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Where Should I Start With Long-Term Planning?


Chapters

0:0 Cal's Intro
0:14 Cal reads a question about long-term planning
1:45 Cal explains a Value Plan
2:40 Aiming yourself to positive options

Transcript

All right, let's move on to a question from Philip. Philip asks, where should I start with long-term planning? He elaborates, I admire your work a lot. Your advice has been useful. And on the short to medium term, he thinks he's doing well. But when it comes to longer-term planning on the scale of years, it is, quote, "quite daunting to me, and I have no idea where to begin," end quote.

So Philip, I don't know that I would recommend that you have detailed plans on the scale of years. The short to medium term you talk about, I think, is the sweet spot, where you have some vision to the future. You're out of the short-term context of just reactivity, but it's still tractable.

So as you know, I have semester plans, so plans on the scale of a current season, three of those a year. And I typically have-- I've talked about this on the show-- I typically have some sort of birthday project. So that's an annual plan. By the time I get to my next birthday, these are some bigger picture changes I want to have happen in my life.

So right now, I'm 39. Project 40 is ongoing. It's a collection of major changes I want to work on by the time I turn 40. So I have a semester plan, and I have an annual plan. I don't really go much farther beyond that. I don't go much farther beyond that.

So how do you think about the big picture future? Well, one, this is where having your values nailed down in those semester plan documents is really important. There, you're laying out the properties of your vision of a life well-lived. But it's not specific. It's not, and I'll be in this job, and this place, and I'll have this much money, and be able to run a mile at this time.

It's not that specific. It's talking about, these are the values I want, the properties I want in my life. And you look at those when you think about your annual birthday goals, and you look at those when you build your semester plan to make sure you're making progress towards a life that's more like that.

But it's vague and more general than these are very specific things I want to do. The other thing I typically recommend to people, especially early on, is you want to aim yourself not towards an incredibly specific outcome, but towards a direction that's going to have a lot of options that are going to be useful to the type of things you value.

When I was coming out of college, for example, and trying to figure out what I wanted to do, I aimed myself towards graduate school and potential professoredom because I thought, at least in the short term of multiple years, this is going to give me a lot more flexibility. I can keep writing books.

I'm going to have much more time affluence. I was looking at other options, including going to Microsoft. I had an offer from Microsoft. This seemed like it would be much more structured, and have much less time. It'd be much more hard charging. I had these other interests I was trying to figure out, but I didn't know exactly where they were going to go.

I just thought the options of that direction would be better. I like intellectual work. I seem to be doing well intellectually with computer science. Let's take that for a spin. I like this writing thing. I want to take that for a spin. I want some autonomy there. Let's go down the grad school path.

It's the right direction towards more options. And then over time, it gets refined. And OK, I'm definitely going to do this with my writing. I'm definitely going to do a professoredom. Here's the type of professoredom I'm going to do. The details of my life today were not on the docket when I was 22 years old.

But I pointed myself in a direction that situations like my current situation would be possible. So that's what I would say. You don't need detailed plans beyond a semester, plus maybe some goals for your life for each year at your birthday. Beyond that, just aim yourself towards directions that will be congruent with your values and figure things out as it unfolds.

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