0:02

For morning brew, this is

0:04

business casual, bringing you combos with

0:06

people you know and some you may not know

0:08

yet to make business less intimidating

0:11

because money talks but it does not

0:13

have to be dull. I'm your host, Nora Ali.

0:16

Now let's get down to business. Business

0:19

casual.

0:20

The word a quitter can

0:22

sometimes leave a bad taste in your mouth.

0:24

especially when it comes to your career

0:26

or big life goals. But

0:28

the truth is, we all quit things,

0:30

whether it's a job, a relationship, a

0:33

habit, or the tenth push up.

0:35

I have quit every job I've

0:37

ever had in favor of new careers. I

0:39

quit the trading floor work at a startup.

0:41

I quit that startup to work in TV anchoring,

0:44

and then I quit TV anchoring to start my

0:46

own thing and host this podcast

0:48

right here. Granted, I always quit

0:50

out loud nicely and with enough

0:52

lead time for my teams to prepare for

0:54

my absence. And our guest today makes

0:56

the case that quitting including your

0:59

ability to quit most effectively and

1:01

knowing when to quit is a

1:03

decision skill worth developing.

1:06

In her new book, Quit, the power

1:08

of knowing when to walk away. Former

1:10

professional poker player, Annie Duke, makes

1:12

the case that learning how to Quit will

1:14

help you make better decisions under

1:17

uncertainty. Something we all

1:19

face at one point or another. For

1:21

example, she knows that success doesn't

1:23

necessarily lie in sticking to things.

1:26

It lies in picking the right thing to

1:28

stick to and quitting the rest.

1:31

I mentioned that Annie Duke is a former professional

1:33

poker player. She won more than four

1:35

million dollars in tournament poker before

1:38

retiring from the game in twenty twelve. and

1:40

knowing when to quit was a key

1:42

strategy for those who dominated the

1:44

sport. In her words, amateurs

1:46

usually hold them. professionals usually

1:49

fold them. And he shared some important

1:51

red flags, signs that tell you

1:53

it's definitely time to quit. and

1:56

how to avoid doubling down on something

1:58

in the face of bad news or

2:00

signs that it is not going well,

2:02

which research shows we tend to

2:04

do. And she tells us why, when you do

2:06

decide to quit, you shouldn't necessarily

2:09

be quiet about it. This

2:11

conversation will change the way you think

2:13

about quitting and success and hopefully

2:15

inspire you to put your time and

2:17

energy into things that are truly

2:20

worthwhile for you. That

2:21

is next after the break.

2:24

I know a lot of you have heard this saying, you

2:26

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4:00

Annie.

4:09

I have so many

4:11

questions for you. I'm a big quitter.

4:14

I've quit every Good. One of my jobs

4:16

I've had and we'll get into that. First,

4:18

let's start with a quick icebreaker. This

4:20

is for a segment called OG Occupations.

4:23

So, Annie, what was your first

4:25

ever job that you've ever had? not

4:28

counting babysitting? Counting any everything.

4:30

Counting anything.

4:31

My real first job was at Kentucky

4:33

Fried Chicken when I was fourteen years old.

4:36

Oh, brown polyester,

4:38

slacks, and, like, smock situation.

4:41

Wow. It was yeah. It was something I

4:43

don't have pictures of it. I wish I did. I'm

4:45

a big KFC fan. Did you enjoy it? I

4:48

mean, did I enjoy memorizing

4:50

what goes in a three piece box? I don't

4:52

know some sort of life skill, I'm sure.

4:56

I like the mashed potatoes, which looking

4:58

back is a little embarrassing. A little sesame

5:00

powder. At fourteen years old,

5:02

I thought they were delicious. I know. I used to

5:04

love the coleslaw. so much. Okay.

5:07

Let's get to quitting. The word quitting

5:09

obviously comes with a negative connotation a

5:12

lot of times. It implies you've

5:14

given up.

5:15

you've been defeated, but that is not your

5:17

stance at all. And I agree with

5:19

your stance. First of all, what

5:21

exactly do you mean by quitting

5:23

in the context of your book.

5:25

So I think, first of all, you're absolutely

5:28

right. If I called you a quitter, I would be completely

5:30

insulting you. I mean, I wouldn't, but you would

5:32

take it as an insult because I'd be calling you a

5:34

loser. But we should it shouldn't be that way.

5:36

Right? We wanna change that. So, you know, I

5:38

think that one thing that people need to realize is

5:40

we think about quitting as one particular

5:42

thing, which is like stopping some large

5:44

thing. So like you're in a job,

5:46

you quit your job. But there's all

5:48

sorts of small acts of quitting that we do all

5:50

the time. Like you're watching a TV show, if you

5:52

decide that it's not for you and you don't watch the

5:54

next episode or you stop in the middle of an

5:56

episode, that would be quitting. if you

5:58

are managing a project at work and

6:01

you decide that's not the right project

6:03

for you to be doing in order to reach your

6:05

goals, that would be quitting. What I think about is you

6:07

can, like, change directions that would

6:09

be quitting or you could exit the court. Mhmm.

6:11

And that would be also quitting. But there's

6:13

also other things that go under quitting light. If

6:15

you change your mind, if you abandon a

6:17

leaf. So I used to believe that Pluto is

6:19

a planet, but now I don't. So that's a form of

6:21

quitting. If I fold a hand

6:23

in poker, I'm not getting up from

6:25

the game, but I'm giving that hand up. Mhmm.

6:28

It's called cutting your losses. That would be a

6:30

form of quitting. If I sell a stock, like selling

6:32

things is a form of quitting because you're quitting your

6:34

ownership. And if

6:36

you fire someone, it's quitting. We just

6:38

have a different word for it because as an employer,

6:40

if I let somebody go, I'm quitting that

6:42

employee. employee relationship. So it's really covering

6:45

basically any kind of situation

6:47

where you started something, and then you decide

6:49

that you don't wanna be on that path in

6:51

one, a change in course. And you

6:53

say it's a

6:54

decision skill that is

6:56

worth developing. Why do you think quitting

6:58

is a skill in itself? So I

7:00

I actually think it's like the decisions

7:02

go that you need to develop in order to be a

7:04

good decision maker. So the reason

7:06

is that when you start things,

7:09

you're deciding to start it with

7:11

very little information. And then

7:13

also the way that thing turns out is gonna

7:15

be partially luck is gonna have

7:17

a huge influence over it. So if

7:19

you think about most things that you start, like

7:21

imagine that you're taking a job or even that

7:23

you're hiring somebody. So let's say, I'm hiring

7:25

you for a job. What do I really know

7:27

about you? Right? Like, I've got a CV.

7:29

I've had a few interviews. I've got a

7:31

couple references. but I actually

7:33

know very little when I enter into

7:35

that relationship with you. And

7:37

that's true pretty much of all decisions

7:39

that we have to make in terms of starting

7:41

things. So there's this huge influence

7:43

of uncertainty, and I assume Nora that

7:45

you've had that feeling after

7:47

the fact of saying, like, oh, I wish I

7:49

knew then what I know now. Mhmm. So this is

7:51

why quitting becomes really important because when

7:53

you have that feeling of, I wish I knew

7:55

then what I knew now, you actually have

7:57

a way to address it,

7:59

which is to take on the

8:02

option to quit. Right? So I found something new.

8:04

I wish that I had done something

8:06

different.

8:07

And so I can, and

8:08

I can quit. And there are a lot

8:11

of forces that are working against

8:13

us when it comes to making that

8:15

decision to quit cognitive forces and

8:17

otherwise, you talk about something called

8:19

the escalation of commitment

8:21

in your book. explain what

8:23

that is and why that works against us.

8:25

So we have the intuition. And

8:27

I think you do too. Like, so I assume, like, when

8:29

you start something, whether it's a

8:31

job or relationship or maybe, like, you make an

8:33

investment. I bet you have the intuition

8:36

that when the world gives you

8:38

signals, that thing isn't going as you

8:40

had hoped. that you'll pay attention

8:42

and you'll stop doing the

8:44

thing that you were doing before. So that I think

8:46

that's an intuition that we all share. but

8:48

there's decades and decades of science that

8:50

shows that not only do we not do that,

8:52

but we escalate our commitment to the

8:54

cause when we get bad news. one of the

8:56

best ways to see that is actually in war.

8:58

Right? Like, think about in the Vietnam war, for

9:00

example, or the war in Afghanistan. You

9:02

started and then things aren't going

9:04

well. Right? It's very clear you're not gaining

9:06

ground. The war isn't going as you hoped.

9:08

You know, Vietnam war. I don't think there was any point

9:10

where anybody thought we were winning that war. Yet,

9:12

we stayed in it for a really long

9:13

time. There's no way to capture

9:16

in one evening's broadcast, the

9:18

suffering and the grief of thirty

9:20

years of a subcontinent war.

9:23

In Vietnam, we finally have reached the

9:25

end of the tunnel, and there is

9:27

no light there.

9:28

Because even though you're

9:31

getting this information that if you

9:33

knew it at the time that you were thinking about starting,

9:35

you wouldn't actually start. But when you're

9:37

in it, once you started, you know, accruing

9:39

losses and having all that stuff happen, you

9:41

actually tend to escalate and increase

9:43

your commitment to the cause it gets you stuck in

9:45

stuff. And it's like not just

9:47

wars, but it's also like jobs and relationships.

9:49

Andy, this also reminds me of the

9:51

sunk cost effect. which you

9:53

write about, can you apply

9:55

the sunk cost effect and the quitting

9:57

mentality to say, accepting

10:00

miss stakes or bad situations that

10:02

seem to have absolutely no

10:04

upside. And I say this from personal

10:06

experience because if there's something bad that's happened

10:08

to me, I tend to walk away from it and

10:10

try to think about what

10:11

lesson did I learn. Is there a reason

10:14

for this to have happened? Is there

10:16

some benefit that I've gained

10:18

versus just letting this bad

10:20

thing happen and walk away. So

10:22

how can you use this sunk cost mindset to

10:24

get over something bad that has just

10:26

happened? Yeah.

10:27

So just for people who aren't familiar with sunk

10:30

cost, it's just basically like once you

10:32

put time or effort or money or attention

10:34

into something. It becomes really hard

10:36

quit it because you if you quit without actually having

10:38

achieved whatever the goal is, you'll feel like

10:40

you wasted all the time and effort and

10:42

money. So you can see that with

10:44

say the vietnam war. Right? Like,

10:46

once you start to have casualties

10:48

and you've spent a lot of money on it, people say if

10:50

I exit before we've won,

10:52

then those the lives that we

10:54

lost will have been wasted. The

10:56

taxpayer money will have been wasted.

10:58

But the problem is that waste isn't

11:00

a backward looking problem. It's a forward looking

11:02

problem. addresses what you're talking about?

11:04

Like, how do you actually get yourself out of this?

11:06

Mhmm. Is the next life that I might

11:08

put at risk worthwhile? Or is the

11:10

next month that I spend in this job

11:12

actually gonna get me what I want or is

11:14

the next month that I'm gonna spend in this

11:16

relationship worthwhile? because what you don't

11:18

wanna do is say, you know, this

11:20

the relationship is not at all what your hopes

11:22

and dreams were. It's not aligned with

11:24

your values. You're really unhappy. You

11:27

don't wanna stand it because you don't wanna I've

11:29

wasted all the time that you already put into

11:31

it. What you don't wanna do is waste the time you're

11:33

gonna continue to spend in it. So

11:35

that's like

11:35

the first problem, which

11:36

kind of is a a way that you have to

11:38

change your mindset. But a second

11:41

thing that you can do, which you alluded to,

11:43

is that the other problem that we

11:45

have is we tend to think when we go

11:47

to quit.

11:47

about how short we are

11:49

of our goals.

11:50

And what we wanna do is shift to what's

11:52

the progress that we've made along the

11:54

way. If you're climbing mount Everest and you

11:56

turn around three hundred feet from the summit,

11:58

you failed.

11:59

because goals are like really pass

12:02

failed. Right? but you didn't

12:04

fail. You climbed twenty nine thousand feet in the

12:06

air, which is, like, a lot more than it was fueled

12:08

it. And so one of the things that I try to

12:10

recommend is First of all, think about when you're walking

12:12

away from something like what have I achieved

12:14

and what are the things that I've learned

12:16

along the way. But then also,

12:18

it's when really good to prioritize projects

12:21

and goals where even if

12:23

you don't make it to the ultimate goal, there's a

12:25

whole bunch of learning and achievement that

12:27

you could take out of it. Like, things that aren't so old

12:29

or nothing. Mhmm. That makes sense.

12:31

And there is preparation that you

12:33

can do ahead of going

12:35

into a new task or a new job,

12:37

you highlight something called kill

12:39

criteria. So some practical

12:41

guidelines for overcoming those negative

12:43

assumptions about quitting. what do you

12:45

mean by kill criteria? And how can

12:47

we start to come up with our own?

12:48

Let's imagine in the future. So

12:50

I'm going to start something. It could be a relationship.

12:52

It could be a job. It could be investing

12:55

in something, it could be running a race,

12:57

whatever it is. A really

12:59

simple example of a kill criteria

13:01

is when people are mountain climbing, they have

13:03

something called a turnaround time. So

13:05

when you're going up Everest, let's say, on Summit

13:07

Day and we'd camp four to go head

13:09

toward the summit, the turnaround time is one

13:11

PM, which means no matter where I'm on the mountain, it

13:13

doesn't matter whether I made it to the summit or

13:15

not. I have to turn around at one PM otherwise,

13:17

it's too dangerous because that means that I'm gonna be

13:19

coming down the mountain in darkness and

13:22

that's not good for anybody. So that's a

13:24

really good example of just a very

13:26

simple kill criteria. and you do

13:28

that in advance because if you're

13:30

actually in it and it's one pam and you haven't thought

13:32

about it in advance, you'll convince yourself you're

13:34

close enough to keep going. because we

13:36

don't like to abandon things. Right? Like, we

13:38

have a real bias against it. It

13:40

feels like it it might be difficult to know what

13:42

your kill criteria might be

13:44

going into a job So let's say, for

13:46

our listeners sitting at home or sitting at

13:48

work, who have not come up with their kill

13:50

criteria to leave a job or situation,

13:53

what are some red flags that you should

13:55

look for in the moment to know that it's

13:57

time to quit and

13:57

not too late to quit? What

13:59

question do you be asking yourself?

14:01

what you wanna do is kind of like, you know, you

14:04

wanna be on a regular basis

14:06

assessing your situation. So

14:08

think about what you were hoping for in

14:10

terms of your own happiness, your own

14:12

eagerness to do the work, collegiality,

14:15

fulfillment, maybe it

14:17

could be monetary. Like, where do you expect it

14:19

to be in terms of compensation? What

14:21

were those things that made you think that

14:23

this was a good job for you to take in the

14:26

first place? and then reassess that and do

14:28

that on a regular basis. So

14:30

I suggest just like people do quarterly

14:32

business reviews, you should do a quarterly

14:34

personal review. And you should say, like,

14:36

is this still aligning with my values? Am

14:38

I actually getting where I wanna go? Am I

14:40

enjoying my work? If I were thinking

14:42

about taking this job today, would

14:44

I? Now that's

14:46

actually kind of a hard thing to do. So what

14:48

is really actually even better to

14:50

do is not to try to

14:52

say, is this something I would want to start today?

14:54

But instead, when you're doing that, like,

14:56

quarterly personal review, say,

14:58

what am I hoping to see at the end of the

15:00

next quarter? And it just turns out

15:02

like thinking in advance like that

15:04

is easier for us than thinking

15:06

in the moment. Think about what are the red

15:08

flags I might see over the next three months

15:10

And at that point, you know, you have more information about

15:13

the situation you're in anyway, so you can

15:15

predict what those things are. So you have

15:17

a really annoying coworker

15:19

who doesn't do their job in expect you

15:21

to clean up after them. Say,

15:23

if that's still going on in the next three

15:25

months, even if I've talked to my

15:27

supervisor, I've talked to my coworker, it's

15:29

still happening. And I'm having

15:31

to do two jobs basically because I'm

15:33

picking up their flag. That's gonna be enough for

15:35

me to say, walk away. So it's never too

15:37

late to start thinking ahead. Even if you didn't It

15:39

is a la carte. late. You can do it today.

15:42

Yeah. You can do it this court. That is

15:44

exactly right. I love the practical

15:46

advice. We're gonna take a very quick break more

15:48

with Annie when we come back. This

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wise or wherever you

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listen. So before

17:41

we get

17:44

into

17:44

the buzz phrase, quiet quitting, which

17:47

has existed for a long time. We're just

17:49

talking about it more now. Just gave it a different

17:51

word. Exactly right. And it's on

17:53

TikTok more. That's why we're talking about it. So let's talk about

17:55

actually quitting your job. And

17:57

I've come across at least two

17:59

different schools of thought. One,

18:01

quit your job if you don't like it, and then put

18:03

in your fully committed time to

18:05

finding the next thing or starting a company,

18:08

whatever you wanna do. or

18:10

two, on the other side, have something

18:12

else lined up before you quit your job.

18:14

Have something else that you can walk

18:17

away too. what is your take on that

18:19

if, hypothetically, your

18:21

financial situation is not a

18:23

consideration. If you're in a world where

18:25

the financial situation doesn't affect you at

18:27

all, and you're taking into

18:29

account the risk of a resume gap, which is

18:31

something that you would want to consider. So let's take

18:33

those two things out of the equation. A

18:35

resume gap isn't gonna hurt you and

18:37

financially, you're fine. Then you should quit.

18:39

And really honestly, the reason that you should quit is

18:41

that when you're engaged in something, it

18:43

it just block you from being able to

18:45

really truly explore other

18:47

options. But also you may find other things that are

18:49

more fulfilling and you're gonna be

18:51

more likely explore options that are

18:53

farther away from what you might think.

18:55

You may actually explore, like, switching

18:57

functions. You may be more likely to do that kind

18:59

of thing. or you may decide, in the meantime,

19:01

you wanna go get skilled up on something

19:03

so that you could actually, like, switch truly

19:05

switch your career. And I think

19:07

one of the best examples of this actually comes from the

19:09

great resignation. Mhmm. So

19:12

we think of the great resignation as

19:14

everybody just quit. But

19:16

that's actually not what happened.

19:18

What happened was that the people who

19:20

were specifically furloughed,

19:23

let go, or laid off -- Mhmm.

19:26

so the service workers. Right? So they were

19:28

the ones who really got affected at the

19:30

beginning of the pandemic. People like us who worked

19:32

on Zoom kind of continued on.

19:34

Right? So they got let go. And

19:36

then when the great reopening happened, when all of

19:38

a sudden there was lots of employment available, they

19:40

quit their jobs. Now, they didn't quit them

19:42

to do nothing. They quit them to go to

19:44

another position. And the thing that you

19:46

can surprise there is that they were probably unhappy

19:49

beforehand, but had that event not occurred --

19:51

Mhmm. -- where they just the cord was

19:53

cut, They probably wouldn't have explored

19:55

and found out. Like, you know what? I don't really actually

19:57

like this job that much. I think there's other

19:59

opportunities for me that I wanna go do.

20:01

So there's something really freeing

20:04

about not being in something

20:06

that lets you go and really

20:08

do true exploration of the space. But

20:11

again, yeah, that's assuming there isn't a monetary issue or a

20:13

resume gap issue. Yeah. I just wanna give

20:15

that big caveat. Definitely. So

20:17

you can cut the cord for yourself

20:20

then. If not because of pandemic, if

20:22

you quit, you've you've

20:24

cut the cord. If you quit, that's right. because

20:26

sometimes quitting is voluntary, sometimes it's

20:28

foisted upon And obviously, when it's

20:30

hoisted upon us, we don't get to make a decision

20:32

about our monetary situation or resume

20:34

that situation. But we can

20:36

also do it voluntarily do you think

20:38

you'll make a better choice about your next

20:40

partner if you look for them while you're in a

20:42

relationship? Or if you look

20:44

for them -- Right. -- after you've already left

20:46

a relationship. Right? So

20:48

it's true with everything. Right? It's true of

20:50

all forms of quitting. Whether it's a relationship

20:52

or a job, you're probably gonna do a better job

20:54

kicking if you're not in the other thing.

20:56

Yeah. It's not gonna be good if you're

20:58

casually swiping your hands when you're still in

21:00

a relationship. Like, looking for the next

21:03

best thing. But you know what?

21:05

That's actually kind of, like,

21:07

relationship quiet with it. Yeah. Yeah.

21:09

It's sort of the same thing. Actually, you know,

21:12

brings me to another point where even

21:14

if you're objectively happy

21:17

in a role doing what you're

21:19

doing, there's this desire for what's

21:21

next? What's the next

21:23

best thing? How can I do even

21:25

better? How do you quit trying

21:28

to strive for something else

21:30

even though you are happy in

21:32

your current situation. First of all,

21:34

I think that you should always continue to

21:36

strive for other things, not

21:39

because you would necessarily switch,

21:41

but because your circumstances

21:44

can change. So you could be

21:46

super happy in a relationship and then things could

21:48

change. You could be really, really happy in a

21:50

job, but then something could happen,

21:52

like, you know, you're leader could leave and

21:54

somebody knew could come in. So I think

21:56

that we wanna make sure that we're

21:58

striving in the sense of, like, always sort of keeping

21:59

our eye on the landscape. Like,

22:02

if we're recruiters are calling, it's okay to have conversations

22:04

with them. Like, not in a sense that you're gonna

22:06

leave, but in a sense that your

22:08

situation may change, I

22:11

really recommend two things.

22:13

One is, often those

22:15

feelings are very transitory. Right?

22:17

Like, it's an impulse. stop and say, oh, I just had

22:19

a thought that maybe I'd like to strive for something

22:21

else. How long do I need to

22:23

find out that this isn't the place for

22:25

me anymore? that I really do wanna go. And maybe

22:27

that's three months. The other thing that you can do though

22:29

that I think is really important, and this is a little bit

22:31

what a parent's role is, is

22:33

to get someone to help you with the

22:35

decision. who's been there done that, who

22:37

really trust, who totally has your back,

22:40

like, you hate the piano, and

22:42

you're saying, I wanna quit. and

22:44

they're sort of helping you to figure out, do you just

22:46

hate it? because you're it's hard right now,

22:49

but it's worthwhile in the

22:51

long you know, parents aren't perfect at

22:53

it, but this is what they're attempting. And I

22:55

think that's just like super helpful

22:57

is go find someone to help you with

22:59

the decision. on that topic, you talk about enlisting the

23:01

help of a quitting coach. Yeah.

23:03

So what quality should

23:05

this person have? And

23:07

should it be your friend or not

23:09

your friend? It has

23:11

to be someone who has your long term best interest

23:13

at heart. So if you're

23:15

asking a friend for stock advice, that's probably bad unless

23:17

they're unless they're an expert. So you wanna

23:19

make sure that their opinion is gonna be valuable for

23:21

the thing that you're asking them about.

23:24

But other than that, it's actually mostly on you.

23:26

And in particular, where it's mostly on you is that

23:28

you have to give them permission to tell you the truth.

23:30

Mhmm. Because the problem is that

23:33

friends tend to want a cheerleader, which is reasonable. When

23:35

you're complaining about a relationship, they're not

23:37

gonna speak that. Yeah. They're gonna be, yeah, I'm

23:39

sure you could work it out. Right?

23:41

you have to give them permission, and you have

23:43

to say, look, I'm asking you to say

23:45

some things that you think I'm not gonna wanna hear, but

23:48

I do wanna hear them even though they're hard because

23:50

it's gonna help me in the long run. So,

23:52

yeah, it shouldn't just be, like,

23:54

random friend. It should be friend who has

23:56

a good opinion about the thing you're asking. And

23:58

then you have to give the person permission

24:00

and trust that they're gonna tell you their truth.

24:02

Let's say you have a

24:04

friend who has not given you permission, but they're

24:06

a good friend, and you see that

24:09

they're in a situation. situation

24:12

that need they need to get out of, whether it's

24:14

a job or a toxic relationship. And

24:16

I only ask because I've had these kinds of conversations

24:18

in recent history with my friends

24:20

In that case, if you haven't been given permission, do you

24:22

just not say anything? I tried it

24:25

obliquely probe. So how's

24:27

that job going? How's that

24:29

relationship going? There's a couple of things you

24:31

can do. One is when they

24:33

start saying, oh, it's actually not going well, what do you

24:35

think? You can actually say,

24:37

well, I need to understand. Do

24:39

you want me to tell you really

24:41

what I'm seeing is because, you know,

24:43

I I need to know, or is this something where you're

24:45

really looking to vent you're

24:47

looking for just an ear, like someone

24:49

to hear what you have to say. So

24:51

you can create that permission by

24:53

being really clear. what I found is

24:56

that, mostly people actually just kind of want

24:58

event, and that's normally what they'll say to you is that

25:00

I want event, and then you accept

25:02

it. But what I think as a good friend you should

25:04

do is say, okay,

25:06

they're venting now and I recognize they're

25:08

not gonna be in a position to hear what

25:11

I see. but you can use the kill criteria

25:13

trick. And you can say to them, oh, yeah.

25:15

Like, this seems like a really bad situation.

25:18

Have you sat down and had a really hard

25:20

conversation with leadership at your

25:22

work, and how do you think things will have

25:24

changed? And what you can throw in

25:26

there is how long do you think this situation is sustainable

25:28

for you? So now you can kind of get a

25:30

deadline. So let's say they say,

25:32

like, oh, you know, I think I can only take it for

25:34

three more months. You're like, Oh,

25:36

yeah. No. I think that's good. Like, three more months.

25:38

That's really good. So, like, at the end of three months, like,

25:40

what does that look like? If things are

25:42

better, what does that look like? And if

25:44

things are worse, what does that look like and have that

25:46

conversation with them? And generally, that

25:48

then implies permission to have the discussion in

25:50

three months, and it's a little bit of a trick to

25:52

do it. And the thing to realize is that, are they

25:54

gonna be in that situation three months longer than

25:56

if you were the,

25:57

you know, ultimate ruler of the world?

25:59

Sure. we all know what happens. Otherwise,

26:02

as they complain to you and then three months later, they

26:04

complain to you again, and then three months later, they complain

26:06

to you again. So you're getting them out of

26:08

it maybe in three months instead

26:10

of a year. Sure. And that's huge

26:12

one. You know, we all have short lives, like, let's

26:14

save some time. So you're not

26:16

imposing your opinion on your friend

26:18

necessarily. You're asking questions such

26:20

that you're helping them arrive at the

26:22

conclusion themselves. Right. If they happen

26:24

to give you permission -- Mhmm. -- you know, you

26:26

can give it to them right there. But,

26:28

like, I mean, you have to sort of tread lightly on

26:30

that stuff and understand that in the moment, it's

26:32

very hard for people to hear that you're telling

26:34

them that they should walk away. because, again, that's

26:36

the moment where you go from this thing that doing failing

26:38

to now

26:39

it's failed.

26:40

Yeah. That makes sense. Another

26:42

very quick break more with Annie. When

26:44

we come back?

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27:39

Let's

27:42

talk about some quitters, specifically

27:44

starting with you yourself, Annie. You

27:46

were at

27:47

a crossroads early in your career. You

27:49

were a graduate student

27:50

in cognitive psychology. an

27:52

aspiring academic, but you quit

27:54

academia and turn to professional poker.

27:57

Why was that? It does sound very useful

27:59

as a

27:59

skill though. it is really

28:02

useful as it skill as it turns out. You

28:04

know

28:04

what? That was forced quitting. I it was kind

28:06

of a great resignation moment for me. So --

28:08

Mhmm. -- what happened was I did five years of graduate

28:10

at the University of Pennsylvania. Just

28:13

in terms of five years, it means that I

28:15

did all of my exams. I was

28:17

already teaching. I was actually on the

28:19

job market already. and I was about to defend my

28:21

dissertation. Okay. So, like, this is, like,

28:23

all my art. Oh my god. This is, like,

28:25

okay. I'm at the end. I've been

28:27

struggling with a pretty chronic stomach illness

28:29

and it it got to be really cute. And at the time

28:31

I was thinking, well, I'm just gonna go out on the job

28:33

market and then hopefully I'll be able to

28:35

figure out this health issue. And my

28:37

body was like, Nope. That's not gonna

28:39

happen as I ended up in the hospital for a

28:41

couple weeks. So that happened to be

28:43

right when I was supposed to be going

28:45

and interviewing for jobs. And

28:47

then it became clear that I it

28:49

was a really bad stomach issue. So I had lost,

28:51

like, twenty five pounds

28:52

or something like that. So I just wasn't

28:54

it wasn't

28:55

like I could postpone the job

28:57

tax. I just kind of had to cancel it for that year

28:59

and take a year off of school so that I

29:01

could to waste what was going on. And when I

29:03

left school, I needed money. because so I was,

29:05

like, forced to quit. Right? because I got sick. And

29:07

then I started exploring. And the

29:09

thing that I explored was poker.

29:12

and I started playing it and I really loved it

29:14

and it turned out I had some talent for it. And

29:16

what I was gonna do for that year in the

29:18

meantime before I went back out on the job market ended

29:20

up being a career for almost two decades. You

29:22

know, and I think that that's the big lesson from

29:24

that. Right? Look, when you're forced to

29:26

quit for whatever reason, it doesn't always

29:28

work out well. but

29:30

there's a lesson in there, which is

29:32

that causes you to explore other

29:34

things. And when I was an academic,

29:36

I knew how to play poker. I had played little poker

29:38

and my brother played poker and never crossed

29:40

my mind ever that this would be

29:42

a job until I was four

29:44

to consider it as a job. And then I

29:46

found something that was amazing for me. Right?

29:48

So I mean, I get that there's luck involved in

29:50

that, but there's a lesson involved in that as well.

29:52

And the quitting piece of poker obviously is

29:54

a is a big part of why you

29:56

wrote this book and you cite one

29:58

of the biggest differences between most players

30:01

and the world's best players in poker is how

30:03

often they quit. So I'm gonna cite a stat

30:05

that you have in the book. In Texas,

30:07

Holden Poker, after professionals and

30:10

amateurs at the starting cards they're dealt. The pros

30:12

play fewer than twenty five percent of their

30:14

hands before other cards hit the

30:16

table, whereas the amateurs play

30:18

more than fifty percent. Why

30:20

is

30:20

that? Take us real quick into the psychology

30:22

of a professional poker player.

30:25

Okay. So professional

30:27

poker players are thinking about

30:29

two things. is this hand worthwhile?

30:31

And then the other thing they're thinking about

30:33

is something called opportunity cost, which

30:35

we've alluded to, which is if I put this

30:37

money toward this hand, that's money that I can't put another

30:39

hand. And so you're trying to get your

30:41

money into the best situations possible. And

30:43

when you're playing a game of Texas, hold them and

30:45

there's nine people the table, you wanna make sure

30:47

that you have a better than average hand. Right?

30:50

And those are few and far between when there's nine

30:52

people at the table. So actually, if you think

30:54

about it, with nine people at the table

30:56

twenty five percent of the hands is a

30:58

lot. So they're saying, like, I'm more skillful

31:00

than you are, so I'm willing to play, like, than

31:02

my fair share of hands. But we don't think we

31:04

are because we're good players and so we play twenty

31:06

five percent. Partly because we know

31:08

we're gonna ditch the hand pretty quickly

31:10

and as we find out it's no good. So compare that

31:12

to amateurs who are playing over fifty percent since

31:15

they're doubting what is going on. So

31:17

why are they so much worse at ditching their hands,

31:19

it's really hard to walk away when you

31:21

don't know for sure that you had to. So

31:24

remember, like, when you're playing a

31:26

poker hand, you've invested money in

31:28

the pot. And if you fold, that's what

31:30

you're saying. I'm not getting that money

31:32

back. It's very hard for people

31:34

to say I'm okay folding and not getting my money

31:36

back unless they're absolutely short.

31:38

So this is something that's just true of

31:40

quitting us. We often won't do

31:42

it until we just don't have another

31:44

choice and until the choice is so

31:46

clear that there's nothing else we

31:48

can do, the possibilities. Right. So

31:50

and and what's weird is this turns into an

31:53

skews. So somebody will start

31:55

a company, let's say, and it's not

31:57

going well. And then they'll always point out

31:59

to, like, Oh, but that guy's

32:01

company was totally on the brink of

32:03

death, but they kept at it and ended up

32:05

succeeding. So you you

32:07

brought up, you know, the the a company example

32:09

for startup founders who are going

32:11

through troubling times. It doesn't feel like

32:13

they're getting any traction with

32:15

their customer

32:16

base. Their up

32:18

their investor dollars, how do you

32:20

know if you should persevere and

32:22

keep pushing and keep trying versus

32:24

quitting? And you have a great example with

32:27

Stewart butterfield as an example of, like, the quit version

32:29

of that, but when do you know it's the right time

32:31

to keep going? I think store Butterfield

32:33

demonstrates both sides of the equation. There's

32:35

lots of lessons in here. His second company, which was called glitch.

32:37

And he was developing a game called Game

32:39

Never Ending, which is like this massive online

32:42

role playing, cooperative, world

32:44

building game, which was like a huge credit start

32:47

darling. And they actually had five thousand

32:49

die hard users and six million in the bank

32:51

with Andres and Horowitz and Acel

32:53

having backed them. So they had lots and lots of money in

32:55

the bank. And that, you know, they had users.

32:57

Right? But they all kind of had

32:59

figured out that there was a problem, which is

33:01

for every user that they got

33:03

like, ninety five people visited the game or

33:05

it was my I think it was more than that. It might have

33:07

been ninety nine people, and they played it for

33:09

seven minutes and left. So in

33:11

order to get these, like, die hearts who play twenty hours a

33:13

week or more, you had to get the game in front of

33:15

a lot of people. So on

33:17

the weekend of November eleven and twelve, they have

33:19

a really huge weekend. That's sort of

33:21

the end of this marketing push. And

33:24

Stewart Butterfield goes to bed and he can't sleep.

33:26

He's really it's restless. And he wakes up

33:28

the next morning and he sends a note to his

33:31

cofounders and investors saying, I woke up this morning

33:33

with the dead certainty that Glitch was dead.

33:35

So it's like, well, what's going on there? Because they're

33:37

growing users. but he's thinking more like a

33:39

poker player and he's like, well, if we were

33:41

to maintain this growth, it would take us thirty

33:43

one weeks to breakeven. And I don't

33:45

think

33:45

we can maintain this growth. because

33:47

at some point you saturated the gaming

33:49

audience. Right? We're not gonna be able to maintain it,

33:51

so it's gonna be way more than thirty one weeks to

33:53

breakeven. At which point he just realized it wasn't a

33:55

venture scale business. And what was

33:58

I think important about this is one of the things

33:59

that really concerned him was that his

34:02

employees were taking basically no

34:04

cash in exchange for

34:06

equity. he felt like a moral obligation that once he realized the equity

34:08

wasn't worth their time, he needed to

34:10

let them go. Now notice this is sort of

34:12

to your point about progress versus being

34:14

short of the goal, it's turned on

34:16

its head because most people think I owe it to my employees to keep going.

34:19

Now going back to that idea of force

34:21

quitting or what quitting does for you

34:23

in terms of exploration, Once

34:25

he shuts the company down, literally two

34:27

days later, he's like, oh, we have

34:29

an internal communication tool here that we

34:31

really like around here. We don't have

34:33

a name for it, but I don't know. Maybe that's the

34:35

next product. Let me give it a name,

34:38

which was searchable log of all company

34:40

knowledge,

34:41

which is Slack. The theme

34:42

I'm seeing here is always look ahead and don't dwell on what could

34:45

have been. Don't look backwards. It is

34:47

about what's happening now and how that's gonna

34:49

impact you in the future.

34:51

I wanna get

34:51

your take Annie on how you quit when the

34:54

stakes are really high and

34:56

specifically very public. So let's say your

34:58

reputation and public embarrassment

35:00

are on the line. And I'm thinking about

35:02

two pretty recent high

35:04

profile examples like Quibi launching

35:06

and shutting down within the

35:08

same year, and they had raised over one

35:10

point seven five billion dollars CNN plus

35:13

shutting down after a month

35:15

they had spent a reported three

35:17

hundred million dollars that they

35:19

sunk into it. So if you're a high profile company

35:21

or you're a leader of a high profile company,

35:23

what is going through

35:26

your mind? in these situations that leads you to quitting as a

35:28

strategy. So first of all, let me say

35:29

good for them.

35:32

Because again, Okay. Yeah.

35:34

They had spent a bunch of money, but were they gonna

35:36

spend a lot more? And I think most people in that

35:38

situation, particularly when it's high profile, would be unwilling

35:40

to shut it down in such public way.

35:42

And a lot of the reason is that, again, it's super

35:44

public. And when it's really public, the people who are the decision

35:47

makers have their identities kind

35:49

of on the line. and

35:51

it's really hard to quit your own identity.

35:54

And this is particularly true

35:56

when you've done something public

35:58

that is out of the mainstream

35:59

in some way. Mhmm. So there's two

36:02

issues that play together. So the first is

36:04

called internal validity, which is the

36:06

desire for us to see ourselves

36:08

as consistent. And then there's

36:10

external validity, which is how our other people

36:12

gonna view us. What I think is

36:14

interesting is that we think of them as

36:16

the same. So the things that we're worried about

36:18

ourselves. We think that other people will think

36:20

about us. But in general, it's actually not.

36:22

There was a great story that Ken Kamler told

36:24

me who was a doctor. He's a doctor.

36:27

who has been a doctor on Everest, like part of

36:29

the medical team for expeditions climbing. And

36:31

he was actually trying to sum it in

36:33

nineteen ninety four and they were on the

36:35

southeast ridge, which is pretty darn close to the summit, but the climbing conditions were

36:38

terrible. And so they all made the decision

36:40

to turn down turn around. And what he

36:42

said was

36:44

I just thought the whole time about when I got home. Everybody's gonna think there a failure.

36:46

Like, he just had this whole, like,

36:48

talk track and it said about what they

36:51

were all gonna think. And when

36:53

he got home, That I I could have done that. Yeah. Yeah.

36:55

Like, how'd you actually turn around? Like, they had

36:57

the intuition. They were like, that would

36:59

be really hard. And

37:01

it turned out were actually really proud of him. And that was

37:04

the moment that he said. Like, I realized that the

37:06

goal wasn't to get to the top of the mountain. It was to get

37:08

back down.

37:10

it sounds like it's a good signal if when you shut something down, you

37:12

quit something, other people are, like, surprised

37:14

by it. Wow. Yeah. It was quick versus

37:17

waiting until people are, like, oh, you know, I saw

37:19

that coming. Right. And and in fact, it's usually

37:22

worse than that, which is if you wait

37:24

for that, they usually say, oh, yeah. You should have done that

37:26

a lot earlier. there. Right.

37:28

Right. A couple more things

37:30

before you let you go, Annie. We have a

37:32

fun segment called shoot

37:34

your shot.

37:42

So this is

37:46

where you tell me your wildest

37:48

ambition, your biggest dream, your

37:50

moonshot idea, It could be

37:52

personal or professional. It is your chance to

37:54

shoot your shot. Okay. So my

37:56

moonshot idea is something that I'm actually kind of

37:58

already doing. So I'm

37:59

co founder of something called the

38:02

Alliance for Decision Education.

38:04

And what we're trying to do is get

38:06

Decision Education into every k through twelve

38:08

classroom. So I write about it. Right? I wrote thinking about how to decide, quit. This is the

38:11

space that I write in. And when you look

38:13

at books like, like Daniel Kahneman, right,

38:15

thinking fast and slow, or

38:18

Richard Taylor and Cass Bernstein with Nudge or Katie Milkman with

38:20

how to change, there's so much work that's done

38:22

on adult decision making and like what

38:24

goes wrong and what goes right. but

38:27

we spend all our time teaching kids like

38:30

trigonometry. Like, why? Like, we

38:32

should be teaching them to make better decisions.

38:34

Right? So we wanna

38:36

get, like, this field like, we wanna define this field of decision

38:38

education, get it into every single K through

38:40

twelve classroom. And it's a

38:42

total moonshot.

38:44

because first of all, the education system's really it's

38:47

really hard to, like, turn that

38:49

boat around in or even

38:51

change directions slightly. it's

38:53

just really hard. And when you look at, like, other

38:56

educational movements, like social

38:58

emotional learning, for example, it took

39:00

thirty years. to get into

39:02

classrooms, but aren't we really happy that it's

39:04

there? So this is the definition

39:06

of a moonshot. How I wish that could have been a

39:08

part of my curriculum? Like,

39:10

I love trig, but I'd rather learn about decision making

39:12

than about triangles. Well, the thing is that you

39:14

can learn trig later if you need

39:16

it. I'm not sure why we're torturing, like,

39:18

you know, ninth graders.

39:20

Wait. Okay. Final. Thank you for you, Annie. We

39:22

have a very quick game. It's

39:24

called who, quit, what?

39:26

Okay. So I'm gonna give you a

39:28

few clues. and you have to try

39:30

to guess who the famous critter

39:32

is based on those clues. And

39:34

this is true. I'm gonna be so bad at this

39:36

game. It's totally fine. it is

39:38

challenging. I will say that upfront. So if you get

39:40

them all wrong, I understand, because I

39:42

would have gotten them all wrong. So this is from

39:44

Times list of

39:46

famous quitters. Okay. Number one. Here's your

39:48

clue. In nineteen sixty nine,

39:50

after finishing his band's

39:52

final album,

39:54

this singer musician decided to call it quits. While lots of

39:56

factors contributed to the

39:57

group's breakup, he was especially

39:59

miffed when he offered his

40:02

new song cold

40:04

turkey as a potential single to the

40:06

band and they didn't want it. He

40:08

released the song under the name of his

40:10

new side

40:12

project. Who

40:12

is this quitter? Nineteen sixty nine, it's

40:14

a band. Is it

40:16

was it Eric Clapton? Uh-uh.

40:19

Okay. I give up Think

40:21

of the most famous band in

40:23

the sixties. Well, it's not the Beatles

40:25

because they didn't break up before then. It

40:27

is the Beatles. It is the beat,

40:29

and it's the deal. Is it John Lennon? Is it John Lennon? So

40:31

Lennon broke this decision to his

40:34

bandmates and September of nineteen

40:36

sixty nine, though the band's

40:38

demise wouldn't be confirmed until a couple

40:40

months later when Paul McCartney delivered

40:42

the bad news in a life

40:44

magazine interview. Oh, okay.

40:46

But I just watched that wonderful

40:48

documentary, so I'm so sad that I I thought the

40:50

Beatles broke up in, like, nineteen seventy two,

40:52

so that was my bad. Okay. Next

40:54

question. This forty two year old gave up

40:56

his inherited job for love

40:58

in nineteen thirty six. And to

41:00

this day, he remains the

41:02

only English sovereign in history to voluntarily

41:04

abdicate. It's the king of

41:05

England. Is it

41:07

Edward?

41:07

Yes. Wow. I would have had

41:10

no idea about this

41:10

one. I had no idea. Edward the eighth,

41:13

you're a genius. Okay. So more

41:15

info for our listeners. He said

41:17

this in a televised speech. I have found it impossible

41:19

to carry the heavy burden

41:21

of responsibility. and

41:24

to discharge my duties as king

41:26

as I would

41:28

wish to do

41:30

without the

41:31

help and some part

41:34

of the woman I love.

41:36

Okay.

41:36

Final one. This athlete

41:38

retired at arguably the height of

41:40

his career in nineteen ninety three. topping the

41:43

NBA and scoring for seven consecutive seasons and had been

41:45

named most valuable player three times. Oh, after

41:47

Is it Michael Jordan? because then he

41:49

came back. Yes. He

41:51

quit to play baseball. And then he came back, and

41:54

then he quit again. It's nice to meet you. love

41:56

them. You are so good, Annie.

41:58

I'm so glad I didn't quit any of

41:59

these anymore. I don't have

42:02

any

42:02

more for you, but you can come back and play

42:04

and we can just do a whole episode on this. Andy,

42:06

I'm gonna call this a three for three because you

42:08

just you know all the facts. You knew

42:10

everything, so you win this game. Andy,

42:12

let's leave things there. This is so fun. Thank

42:14

you for joining us on the podcast. We

42:17

appreciate it. Well, thank you for having

42:20

me. This is business casual, and

42:22

I'm Nora Ali. You can follow me on

42:24

Twitter at nora k Ali.

42:26

That's Nora, the letter K, Ollie.

42:28

And I would love to hear from you. If you

42:30

have ideas for episodes,

42:32

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42:34

love, fun segment ideas,

42:36

just shoot me a DM, and I will do

42:38

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42:40

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42:42

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42:44

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42:47

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43:14

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43:16

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43:17

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43:18

Business casuals produced by Captain Milsop, Olivia Meade, and

43:21

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