How Constraints Make Us More Creative

Summary

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Podcast Summary: How To! with Mike Pesca

Episode: How Constraints Make Us More Creative
Date: June 30, 2026

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Episode Overview

In this episode, host Mike Pesca is joined by listener Ofra Obejas—recently retired and wrestling with too many creative options in her newfound free time. The episode delves into the paradoxical power of constraints for fostering creativity and focus, drawing on insights from bestselling author and previous How To! host, David Epstein (“Inside the Box”). Ofra’s real-life conundrum—how to channel her varied interests (from writing to comedy to gardening) into meaningful creative output—serves as the case study for applying the episode’s advice.

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Key Discussion Points and Insights

1. Introducing Ofra’s Creative Dilemma

[01:49 - 04:31]

• Ofra, a retired psychotherapist (with a background in homeschooling and computer coding), is excited to finally pursue deferred creative projects: cooking, gardening, painting, stand-up comedy, and, notably, writing a book.
• She enjoys exploring new activities, but feels unfocused—struggling to choose where to commit her time.
• Writing a book stands out as a long-standing goal, yet she’s unsure how to start or prioritize it amid abundant options.

“I cannot say no to one in order to focus on another.”
—Ofra, [04:21]

2. Digging Deeper on Commitment and Enjoyment

[04:49 - 05:41]

• Ofra distinguishes between pursuits she’s happy to “just try” (like painting), and those she deeply wants to develop (writing, humor).
• She has dipped her toes into performing stand-up and finds fulfillment in making an audience laugh.

“I just wanted people to have a good time. And they did.”
—Ofra, on her five-minute stand-up set, [06:44]

3. Introducing the Creativity Expert: David Epstein

[11:40 - 12:31]

• David Epstein, author of Inside the Box, joins to discuss the counterintuitive value of constraints in creativity.
• He outlines the main thesis: people overvalue complete freedom and underestimate the power of useful constraints for focusing, unsticking, and channeling creativity.

“We overvalue complete freedom in the abstract and undervalue useful constraints, even though they can be our most powerful tools for focusing a project, unsticking yourself, or just figuring out where to apply your energy.”
—David Epstein, [12:31]

4. The Myth of Freedom Equals Creativity

[13:05 - 15:11]

• Epstein notes a widespread (but false) belief that more freedom leads to more creativity; research shows the opposite.
• Many people fall into the trap of maximizing (or “optimizing”) constantly, leading to indecision, regret, and lack of satisfaction.

“Preserving optionality has become an end to itself... It’s the illusion of keeping your options open, even while they’re closing.”
—David Epstein, [14:02]

5. Exploration vs. Commitment

[15:59 - 17:34]

• While exploration is valuable for discovery, at some point, focus and commitment (a constraint) are essential for producing meaningful work.
• Epstein references research showing authentic achievement tends to come after an exploratory period is followed by a focused “hot streak.”

6. Retirement and the Loss of Natural Constraints

[17:34 - 19:54]

• Epstein discusses retirees’ struggles with opportunity overload and the sudden loss of structured time.
• The lack of external “have-to’s” breeds overwhelm, requiring self-imposed constraints to regain productivity.

“Like the great Duke Ellington said, ‘I don’t need time, what I need is a deadline.’”
—David Epstein, [19:54]

7. Practical Tactics: Imposing Constraints

[19:54 - 21:52]

• Tactics include:
  • Listing and prioritizing all commitments (e.g., with Post-it notes).
  • Deciding what to cut.
  • Acknowledging the “additive bias,” our natural tendency to take on more rather than subtract.
• Epstein suggests starting with small, clearly defined projects or parameters.

8. Applying Constraints to Ofra’s Book Project

[24:45 - 28:59]

• Epstein shares the “Tony Fadell method”—writing a press release before even beginning a project to force clarity on:
  • What’s the problem you’re solving?
  • Who is it for?
  • What do you want the end result to be?
• He encourages Ofra to test her ideas in low-stakes formats (Instagram Reels, Substack) to refine her voice, message, and medium with tight word/time limits.

“I’m a huge fan of low stakes practice. How can you test something in as small a way as humanly possible?”
—David Epstein, [27:00]

9. Audience Feedback vs. Personal Practice

[32:50 - 33:05]

• The primary value of Substack or Instagram is in giving the creator structure and a routine, not necessarily audience validation.
• Regular, constraint-based “output” breeds momentum and makes starting each day psychologically easier.

10. The “Hemingway Principle” and Daily Habits

[31:03 - 31:58]

• Inspired by Hemingway, Epstein suggests ending each work session with a note about exactly where to begin the next day—reducing the temptation to default to trivial tasks.

“The last thing of each day is… write down where am I starting tomorrow?”
—David Epstein, [31:44]

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Concrete Next Steps for Ofra (and Listeners)

[35:43 - 37:02]

• Assignment: Write a one-page “press release” for the book, including hypothetical reviews (both glowing and negative).
• Action: Break the book idea down into single anecdotes or concepts; try them out as 800-word Substack posts or short video reels.
• Schedule: Use self-imposed deadlines and regular output to reintroduce structure.

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Notable Quotes & Memorable Moments

• On maximizing and happiness:

  “Maximizers tend to be less happy with their decisions, less happy with their lives, much more prone to regret…”
  —David Epstein, [14:26]

• On structure and productivity:

  “When I was a college athlete...when I did the best academically was when I was in season because I was so structured.”
  —David Epstein, [17:52]

• Ofra’s comedic gem:

  “In his defense, my husband is one of those immigrants who took a job no American wanted. Being married to me.”
  —Ofra Obejas, [07:12]

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Timestamps for Key Segments

• Ofra’s creative dilemma introduced: [01:49 – 04:31]
• Ofra discusses commitment levels for hobbies vs. passions: [04:49 – 05:41]
• Introduction of David Epstein and Inside the Box: [11:40 – 12:31]
• The myth of freedom and the role of maximizing: [13:05 – 15:11]
• Constraints, prioritization, and behavioral tricks: [19:54 – 21:52]
• The “press release” constraint method and trying new formats: [24:45 – 28:59]
• Daily structure and the Hemingway Principle: [31:03 – 31:58]
• Concrete action plan and final assignment: [35:43 – 37:02]

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Final Takeaways

• Creativity flourishes best not in total freedom, but within self-imposed, well-considered boundaries.
• Begin with small, manageable creative exercises—tight time/word limits, regular deadlines, and clear priorities.
• Don’t expect to have all life’s creative answers post-retirement—meaningful focus comes with experimentation and constraint-driven practice.
• Use methods like pre-writing a “press release” to clarify intention and audience before beginning large projects.
• The importance of structure, even artificial, cannot be overstated for driving progress—regardless of age or context.

“Not every moment is a teachable moment.”
—Ofra, summing up a key insight she wants to share as a writer, [37:02]

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Transcript

[A]

This episode is brought to you by Progressive Insurance. Do you ever find yourself playing the budgeting game? Well, with the name your price tool from Progressive, you can find options that fit your budget and potentially lower your bills. Try [e-mail] Progressive Casualty Insurance Company and affiliates Price and coverage match limited by state law. Not available in all states.

[B]

Hi, it's Mike. And by now you surely realize that this is an advice show. But do you know who invented advice? Dan Savage. On the Savage Lovecast, you'll hear sex and relationship questions like what's polyamory? And what should I do when my two doms give me conflicting orders? If you subscribe to the Magnum version, you will also hear amazing guests like Esther Perel, Ezra Klein, and me, Mike Pesca with no ads. Imagine that Dan has been on the vanguard of gay rights, women's rights, polyamory, kink, all the sex topics. And he is in fact, hilariously funny too. Listen to the free micro version 1 wherever you get your podcasts or check out the subscription Magnum version over at Savage Love.

[C]

There's an increase in a tendency that cognitive psychologists call maximizing, we might call optimizing now, trying to get the best of every decision and endlessly comparing your options. And it turns out that it's almost always a bad thing to be.

[B]

I have always found that constraints help make the product. You probably heard me talk about this if you listen to the gist with a recent guest of mine who has written a bestseller. The guest is David Epstein, and the bestseller is inside the box. David Epstein might also be known to you if you are a listener to this show because he was the host of this show. Well, guess what? We're how to ing this insight about creativity and constraints and taking it to the real world with the real listener who. Who has a real problem.

[D]

I am Ofer Obejas. I'm in my retirement years and I'm looking for my next creative project.

[B]

All right, tell me a little bit about before you retired. What did you do?

[D]

I had several careers. The last of them was 20 years as a psychotherapist.

[A]

Really?

[B]

What you do before that?

[D]

Raising children in homeschooling and before that, computer coding.

[B]

Interesting.

[D]

I worked for match.com once.

[B]

Really?

[D]

Yes.

[B]

How'd that work out?

[D]

It was very short and very, very strange because you have to test the product in real life.

[B]

Is the match.com people you had to work on? People?

[D]

No, computer science. So I wrote the website.

[B]

Okay, so you're now retired, and what are some of the projects you're considering ofra Everything.

[D]

Cooking, gardening, art, humor, stand up, comedy, you name it. I would like to try to do it now that I have all the free time in the world. And I'm very interested in finally writing a book, which people have been telling me to do for 30 years.

[B]

What have people been telling you to write about? But what do you want to write about? Are they two different things?

[D]

Well, when people tell you to write something, it's because they think, oh, you're a good writer, but they don't tell you what. So I'm interested in observational humor, observations from my career, parenting. Because my specialty as a psychotherapist was children, vignettes from my work. Very hard to narrow it down.

[B]

Let me ask you this. Do you want to write a book or do you want to have written a book?

[D]

Yes, I've heard that that's much better to have written a book to actually write it. No, I do enjoy writing.

[B]

So is this more about you look forward to the enjoyment of the task. You are retired. You don't need to do this. But if you commit to a book, I guess you won't be retired. So is this your perceived enjoyment of the task or do you have something you need to say?

[D]

The latter. I want to talk about misconceptions about parenting, raising children, relationships, social commentary.

[B]

Right. And probably do that with the observational humor and all your other skills that you brought to the job as a psychoanalyst and that you just bring to your life.

[D]

Yes.

[B]

And so are all these other things getting in the way of that as you perceive it, or is it more an embarrassment of riches you don't know how to effectively perform triage and all these potential tasks you have?

[D]

Yes, I enjoy so many things. I've been looking forward to finally being able to do that. I. I cannot say no to one in order to focus on another.

[B]

Okay, so focus is one thing. Of the many things that you listed, I think gardening, writing, standup comedy, hot air ballooning, maybe I'm bringing some of my own goals and aspirations to your list. Have you checked off any of the list? Have you gotten far along with any of these tasks?

[D]

Yes, I have taken painting classes and I reached a certain point after which I wasn't going to get any better without really devoting my life to it.

[B]

Okay, so let's take that as an example. Therefore, are you satisfied with that itch or something else? Is it that you define to yourself that this wasn't going to be your purpose in retirement?

[D]

Yes, I'm satisfied that that is just A hobby and will remain a hobby.

[B]

And with the writing, might that be the case? You might say to it might turn out that it was just a hobby and you were never going to be able to finish that book or actually write that book. Would that be okay with you?

[D]

It will be okay, but I doubt it because if I really put my mind to it, I think that I can make something of it because I have been writing all my life.

[B]

I don't want to put words in your mouth, but it seems that there are some things that you'd like to explore with the expectation that I love tried them out and that's fine. And there are other things that you're more committed to mentally.

[D]

Yes.

[B]

Okay. So what's in that second bucket besides the book?

[D]

Humor in any form? Online articles, Cartoons. Stand up.

[B]

Huh? So have you cartooned? Have you done stand up?

[A]

Both?

[D]

Yes.

[B]

Tell me. Tell me about this.

[D]

I just performed in front of a paying audience a week ago at the Improv in Los Angeles.

[B]

Wow. Now appearing now straight from the LA Improv, Bud Friedman's Improv, it's Ofra Abias. What was your set like? Tell us about that.

[D]

It's just five minutes. Yeah, I just had five minutes about how my husband and I are different and little quirks about his personality and mine.

[B]

Okay. What were your expectations going in? What did you want out of that five minute set?

[D]

I just wanted people to have a good time. And they did.

[B]

They did. They laughed.

[D]

They did, yes.

[B]

All right, you've piqued my curiosity. Do you want to tell us one?

[D]

Of course. So despite my last name, Obejas, I am not Hispanic. My husband is Latino. With all the talk about immigrants, I feel a little nervous saying that. In his defense, my husband is one of those immigrants who took a job no American wanted. Being married to me, you should at least get hazard pay or vision.

[B]

And that's good. The misdirect, right? The self deprecation. That's great. Well, congratulations on that. I'm going to assume the next four minutes, 30 seconds went as well.

[D]

Thank you.

[B]

All right, well, we're going to help you because coming up in a minute, we have the perfect expert by so many measures. One, he is an expert on the topic of how to create things and what are the best ways to create things to the form of his expertise is in fact a book, the very thing that you've been thinking about. And three, in the how to context, he is an expert. He has hosted this show in the past better than me. Although the tie will be broken this episode to see if he is a better guest than I am. The host, David Epstein will be joining us in a minute. Summer means you got to change how you get dressed. You want lighter pieces and you want more breathable pieces. That's why I keep coming back to Quints. They focus on high quality essentials that feel and look amazing. Thinker linen, breathable linen, soft organic cotton, well made basics but without the luxury markup that is so true. It's a balance where everything feels elevated but effortless. Everything at quints is priced 50 to 80% less than similar brands and their T shirts are soft and easy to wear and their lightweight cotton sweaters are perfect for those cooler summer nights. One Quince item that I find a pure delight is the European linen relaxed short sleeve shirt. So the linens European, you don't have to wear it in Europe, but it's totally casual and unbelievably comfortable and yet pretty classy. You wear it to any sort of party that has an outdoor aspect to it. Maybe not a wedding, but any kind of even highfalutin barbecue or a white party. If they still do those, they have them in several colors and one of them is the one I got them in, which is which is a white or off white. And you're good. You're good to go. That's what Quince does. Elevate your summer wardrobe. Go to quince.com how to for free shipping on your order and 365 day returns. Now available in Canada too. That's Q U I n c e.com howto for free shipping and 365 day returns. Quince.com howto this episode is brought to

[A]

you by Progressive Insurance. Do you ever find yourself playing the budgeting game? Well, with the name your price tool from Progressive, you can find options that fit your budget and potentially lower your bills. Try [e-mail] Progressive Casualty Insurance Company and affiliates Price and coverage match limited by state law. Not available in all states.

[B]

If you're looking for another podcast that brings therapy resources to your earbuds, then check out the self work podcast. Ten years ago, Dr. Margaret Rutherford decided to extend the walls of her psychology practice as far as they could go, and the Self Work Podcast was born. Each week, Dr. Margaret dives into an issue in mental health that she's personally researched, adding in her own two bits from over 30 years of experience. And you'll also hear the interviews with creative and informative guests who bring their own experience to the table. Her warm Southern drawl soothes and comforts. She's about as down to earth as they come. Rated by many as the best depression podcast out there, Self Work stresses what you can do about it. So if you're seeking ideas and actions to move yourself forward, Self Work is for you. Find it on your favorite podcast app and tell them how to Sent you. We're back with how to and been talking with Ofra, who would like to do so many things life's rich panoply of choices has laid out in front of her as she welcomes her retirement. She's done Stand up. We gave you a taste, a tease. I think if that was on the Netflix special, you might click. She's done some painting, but she really wants to write. And so joining us is an author. He has written Inside the Box how constraints make us better. He's David Epstein. David, welcome back to how to the place like when you left it.

[C]

Thank you. Good to be back. I think the current host has a much better radio voice. In my time as the host, I

[B]

must say, when you walk around how to is it like going back to your old elementary school? Everyone, everything seems so much smaller.

[C]

Exactly. I revert back to my younger self. It's, you know, it's a little embarrassing, but that's, that's human nature.

[B]

Oh, awesome. All right, so before we get to Ofra's specific situation conundrum, ask. I had you on the gist to talk about Inside the Box and it's fascinating and there are things that I've always believed in. Then you also blew my mind with some examples and some reporting that you did. So what's the general, what's the general thesis of your book? And pick a non intuitive way for you to illustrate that thesis, if you will.

[C]

The thesis of the book is that we overvalue complete freedom in the abstract and undervalue useful constraints, even though they can be our most powerful tools for focusing a project, unsticking yourself, or even just figuring out where to apply your energy. And that when we assume that more choice and less structure will all will always make us better off, we're actually usually undermining our own best creative projects and our own possibility at contentment.

[B]

Do you think we do that because it's our honest belief that freedom equals creativity? Or do we do that perhaps as a means of self sabotage? Right. I want more choice. I don't want to actually come to a decision. I just want more and more optionality, which in the end takes away optionality.

[C]

Yeah, I actually think it's a both So I think there is some sincere belief. So there was a recent survey that psychologists did internationally of known creativity myths. And so these were things that we know from research are not true. And the most popular myth was that people are most creative when they are most free. So I think it is a sincere belief. On the other hand, I think there is a lot of evidence increasingly so that preserving optionality has become an end to itself. And so there's an increase in a tendency that cognitive psychologists call maximizing, which is we might call optimizing now, trying to get the best of every decision and endlessly comparing your options. And it turns out that it's almost always a bad thing to be. So maximizers. Yeah, not, not in every case, but almost always, where maximizers tend to be less happy with their decisions, less happy with their lives, much more prone to regret and endless comparison, and much more likely, to your point, to go for reversible decisions, essentially keeping their options open, even though that tends to prevent them from committing one way or the other. And again, there's evidence that some of these tendencies are on the rise, that people make decisions with optionality as the end. In fact, there's a researcher named Scott Stanley who's studied in young people's relationships what he calls sliding versus deciding. And sliding means in the interest of keeping your options open, you don't really commit to that relationship. You say, I'm keeping my options open, I'm not committed. But then you end up sleepwalking into escalating commitment anyway. So your options are. It's the illusion of keeping your options open even while they're closing. And those people end up less happy and more likely to get divorced versus those who say I'm either in or I'm out. And then you commit to that decision and go forward.

[B]

Yeah, I understand how that would play out on the dating market, where there's so much choice and always someone to swipe right on in the job market or professionally. It doesn't occur to me as naturally, but of course this is also true. And the idea of the gig economy has been forced upon us. But there also must be some aspect of people just not committing to the one thing or having done the work, maybe to commit to that career output, that career path that generations past we might have committed to. And I'll even give you an asterisk on that, which is that a lot of people go to a professional school, law school, So I have options. It might be better to go to a law school to be a lawyer. You might be Happier that way.

[C]

Yeah. In fact, I think that's a real. You're absolutely right. And I think that's a really mistaken belief that if people go to law school, they're keeping their options open. Like they'd be better off getting a little bit of experience in the world than deciding if they want to go to law school. Because I do think it's good for people to sample a lot of things and you can change directions. But being endlessly just on the surface, bouncing between things, I think is not a recipe for success because there's actually is evidence. Dashan Wong at Northwestern did this amazing research looking at tens of thousands of careers. And most people's best work will come sequentially, sort of in what he called a hot streak. And those hot streaks are reliably preceded by a period of exploration where you're doing small, low stakes things and trying to figure out where to dive in. So I think that exploration is important, but it's for the purpose of figuring out where to dive in, not for the purpose of keeping your options open forever.

[B]

Yeah, that is true. That is true with artists, that is true with musicians. Right. That is true with directors. Right. The Rob Reiner who tragically died, we look back on his career and what a hot streak. From Spinal Tap through maybe north. And then things stop being so hot. But it was in the beginning, if you know about his career, there was exploration and there was him being an actor and him trying different things. Wow. And it also happens with, from what I know of the guys who win the great breakthrough math prizes. So these are people in their careers. Have you looked at retirement a lot? Because retirement is the area where you were on a path, you were constricted. And so maybe you're saying that's great for creativity. And then boom, it opens up and there are none of those natural constraints.

[C]

Yeah. And in fact, because I've been hearing about a lot of people who are recently retired saying that, you know, I was so looking forward to retiring, I was going to do all these things. And then they lose all their structure and they. They don't do those things because they're much less efficient with their time. All of a sudden they're in this position of having to decide what to decide. Whereas a certain structure, you know, I remember this like when I was a college athlete, I had way more, you know, way more demands on my time. And yet that's when was when I did the best academically, was when I was in season because I was so structured, I knew what I should be doing at a given moment. And I find this too between book projects I shift from a mode where my priorities are really clear to all these little decisions about what should I even be picking to do right now. And so I think when people move into retirement, they are thrust back into what has been an unfamiliar situation for a long time of feeling what do I do now? You know, all this structure is taken away and that, and that's natural. And I don't think there's any way to skip over that. And that exploratory phase is something that they just haven't been used to for a long time. And so I do think that there is no way not to feel some angst about that. Like you're almost. I liken it when I'm between projects to, you know, this is an old school analogy, but an old DJ who's cross fading between turntables, I'm like not really sure which one where I am. And so one thing I think is just knowing that that is a common feeling. Basically everyone has it and there's no way to get through that awkwardness immediately. And so it's just, yeah, it's, it's difficult, but everyone goes through it.

[B]

So I get it. You're a very good middle distance runner. This means you have so much time committed to the training for that and the thinking about that and maybe even when you have to eat and how much you have to eat and if you don't study within this two hour gap, you're just not going to study and choices get taken away from you and you have to do the things. You do do the things. Yeah. So that I understand. But when it comes to retirement, there's no have to involved. So is what we're trying to do impose a concocted have to on ourselves and trick ourselves into thinking it's an actual have to.

[C]

Absolutely. You know, like the great Duke Ellington said, I don't need time, what I need is a deadline. Like you need to put some of those constraints on yourself. And again, I find this in my own writing where I sign a book contract and I don't have to deliver for two years. That vision of this future book doesn't tell me what to do right now. So you have to have much, much smaller chunks of what should I do right now. And I think in retirement this really requires some pretty explicit assessment of priorities. I think even, you know, I've seen this done with in a team setting, but I think applies to individuals where taking all of your current commitments or priorities Putting them on post it notes on the wall. And often what will happen when people do that is they will see, well, there's more stuff here than I could really get to in any satisfactory way, even in a best case scenario. So if I had to cut out one thing in the next 90 days, which would it be? And then do it? Because otherwise we have this bias called additive bias, always to add more things and its cousin called subtraction neglect bias, which is that we will overlook solutions that involve taking away. And this is the theory is that maybe, you know, having too much stuff to do and too much too many things wasn't a problem in human history, but having too little was. So we're basically wired to collect and add and add and add. And that's where I'm kind of curious. I don't know if I'm. If I'm allowed to ask OFRA questions

[B]

but you know, as host emeritus, you have the right to question.

[C]

Yes, because I think there were a few different, different things going on in what she was saying, which is one, figuring out what to do at all, you know, in a given day or maybe in a given year even. And then the. I do want to do a book how to do that and I think those are, those are kind of separate. So I guess my question would be Ofra, if you did the post it notes of your priorities on the wall, where would writing a book be?

[D]

It would be high. I am writing regularly, but probably not as much as I should be. If I want to have a product at the end of it, this is it. If I'm not going to do it now, there's not going to be another time.

[B]

And we now have to deal with a break. No, not deal with revel in the constrains that the break represents. And when we return, I will prioritize the book that OFRA has in her the back in a minute with how to.

[A]

This episode is brought to you by Progressive Insurance. Do you ever find yourself playing the budgeting game? Well, with the name your price tool from Progressive you can find options that fit your budget and potentially lower your bills. Try [e-mail] Progressive Casualty Insurance Company and affiliates Price and coverage match Limited by state law not available in all states.

[C]

My name is Shannon Maldonado. I'm the founder of Yaoi, a gift shop from the lens of artists and handmade objects.

[D]

I chose Shopify because when I was

[C]

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[B]

you're looking for another podcast that brings therapy resources to your earbuds, then check out the self work podcast. Ten years ago, Dr. Margaret Rutherford decided to extend the walls of her psychology practice as far as they could go, and the Self Work Podcast was born. Each week, Dr. Margaret dives into an issue in mental health that she's personally researched, adding in her own two bits from over 30 years of experience. And you'll also hear the interviews with creative and informative guests who bring their own experience to the table. Her warm Southern drawl soothes and comforts. She's about as down to earth as they come. Rated by many as the best depression podcast out there, Self Work stresses what you can do about it. So if you're seeking ideas and actions to move yourself forward, Self Work is for you. Find it on your favorite podcast app and tell them how to sent you. We're back with David Epstein, author of Inside the Box How Constraints Make Us Better. And he's talking with Ofra, who wants to do a lot of things and has been doing a lot of things in retirement. But we've determined writing a book is pretty high. And I will add that of all the things that she wants to do, writing a book will take the most time and I think be hardest just by its nature. But David, take it from there. How does your constraint view of the world, where is it taking you?

[C]

So I think we should work backward a little bit. So there's a figure that I write about inside the box named Tony Fadell, who was the lead designer of the ipod and the co founder of smart thermostat company Nest. And before that he had been at this company called General Magic that had so much freedom and talent and resources they could do anything. And so they did and basically their project spiraled out of control and they became a disaster. And he, he came out of that experience as a zealot for constraints. So for example, at at Nest, he forced the team to work inside a literal box where he had them prototype the packaging before the product because he said, look, if it doesn't fit on this box, that means it's not a priority. So we're putting it off and the the best.

[B]

And if you use the phrase Think outside the box. You got what, docked a day's pay,

[C]

just fired immediately, no questions asked. And he gave me the advice that he gives to entrepreneurs now, which is to write the press release before, before you start the project. So what is the problem I'm trying to solve? What will this look like? What do I want this to look like when it's done? Who is it that I want it to reach? So I did that for my book. It's kind of painful. It makes you think hard, but that's the point. These constraint exercises make you think hard. And I think for Ofra, part of the question is with that would be in a perfect world, is it with these ideas, say misconceptions about parenting that you've developed expertise in through your career, would the press release of what you want to do be that this is reaching the most people or would it be a book? Because like for me, I love the process of writing. So it's a book because I love the process. But I think one thing to establish, I think it would be useful for you to do that press release and partly to help you figure out who is it that you're trying to reach. You know, what's the person that you're pitching, who's your customer? What is their problem that you're solving for them and does the form matter? Like is this, are you tied to a book or is it more that you want these ideas out there?

[D]

I want the ideas out there. I think that I have figured out some things during my career. I have a entertaining way to present them so the medicine goes down better and I think people would benefit from hearing these ideas.

[C]

Okay, so. So it sounds like you're a little bit form agnostic because I think we can talk about both, both possibilities about, about a book and just about getting the ideas out there. And one of the things that I think is useful it given that you're not necessarily tied to doing it in book form, is that I'm a huge fan of low stakes practice. Like how can you test something in as small a way as, as humanly possible? Right. A book is a, is a big thing. I think of Pixar for example, and I spent a bunch of time with the co founder, Ed Catmull and he said they would keep directors in small teams for years refining the core of a story before they moved into production because the costs only explode once you move into production. So you can be nimble and learn and test and all these things when you're small. And for me, a book Going into a book is kind of moving into production before you've like, that's a big project before you've done a little bit of the testing. And there are all these other forms now, whether it's substack or, you know, Instagram. And some of the stuff that you're talking about sounds to me like a fit to try on Instagram reels with you talking about some of these experiences. You know, you're funny. You can do it in a minute or 90 seconds and make one of your points and start to get a little bit of feedback. This very low stakes testing, the worst case scenario is basically nobody sees it if you know and maybe it spreads, but you can start to get a little bit of that feedback. And since on an Instagram reel, you're basically looking to do something in one to two minutes, essentially, that's going to really give you this very defined parameter. You could go longer, but don't. I think that will feel much more manageable than the sprawling idea of just writing stuff toward a book. So small. Small, small. Like as small as possible. And I mean, I use my substack newsletter to sort of test ideas when I'm thinking out loud too, because it's, it's a small way to do it. And I think that would be useful for you both to get a little feedback, see if maybe that, maybe you prefer that, that medium or just a little testing to see if you want to go forward into this book.

[D]

Hmm.

[B]

What about taking substack and taking reels? Because to me they're just different lengths and one is spoken, even if it's crafted and one is written and using them for different things. Or would you say were getting in the way of the limitations and the constraints that your recent scholarship is about? Because I was thinking something like exactly what you're saying for the reels, based on a point about her topic, raising kids or parenting that she wants to make that could be on reels. But a case study or, you know, an anonymized patient she has written out in a narrative form could be on substack. And then if a book were to come, it's a merger of those two kind of things. Or in your estimation, is that making an optimization or other kind of mistake where I'm getting outside limitations, getting outside the realm of the constraints that are helpful?

[C]

No, I think that's a good idea. Because part of the question here is what form does she want to do it in? Right? So there's, there's both the being forced to condense it. And also trying it as writing and trying it maybe as video and seeing how that feels. I would say on substack, I would give a word limit. I would say, you know, for these first posts, try no more than 800 words. Give yourself a limit and a cadence. You know, whether that's once weekly, whether that's every other week, and a lot of structures. Because I think one of the challenges for people in retirement or people like me who have tons of career autonomy is where do I start today? And it's pretty typical that when people don't know where to start in a given day, they will start. There's two things that happen. One, they'll either start with something convenient, which is like scrolling or checking email. Things like that.

[B]

You'll just check stuff the noodle around. Period.

[C]

I know around.

[B]

Yeah, yeah.

[C]

And. Or there's something called the mere urgency effect, where you will turn to something that feels urgent even though it's not important. So you're like, oh, this. This is a thing that's coming up. So I'm going to do that, even if it's like, would be very low on your priority list and you're doing it in place of things that are maybe not as urgent, but are more.

[B]

Okay. A thing that's taking your time away from this writing project.

[C]

And so I think it's important to. I've been calling this something the Hemingway principle recently, where Hemingway, Ernest Hemingway would stop in the middle of a sentence each night at the end of his work so that he knew exactly the next day where he had to pick up. And I think that can be really useful. I don't. I'm not saying you necessarily have to stop in the middle of a sentence, but I would say the last thing of each day is, where am I? That you write down is where am I starting tomorrow? So that it doesn't just become a scroll or a turning to your inbox immediately, but it's the thing that you know is important. So, like today, I mean, I usually put it on one sheet of paper. I mean, you can even see I'm. I was taking notes on what Ofra was saying. But, like, on the top of my sheet of paper, I have one thing, which is I have to write this newsletter draft. And so that's what I was doing this morning before this, because it was the one thing on the list. So if you don't designate the place you're going to start, then your brain will go for convenience and start in places that are easy but not important.

[B]

So what do you think about the idea of doing some stuff on Instagram and then some stuff on Subway or let's take them one by subway. Substack. Some stuff on substack. Let's take them one by one. How's your comfort level with talking to the camera and doing Instagram reels on some of your thoughts?

[D]

I'm comfortable. I've given presentations in my professional career that is very doable. There are people in my former profession who pivoted to being just TikTok therapists. Yeah, I'm not in favor or against it, but we're very comfortable communicating our ideas. And the limitation of writing an 800 word substack and getting immediate feedback, does this resonate? What are people thinking? Does this idea, should it be developed further or abandoned in something new?

[B]

Well, I, you know, I don't even know if you can rely on or trust any audience to show up or what the audience necessarily says. I mean. Well, what do you think about that, David? Is the substack exercise more for OFRA or more for getting feedback?

[C]

More for ofra, especially, because if you're not already on there, you wouldn't have much audience when you start, and so you wouldn't be relying on the audience anyway. You may get some feedback. I mean, you may sign up people that you know from your professional network or your personal life. So you don't need a ton of people to get some feedback also. But I think primarily it would be for you to have a concrete way to start condensing some of these feedback these stories and anecdotes. And you're already good at condensing. You did a five minute comedy routine like, you know how this goes. And so I think that can be a really useful exercise for you because the sense I get, and correct me if I'm wrong, is that now you're kind of almost doing maybe like a diary of these thoughts that are in your head, just like sort of splurging them out to get them out there and recorded somewhere. Is that kind of the kind of writing that you're doing now?

[D]

Yes, whatever comes to mind.

[C]

Okay. And so that can be useful raw material where. So there are individual ideas in that there are individual stories. Pick one and do the sub stack on one of them. You could even go through what you've written and like, mark, each one of these is a story or idea. And that's the nugget of one post.

[B]

Right. So the move is not write the book tomorrow, it's identify one story, one idea. One small container. But that also raises the bigger question, how much does this matter to you?

[D]

Well, while writing, whether a short article or book was not part of my professional identity, teaching always was. And this is just another way to get my ideas out there. So that is my identity. I always designed presentations, wrote professional articles. It's not something that defines me, but it's certainly something I would like to be part of my identity in retirement.

[C]

For how long have you been retired?

[D]

Almost a year.

[C]

Okay. So that may feel long, but in the scheme of your life, that is still quite new. So I think one thing is you don't have to have it all figured out, right? This is going to come together slowly when you make a life transition like that. And I've been hearing this a lot again from people who are retired and thinking that, oh, this will be amazing and then they're kind of a little bit rudderless. Right. So I think that's, I think that is, is okay. And so I think you're clearly in this period where you want to communicate some of these ideas there you have an organizational challenge with them and then the structural challenge of doing it. But it seems like it's important enough that it should be something that's scheduled regularly and that you should start trying in these sort of bite sized pieces. And I think if you have a specific time window, you'll pretty soon that will be like focus time for you and you'll, you'll know what you should do and that can add some structure and give you some momentum.

[B]

So I think that, I think that we've made some strides. I think that we've given some great advice. I am going to give you an assignment and I do this to help you and not at all because it'll possibly be a cute little segment to end the how to episode. Why don't you as an assignment and I'll give you a deadline. We'll figure out when this show runs, but let's say three weeks from now. Why don't you write up for us the press release of the book. Is that, or is that jumping the gun too much, do you think, David?

[C]

No, I think you should try it. It doesn't, it's a. It's, it's difficult. It might require hard thinking and I would do it on one page and if you have a second page, I would include even say it got reviewed. What you would like those reviews to say again, I'm stealing this from Tony. Fidel, that's awesome.

[B]

And do two glowing ones and one jerk on Goodreads who, you know, didn't just didn't like it and didn't think that the mystery resolved in the end, even though it wasn't a mystery.

[C]

Amazon box was torn one star, right?

[B]

I didn't like the main character. She was kind of whiny.

[A]

Yeah.

[C]

Yeah. And I would also think about in, in that time, say, tell us what's like one of the the misconceptions about parenting that, that you are interested in sharing with the world.

[D]

One that comes to mind immediately is that parenting is about teaching, giving children lessons. And one thing I kept saying to parents is not every moment is a teachable moment.

[B]

Right. Sometimes you just got to save them from drowning.

[C]

That's a really good like substack post title or chapter title. Not every moment is a teachable moment. And is there a specific parent or family that you remember that particularly exemplified that principle?

[D]

The idea that a child does something and the parent immediately corrects them to educate them. Just be in the moment with them or they start being afraid to share anything with you.

[B]

David Epstein is the author of the New York Times number one bestseller range and Newly Inside the Box, How Constraints Make Us Better. Thank you, David.

[C]

Pleasure. Thank you for having me.

[B]

Ofra Obejas is a retired psychotherapist who falls in love with an Incan soldier in Ireland. Thank you so much, Ofra.

[D]

My pleasure.

[B]

If you like what you heard today, please give us a rating and a review. We do need your questions that start with the words how to. Email us@how toikepeska.com and today on the Gist, I just interviewed Ben Fountain, who is the author of Billy Lynn's Long Halftime Walk. In a new book called Rasputin Swims the Potomac, we talk about how many characters and perspectives there are in the new novel and how that reflects where we're headed as a society. You know, the way our brains, our hearts, our heads are being rewired. You know, our daily routines, how we act toward one another are undergoing some pretty radical changes. And I think that creates tremendous anxiety and uncertainty.

[D]

So that's what I'm trying to get on the page.

[B]

So listen for that in the gist. How to is produced by Jeff Craig and Cory Wara. Michelle Pesca puts the can do in How To. Charles Duhigg founded the show, is the author of such bestsellers as the Power of Habit and look out for his latest novel with a spicy hook, El Conquistador Cobarde, available for pre order now. I'm Mike Pesca, back every week answering your questions. Of how to.

[A]

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[C]

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