Welcome to Actualize, a podcast that explores the intersection of performance, ambition, and mental health. 

In this episode, host and founder of First Session, Rob Pintwala spoke with Jason Silver, entrepreneur, startup coach and author, to discuss the concept of ambition and how to find fulfillment in both work and personal life. 

Through personal experimentation with techniques like intermittent fasting, cold plunges and polyphasic sleep,  Jason has discovered that while there are many resources available to help people accomplish difficult tasks, few focus on finding enjoyment and fulfillment in the process itself. 

"Sometimes when I stop and actually look back at all the things I have going on, geez, this is like a lot of stuff. But figuring out a way to do that in a way where it's like a positive driver in my life and not a drain, which it used to be for me, is the code I've been trying to crack." - Jason Silver

Recognizing this as a significant problem, Jason aims to provide practical tools and frameworks in his upcoming book Quietly Crushing It, to help others  find more enjoyment and fulfillment in their own lives.

Sign up to Jason Silver’s Weekly Newsletter here to receive tactics from the book and others, distilled down to ~2min reads to help people do or feel better at work. 

Get early access to Jason’s book Quietly Crushing It 


[00:02:20] Working hard versus working smart.

[00:06:06] Creating companies people love.

[00:08:44] Ambition and intention.

[00:12:43] Unpacking Ambition and Self-Reflection.

[00:14:11] Ambition and working fewer hours.

[00:17:21] Unpacking failure.

[00:24:37] Work burnout and disengagement.

[00:27:22] Finding enjoyment in work.

[00:31:23] Putting people first.

[00:37:12] Different paths to the same outcome.

[00:42:34] Therapy and personal growth.

[00:45:45] Aligning work with personal values.

[00:49:00] Small tweaks for greater agency.

[00:52:22] Breaking through barriers to success.

[00:55:29] What would need to be true?

First Session

Find the right therapist for you.

First Session exists to help you find the right therapist for you so you can get help now. We deeply believe that the fit between you and your therapist is the most important factor for a positive outcome. First Session is committed to making your search for a therapist user friendly, transparent, and trustworthy.


Episode 16 - Jason Silver

[00:00:00] Rob Pintwala: Today's episode is with Jason Silver. Jason is a father of two boys and he has founded multiple companies. He was fortunate to play a role helping to scale Airbnb in its earlier days. He currently spends his time coaching and advising other founders and their teams on how to build great, lasting businesses that people love working for. Jason lost his sister in 2019 and that forced him to change his relationship with work. He went deep on productivity, mindfulness, neuroscience, and behavioral psychology. Through a lot of personal experimentation, he found a way to get balance back into his life without sacrificing his impact at work. Jason's mission is to help people find ways to enjoy doing hard things in their own lives. And his hope is that by distilling down years of trial and error into specific actionable lessons, people will be able to get more back into their own life while still having a big impact at work as well. In this episode, we talk about ambition and what that actually means.

[00:02:13] Rob Pintwala: We talk about working hard versus working smart, and even what that means in the context of raising children. We discussed the book, which Jason is writing, which is called Quietly Crushing It while Diving into Practical Tools and Frameworks, including examples that can help folks struggling with burnout or finding meaning in their careers to unlock more enjoyment and fulfillment without changing jobs. I hope you enjoyed my conversation today with Jason Silver.

[00:02:42] Rob Pintwala: Hey Jason, thank you so much for joining me today on Actualize.

[00:02:45] Jason Silver: Thanks, Rob. Great to be here. Thanks for having me.

[00:02:48] Rob Pintwala: My Pleasure. Wanted to start off with a little bit about your career up until this point and your journey in the workplace and sort of how you got to this point. And maybe we'll start with a quick view on what you're working on right now and how you got to this point. Yeah.

[00:03:08] Jason Silver: Happy to. So if we zip all the way back engineer by training, did undergrad, graduate degrees in engineering, thought like, I'm gonna be pretty technically learned pretty quickly once I got into engineering that I was really attracted to the problem solving aspects, but a little bit less to the deep technical stuff. Like some people just love going deep on tech and all the power to them. It, you know, it wasn't me but I was very interested in how you build a company around an idea or a piece of technology or something like that. And I did the first entrepreneurial thing that I could think of at the time. I didn't want to go and get an MBA, I found a startup, told him I wanted to work in business development, told him I had nothing on paper that says I could do that. Managed to convince him to let me come in and work for free for a bit if it didn't work out. No harm, no foul. If it did, you know, we'll see where it goes.

[00:03:56] Jason Silver: It wound up going great. I was very lucky. You know, I got kind of an on the [00:04:00] job M B A. And I had a software company on the side. It wasn't really a company, actually, it was like a hobby. And I decided, hey, like blissful ignorance, let's go start a company. So I started my first company and had a great time.

[00:04:12] Jason Silver: Hit a single or a double, you know, it was no Google, though few companies are, and I wanted to go bigger and my partner wanted to, my business partner at the time wanted to have it as more of a lifestyle business. And so we split very amicably. Founded it by my first venture backed company a couple years ago.

[00:04:29] Jason Silver: Built that up and crashed it. So I got to experience what unmitigated startup failure feels like, which might be either a chat for an hour, chat for another time.

[00:04:39] Jason Silver: And when my confidence was at, was at an all time low. I got really lucky again after crashing the company. A couple weeks or a few months or something went by and one of my investors whose money I almost entirely lost, he called me up one day, aj, there's this team.

[00:04:52] Jason Silver: You might want to meet with them. I think you like what they're up to. It turns out it's the folks from Airbnb. And I joined there in the early days of that company. So I got to experience [00:05:00] what, you know, a few hundred people to many thousands feels like, had my first kid on the way. I was on an airplane.

[00:05:07] Jason Silver: Folks all over the place on my team did the only thing that felt normal to me. I was like, great, I need to be in the city. I'm gonna be in. Jumped to a very early stage startup. I'm talking like a slide deck, half a financial model, no product. So I joined Integrate AI. Built that up over a little while and then decided I really wanted to focus on helping other people build their companies, which is what I do now. I'm an advisor for executives, founders, and leadership teams, helping them really think about how to build companies that people genuinely love working for. I'm writing a book right now, which is keeping me very busy. challenging. Love it though. It's called Quietly Crushing It. It's all about how to unlock a bigger impact at work with less burnout in your life. I've written the manuscript, which is fun. I'm working with one of the editors from Atomic Habits on getting the book done, which is really great. Just launched uh, newsletter around the content, which is fun too. [00:06:00] And there's the grab bag of stuff.

[00:06:02] Rob Pintwala: Yeah. Yeah. I love that. Thank you for the context. So just to reiterate, right now, your focus is working with companies and helping them to create companies that people love working for. And at the same time, you've already done a first draft of this book. It's not released yet, but it's all about not having people burnout in their careers, which is definitely gonna be a big topic of our chat right now.

[00:06:28] Because, you know, during Covid I think burnout became more prevalent and now it doesn't seem to have gone away. And not that Covid has gone, but we're a few years into it. And before we chat about the burnout stuff and you know, what you've researched and what you're writing about, I wanted to ask a little bit of a deeper question about your own

[00:06:52] Pivot if in your career and your essentially your own ambition, like you strike me as someone that's super [00:07:00] ambitious, or at least was for a period of time. And that I've been thinking a lot about is ambition and like what it means to different people. And I'd love to get your take on ambition for yourself and what you've learned about ambition for other people as well.

[00:07:17] Jason Silver: Oh, deep questions for sure. Hard to comment for other people, but kind of watching other people go through their journeys and helping them is insightful for sure. It's funny the way you worded it, like, I've actually had people ask me questions point blank, like, what happened? Man, you used to be so ambitious. And what's interesting is I don't feel that my ambition has changed at all. The way that I interact with my ambition is very different. I don't think in my life I have ever been more impactful with a unit of time than I am right now. Out. So my ambition is sky high. Like I, I'm doing a lot right now.

[00:07:49] Jason Silver: It's, it's like sometimes when I stop and actually look back at like all the things I have going on, I'm like, geez, this is like a lot of stuff. But figuring out a way to do that in a way where it's like a positive [00:08:00] driver in my life and not a drain, which it used to be for me is the thing that it's the code I've been trying to crack and what I'm trying to write about and what I'm working with folks what I'm working with folks on.

[00:08:09] Jason Silver: And so it's less about reducing ambition and more about relearning how to operate with ambition. Because for ambitious folks, at least for myself, if you told me to just care about doing less, it, like never, it never computed for me. It was never like, oh great, I'm just gonna take what I want to accomplish and I'll chop off the top 40% and that's gonna feel good for me.

[00:08:32] Jason Silver: Like the drive is always there trying to find ways to still think about everything I want to do, but changing the way I'm trying to approach it is really what has been. my journey over the last couple years. And I think what I would say I really learned is I have this idea that like, you know, I always had this ambition. I had to learn my intention. And I think when you have ambition without intention, it winds up creating a lot of tension. The tension [00:09:00] between what you accomplish, what you thought you wanted to accomplish, and what it feels like when you actually make it happen. And when you're doing it on purpose, you kind of learn, you iterate, easy go.

[00:09:10] Jason Silver: Maybe you make mistakes, but you're kind of working with clarity towards, I'm doing this and this is why and this is how it fits into my life. When you don't have the intention and you just have unbridled ambition, I think that's when you can wind up in a situation where you might regret it.

[00:09:25] Jason Silver: Even if you accomplish the things you wanna accomplish, you might regret how you got there, what it took, et cetera. If you didn't have the intention upfront. And that was kind of big. learning for me is the ambition's always been easy and clear the intention behind it. Why do I want these things?

[00:09:40] Jason Silver: Why do they mean these things to me? That was always the hard thing to unpack, and I put a lot more attention towards the intention than I ever really used to.

[00:09:50] Rob Pintwala: Yeah, that's. Super interesting. I think about the intention quite a bit, and I've had a couple other really interesting conversations [00:10:00] about the intention. You mentioned that sometimes the intention isn't clear. I'm curious if it's not this is a mental health podcast um, and, and therapy, but I'm curious if you think about the intention being sort of always there, but maybe not conscious.

[00:10:17] Like, is the, is it a subconscious, like if you are ambitious, but you don't know why, do you think there is a reason but you just don't know it yet? Like maybe it stems from how you're brought up or watching your, you know, parents succeed or like what you heard going to school and all those things. Like, are people just ambitious outta the womb or

[00:10:39] Jason Silver: Yeah.

[00:10:39] Rob Pintwala: do they learn it even if it's not in their awareness?

[00:10:42] Jason Silver: Yeah. It's funny, you know, we were talking about like nature versus nurture, you know, earlier and like hard to know. You know, a big thing for me was I went through like a crazy period of experimentation. I still have it, but I was ramped up before where like I would be running every two weeks. I had probably two or three [00:11:00] tests going to experiments on myself going against my own kind of positive psychology.

[00:11:04] Jason Silver: And I was really trying to unpack this for myself. And part of that for me was just like reading everything I get my hands on. I read a lot of stuff on things like evolution. How does the brain work? How did we get here? not being a scientist myself, it's hard to know. The thing I learned about myself is it's in there and I could try to fight it or channel it in the right way.

[00:11:26] Jason Silver: It's hard for me to think about how I just let go of the ambition in my life? It's hard. For me personally, and as I really tried to unpack it, I started to think about, okay, I'm trying to accomplish this thing. And to your point, I might not know why, but then that gets added to my list of ambitions. I wanna write a book. It feels important to me. I can't put my finger on why it is, but I'm writing and I'm writing and I'm writing, and I'm putting the time and energy into it, and I'm still not quite sure why I'm trying to accomplish this thing. [00:12:00] Therefore, I'm gonna intentionally try to figure it out as I go. What is it that I like about this thing? One of them is that it's given me an opportunity to talk to folks like you on a podcast, which I really love. I love meeting new people, and it's a great way to meet new people. Hey, I'm writing this book. Is it about these things? Is that interesting to you? Wow, that's cool.

[00:12:16] Jason Silver: Let's talk like it's become a great avenue for that. Could I have predicted this, you know, in advance of, of writing the, the book? Frankly? No. I don't think so. So it's more about just, I'm quite put a lot of, like I said, attention on intention in that I either know it or I know that I need to figure it out and it becomes part of like how I'm operating

[00:12:39] Rob Pintwala: I've heard a lot of people that are high performers are a little bit wary of a lot of self-reflection and like, Deep work. Like if they're super ambitious and they're almost afraid that looking at that too much for [00:13:00] like why they're ambitious will stop their ambition.

[00:13:02] Jason Silver: Yeah. 

[00:13:03] Rob Pintwala: Is that something that you ever came across or witnessed in your high performing environments?

[00:13:08] Jason Silver: I was super scared of what I'm doing now. I was like, what's gonna happen to my ambition? I'm used to being in startups. I'm used to being like, I'm used to being the person that's like raising money and hiring people and building teams. And like, you know, for a while there, my job was a big part of my identity. You know, it was less what I do and it was more this is who I am and like what happens when that all goes away? And I think what's interesting is I was worried my ambition would go down. As I started to think more about changing the way I was interacting with work. It's gone up. And what's shocking for me when I take time to reflect on it, is I've never worked fewer hours or been more impactful ever in my life. And it's not that I don't work, I work hard, but I work less empirically, I work less now in terms of brute number [00:14:00] of hours than I did. In any period of my career previously. And yet I believe I'm being more impactful now than I was before. Like why is that happening? And I just think hours is a terrible heuristic for ambition, accomplishment, all these kinds of things.

[00:14:15] Jason Silver: Like it, if there's an outcome that you're trying to accomplish, it's really hard to figure out what the thing is that's gonna make it happen. And so I think often we swap the hard thing for the easy thing and we're just like, well just measure the hour. Like you're obviously working hard and you're doing great things 'cause you're working 80 hours a week, but what if I can get the amount of work that you got done?

[00:14:34] Jason Silver: Like if I can get to the outcome that took you 80 hours in one hour, like that to me is just, that's just smart I should just do that. And so a lot more time thinking about like, well, what am I trying to get to and what is the right way to make this happen in a way that fits with my life and what's going on?

[00:14:51] Jason Silver: And yeah, it's an interesting learning for me that I just, I had to try to tackle ambition in a new direction, and the results were [00:15:00] surprising. More

[00:15:01] Jason Silver: ambition, more impact, less time, effort, and energy.

[00:15:06] Rob Pintwala: Yeah, I selfishly want to, I'm gonna ask you another question about that. 

[00:15:12] Jason Silver: It's not selfish, that's why we're here. I guess

[00:15:14] Rob Pintwala: yeah. You have two, two children. Three and six. You told me before we started recording Two boys. You know, I think for myself a lot of my value of hard work, which I still value, but I think I do have a different perspective on it now.

[00:15:30] Like I work in tech and none of my other family worked in tech. For example, my grandfather, who was an immigrant, came in. My dad worked nonstop. And how do you raise your children? I hear that like the popular discourses that praise the work, praise the hard work, don't praise their intelligence, or don't praise their, you know, cleverness or how do you think, what do you think about that?

[00:15:57] Like how are you looking at that from a parenting lens?

[00:16:02] Jason Silver: That is a great question. And one that is close to home. I think it's really challenging and I want to be very mindful of not sharing parenting advice because it is a highly personal thing and like what works for some parents doesn't for others. And it's so easy to feel so much judgment as a parent that like, I wouldn't want anyone listening to this to feel that, Hey, you don't do it the way this random person says they do it, therefore it's not right. I think the things that I've kind of seen is, at least with my kids and their personalities, they are looking at accomplishment. Whether I am instilling in them or not, or making a very active effort not to which I am really trying hard to do. It's everywhere. It's impossible to avoid, at least for me, with the circles that we run in and where we are.

[00:16:50] Jason Silver: You put your kids in sports, we celebrate when such and such kids win. You put them in class. Did they get the homework done? What did they get in the, what did they get in the project? What mark did they get? [00:17:00] Constantly comparing myself against the other kids personally for my kids, I just think it's in them and I don't know that I can take it out of them. I really do try hard to praise them as much as I can for the activity, not just the outcome. Like you said, really great to see you working really hard at this. That's really amazing. That certainly helps. One of the things I wish I had earlier, and this is talked about a lot, but it's very hard to genuinely implement in my experience, is like this idea of unpacking failure. And that's a thing I spend time on with my six year old. He's six. He's not that, you know, he is not that old yet, but what can we learn from this? What are we gonna do about this next time? And not just like, ah, God, we didn't X, Y, Z, or you couldn't A, B, C. It was like, okay, cool. Like, this didn't work out, no biggie.

[00:17:53] Jason Silver: There's gonna be another one. Like, what are we taking away from this so that we don't, you know, we don't hit the same roadblock again [00:18:00] in the future. And it's just been cool to see as they're growing up, like he's started to talk about it a lot more. He talks about, Hey, I worked really hard at this thing, not just, I accomplished this thing, which is fun.

[00:18:13] Jason Silver: And he likes to tell me the stuff that like, you know, it's, he'll laugh at this when he hopefully sees this in many years. But, you know, my son will walk up to me, tell me a thing that he learned and he goes, big brain. And like him, that's his kind of expression from when he learns things. He has a big brain.

[00:18:27] Jason Silver: I'm locking it in like, here we go. So, It's super tough. You know, I try to do as much as I can and I think just being mindful of it is helpful 'cause it for me as well, it's so easy to slip into like, oh, you did that great job, you did this great job.

[00:18:40] Rob Pintwala: Yeah. Yeah. So it almost sounds like sort of praising the work ethic. It's almost like it's easier to unlearn later in life than to kind of get off the hamster wheel of work and work and work and work. Not to say [00:19:00] that you're instilling like work all the time nonstop, kind of like Tiger Woods values but yeah, it's almost like better to have that than to sort of start trying to cut corners from an early age, I guess. 

[00:19:13] Jason Silver: My wife and I both really try to focus with them on things like, what do you enjoy? And I feel like if, as long as that's kind of top of mind. Even if it starts turning into like working very hard and it becomes very outcome oriented, just never losing sight of life, if you enjoy this thing, you will do better at it. If you don't enjoy it, we should talk about why we're doing it. Right. And I think that idea of just keeping that, you know, front and center of when there's a tough moment, are you enjoying this? Like, is this a thing that you like doing? And then when they find stuff that they really love doing, just kind of jumping in all the way and that, that is one where I really feel like, I mean, it's funny, I never thought about this way until you asked, but I'm like writing a book.

[00:19:54] Jason Silver: I've written a book about it. Like enjoying something that you're doing, it makes such a big impact. And really just[00:20:00] 

[00:20:00] Jason Silver: bringing that to the surface of the accomplishments. Great. Did you enjoy it? Do you enjoy these things in general? Do you want to keep doing it? Like that idea and that mentality? I didn't really think about that.

[00:20:13] Jason Silver: You know, when I was younger I was so focused

[00:20:14] Jason Silver: Like, am I accomplishing the things I need to accomplish? Is the trajectory. On the course that I needed to be on. I wasn't really asking, you know, do I enjoy what I'm doing? And if somebody asked me that question, it, like, probably I would answer it in a very surface level way that was never really deeply thought out about like, yeah, I really genuinely enjoy the things that I'm doing day in and day out, even though sometimes of course it's like, there are tough days and hard moments. But, you know, I don't know that I spent as much time thinking about enjoying the experience and what to do to cultivate the experience as I do now.

[00:20:53] Rob Pintwala: Yeah. Well, you know, I can relate to that and you may not have the, you may not have thought, you had almost the permission to [00:21:00] think that way. Right. Which I think a lot of, like, I imagine this is going to transition really well into, you know, talking about burnout and stuff because like why did burnout maybe not exist in our parents' generation?

[00:21:13] Because they weren't worried about finding enjoyment in their day to day. Right. Maybe they didn't expect that was a possibility for them. Or, you know, definitely generations back. It just seems like we're at this kind of stage of like, you having our needs met. Well, those of us who are, you know, you know, lucky enough to be in that place.

[00:21:33] But speaking of enjoyment though, I wanted to reference something that I've, I heard you say in the past that you lost the joy of doing hard things and that maybe was a part of some of your transition into. Different work. Is that correct? Or maybe you can kind of unpack that. And what do you mean by that?

[00:21:53] You lost the joy of doing hard things.

[00:21:55] Jason Silver: So I kind of have this mission now that has become super clear to me. And the mission [00:22:00] that I have is I really want to help people enjoy doing the hard things in their lives. And the reason why is I always really enjoyed hard things. Again, maybe not at the moment, but you have a hard challenge.

[00:22:12] Jason Silver: It teaches you some great stuff. The feeling of accomplishment is great, like really liking hard things. What I realized on reflection was that I had kind of lost the joy of doing the hard things. I was just grinding them out and doing them because they were hard. And I think if you're not enjoying the process, eventually the accomplishment or lack thereof gets old.

[00:22:34] Jason Silver: Like, it just doesn't, it just burns you out. Like we were talking about basically. But if accomplishing that thing gives you energy throughout and it's something that is like driving you and wellbeing in your life as you're working your way through, it's super important. And as I reflected back, I realized, huh. Like, I'm still doing all these hard things and I'm putting a lot of energy into helping people accomplish the hard things. Here's a thing, I've learned a tactic you can use. It'll help you in your job. [00:23:00] I wasn't doing a lot to help myself enjoy what I was doing and help other people enjoy what they were doing either.

[00:23:05] Jason Silver: And so it, it just left. And I realized that the absence of this word was the real thing that was getting me down. It's like the mission's not to do hard things. It's to enjoy doing hard things. And as I mentioned I did a lot of experimentation for myself to understand how am I gonna enjoy better, you know, at life, at work I was doing, I mean, intermittent fasting, cold plunges, I was like hanging for three minutes every day by my arms, like going for runs, walking, like silence, too much talking polyphasic, sleep, like all sorts of stuff. I. What I learned as I went through that is like I was not the only one feeling this stuff. Like I looked around me, a lot of people were, you know, there were a lot of resources to help them accomplish hard things. Not a lot out there to help you enjoy the accomplishment of the hard things, the doing of the hard things.

[00:23:54] Jason Silver: And I just kind of dove into that and said like, Hey, this is a problem. I think it's huge. The [00:24:00] more I've researched it, the more I look around what's happening in work right now, which is quite unprecedented. It's not. It is a very big problem. And you know, I want to do my part to make a difference.

[00:24:09] Jason Silver: 'cause I think it's important.

[00:24:11] Rob Pintwala: Yeah, maybe we can talk about that right now. Just what you have learned in your research and your own experience. Like when I look at doing hard things, the enjoyment, . Likely comes from that accomplishment. Right. And some maybe that dopamine trigger or something at the end of it. Right. Or maybe along the way hitting milestones.

[00:24:30] Right. And maybe you can align that with something you actually enjoy or maybe you can't. Right. But what have you learned about that? 

[00:24:37] Jason Silver: Yeah, for me, like, you know, you asked about some of the research and the numbers, like it's like 80% of people have burned out at least once in their job. 77% of people are disengaged, you know, at their jobs Today. Productivity is at like an all time low. It's just work that isn't working. Like that's what it feels like to me as I talk to people and you [00:25:00] do the research is what it looks like to me. And what I feel is really missing is a lot of conventional wisdom, sorry, things that you think would make sense. There's actually been really great experiments run unintentionally that have given us some really interesting information. So when I say experiments, I don't mean a bunch of psychologists pulling people into a lab and observing them or making them fill out a survey. It's just coming out of the pandemic. It was set up this way. Again, not on purpose, just with the benefit of looking back and the two that come most to mind is, if you're not feeling great in what you're doing, conventional wisdom says, go get another job. A lot of people did that. It's called the Great Resignation.

[00:25:38] Jason Silver: Millions of people went and got new jobs, and if you ask them now, 80% of those people will tell you that they're regretting their decision to make this change. So just getting another job is not gonna solve the problem for you. The second big one is quiet, quitting. It's all over the place. We talk about it everywhere.

[00:25:52] Jason Silver: That's where you do the minimum possible not to get fired. You're pulling back at work to get more time for things in the rest of your life, and [00:26:00] this is the conventional wisdom of work-life balance, right? If you spend less time working and more time on life, things will feel better. The challenge with this one is it doesn't seem to be bearing out on what's happening for folks. Something like 80% of folks around the world are quiet, quitting in some way, shape, or form. Yet 65% of people will say that they're struggling in their lives. So you're getting more time and effort, more time for the rest of your life. But that's not leading to the ultimate goal, which is like overall wellbeing. And when I look at that, the thing that I kind of take away is the things we're trying aren't working. We need to try something new and it's really unsexy. But the answer that I think is there is, it's not about what job you do or how long you spend doing it. It's actually about the day-to-day. It's like day-to-day at the moment.

[00:26:51] Jason Silver: Stuff that really has such a humongous impact on how you're feeling. And we spend so much time doing quarterly reviews or performance [00:27:00] reviews, or looking back on the last six months or three months, how much time you spend, thinking about what you did yesterday and how much of those things you actually enjoy.

[00:27:07] Jason Silver: Like break it down to the activity level. Look at what's coming up tomorrow, what things do you have to do tomorrow? Are you doing them in ways that you actually enjoy? And it feels a little bit unsexy. You know, getting a new job is a big moment. But taking a task that you have to do that you usually hate, and finding a way to do it in a way that you enjoy a little bit more, and then a little bit more next week and a little bit more the week after that's the thing that's gonna lead to like really lasting positive change for you. Because if you just jump and get a new job, eventually the way that you work, the honeymoon period will be over. You're gonna settle into old patterns and the result is gonna be all the old feelings. Again we have to look to change the way that we're interacting with work. 'cause what's pretty clear is companies need people to be more productive and people are not prepared to give up their lives anymore to accomplish that productivity. So the [00:28:00] need is there. We just need to find another way of filling it that works for the way that people wanna work today.

[00:28:04] Rob Pintwala: Yeah. It sounds like in order to change, In your experience, like can it happen kind of from the ground up, from the employee level? You know, how do you kind of convince your manager or do you even need to, I know we, we could easily get pretty deep into the weeds here, but like, does it require a full culture shift at a organization in order to work in a way that people can enjoy the, what might've been known as the shitty tasks of their job or whatever?

[00:28:35] Jason Silver: I mean, it's not even just shitty tasks, right? Like, it can be tasks that you like, and the question is, how do I like these even more? Or how do I do more of the tasks that I like and less of the ones that I don't like ? It is called Work for a reason. You know, we're not going to a country club.

[00:28:49] Jason Silver: It's not play, you know, it's not to say that every moment of every day is really gonna be amazing. For me, it's about like, how do we just move the needle so that a greater percentage of the stuff is enjoyable for you? Or leveraging [00:29:00] skills that you really enjoy putting to work versus the opposite. Do you need to work at a place where the culture completely shifts?

[00:29:08] Jason Silver: It would be hard for me to make a declarative statement. My hypothesis is no. And the reason why is: You know, even if you work for a very micromanaging manager, the words you choose, the meetings you go to, the work that you put together and what's in it, and the quality of it, and what research you do to put it in place. These things are genuinely, generally up to us. And my theory is that if you can find a way to work better, the impact will be there. Your boss will notice it. And if they're a hard person to convince that, Hey, I wanna start doing some things in a different way, start by showing them, show them the momentum, show them the benefits, let them see that, hey, this is really gonna be beneficial, not just for, you know, Rob, but it's gonna be beneficial for the company as well. Great. Now we can build on it rather than starting from ground zero. And the first couple [00:30:00] steps in my experience are not. They're not crazy. They're not like, you know, holy. We gotta completely change the way that the team is interacting. We have to change the way the team is operating. It's much more granular day-to-day stuff where you change the way you communicate a little bit, change the way you make decisions a little bit.

[00:30:18] Jason Silver: Change the way you decide you actually do the task you have to do. Change how you're thinking about growing as a leader or the way that you look for opportunities inside of the company. These are all things that, you know, I've kind of seen consistently across folks that are owned by the individual, not by the person that's managing them.

[00:30:37] Rob Pintwala: When you were managing lots of people at your prior jobs like I imagine that Airbnb, you managed lots and lots of people and probably other companies too. Were you thinking at all in this way or were you just kind of doing like the K P I thing, like whatever Google says to do.

[00:30:57] Jason Silver: Yeah, I. I [00:31:00] think Airbnb is a place where I really learned how to think about this differently. You know, coming into Airbnb, I was like an engineer's manager, meaning like, tell me the numbers. Tell me what we need to accomplish. People are a necessary condition to accomplish the tasks, but like, if it's not Rob, we could swap 'em out with somebody who does the same kinds of things that that Rob can do. I think I had it completely backwards and I got to Airbnb and one of the big lessons I had there is to put the people first. Who are the people, what are they trying to accomplish? What matters to them? What gets them excited and how do we make sure that they're doing and feeling great so that they can take care of all the problems that we're trying to solve? Metrics, goals, these things, they're all very important. But they're directional. It's like to help us understand what direction we need to move in. I think over time I learned to put a lot more of my attention on, okay, what's going on in Rob's life? What kinds of things does he like to do? How do I think about prioritizing and passing work to [00:32:00] Rob that he is both going to excel at and really enjoy? And the more time I spent on that, the better the results started to become. And again, it's not all the time. Sometimes you gotta eat, you know, dirt a little bit. Like we have to get this thing accomplished. It requires some pretty crazy hours and a bunch of tasks that are not gonna be a lot of fun. But that's a moment in time, right?

[00:32:23] Jason Silver: We all kind of sign up and we say, all right, let's get in a room, or let's buckle down for a week or two. Let's push this thing out. It's an exception to the rule. It shouldn't feel like this all the time. Otherwise, like that's the thing that leads to burnout. You know it, if you think about running a race, you can only sprint for so long. You're going to run out of energy. That's kind of the way that it works. And so it's not that, I would say it was never hard or it always felt great. It's just what I spend now. A lot more time thinking about how I want this to feel, both for myself and other people. And I think one of the biggest challenges that we have in the workplace [00:33:00] is it's very conducive to what you do in a job or a project or a team. It's very natural to think about what we are trying to accomplish. What's the goal? What's the project plan to get us there? What are the steps we're gonna take? Like this describes the work. We spend very little time on the experience. And so one of the things I like to do for myself, I advise other people to do, is of course, do all that first grouping of stuff.

[00:33:25] Jason Silver: It's important and necessary, but equally necessary is to take a little bit of time, some percentage of the what stuff and devote it to how. How do we want this experience to feel while we're trying to accomplish this goal? How do we want it to feel? It's gonna feel like a real deep burn. Like we just have to pull crazy hours.

[00:33:45] Jason Silver: Okay? At least we've been upfront and we're clear about it, and we know that there's a moment when it's gonna stop. What do we want to call, like what tasks do we need to do? How is that gonna feel as we think about it? And a little bit of intentionality upfront goes like a really long [00:34:00] way. And the whole kind of thesis here is I just personally think it's a bit of a fairytale that you're gonna just land a dream job for me. A job that you love isn't something that you get, it's something that you practice, right? And, you know, the idea of just landing a dream job for me always felt like, yeah, I can happen.

[00:34:20] Jason Silver: It does happen to people, but it's kind of like winning a lottery. And the thing about the lottery is like, you can't engineer the lottery. That's illegal. You'll go to jail. You definitely can engineer your job and you can change the way you're thinking about working so that it has more of the bits and pieces that you really like. And the more I think about work as something to practice, like, I enjoy these things. I'm gonna practice these things every day in the tasks that I need to do. the more that it leads to like, okay, this is, you know, this is way more enjoyable for me. I could give you an example. Maybe that would be easier. I realize

[00:34:51] Rob Pintwala: Yeah. No, I was like waving my hands and like yeah, I was just actually thinking that could be helpful. You know, I think, I would imagine the majority of people [00:35:00] listening, you know, probably could be unhappy with their jobs and trying to think of a way to improve that. But maybe we can put an example in like, I don't know, what kind of a role would you choose?

[00:35:11] Like, either kind of a marketing or a sales role or, you know, something like that. How would you,

[00:35:17] Jason Silver: yeah I'll give people exercise. They can try. It'd be fun to see if anybody actually does this, just to highlight the challenge and then the output of this challenge. You can like to deploy if you can deploy into a thing. And so the idea here is you need a timer, a piece of paper, and a pen. You can use your phone for all of this. I like to have different things for all the things, but whatever works, you're gonna start the timer for two minutes. In those two minutes you're gonna write down 10 things Your smartphone is really great at. Browse the internet, let me talk to people, listen to music on it, blah, blah, blah, blah, blah.

[00:35:49] Jason Silver: Write down a list of 10 things your smartphone's really great at. When you're done, look at the time, restart the timer, write down 10 things that you are really great at. [00:36:00] The vast majority of people will be able to blast through the 10 things. My smartphone is really great at lists and will struggle to even get to 10 in two minutes of things that they're really great at. So we know more about how we enjoy using our smartphones than we do about how we enjoy using ourselves. And it's just 'cause we haven't taken the time to like to unpack it. And so you mentioned really high achieving, ambitious folks. Maybe I don't want to take the time to look in the mirror. This is like a bite-size exercise you can do. And when you've done this bite-size exercise, you know, you can think about like, well, what things do we enjoy? We genuinely tend to enjoy things that we're already pretty great at. And so you might write it down, I really enjoy public speaking. Great. So a thing you can do then is you can look at the tasks that you need to get done and you can think about, how can I do just a little bit more public speaking tomorrow? And so, [00:37:00] a classic example of this would be, you know, let's say that your boss says, Hey, we gotta produce this report on X, Y, Z. At the end of the week, we might have a person who really likes deep analysis. They're human spreadsheets. Right. They like to open up the spreadsheet, write down all the data. I don't really love talking in front of people. The best way for them to accomplish this task would probably be to do the research, build a spreadsheet, and send it around to the entire team by email on Friday. Great. On the flip side, if you get somebody who really enjoys public speaking, probably their best way of doing the task is getting together whatever they need to get together, build the presentation and stand up in a meeting in front of the entire team and present the results that they got.

[00:37:43] Jason Silver: 'cause they get a lot of energy there. Exact same outcome. We got the information out to the team, but two very different people took two very different paths to get to that exact same outcome. The thing you can do is, if you've done the upfront work to think I'm a spreadsheet person versus I'm [00:38:00] a you know, I'm a PowerPoint person, or whatever your presentation tool of choice is. If you've done that upfront work, you can take a moment to be intentional to say, I've been handed this task. How can I deploy something I'm already great at or I really enjoy doing a skill that I'm great at, or a skill I enjoy doing to accomplish this thing that I've been asked to do. In the absence of that list, we just get it done in whatever way we can. You know, either because we're told to do it this way or we don't have time or whatever it might look like. And so just a little bit of time upfront can help. And this, you know, fun little smartphone exercise is a great way to just see the list for you, okay, you might not get to 10 and you'll probably laugh when you see that.

[00:38:40] Jason Silver: Like you could probably list out 30 things your smartphone is great at and maybe not even like three or four that you're great at, depending on who you're, and that's okay. But you'll at least get one or two or three things. And a concrete actionable thing you can do is take that thing and look at a task that you have tomorrow and find some way to [00:39:00] incorporate some amount of that thing in the accomplishment of that task tomorrow, and you'll feel just a little bit better about your day. Do that every day for the next five days. And I'd feel good making you a bet for a cup of coffee that you will have a better week than the previous week.

[00:39:17] Track 1: Yeah. It just sounds so freeing the way that you put it, like that it sounds like there's so much flexibility in what might have appeared to just be like, connect A to B this way. Right. And I, the word I thought about when you were explaining that is like, leverage, you know, all these people are like, create leverage and, you know, maximize your own leverage.

[00:39:38] Track 1: And it's like, well that sounds really businessy and whatever. And the way that you're saying it is like actually connects with a regular human who has emotions and, you know, procrastinates on things. Like, I procrastinate all day on the things I don't wanna do. And. You know, maybe if I look at it a different way, maybe I'll present to myself

[00:39:57] Jason Silver: Yeah.

[00:39:58] Rob Pintwala: I'm curious, like, [00:40:00] I wanted to maybe explore a little bit more around what you said about people really not being able to answer much about what they're good at. And maybe take the conversation a little bit more towards that. Like, and maybe it's now the time that I can ask you about therapy and I've heard you talk about therapy a little bit about, you know, maybe your views of therapy, like shift shifted.

[00:40:26] And I think I heard you say almost like a preventative. You know, even though I run a mental health company, I have lots of people around me who I don't think believe in therapy or try it or see therapists as being people that struggle themselves. So why should they work with them or all sorts of things?

[00:40:44] Packed up in that stigma. So how have your views changed and how did you engage with therapy to help you write down the top 10 things you are good at? Or what

[00:40:55] Jason Silver: so, you know, how do I feel about therapy now? I lack [00:41:00] the right word to express the gratitude and positivity I feel about it as a practice in general. It has made an incredible impact on my life that is 180 degrees from where I was probably five years ago, where I probably would've held many of the stigmas that you mentioned. And I think a big thing that changed for me is just like, I went through a deep period of really challenging assumptions that I had. And if you are serious about finding a way to like, do or feel better as I was at least experimenting with therapy to see feels like the right thing to do versus just making an assumption, you know, the assumption I had personally was like, okay, that's for weak people. I. Ignorant. Sorry, they're not ignorant. I was ignorant. That's a very ignorant mentality because there's nothing wrong, you know, weak people don't go to a physician. And I think, you know, the argument around like, of course a therapist is gonna have challenges in their life. They're human. You know, like, [00:42:00] I don't know if we have sports folks who listen, but pick the world's greatest insert sports coach here. The probability that they're also the greatest individual contributor as a player at that sport is incredibly low. You know, there's a huge difference between the discipline of, you know, playing basketball and coaching basketball. An incredible coach doesn't necessarily need to be an incredible player, which makes me feel like a therapist could absolutely have things going on in their life that's challenging for them.

[00:42:28] Jason Silver: Doesn't mean they can't help me with what's going on in mind because they have a set of tools that I don't. And for me, candidly, you know, it, what kind of brought a lot of this stuff about is I unfortunately lost my sister four years ago, and I was pushed into a position where I didn't have the luxury of, well, maybe I'll try this or maybe I'll try that.

[00:42:47] Jason Silver: Like, I somehow had the wherewithal to recognize that I was going hard down like down into the right. And I am lucky that for whatever [00:43:00] reason, support group of people around me, the mindset that I happened to have at the time I was, I became very open-minded to anything that would help me. Like it was just coping mechanisms. And what therapy did for me was just open my eyes to, okay, this is like an incredibly valuable tool to help me unpack how I'm dealing with things in my life. And so, no, you know, for me personally, it wasn't as if I worked with a therapist to help me. Like, these are the things that I'm great at. I certainly did work with a therapist to help me think about my intentions and like, why do I have these ambitions and What feelings do I have and where are they coming from and what can I do about them? Do I need to do anything about them? How do I sit with them rather than trying to run away from them all the time? That kind of stuff opened my eyes and it's just like, you know, I look back on it now and I think what would've happened if I had started therapy a decade before that?

[00:43:51] Jason Silver: Like, how much different would I be now as a result of that? You know, I can't turn back the clock. But long way of answering, [00:44:00] you know, I would've, I avoided it before and I tell everybody who asks me now that you know, at least try. If you've thought about it, why not give it a shot and just see what works or doesn't work for you?

[00:44:11] Rob Pintwala: Yeah. Yeah. I like that answer. Thank you. And yeah, it sounds to me like you've really . Like your alignment of your values and what you work on day to day. And that, that almost brings me back to the topic of your book and some of the exercises you were talking about. And you know, people's search for greater connection to their values.

[00:44:41] You know, assuming that they've kind of done some work and understand their values. And I think, like, you know, for me, my peers when I was working for different companies would always, you know, want to hopefully align with their values like their employer. And you know, you like what you said about [00:45:00] Airbnb really investing in their people.

[00:45:01] And I think that's fantastic at the time that a company coming from Silicon Valley is competing with Facebook and all these big, you know, super well-funded companies for talent. Kind of have to treat their people in a way that attracts talent, right? I mean, I think most people don't work for a company like that.

[00:45:22] Maybe they don't even work for a company that they really love the product or the service or their values. I think what you've put together in your book is like helping, maybe some of those folks start the process of finding more fulfillment and enjoyment in their day-to-day life. My question is more like, do you think it's an inevitable evolution for people to continue trying to align their work if they have the, you know, kind of freedom and flexibility too with their personal values?

[00:45:58] Or do you feel like [00:46:00] a lot of folks can really just get that fulfillment on their own. With their own prescribed way based on, you know, some of the things that you've alluded to and like written about and like, can you really find fulfillment working for a company that like you don't care about their product or, you know, maybe the CEO is a bit of a dick.

[00:46:21] Jason Silver: Yeah. Again, that's gonna be individual for everybody for sure. But you know, I can live in a country where I don't agree with a hundred percent of the politics and be perfectly happy doing so. And the question is like, how, you know, and at the same point, there's a threshold beyond which if I don't agree with certain aspects of the politics, not to get into politics on your podcast, but we'll keep it like high and light, but like, you know, if that progressed to a certain point, that would no longer be okay for me. a person has to make their own. Choice. I think what off the option that's there for people that I genuinely believe that this option exists from the vast [00:47:00] majority of people and we're just not paying attention to it in a lot of ways because of like, I don't know, messages we've been fed or how, or programs to think about things or whatever it might be. It's this idea of like overnight success. You know, you read about an overnight success, like a company explodes onto the scene as an overnight success. Like, you know, a celebrity explodes as an overnight success. There's not really such a thing. You just, you're just seeing the tip of the iceberg.

[00:47:27] Jason Silver: You're not seeing all of the work and challenges that came before it. And I often think that there are these spots of, like, the problem of enjoying your job seems so intangible, so inact actionable and so out of reach that it's just, I have no agency. And for me, like when we're afraid of something, you know, that's okay.

[00:47:48] Jason Silver: It teaches us not to like touching the stove. It's when it becomes anxiety that it's a real problem. And I think what's kind of sitting in between those two things is agency. If we're afraid and we have no agency to do anything about it, [00:48:00] it can, for me at least, lead to anxiety because I feel like things are outta control here.

[00:48:04] Jason Silver: What the heck am I gonna do when I have some agency? At least I can be working towards it. And I think what happens with a lot of folks is they feel like I have no agency. To your point, the CEO's a bit of a dick, or my manager doesn't let me do X, Y, and Z. Sure. What do they let you do? What do you have at your disposal? And if we can just get away from this overnight success thinking and thinking like, I have to get a new job or make some big massive change to just, what can I do tomorrow? What small thing can I do tomorrow to just start the momentum, pick it and do it, and then see how you feel. You'll feel better, worse, or the same, and repeat that cycle five days in a row. And that's why I suggest the thing that we talk about earlier. String together a couple weeks of every day. Finding one way of doing something you love with the tasks that you have to do, it requires no change to your job. The things that you're being asked to don't have to change. You're just [00:49:00] gonna make tweaks.

[00:49:00] Jason Silver: They could be small at first to how you're going about doing them, and what I think that this does, at least for me and other folks around, is now all of a sudden I have agency. And maybe that leads you down a path where you realize the things you want to do or the way you want to do them is not aligned with the job that you have.

[00:49:16] Jason Silver: And you'll have a choice to make. You might be in a position where you have to keep the job because you need it financially, and you don't have the freedom to go and look for something else and more power to you if that's where you wind up and you know, you choose that hard thing and you figure out how to work that way. For other folks, it might be, maybe I have to change the organization. I don't want to get a new job. I'm very passionate about what we're trying to accomplish, but this isn't how I want to work. I don't want other people like this working around me. You know, let's change the way we're working. For others it might be, I gotta find a new job.

[00:49:44] Jason Silver: It's not the right place. But we often jump to the outcome there of like, I need a new job that's gonna make me feel better. I need that promotion that's gonna make me feel better. I need that project that's gonna make me feel better. Those things might all be true, but we don't need to do anything between now and then. [00:50:00] You can build these small tests and just say, I really like giving presentations. I'm gonna find a way to speak in front of at least two people tomorrow and let's just see. That gave me a lot of energy. I really enjoyed it. Great. I'm gonna make sure that I do this every couple of days now. And once that gets locked in, then you move on to the next one and the next one and the next one And it builds and builds. And that's why I was saying this idea of like, you can practice a job you really enjoy. And the more I thought about it as practice, the more it really started unlocking things for me . I'm gonna practice speaking, I'm gonna practice spreadsheet making. I'm gonna do more of these things. Actually, I have all the agency I need to make progress.

[00:50:41] Rob Pintwala: I love that word agency. I really do. I think it's so powerful. It almost reminds me what you're saying is like self-care at work,

[00:50:50] Jason Silver: Yeah.

[00:50:51] Rob Pintwala: you know, for the therapy terminology almost. Right. And that, and almost like maybe we can sort of spend the last little while [00:51:00] speaking like about for folks that are maybe

[00:51:04] Unsure of what they're feeling, like they're feeling unmotivated by their job or by their company. And yeah, I imagine you looked at a lot of data and talked to a lot of people. I've managed a lot of people and coached a lot of people managing a lot of people around this concept of burnout.

[00:51:21] Like it still seems to me, I've read a lot of articles, we've even written articles about burnout. It still seems to me almost a little bit like unclear of what it is, but also do you think someone who's, and maybe it's on a spectrum, but do you think someone who's burnt out, or maybe it depends on the severity of the burnout or how long it's been,

[00:51:45] Is there anything like that might bridge them to that or do they sort of need the feeling of agency before doing the exercise or just kind of go do the exercise and it'll bring about the agency or,

[00:51:57] Jason Silver: Cool. Great question. I think I got it. Like, I think [00:52:00] what you're saying is, I'm gonna read between the lines. People feel like there are things in the way. How do we break through these barriers?

[00:52:11] Jason Silver: Great. Good question. So small trick there. Also in the book I'm a big advocate of this po possibly the most valuable question I've personally ever learned. I think it's really easy to look at the reasons why we can't do something, anybody, right? This thing can't be done. We don't need to get into all of the, you know, behavioral economic psychology standpoint of this thing. But as soon as the word can't pop out, there's a problem. Because once you hear can't, it's a lot easier to find all the reasons why that is true, meaning why it can't be done. Then try to find counter reasons to that you hear camp from somebody else you think can't to yourself, whatever. The most valuable question I've ever learned is what would need to be true. So for folks that are listening to this and they say like, [00:53:00] I was just about to swear and I'm not, I wasn't sure how we feel about swearing on the podcast and I held myself back, but

[00:53:05] Rob Pintwala: I tried to start swearing just to make it okay.

[00:53:08] Jason Silver: Okay. So for all the people that kind of, you know, are listening and they're like, bullshit, like that might work for you. You have this kind of a role or this kind of a company that you're at, like, that would never work for me. Great. The thing I'll challenge you to do is ask yourself what would need to be true? Well, what would need to be true is I would need to have a chat with my manager. I'd need to get, you know, an hour to think about this tomorrow. And you know, like I would need to take the time to build the presentation as an example from before. Well, okay, how hard are those three things? And I think what we do in that situation and where I see that help so much is when you start with can't, it's self-fulfilling. I don't mean this to feel too self helpy and like preachy, but the alternative is you might get to can't, but let's get to can't as the last option. [00:54:00] It's something we're gonna work our way towards. Well, I can't do this. Well, okay, hang on. What would need to be true? I would need to align with my manager. Okay.

[00:54:06] Jason Silver: What would need to be true to align your manager? Well, I'd have to get project X, Y, and Z done because those are really important. Then I could take this. Okay, well how hard is it to do that? Like could we do those things? Well, we could. Okay, we've got a plan now. And we went from a place where before it felt like can't, for probably some valid reasons because I'm not saying this is easy.

[00:54:24] Jason Silver: You're gonna snap your fingers and it's no work. Like you have to change and do things in a different way. But if you can ask instead, like, I don't have this agency, like what would need to be true for me to get it and get highly specific, right. So we don't wanna live at the generalized level of my job because we don't have enough agency. Great. Like go a level deeper. I want to give more presentations in my company. What would need to be true to give one presentation this week that I otherwise wouldn't have given? It's so specific, it's so short term. It's right in our face. The challenges will become instead of [00:55:00] big insurmountable, how do I even start this? They'll become highly specific, highly actionable. Like I said, I just have to talk to my boss and make sure that a presentation is okay, even though they ask me for an email, okay, you know, let's go and let's go and do that. So this question of what would need to be true and what I like to do for myself and try to, you know, help other folks with as well is paying attention to the word can't. When you hear it, that's when you ask what would need to be true. There is such a big difference between can't, which is about possibility, which for me is about violating a law of physics. That's what can and can't be done. Or, you know, we're not gonna break the law. There's laws of society too. Can't it be about like, what law are we gonna violate? Big difference between can't and shouldn't, is about what we do or don't choose to do. So if you're feeling like you have a bit of a lack of agency, next time you hear someone say, can't to you or you think can't in your head, just take a [00:56:00] half a second, remember this chat and ask, well, what would need to be true? List those things out. It's not that every single time you're gonna go and do the impossible, but more often than not, I've found you will see a list that feels taxable, or at least one thing on the list will be taxable. And you've, you can go and take agency and go and do it.

[00:56:20] Rob Pintwala: Yeah, no, it sounds like you're getting a lot of experience coaching here. Thank you. Yeah, that's fantastic. One quick question aside that popped to mind is are you going to be narrating your audiobook

[00:56:35] Jason Silver: why do you ask that?

[00:56:37] I think it'd be excellent, especially if you can bring in some of the frameworks and get a good tone.

[00:56:43] Jason Silver: I think you're trying to tell me that I've got a face for for radio, which I'll take in a very 

[00:56:48] Jason Silver: positive 

[00:56:49] Rob Pintwala: Well, maybe it's a YouTube video. I'm into audio books now. I don't know more than, I just can't quite seem to get through books very easily 

[00:56:56] Jason Silver: Good to know. Well, I'm gonna make it a personal mission. So fire a book your way [00:57:00] that it's gonna, it's gonna keep you captured, I hope.

[00:57:03] Rob Pintwala: yeah. Yeah, that's also a big unlock, trying to read books that only you're willing to keep turning. 

[00:57:10] Jason Silver: Frankly, that's what's been the hardest. Sorry. It's not that, one of the hard things for me is okay, I want to help people enjoy doing hard things. And when you take that, and I laid it on top of the book, one of the things I realized is reading a book is hard. Let's just be honest. I know we don't like to admit that kind of stuff, but like you have a kid, your life is very busy.

[00:57:31] Jason Silver: You have a podcast, you have work, a book can take you. I don't know, you know, it's probably measured in tens of hours, depending on how fast you read. It can be hard to read a book. I wanna read. I want my book to be the kind of book that you enjoy reading. And the secret to a lot of the stuff I've been writing about is they're highly tactical in nature. And if I just wrote them out for you, you'd be like, nah, this is boring. Like, you would not make it past thing one. And so [00:58:00] for me, I put a lot of time and energy into like, how am I gonna get Rob and anybody else who's wanted to read this book, like really interested in this idea of how to build agency in their day-to-day life. What can I put around that so I'm not just giving you the information to help with this hard thing, but you actually enjoy it and you're like, ah, I'm happy that I read this chapter. It was enjoyable. I laughed once or twice, like, and that has been a real challenge with the book. And I think in the absence of this mission I have for myself, I probably would've just banged out the information and, you know, and like there it is, as short as I can make it. And it's been tough, but super fun. And it's yeah, I think finding ways to make it enjoyable for myself as I'm writing it, because it's hard to write and I want to enjoy the process. And then thinking about the reader and how they're gonna enjoy it has been a crazy challenge. But I'm super excited.

[00:58:53] Jason Silver: Like it's come along very nicely.

[00:58:55] Rob Pintwala: Oh yeah. Yeah. It sounds like a very ambitious feat and, but [00:59:00] worthwhile one. And I do think that the thread that you're pulling on this topic, it's just. To use that tech startup where the total addressable market is just massive, right? Like, everyone's struggling with this. And I think it's just amazing that you're, you know, hopefully gonna be able to get in front of a ton of people, some of these frameworks, managers, employees, students, you know, I think it's incredible.

[00:59:28] Jason Silver: I mean, I'm excited to do it. And you know, one of the most fun things for me to do is the book's fun, but I really love any opportunities to like, get up in front of an audience and talk to them about things like, here's the thing we can go and do. We do all sorts of fun exercises, like with a whole room full of people.

[00:59:44] Jason Silver: And yeah, like I said, getting people laughing about something as mundane as how to communicate better with your colleagues so you don't, you know, wind up wasting time every week on miscommunications is a deep challenge. Super fun. But yeah, I really love the people aspect of it and I'm hoping that [01:00:00] it's gonna really springboard into a lot of time spent talking to folks, working with folks, sharing the message. 'cause I agree. It's the reason why I put the time and attention here, like I just feel like something is so fundamentally broken and the answers that we're trying to put in place, I just don't see them working both anecdotally and empirically when you look at the, when you look at the data as well.

[01:00:21] Jason Silver: So I hope the time is right. We'll see. But you know, like I said, enjoying the journey along the way, so I've Time will tell

[01:00:28] Rob Pintwala: It's incredible. Yeah. So, projected to be released in 2024 or what, and yeah. I know this website live and the newsletter has, is now live and you're giving out tidbits from the book. I see.

[01:00:41] Jason Silver: Yeah, so if anyone wants to check it out, you can go to qci book.com. It stands for quietly crushing it book.com, qci book.com. You can read all about the book there. You can read about me. There's a contact form if you wanna shoot me a note. Would love to hear from anybody you'd like feedback from this chat, or, you know, you want to talk about [01:01:00] sharing some of the stuff we've been talking about here with your company, if that's an interesting thing for you.

[01:01:04] Jason Silver: Cool. You can also sign up for my newsletter there if you do that you get the newsletter, you know, that's the, I guess, most important thing. And there what I do is I basically break out tactics from the book, and I share them on a regular basis that people can use, like every week to deploy at work. It's not just stuff for my book. I spent a lot of time, you know, reading tons, as I said, experimenting for myself and pulling out the specific tactics, like none of the fluff, just like Problem solution. Here's how to try it. And you know, I throw some terrible jokes in there. Again, just to try to make it enjoyable. So qci book.com, you can sign up right there. You'll get a discount on the book when it does come out. I send around a free preview chapter, the first chapter of the book on a tactic that'll help you do five days of work. And four, you get that when you sign up. And then you can email me directly, share feedback, et cetera, et cetera.

[01:01:53] Jason Silver: But would love people to look me up there. Would love to hear from them. I'm around on LinkedIn too. It's not that hard to find there.

[01:01:59] Rob Pintwala: Awesome. Yeah. Jason Silver on LinkedIn.

[01:02:02] Cool, Jason. Well it was a pleasure. Thanks for teaching me some things and hopefully all the listeners as well. And yeah, hope you have an excellent rest of your day.

[01:02:10] Jason Silver: for having me, Rob. Really super appreciate the opportunity and really great to get to kinda share some of the thoughts and hope it was valuable for anybody who's out there listening.

More episodes