Stanford’s Life Design Expert: Why Your Dream Job Might Make You Miserable | Dave Evans
52m 18s
The transcription presents a life design philosophy rooted in design thinking and personal exploration, emphasizing that meaningful life choices come not from a single "right" path but from curiosity, empathy, and experimentation. The core process—called the Odyssey Plan—guides individuals through three stages: mapping their current life, imagining alternative paths, and exploring a wild, risk-taking idea. Central to this is prototyping, where people test concepts in low-cost, real-world ways (like offering to work at a deli or join a podcast) to learn rather than decide. The narrative highlights that success isn’t guaranteed, and even well-intentioned decisions can fail—yet failure is part of growth. Personal stories, including one about a father leaving a high-achieving career to become a present father, illustrate how prioritizing relationships over status leads to deeper fulfillment. The message is clear: life is not about achieving a fixed outcome, but about embracing uncertainty, learning through action, and living authentically. This approach applies beyond careers to relationships and grief, where acceptance and present-moment awareness foster growth. Ultimately, the goal is not to find a perfect solution, but to live with curiosity, resilience, and connection.
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Rep number 10004.
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I've not met many 80-hour people
who in fact are doing it for their family.
They're mostly doing it for themselves.
She quit her job, she mortgaged her house,
she bought this beautiful deli,
and unfortunately it was profoundly successful.
And she immediately found out she hated it.
You can do everything right and it'll still fail.
The correlation between a good decision
and an assured outcome is zero.
There is no best you, right?
There are lots of good yous.
What was the number one thing you learned
from Steve Jobs?
My three-year-old son doesn't have a father.
I was fatherless because my dad killed himself.
Robbie's fatherless because I'm just gone
and even when I'm here, I'm asleep.
Well, asleep looks a lot like dead.
The best year of my marriage
was the year after she died.
Can you explain that?
Thank you so much for being here.
I am so impressed after reading your resume.
I just could not believe all the amazing accomplishments
that you've had in your career.
And as somebody who has started over many times in my life,
I love the fact that you help people
who might be stuck in a place
that they're not truly happy in get unstuck
and find their purpose, their mission, their happiness.
So I know that this episode is gonna help so many people.
So I just wanted to start off by saying
thank you for being here.
Well, thanks for having me.
I love what you're doing here.
And I really like the kind of stuff we're gonna talk about.
And it's all about helping people figure out this thing
about turning into themselves.
And none of us arrived with a manual,
so we've got to figure it out.
And you've created the manual, essentially.
Well, some tips, some tips, yeah.
Yeah, from what I understand,
you've developed a five-step process,
a plan that teaches people how to get to the life
that they want to grow into next.
Can you walk us through what those five steps are?
Well, Dar, it's interesting you talk about the five steps
because we actually have the five-step version
and we have the four-step version.
The five-step version is the steps of design
as taught at Stanford University since 1963.
This thing we now call design thinking was originally called and still technically known as HCD, human-centered design.
And it starts with empathy.
Step one is really understand what's going on.
Then goes to definition, define what you're working on.
We problem find before we problem solve because most of the time stuff doesn't work.
It's because you're working on the wrong thing.
So after you've been empathetic and really understand the situation, then from that, derive the definition of what your objective is, what you're working on.
Then we ideate.
We're well-known in design for being good ideators, having lots and lots of ideas and brainstorming.
The purpose of which is then to move forward by prototyping.
We build our way forward in design.
We don't think our way forward.
We don't analyze our way forward.
We don't prognosticate our way forward.
We build our way forward by trying real things in real time in the real world.
And then finally test our ideas before we actually implement them.
Those are the five simple steps.
A life design approach boils down to the following post-it note.
Get curious.
Talk to people.
Try stuff.
Tell your story.
Four steps.
Get curious.
Talk to people.
Try stuff.
Tell your story.
In the middle two, talk to people and try stuff, are prototyping.
They're going out in the world and trying ideas on about what your life might become.
And that's really it in 10 words.
You can skip the 285 pages of the first book and the 292 pages of the third book, and that post-it note will get you pretty far down the road.
Your background as being part of the founding team or the team that invented.
Did Apple's first mouse?
Yeah, I was the world's first mouse product manager in 1979.
I joined Apple six weeks before the IPO.
The company grew from 800 to 5,000 people in the first year I was there.
So it was pre-Macintosh.
I was on the original Lisa team, which was the technology that generated Macintosh as a second generation.
So early days.
And then you went on from there to found Electronic Arts.
I was one of the co-founding team.
Trip Hawkins founded the team, and then six of us sat around a dinner table one night and said,
okay.
I'm in.
And I was at that table.
And then at the peak of your success, you decide to walk away from it all to prioritize spending more time with your family.
Yep.
And then you join Stanford, where your alma mater, in order to start this life design program.
Yeah.
So, you know, there's so many people that are listening to this, and I know I've been in this place many times in my life.
But for that person that feels stuck in their life, they're miserable, and they're nine to five, their job,
wherever they're going.
They're going to get stuck in their career.
It's taking them.
What is the number one piece of advice to give that person to get unstuck?
It really is that line number one in that simple four-step process I gave you, get curious.
Curiosity is this natural human energy inside of each of us.
And actually, in our second book, we talk a lot about career redesign.
For the stuck person at work, you have four different strategies for redesigning your job on the job.
The best person to give you a better job is you.
You could redefine and reenlist yourself in the same job.
You could remodel the job you're in.
You could reinvent what you're doing.
You could even relocate yourself.
Those get harder and harder to do.
They're bigger and bigger tasks.
But nonetheless, they're all available.
And they all begin with the same thing.
Wait a minute.
What am I curious about?
When we put all our attention on what's not working, all we're doing is fueling our complaint.
So what is working?
What else might be interesting?
So looking around, it's the positive energy in your life and in your situation that's going to give you the raw material of having a new idea you can do something with.
Most people get stuck looking at the wrong side.
That's kind of the equation.
I saw that you have this odyssey method that starts with you look at where your life is today.
You look at an alternative path.
And then you look at some sort of wildcard path, which a lot of us have.
It's almost that big dream as to what my life could look like if I wasn't afraid of risk.
But a lot of us are stuck at this baseline place.
Can you just walk us through practically, right?
If I, let's say today, I'm working as a software engineer or a nurse, and I'm not happy.
I have these ambitions that I want to do something else, but I'm scared because at the end of the day, I've got bills to pay.
There may be this alternative career that seems somewhat safe, like not as big of a leap.
But what I really want to do is actually be an author or start a podcast or pursue my passion in arts.
Walk me through what is the step-by-step process that you would give advice to help that person?
So the whole point of the odyssey plan in the first place, we called it odyssey.
Because one of the names of the young adult age from 18 to 32, when you're becoming a grownup, you know, one author called the odyssey years.
We like that name because we're all on this odyssey, but it's true for all years.
I mean, I work now mostly with the old folks who are taking the gap year between 50 and 70 at Stanford, and they're all in odysseys too.
Because that question, what do I do with the rest of my one wild, wonderful life, never goes away.
And as people try to answer that question, they get stuck because they think there is an answer or is the right answer.
Or the best answer or the truest answer.
I will be happy if.
I will be happy if.
And there's only one way to achieve.
What should I be doing?
And we're going, whoa, whoa, whoa.
Back to empathy.
All of us contain far more aliveness than one lifetime permits you to live out.
There's more than one of you in there.
So how can there be one right answer to you when there's multiple yous?
So when I think about my future, I can't just think about one thing because that's way too small.
I need to hear from at least a couple of me in order to have my best idea.
So the point of the odyssey plan is let's hear from at least three of your partners.
What are your possible futures?
And does that mean having an internal dialogue or how?
Okay, so how do you generate that internal dialogue?
How do I discover that?
The odyssey plan, by the way, unfortunately, we called it a plan in the book.
It's really just the odyssey ideation exercise.
The whole thing is imaginal.
So we say, what might the next five years of your life look like if you stay on the current track and it goes really, really well?
And then just assume, okay, you can't do that anymore.
Dear Dar, I'm sorry, the podcast industry has been completely upset by AI.
We don't need any hosts anymore.
Goodbye.
We're done.
And you're on the street.
Now what do you do?
Okay, what's that other thing you would do?
And then the third is the wild card.
Where do those come from?
They come from your own ideation, from your own possibility.
Almost everybody has some ideas about something else they could do.
If they don't, we do have some ways to help people get that started.
But again, because it's not a plan, it's not a commitment, I'm not job hunting.
I'm just imagining possibilities.
And what might that look like five years out from now?
Now, the wild card you mentioned, the third, why do we ask people to have the wild idea?
If money were no object and nobody would laugh at you.
you, what would you do?
You know, does somebody really want to be in charge of bringing
back the Beanie Baby crate?
isn't opening the definitive Beanie Baby store here in Southern California. Well, who knows?
You could be the one. So that question has nothing to do with will it work. Why we ask people to have
the wild idea is not because it's a great idea. It's because we're teaching you to turn off the
internal critic. You start to have this, oh, I do actually really like Beanie Babies. That's so
stupid. Nobody likes Beanie Babies. You'll be embarrassed. You can't be saying that. So that
voice inside your head that evolution put there for you to make sure that your negativity kept
you from being eaten by the saber-toothed tiger. So we've got a negative bias that's for our good,
thanks to evolution, that really gets in the way of ideation. So we want people to have lots of
ideas about their future. What might I do? What alternately could I do? If I were crazy,
what would I do? Now I'm really on a roll of having possibilities of ideas. I'm not going
to do that to pick one of these paths. The outcome of that worksheet with 15 different
years of possibilities is just on that whole 15 years of possibility,
what couple of things like, ooh, I'd like to, I would like to know more about podcasting. This
thing, I mean, I have no idea how that really works. If I could sit down with somebody like
Dhar Mann and have a cup of coffee, I would so do that. I would so talk to people and try some stuff
to see what it's like. The purpose of the Odyssey plan is to animate your curiosity. We have some
things you're willing to start nosing your way into investigating, not quitting your job for not,
you know, suddenly signing up for a three-year night school to get a master's in the wrong degree,
but a very, very low lift
of investigation to give you some experience that might say, oh, after my fifth conversation
with a podcaster, I now really know I don't want to do that. Or I really know, wow, this is more
interesting than I thought. I'm learning to curate my curiosity, which over time might become
animated that says, now I'm going to start actually thinking about putting a plan together to try
doing this. So it's a stepwise approach to building up enough energy and insight to get down the road
you want to be on. So starting with the identification part of all these different
opportunities,
I love how what you just said about the wildcard aspect, right? And I think a lot of people know
what that big dream is. Everyone knows what the baseline is. Let's just talk about the alternative
for a second. So going back to my example, let's say I'm a school teacher in a job right now. And
I know what, hey, five years from now, maybe I could become an assistant principal or whatever
the hierarchy of the public education system looks like. So I can map out as to the different
milestones that I'm likely to hit if I stay in my baseline career. And I can map out as to the
different milestones that I'm likely to hit if I stay in my baseline career. What is an example of
an alternative path? Is that like if I'm not a teacher, but I could be a school counselor or
like something adjacent?
Not necessarily adjacent at all. Let's say I can think of an example. I know a school teacher who
is at a dinner party and they're talking to a friend of theirs who's actually in the development
office of a nonprofit. Oh, that's a totally different thing. I'm in the classroom with kids
and you're running, raising money shoes. No, but you're a grammar school teacher and you spend all
this time telling stories and teaching early creative writing. You're a storyteller. That's
all I do.
I'm storytelling in an entirely different way. And she goes, what are you talking about? So I said,
well, why don't you go find out what she meant? Then ask her to give you three names of other
development officers in different nonprofit organizations and ask them what they do.
And so she goes off and she does that and goes back. Oh, I really love what they're doing,
because it's still making the world a better place. I'm making the world a better place by
teaching children how to write. And they're making the world a better place by what this
nonprofit is doing, helping brown kids crack into high technology. This nonprofit is doing by
retraining homeless people to be able to maximize utilization of resources.
Whatever it is that they're dealing with, this is really lovely stuff. And it's a completely
different category. I had no idea it even existed. So that's a jump shift that has both a motivational
correlation and frankly has a competency correlation. She could be good at this in
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created for how Texans actually use energy. TXU Energy. Rep number 10004. So the things that you're saying, I mean, you make it seem so easy,
right? Just go talk to three people who are, you know, have some sort of core competency
or experience in these areas. But I'm back to putting myself in my shoes as
25-year-old Dar, who was intimidated to ask questions, was intimidated to be curious. Like,
I wouldn't want to go up to somebody and say, hey, tell me about your job and tell me about
what you like, what you don't like. I'm thinking about going into your career. I mean, how do you
do that? Pretty much you do it just like that. I mean, you know, it's a little easier for the
extrovert, but the truth is this actually works. And what we teach people to do is keep in mind,
it's terribly important to make a distinction between the transactional conversation. Well,
hey, how much do you make and what degree do I need? Have you gotten the openings here? Because
then you're moving people into decision-making and judgment. And the first thing they're going
to say is no. What you want is the narrative conversation. You know, hey, Sean, you know,
it turns out I've done some homework on this. You know, you've got this long history in the
media world and TV and now you're in the podcast world. And it turns out you and I share a common
interest. You think you're incredibly fascinating and I think you're incredibly fascinating. So
we're agreed that Sean's the most interesting guy we know. Why don't we get together and
share our common interests and how fascinating you are? And you can tell me more about that.
Now, I wouldn't say it quite that sycophantically, but surprisingly close because most people's
favorite thing is indeed themselves and what they're doing. Now, our argument is that if you,
and by the way, you go to this place called LinkedIn, where people are living in the public
sector and you find these people who are doing the kind of thing you think might be interesting.
And then you do a little background work on them. So you can actually ask an informed question. You
don't act stupidly and embarrass yourself. So that doesn't help, but that's not that hard to do. You
do it easily these days. And our finding is about seven out of 10 of your requests are likely to get
a yes. You know, if all you're asking for is a 20 minute zoom call. And if it's in person, it usually
goes for an hour or two. And of the three people who said no, one of them's a jerk, like don't
bother me. And two of them like, oh, I got to fly to Beirut tomorrow. I'd love to do it, but give me
a call when I get back in six months, you know? So people are surprisingly available and it does
take a little practice to believe it. But I remember a vivid memory was a young woman, I'll
say, who had a hard time buying into it just the way your question was phrased. And she came back
three years after graduation and we offer office hours are free for life if you ever take our
classes. So she calls him and says, can I have office hours? Sure, come on down. So we meet on
campus, you know, and she sits down and she starts pounding and she goes, you must tell them,
you must tell them it's true. It's true. It's true. I go, great. I'll tell them, Sue, what?
She goes, that talk to people thing, it really matters. And it really works. I go, I know we,
we pushed it pretty hard. She goes, yeah, you were actually telling the truth. I said, no,
don't lie to our students. And she had started to talk to people and found it incredibly
generative. So it really, really works. The human being thing really works.
Yeah. So just going back to a simple example, you're so smart. I have to slow it down just
for myself at least. The Beanie Baby example. Okay. Well, that can make me very glad. So that
checks that box. The economics could work out. Hey, if I could make them for $1 and I could sell
them for $5 and I know that plushies and, you know, are a big consumer market, right?
But is there a need for that? Like it may not solve that need, right? That might be the one
that it doesn't check. So run some prototypes. Let's go on Etsy, see if you can sell five of
them. And so as we're going through this mapping of all the different possibilities that could be
this wild card, you run each one through this three-legged stool test. Yeah. Which is why
when in doubt, prototype. So the lifeblood, the cardiopulmonary system of design thinking
is prototyping. And we prototype. And we prototype. And we prototype. And we prototype. And we
prototype not to make sure we're doing the right thing. That means we think we're done. We prototype
to learn our way forward. The point of a prototype is to learn something. So gee, let's go learn
something about what's going on with the Beanie Baby market before we, you know, sell the house
and bet the farm. We had a particular example of this with a woman who had been in HR. She was a
corporate exec, but I love Italian cooking and I love, I love Italian delis. I spend a month every
year in Tuscany. There's this deli there that I love and I want to create that. And she decided
to, it was her passion. She's just going to go for it. She went all in.
She quit her job. She mortgaged her house. She bought this beautiful deli. She completely
remodeled it. She opened it, including with a kitchen. So it served lunch. And unfortunately,
it was profoundly successful. First time restaurateur worked great. That never happens.
And she immediately found out she hated it because she loved going to a deli. She loved
imagining a deli. And now I'm running one. Oh, and I'm hiring teenagers and they quit every six
weeks. And I'm, and once I find the products people really want to buy, they want to buy it again.
And then again, and they like the stuff in the menu. So I never get to change the menu. I'm
cooking the same damn thing every week and weekend. I'm bored to tears. I'm just turning
the crank. Yeah. That's called being a successful restaurateur and deli owner. Welcome to the retail
world about which she knew absolutely nothing. So she could have prototyped that. Try a couple
of catering gigs, offer to cook for somebody's birthday party or for somebody's rehearsal dinner,
you know, go find an Italian deli that you like and offer to be a stock clerk for free.
for two weeks and see what you learn. There's
all these ways to meet
people, talk to people and try some stuff on your way forward and then find out what it's really
like. And then you make the commitment. When we talk about the actual economics of something,
can I make money? Like I know when I wanted to be a creator and start putting out, you know,
positive messages that help people. One of the things that I was constantly told,
there's so many creators. YouTube is such a saturated place. There's so many podcasts.
There's so many X, Y, and Z. And so I know a lot of people that have some sort of a dream in life
that also is a place that they get stuck as to, you know, there's already hundreds or thousands
or tens of thousands of people that are doing this. And if there aren't, then there's probably
a reason for why there's no one else doing this. So how do you decide if there isn't like,
if this isn't too saturated, if I can still succeed at whatever I'm interested in?
I'm not an economist, but the, um, you know, there are 8 billion people on the planet. There
are many points of sale. There are a lot of people doing, there are a lot of grocery stores. Do we
need another one? Well,
that corner may need one. So first of all, don't be daunted by volume per se, and then take a look
at what are the attributes that seem to go into the people who succeed and the people who seem
to fall off. And then eventually you're going to get to the place we, in, in design, we talk about
yours, there's flair and there's focus. So having more ideas and having possibilities is great.
That's flaring out wide. I'm turning my judgment off because I want to have more ideas. And at
some point I got to commit because if I actually want to do something and design something and
have it become real, I've got to commit, which means I've got to eventually take the
risk of possibly failing. I can manage that risk down by having prototyped and learned my way
forward, but I can't eliminate it. And so what I'm eventually, what I want to do is make sure
that I make myself failure immune by taking risks that I can afford. So if I literally at some point
take a risk, I can't afford to lose. It wipes out my family or it does, you know, I end up
homeless. Okay. That's probably a risk you can't afford. You either need other resources,
other people participating with you. You need to take more testing steps on the way
out. A lot of people, frankly, get impatient and then they take a risk that they really can't
afford. Now that let's say I've mapped out five different possibilities. Let's say I want to do
Beanie Babies. I want to start a restaurant in Italy. I want to be a fashion designer. Let's
keep it three. Let's keep it simpler. What is the next phase after design? How do I decide
which one to do? So in decision-making, it turns out, you know, you have the options
that you're going to narrow them down. It turns out your brain can only handle three to five
options before it overloads. So if you have too many choices,
you really have none. It's called the paradox of choice. So you have to knock it down to a
manageable level. And then you may need to make a good decision, a discerning one, a combination of
objective and subjective elements. Do I care about it? Does it matter to me? Is it something that
aligns with my values? You have to understand that there are multiple ways of knowing. There's
objectively, does it count up? Does the spreadsheet work? Does a competitive strategy work if it's a
business? And then, you know, how does my gut feel about it? How do my friends feel about it? You
know, there's learning capability. There's emotional knowing. There's spiritual knowing.
There's social knowing. There's bodily knowing. You know, every time I think about it, I get a
stomachache. Well, you want to pay attention to that. No one of those is the single telling
factor. But if you're going to be an emotionally, intuitively, spiritually intelligent person,
you want to bring all of those faculties into your decision-making process to make the best
possible, you know, most DAR-like true thing. So you don't inadvertently have your brain talk
yourself into something your heart's unhappy about. You want to be a whole person.
And then the most important part of the decision-making is it turns out is once you
make that decision, implement it as wholeheartedly as you can without constantly rehearsing your
backup alternatives. It turns out, let go and move on. So you get your options, narrow them down,
discern well, then commit and go. Because so many people get stuck in like,
did I make the right decision? Should I go back and reconsider this? I find myself there stuck
all the time. And that steals the soul right out of it.
Right. Yeah. I drive my wife crazy sometimes when I'm facing different decisions,
and then I make one. And five minutes later, I'm like, shoot, did I choose the right one? Well,
what do you think? And what do you, right? And oftentimes, you know, I use this analogy that
if I'm at a fork in the road and there's two paths and I could be stuck trying to figure out what is
the right decision, go down path A or go down path B. One of them is a dead end and one of them will
get me there. I historically, right? Let's say there's two people. So person one is stuck. Do I
go down path A? Do I go down path B? Let's say person two just comes up and
says, I'm just going to go down path A. Well, if they happen to go down the right path, great.
They're leaps and bounds ahead of the first person. But even if path A turns out to be the
wrong path, they could come all the way back to the fork and now go down path B and probably still
get there while that first person is just sitting here wondering which one the right path is.
With the framing of your question brings up one of the problems we're trying to help people solve
because you're using the terms right and wrong. So if I've actually done this odyssey exercise and I've
prototyped these possibilities or had these conversations, the alternatives I'm thinking of
are not right and wrong. Now, one might turn out to fail, but that doesn't mean it was wrong. You
can do everything right and it still fails. Making a good decision has a higher probability of success, but it has
no causal requirement. You can't know the future yet. So that's okay. Life is full of risk. Just
make it as managed as you possibly can. But most people, you know, when they come up with
these alternative ideas, realize, wait a minute, there isn't a right and a wrong. There is, that's
this perception that there really is one optimal me. There are lots
of good yous and you can't possibly know who you'll be turning into as you pick that pathway
until you live into it because we're all growing people. We talk about this a lot in the new book
that our definition of a person is you are a becoming. So in the future, so the
2029 version of DAR, no stuff you can't possibly know you don't know yet. So how can you intersect
him properly? You can't. You just try to make the best decision you can and intersect the future
as it unfolds before you. So now life's job isn't to get it right. Life's job is to make
the best choices we can, live into them as well as we can, and then see what happens next.
We take it as it happens. What happens next. Thanks for that plug right there.
That's exactly what it's all about me because the
missing feature is we don't either control or know the future. And people act as though you're
supposed to have known the future to get it right. That's just dead wrong. It's okay to be a person.
Let's just be people well. I coach football. He knows
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more you could save with Free Nights in Cool Summer. TXU Energy. Rep number 10004. I would say maybe at 2029, you end up in a dark place,
right? Going back to I bought the wrong building or I made the wrong career path choice or whatever
it is. I made a pathway that didn't work out. But somehow, inadvertently,
it took you down a path that led you to another one that in 2030, you ended up better off than you
ever would have imagined, right? So like even how I got here to making content was just because
I failed so much in my life in starting different businesses and different ideas and different
passions. And so many times, whatever I had didn't work out that when I came to realize it and I
wanted to start making content and I couldn't figure out what I was a subject matter expert in,
I was like, well, I'm an expert at failure.
So I can actually talk about failure quite a bit. And then failure became my way of building
a community because it turns out there's a lot of other people out there that have experienced
failure. So even if you make what is quote unquote the wrong decision, right? It may be
the right decision. It may get you further than you ever even imagined. And had you not made that
quote unquote wrong decision, it never would have got you there in the first place.
Well, yes. And where I wouldn't go with that, you may, if you choose to,
that therefore that wrong decision was brilliant. Look, you may have made a mistake,
but you're still a human being and tomorrow's another day. And of course, what you learned,
what was true, who you knew at the time, the day after that mistake came to roost was the day in
which the beginning of the next thing occurred. And then the next thing occurred, and then maybe
a major success occurs. Now it can be kind of lovely to reverse engineer and say, oh,
so I had to make that. That mistake was brilliant. Well, no, it was just a mistake.
But you're not dead yet.
- And you get to try again.
So, you know, Kate Bowler's show, everything happens
happens, you know, which is her reaction against after she got cancer, you know, everything happens
for a reason as though no matter what happens to you, goodness, the universe, or God has ordained
it for your good. And that's just flat false. We don't need to make bad things good. We don't need
to name bad things as good or pain as lovely. It's just painful. It may offer a lesson. And if it
does, take it. I learned more about love in the year after my wife died than I ever knew. It was
the best year of my marriage. Best year of my marriage is the year after my wife died. Am I
glad she died 15 years ahead of schedule? No. I take her back in a minute. But I'm not going to
miss the gift if there's one available. So her premature death at 70 wasn't worth what those
lessons were, but she died. So I said, okay, I'm in it. I'm going to get what I'm going to get.
Let's show up for the ride.
So the thing about life is take it. You don't have to rationalize the whole thing. You just
have to live it. And this is largely why we got sort of dragged into writing the third book. And
no matter what happens, it works or it doesn't work, people on the process of trying to get to
the right answer, get to the goal, it doesn't work. It's not enough. We need more to live a
meaningful life. And we're trying to help people with that question too.
So you said your last year with your wife was after-
The last year.
The best year.
After she died. Look, grief is just love in another form. It happens to have the feature of being immensely
painful. And so what happened was I realized, oh, because we had an incredible and deeply
intimate marriage. We've been together 20 years. She got sick at 69. She died at 70.
And the goal was, our deal was 85. So she outed 15 years ahead of contract.
Okay. And so what I realized was I'm in this immense amount of pain, physical pain. It was
really disruptive. And I thought, wow, not that many people get to do this. This is a privilege
to hurt this much. I need to pay attention to what it has to say.
So in the process of not having her around, experiencing her absence and experiencing what
it meant to me, I learned all kinds of things, all kinds of nuances about what our marriage is all
about that I missed while I was there. And I learned all kinds of things, all kinds of nuances
about what our marriage is all about that I missed while I was there. It's shown an incredibly
bright light. I became so much more sensitive to her presence by her being gone. I finally came to
the conclusion, I guess God decided I was the stronger one who could handle this thing. I was
up to the lesson, not because he took her away from me, but because, well, let's see what Dave
can get out of this. So it was simply true that she died at 70, not at 85, as we had planned.
And so I said, if that's true, what's available here? I want to be in reality,
and available to what's here. And I found a great deal, but spent all my time complaining
about her being gone. I'd have missed the whole thing.
So I know a lot of people could hear that and say, well, if I came to such a realization,
I wish I realized that while she was still alive.
Sure.
Right?
Oh, yeah.
And is it true, just from some of the reading that I've done, that your life design plan
actually has more applications than just finding your career? Like it actually helped you
process grief as well.
Yep.
How did you apply it to processing grief?
In our latest book, which is about how to live the meaningful life. How do you get meaning
out of the life you're already in? Like right now, what's actually going on? Not reinvent
yourself or change things, but what's available right here and right now? And it starts with
acceptance. So step one is acceptance, or the mindset of acceptance. I mean, because
reality is the only place anything happens. So as long as I'm arguing about not what I
had in mind, not what I had in mind, not what I had. So a Buddhist will tell you the gap
between the way things are.
And what you had in mind, what they call suffering. And that particular form of suffering is
elective. You could choose to accept that things are the way they are. So thing one
is acceptance. Thing two is availability. And now that I'm here in this world, okay,
now I'm a widow. Claudia's dead. Shoot. Now what? Well, what's available here? Oh, I notice
all these memories and all these waves of experience of her absence hitting me like
sneaker waves, like a ton of bricks. I could show up for those and experience all these
memories. I could experience them deeply and see what I learned about how I felt about
my wife. I could actually edit my understanding of her presence in my life by watching what
grief can show me that having her on the other side of the dinner table didn't show me. And
you're absolutely right. A bunch of stuff that she tried to get across me. Oh, that's
what you were talking about. I've apologized to her about 500 times in the last five years.
Like now I get it, honey. Well, it would have been nicer if I'd gotten it at the time, but
might as well get it.
Get it now. And I'm not, I'm not going to waste my time and regret about having missed it. So,
you know, do I accept the present moment and can I live into the present moment in as meaningful a
way as life has invited me to do? So just going back to the different stages of your plan. So
the design plan, the design stage and the three-legged stool. So first it does this make
me glad. Test it if you can do a test run. So in this case, exactly. Whether it's a job,
right. Can I go and get that job for two weeks? Whether it's a relationship, Hey, what would being
married look like by spending a couple of weeks with this person? Then does the world need it? So
what is the equivalent of that for a relationship? Boy, well, I will say this. What's a relationship
for? Right. And well, you know, it's for our own joy. And it also, I think because Frisch and I
talk a lot about the us that when in a partnership, you know, there's, there's, there's I number one
and I number two, or there's I and now, you know, and then there's us and this us is, is a bigger
thing. And Frisch made the opposite.
Very early, very early. We're talking about the relationship. And she said, look,
we've been given a gift. What are we going to do with it? And I immediately concurred with that.
And exactly what she meant, she didn't know, but we recognize that. And many couples will
state something like that. Not all, but if your point of view is not merely that, Hey, I like you
and you like me, and I prefer being together than alone. That's probably more than enough for most
people. But for a lot of us, it's like, and if, and if this thing really, if this relationship
is authentic, the more authentic, the better version of me to emerge better than me alone,
and it's a gift to us, then it's gotta be for all of us. It's gotta be for the, the, the small us is
part of the big us. So what's the win in that? What does that look like in our particular relationship?
We've made the policy decision. We are a people first couple. So a lot of our friends travel to
places. We don't travel to places. We travel to people. You know, uh, we took a 21 day road trip.
We stayed at 14 different places with 19 different people.
It's been a lot of fun. We've been a lot of fun.
It could have been three or four days, took a little break somewhere, but you know, we're all
about the people thing. So that's something we're trying to give back to the world in a meaningful
way. It's not a company, it's not a project, but it's, it's our way of being in the world.
So I think a fair question is not merely what are your values and are you aligned? And what do you
care about? And what do you think about family and children? All that stuff really matters.
Um, but also what are we for? And the third piece in the business
sense is, can you make money? And so I guess there are economics in relationships, right?
Um, so what would the economic analysis be in choosing whether a partner is right for you?
Well, simply looking at, okay, how do we want to live and can we afford it? You know, so,
you know, if everybody wants to be the stay at home mom, I know couples read both, you know,
both partners, whether it be two women, two men or heterosexual, everybody wants to stay home
and be a mom. Okay. Who's going to pay for that? You know, there's, we've got to cut a deal here.
You know, so you've got to sit down and take a look at how is it that
we want to live? You know, how are we willing to do this thing? You know, and if, if people
aren't willing to do what's necessary to create the lifestyle that we think we want, and I've
certainly seen couples who duck that question, we'll figure it out later. And that becomes a
point of real enmity, you know, like, you know, I got, I'm not getting what I deserved or you
lied or it's not showing up or, you know, the, somebody's gambling at the racetrack while the
rent check is bouncing. That breaks up a lot of couples. So the practicality of we need to live in
the real world and pay our bills. And somebody who's got to figure out how to do that really
matters. What I'm wondering is when do you decide to pivot? When do you decide, Hey, you know what?
I have tried this long enough and it is not making me happy. It is not working. Whether that is a
business, whether that is a relationship, I find so fascinating about your story that after you
went on and you had this incredible, successful career at Apple, and then, you know, as a co-founder
of electronic arts, right at the peak of your success, your son asked you,
a question that makes you walk away from everything.
Yeah. So Rob was three, which is 40 years ago. A big part of what informs this story is I lost
my father when I was nine, which we later learned we lost him to suicide. That wasn't told to us
when we were kids, but we learned later on. So I didn't have a dad. And actually the only adult
goal I had was to be a dad and to be a pretty good dad. I wasn't trying to change the world. Well,
I was trying to solve the energy crisis at one point, but I wasn't trying to make a lot of money.
That was not really, I wasn't even career-minded, frankly. I just wanted to, you know, kind of do
good stuff and be a good dad and be a good guy. And I sort of fell into Silicon Valley at a very
go-go time, you know, in the early eighties. And at this point in my life, I'm working 80 to 100
hours a week, you know, in startups. And I'm sitting in the family room with a cup of coffee
on a Saturday morning, nine o'clock, and Rob's in the kitchen talking to his mom. And he says,
Mommy, can we play with Dad today or is he just going to fall asleep in the chair again?
Because at that point in my life, every time I sat down, I fell asleep.
Because I slept about three, four hours a night.
And on the weekend, I just tipped over.
And it hit me like a ton of bricks.
I went, oh my God, my three-year-old son doesn't have a father.
Robbie's fatherless because I'm just gone.
And even when I'm here, I'm asleep.
This is not okay.
I am replicating the wrong part of the story.
Fix it.
It took me six years of trying and failing and trying and failing and trying and failing.
But I finally fixed it.
That had everything to do with walking away from electronic arts and leaving all my stock on the table.
Because I figured out, finally, if I keep trying to have it all and I keep missing it,
by the time I get it together, the kids are in high school.
They don't know me.
I'm done.
I've lost it.
There's a window closing here.
This kid's three.
He'll be in school in three years.
He'll be a kindergartner.
Then he's only home half the time.
Then he's in junior high.
He's home a third of the time.
He's in high school.
He's never home.
Get off the dime, Dave.
So I had a sense of urgency.
I think at that point in your life, one thing that helped is that you already had success, right?
I think there's a lot of people out there that might feel, it's too late for me to succeed.
It's too late for me to start over.
When is it okay to start over?
It's okay to start over whenever you need to start over.
I don't think it was.
I never thought of it as start.
I never thought of it as starting over.
I just thought of it as doing what had to be done.
I mean, I had spent years trying to be effective at being a startup executive, a co-founder,
or an executive in a rapidly moving technology company, and get that done in 35 to 45 hours a week
and be a great dad in the evenings, home in time for dinner, and coaching Little League
and teaching Sunday school on the weekend, which is the picture I had.
And I was failing.
I was failing.
So, I simply got clear on my priorities.
Part of this is knowing what you're about.
I thought, okay, if I succeeded all that stuff and make all the money in the world, and my
kids think I'm a jerk, I don't care.
If my kids like me, and they're becoming healthy people, and I've been a contributor to their
lives, and we just barely pay the rent and a modicum of a house, I'm okay with that.
So, getting clear on what matters to you really matters.
And that made the decision very clear.
So, I didn't think I was starting over.
I thought I was just making a necessary adjustment to go find a lifestyle that actually allowed
me to live the life that I had in mind.
It took me a bunch of tries.
I failed three or four more times, and then finally got around to it.
By going gig, what we now call gig, I went independent, became a freelance management
consultant, i.e., a gainfully unemployed marketing guy.
I went from W-2s to 1099s for 30 years, and that finally worked.
But it took me a long time to get there.
It was a lot of experimentation, but I didn't think I was starting over.
I thought I was just doing what had to be done.
You talk about this 80-hour work.
Which I can also relate to as an entrepreneur, a father, someone who has big ambitions.
Why do you feel like working an 80-hour work week for your family is a myth or is not the
correct way to do things?
Well, truthfully, I've not met many 80-hour people who, in fact, are doing it for their
family.
They're doing it for the image.
They're doing it for the money, more money than the family needs, and they're telling
themselves, I'm doing it for you because they don't want to stop doing it.
So I think when it's 80 hours a week for the family, it's probably not.
So you have to be honest with yourself.
It's very hard to live the coherent life if the first person you conned is yourself.
So getting really clear, which also includes having people around you that can tell you
the truth and call you on your stuff.
So you got to get clear on what am I doing and why am I doing it, and what is it worth
to me?
You know, I had sort of fallen for the Silicon Valley story accidentally.
You know, because people kept telling me how cool a thing I was doing, and they wished
they could do it.
So you watch out for ending up in a place where you have the problem.
Parker Palmer, who's an education reformer, I think a lot of, once said, you know, I suddenly
realized I was doing a noble job of living somebody else's life.
You know, the life that Steve Jobs thinks I should be living, or the life that my mother
thinks I should be living, or the life that, you know, the person who's getting all the
likes on Facebook thinks I should be living, as opposed to the life that I think I should
be living.
You know what I mean?
You got to own your life, and you got to own the consequences of it.
Since you mentioned Steve Jobs.
Yeah.
I know you worked alongside Steve Jobs.
Yeah, it was fun.
Well, the number one thing I learned at the time from Steve Jobs was how to work Steve
Jobs.
You know, that was an important skill to survive at Apple at the time.
I fell into Apple in a very strange way.
It's a long story.
But nonetheless, I wasn't trying to get there.
They called me, Adlena.
So I felt like I had nothing to lose.
You know, so I would just tell Steve.
That other people were terrified to say, and if it didn't work, well, fine, screw them.
And if it does, OK.
And I didn't have a personal stake in it.
I was telling the truth for its own sake.
And that worked out fine.
So I've been pretty comfortable with that for a long time now.
I spent a lot of my time just failure after failure after failure.
And in my mind, I always thought, if I could be the guy on that stage accepting that award,
or if I could be on that list, or if I could be. In this publication, or this best X list, I would be so happy.
And that feeling is so fleeting.
Yes.
It feels great for a moment, and then it's over.
And then you're automatically thinking, what is the next to do on my checklist?
But it's like, no, the journey of building something,
the journey of all these experiences that we get to have along the way,
that's what makes life truly meaningful.
I've got to say, just being around your energy. For the most part.
From the moment you walked in, I can definitely feel that you have life figured out
a lot more than a lot of people, so I'm so glad that. Well, if I may jump on what you just said, and pardon the completely obvious pitch.
So you just acted out why I had to write this darn book,
which is everybody's hitting that wall, the wall you're hitting.
Yeah.
Lots and lots and lots and lots of people are hitting, particularly post-pandemic.
Then post the great resignation, 52 million people walk off the job.
Looking for, quote, something better.
I don't know how many of them found it.
Frankly, I think rather few.
Because it's got to be more than this, right?
This can't be all there is.
And so we started talking to people, and we ran into. There were two primary points of view, one of which you just demonstrated,
that I think are leading to that frustration.
One is, if I just hit this achievement, this outcome, if I cure this cancer,
if I get this award, that's what we. We roll all those together as impact.
If I have this impact. Then it's going to be great.
And impact is a very important thing.
It's a very good thing.
It's the number one thing we hear people talk about.
Whether it's scoring the highest thing or making the most money or curing the most cancer,
whatever attitude you have about it, it's still a thing.
That's the number one thing people want.
Second thing is I want to be fulfilled.
I just wasn't feeling fulfilled.
And most people define fulfillment the way that Maslow told them to in 1943,
and we still think he's right, which is to become self-actualized, be all that I can be.
Well, we already have the conversation that said,
you have more.
Aliveness than your lifetime permits you to live out.
So you can't be all that you can be because you're about 10 people's worth of a person.
So if I have to be all of me and I can't get there from here, that's a dead end.
And impact is great, except when it works, which it often doesn't, even if you do everything right,
but the few times you do it right and it even works, it doesn't last.
The glow is very short.
Why?
Because you're a human being.
You're an embodied spiritual intelligence, not a thing.
That award, you get three really nice awards in the conference room, by the way.
You'll do winged guys.
You know?
You got a bunch.
You went up and got to receive a bunch of awards, but they're just standing there.
Yeah.
They're things.
You're not a thing.
So impact is great.
Fulfilling experiences are lovely, but they're not enough.
So what I really wanted, the practices of this other, because those are all about the future
and about an outcome.
There's this other place called now, the present moment, which we call the flow world.
So it's the transactional world where all that stuff is happening.
We spend most of our time there.
And there's the flow world, which is right in front of us right now all the time.
Our encouragement in this new book is spend more time in the flow world.
And we actually redefine the flow channel.
Mihaly Csikszentmihalyi defined flow, the optimal experience, you know, back in the 90s
as this narrow little channel.
No, no, no.
It's much wider.
You can do it while folding laundry.
All you have to do is choose your way into fully participating in the moment you're in.
Wait a minute.
I'm holding this sheet, this 500 thread count sheet that came from India.
And I'm seeing the, you know, the, the, the waves of flax.
And I'm feeling the grain of the fabric as I'm smoothing my hand across it, you know,
and appreciating the fragrance of the candle that allows you to believe I'm going to sleep
on this in a couple of hours.
I mean, you're going to do it anyway.
And I could, oh, I can multitask.
I could be getting steps and jogging in place while listening to a dry man podcast while
doing my laundry.
At least I can multitask.
And guess what?
I, I, I do three things badly and enjoy none of them.
So there's a huge.
It's a huge opportunity that doesn't cost you anything to drop into the present moment
in a variety of ways and become more alive.
Let's do it.
And for those interested in getting this book, where can they get this from?
Well, okay.
So the books everywhere is how to live a meaningful life, you know, using design thinking to unlock,
you know, purpose, joy, and flow every day.
And that's available all over the place.
So get more wonder, get coherent, get some flow, get some people who care about you.
Things are going to happen.
Knowing how much you care about yourself.
how much you've accomplished already in your career,
just sensing your energy.
still feel like you're just getting going. What are you most excited about that's coming up next
in your life? You know, I sometimes say to the upset of my partner, you know, I just turned 73.
I have 11 grandchildren. I'm old. And my next really major milestone is death. I mean, so for
me, I'm in the bonus zone. I mean, I, you know, I am having a great time because I am now free to be
in conversation with people around really whatever's on their mind. I mean, I don't have
a lot of goals anymore. My personal goal, what I call a focus question, I'm moving from production
to presence. Now, I still have roles. I have four part-time jobs. So I'm failing retirement
miserably. And I used to think those jobs were about the goals they represent and the strategies
of the institutions they belong to. And those people who I work with still think I care about
those things. And I do. I mean, I do my work. But what I'm really doing in those roles, I'm like,
I'm a venture partner in a social impact accelerator, that kind of thing. I have that
role. I'm a venture partner in a social impact accelerator, that kind of thing. I have that role.
I have that role. So I can be in the room. I just want to be in the room, you know, because at some
point, you know, Dara may ask a question and I may have something to say. And if that opens something
up for him, I want to be present at that moment. So for me, what I'm really excited about is just
being in the room when the invitation to possibly be of some service occurs and see if I can show up.
And you're not just showing up for me. You're showing up for all the people that are listening.
I'm sure there's so many people that were so inspired by his talk and can use this framework
to practically
help them. I know there's a lot that I'm taking away from this conversation that I can't wait to
apply. And my wife's probably going to be so happy just seeing that I am so attentive tonight
and really focused on the kids. And yeah, thank you so much for being here. This was an absolute
pleasure. It was a delight. It's very generous of you to invite me. Thanks for having me.
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Podcast Summary
Key Points:
A life design approach using design thinking—empathy, definition, ideation, prototyping, and testing—helps individuals explore multiple paths to find meaningful purpose.
The "Odyssey Plan" encourages asking three questions
Real-world prototyping (e.g., offering to work at a deli or help with a podcast) allows people to test ideas affordably and gain insights without committing fully to a decision.
Summary:
The transcription presents a life design philosophy rooted in design thinking and personal exploration, emphasizing that meaningful life choices come not from a single "right" path but from curiosity, empathy, and experimentation. The core process—called the Odyssey Plan—guides individuals through three stages: mapping their current life, imagining alternative paths, and exploring a wild, risk-taking idea. Central to this is prototyping, where people test concepts in low-cost, real-world ways (like offering to work at a deli or join a podcast) to learn rather than decide.
The narrative highlights that success isn’t guaranteed, and even well-intentioned decisions can fail—yet failure is part of growth. Personal stories, including one about a father leaving a high-achieving career to become a present father, illustrate how prioritizing relationships over status leads to deeper fulfillment. The message is clear: life is not about achieving a fixed outcome, but about embracing uncertainty, learning through action, and living authentically.
This approach applies beyond careers to relationships and grief, where acceptance and present-moment awareness foster growth. Ultimately, the goal is not to find a perfect solution, but to live with curiosity, resilience, and connection.
FAQs
The life design process uses a five-step approach—empathy, definition, ideation, prototyping, and testing—to help individuals explore different paths and discover their true purpose through curiosity and real-world experience.
Start by asking, 'What am I curious about?' Then talk to three people in different fields, explore alternative paths, and test small ideas—like a side project or volunteering—before making a larger commitment.
The wild card represents a big, risky dream—like becoming a podcast host or opening a Beanie Baby store. It's important because it helps turn off the internal critic and encourages creativity, even if the idea seems unrealistic.
Yes—success often comes from unique combinations of skills, values, and focus. Instead of competing on volume, focus on differentiation and deep expertise in a niche area.
Prototyping means testing ideas in real life—like offering to cook at a party or working a short-term gig—before committing. It helps learn what truly works and reduces the risk of failure.
There is no single right path. Life design emphasizes that there are many good versions of yourself—each with different strengths and possibilities—and that growth happens through exploration.
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