Do You Still Allot Time to "Little Bets" As Your Career Progresses?

00:00:00.000 | (upbeat music)

00:00:02.580 | - All right, moving right along here, Jesse,

00:00:09.640 | what do we got next?

00:00:11.040 | - All right, next up, we have a question from Joe

00:00:13.040 | and he's got a, he talks about little bets,

00:00:15.160 | a concept that you introduced in your book,

00:00:17.240 | "So Good They Can't Ignore You."

00:00:18.880 | - Hi Cal, this is Joe from the Midwest.

00:00:24.680 | I wanted to thank you for answering my previous questions,

00:00:26.920 | especially the one about getting, recognizing

00:00:30.400 | that we're going through a year of a dumpster fire

00:00:33.280 | and to spend the summer really chiseling away

00:00:35.880 | at the deep work and get a marine stove while I do it.

00:00:40.160 | Didn't get the marine stove,

00:00:41.360 | but I did spend the summer working on the big project

00:00:43.720 | and it was, it helps keep me sane.

00:00:46.720 | My question is about little bets.

00:00:50.160 | You mentioned in "So Good They Can't Ignore You"

00:00:52.260 | that you allot time to pursue little bets

00:00:56.560 | and you test them out on your blog,

00:00:57.920 | as short little blog posts,

00:00:59.600 | or you test them out in different ways.

00:01:02.120 | I'm wondering, as you get deeper into your career,

00:01:05.480 | do you still allot a significant amount of time

00:01:07.920 | for these little bets?

00:01:09.840 | For me, I'm very fortunate that I got my first book deal.

00:01:14.160 | I'm working really hard on that project

00:01:17.380 | and a couple of other really big rocks for my career,

00:01:20.560 | but I don't really see, short of Athena

00:01:23.640 | bursting out of my skull,

00:01:25.280 | how I can allot specific time just to pursue little bets

00:01:28.520 | when these other looming deadlines and big projects

00:01:32.840 | need my attention now.

00:01:34.200 | So if you could spend some time talking about

00:01:36.240 | what role does little bets take

00:01:37.880 | as you get deeper into your career,

00:01:39.960 | I think it would really help.

00:01:41.360 | Thanks.

00:01:43.000 | - Well, Joe, congratulations on the book deal.

00:01:46.260 | Shame, however, for not buying a marine pellet stove

00:01:50.840 | 'cause that is critical.

00:01:53.040 | That is critical to any deep work shed space.

00:01:56.120 | For people who don't remember this question,

00:01:58.200 | it was Michael Pollan.

00:01:59.280 | When Michael Pollan built a writer's shed

00:02:03.080 | in the woods behind his house in Kent, Connecticut,

00:02:06.160 | he heated it with a marine pellet stove.

00:02:09.360 | So it's like a pellet burning stove you put on a boat.

00:02:12.720 | So it generates heat, but it's like small,

00:02:15.320 | because it's main just for heating a boat.

00:02:18.360 | And so you put a pellet, marine pellet stove

00:02:20.700 | in your teeny house, and that's how you heat it

00:02:23.280 | while you look out over the snow strewn fields

00:02:26.340 | and the snow laden boughs of the birch trees

00:02:29.800 | in Kent, Connecticut, and have that warmth

00:02:32.840 | as you write in your cabin, wood line cabin.

00:02:36.920 | That's the vision.

00:02:38.640 | So yeah, you still need to buy that stove.

00:02:40.240 | I actually went out to Kent, Connecticut a few years ago

00:02:44.600 | and was doing a speaking gig out there.

00:02:46.200 | And it was like at a conference,

00:02:47.600 | like one of these conferences they used to do

00:02:49.040 | for rich people, basically.

00:02:52.840 | And the rich people come, and then a bunch of speakers

00:02:56.640 | and writers come and give talks and stuff.

00:02:58.120 | And the speakers and writers come

00:02:59.800 | because they want to meet the other speakers and writers.

00:03:01.420 | And then the rich people come because they want to hear

00:03:04.680 | from the speakers and writers.

00:03:05.920 | It's kind of a weird thing, but kind of a cool thing.

00:03:07.840 | And it was in Kent, Connecticut.

00:03:09.160 | So Michael Pollan was there because he still kept that house

00:03:11.800 | in Kent, Connecticut.

00:03:13.160 | And who else was there?

00:03:15.000 | Henry Kissinger was there, because he turns out

00:03:17.800 | to have a house in Kent, Connecticut.

00:03:19.520 | He's very old now, but he was there as well.

00:03:22.080 | But that was interesting.

00:03:23.120 | So that's when I learned like,

00:03:24.320 | oh, Pollan has the house here.

00:03:25.760 | And I can tell you, it's like a beautiful town.

00:03:28.200 | It has like this kind of fancy main street,

00:03:30.080 | and then it's all hills and trees.

00:03:31.560 | And I get why people flee New York to move to Kent.

00:03:35.280 | And so that's my Kent, Connecticut story.

00:03:37.700 | All right, but let's get back to Little Bets.

00:03:40.000 | So Little Bets was a concept I talked about

00:03:42.640 | in So Good They Can't Ignore You.

00:03:44.400 | It was coined by, I believe the author's name was Sims.

00:03:48.460 | Maybe Phil Sims?

00:03:50.340 | Yeah, I'm not quite sure.

00:03:51.740 | Do you have it, Jesse?

00:03:52.580 | You could look it up, right?

00:03:53.580 | - Well, Phil Sims is definitely a NFL quarterback.

00:03:56.000 | So I was just saying-

00:03:56.840 | - He's an NFL quarterback who also writes

00:03:59.580 | about business strategy in his book, Little Bets.

00:04:02.820 | All right, so probably not Phil Sims.

00:04:03.820 | Can you do like a Joe Rogan, Jamie thing here

00:04:06.420 | and see if we can find out?

00:04:07.820 | No, I feel bad.

00:04:08.660 | I feel bad that I'm using the wrong name.

00:04:11.820 | Anyways, I think the guy's name was Sims.

00:04:13.300 | I mean, this is a decade ago I wrote this book.

00:04:16.500 | But it was a self-explanatory concept

00:04:20.220 | of in your career, in your business,

00:04:23.260 | what you wanna try to do is take steps

00:04:27.340 | for which you can get feedback.

00:04:29.820 | And then you can see, and that can direct it.

00:04:31.460 | Oh, I get feedback.

00:04:32.300 | Like this isn't resonating, this is.

00:04:33.500 | So let me go that direction.

00:04:34.340 | Let me try a couple more bets.

00:04:35.540 | And by making sequential bets

00:04:38.780 | and making your future actions based on the feedback

00:04:42.940 | from those bets, you can actually have

00:04:43.980 | like an evidence-based way of guiding what you do.

00:04:47.820 | And this is better than he would argue

00:04:50.100 | coming up with a huge big plan in abstract.

00:04:54.580 | And then like, I'm gonna go execute this three-year plan.

00:04:57.180 | And I hope it goes well.

00:04:58.140 | So Sims was saying, take bets and get feedback.

00:05:01.460 | - John Sims?

00:05:02.580 | - Is it John Sims?

00:05:03.420 | That doesn't sound right.

00:05:04.420 | Can you find the book, Little Bets on?

00:05:08.260 | - I'll look for it.

00:05:09.100 | - Yeah, like Amazon or something like that.

00:05:10.940 | If it is Phil Sims, that'd be awesome.

00:05:13.340 | If the quarterback was writing that book.

00:05:17.780 | - Phil Sims is on Mad Dog every Friday.

00:05:19.500 | I love that spot.

00:05:21.180 | - Okay, so Phil Sims is on Mad Dog every Friday

00:05:24.660 | talking like Harvard Business Review style career strategy.

00:05:29.260 | Like Mad Dog, let me talk to you about getting feedback

00:05:32.540 | from the right market segments on your consulting firm.

00:05:35.540 | So Joe, I mean, I think the key thing to take away

00:05:38.980 | from Little Bets is-

00:05:41.460 | - Peter Sims.

00:05:42.420 | - Peter Sims.

00:05:43.740 | I was close.

00:05:44.580 | - Yeah.

00:05:45.420 | - Yeah, Phil Peter.

00:05:46.260 | Peter Sims, little known fact, younger brother

00:05:48.660 | of NFL quarterback Phil Sims.

00:05:50.620 | I'm just gonna put that out there.

00:05:52.340 | Just gonna declare that.

00:05:54.420 | So the feedback's what's key.

00:05:57.740 | So Joe, the feedback's what's key, right?

00:05:59.660 | And so I'm thinking about your situation.

00:06:03.100 | Yeah, at some point, as you get feedback

00:06:05.740 | and you move along, you get to the place

00:06:07.220 | where the steps are pretty big.

00:06:08.340 | But if you're thinking about a book,

00:06:09.580 | you're writing a book now,

00:06:10.420 | but how did you come to write that book?

00:06:11.700 | Hopefully there is a sequence of Little Bets

00:06:13.900 | where you are finding these ideas, what resonates,

00:06:17.300 | what seems to have an audience.

00:06:18.860 | And so you have this clear feedback before you actually go

00:06:21.500 | to the stage of writing a book about it.

00:06:23.100 | I think that's a clear example.

00:06:24.300 | I mean, take something like my most recent book,

00:06:26.340 | "A World Without Email."

00:06:27.740 | How many years can you go back

00:06:29.220 | and hear me talking about these things?

00:06:31.180 | When you can go back and like my first appearance

00:06:34.140 | on the Ezra Klein podcast years ago,

00:06:37.340 | I'm working through a bunch of the core ideas

00:06:39.620 | that became "A World Without Email," right?

00:06:41.620 | Years before.

00:06:42.660 | How many articles that I write?

00:06:44.580 | There's actually an article I wrote

00:06:45.900 | for the Harvard Business Review to promote deep work.

00:06:49.740 | So all the way back in 2016,

00:06:52.620 | that was about getting rid of email

00:06:55.380 | and working through some concepts

00:06:56.700 | that made their way into the book.

00:06:57.760 | So years of why workout concepts in my Little Bets,

00:07:00.500 | or I write about them, or I talk about them on this podcast,

00:07:02.840 | or I talk about them on other podcasts,

00:07:04.260 | or I write articles about them and I see what the response is.

00:07:08.100 | So like I'm thinking now I might write a book

00:07:09.700 | about slow productivity.

00:07:10.860 | I've been testing out this idea.

00:07:13.580 | I wrote a New Yorker piece about it,

00:07:14.900 | got some pretty good feedback that was useful.

00:07:17.640 | I did a podcast video about this, a core idea video

00:07:20.860 | that was useful.

00:07:21.700 | I talked about it on Tim Ferriss' podcast.

00:07:23.980 | And I could see when he split up that interview

00:07:26.780 | into segments, he did a clip

00:07:28.640 | of the slow productivity discussion,

00:07:30.220 | and that's the most viewed clip

00:07:31.300 | of all the clips he did from the podcast.

00:07:34.820 | That's feedback on this.

00:07:35.820 | So those are Little Bets that are helping me put together

00:07:38.020 | what I wanna do, and at some point

00:07:39.260 | I'm gonna write a book about it.

00:07:40.140 | So Joe, I would say that's the takeaway message

00:07:42.060 | is you wanna get real feedback from people,

00:07:45.460 | not people like friends, but actual unbiased feedback.

00:07:48.060 | Are you buying this?

00:07:48.900 | Are you paying for this?

00:07:49.720 | Are you giving me money?

00:07:50.560 | And allow that to help direct you

00:07:51.900 | towards which direction you go.

00:07:53.020 | But I think you're absolutely right to point out

00:07:54.780 | that a Little Bet strategy will eventually lead you

00:07:58.340 | to really big things that take time.

00:08:00.900 | You do a lot of bets on topics,

00:08:02.540 | you might then end up spending two years writing a book.

00:08:05.580 | Do a bunch of little bets on a product,

00:08:07.780 | you might end up at some point taking on investment

00:08:09.700 | and going all in on a business.

00:08:11.020 | And that's a multi-year commitment one way or the other.

00:08:13.100 | So that's true.

00:08:13.920 | Little Bets lead to big commitments,

00:08:15.380 | but the key is not to jump right into that big commitment

00:08:18.760 | just because you hope or you have a reasonable story

00:08:22.820 | about why what you're gonna do would be useful,

00:08:24.420 | that you actually have some evidence.

00:08:28.220 | And if you doubt that, talk to NFL quarterback, Phil Sims.

00:08:32.140 | He will fill your ear.

00:08:34.140 | He will fill your ear with thoughts on Little Bets.

00:08:39.020 | - All right, that's a blast for the past.

00:08:42.020 | So Good They Can't Ignore You was 2012.

00:08:45.100 | So yeah, we're at the 10-year anniversary.

00:08:47.880 | Interesting.

00:08:49.620 | That's when I kicked off my writing career

00:08:54.220 | as a non-fiction idea book writer.

00:08:57.140 | I wrote these three books for students.

00:08:59.060 | That's how I got my sea legs,

00:09:00.740 | that's how I built up my craft.

00:09:01.880 | And So Good They Can't Ignore You

00:09:02.940 | was the vision I had all along of,

00:09:05.060 | I wanna write idea books, non-fiction books,

00:09:07.220 | Table at Barnes & Noble, On NPR, New York Times articles.

00:09:12.060 | That's what I wanted to do.

00:09:13.540 | And that's where I kicked off that transition.

00:09:15.340 | So it's a really important book for me.

00:09:17.220 | It was the first time someone said,

00:09:18.260 | "Okay, you're allowed to write a hardcover book

00:09:21.580 | "about an idea, it's a crazy thing.

00:09:24.420 | "Just an idea you made up.

00:09:25.920 | "And you can just put that in a book

00:09:29.520 | "and we'll see what happens."

00:09:31.140 | So that was definitely a big transition for me.

00:09:34.380 | - That's a cool story.

00:09:35.300 | - Yeah.

00:09:36.460 | And it was good, that book went to auction.

00:09:38.700 | And at the time it seemed like a lot of money.

00:09:41.340 | It's how we bought our first,

00:09:42.740 | it was the down payment for our first house

00:09:44.860 | and how we bought our first car

00:09:47.300 | as we came out to Georgetown.

00:09:48.980 | Because that book was really,

00:09:50.540 | I wrote it right before I came out here.

00:09:52.060 | And it came out right after I got here, it's my memory.

00:09:56.100 | My memory is right after I got to Georgetown it came out.

00:09:57.980 | But I wrote it as a postdoc.

00:09:59.620 | So it was exciting, it was some money

00:10:01.460 | and not like life-changing money,

00:10:03.540 | but bigger by far, like factor of five bigger

00:10:07.540 | than I was getting for the student books or whatever.

00:10:09.220 | And then it didn't do well out of the gates.

00:10:13.340 | So there's a story in that.

00:10:14.700 | There's a big push, we hired a good PR company

00:10:21.500 | and it just kind of disappeared.

00:10:26.260 | We're like, "Oh man, I guess."

00:10:28.380 | 'Cause I didn't know how publicity,

00:10:29.620 | I had no idea how book sales work.

00:10:31.020 | I still don't know how that works.

00:10:32.060 | And it's like, "Okay, I guess,

00:10:34.100 | "do I get to keep doing this?

00:10:35.220 | "I don't know."

00:10:36.140 | And so I pitched them deep work finally into like,

00:10:37.780 | "Yeah, but we're gonna pay you less money,

00:10:39.100 | "but if you wanna write it, go ahead."

00:10:41.180 | And it was just a funny thing.

00:10:42.220 | It's just good ideas are good ideas.

00:10:44.580 | And it took years, but then it just,

00:10:46.620 | it picked up and sold hundreds of thousands of copies.

00:10:50.620 | But it was, it seemed like a dud out of the gate.

00:10:54.260 | And I'll say the two things that seemed to matter

00:10:56.540 | was podcasting came along

00:10:58.660 | about two years after I wrote that book.

00:11:01.180 | So I wrote that book,

00:11:02.140 | I did a thing for the New York Times

00:11:03.780 | and like it got a good,

00:11:04.860 | there's a few things I did,

00:11:06.380 | it kind of disappeared.

00:11:07.420 | And it's some radio, but some stupid radio.

00:11:10.140 | And then starting around 2014,

00:11:11.620 | podcasting became a thing.

00:11:13.580 | And so I became, I was like a very early guest

00:11:16.460 | in podcasting circuits,

00:11:17.780 | doing a lot of these early podcasts.

00:11:19.820 | And I just did a lot of podcasts,

00:11:21.740 | like why not?

00:11:22.580 | I thought it was fun.

00:11:23.420 | And I think that built the slow burn.

00:11:25.980 | If there for like 2014 to 2016,

00:11:28.060 | I was on a lot of shows.

00:11:29.340 | And that's how I got kind of good at it

00:11:30.820 | because I was doing podcasting really early on.

00:11:33.100 | And I sort of learned the medium.

00:11:34.220 | And I think that's what really,

00:11:35.140 | two years after it came out,

00:11:36.300 | started that burn.

00:11:37.180 | And then Deep Work did something similar,

00:11:39.340 | but its burn was much more intense.

00:11:41.180 | Like that book sold a lot of copies.

00:11:42.580 | And I think that also just pointed people back

00:11:44.980 | towards that original book.

00:11:45.980 | So that's how it all got started for me.

00:11:47.380 | I was, got real excited,

00:11:48.660 | got this deal, got this book,

00:11:50.580 | it disappeared,

00:11:52.020 | thought that I'd be done with publishing.

00:11:53.980 | And then podcasting came along

00:11:55.620 | and Deep Work came along.

00:11:56.540 | And that's actually like a,

00:11:57.380 | turned out to be a very successful book.

00:11:59.260 | - The other thing too,

00:12:00.100 | you talk about and others talk about is,

00:12:01.980 | you have, you had another job too.

00:12:04.300 | So you weren't relying on that to survive.

00:12:06.460 | So I mean, you could like give it some time.

00:12:08.580 | - Yeah, exactly.

00:12:09.460 | I don't, it would have been harder if I was,

00:12:10.940 | well, what happened in the nonfiction space.

00:12:12.340 | - Much more stressful.

00:12:13.500 | - And you have to become like a super speaker.

00:12:16.620 | That's what was happening back then.

00:12:18.380 | If you were trying to make a living

00:12:19.860 | off of nonfiction advice books,

00:12:21.460 | you had to be doing 30 to 50 speeches a year.

00:12:25.460 | And like what a lot of writers would do in that space.

00:12:28.620 | And it's very lucrative by the way,

00:12:30.820 | but it's tough.

00:12:33.380 | But a lot of writers would just do year on year off.

00:12:36.620 | So like 50 speeches, killer.

00:12:39.260 | And then a year writing,

00:12:40.460 | then 50 speeches a year writing.

00:12:41.740 | And you always had to have the book came out.

00:12:43.220 | And then your whole life is built around the speaking.

00:12:45.380 | So fortunately I was a professor

00:12:47.140 | and so I didn't have to do that.

00:12:49.460 | I could just say, I don't know,

00:12:50.340 | I guess this book didn't do well.

00:12:51.220 | I waited a long time.

00:12:52.060 | That book came out in 2012.

00:12:53.460 | And then I didn't,

00:12:54.300 | Deep Work came out four years later.

00:12:56.300 | So I was having kids and trying to get tenure.

00:12:58.980 | And so that was kind of a fun time actually.

00:13:00.340 | I mean, there's something innocent to it.

00:13:01.380 | I would do, it was entirely homegrown.

00:13:03.860 | This is the way I remember it.

00:13:04.940 | Is like I would do podcast in my basement and that was it.

00:13:09.940 | And then at some point I started writing Deep Work

00:13:11.580 | just sort of on my own and that was it.

00:13:13.780 | And then everything else was just organic.

00:13:15.500 | And so that's my view.

00:13:17.500 | If a book is right,

00:13:19.100 | it will eventually sell a lot of copies

00:13:21.100 | regardless of what happens early on.

00:13:24.060 | I don't know how to make a book

00:13:25.260 | sell a lot of copies right up front.

00:13:27.220 | I've never been able to do that.

00:13:28.820 | - It's kind of like what the book says.

00:13:31.660 | It's so good you can't ignore you.

00:13:33.100 | So if like the book is good,

00:13:34.900 | it can't be ignored.

00:13:35.820 | - Yeah, I don't think anyone knows.

00:13:36.780 | Like my editor, I love the editor on that book.

00:13:38.380 | He's like, this is a great idea.

00:13:39.460 | Like this, and he was right in the end,

00:13:40.860 | we sold a ton of copies of that book.

00:13:42.740 | But he was like baffled.

00:13:43.700 | He's like, why aren't we early on?

00:13:45.940 | Why isn't, why is no one buying this?

00:13:47.660 | It's such, I just don't think people understand

00:13:49.460 | or they don't understand the degree to which

00:13:51.500 | like email lists, these other types of dynamics

00:13:53.540 | and cultural, your cultural awareness.

00:13:56.580 | Like this stuff plays a huge role

00:13:58.380 | in things like taking off right out of the back.

00:14:01.380 | But it's almost like that's orthogonal

00:14:02.780 | from whether or not the book is gonna be.

00:14:06.060 | So we'll see, we'll see.

00:14:07.500 | But it was a cool story.

00:14:08.380 | So that started that whole chapter of my life,

00:14:10.300 | which was, that was an interesting one.

00:14:13.220 | (upbeat music)

00:14:15.820 | (upbeat music)

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Do You Still Allot Time to "Little Bets" As Your Career Progresses?

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