19 min read

Yesterday I wrote that I believe it’s never too late to make a change in your life that you’re stoked to make.

It’s important to note that I also don’t totally buy into the advice to “just follow your passion and it will all work out.”

What gives?

The best argument I’ve heard around this debate comes from Cal Newport, the author of Deep Work: Rules for Focused Success in a Distracted World, on the TropicalMBA podcast. I’ve added this part of the interview in it’s entirety below (it’s long).

You can listen to the whole episode (this section starts at 23:22) on TropicalMBA here. Listen here.

There is also a great 24-minute episode of The First 4 Years podcast called “The Skydive vs. the Ladder” that covers the same topic. Listen here.



Dan: Let’s talk about a different sort of inversion that you’ve made. But a similar kind of reversal of a way to think which is: thoughts on crafting a career. Specifically, a lot of people who listen to this are thinking about becoming successful entrepreneurs. I think … Well; I’ll just quote you. “Growing up, we’re told by our guidance counselor’s, career advice books, the news media and other to ‘follow our passion’. This advice assumes that we have a preexisting passion. If we all just have the courage to discover this calling and to match it to our livelihood, the thinking goes we’ll end up happy.” So, what’s wrong with this idea? In your view?

Cal:   Well, there are two issues with it. One is this issue that you should follow your passion depends, before it can make any sense, on the assumption that most people have preexisting passions that they can identify and use as the foundation for making career choices in our current 21st century economy.

We don’t have a lot of evidence if that’s true for most people. We don’t have a lot of evidence, especially young people coming out of college, for some reason they’re going to be pre-wired to have this strong inclination for some particular job opportunity that happens to be available in the current shape of our economy. I don’t think anywhere in our genetic history that people evolve a gene, for example, that made them really predestined to be an online marketer versus a PR person versus a computer programmer.

It really depends on this assumption that we have these passions. Most people don’t. When I was researching the book I wrote on this, what I found was this was causing a lot of anxiety and confusion for people. Like: “I’m suppose to follow my passion. Why don’t I have a passion”? What’s wrong with me? And then we start to force things into it. This must be my passion.

Dan: Well, if you had a nickel for anytime you heard someone say, “I don’t what I want to do.”

Cal:   Yeah.

Dan: For example.

Cal:   The normal response to that had been, “Well, you need to do more introspection.” But actually, I think the more sane response is, Why do we believe that people should have a preexisting inclination for what they want to do when most people, especially young people, have had almost no exposure to any of the possible jobs in the economy? They have no real sense of what they mean. They have no information or very limited information about what’s out there, what’s possible. It seems to me, really, limiting to try to figure out in advance, this is what I’m suppose to do. So that’s one problem.

The second is it depends on this assumption that: if you really like something and then you do that for your work, it’ll transfer over and you’ll really like your work. It’s one of these deductions that kind of makes sense when you hear it. But we don’t have a lot of evidence that that’s true either.

Professional satisfaction is a pretty complicated thing. There’s a lot of research on it. What you don’t find in that research is any sort of emphasis on a match of the work to a preexisting interest as being a really important factor in whether or not you find a work interesting. Of course, there are tons of stories. Tons of stories of people who love something as a hobby, switch over to do it as their work and they’re miserable: the amateur baker who opens the bakery and is, “This is terrible. I hate it.”

That’s because what makes you love your work is very different than what makes you love the topic from a personal or hobby you point of view. To tell someone, “Follow your passion”, really depends on these two things. You know what your passion is and if you match something you really like to your work, you’ll really like your work. Neither of those things tends to be true. I think we need a more sophisticated discussion about: how do real people, who really do love their work, how did they get there?

We should work backwards from reality as opposed to working forward from a slogan that just kind of makes sense when we first hear it.

Dan: Well you stumble upon something that’s resonate with me and it sounds like one of the implications of, if we’re not going to go with passion, you suggest this route, you call the “craftsperson” approach. It seems like Deep Work follows pretty closely behind that idea. If you’re going to accept this craftsperson approach. Can you describe what you mean by that?

Cal:   Yeah, I can. To be clear, passion, I don’t like the word passion but, basically, love for your work is the goal I’m espousing. What I’m doing is, I’m just inverting the order. The evidence I saw when I looked at the literature and did a lot of interviews with a variety of people who loved their work, is the evidence I saw said, most people get it backwards.

People don’t start with a strong pre-existing love for a field and then match that to their job and then love their job. It tends to be that the love for people’s work comes later. It’s something they cultivate and build towards. It’s not the starting point. It’s the end point. It’s – I want to build a career that I will end up loving. Not – I want to find a career that I’ll love from day one.

I like to clarify; I want people to love their work. Because of that, I want to make sure that they have the most actual effective advice, the most tested advice for doing it. Because if you give them bad advice, you’re holding people back from reaching that goal.

That’s where the craftsman mindset came in. If you study people who love their work, a very common path that got them there is they started by getting very good at something that’s rare and valuable. Like a craftsman honing a skill. And then they turn around and used that value as leverage. It’s once they had that leverage, they can really start shaping and crafting their career in ways that resonate and away from ways that don’t. This was a very common pattern. People got really good and then once they were good; they had this standing to craft a career that was very good to them.

It’s the things that make great work great, are really valuable and everyone wants them. No one’s just going to give them to you because it sounds nice. You have to have something to offer in return. And in the market economy what you have to have to offer in return is some really bankable skills.

This “craftsman mindset” is don’t focus on what’s my job bringing to me. It’s what am I bringing to the job? You build your skill like the craftsman. It’s not about loving your work everyday. It’s about building towards a point in your work, five years from now, that you’re going to love it.

It turns out there’s deep satisfaction in skill honing. Humans really like this. You’re getting better at something. You’re crafting a craft that’s useful to the world and that people value. As you get better at it, your passion for your work grows. Your motivation for your work grows. Then you get to start shaping your career towards the cool things that we all like. That’s the craftsman mindset.


I wrote a book that talked about this. A lot of people came back and said, “Okay, I buy it. How do I do it?” You can think of ‘Deep Work’ as the answer to that question.

Dan: One of the conclusions you come to is kind of quietly startling, especially, for a lot of entrepreneurs who might be dreaming of or thinking of, how they get started, where do I go, which direction, what kind of business. That conclusion is professional success is hard but it’s not complicated.

Cal:   Yeah. It’s not that complicated. What goes along with that is the choice of what you do is not nearly as important as you think. Now, the flip side of that is: what you do after you make the choice is much more important than people believe. In my worldview, in terms of choosing what you do, it’s not that you can just throw a dart at a job listing and say, “Good. I guess I’m going to be a pharmacist.” That would be naive.

On the other hand, I think if something seems interesting to you, if something got really good at it – that’s enough for that to become a potential foundation for a work in life you really love. If you have, in your life, a dozen different things that match that criteria, any of them can be the foundation of a working life you love.

Dan: You offer a lot of interesting caveats along the way, through your books. One of them is that, control requires capital. To illuminate that, you use an example pretty close to this community. Which is a lot of our listeners consider themselves, “lifestyle designers”. They want to take control of their life. Do you recall the example you used of the lifestyle designer who didn’t quite have enough capital to take control?

This is Jane’s story of the blogger.

“If you spend some time browsing the blogs of lesser known lifestyle designers”, so lesser known than Tim Ferriss, I fell into that category-

Cal:   No. You’re not a lesser known! (laughs)

Dan: You’ll begin to notice the same red flags again and again. Of course, we’re not just singling out this community but I think it’s an interesting point. “A distressingly large faction of these contrarians like Jane, skipped over the part where they build a stable means to support their unconventional lifestyle. They assume that generating the courage to pursue control is what matters while everything else is just a detail that is easily worked out”.

Can you describe this problem? ‘Cause I think we all can … We’ve all seen this.

What strategically is going wrong here?

Cal:   The metaphor I used to try to understand career development and passion is this metaphor of career capital. The way I like to think about it is as you get better at things that are rare and valuable, you can imagine that you get more of this career capital deposited in your account. The more skill you have and the more various, the more valuable, the more career capital you have.

Then, you turn around and think that this career capital is what, in turn; you invest to get cool things in your working life.

If you study people who love what they do, something that comes up often, and I think I called it “the good life elixir” … Something that comes up often is they have a lot autonomy. This is in part why I think lifestyle design and Tim’s work really resonated when it first came out, because he was hitting on something that we seem to be hard wired for. Which is we love the idea and we thrive in autonomy. By which, I mean, you have control over what you do and how you do it in your working life. Which I think is a lot of what’s at the core of lifestyle design.

He’s right. That is a fantastic thing to go after. I loved, in his original book, his use of this currency … I mean this kind of influences my work with career capital. This currency notion that you have monetary currency but also, the currency you have in terms of, time and freedom is just as valuable. That’s 100% true. My research bore that out completely.

The issue is, in my formulation, if you want, let’s say, like a lot of autonomy, which can be very valuable, you have to pay career capital for it.

If you want a ton of autonomy, and a really interesting life, then you probably need a ton of career capital, roughly speaking, to invest in it. The career capital’s built up by building up rare and valuable skills.

You probably would know this better than me, since you’ve monitored and known this community for a long time now, there was this first wave of people who came after, say ‘Four Hour Workweek’, who loved the autonomy idea but didn’t have the career capital to invest to get it. So, it’s like, “Great. I’ve quit my job. I’m going to Thailand”. They left out the part of, what do I have to offer to the market in return that’s going to allow me to have a lifestyle where I can be fine financially and still have huge flexibility on my hours and live where I want to live. Geoarbitrage was not going to cover that whole gap. There had to be something to fill in.

That’s why I told that story, of a blogger who, lifestyle designer, who just quit the job. Started the blog. Was then wondering: why am I not making a living off of this. There’s actually no capital. No capital, no value to offer to get that in exchange.

Then, I told the alternative story of a developer, Lulu, who built up a rare and valuable skill in a particular type of database development. Then, leveraged that … I told her whole career story – at every step she leveraged her skill. She got better to get more flexibility and more freedom. She ended up in a place where she could then do six months on six months off. She actually would go to Thailand in her six months off. That’s why I used that because her family was from there. She learned such a rare and valuable skill that she could work for six months. She was in a lot of demand, would make a lot of money. Then, take six months off – scuba license or pilot license … I mean, that’s all autonomy dreams of lifestyle design.

My argument is that’s right way to do it. The workplace, the work environment is a market economy. The cooler the thing you want in your life, the more you have to offer in return. It’s like before you get to the four-hour workweek, there’s the 40-hour workweek of building your skill. Then you cash it in to get the four-hour workweek. That was the formulation that seemed to make more sense when I was out there studying the problem.

Dan: A few ways you suggest doing that are by placing these little bets in your career. One of the other things that I’m hoping you can describe for us is this idea of pushing yourself to the edge of possibilities.

Cal:   There are really two things at play here. The first thing at play is this notion that – if you want an awesome career, choose a skill and relentlessly develop it like you’re an athlete in intense focus training. Most people don’t do that. This is, I think, this is the key to succeeding with lifestyle design, is you have something that’s valuable that you’re relentlessly getting better at. Not just doing it a lot, but training like you’re LeBron James. Where’s my weakness? I need a little bit better free throw percentage from this part of the paint. I’m going to go do a thousand of those with an obstacle in the way. You do the equivalent in this skill. I’m trying to get better at this type of programming. I’m really weak on tree algorithms. I’m going to be the boss of tree algorithms by time this week is over. That type of thing.

The second thing I noticed … This also comes up … The book, by the way, just to set the context we’re talking about here, is something I wrote back in 2012 called, “So Good They Can’t Ignore You”. Just so we can connect it back to it. Something else I noticed in that book, when I studied people who love what they did is that a lot of them, not all of them, but a lot of them, had some sort of mission that they organized their working life around. It gave meaning and direction to everything they were trying to do.

In some sense this is on a spectrum. If you study people who love what they do on end you have the extreme autonomy crowd. Which, maybe, describes the aspirations of a lot of people in your audience. Which is what we were talking about. “I want to be able to trade my skill for a ton of control over what I work on and how I work on it”.

Then you have the mission crowd who has some overriding mission their whole working life is focused on. That can also be a real source of meaning or passion. The two can overlap. But often the mission people are workaholics, to be honest (laughs). That’s why I put them on ends of the spectrum. You can do both. Obviously, you can be someone who has a ton of autonomy and you decide to work on something that’s very important to you. But they’re often separated.

I looked into: how do these people find a centralizing mission that their whole working life can be built around? The main observation is – they don’t start with figuring out the mission and then go figure out how to act on it. Almost always, the really good missions, the ones that matter, the ones that you really can build a successful working career around and be a source of satisfaction, require that you first become really good in the field.

My best explanation for it is, once you get to the cutting edge of a field, it’s only once you’re there, that you can peer ahead into to what the systems biologist, Stuart Kauffman calls ‘the adjacent possible’. Where you see the new possible configurations of the current cutting edge ideas. It’s in that space that the really cool missions, the really cool innovations, the really cool new ideas, come from.

If you don’t get to the cutting edge, first, you’re not going to be able to identify a practical mission – something that you can reasonably probably build your working life around. There are a lot of exceptions but for the most part, it goes back to this notion as you’ve got to start with the craftsmanship or apprenticeship phase.

It’s just another example of where, when it comes to really loving your working life, we got to change this idea that it’s all about figuring stuff out in advance and then acting on it. It’s almost always action. The action leads to the insights and developments and the satisfaction.

Dan: When you’re exposed to your work, I think for me, at least, one of the clear … you kind of like tasked at the end of the day. ‘Cause you buy into what you’re saying as like, “All right. This guy is right.” It’s like, “Now, I got to work really hard and intensely. That’s what he’s putting on my doorstep, here.” I don’t think it’s that strange then, is that a lot of the posts on your blog are about productivity. There’s this part in ‘Deep Work’ where one of your friends describes, and I have never said this word out loud, only a few times, eudaimonia? eudaimonia-

Cal:   Yeah.

Dan: … eudaimonia machine.

Cal:   Yeah.

Dan: This word is interesting because, I think, it captures a lot more than the word “happiness”. The idea is that it’s a flourishing person. Not just someone who’s happy or satisfied. Can you describe to me the ‘eudaimonia machine’?

Cal:   Yes. I mean, eudaimonia goes back to Aristotle; essentially the Greek notion of what you were trying to do with all of this thinking about how to live is you wanted a life and when you were flourishing as a human. You were living up to the potential of a human being. Therefore, have this flourishing life.

Which, by the way, is a quite a different idea than our sort of modern notion that the key is to find this thing you love to do and match that to your work. I say that only to emphasize – and just to digress briefly – is that when I did research on ‘follow your passion’, people thought it was a timeless piece of advice but the phrase doesn’t show up in the printed English language in the contact and career advice til the late 1980s. It’s a very new concept.

The old concepts that go back to Aristotle and the Greeks at eudaimonia, the stuff that’s been around for thousands of years is actually quite different. It’s not about what do you want to do. What’s the best match for you? What’s going to make you happy? It’s how can you make the most of your potential as human being and feel like you’re really flourishing on all the potentials.

eudaimonia is probably the right thing, in some sense, to have in mind. Much more so than: there’s something out there that I’m wired for and if I do that, I’ll love it. And, where can I get mine?

The ‘eudaimonia’ machine was an idea that an architect friend of mine had. Where basically he was envisioning a workplace that was a linear series of rooms you went through. That prepared you for the last room, which was a completely soundproofed, enclosed space, in which, you just thought deeply about something very important in your professional life. It funneled you towards deep, contemplative, high-value cognitive work, as “this is what is going to lead to eudaimonia in our current age”. It’s so different how most people organize their lives or organize their professional lives that I love the concept.