Podcast Leaving the Default Path Family, Relationships & Parenting Finding The Others

#127 The Art of Quitting & Reinvention - Nina Simon on living "off the grid" in an intentional community, taking "turns" in marriage and work, having kids on an unconventional path & leaving her dream job at NASA

· 3 min read
  • 0:00 – Video intro
  • 0:46 – Introduction
  • 2:11 – The scripts Nina grew up with
  • 5:18 – Did Nina see herself as creative growing up?
  • 6:14 – Nina’s education and why she hated her dream job at NASA
  • 9:34 – Fulfillment or lack of it at work
  • 10:56 – Balancing your passions
  • 12:52 – Fitting your life into your job vs fitting your job into your life
  • 15:14 – Nina’s approach to money, building a marriage that supports entrepreneurship
  • 20:33 – Writing books
  • 28:19 – Giving herself a permission
  • 31:11 – The freedom to leave
  • 33:58 – Making choices that are not “the right choice”
  • 37:19 – Should you try to convince other people of your way of life?
  • 39:21 – The non-traditional paths and having kids
  • 46:53 – Reinventing yourself, knowing when to leave
  • 50:46 – Learning from failures
  • 53:31 – Constructing backward narratives about our lives
  • 1:00:07 – Does Nina have a path role model?
  • 1:02:21 – Things that inspired Nina in the last few years
  • 1:04:42 – The one thing Nina would say to her younger self
  • 1:06:00 – Where can we learn more about Nina?

At each professional crossroad, Nina Simon has made the choice most likely to disappoint her mother. She left an electrical engineering job at NASA to design spy museum exhibits, said goodbye to a museum directorship to start a global movement for more inclusive cultural organizations, and now has put down her CEO hat to write crime fiction. Her first novel, Mother-Daughter Murder Night, will be published in 2023 by William Morrow. Nina lives off the grid in the Santa Cruz mountains with 20 people, 16 chickens, 2 trampolines, and 1 zipline.

We talk about:

  • Leaving her dream job

  • Living in an intentional “off the grid” community

  • What she learned from her ambitious days as a museum industry leader

  • Marriage & kids on an unconventional path

  • Writing her novelWATCH On YouTube

FOLLOW NINA

0:00 Audio intro

0:12 Introduction

1:37 The scripts Nina grew up with

4:43 Did Nina see herself as creative growing up?

5:39 Nina’s education and why she hated her dream job at NASA

12:17 Fitting your life into your job vs fitting your job into your life

14:39 Nina’s approach to money, building a marriage that supports entrepreneurship

19:55 Writing books

27:39 Giving herself a permission

33:17 Making choices that are not “the right choice”

38:37 The non-traditional paths and having kids

46:08 Reinventing yourself, knowing when to leave

52:42 Constructing backward narratives about our lives

Transcript

At each professional crossroad, Nina Simon has made the choice most likely to disappoint her mother. She left an electrical engineering job at NASA to design spy museum exhibits, said goodbye to a museum directorship to start a global movement for more inclusive cultural organizations, and now has put down her CEO hat to write crime fiction.

Speakers: Paul, Nina Simon · 158 transcript lines

Read the full transcript

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Today I'm talking with Nina Simon. I am super pumped for this conversation. She's somebody that has reinvented herself many times. Didn't really know how to introduce herself, but she gave me this incredible one-liner.

At each professional crossroad, she's managed to disappoint her mother by her decision. A common theme among Pathless Pathers, people taking unconventional paths, and something you experience when you make changes. Um, you've done a ton of things, Nina, like working at NASA as an engineer, kind of jealous with that as a fellow engineer. Designing spy museum exhibits, working in the museum world as both a leader of organizations and also just somebody who's super passionate about the space. You have reinvented yourself a couple of times in that space and now have left that behind and are focusing on writing crime fiction. You're going to publish a novel in 2023 called Mother Daughter Murder Night.

Which I've— it's a good title. I'm hooked already. But, uh, yeah, Nina lives in Santa Cruz with 20 people, 16 chickens, 2 trampolines, and 1 zipline. I am excited to chat with you today, Nina. Welcome to the podcast.

[02:32] Nina Simon: Thanks, Paul. I'm really glad to be here.

[02:36] Paul: Question we always start out with is, what are the stories and scripts you grew up with as a child?

[02:45] Nina Simon: About life around them. Yeah.

[02:48] Paul: Yeah. So what are the stories and scripts you grew up around work? Like, okay, these are the things I am supposed to do as an adult to be seen as a successful person, but they can be life scripts as well.

[03:00] Nina Simon: Yeah. So I'm Jewish and my family, you know, there's this generational thing about immigrants, right? Where in my case it was grandparents come over, they try and make a good life for themselves and their kids. And then, you know, there's kind of this cycle of who are the kids or what are the generations where you try and really toe the line and do what is expected and what are the generations where you're able to flex a little bit. So my parents were quite unusual. My dad's a rock musician.

He has literally had the same job since he was 20 years old, which is being in the band Sha Na Na. And so had a very radical career in some ways, but in some ways very traditional in that he literally has been in the same job for 50 years. My parents got divorced when I was 7, and that was a real moment when my mom realized that she had this real sort of protective, ambitious gene of feeling like She never wanted to rely on a man, a husband, um, for her financial security, for that of her kids as well. And so, um, my parents had joint custody, but my sister and I spent a lot of time with my mom as she built a career as a mother. And so I think that we saw very clearly that work is about independence and creativity, but it's also about independence and freedom in this way that is more primal and more about survival. And I think that Both my sister and I really were always proud to work.

You know, I was— I remember getting my work permit when I was 14 and having a series of awful jobs. One of my favorite questions always to ask people is, what's the worst job you've ever had? And I always feel a little bad for people who didn't have jobs de-thorning roses as I did, or any number of terrible jobs, but just was always proud to be working, to be contributing. And always felt like work was something that, again, you know, my dad had gotten this very lucky strike of being creative and having kind of, you know, what is seen as a dream job. But we also, as kids, really saw the ugly side of being in a rock band and, and saw how my mom kind of being more of the turtle and going for hard work and entrepreneurship in her own way, could also have a lot of independence and joy and success in that. So I think that we saw work and I saw work as something I was excited about.

I saw different versions of it, but definitely saw that it was connected to security and freedom.

[05:42] Paul: Did you see yourself as creative growing up?

[05:45] Nina Simon: Definitely creative. But one of the things that happens when you grow up with a creative as a parent is at least in my house, whenever I was practicing the piano, my dad would, you know, call out, that's the wrong note, you know. And for me, that was very demoralizing. My sister is an amazing musician, but for me, my creativity went into writing. So I was always writing poetry and was really stimulated in that way. You know, when I was in high school, I felt like I was a very left-brain, right-brain person.

I was both super jazzed about creative writing and about math and science. and I actually decided to study electrical engineering because I felt like, you know what, reading and writing's something I'm always gonna do, but I'm pretty sure the only way I'm ever gonna learn how to actually build stuff is if I go to engineering school. But it was like, you know, a razor-thin margin of that decision for me.

[06:38] Paul: Yeah. And you ended up at NASA. So when you were leaving college, did you see yourself as like, this is my path? I mean, I feel like a big thing in our culture is this sort of kind of a delusion that we think we need to solve the path at 23. How are you thinking about life?

[06:56] Nina Simon: Yeah, you know, actually, while I was in college, I spent a summer living in this really wild place, this farm in Minnesota that was an unschool. So there were kids there who learned by doing and with no adult instruction. Actually, the adults, they were quite militant about like Even I remember once a 6-year-old came up to me, I was playing solitaire and asked how to play, and I was showing her the rules. And this adult was like, don't teach her how to do it. You know, she can figure out. I'm like, okay, that seems a little extreme.

But, but I was always fascinated by learning outside of compulsory environments. And it's actually one of the reasons I ended up in museums. But yeah, when I first went to engineering school, I was a great student. And, you know, when you're a good student, you get these messages sent back to you again and again. You should go to graduate school. You should take this internship, da da da da.

And I kept doing that. And every summer I had an engineering job that didn't quite feel right. When I was in high school, I used to say I wanted to design pinball machines because it's kind of this beautiful combination of like creativity, storytelling, engineering. It's all in this box. And but it turns out that nobody really designs, especially, you know, non-computer-based pinball machines anymore. And and that every engineering job I got, it didn't have that combination.

And so I thought NASA was my dream. Certainly when I was a little kid, it was my dream. And then pretty much immediately when I got there, Paul, I realized I hated it. And actually, you know, I was in D.C. like living the dream. You know, I graduated from college early, went right to this job at NASA, and I was doing math in this like room with no windows.

And I just hated it. And on the weekends, I was volunteering at this children's museum making puppet shows about big math concepts like infinity. And I loved it. And so I quit my NASA job to take this like $5 an hour job at this children's museum, which again, first of many choices where my parents were like, oh my God, what is our child doing? And, but I really felt like for me, the joy of math and science is about the wildness and the weirdness and the creativity in it. And I just didn't experience that in my work world.

What's a little bit weird is my mom worked for Disney when I was a kid and we lived right down the road from Disney Studios. And I think that if at some point I had stepped off the path a little bit to do an internship with Imagineering, I think I would have stayed. And I think that that would have been the right kind of engineering for me. But there's some reason, I don't know if it's about my mom having worked there or what, that I never went to the Imagineering or theme park world and And I'm grateful for the path I've had, but I often think, oh, there, I just didn't know. To what you're saying about that fallacy of knowing what you want, you also just don't know what's out there. And I think that, I think I thought I was making a good try at figuring out where are the creative quirks of engineering.

And I never made it to a few places where I think maybe I could have really found fulfillment.

[09:59] Paul: It's such a hard thing. For me, engineering was the same. I did 3 different internships and decided I didn't want to do any of those each time. Yeah, I was still flailing like 10 years later, like job to job. But I think nobody designs the pinball machine is almost a principle to take away from that. Like engineering, you'd probably be like designing the spring on the puller for like a product launch like 3 years from now.

That's like the reality of an engineering job.

[10:31] Nina Simon: And like, I was in industry at NASA. It's like you're, you're designing like the circuit on the thing that might go on a payload in 10 years if our work, our deal with the Chinese for satellites works. Yeah. You know, it's interesting though about the like fallacy of you're going to find the job because while I was in engineering school by day, I was a slam poet by night. And so I was spending a lot of time while I was in college with people who were artists who had really shitty day jobs. And I got to see also what it was like to have this thing that you were the most passionate about not be your job.

And while I wasn't sure that that was the world I wanted, I definitely saw both versions. And so it wasn't like I only saw, you know, job equals fulfillment. I was curious, though, if I could find that in some way. And to a large extent, I did for a long time in museums.

[11:21] Paul: Yeah, I, I've seen that pretty often too. Like, it's very hard to make your passion your job, especially if you're aiming directly at it. Some people can sort of stumble upon it and stay in a space in which they're able to generate money from their activity for a certain amount of time, but it never quite lasts. Talk to me about like how you've thought about that and how that's changed over time in terms of like Okay, does the thing I'm most passionate about need to be the center of my life, or how do I structure that?

[11:52] Nina Simon: Yeah, I think that I'm one of those people who really needs— some people need balance sort of over a year or over a month. I almost on a daily basis, I need to exercise, I need to be creative. I need to, you know, be doing something that I feel is purposeful and with people. And so I think that there have been times in my life where my job has given me most or all of those things. And then there have been times where it didn't. And I think that I never assumed that if my job wasn't giving me all those things that I couldn't, you know, find those elsewhere.

And so for example, you know, when I first started working museums, poetry was a big part of my life, but because I had, that had been my balancer against engineering. And as soon as I was designing exhibits, as soon as I was doing creative work in museums, poetry became much less part of my life because I was having that creative fulfillment at work. And so I think that there have been times where it's all been at work, but I'll also say I didn't necessarily presume that those were better times or better jobs than the times when I had a job that only really scratched one of those itches. And so I think that, you know, I feel like for me it's about how do I pursue a life or opportunities so that on a daily basis, I'm getting to do the things that fulfill me as opposed to thinking all those have to come in this bucket or that bucket or that kind of thing.

[13:16] Paul: Yes. So many people start with like the job is like the center of life and then try to design their life downstream from that. It seems like you had this sense from an early age of like, okay, I have all this space, which is my life. Maybe I'll fit a job into that. Is that like how you were actually thinking about it? Or is that how it just, your natural tendencies brought you into that?

[13:40] Nina Simon: That sounds great. I think that, you know, I don't know if you're into the Enneagram at all, but I'm an Enneagram 7, which is like the golden retriever, like chasing the tennis ball, you know, interested in a lot of different things. So I think that I've always both pursued a diversity and novelty in my life, and I also have always been really hardline about if something, if a job in particular is not working for me, I am leaving. And I'm leaving quickly. I'm not agonizing about that. And I've done that a few times.

And so even, you know, when I left engineering and shifted into museums, I did it because I was curious about these creative spaces. I, you know, there's this idea of like no one ever failed museum, that they could be really places for free choice learning. But the first year I worked in museums, I worked in like 6 different museums. And my strategy was I'd go to a place, I'd say, hey, I'll volunteer for you for free or do an internship for 3 months. But then at 3 months, we're going to talk about whether you're going to pay me or not. And sometimes those were really great fits and I did end up working there and getting paid.

Sometimes they were bad fits and I just left, you know, but I was just like, I want to explore different sizes. I want to explore what's it like to look for a mentor to work for versus a place with values I care about, you know, like I just wanted to experiment with a lot of different things and I didn't feel like I, I think I early on just valued my own freedom so strongly that I didn't feel I owed any company some certain amount of my time before there could be a decision about making a different choice. I think also paradoxically, museums are one of those career or industries that's very hard to break into. And because it was hard, you know, I think for some people, if you get into a hard to break into environment, you feel like, oh my God, I gotta keep this job no matter what, even if it sucks. But for me, it was sort of like, it's already impossible.

So I might as well just try and figure out like what, what's good here and, and, and be really aggressive when I see something that I do think might be the right fit.

[15:39] Paul: That's amazing. How were you thinking about money?

[15:42] Nina Simon: There's a privilege side to this and a choices side to this. So the privilege side of it is my parents had the commitment that they were going to make sure that my sister and I could go through undergrad debt-free. Which was amazing and I feel like is a huge gift. And then we also— and I had the commitment that I'm going to be working as soon as possible and I'm not going to ask you for any more money after that, you know, no phone bills, no rent, no nothing. And, and so I always have lived very cheaply. And I think that, you know, the single biggest decision I made that has changed my whole career is meeting my husband when I was 20 years old.

And us deciding, you know, that we were going to be together. He at the time was 25. He was living in this group house where it's like everybody is paying almost nothing for rent in this terrible house. I mean, it was just like bananas. But we both really had this sense that our professional freedom— he was an entrepreneur, he taught me about entrepreneurship— but that being able to do what we want to do, being able to leave when we needed to leave, matter more than almost anything else. And so we have always first implicitly and now very explicitly said we are going to fully live, including saving, including giving away money on one salary.

And at any given time, one of us needs to be not necessarily stable, but one of us needs to have a paycheck that's coming in and we're going to trade off who that is. And we are going to do that so that we can be super psyched to support each other. When he wants to start a business and it's going to take a few years to get off the ground, or I want to write a book and I don't know what's going to happen with that. And we've done that multiple times over 20 years and, and lived extremely cheaply the whole time. And it's like the greatest gift we give each other as a couple and, and a choice for ourselves about money.

[17:33] Paul: I love that. Me and my wife have sort of set up a similar way of orienting, and it's interesting how common the like one income rule is in like two— I don't even know what to say— double weirdo couples instead of double income.

[17:50] Nina Simon: Yeah, yeah, yeah. But yeah, it's really more like the one health insurance rule is kind of how we think about it. Because I mean, and frankly also the fact that I'm younger and than him, and also my experience with my mom being, you know, um, thrust into being a a home, you know, thrust into making money in a somewhat unexpected manner means I've always been really competitive about wanting to be the one or wanting to, you know, and we've, we've had some failures, but we've also had some successes that have really just made this possible and also just continuing to live really cheaply.

[18:30] Paul: You said you're thinking about that explicitly. Can you say a little bit more about what that means? Is that like putting numbers down? Like, how are you defining all this?

[18:39] Nina Simon: Yeah. So years ago, so, you know, I've always been really professionally ambitious, but I was always also nervous that, like, he's professionally ambitious too. And how do you decide who takes— whose, whose thing takes precedence? And when I was in my maybe mid-20s, so, you know, I started working, doing some exhibit design, and then I started this blog in the museum industry that became the biggest blog in the museum industry. And it sparked this freelance career that was awesome. In my later 20s.

And during that time while I was freelancing, I met this super power couple in the arts world. And they, I was like, how do you decide who's, where to go? Because these, this couple, both of them, each of them were taking jobs running bigger and bigger museums. And this woman said to me, my husband Tom and I, her name's Madeline Gruszynski, she said, you know, we've made a deal. We trade off whose turn it is. And when I, you know, and we've done it 4 times and we've done it, you know, each time it's been 5 to 10 years.

And I was just like, holy shit, these people have this together and just got interested in this idea of how can we support each other? And especially, I mean, you're about to have a kid. I have a 9-year-old. You know, how do I, as the woman, not become the de facto opt-out? And in fact, in our case, you know, I had just become a CEO a year before we decided to have a kid, and my husband had this startup that was struggling at that time. So we decided he was gonna be the lead caregiver.

And, you know, I went back to work after 10 days after having my daughter, super excited to do it, felt super privileged to do it, and felt super grateful that he was making that choice. And I think that, so I think there's also, I think in any heterosexual couple, there does have to be some constant vigilance about like, hey, are we not sliding into, you know, like oppressive systems here? And so I think that that has also always been a driver. And being the younger one and getting together with him when I was like new to working and he already had this startup just made, it really set a fire under me of wanting to be an equal in that partnership.

[20:55] Paul: Yeah, one thing I think a lot about and we talk about is not defining it solely in economic terms. So similarly, we try just not to spend a lot, which gives— which lets us price our freedom at a higher rate such that if we do want to work on things that matter to us, maybe that won't be economically valued. We can sort of like lean into those and like those things matter to me so much. And like, it would kill me if like my spouse didn't have like her art and she didn't have the energy to do that.

[21:32] Nina Simon: Yeah.

[21:32] Paul: Whether she'll make money or not is who knows. But it's not like the goal. There's like intrinsic value in things in and of themselves. How do you, how do you think about that? Like you're writing a book right now. Like books are like impossible to think about selling.

I wrote a book in 2020. Won, um, and I, I had no idea. Like, I was self-publishing. I had no idea, like, how much it would sell or not sell. Um, I basically projected, like, zero sales, and it did better than that.

[22:02] Nina Simon: So, well, that's good.

[22:03] Paul: Yeah, lucked out.

[22:05] Nina Simon: Well, so, yeah, so, you know, I, um, there's two very different versions of that story because, um, so I mentioned, you know, when I was 25, 26, I started this blog Museum 2.0 that created a consulting career that I didn't know I could have. You know, I was working as an exhibit designer. I thought my goal was to become an exhibit designer at bigger and bigger museums. And then I started writing this blog about participatory culture and like, what is the story of Web 2.0 as applied to cultural spaces? Not what's happening online, but what would it look like if a museum was operating the way that Wikipedia works or, you know, Twitter works or whatever that might be? And, and suddenly people were calling me and treating me as this expert and flying me all over the world.

To do consulting. And so out of that, I wrote two books actually that I self-published. And in that case, it's like I really saw that the blog had already been a huge lead generator for a very successful consulting business. And I figured— and I'd heard from a lot of people who were like, hey, I love your ideas, I love your blog, but my boss is never going to read a blog. And so can you do a book? And so I knew there was sort of a market And, and I also decided actually in the case of those two books to make them totally available for free online as well, you know, which I had been really inspired by Cory Doctorow and Clay Shirky and some of those ideas around, you know, the power of things that are free.

And so I was selling paperbacks and making these books available for free online, and I made a shitload of money. I couldn't believe it. And, and so Like I had that experience with self-publishing and seeing how it was a virtuous thing with consulting. On the other hand, you know, I don't know if you've experienced this, but I stopped consulting because I felt like when consulting, people always want to talk about the thing that you're no longer interested in. Like, you know, you, you publish a book, like you finish a book, you're so sick of it at that moment, and then you have to spend like the next few years being that person. The second book I wrote, The Art of Relevance, I love that book, but I wrote it super fast.

I thought it was something I was just sort of curious about. And then it became like my thing for years and it drove me nuts. And so, so I think that I saw that a book could be financially advantageous if it was part of a package of a brand, a consultant, you know, another product. Speaking, I did a lot of speaking. And so that was financially actually a pretty safe bet. And it was building on what I was doing.

The book I am writing now, completely different story.

[24:47] Paul: I—

[24:49] Nina Simon: so I was a CEO for 10 years and in late 2020 my mom got super sick. She has a form of terminal cancer. She's still alive, which is great, and she's actually doing pretty well. But at the time it was like, holy shit. It was— for me, it was that wake-up moment where I, for the first time in my life, didn't want to put work first. I mean, I had a baby and I was psyched to get back to work, but when my mom got sick, I was, I was just pissed.

I went to work apathetic, you know, I was CEO of this growing startup. It was terrible, like, and I just knew I needed to leave both because I wanted to focus on my mom. And it just put into like sharp contrast and clarity, like, this is not what I want to be doing right now. I feel like that's true for a lot of people, right? That a health crisis, whether it's their own or somebody else's, is a wake-up call. And people talk about it with babies, but I didn't feel— with the baby, I was like, you take care of this crying thing.

I will go to work and I will be a great partner and co-parent. But like, this is not changing my life. But, but my mom's health really changed my life. And, and so in the wake of that, while my mom was sick, So my husband was like, look, you've been the primary wage earner for the last 10 years. Like, yeah, you're due, you get this time. And I felt so much guilt and so much shame about it.

I felt like on the one hand I was proud to be helping my mom, but every time I like made a nice dinner and felt a little proud about it, this other part of my brain would be like, this doesn't matter. Like anybody can make dinner. You're, you're, you're achieving nothing right now. And I really had to like deprogram a lot of the messaging about like it only counts if you're doing things that move things in the world or whatever. But I— so I started writing that book, this crime fiction book, as a way to connect with my mom. She and I both always loved murder mysteries.

And when she was really sick, we needed something to talk about that wasn't cancer. And so I was like, well, what if we made up a story about a detective who was like you? And I would write these chapters while she was sleeping, and then she would read them. And it was just this really sweet connection for us. And it was also a way for me to do something that was so transparently not in the marketplace, like so deeply creative and weird and just for me and her, that it kind of helped me with some of that deprogramming. And then the irony, Paul, is that a year after I finished the first draft, we sold that book, my agent and I, to HarperCollins for more money than I've ever made in a 2-year period.

And so it was like this weird thing where I had spent a year deprogramming myself and telling myself, this is an unusual time in your life. You're going to do this thing and you get to care for others and you're going to write this book and you're just doing this thing. And it's not going to be rewarded by the marketplace. And then suddenly it sold for a lot of money. And so now I'm in this weird place of like, huh, maybe that was not an anomalous period. Maybe this is the next phase for me.

And it's even weird to be— to have the externality of the market response. I'm very sensitive to the fact that, huh, like, why is that driving my next— like, is that Is that it? Is that like, it just as it wasn't a good reason, it would, you know, it was fine to write the book not thinking it was gonna make money. Now that I could make some money writing fiction, like, is that a good or bad reason to keep pursuing it? So that's kind of a long answer around the book thing, but it's been a very confusing experience around this fiction book in particular, 'cause I went into it for one purpose and it is now finding a life beyond that purpose.

[28:39] Paul: So many, so many questions here. I love this so much. I think I sense for many people there is this like other— if you're able to like disconnect from like the person you are, there is this like sort of hidden unknown path. But to do that, you sort of need to lean against everything that makes sense, right? And you describe like the pain of of doing that, that other voice that's like, you're an idiot, what are you doing? Yeah.

How did you soften your attachment to that voice?

[29:16] Nina Simon: I mean, my mom and I used to joke about it that it's like, this is a good thing cancer did. And we used to joke about like, oh, you told your board you quit your job because you have to take care of me. But like, really, you need to take care of, like, you're burned out and like, you need this. And And so we, it like, what a weird thing to play the Cancer card to give yourself permission to, yeah, to do these things. So I think that that was a big part of it was knowing that I was doing something that was, you know, anytime I got too far down that road, I could always say to myself, wait, you're doing something that is unassailably good, which is helping your mom during this hard time.

And but that's a much more simple story than what was actually happening because, you know, if you talk to my husband, he's all— he's thrilled about this writing thing because he's like, you're so much nicer than you were before. You're making great dinners every night. Like, you're really present for us in a way you weren't for a long time. I also am noticing, like, I have a lot more friendships, deep friendships, than I used to. And it's not because I love these people more. It's because I have more time.

Like, if you need a ride to the airport now, I can give you a ride to the airport. Let me tell you, I was not giving anybody a ride to the airport when I was a CEO, you know? And so I think that the permission came from this very clear thing of my mom having cancer, but that also became an on-ramp to find more and more reasons to give myself permission and also just to feel less, less embarrassed. I remember You know, when I was first doing this, I talked to a colleague, an old colleague in the museum world, and I was telling him about what I was doing, and he said, "So are you writing this novel, like, ironically?" And I was like, "No, it's not, like, this is my life now," you know? And so I think even—

[31:09] Paul: I don't think you could write a book ironically. That would take a tremendous amount of effort.

[31:14] Nina Simon: Yeah, I think that readers would not respond well to that. But even like, I've been really intentional in not hiding how my life— or once I got comfortable with it, starting like being explicit on Twitter that like, I'm not trying to still be this person, you know? I get a lot of keynote requests still in the museum world and I just say no and I send them to other great people. And so I feel like also this element of like trying to not be attached, because I think also maybe it goes with the like freedom to leave thing. I've never wanted to feel so attached to a job or a version of myself that I couldn't feel good about chucking it. You know, like when I ran this museum, I always had in my mind, I can't stay for more than 10 years.

And I left after 8. And I thought that was about right because I felt like when you start to stay too long, you feel like the organization is you and, and, and vice versa. And without— and you start to clutch onto it in this way that it feels unhealthy. For both you and the organization. And maybe not everybody would feel this way. I certainly have mentors who I really respect who've worked at the same place and built it and built it for decades.

But I think for me, there's a sense that of, of non-attachment that like, don't take yourself so seriously. And I think a lot of that comes from watching my dad, like my dad, his, you know, his rock band, the pinnacle of his career, the biggest crowds they ever played in front of was when he was like 22, 23 years old. And I saw how, like, in my lifetime, the crowds got smaller and the venues, you know, changed and there were fewer dates. And it's really hard to hold on to a strong sense of yourself if you're— if you are— if you've had— if you feel like your best days are behind you. And I'm not saying that my dad necessarily feels that way. But I think that I have always been resistant to painting myself into a corner where I feel like I have to keep doing this to keep being seen as valuable or worthwhile or whatever that might be.

[33:21] Paul: Yeah, it's— I've experienced similar emotions. I was a strategy consultant in New York and Boston and very impressive on paper, but felt very empty inside. And I walked away. I freelanced for a little, and then I sort of like just stopped trying to make money for like a year, lived on extremely low amounts of money. And I felt so bad. And this is the thing that I've tried to talk about in my book, which is that like you might actually feel terrible by like taking a new path, but it might also be worth it.

A thing for me was just like, I think I had this just like deep sense that like I was on a path even though I couldn't convince anyone, I couldn't tell anyone I was on the right direction. And I sort of hid from the world in a similar way. But did you have something similar in multiple of your reinventions? It's like this deep sense of like, even if I think it's stupid rationally, I still need to keep going on this.

[34:29] Nina Simon: Path? I think, you know, you said this line that I gave you in the very beginning about, you know, making choices to disappoint my mother, which is not on a human level true. My mom is incredibly proud of me and loves me deeply. And I think that I, since I was very young, have made some choices that were not the right choice. And so I think that That almost is pre-insulating, you know. Um, when we got married, like, you know, my husband and I left living in downtown Washington.

We— even when we lived in downtown Washington, DC, we lived in these weird houses with 10 people. Then we moved out to these cabins in the wood, off the grids, in Santa Cruz Mountains. And like, by the time we were ready to get married, I mean, we, um, we self-officiated. We did 7 weddings over 7 weekends. So like, people could— we set up this website, you could come to the that you wanted to come to because we wanted to have a small wedding but invite everybody. And so, like, there are so many incidents in my life and my husband is— but he's a huge iconoclast.

I mean, I will never forget, like, when he was young and I was younger, you know, he was in some MIT 30 Under 30 tech review thing and he shows up to this event where everybody else is wearing a suit and he's wearing these ripped jeans of his ex-girlfriend's and this big beard and long hair and a cowboy hat. And I— there was a part of me, like this middle-class Jewish girl part, that was just like, oh my God, I could never do that, that's so embarrassing. But he was like, you know, all the people who wanted to talk to me knew who I was, and the people who didn't want to talk to me, I didn't want to talk to them either. And I think that being with a partner who has that way of looking at life, and a lot of the choices we've made, it's just like we've pre-qualified to our families that like we're doing weird shit. And frankly, we also have had some real successes on paper.

You know, I was the Santa Cruz County Chamber of Commerce Woman of the Year, you know, one year. I mean, so I think that there have been enough of those atta girls from, like, from establishment to feel like the balancer. I think it would be much scarier. And I have artist friends who I really admire who have not had that. Like, you know, when I was in my late 20s, I was kind of an it person in the museum world. It's like you stumble on that kind of luck, it's like you can't— like, if you're not going to choose to use your success to then screw up and take some risks, then you're— then you are like way more cowardly than somebody who has never hit it.

Like, you know, once— once somebody gives you a weird plaque that you don't know what to do with in your house, like, after that point, you should be taking some risks, I think. And so I guess that I didn't feel— I always felt like I was choosing, uh, both that I was choosing from a place of confidence because I had had success in the past, but also I was choosing, you know, my own freedom to, like, my own weird life over anybody else's idea of what it should be.

[37:37] Paul: I love this so much. Like, I feel like my brain works very much the same. It's like, well, I succeeded, I might as well blow it up now. Like, Yeah, but as you must know, this is not a common, commonly held orientation toward the world, right?

[37:52] Nina Simon: Like, right.

[37:53] Paul: Have you ever successfully convinced anyone this is a better way to look at things?

[37:59] Nina Simon: I don't think I've ever tried. You know, it's interesting.

[38:01] Paul: Yeah, I don't really try either.

[38:02] Nina Simon: Like, you know, like, I'm a vegetarian. I live off the grid. I shit in buckets. Like, and I have spent 20 years trying to convince— or not even, I stopped trying a long time ago. Like, The weirder the choices I make are, the more I feel like there's no reason to try because, A, you know, I have a lot of friends who love me who are much more conventional. And so they get to come to our weird home and whatever, and they see that this is a loving, weird choice.

And but I don't presume I guess what I care about and what I try to convince my friends to do is to not do things that they hate and, or not do things that they feel they must. And I always will remember this one couple I used to rock climb with who he really wanted to start a business, but he felt like his wife and he, they were just too risk averse to, for him to do this thing he really wanted to do. And I still remember that even though I don't even remember his wife's name today. Because I just remember how awful that felt when I heard it and how I felt like, oh my gosh, that, that's not, that's not okay with me. And that would feel very small. And so I think that I want to convince people to live their big, wild lives, whatever that might mean for them, and, and not to live this particular weird life that I'm living.

[39:37] Paul: I love it. So I've done a ton of like thinking and writing and conversations around work, and people have these strong work scripts, but people have even stronger scripts about how you should realign your life with a traditional path as soon as you have kids. What do you know about this?

[40:01] Nina Simon: Well, this also— this has been a path my husband and I have been on, an unusual path in this regard for a long time. And it started out— we always felt that every stage of life at which the conventional theory is that you should separate yourself from community, particularly from your friends, we felt like was a time to double down. So, you know, a lot of people, it's like once you get serious with your boyfriend or girlfriend, you move in together away from other people. We wanted to live in group houses with each other as a couple. A lot of people, when you get married, you buy your own house away from people. We bought this compound where there's, you know, 20 people living in these different cabins.

Um, we, you know, we had a kid, um, and we, we knew we were going to be a one-and-done couple. Um, I feel like I really respect my friends who have a lot of kids, and, um, Holy shit, is that a lot of work? And does that not allow you to at least be the kind of independent people we want to be? And, um, and we like to take the philosophy about kids that we take with dogs on this property, which is you have one that you're responsible for at night, but during the day they can all run around with each other. So, um, there are a bunch of families here. My, my daughter goes to regular school, uh, public school, but after school You know, she is hanging out with the kids who are 2 to 10 who live here.

There's right now there's 6 of them. It changes from time to time. And then the most radical choice we made last year. So we live in a 350-square-foot cabin. It's one room and there's a separate building that's our kitchen. And for the first 7 or 8 years of my daughter's life, she lived in that room with us.

We slept in the loft. She slept downstairs. And then, and we always said, oh, we gotta build a, a, a bedroom for her. But it kind of always felt like complicated, expensive, a lot of different things. And, and she was happy to be with us and so fine. And so, but right around when she started to get close to 8 years old, she wanted her own room.

Great. We wanted her, we also wanted our own room. And, and a 2-bedroom cabin right next door opened up. The family that lived there moved out and we looked, we talked to a couple families and didn't work out. And then my best friend, who is a 26-year-old math and health teacher, high school teacher, she was like, gosh, Nina, I would really love to move up there, but I know you want families. It's a 2-bedroom, da da da da.

So my friend rented that cabin, and the second bedroom is my daughter's. So we have this sort of extended household with my friend where my daughter's bedroom is over there. She gets up in the morning when her alarm goes off. She gets dressed, she comes over here for breakfast. Like, she's very clear this is her house, you know, with us, but she sleeps over there. My best friend has a cat that she loves sleeping with the cat.

They sometimes have like naked dance parties in the house. Like, it's really sweet for her to have another adult in her life. So we have made some unusual choices. And again, like, we have a phenomenal kid. Like, she, you know, um, is doing great. And so I think that anytime Like, my parents have been like, hmm, like, even we named our kid Rocket, and I remember when we were in the hospital and you signed that thing, we were just like, they're gonna just let us do this?

Like, um, but we wanted a name that was unusual but easy to spell and pronounce. And, um, and so there have been a lot of things like that. She gets a lot of clothes at clothing swaps. Like, she dresses totally wild in her own way, you know. And anytime that sometimes even I'll— it falls in for me sometimes where I'm like, gosh, could you brush your hair? Because it's picture day.

And, you know, and those feelings come into my head. And then I'm like, she shows up on picture day and she's wearing like 87 different green items because that's what she wants to do for picture day. And it's like, you're doing awesome. And I think also the other thing about the traditional path is people cling to it from the safety perspective. But at least, I don't know, the people who most push that on me are my— or, or where I get that most subtly are my parents. And as they have had friends whose kids have gotten married or had kids, they're just seeing how we're a loving family that's raising a great kid, and that that matters more than a lot of other BS.

Like, even, you know, we don't really do screen time. And at first my mom was like, well, how is she gonna learn? I'm like, I'm pretty sure she's gonna have plenty of access to screens. And now, of course, my mom's like, oh, she's I'm so great at talking to people and engaging people, and I see these other kids and it's sad, you know. So I think that, um, we— yeah, we've never been uncomfortable doing— I, I think we live in a pretty principled way. Like, we think all the way down about what matters to us, and then we're pretty comfortable even if that doesn't fit, uh, what others do.

That said, there have been a lot of hacks along the way. You know, when I was pregnant, I was running this museum And we decided that we wanted to know the gender, but we actually decided that my husband would learn the gender and I wouldn't, because every single day, like volunteers, visitors, old ladies, donors were saying to me, oh, you know, when are you due? What are you having? And I wanted to be able to say, I don't know, to just like shut down any bullshit conversation about their weird ideas about having a girl or having a boy. So definitely, like, there are ways that we played with the traditional thing to kind of get out of it. And whereas like a really strong, like a more iconoclastic person would be like, screw you, I, you know, I'm just not going to engage on this.

[45:37] Paul: Yeah, it's such a subtle balance of like just boldly going against the default versus like actually just putting in that deep thinking around what you actually want. Like, the way I think about it is like Okay, I'm not like rejecting a traditional job. What I'm doing is starting with like the principle of like, okay, I want to be connected and feel alive generally in my life. Can these different ways of structuring work fit into that? Right. And sort of flip it on its head.

And like from that point of view, I don't really care what other people do. I just find that a lot of people aren't really thinking that deeply about how they're structuring their life. Sure.

[46:17] Nina Simon: I mean, it can also be deeply annoying though, right?

[46:20] Paul: Like, oh, we're very annoying people. Yeah, this is, this is a home for people like us though on this podcast.

[46:28] Nina Simon: My husband's one of those people who can't really sleep easily with other people, and according to him, 10% of people just really need their own bed. And, um, we spent years arguing about this, and even I would like fall back on these like This is what people do. And he's like, well, we're not like other people. I'm like, okay, but could we be like other people in this one way? You know, and we have eventually found a strategy. Yeah.

[46:51] Paul: This is the strategy. King-size bed.

[46:54] Nina Simon: We went for the Tempur-Pedic, was our— but before that strategy, there was the I sleep on a bed and you sleep on the floor strategy. I sleep on a bed, you sleep on the roof. I mean, we had many different strategies before the Tempur-Pedic queen-size bed. Yeah.

[47:07] Paul: Yeah, I'm only saying king-size bed because we actually went through this debate. Like, I think my wife is one of these people that just like can't be around other people while she's sleeping. But it worked. Yeah, like enough space. But yeah. What do you know about like what are some of the like meta lessons you've learned about just like reinventing yourself, rethinking your path, like Are you better at it now?

Hmm.

[47:39] Nina Simon: I think that— am I better at it now? I think that I have gotten better at identifying when I need to leave. I think that there's a lot of, you know, that's a place where I think there's some very confusing messages, particularly in kind of the startup world around, you know, do you need to stick it out at all costs because that's how you break through, or do you need to fail fast and move on and do something different, you know. And so I think that I've gotten better at figuring out, at least for myself, what that looks like. I think that I have gotten more comfortably reckless about my own reputation, which has been like a pleasure, because I think that for years I felt not so much that I was like carefully constructing it, but that I was very like mindful about everything I posted, everything I said. What did I wear to conferences?

I It's funny because I'm somebody who— I don't wear makeup. I don't— I'm not very into clothes. But like, if I have to give a keynote at a conference, I get like in this weird loop about like, I want to be myself, you know, I want to kind of say fuck you to the conventions, but I don't want anybody to be shut off by my message just because they don't like that I'm wearing a t-shirt, you know, like, and I think that's particularly strong for women around appearance. And so I think that some of that stuff has been tricky. And frankly, it's just a little easier as you get older and people care less about what you look like. Um, but, um, I think that I actually, you know, Paul, I really, I feel like, um, so in 2017, I opened this public plaza project in downtown Santa Cruz that was attached to this museum I ran.

You know, it was like this $5 million project. It took many years. It still exists. And I think that This sounds very— or I get it about sort of colonizing space, like building a place in downtown Santa Cruz that exists that I made where it is a zero to one and it's physical, it's concrete, and I can bike by there and see it. It's like after that, sort of like, I'm good, I made this thing. And I felt the same way about the first book.

It's like, This is a thing and it is beyond me and other people are engaging with it. And I think that a couple of those go a very long way to feeling some solid, solid sense of I'm good. Even if I'm throwing away this job after X amount of time, I'm good. Even if I'm walking away from a startup I started just a couple of years ago so I can help my mom. And I think that those concrete objects almost become totemic as these things that you can rest on when everything else is ephemeral and is day to day. And so one of my closest friends, somebody I absolutely love, I think has really struggled because it's like those markers.

Even I got married pretty young, you know, I think some of those— I have a kid, I have a home, you know, those things are quite traditional in a lot of ways, but they go a long way for me to giving me the comfort to make many other choices and to feel like there still are these things that I could rest on that both make me feel comfortable but also are kind of traditional markers that are legit.

[50:56] Paul: It's such a powerful frame. I think letting go of the— it seems like you're really good or have developed a capacity of letting go instead of sort of letting the next chapter emerge. And I sense like I almost sense this could be a powerful thing for you. Like, there's a whole generation of people who overly define their lives around work and have enormous wisdom, but don't know how to shift into a new mode to share it. And I just sense that culturally now. And I do wonder how we sort of like unlock that.

It's a big question.

[51:34] Nina Simon: Yeah, and I think also, you know, for me it was blogging, but for, you know, podcasting, there's different practices. I think doing something where I was creatively delivering imperfect product a couple times a week and doing that for just years and like learning out loud in public on the internet, which I think actually has gotten much scarier now than it was even 10 years ago in terms of how quickly, you know, an imperfect thing can really be taken badly. But I think that that experimentation out loud is kind of like a small way to keep exploring. And for some people, it might be cooking meals they don't quite land, or like making, you know, crocheting lumpy things or whatever. But I think that like daily practice with imperfection, failure, struggle— I've also always been an athlete who's really been into like stupidly hard sports.

And one of the reasons I like it is like if you're choosing at 7 in the morning on a freezing day to like I don't know, carry 50-pound sandbags through the ocean and, you know, do burpees with them. Like, it is clearly only your choice that is making you do— like, nobody is making you do this. There's no reason to do it. But I feel like it conditioned me a little bit to like, A, I can give up when I need to give up. But B, I mean, life can't be that hard if I can do this weird hard thing. Like, and And how hard could that meeting be if you, like, I don't know, carried some guy on your back for a mile?

I don't know. So I feel like finding ways to practice doing things that are hard or imperfect or failing and just being— showing yourself again and again that nobody dies when you do that. Like, nothing, you know? Yeah. Unless you're, you know, I listened to your episode with the doctor, like, unless you're a doctor, like, for the most part, like, failure is something that you can learn from and that many of us don't really want to learn from. And so, like, aggressively pursuing that has been something that I think helps support that.

[53:41] Paul: I wanted to ask you about this thing you sent me before, the fiction that we have one story about the path that brought us to this moment. I think this is a hard tendency to avoid because people ask, what's your story? How, How'd you arrive at this point? But I think in writing my book about my path, I sort of discovered this same thing you're pointing out, which is like, whoa, I don't— I can't— I can explain it in one way and show you what I was feeling and thinking at the time, but I don't really know how I got here.

[54:13] Nina Simon: Yeah. And I think you're right. And it's actually a beautiful thing about people that we are so able to construct backwards narratives from where we are right now. And I mean, I had to do that, you know, when I wrote this novel. When you are trying to get an agent, you have to like tell something about yourself and they don't care about anything that isn't related to what you're writing. And so I'm like casting way back and starting to pull out like, I guess I kind of always was a writer.

And but definitely that's not the story I was telling 2 years ago when I was, you know, raising money for a startup or whatever. And so I think that I learned a lot from— there's this political strategist named Marshall Ganz who did a lot of work with the Obama campaign. And, okay. Yeah. Yeah. So I went to a workshop maybe 6 years ago at a different job I was in that was about how to do a story of self.

Right. And there's this like formula where it's like you start with the story of yourself. Like the first minute is story of you. Second minute is story of us. So You know, I was a kid who was picked on. We've all experienced what it's like to be picked on.

And then the third is the story of now. The third minute is, so let's go out there and let's build a kinder world or whatever. And one of the things they teach in those workshops is you probably have a personal anecdote for anything that is deeply held that you're working on now. You probably have a story that can— that you can go back to. And there were people in the workshop who were really uncomfortable, myself included, about, well, but what if that's not my the story? And they're like, no, no, no, nobody has a the story.

And probably if you picked a different value or a different project you're doing, you would pick a different story. And so I think that I both appreciate and definitely use a lot of times single narratives to be able to drive to everything's been leading to this moment. But of course, everything's been leading to all kinds of moments. And I think that There is, I think, another, like, formative moment for me when I was an intern at the Boston Museum of Science. I was like 19 years old, 20 years old. I met this director who seemed impossibly old to me at the time.

She was probably 50. And she was saying to me that working at the museum— and she was like VP level— was her third career. And she thought she had one more big career turn in her. And I remember looking at this person and being like, what? I thought you had to work your whole life to be where you are right now in doing exactly the same thing. And so I think also, it's also about the backward stories we hear from the people older than us, you know?

And so I think that when we can query and dig in, when we're— whether we're talking to a grandparent or whether we're talking to a mentor about what else were they doing or where else were, you know, if you weren't doing this, what else could you imagine? I think that so many people actually, you know, if you think about like the multiverse kind of concept, like I think so many of us are just a half step away from our feet on very different paths and, and that there's beauty in that. But it's, it's inconvenient if you're trying to get a tight soundbite about what you're doing. And it's frustrating if it's Thanksgiving dinner and your cousins are like, well, what the heck are you doing now, Paul? Like last week it was this, you know?

And I think you've— you're— I mean, you're even solving this in a different way of like creating this meta-narrative around the multipath or the pathless path, which is cool. And that's something I had never thought about before I engaged with some of your work.

[57:42] Paul: I appreciate that. Yeah, it's— it's— I didn't realize how convenient, like just saying I'm on a pathless path would become. But yeah, some of my family members will make fun of it as a way of like, just, they used to just say, oh, you're just unemployed. But at least now they're like, oh, you're on a Pathless Path. But comes with the territory.

[58:05] Nina Simon: Yeah. And I would want to come back to what you, I think actually, I think the narrative that needs to pull out more with the Pathless Path or the multi-path is like you brought up earlier about some of the hard feelings and how sometimes jumping to something that you, you're really excited about can feel really shitty and There's this book called Transitions that's from the '70s that's about, you know, making big changes in your life. And one of the things he talks about in the book that really resonated for me was like, especially Western or Americans, it's like if you're on a trapeze, you want to jump from platform A to platform B and like, boom, you're in the new life, whether it's the new relationship, the new job, whatever. And his argument is there's actually a lot of time and confusion and beauty and heartbreak and amazing things that happen in the swing.

And sometimes you swing to the platform and then you swing back before you can get all the way, or sometimes you get stuck in the middle. And I think that kind of having grace for yourself if you're in that middle swing, if you're saying goodbye to something and you haven't been able to fully mourn that, or you may not even be able to fully mourn that until you've been in the new thing for a year, you know? And so I think that having grace and appreciation for the fact that we don't jump from path to path. Like, there is some, some, you know, bushwhacking or swinging or whatever metaphor you want to use in between. And that sometimes that's beautiful and sometimes that's hard and sometimes it's scary, but it's real. And if you skip it, you're only screwing yourself.

[59:36] Paul: Yeah, it's— is this the William Bridges?

[59:40] Nina Simon: Yeah. Have you read that book?

[59:42] Paul: I have not. I was just finishing another book called Life Is in the Transitions by Bruce Feiler. And it's sort of— I wonder if he's just like sort of remixing the book, but he talks about the messy middle, right? And how you can't fast-track that. That one's amazing. Highly recommend that.

Cool. Aida, who I interviewed, recommended that book and it's been awesome. But yeah, I'd love to shift to a couple rapid-fire questions before we wrap up.

[01:00:15] Nina Simon: Sure.

[01:00:16] Paul: Do you, do you have a path role model?

[01:00:19] Nina Simon: Hmm. No. I'll try and be brief on this, but I have— I would say I have an anti-role model, or rather, sometimes I think I want something and then I realize that Somebody taught me a long time ago this strategy of like, when you think you want something, write down all the things that would have to be true in order for that to actually happen. And I think that I was once at a mentor of mine who's not a PATH mentor, a role model. I was at her 30-year retirement party from this amazing nonprofit that she started that grew incredibly and really changed education in the U.S. And I was at that retirement party and there was a part of me that really wanted what was happening.

People were making silly PowerPoints poking fun at her and talking about different decades of the organization. And I felt this, like, sorrow that I felt like I wasn't going to have this. And then I realized, like, you don't want the 30 or 40 years that leads to this moment. Like, what would need to be true to get to this moment is not something that would make you happy day to day. And so I think that I try when I see achievements that are not— that look shiny or beautiful or loving or whatever, I try to ask myself like, but would I want the things that lead to that particular form of an achievement? And the answer is usually no if it involves, you know, dedicating your whole life to one thing.

I also was talking to a guy once who I really respect who runs a consulting business, and we were talking— it was after my last book did very well and I was giving a lot of talks and he said, you know, you're becoming really good at telling this one story. And if that works for you, that's great. And actually, the people who are most successful at making change on one topic do that, and they just hammer it for years. And he said, you know, that he was too much of a dilettante and a generalist to want to be that way. And that was an interesting— that was like a flicker for me of like, oh yeah, I identify with that. And I don't know that I want to keep maximizing on this one thing.

[01:02:22] Paul: I love that. I'm gonna try use that exercise. It's, it's so helpful.

[01:02:27] Nina Simon: Yeah.

[01:02:28] Paul: Have you been inspired recently by any specific books, podcasts, videos, things you've stumbled across?

[01:02:39] Nina Simon: I mean, I think that the two things that helped, that inspired me most in the last few years around kind of making big changes One is working with a coach from Reboot. Super expensive.

[01:02:50] Paul: Oh wow. They're great.

[01:02:51] Nina Simon: Super worth it. Yep. I mean, and, and if you're in a nonprofit, you know, it can, it can be more affordable. But there was a transformative— the year that led up to me leaving my startup when my mom was sick, I didn't know obviously that that was gonna happen, but my coach Jeff Riddle, I mean, it was, he was so instrumental to that. And then the other is, um, um, I went to a workshop put on by Zingerman's, which is a deli in Ann Arbor, Michigan. Actually, I went with Nick Gray.

Yeah. And they, so the guy Ari Weidenberg who started it, he runs this one 2-day workshop about visioning. And it's just this very simple technique of creating a vision for where you want to be, you know, 5 to 10 years from now. And you write it very specifically from the perspective of, you know, it's 2027 and I'm walking with my kid into kindergarten for the first time, or, you know, it's 2035 and I'm up on stage as we're giving out these awards, or whatever it might be. And that technique really has helped me, and I continue to use it all the time. It really helps me when I'm at the kernel of something that feels pretty uncomfortable and unsure to imagine myself on the other side of having succeeded doing it.

and I'm often surprised by what I find myself writing about. And, and when I've done this visioning, like, it's shocking how fast I end up actually going towards that future, much faster than even I wrote when I thought it was a totally bananas thing. So I really recommend the Zingermans' vision. I mean, envisioning is obviously a pretty generic strategic activity that you can do, but I— spending 2 days working on that was very special.

[01:04:37] Paul: That's great. Good sandwiches too.

[01:04:39] Nina Simon: Yeah, great sandwiches. Yeah.

[01:04:42] Paul: If you could go back in time and whisper or incept or plant one idea or phrase in your younger self's mind, what might it be?

[01:04:53] Nina Simon: It's okay to stand up for yourself and, and you can be successful and value yourself. And I think that I've learned a lot in the last couple of years from some of my colleagues around, you know, how to be clear about boundaries, how to, you know, and I think that there were a lot of ways I was just always looking to please or looking to be as valuable as possible to an organization. And I still, I would— there's no way I would say that person don't hustle. I mean, I firmly believe that when you're young, like the thing you can offer is that you can come in earlier and stay later than everybody else. And like, and I think that's a great thing. and I was just so scared sometimes to, to be clear about something that wasn't working for me or made me feel disrespected or wasn't enabling me to do my best work.

And so I would, I would tell myself to have more confidence about that.

[01:05:54] Paul: Amazing. Where can people learn more? Where can they check out the emerging crime writing and info around that?

[01:06:08] Nina Simon: Well, I'd usually say the best place to find me is on Twitter. I'm Nina K. Simon. I don't know if that'll still be true, you know, when— I actually, I think Twitter's gonna continue. But anyway, so I'm @NinaKSimon on Twitter and Instagram. And then, but my website where I feel confident I will always be is just ninaksimon.com.

[01:06:30] Paul: Amazing. It was a delight. I will likely be hitting you up, uh, for some unconventional parenting advice and all the wisdom I can soak up from you. But appreciate, uh, the conversation today. It was super fun and, uh, really inspired by your journey.

[01:06:47] Nina Simon: Thank you, Paul. I, um, would— I always love to support people who want to, you know, live your values as a parent and in your life and Um, and there's a lot of great ways to do that. And, you know, we often have people, we have some friends who've said, when I want to do something, uh, that my parents will think is nuts, I tell them what you did. And then, um, and then what I'm planning sounds way less crazy. So I'm also always happy to be an example of like, well, at least we're not, you know, sending our kid to live with a 26-year-old. And, uh, so yeah.

[01:07:23] Paul: Perfect. All right.

[01:07:26] Nina Simon: Thank you. All right.

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