With that, let's get into it. Jesse, what is our first query of this week's episode? - Okay, first question's from Rex. He's a director of career office at a New England university. I'm the director of a career office for an engineering students at an R1 university. Any suggestions on who we might structure a course about lifestyle-centric career planning for our students?

- Well, a well-timed question, because our deep dive was all about values-based lifestyle-centric career planning emerging as potentially a dominant paradigm for how we think about meaning and work. So Rex, the short answer is, yes, I have good tips for designing a course on this. Jesse and I's consulting fee is $250,000, but we will be happy to spend, that gets you 45 minutes of our time.

Now, we do this in a group call, so we might be consulting for a few people at the same time, but we'll give you some advice, Jesse and I, so it's $250,000, and there we go. All right, next question. - A TDL Roan shirt. - And a, yes, and a Roan shirt.

We need $250,000 and a Roan shirt. No, okay, I have some thoughts here. Thoughts is the right word. I was jotting down some notes before the episode about what I might put into a lesson plan for lifestyle-centric career planning. So I'm calling this thoughts, 'cause this is not worked through.

I just thought it would be fun to be concrete for the sake of being concrete. So let's just experiment here. Okay, so what might I do if I was teaching a bunch of college kids how to think about their career? I would start by saying, let's form a vision.

This is classic lifestyle-centric career planning. Let's form a vision of your life, maybe at the age of 25, and again, at the age of 35. We want a fully featured vision about all aspects of your life, not just your job, but all aspects of your life, five years from now, and maybe 10 or 15 years from now.

To help structure this vision, you might wanna use something like the deep life buckets, where we have craft, community, contemplation, constitution, maybe sometimes, what am I missing here? Sometimes we do celebration. You know, we talk about this a lot on the show, but you might wanna use something like that, the structure.

Well, what are all the different aspects of my life that I wanna be included in this vision? It's okay if this vision evolves. It's not set in stone, just what's resonating with you right now when you imagine what your life would be like. All right, now we need to get from this vision.

Here's where we get to my new arbitrary lesson plan. We have to get from this vision to you choosing a job. Maybe you're a senior, you have to start job hunting. How do you choose a job? Maybe you're farther along in your career, but wanna make a change. How do you choose a job?

How do we get brass tacks from something so broad? Well, I'm gonna give you three, what should I call these? Three properties, three properties of a job. Income, how much income it generates, location. So you're thinking about where you're living, and work type, which can include both the content, like the specifics of what you're doing, but also the parameter under which you're doing this work.

So flexibility, number of hours you're actually working. So for each of these three properties, income, location, and work type, you wanna answer what would I need for each of these three properties in my job to support this big vision I had? So I have this big vision, how much money am I gonna need?

Where do I need to live? What type and how much work would I be doing? So you answer those three questions. Now you have the specificity you need to go search for a job, because now you're thinking about, okay, now I need to find a job that is going to get me those three properties, or perhaps more realistically, if you're just coming out of school, will get me to those three properties if over the first five years or 10 years, I get after it, become so good, I can't be ignored, build up career capital.

The answer to those three questions I'm gonna propose is the bridge from a broad vision to a specific choice of job. So let me give an example. I was working on my slow productivity book this morning, as I do every morning, six days a week, I work on my book.

But today I was working on a chapter and I was talking about in that chapter, the entrepreneur Paul Jarvis. So I went on a Paul Jarvis deep dive, a sort of rabbit hole this morning, so he's fresh on my mind. So if you don't know Paul Jarvis, he wrote a book in 2019 that I blurbed that was called "Company of One", which I really enjoyed.

It was about how if you're an entrepreneur or freelancer and you start to get good, don't scale your business, instead leverage that increased ability to gain more flexibility and freedom in your business. So if you're making $50 an hour as the web designer, and you start to get really good, and there's a lot of demand for your work, don't scale up a web design business where you hire four more designers to try to get your income to really go up even farther.

Instead, double your rate and work half the hours. That's the idea of "Company of One". Keep it small, invest your skill to get more flexibility. Anyways, because I happen to know a lot about this guy today, let's answer those three questions. The income I need, the location I want to be, and the work type I need.

Let's answer those questions for him and then talk about how he found a job that accomplished him. So based on the various interviews I read, he had a vision of his life that was going to be, he wanted to get out of the rat race, to get out of the city, to get away from stress, deadlines, stressed out clients.

He was tired of all of that. Him and his wife wanted to be somewhere quiet. They wanted to spend a lot of time outdoors. This was the vision they had built. And he wanted a lot of autonomy in his time. His wife was really into surfing, so she wanted to be able to just go surf.

He wanted to be able to go for long walks and tend a garden. And so they had this vision. So it's a vision of life where work wasn't at the center of it. At the same time, he's a creative. So he was a web designer and he liked creative work.

He's a creative guy. You know, he has tattoos on his arm, so that means you're creative, right? So he wanted some sort of creative, interesting work going on in his life, but he also wanted quiet, away from the rat race, away from deadlines, stressful client communication, having lots of time and autonomy.

So they built this vision, they could see it. So how might he have answered those three questions? Well, for income, it didn't need to be anything special. Average middle-class salary would be enough 'cause they don't need to live somewhere expensive for them to live this vision. Because again, it's built on free time and nature, not on trips to Europe or living on the ocean.

Location, they wanted somewhere quiet. They wanted nature, but they realized it couldn't be the extreme boondocks, because again, he has tattoos on his arm. So he needs to be near a coffee shop and so they can get organic groceries, like have internet, like be near civilization, but a quiet place and in nature.

So they had to answer that question. And in terms of work type, well, he wanted the work to be creative, but to be free of, and he's very specific about this in the interviews I found, deadlines and demanding clients. So he answered those three things and said, "Great, now how do I leave what I'm doing now "as a freelancer living in what he called "a glass cube in the sky in the downtown core of Vancouver "and find a job that'll support these three visions?" What they ended up doing is they moved to, here's how they answered, found a specific job.

They moved to Tolfino. So the Pacific coast of the large rural Vancouver Island, this big island off the West Coast of British Columbia. Tolfino's about halfway up the island on the Pacific coast, has really good surf breaks. Best surfing in Canada. That's a phrase that shouldn't impress you that much.

The best surfing in Canada is maybe not that good, but there's a good surf break here. So his wife likes to surf, but it's also so far off the beaten path, as he explained, you could buy some land without having to spend that much money. So they bought some land in the woods outside of this town.

As he said, it's cheap enough that I could afford it without having a lot of money, but close enough to civilization that I could still have organic groceries delivered once a week. So they sort of found that sweet spot. So they moved there. He continued to do freelance web design for a while, but he just reduced his number of clients at first.

All right, so that was step one. That's creative work. It still had deadlines. It still had client demands, but he could do it from Tolfino. He could do it in the woods. His wife became a surf instructor at the surf school there. He built a greenhouse, began this long running war with the local raccoons who kept trying to destroy his garden.

So he sort of had that going on. And so that was the first step. And then for the second step, once they were established, they're living cheaply. They didn't really need to make that much money. He eventually switched from web design contracts to he began doing some online courses for very niche audiences.

Very niche online courses, did some podcasts, and then also more recently has done various, like again, very bespoke software products that is relevant to like a small group of people and that he could just put together and sell. That freedom from deadlines, that freedom from having to answer the clients.

And it just needs to make enough money to keep this lifestyle going. And so there they go. That vision led to those three answers, those three properties, which led to this particular choice of career, which is let me continue the freelance, but with a reduced client roster en route to doing online creative projects that I can support myself and I have to deal with clients.

And so during those first few years of doing more client work in Tolfino, he built up a mailing list, he wrote this book. So he had sort of enough of an audience that he could then sell a course. But the point is, it's a very specific thing he ended up doing.

And you don't get to that decision by saying, what's my passion, by saying, what do I wanna do with my degree? You get there by starting with a vision, making it more concrete with answers to those three questions, income, location, and work type. And then saying, given what I know how to do, my opportunities, my skills, whatever's on the table right now, what do I have available to get towards those three answers?

So I'll use that as a case study. There is my lesson plan. Rex, you can send the check for $250,000 and our Roan shirts right to the HQ. - So a course could just be like a lot of analysis of case studies and they could develop one for themselves.

- Yeah, like the court, he was doing, like he did a course on- - I'm talking about for the students. - Oh, for the students, yeah. Yeah, you could do this, right? I mean, you could just walk through. - A bunch and then- - Do the vision. - Develop your own.

- Yeah. I mean, you could have like a vault of like, here's 20 examples. So you can prime the pump. And then yeah, you do the vision, answer those questions, start working through particular jobs. Yeah, you could see this thing. You could structure this course. They should do this.

You know, the two things I'm so surprised about they don't do at colleges is one is, don't just give every student who comes in like a copy of "How to Become a Straight A Student." So first of all, your job is to be a student. I'm just gonna guess you're terrible at studying.

It's not that hard to become good at studying. Like you should think about how to become good at studying. We just give everyone that book. And then the second thing is giving people some sort of framework for thinking through what I wanna do with my life. And so then people, I don't know, people don't know.

I mean, this was my, I think I get too reflective here. I remember being really surprised about this at Dartmouth, where I went to Dartmouth. And I had come to Dartmouth sort of haphazardly, just out of public school in New Jersey, like the schools in the mountains. I don't know, it sounds cool.

You know, I didn't know a lot about Ivy League schools and whatever. And so I just sort of assumed all of these people I know at Dartmouth are gonna like go off and become professors and writers and journalists and start cool companies and just like do really interesting stuff.

Because like these are all really interesting people it's hard to get in these schools. I just remember being so surprised by how many of my friends, I really think it was 50%. I don't have the exact numbers, but I really think 50% plus of my friends at Dartmouth went to Harvard Law School.

- Yeah. - And what I didn't realize was they came from, their parents had professional jobs. The point of going to a school like this from their perspective is that it gets you in to the track to have these well-paying professional jobs. And it was just like the Manchurian candidate switch.

At some point I was like, okay, we have to start our LSAT studying group. I just remember being so surprised by that. But the schools don't give you any structure for this. You know, at least Georgetown's good about it, it has that Jesuit background. There's a sense of improving the world.

Like that, there's a thread of that because it's a Jesuit university, but most schools don't have that. And I think in the absence of any sort of systematic structure for thinking through your life, your work, your application, your skills, if you have a bunch of smart kids, they're gonna go to Wall Street consulting or law firms because it's elite, it's hard to do, and all things being equal, they wanna do things that are competitive because otherwise they feel like.

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