How to design your life step by step?

New York Times bestselling author Bill Burnett is with me for an hour to enlighten us with a series of revolutionary, life changing concepts about how to use design thinking to dramatically improve our careers and lives.

As the Executive Director of the Design Program at Stanford, he got his BS and MS in Product Design at Stanford and has worked professionally on a wide variety of projects including 7 years at Apple and a number of years in the toy industry designing Star Wars action toys.

He’s the Co-Author of the NYT Best-seller Designing Your Life which has sold more than 1 million copies in 24 languages and his work is truly having a global impact.

I did this interview with my former business partner Lauren Weinstein.  If you want direct access to more amazing interviews like this one with Bill, consider joining my Inner Circle coaching community where you’ll get access to some of the most amazing thought leaders today!!

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Full Episode Transcript:

 

Bill: Adopting the mindset of curiosity, radical collaboration, bias to action, getting out in the world to test your ideas, your thoughts, your gut feelings, your whatever, it’s so empowering. And once you’re unstuck, you’re unstuck permanently. Because as soon as you hit another roadblock, you just apply the same principles and get unstuck again. 

Todd: Welcome everyone to an exciting episode of untapped. My name is Todd Jason, and I’m sitting here with my cohost, Lauren Weinstein, and we’re both incredibly excited, and honored to have New York Times bestselling author, Bill Burnett, with us today, who’s going to enlighten us with a series of revolutionary and life changing concepts about how to use design thinking to dramatically improve our careers and our lives.

It’s really exciting stuff. And this topic is spot on with our mission in Untapped, which is to bring you the most fascinating, successful people we can find who found powerful ways for each one of us to have more joy, more purpose, and fulfillment in our lives and our work. And our goal with each conversation is for you to receive one or two relevant pieces of information that you can apply in your life starting today that can help you untap more potential and excitement.

So, definitely take some notes. And Bill Burnett could not be a better guest. As the Executive Director of the Design Program at Stanford. He got his B. S. and M. S. in product design at Stanford and has worked professionally with a wide variety of projects, including seven years at Apple and a number of years in the toy industry, designing Star Wars action toys.

I mean, how cool is that? He’s the co author of the New York Times bestselling, Designing Your Life, which has sold more than one million copies in 24 languages, and his work is truly having a global impact. So Bill, thank you so much for being with us here today. 

Bill: Well, thanks for the invitation. I’m excited to talk with you guys about this stuff.

Lauren: Yes. Thank you so much for being here. So happy to have you and of all our interviews, this is personally the most meaningful for me because design thinking what you teach completely changed my life. A brief story for our audience. I was in law school, pretty unhappy. About to start studying for the bar, about to accept an offer at a corporate law firm.

I was pretty sure this wasn’t a fit, but I wasn’t sure what else to do or how to get off this track I placed myself on. And then I took a course at the design school where Bill teaches, a class called design thinking bootcamp. It completely shifted my mindset and gave me the tools I needed to put myself on a very different path.

Fast forward, I became a coach, ended up teaching at Stanford Business School, gave a TED Talk, I’m sitting here right now with Bill in an interview. So completely like beyond my wildest dreams, this life that was created through design thinking through this course. Uh, so first, thank you, Bill, for the work that you do and complete testament that, that it works.

This is really powerful. And so to start, the first question we have for you is.

I think many in the audience can relate to my story. So you choose a path, you think it will make it happy, or it seems like the right choice at the time, but then years later you find yourself unhappy and unfulfilled, or maybe your life feels fine, but definitely not joyful and well lived, as mentioned in the subtitle of your book.

So let’s say I come to you with this challenge. What would you tell me? How would you counsel me or help me think about this problem? 

Bill: Well, a couple of things Lauren and um. Anecdotally, a lot of people who do show up and ask that question are lawyers who don’t want to be a lawyer anymore. I think, first of all, the first thing I tell everybody is, look, you didn’t, you did nothing wrong.

You made you, you made good choices with the data you had at the time, but now you’re checking in with yourself and you’re saying, something doesn’t feel right, or this isn’t feeling like the,, either it’s enough or it’s, or it’s really where I want to be. And so, design starts in reality and there’s a big sign over the master students have a studio we call the Loft. There’s a big sign over the loft saying you are here. And in fact, if you take the dust jacket off of the hardcover. Version of presenting your life. You will find a little symbol that says you are here Which is just to emphasize to people that hey, wherever you start is fine however, you got here is fine. The process of almost being a lawyer and then deciding to do something else for becoming a lawyer a doctor investment person I meet a lot of bankers and investors who are unhappy it was a you did the best you could with the tools you had at the time.

So one don’t beat yourself up Let’s just start from where we’re at. This design starts in reality and all designs are, an attempt to take whatever we have now and make it better. When I was at Apple, we did the first notebook computers, the PowerBooks, PowerBook 140, 160, 170, and then we made them better.

We made them better. we made it better. So you just start where you’re at. But I think what happens is a lot of us get on what psychologists call the hedonic treadmill. We work really hard in high school and we go to college and then we work really hard in college and then we go to grad school and we work really hard in grad school and then we get a job and we work really hard in the job and you know there’s always a ladder and there’s always you know junior analyst, senior analyst, junior partner, whatever.

And so we get on that treadmill and it feels pretty good to get the next, to get to the next level, like in a video game, right? But what happens over time is that it felt pretty good for a while and then I didn’t feel that good after about a year. And then it felt really good for a while and then the next promotion, and then it didn’t really feel that much different after six months.

And pretty soon, I either need twice the high or, twice the hit because, it’s just not working for me. So once, once you come to that realization, which is great. You can start to make a change because we say, design thinking starts with empathy. Don’t start with people, start with the problem.

Empathy, define, ideate, prototype test. But in designing your life, we had one more step, which was called accept. Let’s accept that I want to change something. My buddy, Dave, who I write the books with has a favorite saying you can’t solve a problem you’re not willing to have. So until we decide, wait a minute, this law school thing, this is not, there’s something wrong.

I’m not exactly sure what it is, but I’m pretty sure my guts telling me this is not my path or, I meet a lot of people in their mid thirties and forties saying, I really enjoyed being a program manager in a small tech company. I really enjoyed being a a project lead on, this kind of stuff in my social, , social enterprise.

I just don’t want to do it anymore. I have grown out of this role. I need, I want to do something else. And the data says you’re going to have two or three different careers. That’s normal nowadays. The idea of, working one place in one career for, 40 years of retiring, that just doesn’t happen anymore.

And so I think it’s, I think that’s an opportunity once you realize that you want to change. And then you just need some tools to figure out, well, all right, I don’t want to be on this treadmill anymore, but I don’t really know what I’m looking for other than the next, the next thing, the promotion, the job, the thing.

So I got to stop. I got to take stock. We have people write a life view. What’s your view of life in 250 to 500 words or less? And what’s your work view? What’s work for? Not your job description, what’s work for? Then we put those two together, we try to figure out how to make them coherent, and that gets people started on the journey of finding out what might be next for them.

And I think just knowing that there’s going to be multiple nexts, and there is no one best answer, gives people a lot a lot of relief and allows the creative side of the journey to come forward. So I’d say in short, there’s nothing wrong. Whenever you decide you want to change this is the right time to decide you can’t solve a problem you’re not willing to have.

So once you’ve decided it’s your problem, I need to figure out something different. Then we need to do a little bit of introspection and a lot of design to figure out what’s next. 

Todd: No, this is awesome. I’m such powerful stuff. I love the fact that we’re starting with acceptance, right? We’re starting with the idea that We’re okay.

Exactly where we’re at, which is very relevant to the work that Lauren and I do. Before we go deeper into the tools, because you laid out some of the tools of designing your life and your main principles, I want to ask you about, self rationalization, right? And so what I’m, what I mean is that one challenge that we often see is that people will be pretty unhappy in a toxic work environment or working with people that are really consistently challenging.

 And they’ll be unfulfilled, but they’ll say to themselves, that’s just the nature of the job, or I just need to push through, or it’s fine, when really it might not be. Okay, so now in the book you share that we can’t solve a problem that we’re not willing to have, as you just said, and you call this a gravity problem.

So talk a little bit more about this and this notion of when someone is self rationalizing these things, what do you say? 
 

Bill: One of the reasons people will take the class or they read the book is because they’re stuck. Like you said, they’re stuck. I’m in this job, it’s not very good, or I’ve got a really toxic boss, or it’s just, I just don’t feel like, I’m not, I thought I was going to, do something that was meaningful and important, and I’m just pushing papers around, or I’m just dealing with this bureaucracy, and so they’re stuck.

And there’s some kinds of stuck like what we call a gravity problem. You can’t change gravity, right? So , I’ll give you a simple one. I went, I was seven years at Apple. And the reason I left is I just didn’t want to do computers anymore. And I, I asked around. We don’t, Apple doesn’t do refrigerators, doesn’t do toilets, doesn’t design, banking apps.

It just does computers. And so, once you accept that whatever my organization is and whatever the circumstance I’m in isn’t going to change, then you say, alright. I’ve accepted that this is the organization and this is the way this job works. And I’ve done some, we have another thing about don’t resign, redesign.

I’ve done some redesign opportunity. I’ve looked at the opportunities to redesign my job. It just isn’t going to happen. Then what you do with a gravity problem is you say, you’re right. There’s nothing I can do about gravity, but what can I act on? What parts of this situation can I act on? And you always have some freedom to change.

I don’t mean that you can just quit your job and walk away and say, take this job and shove it or anything like that. When I decided to leave Apple, just because I just wanted to try other things, I spent a year leaving well, setting up the people who are working for me with good roles, that they would be taken care of, making sure that the projects that I thought were important were, handed off to people who were really effective. 

Design is a long game. And you start by saying there’s some stuff I can’t change, just stop me, like, what’s the old joke? How many psychologists does it take to change a lightbulb? Well, it just takes one, but the lightbulb has to want to change. So if you’re not going to change your organization, most likely.

Bill: And certainly, we have a thing in the second book on work, Designing Your Work Life, on if you’re burned out and there’s a we put the male clinics burnout, assessment in the class. If you’re burned, literally burned out, that is a medical problem. That is a technically a medical problem.

You can’t design your way out of being burned out. If you’re in a toxic work environment, literally. You’re being harassed, , sexually harassed, ageism, sexism, racism, whatever it is, you’ve got dysfunctional organizations, when you try to report the behavior, nothing changes.

You don’t deserve to be in that kind of a situation. And it’s not just suck it up and keep going. So things like that, I think, require you to take action and make a change. And just to preserve your self worth, dignity. But you have economic constraints, you have other constraints, family constraints.

So, Sometimes it’s, in the gravity problem thing, it’s like, okay, except this is not possible to change. Is there any framing or reframing of the situation I’m in where I can make this work for me? Assuming I’m not being you know, legally harassed, or something else is horrible going on.

Because it’s often true that you can reframe your reason for going to work. And it’s, it’s a pretty modern idea that work is going to be meaningful and purposeful, and I’m going to find my joy at work. Remember the book is called Designing Your Life, and it’s about the joyful life with a job in it.

But, for my parents generation and my grandparents generation, they didn’t work for meaning, they worked for money. And they got their meaning from their community, from their families, communities, churches, whatever. So this notion that the job has to provide everything is a little bit of a modern idea, and it doesn’t have to be that way.

There’s money making and meaning making, and you can do, you can just go to work to make money, and that’s a noble cause. If you’re, putting food on the table and you’re sending the kids to college, that’s great. That’s a reframe that makes that worth it and you get meaning and purpose and stuff from coaching the little league team or the girls soccer team or, running a Bible study at your church, whatever it is, typically meaning comes through your community, family and community, not through work.

So gravity problems are problems you can’t change. And the way you fix the gravity problems, you accept, this is not changeable and then you pick another problem that is actionable and you reframe and problem solve on that. And that’s how you do it. And it, a lot of times it just comes back to questioning assumptions.

Why did I expect my job to be meaningful? I’m in the accounting department. I process transactions. Now, I might be the kind of person who just loves getting all the things in the right box and checking all the right, making sure that everything is lined up perfectly and that the things balance at the end of the week and if that’s the, that’s where you get your joy, awesome, but it might also just be, it’s a good job and it pays pretty well and it gives me enough time, to coach the little league team.

 That’s good enough. 

Lauren: Thank you for that. I think to what I found is sometimes there are real limits like it’s just impossible if not really hard to change my situation and other times they’re more artificial limits. And so others in my class at law school who didn’t take the design thinking course might say, :well, I just went to law school for three years I don’t know what else I could do, or I could never do this thing that I don’t have,

a lot of experience with so at the time I might have said, Oh, well, maybe not corporate law, but maybe employment law or environmental. Maybe it’s a little bit better. But the truth is, I don’t think law ever would have been that fulfilling for me, but I love coaching, right? So it feels so purposeful. It feels like appalling.

Um, or another, um, client who I worked with was an accountant in South Africa, really unhappy. And now he’s the global head of creator marketing at TikTok and a motivational speaker and so happy. And it was like, it’s a huge jump, right from, from where he was. So often I think there is this vast potential that we could live into if we were to just remove the artificial limits.

And so I’d be curious your response to that and this concept of we can have multiple lives, right? There’s my life as an optimized lawyer. There’s my life as a coach. Can you share a little bit about this exercise that you share with people on thinking much broader in the multiple lives we could have?
 

Bill: A belief system attached to every question like are you living your best life? Well, that assumes that one you could compare all the possible lives That you might have and that one is the best. I don’t know. What’s my, I’ve been an educator, I’ve been a designer, I’ve been a toy designer, I’ve been a computer, which one am I comparing to what, what’s best, there is no such thing as best, and there’s always more than one of you in there, there’s more, I mean, just for Chuck, let’s talk about life with a job in it, not just what do I do for a living, that’s a very small part of who you are as a three dimensional, emotional, wonderful person in the world,, and the pivots you’ve talked about, going from accountant to TikTok, global mentor.

It’s like those are nice to talk about because they’re exciting sort of success stories, but a lot of people that I work with in coach are like, I’m just going to make a couple of small changes. I just want to, I want to rebalance my time with my family. I want to re rethink about what I put my energy against and how much time have I, am I wasting, on gravity problems that it’s not going to solve

they’re not going to change anyway. And I do, so we, the big assignment in the class and the book and stuff is to think about your life in more than one way. Designers always come up with more than one solution before they start, start narrowing things down. And most people just have one idea.

I’m going to be a lawyer. I can’t be a lawyer. I don’t know what I’m going to be. I don’t have, I don’t have another, I don’t have a plan B.  I want you to have a plan B, a plan C, a plan D, plan E. Because, first of all, even if you love being a lawyer, there’s this little thing called AI coming.

Going to be a lot fewer lawyers in the future and fewer accountants in the future. So you might not even have a choice to change. And wouldn’t you like to have practiced a really resilient strategy called design so that when things change, you can change with them you’re riding on top of the wave, not being buried by it.

So whether you’re happy or unhappy, change is coming. And you want to have some ideas and tools to deal with that. And don’t, the other thing is I’m a pretty, I’m an optimist. Designers are inherently optimistic. We always think the next design is going to be better than the last one.

We really liked the last one. It was really good. And then we have some new ideas and we make it better. So don’t you hope that there’s something in the future that’s going to be even cooler than what you’re doing today, but it hasn’t been invented yet. When I came out of school, nobody was talking about

of design thinking. It wasn’t a thing yet. When I, when I’ve learned all these different tools for designing and things, and everything has changed all the time, and now there’s new stuff changing as it goes. And if I look at what, if I look at my workflows, and I look at the things that I do nowadays, it’s nothing like what I used to do.

But it’s so much more interesting. So, yes, we think the best is the enemy of all the possible better lives you could have. There’s always three lives in you at any one time. Three things you could be doing today. And this idea of constraints and limits um, that are artificial, when you look at the psychology, of change or behavior change and how things work, it’s all fear driven. There are many, many opportunities for you to do something other than what you’re doing. But you don’t see them, one, because you don’t go looking, and you don’t because it’s scary to change. And people they will hold on to a situation, even a bad situation, longer than they should, simply for the fear of changing.

This is bad, but I don’t, but the new thing is unknown. And so that’s even scarier than the bad thing I’ve got, right? And we all know we’ve all had that experience of not changing, even though we knew we should have, because it was scary to try something new. And so that gets us to the whole, well, designers try new stuff all the time, but they don’t quit their job and, apply for a role at TikTok as an accountant, they prototype. The way we invent new products as we make little tiny experiments called prototypes. And we just keep doing that. I have a question for you, Lauren, before you went to law school, how many lawyers did you talk to about what it was like to be a lawyer? Zero. Zero. I see this all the time.

It’s like, why are you putting yourself through this rigorous, incredibly difficult and expensive training, and you’ve never actually talked to somebody who does that job? And that’s a prototype. Prototype conversation or information interview is a little blast to the future. If Lauren’s, undergrad had talked to five lawyers and come back and said, they have the most interesting jobs.

I can’t wait to be one of them. Then you would have made it through the law school and you’d be super happy. But my guess is you would have talked to those folks and said, huh, none of this is resonating. I mean, nothing is ringing in me that says this is my path. And nobody does it.

They go get an MBA, and they don’t want to be, an MBA. They go get a finance degree. They don’t want to do finance. They get a law degree. They don’t want to do law. They end up in, investment banking. They don’t want to be a banker, but nobody, nobody, has the, , the practice of prototyping.

So one of the things we teach is there’s more than one of you, and then there’s three, and you can prototype anything and prototype experiences, prototype conversations. , a little mini, mini experiments with anything you want to try and you learn so much because humans, , are natural pattern matching storytelling people.

And so when you get other people to tell you their story, , you can almost tell whether it’s a fit or not. William Gibson, the science fiction writer has a phrase the future is already here. It’s just unevenly distributed. So there’s someone in the world doing the thing you think you want to do.

And if you talk to them, it would be like time travel, be like, Oh, that’ll be me in five years. Do I want to be like that guy? I was talking to the chief learning officer for Deloitte. One of their problems is big consulting firm, started as a junior analyst and move up to partner. One of the big problems is people, they hire three or 4, 000 super smart kids right out of college and about three or four years they’ll quit.

And she was asking the high performers like on the partner track. And he was asking him, why are you quitting? Cause I talked to the partner. And I saw how the partner’s lifestyle is, and I don’t want to be a partner. Their lifestyle sucks. They make a lot of money, but they’re miserable. And I’ve talked to lots of them, and they’re all miserable.

So why would I want to stay in the system where the reward is misery? And it’s so funny. Most of the people I know who are really, really stuck are actually have plenty of resources, plenty of money, plenty of education, plenty of things they could do. But they’re afraid to try. So prototyping is the way to break down the fear into tiny little steps so it’s not so scary.

Lauren: I love that. To your point, that’s exactly what I did after the design thinking class for coaching. So I took a three day coaching class. I talked to many people that were doing coaching, someone that was in house and learning and development, someone that had their own private practice. Like I really got a lay of the land and started doing small trials.

Bill: So I mean, cause maybe coaching wasn’t your thing, who knows, maybe, dealing with people who can’t make decisions would be frustrating for you. But , you built your, so we in design, we say we build our way forward. We built to think we don’t build something to prove it works.

We try things. We prototype things. We build things to explore the space and you were doing that when you were talking to people who had different kinds of coaching roles, different kinds of, in big corporations and solo practitioners, all practitioners are coaches and entrepreneurs.

In addition, I know a bunch of people take our coaching certificate, but they don’t have a coaching business because they just want to help people, but they don’t. Know how to market, sell, you build communities, blah, blah, blah. And, and so , I’m always curious, like how, when you’re a sole proprietor, you are by definition an entrepreneur.

And if you don’t want to do that part, it’s not going to be very successful. 

Todd: Go a little bit deeper on the, the rapid prototyping piece, because I think we’re in the nut of it here, I want to see what tools or practices that you recommend, because I think a lot of people deal with bias to action, right?

So they know what you’re saying. Is true, but something is holding the back. It could be the idea of why I got to get it perfect, or, it could be a limitation around. Well, I actually just don’t I don’t have the time to think about plan B. C. D. E. Like you said before, right? That’s your recommendation is to be thinking this way.

 And, we believe here that movement is always more important than perfection or movement is more important than inaction. So share more about this specifically, right? When someone comes to you with the idea of like, okay, I get what you’re saying is good, but I have a problem taking that leap into action.

The first action is pre action, right? Which is actually taking the step to rapid prototype. Do you have them carve out time and space per week per day? Like how do you go about, having someone integrate, this new mindset? 

Bill: Well, in two different worlds, they do it two different ways when I’m teaching is I am actually teaching the seniors and juniors, designing your life this quarter and I say, hey, biased action and I really mean it.

Here’s your assignment. You will go talk to four people, one of this one of this one of this and it’s homework and you have to do it. If you don’t do it. You got a bad grade. And so for them, it’s like , the way to overcome fear is they fear a bad, they fear a bad evaluation more than they fear the actual talk to people.

When I’m talking, when I’m just coaching folks on the outside and stuff, it’s look, nothing’s going to happen until you take a step. And let’s make the steps really, really small, set the bar really low. All right, the information you’re viewing, and you’re not sure who you want to talk to, but I need you to talk to somebody this week.

So here’s what you’re going to do. You’re going to call your mom or your dad or your uncle or somebody, and you’re going to say, and let’s say you’re curious about maybe moving from whatever you’re doing to a coaching practice, like you did. So you’re going to, you’re going to call somebody you are comfortable talking to and say, do you know anybody?

Who does coaching or knows anybody in the coaching world. And if your uncle doesn’t know somebody and your dad doesn’t know somebody and your mom doesn’t know somebody, ask your mom for her freshman college roommate’s number and call her. But somebody in , in a very, very small network, I’ll get on LinkedIn and send out three, direct messages to people in the coaching world, but you have to make the steps small enough that they’re going to overcome fear. The, the, when I’m working with entrepreneurs is get your business plan out, let’s get to Sand Hill Road, it’s not perfect yet. It’s never going to be perfect, it doesn’t matter, by the time you come back from your first two or three venture meetings, you’re going to know more than you know now. Yeah. So just go out and, it’s like, it’s the first waffle. You’re not going to get any money from the first guy you talk to anyway, so it doesn’t matter.

Let’s go talk to somebody up in Sand Hill Road, bet the plan, you’ll get five or six or seven major objections, and then we’ll know what we need to do next. But they don’t do it because they’re afraid, and they claim that the reason they’re not doing it is because they have to make it perfect first. But that’s just the fear response.

Like, I’m afraid of rejection. I’m afraid of, trying. And so you gotta be, you gotta be kind to people. It is scary. And it’s certainly scary to move sometimes, so why do people, if you look at the psychology of behavior change, right? So, , you should get healthy, you should eat better, , you should exercise and all that and you have knowledge and you even bought a bunch of books in January just after, New Year’s to get you going and you didn’t do anything.

Then you have a heart attack and then you recover. And then you actually now started doing all the things you knew you were supposed to do. Why did it take the heart attack or the, checking with the doctor, hey, you’re pre diabetic, if you don’t turn this around, this is a very, you’re going down a very dark path.

, I think it takes a, that kind of crisis can overcome the fear. But what we want to do with when we work with people is to avoid the crisis and to just take small steps. Typically, the easiest thing to do is to go have a small experience. Go shadow somebody who’s doing what you’re thinking of doing for half a day.

Go, I had a woman who was in her 40s, wanted to go back to college. You didn’t think it would work because, the millennial, the millennials and Gen Zs don’t like people in their 50s. I said, get down to the Stanford bookstore, get, buy a t shirt that says Stanford, the big, the cardinal one with the big white letters.

You can walk into any classroom on the campus. I sent her to two classes. She walked in, she sat down, she came back, she said, it was awesome. I loved it. I loved being in that environment. And I didn’t know if it would fit, but it felt like a good fit. And the students were really kind. And I set up some prototype conversations with the students about what they’re interested in.

And somebody showed me this new app called Fizz. And now I’m on Fizz. And, but, I think once, once you inevitably, once somebody comes back from having done the assignment, they’ll say, I didn’t think anybody would talk to me, but I had a really good conversation with three people, or I didn’t think, I didn’t want to take the time.

I asked for 30 minutes and they gave me an hour. So the fear is lowered in, small incremental steps by taking really tiny, tiny, running tiny, tiny prototypes, but once it gets going, the kinds of conversations you’re having, the kind of experiences you have really lead to their own sort of energetic response.

You want to have more 

Lauren: To your point that again, that’s exactly what I did. And so when I was feeling into do I like teaching and coaching? I had six friends in my small apartment in San Francisco at the time, and I let a work two hour workshop. What does this feel like? Are people getting value, right?

So it doesn’t even have to be, I think, finding people out in the world. Can you prototype even with friends or family? What’s the lightest touch? Shadow someone for a day, to your point. What’s a really light touch to be moving in the right direction, but in a way that feels somewhat within your comfort 

zone? 

Bill: We talk about the process of, starting with accept and, then empathy for what do you need, what does the world need, just because you want to do something doesn’t mean the world cares. And then, the ideation prototype and testing. But the bigger thing is the mindsets of a designer.

A designer is inherently curious and curiosity is a human. It’s just, it’s one of these strange human traits where humans are curious for no good reason. There’s no, there’s a benefit to curiosity in terms of learning. But The, orientation to be a curious person is what psychologists call an intrinsic motivation.

You can do it just for the joy of being curious. Once you get curious and you start talking to people, and then you start trying, start prototyping stuff, and then you tell your story, which leads to more people going, how are you on this journey? How interesting. Hey, I know a person you should talk to.

And then you get curious about that and you keep doing. So it’s get curious, get curious, talk to people, try stuff, tell your story. It’s a virtuous cycle and just those mindsets of I’m curious. I’m in a prototype mindset. I’m in a talking to people mindset the answer is out in the world, radical collaboration and storytelling on my journey, not to brag about myself, but to just engage the world

and stuff so when people hear your story and they go, I want to help because people are generally kind. 

Lauren: It’s true. I think of it as, giving voice and casting votes. So the vote was okay, six people in my apartment. I’m just moving in that direction. I’m trying different things. Stanford was a 10 week part time position when I started there, but also I found out about it because I just started telling people I want to do coaching.

I’m exploring coaching. What is this like? And then a friend. Said, Oh, I just received an email. Stanford’s looking for a speaking coach. And so I share that just to, if you’re playing with something, if you can tell a lot of people and you start planting seeds, putting it out there, trying different things, that eventually starts to take on a life of its own as 

Bill: you, it’s the opposite of being stuck.

Or sitting on your couch worrying or waiting till you get the perfect ask before you pick up the phone and try to get an information interview. Because once you get started, the momentum of, curiosity kind of is the antidote. For me, curiosity is the antidote to fear. I was a very shy kid. I wasn’t, I’m not particularly an outgoing person, , in, in my own, in my own life and my own persona.

I mean, if you wind me up and put me in front of a TED audience, I can talk, , but I’d prefer to just stay home and read books. But when I get curious about something, I go on and start talking to people. You’re absolutely right. And then those people say, did you know about this thing at Stanford?

Did you know about this other thing? Because the world’s so interconnected now that all you have to do is put the intention out there. And then stuff starts lining up, in a way. And it’s just as, it’s just as valuable or even more valuable to try something and go, that was horrible. I had no idea that’s what a venture capitalist does all day.

That was the most boring day I’ve ever spent. And I asked him, are a lot of your days like this? And he said, yeah, they’re all like this. And I was like, great, I’m out of here. That kind of learning can save you. Three years of law school. It’s a small sample, but your gut tells you, boy, if I talk to three or four more people and they all have the same worldview framing of how the thing goes, it’s just not a fit for me.

Lauren: Yeah, to add to that, just to say, like there are no mistakes. So like you said, you are where you are. So only because I was in law school, did I discover the design school and design thinking, which led me on a path. So rather than thinking of, I shouldn’t have, or it’s wrong, it was a mistake. If you just start from where you are and like Steve jobs, you can’t connect the dots looking forward, only looking back. I think it’s important for people to know how everything can come together and you just create from where you 

Bill: are. I finished law school and I got a job at a law firm and I passed the bar. So I put all this time in, I guess I keep going.

It’s like, no, there’s this idea called sunk cost in accounting like that. That’s a sunk cost. You learned a lot. That’s awesome. But it doesn’t have to be your career. That’s a different, that’s a different decision. 

Todd: Yeah, but I want to ask you, a question about, very clearly, the first part of this process is to be self aware and accept your situation as is, and then it’s to start taking action, and then those actions will then lead to other things that right now are unexpected, but with the quality of curiosity, this will drive you into different directions that are often surprising.

And Lauren is just a perfect example of this, which is why we keep talking about her story, and But I also think it’s helpful to, hear how you share with people who come with some of the common obstacles, right? And so the ones that I would imagine would be number one, it’s just too late for me to implement this, right?

I’m sure you get that often, or I’m afraid of making the wrong choice. So how would you respond to those two obstacles that people come where they’re thinking, yeah, this is all great, but just too late for me to go ahead and do that, or I’m just scared to make the wrong choice. What do you say to those folks?

Bill: Well, it’s this type of it’s too late problem, right? All right, it’s too late. You’re right. So do whatever you’re doing and retire at 62 Life expectancy in the U. S. says you’re going to have another 20 to 25 years particularly if you’re, you know in your 20s or 30s now, you will live to a healthy 100 So you’re going to have another 30 years after you retire to do the next thing.

 That’s a whole nother career, right? So it’s never too late. It’s just like what do you want to do right now? Because, if you’re 30 and you pivot, you’ve got 20 years in the next thing. If you’re 50 and you pivot, you’ve got, 10 years in the next thing. And then when you retire, you’ve got 10 or 20 years in the next thing.

 You’re always going to be reinventing. And it’s never too late to start the process. Dave Evans has a sister who got her PhD in her 60s. Because she was deeply curious about a subject and wanted to study it. So, the bigger one is like, it’s not that so much that it’s too late.

I’ve got the house, the mortgage, the three kids and I’m doing this thing and I don’t like it, but I can’t just stop. You’re absolutely right. That’s a gravity problem. You need to keep making the same salary all the time while you’re transitioning to something different. Or magically somebody shows up and offers you the same salary in a completely different job that you’re not qualified for,

probably not going to happen. So that’s when you create the three lives plan. You do the one, how am I going to, how am I going to do this? By the way, I think the modern thinking on, if you’re 20 somethings in, in your audience. The modern thinking on careers is it’s going to be a portfolio anyway.

Something like 70 percent of Gen Zs have a side hustle. Something they’re doing maybe for fun, maybe for some money, extra money, whatever. But they all have something else they’re doing. We used to call them hobbies. Now they’re calling them hustles. But it’s all, it’s, turning that into your day job.

Might take a year. Might take longer. But, it’s just a matter of getting unstuck. I don’t know if you know this guy, Robert Parker, the guy who invented, the wine rating system. This is a 90 point wine. This is a 95 point wine. Robert Parker, very famous, started a thing called the Wine Spectator.

He was a lawyer in San Francisco. Who loved wine, and he loved it so much that he and his wife, whenever they went on vacation, would always go to France and go to different wineries, Bordeaux and other parts of France, and then he would go to Australia, and then he would go up to Napa, but he was a lawyer.

He started a newsletter because he was so passionate about this. This is back in the, 70s when newsletters, Or things you mailed, you licked a stamp and mailed them. He started the newsletter and he had to deal with his wife. He says, when I can make as much selling my newsletter as I’m making as a lawyer, I get to quit lawyering, right?

She said, yep, but you got to keep making enough money, because we got the kids in the house and blah, blah, blah. He eventually hit that point. The newsletter became incredibly famous, started the Wine Spectator. I think sold it to one of the big winemaking companies for, 150 million for his subscriber list and literally invented the modern wine industry with, with numerical, evaluation and stuff.

So, he had a side hustle. I think it took him seven years to get the newsletter to the point where he could quit his job. But, it’s just, it adopting the mindset of curiosity, radical collaboration, bias to action, getting out out in the world to test your ideas, your thoughts, your gut feelings, your whatever, it’s so empowering.

And once you’re unstuck permanently. Because as soon as you hit another roadblock, you just apply the same principles and get unstuck again. 

Lauren: One of my favorite stories is that Julia Childs was in her 40s when she first started. Exploring cooking. Her first cookbook, I think she was 48 or 49.

The TV show wasn’t until 50. And she’s so famous, right? Cover of Time magazine. So really any age you 

Bill: can. And she had almost no training. I think she went to one class when she 

was living in Paris or something. And she was almost entirely self taught. No, there’s also, I mean, there’s all sorts of, stories, second career stories, whatever, whatever stories where, we find something stable in our first instance of ourselves as a professional.

And then we find another thing that’s even more interesting. I never thought I’d be a full time academic. I worked and, worked in product development my whole life. So, and I never thought I would write a book. I was never on any of my lists, but once you start living into this possible future,

my experience is that it’s a much more, it’s a much richer set of things because when you open up your curiosity, you don’t just see what’s right in front of you. You see what’s all around you and there’s opportunities everywhere. 

Todd: And to follow up on that, you talk in your book about luck.

, and that lucky people have a larger periphery, so a lot of us can be cynical or judgmental. The idea that there are lucky people out there, but you’ve addressed it head on. Talk a little bit about that, who are lucky people? 

Bill: I forget the psychologist name, but he’s a psychologist that studies luck and we can probably find it and put it in, Subsequent, chat when you send this out, but, he said he’s like, and the experiment was the experiment with the newspapers where he’s asking people to, coming to the lab, count the number of, headlines or the number of photographs in the newspaper.

 It’s a big thick thing, like the front section of the Sunday New York Times. And if you get the right, and when you get the right number, give us, give the graduate student the number and collect a hundred dollars. And the people who, but before this, he has people rate themselves on a luck scale. One, two, three.

I don’t know why. I’m not very lucky. Bad things always happen to me. Eight, nine, ten. I don’t know why. I’m really lucky. Good things always happen to me. And what happened is, it was, of course, if you’ve ever done a psych experiment, whatever they tell you the experiment is, that’s not the experiment.

There’s always a trick. And the trick in this case was, it looked like, 30 pages from the front section of the Sunday New York Times, but it was a fake newspaper. And buried inside the newspaper, inside little stories, was a little snippet of text that said, Hey. Hey, if you read this, the experiment’s over, collect an extra 100.

And the data set was people who rated themselves as unlucky at the bottom end of the scale, completed the task, got the right number, 37 headlines, 42, whatever it was, and collected their 100 and were very pleased. And the people who rated themselves as lucky something like 70 or 80 percent of the time found that little piece of text buried inside this, giant piece of newspaper and when, Hey, I’m done, I get the extra hundred.

. And so his conclusion was it wasn’t that people were lucky or unlucky, it’s just that the people who were more curious, who had their peripheral vision open, who were not just counting the things they were told to count, but were reading this interesting, look at this interesting newspaper, there’s an article here about, kids in STEM education.

They found the thing because they were paying attention, and they weren’t just doing the task that was assigned to them. And I don’t know, I’ve got friends who like, I got a friend who’s a, an artist. And when she stands in line, by the time she’s standing in line at Starbucks, so there’s four people in line, by the time she gets to the front of the line, she has three invitations to dinner, she knows four, four people’s names and numbers, and she knows that their kid is going to, going off to Harvard next, next, next semester, and she has a friend at Harvard that she wants to introduce him to. She’s constantly out, out in the periphery. Now, she’s always late and doesn’t get stuff done because she’s an artist, but she’s wonderful with this being lucky thing because she’s just so engaged in the whole three dimensional tapestry of the world, and other people, they’re just standing in line, they get their carts, their Starbucks thing, and they don’t even notice, that the barista’s name is Debbie or something, right?

So it’s just a matter of opening up your peripheral vision, opening up your curiosity, and noticing all the amazing stuff that’s going on around you, because that’s how we see more than just what we’re looking for, right? . I

Lauren: love that. So often we get on autopilot. It’s the same routine 

Bill: all the time.

But, but, 

Lauren: But even you’re like, Oh, that feels interesting. What if I explore that? Oh, what if I did that? What if I ran a small experiment, just asking what if, and seeing things and trying things like a child, right? Children are more like that.

Bill: It’s incredibly like a child. I have two young grandkids now and one’s about almost three and, just playing with Connor and watching him. look around the world because everything’s brand new to him. He’s only been around for, a couple of months, a couple of months, really. And watching that natural curiosity, we all had as children. And then school beat us out, beat it out of us and work beat it out of us and stuff. So if we can get back to some level of curiosity and wonder, that alone will change the outcome of anything.

And remember, it’s life with a good job in it. You can’t build from the job out in my experience. And life has all sorts of other things in it, relationships, community, partners, things that are not connected to the thing that you do from nine to five. So don’t lose sight of that because that’s also where wonder and curiosity can lead you to some really interesting new things.

Todd: Actually, I want to ask you about that, right? So we’ve been talking a lot about career, but can you apply design thinking to relationships and in these other areas? Do you help people do that in this process? 
 

Bill: We didn’t in the first book at all. In fact, we just because we were probably David and I was just working with students,

we hadn’t thought about it. But we were at a book signing in Chicago. We’re in Chicago and they were doing the thing and we did a talk and we’re signing books and this young couple came up to us, and said, thank you so much for writing this book. It saved our marriage. And I went, whoa, whoa, wait a minute.

Tell me more. Because we don’t even talk about marriage, partners, anything. And the book said, well, we both have careers. And it used to be, my career versus your career. It’s my turn or your turn or my turn or your turn. We started doing Odyssey plans together, our Odysseys together. And we realized when we made planning our future a creative experience instead of a negotiation experience, stuff started showing up and then we could both have what we wanted.

In fact, we can have more than we had imagined in the beginning because we started talking about what we really needed and what would make us feel fulfilled and what would bring us, joy together instead of just this competition. So thank you so much. And I said, Dave, we got to put that in the next book.

So we are going to put it in the next book about how you create, because you’re never designing your life all by yourself. You’re designing your life with partners, with family, with community. And I think the opportunity there to be generative rather than negotiating and to be creative, will open up a, a bunch of different kinds of conversations between couples, partners, friends, families, that might unstuck or unblock some things there.

And we’re really excited about that possibility because it works. I’ve seen it work when I do brainstorming, when I do mind mapping, when I do work with people on teams, um, being able to design together is even more, more, uh, more, more generative, more exciting, more energetic than designing alone.
 

Mmmh, 

Lauren: I love that two

two comments to that one. You mentioned odyssey planning, which is this idea of like, what’s our optimized career? What’s an alternative career? And then what’s a wild card, really exciting career. So you’re just imagining other worlds and possibilities. My friend did that with his wife where he really wanted to have kids and she wasn’t sure.

And there was this negotiation and they were always arguing and back and forth. And so then he started to explore. Well, he was just so convinced having kids was the right life, but then he started to explore what did a really amazing life without kids look like? Like, what would that be? And he was curious to your point.

And he’s like, Oh, well, that could be really good too. And then we could do this and have all these other possibilities and they did end up having a child, but it just changed the conversation when he was open to 

Bill: other. 

Yeah, it’s just that’s 

that’s a great, that’s a great story. Let me know how to interview those guys for the next book, but, um. The other thing we’ve added to that now is storytelling where you say, okay, now, imagine. It’s 3 years from now, and you’re in that wild card out of supply and you are doing that thing that you just imagine doing it. And you run into somebody in line at the coffee shop and they say, Hey. Todd, how’s it going man?

And you go great And they say what are you doing? And then you tell them and you write the story of what you would tell them Yeah, I did. I did quit my job as an investment banker and now I’m a part time scuba dive instructor, and I’m a life coach, and I’m also working at a community college with kids, that are first gen, to go to get any higher education. And my life is full of this tapestry of amazing experiences, and here’s what I do every day.

So we have them write this story, which allows you to think about what would that future really feel like and sound like if I were narrating it back to somebody. And that’s been really powerful. Sometimes people, and like, we used it in class and somebody, a student came up to me and she said, I took, I always wanted to go to, to medical school.

I’ve been wanting to go to medical school since I was 10 years old. But I’ve been having some doubts about it. And so I decided to write up the story about it. I didn’t go to medical school. I did this other thing, this other option. And so then I was telling, I was, and I was reading my story to the other students, and they were going, wow, that’s really awesome.

And I realized, I don’t want to go to medical school. That was something my, my seven year old wanted. It’s not what I want. And I was able to let go of it just through the act of just speaking out loud a different truth. I think it’s so powerful. So much about storytelling, because we’re wired for narratives as humans.

So when we invent a story. We’re inclined to believe it, including the story that I told myself when I was seven, and now my 22 year old is kind of acting out the story even though it no longer fits. 

Lauren: Giving voice to playing with trying on 

Bill: literally giving voice. So you have to read it out loud. 

Todd: And I love the idea of like the feeling of it.

Right. It’s like when you can associate the emotion with this future, we did a practice for years where we had people write their own eulogy, but we gave them permission to actually like, think about, like what is said about them when they’re no longer here from the concept of the ideal set of circumstances, relationships, career, money, all that happened, but you know, and, and just understand what the feeling is just as an exercise, you know, and a tool.

So I love that you you’re doing that work and bringing that here. I think. It’s really, really powerful, and we’re so grateful for your time, and we’re going to ask one or two more questions, and then for those of you that are in the live audience, we’re going to open it up for some questions. If you have anything for Bill, please let me know, and we’ll, you can raise your hand, and I’ll call on you, and that’s really generous, Bill, of you to do that.

Um, I actually just want to switch gears for something, uh, to ask you a question about something that you said before. Around the future of professions and careers, right? You indicated I know some of your work is actually looking at that. Like, where is this going? You said we may not have a choice but to switch jobs and careers.

In your research, you know, you mentioned CPAs, you mentioned lawyers, like, like, what, what areas are going to be the most impacted? And how do we most prepare for that? 
 

Bill: I’m a designer, not a futurist, but I read a lot of stuff you know the McKinsey study on ai. There’s a, a big Forester study on ai.

There’s a couple other things that have come out and lots of people are researching, what’s gonna change in the world as we, enter this, it’s just called the next stage of automating, work tasks. And, the way I, without going into all the research, the way I think about it is, there’s kind of two things humans do.

They do a lot of transactional thinking. How do I get from here to there? How do I pay the bills today? How do I insert all my emails? It’s just transactions. Something, data comes in, data goes out, and we’re really good at managing transactions. And then there’s another kind of thinking, which is creative thinking.

I’m trying to come up with something I’ve never thought of before. I’m trying to come up with a new idea. I’m trying to come up with a new way to think about a problem. I’m trying to write something in a way that really evokes, like you said, emotion. Jobs that are primarily transactional are the easiest jobs to automate.

I remember when the first, I’m older than you guys, I remember when the first spreadsheet came out. And everybody said, what do we do with all those people who calculate numbers? It’s I’ll find something else to do because spreadsheets are faster. And, you don’t have to just change one number and the whole thing calculates itself.

So that’s a form of automation. So is AI. So is, all this other stuff that’s coming out. But AI is really good at transactions. So if I’m a banker and I’m charging you 2 percent to invest your money to get you a good rate of return on your . , I’m in, I’m in trouble if, if you can just have an AI do the same thing, get better returns and cost you nothing.

Right? So if I’m in a transactional job, I’m moving money around and taking a piece of it off the top. I’m, I’m a lawyer. I’m rewriting that same contract dozens and dozens of times for different situations. That’s going to disappear if I’m, uh, if I’m a, if I’m an engineer and I’m writing code, I’ve been telling my students for 10 years, don’t be a CS major that for that profession, you think it’s great because you can get a nice starting salary, but I’ll tell you in 10 years, we’re going to have half as many coders because what’s the easiest language for a large language model to emulate?

Oh, a language with 800 words and no exceptions called Java, a language with 1500 words and no exceptions called C++ I mean, You know, so, so transactional stuff is going to be, uh, you know, done more effectively and more efficiently with these new forms of automations, like, like large language models.

And at the same time, that, that, of course, what then, what will people do? They’ll spend more time on coming up with, the right question, the good question. They’ll be spending more time in the creative side of things, which is still un, un, um, I think fundamentally would be un automatable at all. Because these models are only trained on stuff that’s already happened.

They’re not trained on stuff that hasn’t been invented yet. So I think, you know, if you’re looking at professions, think, think about in your profession, how much of your time is spent on creating new, new frameworks, new thoughts, new ideas, new text, new something, and how much of your time is spent just transacting, you know, moving data from one side of the thing to another through some little transform function, like I’m the accountant, I’m the analyst, I’m the something, I do this thing, and then the data changes, and I hand it to somebody, and that’s what I get paid for.

If that’s what you’re doing, I think that will probably those kinds of jobs will change radically, and because they’ll, it’ll be more efficient to do them with these automation programs like, like, uh, chat, there’ll be fewer people doing the grunt work, so to speak, and more people doing the creative work, which I think will be fine.

The economy will just adjust and we’ll have more creatives. 

Todd: Yeah, agreed. I mean, I just love hearing, hearing from you because you’re kind of in it with so many people helping them with these types of transitions. And, um, no, I just want to honor that. 

Bill: I’m just, it confounds the parents of the students, like, because students come to office and say, what should I major in?

I don’t know. What do you want? I don’t tell anybody what they should do. What do you, what are you interested in? It’s like, well, if we’re talking about the choice between being an English major in liberal arts or computer science major, I choose English. I go, why? Because that will be a job in the future.

Computer science, eh, maybe not. But the people who will have real jobs that are interesting in the future will have a really good liberal arts degree. 

Lauren: One thing I think is interesting is you keep coming back to like, how does it feel?

And I think that’s something not in our culture so much. Like, what do you think you should do? What’s the right thing? To do versus what gives you energy, right? What’s the feeling when you think about this thing or try this thing? Because I found often when something feels really good, you kind of go above and beyond.

You have extra energy to do it. You’re kind of more successful because you have the, the drive. 

Bill: Yeah, exactly. Um, it’s, it’s, yeah. Um, and, and you mentioned energy. Energy is a proxy for attention, for engagement, for meaning, you know, what you pay attention to what you spend energy on is what is, is what, um, engages you and gives your life meaning.

So that’s, that’s a great, it’s a great way of looking at it. And, you know, a lot of students that come to the design program when I’m advising students, um, they’re kind of from the engineering side of the house of some programs in the engineering school. And, um, they’re not very good at identifying emotions.

Uh, and just as a stereotype, they are, you know, they’re kind of analytic. They got here because they were really good at math and numbers. And so when I say, how does it feel? They go, I don’t know. So, well, go, go home this week and you’re only allowed to ask yourself the question, how am I feeling right now?

Check, checking in with your body, you know, is there tension somewhere in your body? Is there tension somewhere in your head? Where in your body do you feel these, these, you know, these feelings? Is there a sense of this is right, this is wrong. You’ve got to tune into this stuff. And it takes some, it takes some practice because not everybody.

Um, not everybody is comfortable in their exercising their emotional intelligence. 

Todd: Beautiful. Well, I gotta say, um, we’re kind of at time with the official part of this interview, and I know we’re going to stick around and see if anyone has any questions for you in our live audience here, um, but I just want to share that what you’re sharing is so intuitively right, but also that you’re backing this with so much research, right?

And so, so many people running through your program, uh, that I think it’s promising, you know, what you’re offering to me is hope, right? That we can do better. We could think about our lives differently. And there’s real tools out there that, uh, Product designers have known for so long that really understand that, that we can now apply to bigger thinking our lives, our career, our purpose, right?

Unlocking our potentials. And a lot of what you’re saying with understanding where we’re at and then experimenting and then allowing that flow to open up these new pathways with curiosity. As one of your main values is just really, really powerful and just really well said. I know people listening here live have gotten a tremendous value from this, and we just want to all thank you so much for being with us here today.

And Lauren, what about you? Want to give a little appreciation to Bill?

Lauren: Of course. I mean, it’s such a gift. I make a walking testament to this work, and I share it with others that I work with on a daily basis. So yeah, just very grateful to be here with you and having you share it with others. 

Bill: Thanks for all the good questions.

You mentioned hope, Todd, when we do assessments of the class, we, one of the two things that come back most frequently are I don’t feel stuck anymore, and I feel hopeful. 
 
 

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