When to Say "Yes" to A New Project

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like, we have to start from scratch. I'm Jason Pfeiffer, the Editor-in-Chief of Entrepreneur Magazine.

2:01Entrepreneurs don't die of starvation. They die of indigestion. I've heard this line from a number of people and really love it because it's just so true. The idea here is entrepreneurs never have too few things to do. We have too many. We take on too much, try to shove too much in our mouths. And as a result, we can't fully chew and swallow any of it. This is actually now I'm torturing the metaphor with starvation and indigestion. But whatever. Anyway, you get the idea here, taking on too much. I'm sure you feel it. I certainly do. And it's a balance that I struggled even to articulate right now because I know that if I take on a new project, I am robbing other projects of my time and energy.

2:49And that we need to be focused in order to make something succeed. And yet, to be an entrepreneur is to be endlessly curious, to desire to explore and to expand. And therefore, there is this question that we need to take very seriously, which is, when do I say yes to something? When do I truly take something new on? That's what we're going to be talking about today because I got to talking about it with a very accomplished guy I've become friendly with who is very busy, stretched very thin, and recently decided to say yes to something new for reasons that may sound a little surprising. So let me introduce him.

3:34My name is Dan Heath. I am the author and co-author of five different business-ish books, made to stick, switch, the power of moments, and a couple more. Dan also teaches, he speaks, he works with entrepreneurs. He does a lot. And yet recently he decided to take on a new project. It's a podcast. And now I know what you're saying. Oh my God, everyone's got a podcast. Jason, you've got a podcast. You've got two of them. It's true, I do have another podcast called Help Wanted. Anyway, yeah, Dan did not just make any podcast. He made a very high quality, very labor intensive podcast. It's called What It's Like to Be.

4:13Where in every episode, we interview someone from a different profession, like a mystery novelist and a cattle rancher and a turnaround consultant. And then they have these wonderful, insightful conversations about what it's like to be that person. Not just what do they do every day. What does it feel like? And where do they derive their joy? And how do they learn to do the hard and overlooked parts? And that kind of stuff doesn't just come because you wing an interview. No, just to be clear. I do a lot of prep in advance. And so I've got a Google Doc full of questions that I think I might want to ask.

4:52And then inevitably, I'll ask five of the 80 questions in the document and then just follow the conversation where it leads. And then we edit that down to a pretty tight, like 30-minute-ish episode. From an original 90-minute recording. Anyway, I say all that just to show you that as a guy who's writing bestselling books and doing all these other things, to take on a project that takes a lot of time and thought and energy is no small feat. You don't do that on a whim. And Dan is so incredibly thoughtful about how he spends his time that I wanted to have this conversation with him about how does he decide when to say yes to something new?

5:37because if you're not being thoughtful about it, then you're going to die of indigestion. Yeah, this is something I agonized an awful lot about. And it's a familiar predicament. As a writer, first and foremost, one of the chief kind of gates that I'm perpetually going through is this idea that I have right now enough to write a book about. Do I feel comfortable throwing three or four or five years of work at this idea. And I have a lot of ideas and most of them are dumb or most of them are fleeting. And one of the things I've learned over time is the first pass filter is how long does the idea hang around?

6:18And this idea for the podcast, the idea of interviewing people from different professions, really asking them lots of nosy questions about their work, trying to understand something about what it's like to walk in other people's shoes. It just kept hanging around. And so that's the first kind of proof to myself that there's something here, at least for me. And I really like that, by the way, as a way of thinking, because you don't jump immediately at something, but you let it linger. And most of the ideas that we have or the impulses that we have, they fade. And the ones that stick, maybe that means that we're using ourselves as a filter for what excites us and could excite others.

6:57And that is just the start. Dan is so incredibly thoughtful about how to take on projects and how to use time and how to say yes and how to say no. And that is the conversation that we're having today on Problem Solvers. So today it is Dan Heath, host of What It's Like to Be. And we're going to talk about what it's like to be a guy who said yes to a new project. Coming up after the break. We all want the best of both. Dessert without calories, luxury without expense. And how about security without passwords? With Okta, It's possible. We secure identity for your business so you can safely use any technology.

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8:26That's marketplace.walmart.com slash solvers. Head over and get started today. All right, we're back. I'm talking today with Dan Heath, host of the podcast, What It's Like to Be, about what it's like to be someone who says yes to a new project and what does it take to become that person so that we don't stretch ourselves too thin, but instead focus only on the new things that really matter. And just before the break, Dan said, one of the things that he does is he watches for which ideas are stickiest with him. But the way in which he makes these kinds of decisions goes far beyond that. I just set up a series of tests for myself.

9:10I'm curious if you've done some of the same things. The first for me was just, it was a smell test for me personally. It wasn't, I wasn't even to the point of a market test or minimum viable product or anything, but I just had a couple of conversations. I asked the guy who cuts my hair, it'll be a guinea pig. And so I had a friend who produces podcasts to tutor me through the process. And we had a conversation and I just thought it was a hoot. I remember this moment when he told me about he has this thousand dollar pair of Japanese scissors and I got him talking about how can scissors be so expensive and what do they do that the pair of scissors in your kitchen drawer won't do.

9:47And I remember the producer afterwards was saying, you got really excited about that thing about the scissors. Like, why were you? And so anyway, she was a little puzzled by my reaction. But for me, it was like confirmation. Like, I love talking about this stuff. And so that was the first gate. Yeah, I think that's a really useful way of thinking about things. First of all, that you just waited to see whether or not the idea stuck around long enough because you to devote yourself to this project would need to be really committed to it for a long time. So it better be something that feels good to carry around for a while.

10:27And the great thing is there's no tax, there's no personal tax on letting an idea sit in your head and just seeing how it feels. That's one thing we really can just commit ourselves to infinitely is how many ideas do we carry around and how many of them excite us enough that they're still there even if we weren't trying to keep them around. And then number two, what it reminds me of when you were saying, you just tested it out to see how you felt about it. I have this personal policy of it's always taking the call, which is that if any interesting opportunity comes along, I at least will take the phone call about it.

11:07And the reason for that is because what I found is that oftentimes I take the call and I walk away saying, I don't want to do that at all. I'm really happy that I'm not going to commit myself to that. But if I hadn't taken the call, maybe I would have wondered. Maybe I would have felt some kind of longing. There was a time where I thought I should be a venture capitalist. And a guy was like, I'll connect you with a venture capitalist. And so I had a whole conversation with him about what it's like to do that. And at the end, I thought, I don't want to do that. And I'm so happy that I spent time exploring it so that I know I don't want to do it.

11:38But occasionally, you come across something that excites you. And that's at least worth exploring, isn't it? Amen. And I'm thinking of lots of times in my life when I've done the sample thing and figured out very quickly, oh, this isn't for me. I had this whole story in my head that turned out to be a fantasy. I don't want to do that at all. And it feels wonderful even to get to a no in those situations because it's like you've saved yourself a ton of time. Yeah. It's a real gift to yourself in a way to explore things, knowing that you don't have to commit to them all. So did you, once you decided to do this, did you do some kind of time audit or did you say to do this is to not do that or here is where that time is going to come from?

12:22Are you that intentional about how you add projects to yourself? It's the short answer to that. It sounds wise as you say it and now I'm like taking a note to myself, do a time audit on a project. I guess I, this project came about at a fortuitous time because I was in like a research cycle for a book and research cycles for me fit the available time because it's me that's driving the pace. And so I knew that I could accommodate this if I wanted to. And so I just jumped in and I thought, hey, the first thing I've got to do honoring the lean startup Eric Ries spirit is, is I've got to just crank out some real episodes.

13:01Like the thing with the guy who cut my hair was just like us getting on Zoom and talking. So that's not a thing. I wanted to make a quality episode, something I thought people might sit through and then find some people to listen to it. And so that was like the next big leap forward for this project. And that meant finding a producer because I knew I didn't have any of the technical chops, none of the industry knowledge, none of the creative knowledge needed to do this. I just had what I thought was a good idea. And I wanted to be the person doing the interviews. And so that was an interesting experience in and of itself.

13:33I imagine your listeners have been in the situation of needing to hire someone with a set of skills that you're not really qualified to assess. I remember from my days with a startup, having to hire an IT director knowing nothing about IT. And so it's this weird dance. And I tell you what, one of the ideas in an old book of mine that I wrote with my brother Chip called Decisive is the idea of ooching, meaning take small steps, test things out, sample. And so I tried that. I had two producers that I'd interviewed and just stellar backgrounds. I loved both of them. I love their past work. I was having a really hard time deciding who to run with.

14:16And I remembered my own advice from Decisive. So I was like, OK, I'm going to set up a job sample here. I'm going to have them like find find a candidate for the show, produce the episode, do the whole thing that they're actually going to do. So instead of just talking to them on Zoom and seeing if they answer questions like a good producer would, actually have them do some producing. And I tell you what, when I did that, I basically hired them both for a month to do a producer's job in a freelance fashion. And it was just, it was such an easy decision at the end of the month. I felt Matt, the guy who's producing the show now, was so talented, so into it.

14:55I felt like he had a real natural enthusiasm for the project. We worked well together. And it was like it went from a really hard decision to a really easy decision. So that was one of the few things I feel like was really wise in this whole process, was getting my number one collaborator to simulate the work that we would do together. What's interesting about that strategy and the way it's executed is it pulls something from outside of your area of expertise into your area of expertise. Because you don't know anything about podcast producing when you're first hiring a podcast producer, right?

15:32You're talking to these folks and they're doing a thing that you're unfamiliar with. So how could you evaluate them, as you just said? And they could tell you all about podcast producing and it all sounds good to you. There's no way to evaluate it. So how do you evaluate it? If you have them do some work, then you start to evaluate things that are very familiar to you. What is it like to work with this person? Do I jive with this person? Do we share a similar sensibility or do they add something that I feel like I'm missing? Those are human things that you know how to evaluate no matter the task and no matter the discipline.

16:07And that makes you an expert in something so that you can make a more expert decision. Yeah, it's like it brings my judgment back online. Like when I can hear the audio he produces, like I have insight there. I know what a good story sounds like. And I know, you know, what the telling details were. And so, yeah, I feel like I can engage with that in a way that if it was a technical test of editing software, like I'm completely lost. It's something I have always thought about for myself when I add new projects and hearkening back a little bit to when I asked you if you've done a time audit, which I said that like I do time audits.

16:52I will admit to you, I do not. But I have this philosophy that is almost maybe the opposite of a time audit. I'm just going to share it with you and see what you think about it, which is my philosophy is that time expands under pressure. And what I mean by that is that when you add something else to your list of things to do, it forces you to reconsider all the other ways in which you spend time, which you wouldn't have otherwise done. We almost never do that kind of calculation for ourselves unless we're forced to because otherwise, why spend the time? And so when you commit to something new, it forces you to say, okay, this other thing that I'm doing, am I doing it in the most efficient way possible?

17:42Do I need to still be doing that other thing? Maybe there's another person who I can bring on to that project and it'll help me. And in doing so, time expands under pressure. You are able to do more with your time because you created more pressure for yourself. And that is maybe my excuse for just saying yes to too many things, but I've also found it to be largely true. I'm curious if you found that to be the case for yourself, if taking on this one project helped you think through how you spend time anywhere else, or if you just found a wedge and you shoved it in. No, I have definitely experienced the same thing, that squeezing something else into your schedule forces this automatic triage process where all the other stuff just gets reshuffled in a useful way.

18:33And I think, I think that's true for me up to a point. And I don't know exactly how to specify what that point is, but I think at a certain threshold, I start to feel like a slave to my commitments in a way that, that I really don't like psychologically. Like I think I'm a, I am definitely not a workaholic type. I'm more of like, I want to have space to sit under a tree and think and reconsider and navel gaze a little bit. And I think it just manifests as when I'm feeling perpetually stressed, perpetually behind the eight ball, that's my cue. Something's got to get cut. It's really good to know where your own ultimate goals are because you could fill your time with endless opportunities, I'm sure.

19:17Dan, you probably say no to things all the time that people are reaching out about. A hundred percent. And I've gotten a lot more disciplined about that over the years. In the early days, it was just there was so much stuff coming over the transom. My brother and I had written a book called Made to Stick, and it was an unexpected hit. We were more surprised than anyone else, I think, that it did as well as it did. And so all of a sudden, opportunities just start getting thrown over the transom. And I'd never experienced anything like that before. And there was just like a lot of shiny object chasing in those days and conversations that led nowhere.

19:53projects that I should have known from the outset were pointless, just indulged too long. And so I just kind of practiced the art of trusting my intuition, what has promise and what doesn't, and just be ruthless. Because when your schedule is full, the marginal project, the marginal idea starts cutting into personal life and family time. And then that was just too much for me. Yeah, I was just reading Lenny Richisky's newsletter. I'm not sure if I know how to pronounce his last name, but anyway, Lenny's newsletter. And he had written a newsletter about saying no and all the different ways that he has learned to say no.

20:30And one of the ones I loved the most, which what you just said there reminded me of was to outsource, outsource the evaluation to someone who can look at it a little more objectively or who maybe is more protective of your time than you are. So he finds, for example, that he'll, if he doesn't know whether not to say yes or no to something. He just asks his wife, who will look at it from a different perspective, which is this going to take more time away from family? Is this something you actually are going to be fulfilled by? And someone else doesn't have the same shiny object syndrome that you do.

21:07And I do this a lot too now, especially with my classic thing is speaking engagements that don't pay my full fee, but that I still want to do because I just like the travel and the speaking. and so I'll go and I'll ask my wife, hey, they want me to fly to California and they offered this much. Should I do this? And she will say, no, don't do that. Because what she's thinking is, no, because you're going to be away and I got to deal with the kids myself. And I totally respect that. And so sometimes just asking someone else, especially someone whose time is tied to your time is a really great way of dilating.

21:40Here's something that literally none of your listeners are going to care about, but you will, that I found useful for, because I do a lot of speaking engagements as well. And I've come up with this thing that I call a bedtime quota, which is I negotiate with my wife like a number of bedtimes that I'm going to be away from the family on an annual basis. And that's like the chips that I have to play with. And I found that it makes me much more like strategically ruthless about I'm on the East Coast. And so if it's a California thing, I'm not going to burn two bedtimes on that thing that doesn't pay well.

22:14and it's not an audience I particularly care about. And it's just, it's made it a lot easier for me to be clear eyed about the trade-offs involved. I actually really love that. Just to belabor it one more moment, because I don't know how many people this is relevant to. Do you set a, really a specific number of bedtimes? Like at the beginning of the year, do you have 20 bedtimes or whatever it is? Oh, wow. That's so smart. And then I just buy that down over the course of the year and I get more liberal or more conservative as the year. emerges and I see what the demand is like. That's great. But like what you were talking about before, it's like a forced triage.

22:52That's like an artificial way to force yourself to trade off better and worse opportunities. Yeah. All right. Last way to look at this question of should I be doing this, which is that you've done it and now you're evaluating whether or not to keep doing it. You were telling me before we recorded, but I don't actually know what you're going to say here, which is that you have, you set a couple benchmarks. You set a couple goals. You've reached some of them, not some others. I'm curious how you structure that in your mind, what you're looking for as you continue to evaluate whether or not something is continually worth your time.

23:30Yeah, yeah. It's fun that we're talking now because I certainly don't mean to imply that like there's not like an unveiling where we're going to say the show's a massive hit. It's not yet. It may never be for all we know, but it's like, where I'm in the second quarter of this really interesting project. And I've passed a number of tests that I set for myself, but there's a bunch more to come. So like one of the tests that I think would be relevant for almost any business proposition was, I didn't want to do this podcast unless there were people who loved it. As distinct from this pitch of walking in other people's shoes, you can see how that would be intellectually interesting.

24:08My worst fear was that it would feel like a show that was good for you, eating your asparagus. Oh, I should listen to that show. I should increase my, I did not want to do the asparagus show. And so that was the first like market facing test that I was really curious about is, are there people out there who will think this is cotton candy and not asparagus? And just recently the audience numbers have been building, which is good, but I feel like I really officially passed that test in my own brain recently, we did an audience survey and it was just so heartening to hear people say, I listen to this the moment it comes out and you should speed up the pace.

24:49Like that's what you want your audience to say back to you and people that had listened to every episode. And I was like, okay, all right, check. There are people in the world who really dig this. That doesn't mean it's a viable business. That doesn't mean I'm going to be doing it in five years, but that's a critical test, right? Someone cares about this. And really worth asking because what you don't want to do is blindly continue on something just because you happen to love it and not really have the curiosity or maybe the stomach to discover if other people really feel the same. Yes. And I was really, I was terrified that I was going to rationalize away to myself because I care about it so much.

25:27That's always a dangerous thing in business. It must be nice to sell cheese graters or something where you just don't give a damn. Like you just want people to buy the cheese grater. Something like this that's creative where you're pouring some of yourself into it where I feel like I'm trying to triangulate between what's important to me but also what the audience wants. And neither one alone is sufficient. Like I don't want to just make something for myself. That feels lonely and pointless. But I'm also not in the business of maximizing clicks or listens. If I were doing that, I'd just make a true crime podcast.

26:01because that's what the world wants. That's the empirical proof. I think the triangulation is part of the fun. And so looking ahead, I think the next real challenge for the podcast is, okay, there are people in the world who dig this. We know what their profile is from some of the market research. And now the question is more of an economics question, like how much does it cost to identify more people like that and bring them to the show? Because it's the kind of thing where if it costs you$50 to attract a listener that's only worth$10 on an annualized advertising basis or whatever, that's not a great business model.