Where Should I Start With Long-Term Planning?
Chapters
0:0 Cal's Intro0:14 Cal reads a question about long-term planning
1:45 Cal explains a Value Plan
2:40 Aiming yourself to positive options
00:00:00.000 | [MUSIC PLAYING]
00:00:03.360 | All right, let's move on to a question from Philip.
00:00:09.880 | Philip asks, where should I start with long-term planning?
00:00:16.960 | He elaborates, I admire your work a lot.
00:00:20.040 | Your advice has been useful.
00:00:22.520 | And on the short to medium term, he thinks he's doing well.
00:00:25.480 | But when it comes to longer-term planning on the scale of years,
00:00:29.160 | it is, quote, "quite daunting to me,
00:00:32.000 | and I have no idea where to begin," end quote.
00:00:37.000 | So Philip, I don't know that I would
00:00:39.240 | recommend that you have detailed plans on the scale of years.
00:00:44.960 | The short to medium term you talk about,
00:00:47.120 | I think, is the sweet spot, where you have
00:00:49.880 | some vision to the future.
00:00:51.000 | You're out of the short-term context of just reactivity,
00:00:55.000 | but it's still tractable.
00:00:58.040 | So as you know, I have semester plans,
00:01:00.600 | so plans on the scale of a current season,
00:01:03.800 | three of those a year.
00:01:05.360 | And I typically have-- I've talked about this on the show--
00:01:07.860 | I typically have some sort of birthday project.
00:01:10.760 | So that's an annual plan.
00:01:13.000 | By the time I get to my next birthday,
00:01:15.520 | these are some bigger picture changes
00:01:18.000 | I want to have happen in my life.
00:01:19.680 | So right now, I'm 39.
00:01:20.800 | Project 40 is ongoing.
00:01:22.520 | It's a collection of major changes
00:01:24.040 | I want to work on by the time I turn 40.
00:01:26.640 | So I have a semester plan, and I have an annual plan.
00:01:29.200 | I don't really go much farther beyond that.
00:01:32.960 | I don't go much farther beyond that.
00:01:34.680 | So how do you think about the big picture future?
00:01:38.120 | Well, one, this is where having your values nailed down
00:01:42.240 | in those semester plan documents is really important.
00:01:46.160 | There, you're laying out the properties of your vision
00:01:50.760 | of a life well-lived.
00:01:53.040 | But it's not specific.
00:01:54.200 | It's not, and I'll be in this job,
00:01:55.620 | and this place, and I'll have this much money,
00:01:57.960 | and be able to run a mile at this time.
00:02:00.280 | It's not that specific.
00:02:01.280 | It's talking about, these are the values I want,
00:02:03.400 | the properties I want in my life.
00:02:05.160 | And you look at those when you think about your annual birthday
00:02:07.860 | goals, and you look at those when you build your semester
00:02:09.960 | plan to make sure you're making progress towards a life that's
00:02:12.120 | more like that.
00:02:13.080 | But it's vague and more general than these
00:02:14.960 | are very specific things I want to do.
00:02:17.320 | The other thing I typically recommend to people,
00:02:19.480 | especially early on, is you want to aim yourself
00:02:24.240 | not towards an incredibly specific outcome,
00:02:26.960 | but towards a direction that's going
00:02:28.760 | to have a lot of options that are
00:02:30.160 | going to be useful to the type of things you value.
00:02:34.400 | When I was coming out of college, for example,
00:02:37.760 | and trying to figure out what I wanted to do,
00:02:40.040 | I aimed myself towards graduate school and potential
00:02:44.040 | professoredom because I thought, at least
00:02:47.160 | in the short term of multiple years,
00:02:49.520 | this is going to give me a lot more flexibility.
00:02:51.920 | I can keep writing books.
00:02:53.520 | I'm going to have much more time affluence.
00:02:56.240 | I was looking at other options, including going to Microsoft.
00:02:58.880 | I had an offer from Microsoft.
00:03:00.200 | This seemed like it would be much more structured,
00:03:03.960 | and have much less time.
00:03:04.960 | It'd be much more hard charging.
00:03:05.960 | I had these other interests I was trying to figure out,
00:03:07.840 | but I didn't know exactly where they were going to go.
00:03:09.520 | I just thought the options of that direction would be better.
00:03:12.020 | I like intellectual work.
00:03:13.320 | I seem to be doing well intellectually
00:03:15.360 | with computer science.
00:03:16.040 | Let's take that for a spin.
00:03:16.920 | I like this writing thing.
00:03:17.960 | I want to take that for a spin.
00:03:18.960 | I want some autonomy there.
00:03:20.080 | Let's go down the grad school path.
00:03:22.600 | It's the right direction towards more options.
00:03:26.000 | And then over time, it gets refined.
00:03:28.040 | And OK, I'm definitely going to do this with my writing.
00:03:30.000 | I'm definitely going to do a professoredom.
00:03:31.160 | Here's the type of professoredom I'm going to do.
00:03:33.320 | The details of my life today were not on the docket
00:03:36.120 | when I was 22 years old.
00:03:37.760 | But I pointed myself in a direction
00:03:39.260 | that situations like my current situation would be possible.
00:03:43.040 | So that's what I would say.
00:03:44.120 | You don't need detailed plans beyond a semester,
00:03:47.400 | plus maybe some goals for your life
00:03:49.560 | for each year at your birthday.
00:03:50.800 | Beyond that, just aim yourself towards directions
00:03:55.240 | that will be congruent with your values
00:03:57.120 | and figure things out as it unfolds.
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