Unlocking Happiness and High Performance | Jason Silver | 592

And welcome, welcome, welcome. This is Peter Winick. I'm the founder and CEO at Thought Leadership Leverage, and you're joining us on the podcast today, which is Leveraging Thought Leadership. Today, my guest is Jason Silver, and Jason just wrote a book called Your Grass Is Greener: Use What You Have, Get What You Want at Work and in Life. And before I get into all of the backstory and all that, I'd rather just ask Jason directly. So welcome aboard, Jason.

Thanks a ton for having me, Peter.

Appreciate it. Yeah. So give me a little bit, because you've got a fascinating sort of background and then the sort of the origin story for this, this work and where you're going with it. So give us like the, the short version of Jason's life story, if you will.

Yeah, condense it down so it fits into a podcast, you know, the—

and if you could do it as a haiku, people always like that. I get a lot of requests for that.

I only know how to do it in haiku, so, you know, here, here we go. It's a blatant lie. It's not even going to rhyme. I guess a haiku doesn't need to rhyme, but, uh, I don't think so.

But you have to do a haiku while riding a unicycle, obviously, because—

and you know what, a unicycle is a thing I learned how to ride. I had this thing where I was just like, if I see someone else do a thing, I should be able to figure it out. And so I was the kid in the backyard with like a unicycle falling all over the place until I could ride it. But, uh, I doubt I still could. But yeah, you know, long story short is, as with many folks, you know, lots of good stuff, some challenging stuff sprinkled in. Engineer by training, founded a couple of startups, realized I was more interested in business than being purely in tech. I like the business side of tech. Founded a couple companies, crashed a company, which is always an interesting story. I was lucky to be at Airbnb in its early days, so I got to see what the up and to the right looked like there. And I was building a company not too long ago in the AI space, back before AI was the cool thing to do. Very much on the treadmill of like, how many hours am I working? How hard can I push? You know, overachieving, whatever you want to call it. And I had the hardest experience of my life. I got a phone call from my sister. And she was in the hospital. She had gone for a regular checkup and it was very bad, very bad news. Found out she had a very late stage, very aggressive form of cancer. And my oldest and only sister passed away, you know, about 9 months after that. And it was a terrible experience that pushed me to completely rethink the way I was living my life.. And, you know, out of the whole grief cycle, trying to help myself not crash, I learned some really valuable lessons that wound up becoming Your Grass Is Greener. You know, never thought I would, I would write a book, let alone be on a podcast, gonna talk to you about it.

But there's the very short, you know, it sounds like you covered a lot of stuff, but, you know, on some level wrote the book you needed to read or needed to write.

Right. Yeah. You know, it's funny. I didn't, I didn't set out to write a book, kind of resisted it.

Yeah.

You know, I learned a bunch of these lessons and they started to help me improve my life, particularly what was going on for work at me. And my, my team started to notice and they started to really like it. And, and I got really interested in, you know, I, I really want to help people enjoy accomplishing hard things, like be a high achiever, but you don't have to grind it out. You can enjoy the journey along the way. How do you do both of those things?

It's usually not a message we hear in the same breath. It's usually an either or. Hey, if you're not a high achiever, you know, you do the Gary Vee thing, grind it out, side hustle, blah, blah, blah, blah, blah. You know, sleep 2 hours a day. Here's the hacks. And it's all about getting more done in less time and whatever. And then there's the other side of it, which is, well, what's the point, right? Am I happy? Am I fulfilled? Am I— Why am I grinding it? And you're looking at both of those things in one place. And I think that's interesting because as humans, they do live in one place, right? We don't have these separate sections. And, and you know, sometimes it takes somebody burning out or crashing or hitting bottom or, or whatever. So who do you hope internalizes this type of thinking, these ideas, and what is it that you hope they do differently as a result of being exposed to them? What's the before and after?

Yeah, good question. I think kind of two people I think about. Version 1, it feels very reductive to simplify it down in this way, but you know, version 1 would be somebody who— it's kind of like the two pieces that you mapped out, like they're, they're crushing it in their job, but they're being crushed in the process. Yeah. And I would like them to learn and see as I learned that you don't have to give up on your ambition to enjoy the journey along the way. Like, the, the joy and the accomplishment, they can coexist. You don't only have to enjoy it when you accomplish this thing that's going to happen in your life. And then at the same time, you might be somebody who, you know, is working in a job feeling like it's just not really working out. Lots of people are in that spot, you know, work just isn't working for them. And I'd like to show them how You actually have a lot more agency than you think to change the job you already have using the skills that you already have built. You don't have to go and do some big, giant, radical life shift, and that can have a big impact on, on your work. And the reason why is a lot of research shows, not shockingly, but we ignore some of this stuff, like the more you enjoy what you're doing, the better you do at it. The better you do at it, the more you enjoy it, and you get this amazing flywheel going. And because we spend so much time at work, the better you do at work and the more you enjoy your job, it just spills over into the rest of your life, which spills back into work. And it's like this amazing, you know, up into the right flywheel that you can build for yourself.

Yeah. And that assumption of agency is great because, you know, the, the answer of, well, it's not a cultural fit, this is the way that we do it. The answer for a lot of people of just leave is kind of a pompous answer, right?

It's pompous or not, it doesn't work. You know, they've, they've done a lot of research again to show the Great Resignation was a great experiment.

Yeah.

And, you know, we look back now and all these people, millions of people change jobs. 80% of those people regret the change that they made.

Right, right.

And I don't know why. I can't speak to every one of those people. It would be pompous of me to say I can tell you exactly what all of those millions of people did wrong. I don't know.

But, but isn't it, isn't it a function of, you know, wherever you go, there you are, right?

That's right.

Miserable job X because of A, B, C, and D, and you go to the next job and it's A, B, C, and D. The only thing that changes the logo on your paycheck, right? Or maybe it's kind of cool if there's a honeymoon period.

It's cool.

It's this, it's that.

That's right.

So let's segue into the, the business side of this because you didn't do this to launch a business or a practice or whatever, but there is a business underneath this. So talk about that. Like, who's hiring you to do what as a result or with this type of work that—

Yeah, you know, I think the book The book, I'm, one of the things I'm most proud of with the book is it didn't start as a business idea. It really started as a purely creative endeavor and I wanted to write the best book possible and some great stuff has come out of that. You know, I spend my, in quotation, day job working with people that are building companies, exec teams, leaders, founders, things like that on how to build high-performing teams that are loving what they're doing. And one thing that's come out of the book that has been great is there's two chapters in the book on decision-making, how to do it better and how to do it faster. And as more people have been getting exposure to the book, we've been finding that decision-making is just like broken in so many companies. You know, people are waiting forever and ever and ever for a decision. They know what they need to do and they're waiting for it to get signed off by this person and pass to the marketing department, then has to go to finance and blah, blah, blah, blah, blah, blah, blah. You know, how can a team of people that's, you know, greater than just yourself, 10 people, 20 people, 50 people, 500 people, right? How can you make decisions better and faster so your company does better and it does it faster and your people don't get so frustrated? And so that's been a big thing that's been coming out of it and getting a chance to really show people how to apply a lot of the science that's out there, because most folks don't have time to be a nerd like I am and read all the books on decision-making and like, what are the big things that get in the way? How do we speed up decision-making? How can that impact my day-to-day job? Has been like amazing to see the impact coming out of that. I'm, I'm really enjoying sharing that kind of stuff.

That's interesting because lots of organizations, obviously there, there's systems, there's rules, there's processes, all these things, and they all were installed for a reason at a moment in time. But then there's what I would call the attic effect, right? There's just this compounding thing on top of thing on top of thing. And to make a decision where you've got the right are 5 smart people in the room or in the Zoom, you can get the decision made intellectually.

Yeah.

Well, I think— kill you, you know.

I think a thing that's really interesting is, is like decision-making is such a fundamental skill, right? Like everything we do is a decision. I have a million thoughts all day long. Which ones I choose to act on and how I choose to act on them are decisions I'm making. Decision-making isn't taught. It's a shocking thing to me. Like you can't, to the best of my knowledge, like come up through school and get a class on here is the discipline of decision-making. When people go through professional development in their work, yeah, they're not saying like, hey, you should go and take a course on decision-making, or let's like up your decision-making capabilities. It's just not a thing that's taught. And I think there's been a bit of a vacuum there.

I think they teach it indirectly as maybe critical thinking or systems thinking or But that's components of decision-making, but they— Yeah. And sometimes overcomplicate, right? So, uh, I, I think that's important. I think the other side of that, there's so much frustration where people that want to do the right thing and make the right decision might take less than an optimal path.

Yeah.

Because it's easier to get the second thing through the system, even if it's not optimal because it requires a different approval or different processes has to go up. Up the ranks a little bit, etc.

Yeah.

If you're enjoying this episode of Leveraging Thought Leadership, please make sure to subscribe. If you'd like to help spread the word about our podcast, please leave a 5-star review at ratethispodcast.com/LTL and share it with your friends. We're available on Apple Podcasts and on all major listening apps. As well as at thoughtleadershipleverage.com/podcast. So I know you said earlier, which I love, that you didn't set out to write a book, but you did, right? What is it that— Yeah, so exactly. We have a— So what is it that you learned or was surprising to you going through that? Right? Because you don't know what you don't know. It's that point. What was the most surprising to you about the process?

Most surprising is hard, but, uh, I'll tell you, I thought it's the right way to get this thought out of my brain. This is an ironic thing to sputter on given what I'm about to tell you, uh, the lesson that I learned, but the, the amount that I've learned about communication through writing a book has been surprising. You know, you always hear like, write down your thoughts, it makes them clear. All that stuff is true. You know, you write it down, it's cleaner, it's more precise. You whittle it away. Yeah, I think that I learned the most, and I credit this largely to an editor I got to work with. You know, he was one of the editors on Atomic Habits, and I was always a business communicator, right? So if I have to get an idea across to Peter, like, Peter's going to get a note from me or a memo from me.

Yeah, yeah.

And here are the 3 bullets at the top. This is the key takeaway stuff you need to get, and then here's all the information. Turns out that's really boring. Like, brevity is boring. And if you're going to get someone to read a book, and I'm going to get a concept to land in your head, especially when it's business, like, it can't be boring. You probably won't make it through the book if it's boring. And even if you do make it through the book, if you don't tell a good story, it won't stick in your mind. And what my editor showed me is, here's how you could take your ideas and really draw people into them as you're getting them across. And what that did is it made me rethink the way I'm communicating with people in general. You know, when I have something to share with Peter, it's not just about what is the minimum number of words that I can use to get the critical point across. It's actually sometimes, often the most efficient is not the most effective. And there's a time to prioritize efficiency.

Interesting because, you know, the executive summary idea, concept, format, whatever, the premise under that is, all right, get what you gotta get out to a super busy executive who's multitasking and doesn't have time to go deep. Right? You know, here's the, I'm asking for, here's why, here's the return on the budget, bang, bang, bang. And they could look at that, yes, no, maybe so, right? Whatever. There doesn't necessarily need to be an emotional arc to that. There doesn't necessarily need to be the story of why, et cetera, et cetera. But I would argue if you were making that same case in front of that person instead of via email or something like that, the story is the more powerful way to go.

Yeah, I think it's about thinking about, you know, the, the brief executive summary approach certainly has its place. Yeah. If the thing you're trying to do is, I gotta give this executive the information that they need in the cleanest, fastest way possible so they can make a decision and get it back to me, that's different than, I gotta get this executive to think deeply about this thing that's important, and I need them to understand why I'm bringing this to them. And I really want them to put some good hard thought into it, not just like, you know, yes, next, check, next, next, next, next, next, next. Just thinking about the context in which you're, in which you're trying to communicate a thing is really important. And I'll tell you, like, you can't get a lot of the nuance across in bullet points. And sometimes a lot of the important information is in the nuance. And so finding a way to balance the efficiency and the effectiveness of it and thinking about storytelling, I think is really important.

Well, I think the proof of that is when you think about some of the worst meetings you've been in or presentations you've been in or whatever, and then ask yourself, well, what was the story? And I was like, no, like my worst nightmare is like somebody throws up the PowerPoint and there's like 87 data points on there in 2 bullet And then they proceed to read them because I can't read, obviously. So you read numbers out loud to me.

I can tell you can't read by the bookshelf behind you.

Yeah, right, right, right. But they're not adding anything to it. Like, I can take in the information, but what is it that you're trying to get me to do? Either the story, you know, you're telling a story through a spreadsheet. You can tell stories through spreadsheets, right? But you have to, you have to bring it to life, right? Interesting. Anything You know, as we start to land the plane here, what are your hopes for the next, I hate to say chapter of the book, but the chapter of the IP and the thought leadership? The book is just one place it might live and currently lives, but what's, where do you see this going?

It's a great question. You know, I think the simple but not easy answer is I really genuinely feel that work is broken for a lot of people right now, and I want the book to have as big of an impact on that as possible. And at the end of the day, I decided to publish it as a book because I think that there's a narrative that's missing. You know, the things we're trying to do aren't solving the problem. Switching jobs, pulling back at work, you know, these kinds of things aren't really scratching the itch that folks have, and they just need a different way. And I really wanted to address the like, right, hey, if you just work differently, You can have all the same work you need to do. Doesn't matter how micromanaging your boss is. You can just change your approach on some things and you'll see a massive, massive shift.

Right.

And I think getting that out to as many people as possible is the most exciting prospect for me and seeing, you know, what's going to bounce back from that. And that's what I'm most excited about is how does the book, how does the book land with people? You know, you think about a flop, sometimes people will say, Oh, the book would be a flop if people hate it. You know what? I think the biggest flop would be if nobody ever reads it, has any opinion about it, good, bad, you know, that—

Well, hate at least means you, you, you, you got a reaction, right?

That's right. That's right. That's right. Yeah. I have to face it through.

Yeah. Indifference is worse. Like I read it and I have no thoughts. Like that's, that's the most—

Exactly.

Well, it's been great. I appreciate your time, Jason. I wish you, wish you the best. Thank you.

Thanks, Peter.

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