Chris Wilson | Designing a Life That You Don't Need to Escape From

Chris, welcome to the Unmistakable Creative. Thanks so much for taking the time to join us.

Chris Wilson

Hey, thank you for having me a big fan of the show. And it's, it's honestly, uh, it's, it's pretty surreal being on the show after being a listener for as long as I have. And I mean, we kind of briefly talked about it earlier. I think what sticks out to me is the fact that you are such a, like values driven person and the people that you get on here really do, I would say align with the kind of like business that I'm trying to create and just kind of the work I'm trying to put out in the world. So

Thank you for giving me the opportunity to be on the show.

Srini Rao

It is my pleasure. I mean, to me, that's the ultimate compliment when somebody who's a listener becomes a guest, because it means they've actually done something with all the things they've learned. You know, I always jokingly say if I could actually implement every single thing I've learned from my podcast guests, I'd be a billionaire with six-pack abs and a harem of supermodels that might, you know, on speed dial. But that's not reality. So before we get into your work and your business, I want to start asking, what did your parents do for work, and how did that end up shaping where you've ended up with your life and what you've done?

Chris Wilson

Ha ha ha!

Chris Wilson

So my mom kind of did a whole mix of things growing up, but she ended up getting into social work and working with everything from homeless people to mental health, to addictions, kind of the full gamut of kind of like working with people. And I would say she was and continues to be kind of one of my biggest inspirations in that like she was in her late.

uh, fifties going into her sixties when she went back to school and got her masters in social work. So, I mean, for me that kind of instilled that idea of like lifelong learning where like you never really you're continually growing and it's to me that's something that I've really taken from my mom and for my dad he, uh, he was a journalist. Uh, he wrote kind of like his own, uh, column for

about 30 years and it was really in a way it was social work in the same way that it was very kind of people-centric writing about people in our city and he kind of instilled the idea of well he wasn't an entrepreneur very much kind of like how he modeled his work very much was and a lot of that came down to me it falls in with like cal newport wrote a book called like be so good they can't ignore you

And that very much kind of was instilled in me through my dad as well, where like, he focused so much on his craft and becoming a better writer that it allowed him to really create the kind of role that he wanted within the organization that he worked for. And it gave him the opportunity to do what he wanted to do, work when he wanted to work and write about the things he wanted to, because he had reached such a level with his writing that he became impossible to ignore, that he now had opportunities available to him.

So I had two really great parents for instilling a lot of those values in me. But I think I shared with you too, like that was part of what my struggle was too, in that like I dropped out of high school in grade 11, both my parents are university educated and school just didn't work for me. It just did not mesh at all. I didn't learn that way and it made me feel stupid and I struggled for a long time, just

Chris Wilson

in that sense of like seeing my parents and their success and not really knowing what I wanted to do with my own life.

Srini Rao

Yeah. Well, I want to come back to the dropping out of high school thing, but you mentioned your mom doing social work, working with homeless people, people who have addictions. And I wonder how that influenced and shaped your sort of values in terms of serving people. And then as far as your dad, Yoz, I think that was a perfect setup for something we were talking about earlier before we hit record was this whole concept of influencers and

Srini Rao

can't seem to know who it's from, is that as a society we have a responsibility to stop making stupid people famous, which I think actually dovetails nicely off of the work of your dad. So, you know, he predated this whole era of, you know, quote unquote influencers. And I'm just, you know, curious like what he, you know, how he influenced the way that you actually work based on that perspective. Because I, in one way, I'm kind of glad I'd never heard of you until now, because that tells me you're not sitting around wasting your time on social.

Chris Wilson

Yeah.

Chris Wilson

Yeah, I mean, I took myself off social media back in 2016 and not something I miss at all. And I mean, I've been somebody who's kind of struggled with like addiction and mental health throughout my life. Especially kind of mental health, like I'm bipolar, chronic depression, and I very much saw how much those things really affected my mental health.

from a comparison sense, from a just, it just felt toxic. And when it came down to where I wanted to kind of like, develop connection and develop kind of, I guess community, I realized that those weren't the places for me. I realized that for some people, it does give them that, but for me it didn't and I think my life's better as a result of not being a part of social media. I mean, it's meant that.

It's been a little more challenging to build a business, but I think part of that is I didn't necessarily have great role models as far as people that were developing businesses without the use of social media, but I've kind of been able to connect with people over the last couple of years that really do role model that. And a lot of it, I mean, you asked that question about my mom in terms of those values, and I think what really stuck out to me is kind of like the human-centric kind of like...

community focus of doing that kind of work very much reinforces what I want to do and what I kind of have kind of created through my newsletter and being able to connect with people not just in like snippets but have like actual communication and I think that's something that to a great deal has been lost and I think having parents like I have has really like instilled the importance of

those things of like meaningful communication and understanding that like everyone has a story. Like it's not like anybody chooses to be homeless or addicted to drugs and kind of like strung out and disconnected from their family. Like there's stories behind why people are in those situations and being able to kind of like from a deep rooted sense of empathy, understand those things and feel what they're going through.

Chris Wilson

I think has made me a better writer and better able to connect with others because almost in that sense of like how you name this, like an unmistakable creative to me is very much like alignment with your values and being uncompromising on those things. No matter what kind of comes up for you is recognizing that sometimes it means you're not going to be able to make say like the easy decision. You're going to have to make the challenging decision that really kind of like pushes you to the boundaries of what you feel comfortable doing.

Srini Rao

Yeah, I mean, I often based on values will sacrifice metrics for a good story. Um, uh, one thing that I wonder about your dad is what, you know, particular habits in terms of writing you picked up from a 30 year career journalist that you see sort of lost in the world of, you know, rapid feedback and quick social media updates.

Chris Wilson

Yeah.

Chris Wilson

I think really like the time it takes to sit down with someone and have a conversation and really like behind everything is just curiosity. Like what makes my dad a fantastic writer and like really a great communicator is just like he's super curious. Like oh that's interesting. Like how did you end up in that role? Like what did that mean for you taking on that role?

And like, just asking almost like in the same sense of like a coach, right? Like you're just trying to unpack things. And I think that's something that can be lost when you're not necessarily communicating directly with the person is. You can't get to the root of things. You can't really kind of unpack things down to kind of like the idea of like the first principles behind something. Like why, why is that kind of like, why that person does that? Like you and I were talking a little bit about like the.

I think people can get lost in personal development and like trying to implement everything and well, if I listen to Tim Ferriss's podcast and I listen to this person, then I got to do this and this and this. I got to wake up at 5 a.m. But some of it I get back to like, well, why does that person get up at 5 a.m.? Maybe they have a four year old at home, so they need to get up at 5 a.m. in order to get an hour's work in before the kid gets up, right? Where it's like, it's not necessarily prescriptive unless like

Srini Rao

Yeah.

Chris Wilson

That's the medicine that you specifically need for your life.

Srini Rao

Yeah, absolutely. I think it's fascinating that we're talking about communication. I don't know how old you are, but I'm 43, about to be 44, and we grew up in the 80s and late 90s. I remember the idea that you could see somebody's face on the other end of the phone was some back-to-the-future shit, you know? And it's kind of hilarious because I almost feel like, you know,

Chris Wilson

Yeah.

Srini Rao

the way we communicated has actually become the opposite of sophisticated. It's become less sophisticated. You know, I said, you know, the way we use our devices is the equivalent of handing cavemen iPads and them choosing to still write on stone tablets.

Chris Wilson

Yeah, yeah. Well, I mean, I'm 39 in June, so I very much.

Srini Rao

Okay, so you probably know then what I'm talking about.

Chris Wilson

Oh yeah, like, I mean, one of my favorite things growing up to do with friends was prank calls. Like, like you, you can't do that anymore. And I, I think that is kind of like, as you said, like so much of that has changed where I don't think we have necessarily caught up with just the speed in which things are going. It's not necessarily an advantage. It's in the same way that like, there's a million different kind of like.

Srini Rao

I remember that.

Chris Wilson

to do apps and websites that you can use. But I've tried probably, I don't know, 50 different kind of like systems. And again, if you ask kind of like what worked for my dad, he uses just like a notepad that folds and like pops in your pocket. And I've defaulted back to that for the last like three or four years. My life is dramatically different where somebody...

Srini Rao

Yeah. Yup.

Chris Wilson

There's this one guy, Peter Drucker, and he talked about like, if you have more than three priorities, you don't have priorities. And that very much became clear when I was trying to use a lot of those systems where I was like, I'm just trying to manage too many different things. I need to simplify my life. Like what are the main things that I want to make movement on with my life and my career and just who I'm, who I am as a person. And if I can't capture that in this notebook, then I'm probably dabbling in too many things right now.

Srini Rao

I love that. So, you know, a quick detour. I got to ask you about the prank calls because I have a great prank call story, but I want to hear what your best prank call story is.

Chris Wilson

Ha ha ha!

Uh, well, I got kind of lucky in that for whatever reason, there was a, I don't know, it must've been a glitch in the phone system. So our phone number actually showed up as kind of a local college. So I could phone wherever and it would show up as this college. So we could often kind of really mess around with people and whether it's like, I probably can't repeat most of it in terms of like shit that we got into.

But it was a lot of fun. Like it was a lot of fun, just kind of, it was innocent enough, but it was something about it that I feel for a lot of kids that they don't necessarily get to have that same kind of fun in that like, my parents used to just send me out the front door and be like, okay, be back at sundown.

Srini Rao

Oh Yeah

Srini Rao

Exactly.

Chris Wilson

Right, you're riding your bike, you're playing in the forest, you're like going to friends' houses, I'm skateboarding, like I'm doing whatever I wanna do. No, I recently became a dad, I have a six week old at home. And that's one of the biggest things I struggle with, like thinking of technology where I'm like, ah, like there's benefits to it, but it's way too easy to find yourself consuming too much of it. It's in the same way that like,

Srini Rao

No cell phone to check in on you. Yeah.

Chris Wilson

I don't buy chips when I go to the grocery store because I'll just devour the entire bag and it's having a device in your pocket is very much like junk food. It's way too easy to just overly or over consume without having kind of like an idea of like what it's only a tool if you're using it as a tool. Otherwise it just becomes like a distraction from life.

Srini Rao

So I got to tell you my prank call story, which I may have shared on the show before. So we live in Texas. We're living in College Station, Texas, which is a small little Texas town with a university. And most of the Indians in that town were graduate students. And so just for kicks, like this was in seventh grade, keep in mind, this prank call lasted two years. It was an extended prank call to one person that we maintained for two years. And so basically what ended up happening

Chris Wilson

Okay, yeah

Srini Rao

you know, open the phone book and I looked for some Indian name and there's this woman named Mrs. Parshuraman and I was like, I grew up with Indian parents, I can, you know, fake an Indian accent. And so I pretended to be this Indian grad student. I invited myself to her house for dinner. Like I had this just extended conversation with her that lasted probably up until I was in ninth grade. It started in seventh grade. And then one of my friends started calling her and pretending that he was too. And then, you know, he didn't do as good a job with the Indian accent. So, you know, when I called her for the very last time, she's like, Oh my God, it's actually you.

Chris Wilson

Yeah, yeah.

Chris Wilson

Ha ha!

Srini Rao

I mean, it was the most ridiculous thing, but that's what you do when you live in a small Texas town and you don't have an iPhone to constantly entertain you.

Chris Wilson

Hey, kudos to you for staying committed for two years. That's impressive.

Srini Rao

Yeah, well, you know, that tells you how bored I was as a kid. But so let's talk about the experience of dropping out of high school. When you have two university educated parents and you go to them and you tell them I'm dropping out. What the hell is that conversation like?

Chris Wilson

You know what, again, that kind of speaks to my parents because I actually asked my dad not that long ago, we were on a bike ride together and I was like, what was it like having a kid come to you and say, like, I wanna drop out of high school? And he was like, to be honest, Chris, it was like one of the hardest things that I've had to kind of be a part of as a dad because I recognized that you were miserable and you were really struggling and like,

things weren't clicking for you. Like when I dropped out of high school, I was on my second high school at that point, just because I wasn't showing up. And when I shared that with my dad, where I'm like, I don't wanna be here anymore. And he was like, well, what's gonna happen is if you drop out of high school, like you're now paying rent to live at home. Like you have to get a job. Like you don't just get to sit at home and play video games. So it didn't take long for me

Dropping out of high school to realize that wasn't the life that I wanted like I was working at temp agencies and I was working kind of like these jobs that like Didn't provide a future to me and I saw some of the people in those jobs and I remember there was one guy in particular I was waiting out front of a temp agency early in the morning just to kind of see hey Can I get work for the day and the guy like looked at me and he's like, what are you doing here? and I was like well like I'm here to like

get a job. And he's like, no, like, why, why are you here? He's like, I get you're here to get a job. But he's like, I'm in my 50s. Like, I don't have a choice kid. He's like, you're fucking 16 years old, like, go back to school. And it didn't like hit me in that moment. Like I continued to kind of work those jobs for a couple months. But eventually, I did realize I'm like, this isn't the life I want. Like this isn't

I can't get to where I want to go in my future based on how my circumstances are playing out right now. So that kind of led to me going back to school to get my high school diploma that I went on to college and university and did all that. But like a large part of it was allowing from my parents standpoint to let me make that decision and let me own the responsibility of what that decision was really played out in the long run.

Chris Wilson

where I'm sure it would have been way easier to go, you're not dropping out, you don't have a choice. But to give me that opportunity and allow me to like take ownership over that decision meant that like I had to go through the consequences of that decision and see what my life could have been. And to be honest, it's made entrepreneurship a lot easier in that sense because a big part of entrepreneurship is like dealing with failure. Like my...

The first couple decades of my life was just like nothing but failure. So it's like when you reach that point, you kind of realize, Oh, like I can, I can overcome anything, just give me enough time. Like I'll figure it out.

Srini Rao

Yeah, absolutely. Well, as somebody who, you know, is still single and doesn't have kids, I am very curious about the entire experience. I've talked to mothers about this, but I've never gotten to talk to anybody who has a newborn or, you know, a six-week-old baby. What is the entire experience of seeing a child being born? Like, you know, how do you describe it? And then, you know, how does it change? Like, what is this sort of, you know, because I mean, that literally in my mind

Chris Wilson

Yeah, it's so when we originally talked, I hadn't had my kid yet. And I was very curious, right? Because I'm a very kind of like type A, high achieving like go-getter, like always something on my plate, but very much kind of like trying to design a life that I didn't need to escape from in terms of like how I built my business. And I really didn't know what it was gonna be like having a kid in.

To be a part of that experience and like, to literally watch like the kid come into the world was the most surreal experience I've ever been a part of. And I can't imagine anything else giving me that same kind of reflection on life. Like when her head popped out, my wife, Lindsay, she was just like, what's going on, what's going on? I was like, holy shit, the head just came out. And it's just like.

It's unlike anything you could ever imagine. Like, it was a great kind of realization for me of a lot of the things that I worry about, a lot of the things that I get overwhelmed by or anxious by, just don't matter. Like, they're not life and death situations. And to have kind of a kid and see that kid grow up and to kind of, it made me realize that I have more skin in the game now, when

When I think of kind of like what's at stake, not just for my life, but like the community that I want to be a part of in terms of like giving her kind of a future, right? Whether that's kind of like through climate change, through like, just responsibility of like sticking true to your values, like things like that have now taken on more of a meaning. And I think part of that was like, I worked with behavioral youth for quite a few years and like a cognitive based therapy program.

And that really did allow me to see just how impactful it can be to not just say things to kids, but to listen to kids and understand kids and realize again, from like a story sense, like everybody's got a story and being able to help them kind of like unpack what that story means and to kind of understand how some of that story can sometimes limit you. But even though it did help you for a period of your life to see that you can now.

Chris Wilson

Continue to kind of like write the next chapter of your life. Like as you said like there's that clear divide before and after so for me like it's been a really surreal experience that I've I Knew I was gonna love but I didn't realize I was gonna love it as much as I do and it's really kind of from a priority sense made me realize again, if family is a priority to me then a big part of that is being here for and recognizing that

Anything that I say yes to is now taking me away from potentially time that I could spend with her so it helps me really make decisions where I'm like Do I want to do a podcast interview and if it's if one like this? I'm like, yeah, I really do because it's I know I'm gonna have a great conversation We're gonna get into some interesting things and we're gonna talk about kind of Stuff that I love the idea of like potentially my kids listening to someday Because I think a big part of it is realizing that like you can

don't have to go on a linear path to get where you want to go. And rarely do I find like, quote unquote, like the successful people that I really do admire, it's not necessarily kind of like A, B, C, D, like it's like A to Z to like X to like, it's all over the place. Like there's no rhyme or reason to how they ended up where they are.

Srini Rao

Yeah, absolutely.

Srini Rao

Totally. Well, speaking of rhyme or reason to how they end up where they're at, how do you go from high school dropout to simplifier Y?

Chris Wilson

The condensed version was really the high school dropout put me in a position where I knew I didn't I didn't want to continue down the path that I was going down. But a huge problem was that like I very much viewed myself as kind of like stupid, dumb. Like my report card reflected, hey, like, you're not you're not the smartest kid in the world. And I really did take that on. And I think

for a long period of my life, it limited what I thought I was capable of. And it wasn't until kind of like my mid-20s where I found myself, I had just graduated university. I was living in a city I didn't wanna be in anymore. I was in a relationship where like she deserved much better from the person I was. And I had just lost like a cousin in a car accident and kind of like everything collided all at once. And...

That moment was a big one for me where I am today because it led me to going into therapy. And through therapy, I, I kind of got a diagnosis of like, Oh, okay. Like I am bipolar. I have depression. I have these kinds of things, not necessarily from a label that now like limits me, but like from an understanding, like I like to know things. So now I could start to dig into these things to better understand myself. Like I could kind of understand like.

Here's the operating system that's like running through my head. Here's some challenges that I might have. Here's where like I could run into issues when it came to thinking about things. And through the therapy, I was in a career I didn't want to be in. And she was like, have you ever kind of like thought about like volunteer? And I was like, no, not really. So she recommended a place and it was the, the place that I ended up working with behavioral youth. I volunteered there. Then I liked it so much that I made a career shift.

And through that career shift, I got into that. And then it kind of just kind of continued to kind of like. Every day I learned a little bit more about myself and what I enjoyed doing. And then I ended up with a program called like pathways to education in Canada. And it's sort of like, uh, identified as like high dropout rate areas of Canada where this program comes in and there, we almost acted like life coaches to kind of like help kids identify.

Chris Wilson

goals, we helped them kind of come up with money for going to college or university. And that role led me to then becoming like my own business and doing kind of starting as life coaching, but now I do more so kind of like writing and working with businesses. But it was kind of an interesting transition between each of those things, but it was exciting because it was each thing gave me almost like unlocked another door.

Whereas like, I like the idea of gamifying things and to see that I was kind of like leveling up in that sense of like, from a meaningful sense of like, oh, like I'm creating more impact in terms of like, just the individuals I'm working with, not on like a massive scale, but like people are benefiting from having conversations with me and working with me. There's something to this. I'm going to keep developing this and I'm going to keep growing and I'm going to keep learning. And I think that's where I am today is like.

Helping other people kind of like design lives they don't need to escape from through largely like how to manage your mental health. Cause it's like really at the end of the day, like you can be very successful and like have a lot of kind of like knock it out of the park kind of like accomplishments, but like, if you don't have meaning in your life or you don't really have fulfillment and your mental health is kind of out of control, then to me that that's a, that's a huge loss in life.

Srini Rao

Yeah, it's funny that you referenced that same phrase again, designing a life you don't have to escape from. I was like, oh, there's my title for the interview. So how do people end up in a life that they want to escape from to begin with? And how do they recognize they're in one that they want to escape from?

Chris Wilson

I find.

Chris Wilson

I think it becomes pretty clear. Like you're when you're not really clear about what you want in your life. Like one of the questions that I often ask is like, what do you want your days to look like? And if that blueprint for what you want your days to look like doesn't match your life, then you're going to have some friction, right? Like if you're wanting a very like Zen morning where you're waking up and you're journaling and doing meditation and then going to a yoga class, but like

Instead you're commuting for an hour and a half to your work and working in a cubicle, like you're going to kind of have quite a bit of friction in your life. And I think that's something that again, comes back to like the traditional school system is like, it does a really poor job of preparing you for life. Teaches you to be a great kind of like rule follower, but it doesn't necessarily help you decide what kind of life you want to live. And that's a, that's a tough part. It's like.

I think it's almost like the bottoming out idea, right? Like with an addict in the same sense, where it's sometimes we almost need to kind of like bottom out with our lives before we go, I gotta do something. I can't just like, I can't keep doing what I'm doing or else I'm gonna keep getting what I've been getting. And that's where from a personal experience, that's what I was getting. I wasn't making any changes. I said I wanted to do.

things. I said I wanted to have goals. I said I wanted to do these things, but I never actually did anything about it. And it that's hard. And I think a big part of that is like sometimes we're stubborn, especially men. We're horrible at asking for help. Like, I don't know about you, but like we grew up in a time where like nobody was talking about mental health. And like therapy, no, like you're not going to therapy as a man.

Srini Rao

Mm-hmm, yeah, totally. Well, I come from an Indian culture, so it's even worse. Yeah.

Chris Wilson

Yeah. So like tenfold, whatever I'm saying. Yeah. And I think like being able to ask for help is often the first step where it's like, I think that's a big part of what I've learned, uh, is just being able to ask for help and sometimes like that's not even necessarily like directly like reaching out to someone like for me coming across your podcast helps me realize it's like, Oh, there's other kinds of like misfits out there. I can learn a lot from these people. Like.

They were somewhere now they're somewhere different. How did they close that gap? And you're brilliant at kind of like asking those questions of helping us figure out kind of like, what are those like baby steps, right? Like let's unpack that. Cause it's very hard sometimes to look at someone and go, yeah, but they're so different from me. It's like, yeah, but like you weren't born that way. Like it took a lot of probably learning the hard way to understand how they got there and to see that like they're just like us.

really does give you almost like a vantage point where like you can step back from things and take like that 10,000 foot view and see that like, okay, like they had to climb a mountain to get where they are.

Srini Rao

Well, I think it's interesting you brought up asking for help and, uh, you know, you think about accepting help because I remember, you know, Christmas time, my dad and my sister were like, look, we want to help you, you know, clear some debt and a bunch of other things. And I honestly, like, I felt so ashamed about that. And, uh, my sister was like, this isn't to shame you or guilt you. She said, we want you to be free of the stress that, you know, you're dealing with these small things and clear them so that you can focus on building your business. She's like, this isn't something to feel terrible about. And she's like, you're in a position.

where we're privileged enough that you are able to get help from people who love you. That was one of those things that was really hard for me because that was like, oh, I'm not being self-reliant by accepting their help. It was something I... It really kind of did a number on my head until I finally realized, okay, you know what? You're helping and what goes around comes around, so I should accept this help right now.

Chris Wilson

So what gave you that perspective shift to move yourself from like feeling like, oh, this is something that I should be doing by myself. Like I need to struggle in order to get there versus like being able to accept that.

Srini Rao

Oof. You know, honestly, it was just a lengthy conversation in my dad's office with him and my sister. And I think what it was, was rather than seeing it as, you know, they're basically pitying me, it was looking at the, the perspective shift was really, okay, this is coming not from a place of pity, but from a place of service.

Chris Wilson

Hmm. Yeah. I don't know about you, but like, I think a lot of us that like have these kind of conversations, we tend to kind of find very quickly that like, we're our own worst enemies, right? Like, the things that we say to ourselves tend to be the harshest critic, right? And like, I think that idea that like people often kind of share, let's like, well, what would you tell a friend to do in this situation? And I'm sure if that was posed to you,

in that moment, like, what would you have said if that was advice you were giving to a friend who said, hey, like, my parents are wanting to do this. My sister wants to help me pay off debt. Like, what would you tell that person?

Srini Rao

you would probably tell them except that I remember a friend of mine, you know, had this conversation with me and it wasn't until he said, dude, because I lived at my parents' house for years and it was only when I met him that I finally became OK with living at my parents' house because he was right around the same age and he was living at home, building his business. And I thought, OK, I guess I'm not the biggest loser in the world for this.

Chris Wilson

Yeah.

Chris Wilson

Yeah. Well, I was the same that like, as I mentioned that period in my life where I ended up kind of like in my mid 20s going to therapy and like, that meant like leaving a partner who I had an apartment with and moving back in with my parents when like I was like 29 or 30. Like that felt like a massive failure, but it very much kind of set me up later in life to

I think be able to make some decisions and choices that weren't available to me when I did feel very stuck.

Srini Rao

So we alluded to people ending up in a life that they don't want to escape from. Let's talk about designing one that they don't want to escape from because I think that that's ultimately what people want. And the jump off point I want to use for that is you were talking about the trade off of everything that you do now as the result of having a daughter where every choice that you make is a trade off of not spending time with her. And the reason I'm curious about this

I did a lot of research. I was during Christmas talking to listeners, doing one-on-one interviews with them to kind of understand what their challenges were. And one thing that came up several times when I talked to particularly parents with younger children about creative work is that they felt selfish for making time for themselves or felt guilty for making time for themselves because of the very thing that you're talking about is that, okay, I'm doing this thing, but it's a trade-off in which I choose to do this instead of spend time with my kids.

as a sort of jump off point for this whole idea of designing a life that you don't want to escape from.

Chris Wilson

I'm glad you brought that up. I think that is something that from, especially from like a parent standpoint is sometimes you can feel like you have to kind of like completely dedicate your life to your kid in terms of like making all sorts of sacrifices. But I think one of the ones that really isn't effective is when we do it.

without taking care of ourselves. Like in that same sense of like the oxygen mask analogy, right, like what do they always say? Like put your oxygen mask on first before you put it on your kit. Otherwise you're depleted and you can't help your kid. And I think that's very much kind of reflective in life. Like as someone who has struggled with mental health for most of my life, I recognize that like, if I'm not getting exercise every day,

If I'm not meditating, if I'm not, uh, like doing some kind of like reading, whether it's listening to a podcast, reading a book, I very much find that like, I don't have the energy to give my kid, my partner, anyone I work with really kind of what they deserve and what I know I'm capable of. So, I mean, I think identifying, especially kind of like designing a life you don't need to escape from is like.

In the same way that like I used to, uh, I think I had like five or six different medications that I was on every day as a result of kind of like managing my mental health, I never questioned whether I should take those meds each day because my life was that much better as a result of taking those, but with the help of a doctor and over a couple of years, I was able to kind of like come off those medications, but I recognized that like there's certain other things within my life.

that act in the same way as those medication. Like if I'm not getting seven hours of sleep a night, really affects my mental health. So that's a priority for me. Drinking two to three liters of water a day, another thing, I gotta do that. Like moving my body, like getting to that point of like treating those in the same way, of like those are medication for me. So I have to do those each day. And I mean, I'm able to be flexible with those things where it's like.

Chris Wilson

Exercise or movement doesn't necessarily mean that I have to go to a class and do an hour-long workout It could be walking my dog could be just like some push-ups like I'm able to kind of be flexible with things and like surf the waves of life rather than kind of feel like Super strict about things where it's like if I didn't do this. It's a failure What's like taking care of myself means that I can very much take care of my daughter and others

with more energy.

Srini Rao

Yeah, I mean, I think that it's funny because I also think that, you know, doing the work that you want to do as a form of self care, you know, I realize Danny Shapiro had this great quote in her book, Still Writing, where she said, you know, the one thing I know after years of writing is that when I'm not writing, I'm not well, the world around me is leeched of its color. That always stayed with me because I realized when I'm not writing, I am not a happy person. When I'm not working on some sort of creative project, I feel directionless and purposeless.

Srini Rao

hit or because I didn't have something to look forward to. Seth Godin talks about this often, people don't have this creative project that's next. Ryan Holiday talks about this. He always knows what's next. Ryan is sort of the ultimate anomaly because the guy writes a new book every year. I always jokingly say, I get a book from Brian and a week later the next one shows up.

Chris Wilson

Yeah, I think it's fair to say that Ryan's a bit of a freak of a nature when it comes to like his ability to continually output it. And I think so much of that for him, like when you listen to him talk, like he's also got a great podcast like Daily Dad, and he talks about like the ritual of those things, right? Like in the same way that he describes writing, I think you've described writing to me, like it helps me make sense of the chaos that's in my mind sometimes.

Srini Rao

death.

Chris Wilson

The ability to take that thinking and put it on paper is a huge benefit to me. Like it helps me understand my thinking in a way that's like incredibly like therapeutic, even if I didn't publish it, like it would still be very beneficial to me.

Srini Rao

Mm-hmm. Yeah. I mean, I always jokingly say I'm an average writer who writes a lot. So sometimes I write something worth reading. Yeah. But, uh...

So, okay, so we've talked about sort of the foundational basics of designing a life that you don't want to escape from, you know, sort of health and wellness, you know, mental health, physical health. Let's talk about the actual work. Like, how do you convert that into doing work that you want to do, whether you're in a day job or not? Because I think that if there's something I took away from what you told me about your dad is that you can create the life that you want even if you're working at a nine to five job.

Chris Wilson

Yeah. And I think that really does come back. It's almost like the idea. I don't know if you ever read it, like Victor Frankel's book, man, search for meaning. And I think a lot of us sometimes like we're trying to uncover our purpose or like search for purpose or search for meaning or like, but what I've really realized, especially when it comes to designing a career, you don't need to escape from and like even just from a mental health standpoint.

It's up to us to decide what has meaning. And I think that's the perfect example for me, like is there's a local coffee shop in, or in Canada called like Tim Hortons that's super popular and like often I'm amazed by the fact that I'll go through the drive-through window and I'll get somebody who's incredibly like happy and excited and like they're

You're almost like, why are you so happy? Like you're not in this like fantastic job. I remember talking to one lady and she's like, oh, she's like, this gives me purpose. Like I get to be the first person to say hello to someone in their day. I get to hand them over like a hot piping coffee that I know is gonna start them off right. And it was like another great example of like, how do you find meaning? It's like, well, you create meaning and kind of like the actions that you take every day. We're like,

there were a number of years where like I was working in a job that I didn't, I didn't enjoy, but I started to kind of look at stuff outside of work as well. Where it was like, okay, like work allowed me to start a newsletter and it allowed me to kind of like write about some of the things that were going on in my life. And then through that, I started to kind of more so uncover of like, what is the kind of life that I want to live? And to me, it was largely like, Oh, I don't, I don't want to trade my life.

a way for something that I don't care about. And I think that's something that's kind of hard to come to terms with sometimes is that there was this book through Bonnie Ware where she talked about, I think it was like 2,500 or 3,000 people in the last stages of their life. I think it was like the last 12 weeks of their life, cancer patients. And what she found is like, there were five regrets of the dying, like all of them.

Chris Wilson

had the same five regrets. And to me, when it came to designing kind of a life you don't need to escape from, like I kind of looked at those regrets and kind of went through them and go, okay, like number one regret was like not living true to yourself and just doing things because you thought that's what others wanted you to do with your life. I'm like, okay, like how do I kind of invert that? Well, it's like, am I doing something that I wanna do or am I doing something because I think like,

Oh, I should, I should go to med school or I should like, this is the career I should do because my dad did this or like starting to kind of look at those things and like, just ask myself questions and start to figure out, oh, it's like, let's get clear about what you really want. Once I was able to get clear about what I really wanted, then I could start to kind of like set some milestones up. So what does it look like to move that much closer towards those things? And it's just, to me, it was like the baby steps.

Like that idea that like life isn't a sprint, it's a marathon. Like there's, there's sustainability to that. And so much of like, I think that's where a lot of people struggle is they want their life to be different tomorrow. And it's very hard to make some of these big changes in a short period of time.

Srini Rao

Yeah, I mean, it's kind of like your most powerful actions today lead to delayed consequences, which I think is fascinating. And I think that one of the things that I keep coming across in the books that I've been reading is this concept of present bias, where we make decisions that are the best for us in the moment without realizing they might be bad for us in the future. And the opposite turns out to be true as well.

Chris Wilson

Yeah, it's an odd thing I think that a lot of us, like humans, get sucked into is that kind of like the immediacy of things. Where they talk about like even just like kids, a great kind of like study was talking about like the idea of like what makes kids stay happier throughout their lives is so much of like delayed gratification. Like can you delay the gratification of the hard work?

And that's a tough one now, again, coming back to like social media or things like that, like you're, you're used to these kind of like just dings that go off, like giving you this kind of like hit of dopamine where it's like a reward. And I don't think a lot of the hard things in life give you those. Like, if everybody's going down that path, it's

It's either an indication that you should follow it. But like in a lot of cases, it's more so like that might not be the path you want to go down. If everybody's going down it like you might want to kind of like forge your own path.

Srini Rao

Mm-hmm, yeah, absolutely. Yeah, I think it's funny, because we had Daniel Leatherton, who wrote the organized mind here, and there's this opening quote I just happened to hear this morning, where he talked about the delayed gratification of Sistine Focus, and he said, do you think Michelangelo could have painted the Sistine Chapel if he was on Twitter all the time?

which absolutely is true. So we're getting close to the end of an hour here. One other thing I wanted to ask you about, now that you have a daughter, I mean, it's probably crazy to be asking you about how you think about the future of educating your child, where you're probably just trying to make sure that she's well-fed and clothed and warm and surviving. But if somebody dropped out of high school, when you think about the future of how you're going to educate your child,

What do you think? I mean, I know it's damn near impossible to predict what the world will look like by the time your kid's in school, but I'm just curious kind of what you thought about it.

Chris Wilson

It is something that I, to be honest, I lose sleep about sometimes because I, in some ways that like, I had such a poor experience with traditional education that I'm like, I want to keep my daughter as far away from that as possible. But again, I don't want to necessarily push my kind of beliefs on her as far as kind of like, she could have a completely different experience than me. But I think what.

really does stick out to me is that realization like Deloitte had a great study where they talked about like it was like 60 or 70 percent of kids in elementary school are going to be working in jobs that don't even exist yet. So when I think of like a traditional school system and just the method in which they learn and I don't even really want to say learn because it's majority but it's just memorization like it's rote stuff.

And I think that's something that I struggle with. And I think a big part of what I want to kind of balance that with is through kind of like the, the mindset of entrepreneurship, because I think entrepreneurship can more or less teach you everything you need to know about life. Like James Clear had a great line where he talked about like personal growth is really like a business pursuit in disguise.

Right? Where it's like, you learn a lot about yourself growing a business because you recognize that like you are often kind of the biggest bottleneck to your business. Uh, from a gross standpoint, from just an understanding standpoint. So like you have to develop yourself, you have to grow. Otherwise you're always going to be limited. And that's something that I think is worth its weight in gold. And that's something that I really kind of want to help teach is just the

Srini Rao

Yeah.

Totally.

Chris Wilson

the understanding of yourself through working on something, something that again has like skin in the game, like it has meaning to it. Like you're building something, you're creating something and you're putting it out into the world. Doesn't necessarily need to make money, but like make it real, like put it out there, share it, talk about it, talk to others. Like there's real value to that. In school, at this point, I don't believe does a good job about that. Like,

I know you had Seth Godin on and one of he's talked about like the idea that like, he recognized the issue with the school system just based on like kids asking, is this going to be on the test? It's like, if you're asking that question, you're not developing like the ability to learn. Like you're literally just kind of like memorizing something so you can put it on a test. But like, I don't know about you, but once I got out into the real world, you recognize that like,

Oh, like school does very little to kind of like prepare you. And it, especially with entrepreneurship, there is no right way of doing things. There's just your way of doing things and kind of like comparing it to how other people are doing things.

Srini Rao

Wow. Well, I have one final question for you, which I know you have heard me ask. And how we finish all of our interviews being a mistake creative. What do you think it is that makes somebody or something unmistakable?

Chris Wilson

It's one that I've bounced around so many different times. And I think what I keep coming back to is it's like that internal compass of like your values, like in that sense of like your North star or like an unmistakable creative to me is somebody who pursues that North star of like what you value. Oh.

Chris Wilson

Sorry about that. Yeah. So to me, like an unmistakable creative is somebody who really truly kind of follows that compass, like their internal values of what they want to create in their lives. And it's not necessarily kind of like, I would say it's not taking the easy path. It's taking the path where like, you're gonna run into challenges, you're gonna run into difficulties, but you recognize that there's meaning to that path. And I think that's a big part of it. It's like,

Srini Rao

No worries, we'll make sure we edit this out.

Chris Wilson

doing what feels right, not necessarily just doing what you think you should be doing.

Srini Rao

Amazing. Well, I have enjoyed talking to you so much. This has been really insightful and eye-opening and thought-provoking and, you know, left me with lots of questions and lots of new ideas to explore, which are my favorite kinds of conversations. So, I can't thank you enough for taking the time to join us and share your story and your wisdom and insights with our listeners. Where can people find out more about you and your work and everything that you're up to?

Chris Wilson

I, as I mentioned, I'm not on social media, but I do run a weekly newsletter that I've been putting out since 2016. And it's something that I really put all my energy and effort into. And you can read that at simplifiery.com slash newsletter. And if I were to leave kind of like one, one thing I would say, thank you for continuing to kind of like show up and put this show out there because I.

Showing up is often the hardest thing to do, right? The easy thing is to give up, not continue, and just do nothing. And for you to show up after all these years and be able to provide us with a place to have these conversations is really meaningful. And I really do appreciate that, and thank you.

Srini Rao

Thank you very much and for everybody listening we will wrap the show with that