378: How to Tackle Uncertainty–and Enjoy It with Josh Kaufman

Pete Mockaitis
Josh, thanks so much for joining us here on the How to be Awesome at Your Job podcast.

Josh Kaufman
Pete, it’s a pleasure. Thanks for the invitation.

Pete Mockaitis
Well, I’m excited to get into this discussion. One fun thing I learned about you as I was stalking you in preparation for this discussion is it still active that you have a monthly Dungeons and Dragons group going? What’s the story here?

Josh Kaufman
That is absolutely accurate. Actually, we just had I think it’s our one-year group anniversary this past Saturday.

Pete Mockaitis
Congratulations.

Josh Kaufman
It’s fun.

Pete Mockaitis
Tell me, what’s the – Dungeons and Dragons, it’s so funny. It has all sorts of connotations, but I want to hear straight from the horse’s mouth, what is it for you that drew you in and keeps you coming back?

Josh Kaufman
Oh, it is the most fun game that has ever been invented. It’s this really wonderful combination. When I try to explain it to people who have never played, it’s like imagine a game where literally anything is possible and people can do crazy things that you have not prepared for and don’t expect and there’s some way of figuring out if a character who tries to do something crazy in a story, if they can actually do that thing.

I love it in two ways. It’s this wonderful combination of group storytelling and improv. The storyteller kind of knows where it’s going to go, but doesn’t know for sure. The players have agency and latitude to do whatever they want.

Then the players can explore a world where they can and try and pull off things that are just really fun to think about and come up with creative solutions that the person w ho’s telling the story just never anticipated. It’s this wonderful combination of story and surprise and creativity. It’s the best.

Pete Mockaitis
Not to get too deep into the weeds, but I’m intrigued. How do you make the call on whether something that someone invents out of their head – I guess I just saw matches like “You are locked behind a dungeon door.” It’s like, “I’m going to pull out some – a bazooka and blast it away.”

I guess how do we determine whether or not they in fact can or cannot pull out a bazooka and blast it away? That’s always kind of been my sticking point looking out from afar, having not experienced it first-hand.

Josh Kaufman
Sure. There’s actually very active conversations in RPG circles about how you deal with this. I think the term is verisimilitude, so how much do you want to try to emulate real life in this fantastical story that you’re all telling together.

Every system has different ways of doing it. At least in Dungeons and Dragons, all of the player characters are playing an individual who has certain goals and desires and also, very important, a list of equipment that they have on them at their disposal, so pulling out a bazooka from nowhere is totally not kosher as far as the rules of the game.

Pete Mockaitis
It would be on the equipment list in advance is what you’re telling me.

Josh Kaufman
Exactly.

Pete Mockaitis
Okay.

Josh Kaufman
Imagine somebody like Conan the Barbarian fighting a dragon at the top of a mountain. The dragon is hurt and tries to flee and Conan flings himself off of a cliff and tries to grab the dragon in midair. Most games don’t really have a good system for figuring out what happens next.

The whole point of a rule system in a role-playing game is essentially giving you the tools to figure out just that. What is the situation? How difficult is it? What is this player? What are they good at and what are they not good at?

There’s a way to essentially reduce it to statistics of you don’t know for sure, you’re going to roll some dice to figure out what happens next, but how great are the chances that Conan will be able to leap far enough to get to the dragon and then hold on if they’re able to make contact. Things like that. It’s really fun.

Pete Mockaitis
I see, so you’re kind of jointly deciding that as a group.

Josh Kaufman
Yeah, and the really interesting parts are when the players figure out a solution to a challenge that you didn’t anticipate. At risk of going too deep, my players were fighting ice demons that exploded when they died this past Saturday.

Pete Mockaitis
We’ve all been there, Josh.

Josh Kaufman
Yeah, as you do. It was really interesting to see the group brainstorm and come up with solutions of how to isolate and then put these monsters in a position where they could be defeated without doing damage to the party.

There were five or six different solutions. Every player came up with their own take on it. But it was just really interesting to see with all of the different personalities and the different sets of skills at the table, everybody came up with their own little solution to figure out this thorny problem.

I was telling the story and I had no idea what they were going to do. The fun of it for me was putting a whole bunch of people in a situation and seeing how they tackled it.

Pete Mockaitis
Well, that’s nifty. You’ve compiled some wisdom when it comes to fighting fantastical and mythological beasts in your book, How to Fight a Hydra, but there’s more to it than just a fun fantasy fiction romp. Can you unpack what’s this book all about?

Josh Kaufman
Sure, so How to Fight a Hydra is compiling a lot of research into a universal problem that all of us have that’s we may have a big ambitious goal or pursuit, something that we want for ourselves and we’re not quite sure if we’re going to be able to pull it off. There’s a lot of uncertainty. There’s a lot of risk. There might be fear of the unknown or uncertainty that we have the skills that we’re going to need in order to get what we want.

A huge tradition both in ancient and modern philosophy about how to deal with topics like uncertainty and risk, but also a lot of new cognitive psychology or behavioral psychology. How do you get yourself to do something that you know in advance is going to be challenging or is going to be difficult?

I started researching this and started doing it the way that I did my previous two books, which were research based non-fiction. The funny thing about writing about uncertainty and risk and fear is that if you treat it that way, you start writing a book that nobody wants to read because those topics are inherently uncomfortable to think about too long.

That’s where the idea of instead of explaining how to do this, approaching it from the perspective of a story. Let’s take a person who is deciding to pursue something genuinely difficult, something that they don’t know if they’re going to be able to do and let’s follow them as they go through the process of accomplishing this very big goal and experiencing all of the normal challenges along the way.

Then watch them skillfully apply these things that we know from research works in these sorts of situations. It’s fiction. It’s a story, but it’s a story with an underlying logic and purpose that is very firmly rooted in this universal challenge that we all face.

Pete Mockaitis
I hear you. We won’t spoil the story elements, but within it, there are some components associated with sort of physical training and getting tougher as well as acquiring or crafting a sword in order to pull it off. Could you – at the risk of us entering into the boring territory for the book that nobody wanted to read – what are some of the fundamental steps and scientific insights associated with flourishing when you’re tackling a big project like this?

Josh Kaufman
There are a bunch of insights around – let’s group it around expectations going into something – a new big project, something you’ve never done before, something that is at the limit of your capability. And there are a few common patterns or denominators in how you approach that, and how you approach it makes an enormous difference.

Let’s say you want to enter a new career. You want to start a new business, pursue a creative project. Whatever it happens to be, there’s this undercurrent of, like, “I don’t know if this is a good idea. I don’t know if this is going to work. I don’t know if I invest my time and energy in this way I’m going to get the results that I want. I may have a vague idea of what I’m trying to do, but I don’t know what I’m supposed to do next.”

Those are all very common things that I hear from lots of different people and experience myself. One of the things that’s very useful to know from the beginning is that that is completely normal. It doesn’t mean that you are not up to the task. It doesn’t mean that this is a bad idea or there’s something wrong with you. It’s just a fundamental feature of the world.

These big things that we want to achieve, there’s an inherent element of uncertainty, complexity, variability, ambiguity and risk. Those things are never going to go away. If you understand that from the beginning, you can shift your mindset more from “How do I get this uncertainty to go away? How can I make it stop?” to more of a you are pursuing an adventure. You’re exploring something interesting. You are challenging yourself in important ways.

One of the things that makes an adventure interesting, or exploration valuable, is you don’t know how it’s going to turn out. That’s part of the fun. That’s part of the challenge. Just thinking about these things that we want to do more along the lines of adventures or exploration is a very useful way to think about the process of pursuing something in general.

Pete Mockaitis
That is really cool in terms of just reframing it as an adventure because we pay good money to experience adventure, whether you’re going to REI and buying some outdoor backpacking-type stuff and going out on a trail or a mountain or a campsite or whether it’s more indoorsy, a room escape adventure, you know?

Josh Kaufman
Yeah, definitely.

Pete Mockaitis
Paying money for that kind of experience or just a trip to the movies or a novel or whatever. Yet, elsewhere in life, we want that uncertainty gone. We would like to just sort of know how it’s going to unfold. That’s a pretty clever move in terms of by reframing the uncertainty into adventure, now it’s no longer terrifying and doubt-producing, but rather it’s fun and interesting.

Josh Kaufman
That’s absolutely the case.

Pete Mockaitis
Nifty. I imagine some ways that may be easier said than done, but let’s say you’re in the heat of it. Someone’s looking to change their career wildly from we’ll just say one field of accounting to another field of pinball machine design.

Josh Kaufman
Fantastic.

Pete Mockaitis
We’ve always loved pinball and this is kind of a crazy switch, but they think they’ve got some special skills and abilities and things to contribute there.

Let’s think about it. One person may very well be freaking out in this situation, like, “Oh my gosh, where would I even start? Why would anyone want to hire me? Should I quit my job? Should I not? That’s pretty crazy. How am I going to support my family, pay the mortgage?” Here we are in the midst of uncertainty and big dream and fear. Where do we go?

Josh Kaufman
Yeah, the first bit is exploring more fully what the new thing looks like. I’m guessing that our fictional example may have some experience doing this but may not have completed an entire project start to finish.

One useful thing about thinking about all of these transitions as adventures is there’s a certain amount of exploration that’s always going to happen, particularly at the beginning. There’s actually – I did a full essay about this on my website, JoshKaufman.net, about exploration versus exploitation.

There’s a lot of research about it in computer science, but it’s one of those generalizable things that’s useful in a lot of circumstances. When you’re doing something new, it is in your best interest to spend the vast majority of your time exploring all of your different options.

Maybe in this case, the individual is still working their day job, so there’s some risk mitigation going on there, but then most of the time and energy devoted toward this new activity is spent exploring.

What types of pinball things sound good? What are some of the different industries or businesses that you could work with? What do they tend to specialize in? What do they need? Are you going to build your own pinball machines or are you going to outsource it to a contract manufacturer? Are you selling it yourself or are you selling it through somebody else? There are all sorts of unanswered questions around this topic.

Spending a lot of time and energy in the exploration phase makes a lot of sense. You’re gathering information. You’re trying new things. You are testing to see what are the parts of the business or the venture or project that you really like and what are some of the things that you would rather avoid.

All of that exploration is extremely useful later when it comes to the second phase, which is called exploitation. Exploitation is when you’re spending most of your time doing the things that you know are rewarding.

Imagine you move to a new town and you don’t know which restaurants are good. You spend maybe the first couple years that you live there, you never eat at the same place twice. You explore lots of different options to see what you like and what you don’t like.

But the longer you live there, the more you know what’s going to hit the spot at any particular moment, so you spend more and more time doing the things that you know work and doing less and less of the time with things you don’t.

So for our aspiring pinball designer, after that period of exploration, they’re going to have a much better sense of what works and what doesn’t. Then the more and more things that work, the easier it’s going to be to make a transition from accounting to pinball.

Pete Mockaitis
That’s intriguing example there when it comes to the food. It’s so dead on because I found myself, particularly when I’m at a restaurant that I’ve been to several times, it’s like I’m torn. It’s like, okay, there’s one thing I know that will be delicious and wonderful, so I’m naturally drawn to that and yet, I’m also intrigued by the new and seeing what could be there.

I’ve had it go both ways. I try something new and it’s like, “Wow, that was even better than the thing I loved. I’m so glad I did that,” versus “Oh, this is kind of lame. I could have just stuck with the thing I knew was good and then been feeling more delighted post meal.”

I like that you’ve provided a particular rule of thumb here, which is in the early phases, you’re going to get a better bang for your buck by doing more of the exploration versus once you know the lay of the land, you’ll have a better return by doing the exploitation.

Josh Kaufman
Absolutely. And the additional wrinkle to this, so this is often in the research literature called the bandit problem because the classical mathematical formulation is you’re playing slot machines, which I do not recommend by the way, but for the sake of understanding, it’s a good example.

Imagine you go into a casino and you can play any slot machine you want. You don’t even have to spend money. It’s just the time that it takes to pull the lever and see the result. If you’re given this opportunity and you want to maximize your return from this experience, what do you do? Well, that’s where the exploration and the exploitation phase comes it.

You spend quite a bit of time testing different machines gathering data. Then after a while you start shifting to the machines that you know provide a much better pay off.

The interesting thing is you would think at a certain point that exploitation is the way to go. You just do the thing you know works over and over and over again. When you look at the studies and you look at the math, that’s actually not the case. There’s always a certain amount of your energy and attention that is going to be devoted to exploration because you don’t have perfect information about what is going to be the most rewarding thing you possibly could do.

The more time you spend, the more confident you can be that you’re on the right track, but it’s always beneficial to you to reserve at least some percentage of your capacity for trying new things and seeing if they work out.

Pete Mockaitis
Indeed. I guess it’s just my personality or strengths or whatever, it’s just like I find that exploration of the new is so much more exciting and interesting.

Josh Kaufman
I’m right there with you.

Pete Mockaitis
And sometimes to my detriment. It’s like, “No, no, Pete, just continue doing the thing that’s really working for you instead of gallivanting off to some crazy thing,” but the gallivanting is fun. I guess when you talk about the context of slot machines, which is gaming is for the purpose of fun, then that may be all the more true.

Josh Kaufman
Yeah, I think a lot of it comes down to – in the personal context, why are you doing this thing in the first place? There may very well be situations or decisions that you might make from a career standpoint that might get you a lower financial return than other options, but if you have a payoff in another dimension, so maybe it’s personal interest and engagement maybe it’s exploring an area that you really love and you’re willing to make tradeoffs in order to work in that area.

There are all sorts of things to optimize for that aren’t necessarily financial return. I think the more broadly you think about what’s the reward for this thing that I’m trying to do and how can I get more of the things that I care about, the easier it is to make those sorts of tradeoffs.

Pete Mockaitis
Well said. Okay, when it comes to the hydra fighting, any other kind of key takeaways that you think are particularly on point for those seeking to be awesome at their jobs?

Josh Kaufman
Yeah, I think the understanding that it’s going to be difficult and that’s okay, is a really great mental framework to begin and that most of these sorts of challenges are met by both improving your skills, so getting better at doing the things that are critical to achieve the results that you want, and persistence and specifically persistence in the face of frustration and difficulty.

And so it’s very easy, particularly early on – this is actually a theme in my second book, The First 20 Hours. When you’re doing something new or something you’re not familiar with or something you’re not very good at yet, that early experience of trying to make progress and not getting the results you want is extremely frustrating.

Understanding that persistence is the thing that allows you to push through those early barriers and solve the challenges and get what you want, the more you can understand that that is the path to victory. It’s not being naturally skilled. It’s not having some sort of magic problem-solving device. It is consistent effort, attention and energy over a long period of time.

That is setting you up for success in a way that a lot of messages in broader culture, just don’t really help you with.

Pete Mockaitis
Could you give us a couple, quotables or articulations of the counter message that’s suboptimal?

Josh Kaufman
Well, I think the best way to frame it—that I’ve seen in various forms is don’t compare your inside versus somebody else’s outside. social media does not do us many favors here because you tend to see the highlight reel of other people’s lives. You see the promotions. You see the vacations. You see the raises. You see the major status-oriented achievements. You don’t necessarily see, the struggle or the fear or the anxiety or the work that goes into a lot of  the achievements that other people have.

Understanding that everyone deals with the same challenges of not knowing what’s going to happen next, not knowing if an investment is going to pay off not knowing if something is a really great idea that’s going to change their life or career or a terrible idea that is going to blow up their life or career. It’s a universal problem.

Giving yourself a bit of grace and being comfortable saying “I may not be where I want to be yet, but I am on a path and I am working towards getting there,” that goes a very long way.

Pete Mockaitis
Not to kill dreams prematurely, but I guess the counter side of persistence is knowing when is it appropriate to shut down a plan that is not going to cut the mustard. Any pro tips on that side of things?

Josh Kaufman
Yeah, the biggest advice I can give in that regard is be very, very clear about what you want upfront. The way that I like to think about this most people’s goals or dreams if they’ve articulated them to themselves are very broad and very general. Broad and general to the point where it doesn’t really give your brain anything to work with in figuring out how to get there.

The acronym or approach that works really well for me is PICS, P-I-C-S. That’s positive, immediate, concrete, and specific. Those are the qualities that should apply. When you write down what you want, try to make it as concrete, specific, vivid and something that you can look into the world and figure out, “have I achieved this thing or not. Am I there?”

“I want to climb a mountain,” is very not specific. “I want to climb Mt. Everest by next year,” is much more specific. You can do something with that.

Pete Mockaitis
I like the acronym PICS just because that’s kind of what you’re getting at is we’re trying to paint a picture that’s super clear, that we know if we’ve hit it or have not hit it.

Josh Kaufman
Yeah, the more vividly you can imagine what your life looks like and what this thing you want to achieve looks like when it has been accomplished, the more useful it is going to be in terms of figuring out what to do next to get there.

Pete Mockaitis
That’s excellent. Then it’s easier to make that call. It’s like, “This is what I was going for and what I’m experiencing is in no way, close to that nor getting closer to it, over time,” so there you go as opposed to if it were fuzzy, it would be tougher to know that we’re not where we’re headed or where we wanted to be.

Josh Kaufman
Yeah, I think a lot of people experience that particularly early on in their career, where they have this image before they enter the workforce or in a new role about what it’s going to look like and what it’s going to feel like and what their life is going to be. And a lot of times, the early experiences don’t match up very well with that. it helps to be able to really articulate what am I trying to get out of this, what is the benefit for me, what do I care about and what do I not care about so much? And then be able to figure out, okay, on a day-to-day basis, is this thing taking you closer in the direction of where you want to be or is it actually taking you farther away?

In my corporate career, I was actually in product development in marketing at Proctor & Gamble, which a huge consumer goods company. I was really excited. I loved creating new things. That part was really great. I decided to move on from the company when I was in a meeting to prepare for a meeting to prepare for a meeting to prepare for a meeting.

Pete Mockaitis
Could you unpack that?

Josh Kaufman
Four levels of ….

Pete Mockaitis
The layers of the meetings. I’ve got to hear this.

Josh Kaufman
A lot of how product development works was we’re individual teams who are working on things and they would essentially pitch it to the vice president/president level in order to get funding.

I was having a meeting with my manager to prepare for a meeting with the brand manager of the product that this would be under to prepare for a meeting with the marketing director, and then to prepare for a the final pitch to the vice president and president to get funding.

And all of those meetings were important. And then I just looked at my life. I’m like, “I don’t want to exist in meetings for the rest of my career. There are other things I want to do.”

Pete Mockaitis
What’s intriguing is that the final, final meeting was still an internal one as opposed to say a venture capitalist or Wal-Mart, Amazon. Are they going to carry your product? It was still an internal one.

Josh Kaufman
Yeah, absolutely. I actually had quite a few meetings with Wal-Mart and Target and Costco and all the big retailers and somehow those were more straightforward than the internal meetings about how to allocate funding. It’s kind of funny.

Pete Mockaitis
Intriguing. Okay, well, so that’s a little bit about the hydra story. I cannot help myself if I’m talking to Josh Kaufman, I’ve got to get some of your wisdom when it comes to self-directed learning. I first heard about you when you came up with the notion of the personal MBA which sounds great. What’s your take here in terms of should nobody pay for a traditional MBA and how do you view this world?

Josh Kaufman
I think that if you’re already working at a company you like, you know you want to move up in that company internally there’s a requirement to have an MBA, uh, to have the position that you desire and the company is willing to pay for it, then that’s probably a pretty good reason to do it.

Pete Mockaitis
Okay, some stringent criteria.

Josh Kaufman
Yeah. Anything else aside from that it’s probably going to be more expensive, both in terms of financial time and opportunity cost than you expect and the value of the credential in and of itself is just not really great. In a financial sense, it’s almost always a negative ROI.

If the goal is to understand what businesses are, how they work, and either how to start a new business or make any existing business better, you can learn how to do that on your own. You don’t necessarily have to spend years and tens, hundreds of thousands of dollars to learn business skills. Business skills are very learnable on your own.

The goal with The Personal MBA was to create the best possible introduction, that I could make to the world of business. So assuming you know absolutely nothing about how businesses work, how can you understand all of the parts, that go into making a business work in a way that allows you to do important stuff, whether that’s making a new product, new company or just doing better in your existing job?

Pete Mockaitis
All right. You did a nice job of unpacking the key sub skills that are associated with the MBA and then you’ve got an infamous – maybe just famous, I don’t know about infamous – reading list associated with when it comes to strategy and these marketing and all these things that are handy to know to comprise what an MBA knows and getting there.

I’d love to get your take then when it comes to doing this learning on your own as opposed to in a classroom or a group environment, what are some of your pro tips for pulling that off successfully outside those supports?

Josh Kaufman
Yeah. I think the biggest thing is aside from the basics of setting aside time to read and research and think and apply, that’s going to be necessary in any case. There’s a particular type of thing that when you’re self-studying you should, look for.

A lot of traditional academic book learning is all about memorizing terms and techniques, so specific things that apply in specific situations. I think a much better way to approach learning for application in general is to look for things that are called mental models.

A mental model is basically a conceptual understanding about how a thing in the world works, what it looks like, how different parts of a system interact with each other. It’s essentially one level of abstraction higher.

It’s being able to see the same principles at work in, businesses in different industries, different markets, different products, products to services, understanding how things work at a deeper level and that gives you the ability to look at a situation you’re not familiar with and that you have no context about and have a place to start and have a place to figure out how you would go about getting more information or make decisions in this particular area.

And so, The Personal MBA is really designed around that idea. Let’s learn the most important mental models about business, about people because businesses are created by, run by, and run for the benefit of people, so let’s understand psychology and communication and how that works.

And then systems because most successful businesses are essentially comprised of systems, processes that can be repeated in order to produce a predictable result. The more you understand about systems in general, the more you’re going to be able to take that back to a functioning business or a new business and say these are the things that would probably make the biggest difference right now.

Pete Mockaitis
Could you give us an example of a mental model? It’s like, “Oh, because I understand this one thing, I can now take that with me and apply it to having a starting point for this other thing.”

Josh Kaufman
Sure. So one of my favorites, which is, early in the book for a reason is what I call the five parts of every business. And it’s uh, this very universal way of deconstructing a system or deconstructing a business into, universal parts that help you understand how it functions at a very fundamental level. The five parts are value creation, marketing, sales, value delivery, and finance.

Every business creates something of value to other people, could be it products, could be it service, could be a shared resource like a museum. There are all sorts of different ways businesses create value, but it always makes something that other people want or need. So it’s important to understand what that is and why people want or need it, how that value is created to the people who ultimately pay the business’s bills.

Marketing is all about attracting attention for this valuable thing that you’ve created. So how do you make sure that people know that you have something valuable to offer them?

And then from there, you can attract all the attention you want, but if nobody ever pulls out their check book or credit card and says, “Yes, please. I’ll take one,” you don’t have a business. You have something else. And so sales is the process of taking someone who is interested in what you have to offer and then encouraging them to become a paying customer of the business. It’s the part where, money flows into the business instead of running out.

It turns out, if you take people’s money and you don’t deliver what you promised, you’re not running a business; you’re running a scam.

Pete Mockaitis
You find yourself in prison.

Josh Kaufman
Exactly. So value delivery is the part where you have a paying customer. This is great. You have something valuable that you’ve promised to deliver them. Let’s deliver this thing in a way that makes the customer deliriously happy. This is everything from the construction of physical products, the, service, delivery, follow-up calls, and all of those things that turns a paying customer into a happy customer. That’s all in value delivery.

And then finance is essentially the analytical step. So, in, value creation, you’re usually spending money to make this thing. You’re investing. Same with marketing. You may be spending on advertising. You may be spending on any form of outreach to attract more attention to this thing you’ve made.

Sales is the wonderful part where money comes in. Then value delivery, when you are making your customer happy delivering what you’ve promised, you’re usually spending money there too.

And so finance is the process of analyzing all the money that you’re spending and all the money that you’re bringing in and answering two very fundamental questions. One, is more money coming in than is going out, because if not, you have a problem. And then, number two, is it enough. Is it what we’re bringing in from this system worth the time and energy that it’s taking to run the whole thing?

And no matter how large or small the business is, whether you’re one of the largest companies in the world or you are a company of one starting something new for the first time, if you’re bringing in money and it’s enough and it’s worthwhile to keep going, congratulations, you have a successful business. That’s all it takes.

Pete Mockaitis
Okay, so then that mental model there is you just said, hey, we’ve got these five components, so even if I know, know jack diddly squat about, real estate investing and, buying homes and renovating them and renting them out, by applying this model of the five key areas, I can sort of quickly get an understanding in terms of saying, “Okay, what is it that customers, people who rent apartments want?” and then away you go.

Josh Kaufman
Yeah, that’s exactly it. I was doing consulting and advising related to personal MBA for many years. It was really fun talking to people who worked in wildly different industries and markets, being able to come back to the same core process of okay, I may be speaking to someone who is implementing electronic health care records for midsized doctor’s offices with 10 to 20 doctors practicing.

That’s not an area that I had any direct expertise or experience in, but coming back to this framework, it was very easy to understand what was going on, what was important, where the opportunities were just based on a conversation around, “okay, these are the areas of this particular business that I need to know before we can dig in on here’s what’s going to be most beneficial and what you should focus on.”

Pete Mockaitis
Understood. Thank you.

Josh Kaufman
Sure.

Pete Mockaitis
Okay, well so then I’d love to go a little bit deeper when it comes to the how associated with, developing these skills. You’ve laid out kind of a four-step approach for learning a new skill within a mere 20 hours, not 10,000. How does this go?

Josh Kaufman
Yeah. This is part of my research for I did for my second book, The First 20 Hours. The goal for that one was to understand how to go from knowing absolutely nothing about something you’re trying to do to being reasonably good in a very short period of time. Usually that early learning is slow and frustrating, so anything that we can do to make it a little bit faster and way less frustrating is going to beneficial for us long term.

That goes back to the PICS acronym we discussed earlier. Like, getting very clear, very specific about what you want to do, how you want to be able to perform, and what that looks like when you’re done.

And so from there you’re able to take that image of what you want and, do what’s called deconstructing it into smaller parts. usually the skills that we want to learn, aren’t single skills in isolation. They’re actually bundles of different skills.

So a good way to visualize this is imagine a complex game like golf. So playing golf actually involves lots of different things. I don’t play myself, so apologies if the terminology is wrong. But driving the ball off of a tee and putting it into the hole, on the green, are two very different things.

And so the more you can understand what those isolated sub skills look like and which ones are most important to get what you want, the easier it is to practice the things that are going to, to give you the best return for your invested time and energy. You practice those things first.

Learning just enough to go out and be able to correct yourself as you’re practicing gives you the biggest return.

Too much research can be a subtle form of procrastination. That’s actually something that I, struggled with quite a bit. I want to know everything about what I’m trying to do before I do it. Spending just a little bit of time and energy researching just enough to go out and try to do it and to be able to notice when you’re doing something wrong and then try, go back again and self-correct. That’s really important.

There are two other things that are particularly important, so removing barriers to practice, some of those barriers can by physical, mental or emotional. Make it as easy as possible for you to sit down and spend some dedicated time getting better at this thing that you want to do. Then pre-commit to learning the most important sub skills first for at least 20 hours.

The pre-commitment is a very powerful tool from a psychological standpoint that makes it much more likely you’re going to practice long enough to start seeing benefits. So the early hours, super frustrating, so you need to have some type of method, some way of getting past that early frustration.

And the best tool that I found is pre-committing to a relatively short period of time and I recommend 20 hours as a nice happy medium for most of the skills that we would learn either in a personal or professional context.

Pete Mockaitis
That’s handy with the pre-commitment upfront. “Hey, this is what it’s going to be and I’m ready for it. I’m strapped in and we’re kind of pushing past it,” as opposed to, “Hey, it turns out I’m not good at this and I hate it, so we’re done.” That’s nice there.

When it comes to the sub skills, could you – I imagine it varies quite a bit skill to skill – but could you give us a further example of, what’s the approximate breakdown in terms of when it comes to sub skills, I think I might make it a bit too granular in terms of “There are 83 sub skills.” What do you think is kind of the right level of detail when defining the sub skills that we’re going to tackle?

Let’s say I want to be handy. I’m a homeowner now. I want to be handy around the house. It’s like, okay, well, we can talk about screwing screws. We can talk about drilling holes. We can talk about drywall. We can talk about furniture assembly, etcetera.

I think that it might be possible to subdivide it into a huge number of things and maybe, well, hey, being handy is a very broad thing that warrants that. But could you give me a sense for what’s roughly the right size of the piece when we think about a sub skill that we’re going to get our arms around?

Josh Kaufman
Yeah, so in an instance like that, I’m really glad you brought it up because you’re right, being handy is like a state of being that you develop over time. It’s hard to look at your day-to-day life and experience a moment where you think to yourself, “Wow, I have really accomplished being handy.”

Pete Mockaitis
I have arrived at handiness.

Josh Kaufman
Yes, like I’m here. But one thing that’s really useful in situations like these is to think in terms of discrete projects. So look around your house for all of things that you would want to change or improve.

So I think the drywall example is a really interesting one. Let’s say there’s a section of your house where for whatever reason the drywall needs to be replaced. Maybe it has dents in it. Maybe it wasn’t done well the first time, who knows. But there’s some section of wall where you want to do that.

That is breaking down this very meta ‘I want to be handy’ into ‘I want this particular section of my house to look good and having it look good requires drywall work.’ That gives you the context to figure out, “Okay, if I’m going to work on this piece of the house, here are all of the things that I’m going to need to learn how to do and here are some of the tools I need and here’s how I’m going to have to figure out how to get the drywall down.” You can start breaking it into smaller and smaller parts.

And then the practice of it might look like saying, “Okay, I’m going to try to replace this myself. And I’ve never done it before. I’m a little hesitant to do it, but it’s either going to be done or I’m going to put 20 hours into the doing of it.”

If you’re terrible and everything looks horrible and you need to hire somebody to fix all of your problems after the 20-hour-mark, great, but in the meantime you’re going to focus on solving this specific problem with the time you have allotted to it.

Pete Mockaitis
What I love about the 20 hours, to jump in there, is that it’s – on the one hand that seems like a crazy big amount of time if you think about someone who already knows what they’re doing. It’s like, this could be a one-, two-, three-hour job max for, uh, someone who’s uh, experienced with drywall. But you have laid it out that I’ve pre-committed to the 20 hours. The goal is to learn the thing such that I can deliver on this one project.

I think that does a huge service in terms of short-circuiting that frustration because if—if you find yourself in hour 16 like “This is insane. It’s taken me over five times as long as somebody who knows what they’re doing would take them,” you’d be like, “Ah yes, but I’m almost done and according to my 20-hour commitment, therefore I’m winning.”

Josh Kaufman
Yeah, totally. I really like um – there’s just something about making the commitment that short circuits all sorts of very detrimental things. The First 20 Hours, the first edition of the book was published in 2013.

And now like, five years later, having lived with this for a long time, every time I pick up a new skill, I have to think to myself, “Okay, I’m going to do this. If I’m terrible, I’m going to be terrible for 20 hours. If I don’t like it, if I’m having a miserable time, then I only am going to be miserable for 20 hours and then I can stop.”

But just making that mental shift of it’s okay if I’m not good at the beginning. It’s okay if it’s frustrating. I’m just going to push through that because I know that if I stick with it long enough at minimum I’m going to be a lot better than I was when I started.

Um so, there’s just a whole lot of excellent goodness in both letting it be hard, like not expecting it to not be because it very often is. It usually is. But then also helping to really shift into the mode of, um, not comparing your skills or abilities versus other people who have probably been doing it for a lot longer than you have.

Like, that’s a huge trap, both in skill acquisition, but also in business and creative endeavors in general. Like looking at somebody else and their level of development and expecting ourselves to have those skills and that level of development from hour zero.

This—this approach really helps you to hone in on, “Okay, where am I right now? Where do I want to be?” And then as you’re putting in the time, you can see yourself getting better and better and better.

It’s called the Power Law of Practice. It’s one of the most reliable, effects or studies in cognitive psychology. The first few hours that you practice something new, you will get dramatically better very, very quickly. It’s just a matter of sitting down to do the work in the first place and then persisting long enough to actually see that improvement happen.

Pete Mockaitis
I dig that. I also really appreciate the notion of the comparisons and how, I guess, silly and futile and unproductive that is in the sense of I can imagine, it’s like well, you can think about something that you’re amazing at and then say, “Well, what if my contractor tried to start a podcast or deliver a keynote speech or write a book?” It’s like, things that I’m good at.

It’s like, “Well, he’d probably not so graceful and elegant, kind of the way I do right now as I’m hacking through this drywall and doing a comically poor job.”

Josh Kaufman
Absolutely. That’s exactly the way to think about it. Like, there are things that you have become amazing at because you have learned and practiced consistently over a very long period of time. That—that’s just how humans fundamentally improve at everything.

And so you can take that general insight is if you approach the early part of the process in a skillful way, so knowing it’s going to feel hard and it’s going to feel frustrating. And that’s okay. That’s expected. If you can get through that early part, then you can become better at anything that you put your mind to. It’s mostly a decision of what to work on and of all of the things that you could work on or improve at, what are the things that are going to give you most of the results that you want.

Pete Mockaitis
Excellent. Well, Josh, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Josh Kaufman
This has been really great. I think the um, underlying theme of my work in general, and I have some new books that are in various stages of, of research right now, but I really try to focus on, on the, uh, straightforward, practical wisdom if that makes sense, just trying to understand important areas of life, figure out how to get really good results in that area, and describe it in a straightforward way.

If anyone decides to explore my work, I really hope that’s what they take away, whether it’s business or learning a new skill or tacking this big ambitious project you’ve always wanted to do, I hope you’ll take away some, um, very straightforward, very practical approaches and techniques that will help you get what you want.

Pete Mockaitis
All right. Awesome. Well now then could you share with us a favorite quote, something you find inspiring?

Josh Kaufman
I love quotes. I collect them. It’s hard to pick a favorite. So there’s one attributed to Andy Rooney that I think about a lot, which is, “Everyone wants to live on top of the mountain, but all of the happiness and growth occurs while you’re climbing it.”

Pete Mockaitis
Thank you. How about a favorite study or experiment or bit of research?

Josh Kaufman
Well, all of my books are my collected research,so that’s kind of an ongoing uh, uh project. Part of how the personal MBA came to be, was reading a bunch of business books and—and pointing folks to the ones that I—I found most useful.

A book that I’m in the process of reading now, by Mo Bunnell called The Snowball System, which the best way I can describe it is like, sales and business development for normal people, who may approach the sales or business development process with a little bit of trepidation or not wanting to be a salesy person. Mo does a really, really great job of making sales and relationships very practical and very accessible. I’m about halfway through it and I’m really enjoying it so far.

Pete Mockaitis
Excellent. How about a favorite tool?

Josh Kaufman
Favorite tool. Well, we were talking about this a little earlier. I’m doing a lot of podcasts and audio book recording.

Pete Mockaitis
Yes, you sound amazing.

Josh Kaufman
Thanks, yeah. So, so the microphone I’m talking into right now is the Mohave Audio MA-200. No joke I ordered I think it was 12 different microphones from various manufacturers. I spent—I spent like three solid days recording the same thing into each microphone and trying to compare how they sounded. This one is a really good one. If you do any sort of recording of any sort, I would highly recommend it.

Pete Mockaitis
How about a favorite habit?

Josh Kaufman
Favorite habit, so I am,  in the process of really firmly establishing a strength training routine. I have been exercising with kettle bells, which I love for all sorts of different reasons. They are inexpensive and compact. I used to live in New York City, so I could imagine myself having this in my former 340 square foot apartment. You can get a really excellent workout in about 25 minutes. In terms of return for your time and effort invested, it’s really high. You don’t have to spend hours in the gym every day.

Pete Mockaitis
Is there a particular nugget you share that really seems to connect and resonate with folks? They keep retweeting it and quoting you back to you.

Josh Kaufman
I think that one of the recent ones, which was related to Hydra, is about the idea of exploration. By virtue of doing it, you’re kind of committing to wandering lost in the woods for a while if that makes sense. So many of us feel really bad when it’s not immediately obvious where we should go next or what we should do next.

Part of understanding that this is an adventure and that adventure requires exploration and exploration involves being lost for a while. That’s something that a lot of people have seemed to find very useful recently.

Pete Mockaitis
If folks want to learn more or get in touch, where would you point them?

Josh Kaufman
Best place to go is my website, JoshKaufman.net. From there you can find links to the various websites for The Personal MBA, The First 20 Hours, and How to Fight a Hydra.

Pete Mockaitis
Do you have a final challenge for folks seeking to be awesome at their job?

Josh Kaufman
Sure. We’ll go back to our conversation about defining very clearly what you want, what that looks like, what your day-to-day life looks like when you get it, what you’re going to be able to do when you reach the level of skill or development that you’re looking for.

The more clearly you’re able to articulate to yourself what you want, what that looks like, and very importantly, what you’re not willing to do in order to get it – so are there lines you won’t cross, are there tradeoffs that you’re not willing to make? The more you are able to understand the full details, the full scope of what you’re trying to get, the easier it’s going to be for you to figure out how to get it and figure out what you should do next.

Pete Mockaitis
Well, Josh, this has been a load of fun. Thanks so much for sharing your expertise with us and you’re lovely sound over on the microphone.

Josh Kaufman
Thanks.

Pete Mockaitis
I wish you tons of luck with the hydra fighting and all you’re up to.

Josh Kaufman
Pete, this has been great. Thanks so much for inviting me.