great insight, shape your understanding

00:10:50.680 | of the world and make useful contributions to yourself and the world.

00:10:53.760 | This sounds really appealing.

00:10:55.000 | How do you get there?

00:10:56.400 | It's effort to learn again and again and again over a long period of time.

00:11:01.520 | At first, you're reading a lot of stuff.

00:11:02.800 | You don't know a lot of stuff.

00:11:03.800 | You don't understand it, but you stick with it for a year or so.

00:11:07.320 | Activity compounds.

00:11:08.800 | Expertise grows.

00:11:09.800 | That's the second idea.

00:11:11.680 | If you don't want to live with regret, then you have to really lean into what can be gained

00:11:15.120 | by consistent action over longer time periods than we're comfortable thinking.

00:11:19.920 | To do this, you need to make it regular.

00:11:22.320 | It needs to be in your weekly plan.

00:11:24.220 | You always remind yourself, this is what I'm doing.

00:11:26.140 | The more regular and ritualized it is, the more likely you're actually to keep doing

00:11:29.160 | it.

00:11:30.900 | Remind yourself every week of why you're doing it.

00:11:32.960 | Focus on the process, not the outcome, because it could take a while before the outcomes

00:11:36.520 | are good.

00:11:37.520 | Finally, be willing to adjust your approach on roughly the quarterly scale.

00:11:42.580 | Look back and say, "Is the rituals I'm using to get better at mastering philosophy or computer

00:11:47.540 | programming or microelectronics, is this working or am I spinning my wheels?

00:11:51.960 | How can I adjust?

00:11:52.960 | Maybe I need to move over to a course or I need to raise the level of challenge."

00:11:57.720 | Really at the quarterly scale, constantly be adjusting so that you make sure that you

00:12:00.680 | actually are making progress.

00:12:02.760 | The activities you're doing are making progress.

00:12:05.640 | The key is give yourself a year or two of this type of consistent, constantly tweaked

00:12:08.920 | effort.

00:12:09.920 | You'll get good at things.

00:12:12.360 | The third idea about making sure you don't end up with regrets is not fearing failure.

00:12:20.080 | I often imagine that our lives fall into these grooves on the landscape of possibilities

00:12:26.220 | that are low energy.

00:12:28.400 | What's the path of least resistance forward from where we are now?

00:12:32.400 | It's like a nuclear particle falling into the lowest energy state.

00:12:37.960 | Now it's possible that this least resistance path you fall into is going to lead somewhere

00:12:41.280 | deep and satisfying and five, 10 years from now, you'll be happy where you are, but it's

00:12:44.840 | relatively arbitrary, so it's probably not going to.

00:12:48.120 | So to get out of this groove, you have to expend a lot of energy.

00:12:52.840 | It's going to take a lot of energy to try to push yourself out of this groove and into

00:12:56.640 | another one.

00:12:57.640 | So you have to be comfortable taking swings in your life in terms of projects you undertake

00:13:03.880 | or goals that you pursue that are really difficult and require a lot of energy.

00:13:08.040 | Because if you're not expending a lot of energy, then you have no way of actually getting out

00:13:12.160 | of the groove that you're currently in.

00:13:15.560 | Things that require a lot of energy, however, tend to be higher stakes.

00:13:20.680 | You might succeed or you might fail.

00:13:22.800 | If you knew you were going to succeed with it, it's not really that much energy probably

00:13:25.760 | that needs to be extended.

00:13:26.760 | It's the idea that I'm taking a swing at this.

00:13:30.120 | I'm going to try to take on this new competency in my job that's going to open up a lot of

00:13:35.280 | options and it's really hard.

00:13:36.280 | I'm going to put myself on the line and say, "Trust me to do this and hold me accountable.

00:13:39.960 | See how much money I brought in.

00:13:42.160 | Your stakes here, you could fail.

00:13:43.440 | I'm going to try to sell this book.

00:13:44.960 | I sold a book.

00:13:45.960 | I'm going to write a book.

00:13:46.960 | I need to sell a lot of copies of this book.

00:13:48.480 | I might not.

00:13:49.480 | I might fail at that."

00:13:51.840 | It's a higher stake thing.

00:13:53.160 | Higher stake things, you have a symmetry there.

00:13:55.280 | The possibility of failure gives you bigger rewards on success.

00:14:00.120 | From a psychological perspective, you should be more comfortable undertaking initiatives

00:14:07.560 | that have a real risk of notable failure, failure that you would not want to happen

00:14:11.080 | because it'd be public or embarrassing or high cost.

00:14:15.040 | If you don't on a semi-regular basis have pursuits of this type, then you are not expending

00:14:20.720 | the intensity of energy needed to really change your trajectory in the landscape of possibilities.

00:14:26.320 | If you're not expending that energy, there's no way that you're going to be able to easily

00:14:30.200 | move yourself into cooler, more interesting tracks.

00:14:33.920 | This is more psychological than I think it is tactical.

00:14:37.280 | Just being comfortable with it.

00:14:38.280 | "Yeah, I'm going for this.

00:14:39.280 | If this fails, I don't want it to, so I'm going to spend a lot of energy."

00:14:42.680 | A few of these things will fail, but it's in the expending of energy to avoid failure

00:14:46.240 | that you're going to find the successes that actually dislodge you from where you're stuck

00:14:50.440 | at the moment.

00:14:52.760 | This is launching a side hustle business, serious attempt to sell a book, maybe outside

00:14:58.440 | of your work trying to get a community organization and a community that's important to you up

00:15:02.280 | and running successfully.

00:15:03.280 | It's hard.

00:15:04.280 | This might not work.

00:15:05.280 | Try to gather people and be a leader and have this group make a difference.

00:15:07.960 | It might not work.

00:15:10.720 | If you're not expending energy towards something where the stakes are high, your chances of

00:15:16.640 | having control over where you end up is going to be low.

00:15:21.120 | Those are my three ideas if we're thinking about how to avoid regret five years from

00:15:24.280 | now.

00:15:25.280 | We'll just summarize them.

00:15:26.280 | Use annual planning to bridge your abstract values, ideas, and visions with your concrete

00:15:32.280 | planning in the short term.

00:15:35.320 | Leverage slow compounding of activity.

00:15:37.760 | You want to be willing and comfortable saying, "I'm going to do this for two years regularly,

00:15:42.200 | this work or activity or practice because what I want is two years from now where I'm

00:15:45.320 | going to be two years from now."

00:15:46.840 | That's leveraging compounding of activity.

00:15:48.760 | That's how you get cool things, cool abilities, autonomy, a lot of career capital.

00:15:53.420 | That's one of your best tools for doing that on the intermediate time scale.

00:15:56.280 | Finally, stop fearing failure.

00:15:58.160 | You need to go after things where you don't want to fail because that's the only thing

00:16:01.960 | that's going to motivate you to expend enough energy that you have a shot of actually getting

00:16:05.440 | unstuck from the grooves where you actually find yourself traveling through life.

00:16:10.920 | Those are my ideas.

00:16:13.040 | It's a little different, Jesse.

00:16:14.040 | I mean, it's similar to stuff we talk about, but wanting to have an effect tomorrow is

00:16:19.520 | a different style of advice than wanting to have an effect on five years from now.

00:16:24.760 | The annual planning was a big one for me because otherwise there's such a gap between your

00:16:29.880 | abstract vision.

00:16:31.400 | My strategic plan for work, my semester plan, has this vision at the top.

00:16:34.800 | It's five properties, but they're abstract, like autonomy and impact.

00:16:39.200 | It's these things that are very abstract.

00:16:42.320 | I wasn't making progress towards that.

00:16:45.160 | If I was, it was haphazard.

00:16:46.680 | The annual planning has been such a big change.

00:16:48.800 | Like, "Okay, I'm going to make this move in my career.

00:16:52.000 | I'm going to do this with my company this year.

00:16:54.480 | I'm going to start this company this year."

00:16:56.280 | The annual scale is when that stuff could happen.

00:16:59.580 | Some of these big decisions that moved me closer to my vision are too big for, "What

00:17:03.480 | am I going to do this fall?"

00:17:06.840 | So having that annual scale made a big difference.

00:17:10.320 | You've been doing the annual for how many years?

00:17:12.760 | A long time.

00:17:14.760 | 20?

00:17:15.760 | Probably.

00:17:16.760 | I don't know when I started associating with my birthday.

00:17:20.160 | I think that was after I had kids because I would consciously take a day on my birthday.

00:17:24.200 | What I wanted to do on my birthday was to bring my notebooks and go on a long hike or

00:17:28.080 | walk to go through and go through that planning.

00:17:31.040 | So I think once I started having kids is when I really shifted that to my birthday, but

00:17:35.120 | it's made a big difference.

00:17:36.400 | Now you bring your Remarkable?

00:17:37.400 | Now I bring my Remarkable.

00:17:39.920 | All the notebooks are there.

00:17:40.920 | I think I now have over 20 notebooks in my Remarkable.

00:17:44.680 | So it's adding up.

00:17:45.680 | All right.

00:17:46.680 | So we want to get the questions here in a second.

00:17:49.520 | First I want to talk about one of the sponsors that makes this show possible, and that is

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00:18:40.960 | I mean, I think if we were ever to start an e-commerce corner of our little media empire

00:18:46.240 | here, I think Jesse and I both agree it would be Jesse Skeleton related merchandise.

00:18:52.600 | I mean, I think a shirt with like the Jesse Skeleton head and the microphone would be

00:18:57.160 | a big seller.

00:19:00.160 | Yeah, I think.

00:19:01.160 | Right.

00:19:02.160 | I mean, I think it'd be awesome.

00:19:03.160 | I want like a, either like a shepherd fairy style, like with Obama or like a Che Guevara

00:19:08.760 | style poster type thing on the shirt, but it's Jesse Skeleton.

00:19:14.280 | How if we were to do this, which we should, the easiest part of that would be the e-commerce

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00:19:59.440 | That's shopify.com/deep.

00:20:00.440 | I also want to talk about our friends at Hinson Saving.

00:20:05.420 | This is the razor that I use.

00:20:08.160 | I love the Hinson guys because their, their course expertise, we've talked about this

00:20:12.760 | before, but their core expertise before they got into the razor game and it continues to

00:20:16.480 | be one of their core expertise is today is precision milling of parts for the aerospace

00:20:21.720 | industry.

00:20:22.720 | We're talking about parts on the Mars rovers or the international space station.

00:20:26.640 | So they have these high precision CNC routers that can mill metal to incredible precision.

00:20:33.600 | This allows you to build a much better razor.

00:20:36.160 | So the Hinson razor is this sort of beautifully milled, I believe it's aluminum where you

00:20:40.600 | can put just a standard 10 cent blade, screw it into their razor body.

00:20:46.240 | And because of the precision in which this is manufactured, there is just a less than

00:20:50.720 | a human hair width worth of blade extending past the razor body.

00:20:56.100 | This gets rid of the wobbly diving board effect that creates nicks that gets things trapped.

00:21:00.760 | And so with just one 10 cent blade, you can get a very close shave.

00:21:06.440 | So Hinson razor is what I use because I love having a beautifully constructed tool as opposed

00:21:11.720 | to something disposable or plastic.

00:21:13.640 | I love that it's cost efficient.

00:21:16.560 | You spend more upfront to get this beautiful razor, but because you're using just 10 cent

00:21:20.960 | blades and not the 27 vibrating laser power plastic contained blades you buy at the drug

00:21:28.560 | store and subscription services, it's very cheap to maintain the razor.

00:21:33.440 | In fact, we will give you if you use a promo code, we'll talk about here in a second, two

00:21:37.520 | years worth of blades just for free.

00:21:40.440 | When you buy this razor, you won't have to touch shaving equipment for two years because

00:21:46.680 | the blades are really cheap.

00:21:47.680 | So the cost of running this razor ends up being much less.

00:21:49.800 | So anyways, a big fan of Hinson, love well made tools, love things that also save you

00:21:54.480 | money over time.

00:21:55.780 | So it's time to say no to subscriptions and yes to a razor that will last you a lifetime.

00:22:00.400 | Visit hinsonshaving.com/cal to pick the razor for you and use the code CAL and you'll get

00:22:05.560 | two years worth of blades free with your razor.

00:22:07.500 | Just make sure you add the two year supply of blades to your cart.

00:22:10.480 | When you go and enter the promo code later, the cost of those will go to zero when you

00:22:14.780 | check out.

00:22:15.840 | 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.

00:22:24.280 | You should get the Hinson folks to do, as we build out our Jesse Skeleton store, if

00:22:29.800 | we're going to have medallions, which I think we should, like Minto Mori's type medallions,

00:22:35.080 | they can mill them to incredible precision.

00:22:38.360 | Because I think that's important.

00:22:39.360 | Important use of their material.

00:22:40.360 | All right, enough of this nonsense.

00:22:43.360 | Let's do some questions.

00:22:44.360 | Jesse, who's kicking us off today?

00:22:46.040 | Hi, first question from Sophie.

00:22:49.000 | What habits do you set up in your life to remind you of how short life really is and

00:22:52.720 | not to get trapped in the rat race?

00:22:54.760 | See, this is why we need a Jesse Skeleton Memento Mori medallion that you can just stare

00:23:02.000 | at every day and remind yourself life is short.

00:23:05.720 | Actually, I think it would have the opposite impact that people would stare at that.

00:23:10.240 | It would remind them that entities like Jesse Skeleton exist in this world and they would

00:23:15.400 | say, I'm going to go drink.

00:23:16.400 | Like, you know, I might as well just start drinking.

00:23:19.680 | That would have the opposite effect.

00:23:21.880 | Good question, Sophie.

00:23:23.680 | Obviously, this fits with the theme of the today's show, which is how do you avoid looking

00:23:27.920 | back with regret on the period of life you just came out of?

00:23:32.320 | There's three things I can suggest.

00:23:33.840 | One thing I'm going to point out from our deep dive and two new things I didn't mention

00:23:37.080 | in the deep dive.

00:23:38.720 | So from the deep dive, you're going to take one thing from that deep dive to make sure

00:23:43.120 | that you don't just end up trapped in the rat race and having some regrets is do the

00:23:46.440 | annual planning.

00:23:48.840 | All right.

00:23:49.840 | Once a year, step back and say, what are what are where am I?

00:23:53.640 | Take stock.

00:23:54.640 | What are the major decisions I want to make this year that's going to have a drastic change

00:23:58.320 | in the trajectory of my life?

00:23:59.680 | What major projects or initiatives am I going to work on all year to again have a major

00:24:04.680 | impact on the direction of my life?

00:24:06.360 | That's how you avoid getting trapped.

00:24:09.600 | In a complacent spiral where years pass by and you say, what did I what was I doing?

00:24:14.720 | Why didn't I change things?

00:24:16.000 | Annual planning is going to be your best tool there.

00:24:18.600 | Here's a couple more tactical things you can do as well.

00:24:22.000 | Read heavily.

00:24:23.800 | Good stuff.

00:24:24.800 | Interesting stuff.

00:24:26.120 | I think exposing yourself to the world of ideas, philosophy and general history, theology,

00:24:34.760 | politics, but interesting pushing yourself, complicated stuff.

00:24:39.440 | Not the polemical book where someone is like, why the other team is the worst, but, you

00:24:44.000 | know, reading the original thinkers that the people that the political books are citing

00:24:50.080 | were influenced by this type of thing.

00:24:52.320 | So just exposing yourself to the beauty of ideas and the world and the possibilities

00:24:57.960 | that goes a long way to not just getting stuck complacent because it allows you to see the

00:25:02.240 | world through an eye of much more sophistication.

00:25:04.880 | And then that allows you to pull much more and appreciate much more out of the world.

00:25:08.080 | So you don't want your just as you don't want your decisions to keep you trapped in complacency.

00:25:13.720 | You don't want your mind to get trapped in a confined, non-interesting world, abstract

00:25:21.200 | cage of mediocre ideas.

00:25:23.160 | So read heavily.

00:25:24.820 | The third thing I'll recommend is expose yourself to art.

00:25:28.960 | And I'm using the word art here a little bit.

00:25:30.600 | Generally, I mean, things where you have incredible creative talents working at their highest

00:25:37.040 | level to try to produce things of great value to those who encounter it.

00:25:42.720 | So this could be visual arts like painting.

00:25:45.920 | This could be really good fiction.

00:25:47.680 | This could be movies, for example, which I'm, of course, very interested in.

00:25:51.920 | It could be music.

00:25:54.160 | It could even be a really deep appreciation of athletics.

00:25:57.760 | There's something about building up a connoisseur like appreciation of something that touches

00:26:04.960 | the human spirit when it's executed at the high level that pushes you away from complacency.

00:26:12.560 | This is why, for example, I'm very interested in movies and I'm sort of an amateur cinephile

00:26:16.720 | and I watch a lot of movies and read a lot about movies.

00:26:19.040 | I derive a lot of inspiration from especially directors who I admire.

00:26:25.480 | Just seeing them pushing themselves to create these works that end up having a real impact

00:26:29.640 | on people who watch it and build off these prior inspirations pushes me in the other

00:26:33.760 | parts of my life.

00:26:36.280 | Pushes me out of the tendency like let's just get complacent and publish the deep work

00:26:44.440 | for toddler workbook and just sort of get stuck in the wheels.

00:26:48.840 | You see this a lot where people just get stuck in the wheels of like, I don't know, just

00:26:52.160 | making my online numbers high.

00:26:54.440 | It pushes me out of that.

00:26:55.680 | To be exposed to people in a completely other field doing something artistic and really

00:27:00.400 | pushing themselves just for the sake of it being more interesting pushes me forward in

00:27:05.160 | what I'm doing.

00:27:06.400 | So expose yourself to art as well.

00:27:08.180 | The only caveat I would get there is if you are in a creative field, expose yourself to

00:27:11.920 | art in a different field.

00:27:14.240 | I write about this in my new book, Slow Productivity, which is coming out in March, specifically

00:27:19.480 | about my use of movies to help me with my writing.

00:27:23.380 | When you're looking at great work in your own field, that's important to do, but it's

00:27:26.960 | not as motivating because it's too close to home.

00:27:29.720 | So the motivation also gets covered with other feelings of why am I not doing that?

00:27:33.920 | Well, why did that succeed?

00:27:34.920 | Oh my God, I'm never going to be able to do that.

00:27:37.080 | There's a real value to actually looking at the art in a completely different field than

00:27:40.760 | you're involved in.

00:27:41.760 | So you can just appreciate the mindset and the pursuit without getting distracted by

00:27:46.440 | the details in the weeds.

00:27:48.040 | All right.

00:27:49.460 | So annual planning, read heavily, expose yourself to art.

00:27:52.720 | All right.

00:27:53.720 | Who do we have next, Jesse?

00:27:55.340 | Next question is from Arthur.

00:27:56.340 | What are some of the warning signs someone could, should perhaps question their current

00:28:01.120 | life, career or happiness?

00:28:02.920 | All right.

00:28:03.920 | Warning sign number one.

00:28:06.360 | If you put a non-trivial amount of time into creating jesseskeleton.com, I think it's a

00:28:11.480 | warning sign, Jesse.

00:28:12.480 | That's something you need to reevaluate your life.

00:28:15.480 | No, you need to applaud yourself.

00:28:17.240 | Let's be honest about that.

00:28:19.120 | No, serious question.

00:28:20.720 | Okay.

00:28:21.720 | How do you know that a change is needed?

00:28:24.400 | Well, of course, I'm going to recommend first lifestyle centric career planning.

00:28:29.620 | So you want to create this visceral vision of what you want every aspect of your life

00:28:36.400 | to be like that resonates with you.

00:28:38.240 | So this involves like what you're doing, where you live, what your day is like, where, who

00:28:43.540 | you're interacting with.

00:28:45.080 | You have to have this visceral, like you're almost filming a stay in the life scene of

00:28:49.200 | a movie of what you want your life to look and feel like.

00:28:54.180 | You're looking for concrete scenes in this vision that give you that feeling of, oh yeah.

00:29:02.880 | And it's different for different people.

00:29:04.080 | Again, we talked about this earlier in the show.

00:29:05.480 | We gave the same example.

00:29:06.480 | I mean, for some people, it's like the scene that resonates is they've walked out the door

00:29:11.400 | into a trail with their dog to a pond in the middle of these woods where they're going

00:29:15.820 | to sit down and they're working on writing something, a notebook.

00:29:19.080 | And other people, it's this, you know, they're in the city and there's this energy to it

00:29:23.080 | and there's, they're at a club and listening to this new jazz musician.

00:29:26.080 | And there's just different fields, different fields to it for different people.

00:29:29.120 | It's these concrete scenes that resonate.

00:29:30.960 | So you want to fix that.

00:29:33.380 | You have your lifestyle, ideal vision, ideal lifestyle vision.

00:29:38.100 | Now we can decide our major changes needed because probably you're going to find yourself

00:29:42.760 | in one of two situations at this point.

00:29:46.020 | Situation number one, there is no obvious way to move from where you are right now,

00:29:52.960 | close to that vision.

00:29:55.000 | There is no, okay, in what I'm doing right now with where I live, my work, my life, if

00:29:58.960 | I can tweak my compass a little bit and make some good decisions, I'm going to move towards

00:30:04.040 | that vision.

00:30:05.040 | You might be in a situation where like, no, I'm nowhere near it.

00:30:07.640 | I want to be in the woods with my dog writing, you know, Mary Oliver style in a field notes

00:30:13.000 | notebook next to the pond.

00:30:15.120 | And I'm a banker in Manhattan and it just in the small part, I have, there's no connection

00:30:21.440 | from this to that.

00:30:22.440 | So you're like, great, let me just tweak this.

00:30:23.920 | And if I do this at my next, no, you're very far from it in that situation.

00:30:27.800 | Then yeah, major changes will be needed.

00:30:30.480 | Now you know what those changes are aiming for.

00:30:32.280 | And you begin to think about, okay, given the career capital I already have given my

00:30:35.600 | existing skills, but also my opportunities, like my company, maybe where else do they

00:30:40.240 | have satellite offices?

00:30:42.000 | What other types of things can you do with my skills?

00:30:44.080 | Where do I have family that, you know, you think through all of your different assets

00:30:47.560 | here, metaphorical assets, not financial and figure out how do I best leverage these to

00:30:54.200 | move my life closer to the vision and major changes are needed.

00:30:57.560 | I need to lead banking in Manhattan, but I can use these economic skills to do this type

00:31:04.460 | of work consulting, you know, whatever is the books for nonprofits.

00:31:08.560 | And I could go do this for this company that does it remotely.

00:31:11.720 | And if I do this for five years, I could then probably have my own shop after that and get

00:31:15.200 | a lot of autonomy.

00:31:16.560 | So if I move from this to this, then I could move after two years to here.

00:31:20.640 | And then after five, you start making the plan based on the assets and career capital

00:31:25.200 | I have, how do I get closer to the vision?

00:31:26.840 | The other situation you might find, however, after identifying your ideal vision is that,

00:31:31.560 | okay, I'm proximate.

00:31:33.600 | This is not working for me.

00:31:34.600 | This is not working for me.

00:31:35.600 | This is working for me.

00:31:37.640 | Let's start making some tweaks to get us closer there.

00:31:41.520 | I need to take this off my plate, add this.

00:31:45.060 | I need to move from this office to that office.

00:31:46.760 | I need to, this is fine, but we need to move from this house in the suburb to this house

00:31:51.720 | farther out in the countryside.

00:31:53.160 | Okay, that's going to take, I'm going to need a little bit more money in this and that.

00:31:57.280 | Okay, that'll take about two years, but I see how this is all going to work.

00:31:59.960 | So that's the other case.

00:32:01.560 | Like, great, I just need to keep my plans going and my tweaks, but it's not a major

00:32:05.240 | change.

00:32:06.240 | I'm just, I see the four or five tweaks I need to make and now I'm much closer to my

00:32:08.920 | vision.

00:32:09.920 | The key is all of this, both of those scenarios and the specific decisions made in both those

00:32:15.420 | scenarios is all driven backwards from a vision.

00:32:20.020 | If you're just trying to move forward, what don't I like?

00:32:22.200 | What might I like better?

00:32:23.200 | Do I, I don't like this job.

00:32:24.420 | What, why I like that job better?

00:32:25.660 | If you're just looking down the road and said, I want to turn here, turn there, just

00:32:29.540 | looking forward from where you are to the immediate time horizon forward, you have no

00:32:35.180 | real focus to these decisions.

00:32:38.980 | You're leaving your path to go on nearby paths.

00:32:41.180 | You're haphazardly wandering and hope that you end up somewhere better.

00:32:44.960 | But when you're working backwards from this vision that's so visceral and resonates, then

00:32:48.780 | you can really make these smarter decisions.

00:32:50.600 | And whether it's a major change or not, all that will be very clear because they're for

00:32:54.180 | a purpose.

00:32:55.700 | So work backwards from that vision and then you'll see exactly, exactly where you should

00:32:59.580 | be.

00:33:00.580 | All right, what do we got next, Jesse?

00:33:03.620 | Next question's from Max.

00:33:05.960 | Most people at the government institution I am working at are comfortable and there

00:33:09.300 | are zero expectations of me.

00:33:11.460 | I like a lot of things about my working conditions.

00:33:13.620 | I can exercise, work from home, stuff like that.

00:33:16.100 | My problem is that now I am under stimulated and I think my potential is slipping away.

00:33:21.540 | My vision of deep life is unclear and I feel lost.

00:33:25.140 | How do you think I make a vision of the deep life I'm excited for and how do I get my old

00:33:29.820 | drive and discipline back?

00:33:32.060 | Well, given your current situation, so your job is easy, you don't mind it, right?

00:33:37.400 | So it has none of what in my book, So Good They Can't Ignore You that we call disqualifiers,

00:33:43.820 | properties that means you got to get out of this job.

00:33:45.320 | It doesn't have any of that.

00:33:47.220 | You're fine with it.

00:33:48.380 | I would say let's spend at least a year really working on the other parts of your life.

00:33:55.340 | Take advantage of this flexibility that you have in your current job to really get the

00:33:58.760 | other parts of your life in order.

00:34:00.480 | And really the right way to do this is going to be the deep life stack strategy.

00:34:05.800 | I think it's the right thing to do here.

00:34:08.100 | Reclaim your discipline.

00:34:09.100 | Okay, here's a I want to reshape yourself as someone who's disciplined, that can do

00:34:13.260 | hard things, even if they're not immediately necessary.

00:34:16.100 | Do this in multiple parts of your life.

00:34:18.400 | Then you want to retune up your values.

00:34:20.400 | What am I really about?

00:34:21.400 | What do I care about?

00:34:22.660 | What are the rituals that help remind me or connect me to these values?

00:34:26.300 | What's the code by which I live?

00:34:27.980 | So let's get more serious about this.

00:34:28.980 | It's a good time in life to get very serious about this.

00:34:32.340 | Then you want to organize.

00:34:33.900 | Okay, now let me get my act together.

00:34:35.860 | Let me organize my life at work, my life outside of work.

00:34:39.140 | Let me our finances, how we work on household projects, how I sort of organize, pursue,

00:34:44.380 | leisurely pursuits, get control over what's going on.

00:34:47.020 | You control your time.

00:34:48.540 | You control your activity load.

00:34:50.500 | Now you're opening up options.

00:34:52.860 | And after you've gone through all of that, now you can say, let's start planning for

00:34:58.260 | the remarkable.

00:34:59.260 | And even here, I would say, choose one or two things non-professional, remarkable pursuits,

00:35:03.980 | and go after that full out.

00:35:05.620 | A leisure pursuit, a community pursuit, philosophical, theological, political pursuit.

00:35:12.180 | Have something that's really now taking up your energy that is driving you somewhere

00:35:17.460 | remarkable.

00:35:18.460 | Do that.

00:35:19.460 | Okay, we've moved all the way up to the stack, all the way to the top.

00:35:24.140 | Now I would say, let's step back and reassess what's going on with work.

00:35:29.260 | And here's where you can really step back and do lifestyle-centered career planning

00:35:32.700 | and say like, okay, is there a major change in job that's needed to move me most closer

00:35:37.740 | to my ideal lifestyle?

00:35:39.580 | Or is it like, let me just tweak what I'm doing in the government to get rid of some

00:35:43.020 | attributes I don't like and kind of move my way towards a position that's just the sweet

00:35:46.700 | spot for me.

00:35:47.700 | Like I like the work, it's flexible, and just let that be my financial foundation.

00:35:50.860 | I have all this other stuff going on.

00:35:52.580 | All that you can work out, I would say, after you go through the deep life stack.

00:35:55.820 | What you don't want to do is if your life is ungrounded, to start with a job.

00:36:02.500 | That is the concern I have.

00:36:03.860 | It is why we introduced a whole deep life stack methodology, is that if you're ungrounded,

00:36:08.100 | you've just been wandering through life.

00:36:10.900 | You focus first on your job because that's how you spend most of your time.

00:36:13.580 | But to use that as the fulcrum, like, well, this is what's going to heal me.

00:36:17.540 | If I make a big swing here, quit the government and start a skeleton medallion company.

00:36:25.860 | Big swing, the change itself is going to make me feel better.

00:36:30.340 | This is the key.

00:36:31.340 | This is my job is not right.

00:36:32.340 | And you haven't worked on any of these other parts of cultivating the deep life.

00:36:35.540 | You just end up with a lot of overpaid bills, a garage full of skeleton medallions, and

00:36:41.100 | you're just as unhappy as you were before.

00:36:43.060 | The deep life stack methodology is like, let's get a foundation under us.

00:36:45.940 | What are we all about?

00:36:46.940 | Let's get discipline and control over things.

00:36:48.700 | Let's practice pursuing remarkable things and we have that efficacy.

00:36:51.980 | Okay, now let's figure out the big vision.

00:36:56.860 | And again, you will get clarity once you get there.

00:36:59.780 | I bet you'll end up with tweaking your job.

00:37:04.460 | You know, I want to move from here to here.

00:37:07.460 | I don't have a managerial role.

00:37:09.240 | That's like a lot of meetings, but I could move over here if I'm good and make the right

00:37:14.140 | moves.

00:37:15.140 | This is like a non managerial role that is going to be better suited.

00:37:18.980 | It's a little bit more autonomous, but also maybe a little bit more interesting.

00:37:22.220 | And you can just tweak in there.

00:37:23.300 | You're like, this is great.

00:37:24.300 | And this is fine.

00:37:25.700 | Or maybe you know, you see a vision that involves you doing something completely different.

00:37:28.700 | You know, who knows?

00:37:29.700 | But I just would say don't start with that.

00:37:32.100 | Start with everything else and then return to return to the job piece.

00:37:37.260 | So in the deep life stack methodology, that's why all these changes to your jobs are pretty

00:37:40.240 | high up in the stack.

00:37:42.380 | It's not that it's not where you start.

00:37:43.940 | So I do think that's where people get into trouble sometimes.

00:37:48.980 | All right, let's do a call, Jesse.

00:37:51.220 | Yeah, we haven't done a call in a while.

00:37:52.860 | Let's cross our fingers.

00:37:54.740 | The tech is not easy to live stream these pre-recorded calls, but I think we're gonna

00:38:01.460 | make it happen.

00:38:02.460 | All right, let's do a call.

00:38:03.460 | I'm excited about this.

00:38:04.460 | I haven't heard this yet, too.

00:38:05.460 | So this is going to be...

00:38:06.460 | Hey, Cal, Philip here.

00:38:07.460 | I have a question about how you differentiate between obligations and ambiguous ideas in

00:38:15.700 | your weekly planning and task boards.

00:38:18.580 | One of the problems I've been having is I've been building a software project that has

00:38:22.820 | this ambiguous space of different problems I could be working on.

00:38:27.780 | And mixed in with that are some obligations that have clear, unambiguous problems, like

00:38:35.460 | click this button and the page is broken.

00:38:37.440 | That's an unambiguous problem.

00:38:39.260 | But speed up the site is more of an ambiguous problem.

00:38:42.180 | And one of the issues I've been seeing is that my past self can go in and take these

00:38:48.260 | ambiguous ideas and turn them into unambiguous tasks to do.

00:38:53.940 | But that when I go in to actually do those tasks, my thinking might have changed or I

00:38:59.020 | sometimes went from this problem space to the solution space too quickly.

00:39:04.340 | So I wanted to ask, how do you handle some of these ambiguous problems?

00:39:09.500 | And at what point do you go from the kind of problem space to the solution space?

00:39:14.140 | I think this could apply to how do you write a book and at what level of ambiguity do you

00:39:18.740 | keep things in your task list?

00:39:20.700 | And is it okay for there to be a lot of ambiguity in terms of more problem space definition

00:39:25.620 | than solution space as you're doing your weekly plans?

00:39:28.300 | Thank you.

00:39:29.300 | Well, it's a good question because it does apply to a lot of different types of large

00:39:33.500 | projects that have ambiguity about the right way to execute them.

00:39:36.940 | So not just software development, he mentioned book writing and there's any other number

00:39:41.280 | of problems in there as well.

00:39:43.900 | So I think what's key here is you don't want to move from the ambiguous to the concrete

00:39:50.700 | too early or too expansively.

00:39:54.560 | So where you get into trouble is where you try to generate a large number of concrete

00:39:59.900 | tasks from some sort of ambiguous initiatives and you really populate out your task list

00:40:05.340 | with dozens of things.

00:40:06.540 | And in some sense, it's weeks of work that you're trying to put into the task list.

00:40:10.220 | Because as you say, it's very difficult to predict ahead of time what are the right things

00:40:14.320 | to work on.

00:40:15.320 | And your brain knows this.

00:40:16.320 | And after a while, these tasks you generated go stale.

00:40:19.940 | And then your brain is saying, do I really want to work on this?

00:40:22.180 | Is this really important?

00:40:23.260 | This just seems now like an arbitrary game of task whack-a-mole.

00:40:26.460 | Here's a task that I put on a list.

00:40:28.180 | I get a buzzer and my points go up if I whack it back down.

00:40:33.220 | So what you want to do is have a much shorter cycle of concrete task generation.

00:40:39.020 | This is what I'm working on this week.

00:40:41.460 | This thing right here is very concrete.

00:40:45.100 | I want to find out, here's my load time and I want to make some of these concrete changes

00:40:49.780 | to see if I can make my load time better.

00:40:51.180 | I can do this in a couple sessions.

00:40:53.020 | This is what they figured out in software development starting in the early 2000s with

00:40:57.380 | what's known as agile methodology, where they realized trying to plan out entire software

00:41:02.620 | projects from scratch.

00:41:04.860 | This and then we'll do this and then we'll do this.

00:41:06.620 | They use these things called waterfall diagrams that had the dependencies.

00:41:10.620 | You could have years worth of work all laid out and how long they're going to take.

00:41:14.860 | And you could use this to build these detailed budgets of how many hours, programmer hours

00:41:19.940 | it was going to take and what the exact timelines would be.

00:41:22.780 | And these things never worked.

00:41:23.780 | And you would get about a month into these projects.

00:41:25.580 | And then you were just either grimly following these now out of date or stale plans or having

00:41:30.700 | to rewrite them.

00:41:31.700 | So agile came along and said, just work on one thing at a time.

00:41:35.700 | What's the most important next thing we could do right now?

00:41:38.060 | Just go do that for like three days and come back.

00:41:40.020 | And let's ask again, what's the most important thing we could do right now?

00:41:43.060 | Keep it very short cycle between identifying of a problem, action and back to it.

00:41:49.100 | So these more ambiguous things you're talking about should not exist on a task list.

00:41:53.140 | This is probably going to be if you use multi-scale planning on your quarterly or some seasonal

00:41:58.660 | plan.

00:41:59.660 | Okay, we're working on this software project this fall.

00:42:02.940 | We have a vague, vague-ish place where we want to be by the end of the fall.

00:42:07.740 | We want a minimal viable product that is available and people are testing it.

00:42:12.540 | And that just sits there in your quarterly plan.

00:42:15.260 | Then when it comes to your weekly plan, it's like, okay, so what are we working on this

00:42:18.980 | week that's going to help us make progress towards this bigger goal?

00:42:21.940 | Well, let me just survey the landscape of issues and come up with one that we can make

00:42:26.540 | progress on right now.

00:42:27.660 | And then that's just all you're doing and all you care about till that's done.

00:42:31.420 | And what they do in Agile methodology is they have a place to collect ideas for this.

00:42:34.900 | So you could have this in your seasonal or quarterly plan.

00:42:38.420 | You start collecting ideas.

00:42:40.180 | Well, we need to work on loading speed and we need to fix the, here's a button, here's

00:42:44.620 | an issue.

00:42:45.620 | And you can collect those somewhere.

00:42:47.300 | That's fine.

00:42:48.300 | You can collect those somewhere, but don't think of those as tasks.

00:42:50.780 | These are just putting pins in various things that might be useful.

00:42:55.380 | And you just trust yourself on the small scale when it comes to the weekly scale that you

00:42:58.900 | can kind of survey all the different stuff that's out there that you've jotted down

00:43:02.020 | that you need to work on or is important that you'll be capable in the small scale of saying

00:43:06.780 | of all this stuff, this is a good one to do next.

00:43:09.780 | And let me just do this next.

00:43:10.780 | Because one of the things that Agile realizes, you can only do one thing at a time anyway.

00:43:15.380 | So it doesn't help to say, I'm doing these five things.

00:43:19.900 | It makes you feel better in the moment because you imagine having those five things done,

00:43:23.180 | but you can only do one thing at a time.

00:43:24.620 | So might as well do one thing at a time.

00:43:26.460 | This applies to a lot of projects.

00:43:27.860 | You can collect somewhere your notes or ideas about what needs to happen or issues that

00:43:32.260 | need to be resolved.

00:43:34.460 | When it comes to having concrete tasks that you're scheduling and they're in your list,

00:43:38.420 | it should be what you can work on next.

00:43:40.700 | All right.

00:43:42.500 | So just trying to create a huge list of concrete tasks and have them all on your list.

00:43:49.660 | I just think that creates a waterfall effect stress.

00:43:54.300 | So be okay with these larger projects.

00:43:56.940 | Be okay with only a small number of things will make it onto my to do list at a time

00:44:01.980 | from this project.

00:44:02.980 | And I trust myself each week to figure out what the best next thing is to do.

00:44:06.500 | I don't need everything to be in here.

00:44:08.580 | I don't need some more complicated long term planning as well.

00:44:11.980 | And so be a little bit more Agile.

00:44:13.380 | I think that'll work better.

00:44:15.020 | All right.

00:44:16.460 | So as our final part of our question segment here, I want to do a case study.

00:44:22.420 | This is where someone writes in explaining or talking about how they applied some ideas

00:44:26.380 | from our show in a way that is interesting or successful.

00:44:29.780 | The case study I want to report today comes from Mark.

00:44:32.660 | All right.

00:44:33.660 | So here's what Mark says.

00:44:35.660 | I'm writing a book.

00:44:37.700 | It's an academic book in my field, which is musicology.

00:44:41.140 | And I've been using Cal's approaches for a couple years now.

00:44:44.020 | I've gone from a haphazard researcher writer to a true professional using his approaches.

00:44:51.180 | I added a fun new element.

00:44:52.940 | I designed and printed custom writing t shirts for myself.

00:44:55.780 | They are just plain black t shirts, but I made a secret label on the inside.

00:44:59.160 | It says this black shirt is for creating.

00:45:02.340 | And I added a small logo on one sleeve.

00:45:06.280 | The rule I have set for myself is that when I put on one of these t shirts, I can't go

00:45:10.280 | to sleep again until I do significant writing.

00:45:13.260 | At least an hour, but usually deep work sessions of two to four hours.

00:45:16.500 | I definitely don't need these shirts to write, but just like the countless examples Cal has

00:45:20.940 | given of other creators going to great lengths to signal to themselves that it's time to

00:45:24.740 | create such as Brandon Sanderson's underground layer, which is where he wrote Name of the

00:45:30.580 | Wind by the way.

00:45:32.780 | These shirts have been a fun way to get work done and go deep.

00:45:36.820 | I've submitted a book proposal, edited two chapters, completed drafts of two more chapters,

00:45:40.900 | and I'm halfway through the third chapter now.

00:45:42.820 | I have never had more momentum.

00:45:44.900 | Well, I appreciate that case study Mark, because I think it does underscore a point we talk

00:45:49.780 | about a lot.

00:45:51.700 | Ritual and setting matters when it comes to trying to do hard things with your brain.

00:45:56.060 | This is not natural for the human brain to concentrate on symbolic or abstract notions

00:46:02.320 | for extended periods of time.

00:46:03.380 | So everything we can do to help put our brain into that setting, the better.

00:46:08.260 | So things that seem weird from the outside, a black shirt that has a hidden label that

00:46:12.140 | says the shirt is for creating, it seems weird.

00:46:14.860 | But you know what else is weird?

00:46:16.380 | Sitting down to write a textbook on musicology.

00:46:18.180 | This is not something that the Paleolithic human spent a lot of time caring about.

00:46:22.180 | We don't have an evolutionary pressure for it.

00:46:24.500 | So the more we think about deep work as a noble, but unusual and demanding activity,

00:46:29.740 | I think the more we can embrace unusual rituals and settings to help try to induce those states.

00:46:37.300 | So I love hearing these types of examples of people going increasingly over the top

00:46:41.980 | to help put themselves and their mind into a deep work mindset.

00:46:48.020 | I think the Brandon Satterson example is great.

00:46:49.820 | That's one of my favorites.

00:46:50.820 | We talked about this on the show before, but the fantasy writer Brandon Satterson in his

00:46:55.820 | suburban house, suburban Utah, in a cul-de-sac, he owned a lot next to it, underground, built

00:47:03.580 | this essentially giant bunker, multi-room bunker, completely decked out in a high-end

00:47:10.300 | sort of Victorian Gothic decor in which he writes, he has a movie theater down there,

00:47:16.820 | he podcasts down there, they have meetings down there for his companies.

00:47:20.740 | I mean, it's completely over the top and unnecessary and just fantastic.

00:47:24.380 | If that's your job is to write fantasy, why not have a fantastical place to do it?

00:47:29.020 | I mean, just to go to a grim home office and it's just generic and you're at the white

00:47:34.140 | desk and you have, you know, laundry baskets in there.

00:47:37.940 | I mean, that's just adding ankle weights to the basketball player.

00:47:42.620 | It's an unforced error.

00:47:44.380 | You're making the cognitive work you're about to do harder.

00:47:48.300 | It doesn't have to be.

00:47:50.420 | So embracing the cool and the unusual, I'm always here for that, Jesse, so I'm glad that

00:47:54.260 | people send in examples.

00:47:55.260 | So I want to get to a final segment, cool study I want to talk about.

00:48:00.300 | First let's mention another sponsor that makes this show possible.

00:48:05.700 | This episode is sponsored by BetterHelp.

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00:48:17.380 | thing.

00:48:18.380 | I mean, we were just talking about this in the last case study, how the mind is fickle

00:48:22.480 | and to do something like convince it to think deeply about a novel for a few hours is something

00:48:27.600 | that requires a lot of work.

00:48:30.620 | Well because the mind is so fickle, it can also fall into states or configurations that

00:48:34.620 | can hold us back.

00:48:36.860 | You might have, for example, constant ruminations, negative ruminations on things that have happened

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00:48:45.480 | You could have these thought patterns that really are making your life harder, making

00:48:49.300 | it harder for you to do the things that you really value, that make you feel bad more

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00:50:31.980 | Also want to talk about our friends at ExpressVPN.

00:50:34.380 | Let me put on my computer science hat for a moment.

00:50:38.980 | I wonder what a computer science hat would actually look like.

00:50:42.180 | I mean, it would probably have Vulcan ears and somehow a circuit board involved.

00:50:49.780 | I don't know.

00:50:50.780 | But just imagine I'm wearing a computer science hat because I'm about to get real computer

00:50:53.740 | sciencey with you.

00:50:54.980 | You need to be using a VPN.

00:50:57.380 | Because what happens is when you connect to the internet, people can see what sites or

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00:51:03.020 | If you're in a public wireless access point, anyone nearby can be reading your packets

00:51:07.420 | out of the airwaves and know that you are spending an inordinate amount of time on Jesse

00:51:11.420 | Skeleton.

00:51:12.420 | And if they figure that out, they're going to call the authorities as they probably should.

00:51:16.840 | Same thing even when you're at home.

00:51:19.060 | You feel like you have privacy there, but your internet service provider can see what

00:51:22.060 | sites and services are you using.

00:51:24.980 | They can collect and sell that data to advertisers and believe me, they do.

00:51:28.300 | A VPN protects you from that.

00:51:31.220 | With a VPN, instead of connecting directly to the site or service you want to use, you

00:51:35.740 | connect instead to a VPN server.

00:51:38.500 | You then tell that server with an encrypted message, "Here is who I really want to talk

00:51:42.540 | with."

00:51:43.940 | And the VPN talks to that site or service on your behalf, encrypts the response and

00:51:47.220 | sends it back.

00:51:48.420 | So now the person at the coffee shop or your internet service provider knows nothing about

00:51:52.020 | what you're doing other than you're protecting your behavior using a VPN.

00:51:56.420 | So you need a VPN.

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00:52:47.700 | All right.

00:52:48.700 | So now we've got to our final segment, a CalReact segment, find something that someone sent

00:53:03.060 | me or discovered that I think is worth discussing.

00:53:05.260 | And I want to talk about an academic paper that's making the rounds.

00:53:10.540 | Multiple people sent it to me.

00:53:12.340 | It has an interesting mathematical idea that I think helps explain a lot of things we experience

00:53:16.620 | in real life and gives us some ideas about solutions.

00:53:19.920 | So I'm going to load this on the screen.

00:53:21.420 | And again, if you're just listening to the show, you can see the show at the deeplife.com/listen

00:53:27.380 | episode 271.

00:53:28.660 | The videos are at the bottom of the episode page.

00:53:30.820 | All right.

00:53:31.820 | So what I have loaded on the page here is a, an economics paper.

00:53:36.580 | I don't know if this has been published yet or if it's about to be published, but anyways,

00:53:42.180 | the name of the paper is when product markets become collective traps, the case of social

00:53:49.740 | media.

00:53:50.740 | I'm going to read you a few sentences here from the abstract.

00:53:54.620 | They're going to sound a little bit like academic gobbledygook, but then we're going to decipher

00:53:57.660 | them and it's actually going to be somewhat profound.

00:53:59.580 | All right.

00:54:00.580 | So let me get my, my pen out here.

00:54:03.260 | All right.

00:54:04.260 | So here we go.

00:54:05.700 | In large scale incentivized experiments with college students, we show that while standard

00:54:11.940 | welfare measures, we're over here, suggest a large and positive surplus, our measure

00:54:18.180 | accounting for consumption spill overs indicates a negative surplus with a large share of active

00:54:23.980 | users deriving negative utility.

00:54:27.980 | We also shed light on the drivers of consumption spill overs to non-users in the case of social

00:54:31.900 | media and show that in this setting, the fear of missing out plays an important role.

00:54:36.060 | Our framework and estimates highlight the possibility of product market traps where

00:54:40.940 | large shares of consumers are trapped in an inefficient equilibrium and would prefer that

00:54:47.060 | the product not exist.

00:54:49.060 | I'm going to put a box here around the word inefficient equilibrium because I've been

00:54:54.180 | using this phraseology quite a bit in my recent talks on technology.

00:54:58.620 | So what does this all mean?

00:54:59.980 | Well, these are economists that we're studying in this case, social media use.

00:55:06.140 | And they were saying it's confusing.

00:55:09.540 | It's confusing sometimes when we directly study the individual user and we see how much

00:55:17.380 | they value social media, is the impact positive, is the impact negative?

00:55:22.180 | And it's confusing why we find so much usage.

00:55:26.940 | Like why are people using this?

00:55:29.780 | If for example, we can measure there's like a negative effect, it's making them less happy.

00:55:34.540 | We can see this.

00:55:36.400 | And what they're arguing here is, okay, you also have to measure if you really want to

00:55:40.340 | understand consumer behavior for a large population, you also have to measure the impact of not

00:55:47.960 | using.

00:55:50.060 | And when you integrate the impact of not using, interesting dynamics arise.

00:55:55.820 | And their model that they work out here mathematically for social media based on data from experiments

00:56:01.020 | with students and incentives and seeing how much they value social media, the model that

00:56:05.300 | they derive here says, okay, here's what seems to be happening.

00:56:08.700 | People do not like a lot about social media.

00:56:12.260 | We can measure that it directly makes their life negative in many ways.

00:56:15.340 | But there is also, especially for talking about young people, a really big cost to being

00:56:20.060 | the only person you know, not using it.

00:56:24.060 | So the non-user has a big negative cost as well.

00:56:27.620 | And is that non-user cost, which if we're going to use a rational economic model is

00:56:32.300 | outweighing the negatives of using it.

00:56:35.380 | And that's why we find people stuck on the platform.

00:56:39.660 | Now why is this called a collective trap or an inefficient equilibrium is because that

00:56:43.980 | negative cost of not using is only incurred if you're the only person to stop using it.

00:56:49.460 | So actually the better configuration in which the total amount of happiness is maximized

00:56:56.460 | is one in which most people stop using it.

00:56:59.980 | Because then you avoid the negatives you get from being on social media.

00:57:04.180 | And if most people are not using it, the negative cost of not using social media dissipates

00:57:09.340 | as well.

00:57:11.020 | They point out here in particular with the college students, they study fear of missing

00:57:14.020 | out being the main negative cost.

00:57:15.700 | If you're not missing out, not being on social media, you lose that negative cost.

00:57:20.500 | Then you might as well get rid of the negative cost of using social media.

00:57:24.580 | So why we have so many people using it at the same time that they're so unhappy about

00:57:28.400 | it is because they are in an inefficient equilibrium.

00:57:31.980 | Now this terminology comes out of the game theory work, the nonlinear dynamics of John

00:57:37.940 | Nash, Nobel laureate John Nash, subject of the Russell Crowe movie, A Beautiful Mind,

00:57:43.420 | and of course the Sylvia Nassar biography on which that movie was based.

00:57:47.780 | This was the key contribution.

00:57:49.060 | This is what won John Nash the Nobel Prize in economics is that he figured out in game

00:57:54.220 | theory what happens is you get stuck in these equilibriums, meaning there's no change any

00:58:01.540 | individual can make to their strategy to make themselves better off.

00:58:05.960 | But the equilibrium is not the best possibility for everyone.

00:58:10.700 | In other words, no one person can make their situation better, but if we all change together,

00:58:15.860 | we could be in a better configuration.

00:58:17.300 | We're stuck.

00:58:18.300 | We call it an inefficient equilibrium because we're far from the maximum positive value

00:58:22.420 | that we could be creating, but we can't get to the maximum possible value because no one

00:58:27.820 | person can make the change on their own.

00:58:29.760 | If one person leaves, things get worse.

00:58:32.120 | This is what social media is in this model.

00:58:34.500 | It's an inefficient equilibrium.

00:58:36.580 | People are not happy that they're on TikTok all the time or Instagram all the time, but

00:58:40.220 | no one individual can make their situation better by leaving the service because then

00:58:43.660 | they're missing out because everyone else is on it.

00:58:45.420 | So we're stuck just being mildly unhappy because we want to avoid the even bigger unhappiness

00:58:49.720 | of being the odd person out.

00:58:52.920 | But this configuration doesn't maximize our possible happiness.

00:58:55.460 | We'd all be much happier if we just didn't use it at all.

00:58:59.480 | Our total happiness would be much higher, but no one person can get there.

00:59:02.860 | It's inefficient equilibrium.

00:59:05.780 | Collective trap is another way of describing this.

00:59:07.660 | We're trapped using something we don't like because there's no easy way for us to unilaterally

00:59:11.540 | escape it without making things worse.

00:59:13.900 | Now, where I think this is particularly relevant in social media, like what is the particularly

00:59:18.940 | relevant corollary to this result, is that it really should change the way we think about

00:59:24.860 | social media and youth.

00:59:28.080 | We know I've given talks on this.

00:59:29.620 | I'm deep into this research literature we've talked about on the show.

00:59:32.020 | I have a YouTube video about this.

00:59:34.380 | We know there is now a strong signal.

00:59:37.220 | There's less debate about this now than there was three years ago.

00:59:39.660 | A strong signal that shows increasing social media use leads to increasing mental health

00:59:44.700 | negative outcomes for adolescents, especially prepubescent girls.

00:59:49.260 | We know there's this negative impact between social media and youth.

00:59:53.220 | And we know that the self-reports from youth say, "This is making me anxious.

00:59:57.980 | This is what's making us anxious.

00:59:59.340 | It is social media.

01:00:00.340 | I don't like social media."

01:00:02.780 | Studies like this help us understand why they get stuck because it is an inefficient equilibrium.

01:00:07.540 | It is very difficult for a teenager to be the only teenager in their class who's not

01:00:11.680 | using social media.

01:00:12.680 | That's even worse.

01:00:13.680 | They have to use it and incur these negativities.

01:00:16.180 | So if we want to break these collective traps, this is where we can come in and say, "Well,

01:00:20.660 | how do we get more than one person not using this?

01:00:24.300 | How do we come in and get most people not using it or large swaths of people not using

01:00:27.660 | it?

01:00:28.660 | How do we get rid of the negative cost of choosing to say no?"

01:00:33.120 | That's where we should put a lot of energy.

01:00:34.840 | And this is where schools, for example, being very aggressive about, "We really don't allow

01:00:38.460 | phones and we really do not think that kids should have access to social media until they

01:00:42.260 | get to this age."

01:00:43.260 | And this is where we should be really clear about it matters.

01:00:44.980 | They're not going to change every mind, but if you change 20% of the mind, you can reduce

01:00:49.460 | the negative cost of not using and therefore free people from the collective trap.

01:00:55.080 | This is where I think cultural suggestions like the current surge in general saying,

01:00:58.860 | "You should be 16 before you have unrestricted access to the internet and in particular social

01:01:03.940 | media."

01:01:04.940 | This is where this is really important because individual students otherwise get stuck into

01:01:09.380 | this collective trap where everyone is unhappy and they can't get out of it.

01:01:12.380 | So one way to break the trap is to say, "Okay, let's spring it.

01:01:15.780 | No one can use this until they're older."

01:01:19.080 | And we've massively increased the positive utility of everyone's experience.

01:01:25.900 | There's other places where we see these collective traps or inefficient equilibriums at play

01:01:29.980 | in tech and society.

01:01:31.940 | The place that I have highlighted often in my work is email in the workplace.

01:01:36.500 | For various reasons, we stumbled into this collaboration style that in my book, "A World

01:01:40.820 | Without Email," I call the hyperactive high find where everything is worked out with ad

01:01:45.620 | hoc back and forth messaging.

01:01:47.760 | This causes huge amounts of problems that I detail often on the show and in my book.

01:01:53.620 | Why does this persist however if it makes people so miserable?

01:01:57.620 | Well, it is an inefficient equilibrium.

01:01:59.780 | It's a collective trap.

01:02:01.100 | If this is how everyone is organizing their work at my office, which is back and forth

01:02:05.140 | ad hoc emails, me leaving this unilaterally is going to make things even worse for me

01:02:10.780 | because now I'm slowing up decisions.

01:02:13.180 | People are mad at me.

01:02:14.180 | My job might be in jeopardy.

01:02:15.580 | So the cost of me leaving the hyperactive hive mind by myself is even worse.

01:02:19.460 | So I just stick there.

01:02:21.420 | The only way to spring the trap in this context is to have the organization itself come in

01:02:26.420 | and say, "Enough.

01:02:27.740 | We don't collaborate with back and forth email.

01:02:30.740 | Email is for delivering documents.

01:02:32.600 | Email is for questions that can be answered with one message.

01:02:35.580 | Everything else, here's how we do it."

01:02:38.260 | You have to get everyone out of the trap together or we all stay mired in it forever.

01:02:44.420 | And so I think collective traps are an important way of understanding techno-social behaviors,

01:02:49.540 | especially with a techno-social behavior where we all kind of agree this is bad and it's

01:02:53.260 | making us unhappy.

01:02:54.780 | But no one seems to be able to easily leave it.

01:02:56.820 | This often is the explanation going on.

01:02:59.300 | So this particular paper, again, "When Products Markets Become Collective Traps, the Case

01:03:02.600 | for Social Media," interesting paper.

01:03:05.300 | I think they're touching on something that is true.

01:03:07.840 | For years now, I've been trying to teach audiences about inefficient Nash Equilibriums

01:03:12.020 | as an explanation for some of these collective behaviors we see.

01:03:14.780 | So I'm glad there's actually some mathematics now.

01:03:16.660 | There's some experimental economics as well that says maybe I was onto something.

01:03:20.340 | All right.

01:03:21.340 | So that's all the time we have for today.

01:03:24.700 | Thank you for listening or watching.

01:03:28.180 | Remember, leave a positive review if you like it because we know that helps other people

01:03:32.420 | discover it.

01:03:33.420 | We'll be back next week for our Halloween episode of the show.

01:03:37.740 | And until then, as always, stay deep.

01:03:40.540 | Hey, so if you liked today's episode about playing the long game, I think you might also

01:03:46.580 | like episode 254, which is called "The Laws of Less," where we get into how some of the

01:03:53.780 | most interesting, impactful, and happy people in the world systematically try to reduce

01:03:59.660 | the number of things they're working on.

01:04:01.340 | I think you'll like it.

01:04:02.740 | Check it out.

01:04:03.740 | So let's make that today's deep question.

01:04:06.460 | Why should I do less?

Living A Life Without Regret: 3 Big Things You Need To Know Before 30 | Cal Newport

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