Unlocking Happiness and High Performance | Jason Silver

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A New Approach to Career Satisfaction and Professional Growth

Listen in as Jason Silver discusses his new book Your Grass is Greener and how it can help change the way you look at work and life.

Peter Winick welcomes Jason Silver, author of the new book “Your Grass is Greener: Use What You Have. Get What You Want. At Work and In Life.” Jason, an engineer turned entrepreneur, shares his journey from tech to business and how a personal tragedy led him to reevaluate his approach to work and life. While building a company in the AI space and pushing himself to the limit, a phone call changed everything—his sister was diagnosed with late-stage cancer and passed away nine months later. This profound loss forced Jason to rethink his priorities and laid the foundation for his book.

Jason’s mission with Your Grass is Greener is clear: to help high-achievers realize they don’t need to sacrifice joy for success and to empower those stuck in unfulfilling jobs to see they have the power to change their circumstances without changing careers. He believes that passion and performance can coexist, creating a positive cycle where enjoyment leads to better performance and vice versa. Although Jason didn’t write the book as a business venture, it naturally led to opportunities where he now works with executive teams, leaders, and founders to build high-performing, happy teams. His insights on decision-making—highlighted in two key chapters of his book—have resonated widely, uncovering a common challenge in many organizations: decision paralysis. He’s showing leaders how to make faster, more effective decisions by applying practical science, transforming how businesses operate. Writing the book taught Jason more than just communication skills; it taught him the art of engaging storytelling. He learned from his editor, who also worked on Atomic Habits, that effective communication isn’t always about brevity but about connecting deeply with your audience. Jason now sees storytelling as a vital tool for leadership and decision-making.

Jason’s vision for the book is ambitious. He sees Your Grass is Greener as a catalyst for change in the workplace. He believes many are approaching work with a broken mindset, and the solutions we’re currently trying aren’t solving the deeper issues. Instead of job-hopping or pulling back at work, Jason advocates for a different approach: rethinking how we work to unlock massive improvements in both satisfaction and performance.

Balance Ambition with Well-being: Jason Silver’s book, Your Grass is Greener, highlights the importance of finding a balance between achieving professional success and maintaining personal joy. High-achievers don’t need to sacrifice happiness for their goals; it’s possible to enjoy the journey and achieve success simultaneously.

Empowerment and Agency in Your Career: Many people feel stuck in unfulfilling jobs, but Jason argues that you have more control than you think. By leveraging your existing skills and shifting your mindset, you can transform your current job experience without changing careers. This approach can lead to greater job satisfaction and improved performance.

Effective Decision-Making through Storytelling: Writing the book taught Jason the power of storytelling in leadership and decision-making. Clear and engaging communication, rather than mere brevity, can drive deeper understanding and better decisions within organizations. This insight has proven essential in helping businesses overcome decision paralysis and improve overall effectiveness.

Jason shared the very personal origin story of how his book was born. Are you sharing your thought leadership origin story?  Check out this short video by Peter Winick on the power of having an origin story.

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Transcript

Peter Winick 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.

Jason Silver Thanks a ton for having me, Peter. Appreciate it.

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

Jason Silver Condense down so it fits into a podcast, you know.

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

Jason Silver 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.

Peter Winick I don’t think so. You have to do a haiku while writing a unicycle, obviously, because.

Jason Silver And if you know, a unicycle is a thing. I learned how to ride it. 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 write off, 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 big Jack. 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 until the right looked like there. And I was building, a company not too long ago, in the AI space back before I was the cool thing to do very much on the, you know, 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. My oldest and only sister passed away, you know, about nine 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. Tried 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 write a book, let alone be on a podcast. Can I talk to you about it? But there’s the very short…

Peter Winick It sounds like you can.

Jason Silver Cover a lot of stuff.

Peter Winick But, you know, on some level wrote the book you needed to read or needed to write, right?

Jason Silver Yeah. You know. It’s not, I didn’t. It’s set up 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 parents started to notice and they started to really like it. And I got really interested. And, you know, I really want to help people enjoy. Accomplishing hard things like by achiever, but you don’t have to grind it out. You can enjoy the journey along the way. Now, I do think both of those things.

Peter Winick 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, we’re going to sleep two 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 my 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.

Jason Silver Yeah.

Peter Winick And, you know, sometimes it takes somebody burning out or crashing or hitting bottom 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?

Jason Silver Yeah. Good question. I think kind of two people I think about version one. It feels very reductive to simplify it down in this way. But, you know, version one would be somebody who. It’s kind of like the two pieces that you mapped out. Like 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 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. And you don’t have to go and do some big, giant, radical life shift. And that can have a big impact 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 a 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.

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

Jason Silver It’s conscious or not, it doesn’t work. You know, 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, right. And I don’t know why. You know, 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.

Peter Winick But isn’t it isn’t it a function of, you know, wherever you go, there you are. Right? That’s right. Left miserable job because of ABC Indy. And you go to the next job and it’s ABC. And the only thing that changes the logo on your paycheck. Right. Or maybe it’s kind of cool, but there’s a honeymoon period in it. It’s this is that. That’s right. So let’s segue into 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 to talk about that, like who’s hiring you to do what as a result or with this type of work that again.

Jason Silver 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, exact 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 so the marketing department then has to go to finance I. But than that, you know, how can a team of people that’s, you know, greater than just yourself? Ten people, 20 people, 50 people, 500 people a day? 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. And I’m really enjoying sharing that kind of stuff.

Peter Winick That’s interesting because lots of organizations are obviously 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 this compounding thing on top of things, on top of thing. And to make a decision where you’ve got the right far five smart people in the room or in the zoom, you can get the decision made intellectually. Yeah, well, I tell you, you know, I.

Jason Silver 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 tackle them are decisions I’m making. Decision making isn’t taught. It’s a shocking thing to me. Like you can’t, some of 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.

Peter Winick I think they teach it indirectly as maybe critical thinking or systems thinking or whatever.

Jason Silver Components of decision making. But they.

Peter Winick Yeah. And sometimes over complicate. Right. So, 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, 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 the ranks a little bit, etc.. And 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 five-star review at rate this podcast.com/l t l and share it with your friends. We’re available on Apple Podcasts and on all major listening apps as well as at thought leadership leverage.com/podcast. So I know you said earlier, which I love that you didn’t set out to write a book, but you did write. What is that? Yeah. So yeah, exactly. We have it. All right. 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 exactly. What was the most surprising to you about the process?

Jason Silver Most surprising is hard. But, I’ll tell you, I thought. It’s a great 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. And the lesson that I learned. But 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.

Peter Winick Yeah.

Jason Silver The thing that I learned the most, and, I credit this largely to what 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 is going to get a note for me or a memo for me.

Peter Winick Yeah, yeah.

Jason Silver And here are the three 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, you 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 editors show me is, here’s how you can 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 is a time to prioritize efficiency.

Peter Winick Interesting because you know, the executive summary, idea, concept, format, whatever the premise under that is. All right, get what you got to get out to a super busy executive who’s multitasking. He 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 back. Yes. No. Maybe sell. 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, etc., etc. 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.

Jason Silver Yeah, I think it’s about thinking about, you know, the brief executive summary approach certainly has its place. Yeah. If the thing you’re trying to do is I got to 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 got to 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. Just thinking about the context in which you’re in, what you’re trying to communicate. I 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 effectiveness of it and thinking about storytelling, I think, is. It’s real.

Peter Winick 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 at or whatever, and then ask yourself, well, what was the story? And I was like, no, like my, my worst nightmare is like somebody throws up the PowerPoint and there’s like 87 data points on there in two months, and then they proceed to read them because I can’t read, obviously. So great numbers out loud to me, but.

Jason Silver I can tell you can’t read by the bookshelf behind you.

Peter Winick 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 Carly lives, but it’s where do you see this going? It’s a great.

Jason Silver Question. You know, I think and. 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 micromanager 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 lean 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, I think the biggest flop would be if nobody ever reads it, has any opinion about it. Good, bad. You know.

Peter Winick What I hate at least means you got a reaction, right?

Jason Silver Right? Right, right. That’s right. You have a face to throw.

Peter Winick Yeah. Indifference is worse. Like I read it and I have no thoughts like that’s the.

Jason Silver Most likely.

Peter Winick What’s been great. I appreciate your time, Jason. I wish you the best.

Jason Silver Thank you. Thanks Peter.

Peter Winick To learn more about Leadership Leverage, please visit our website at ThoughtLeadershipLeverage.com to reach me directly. Feel free to email me at Peter at ThoughtLeadershipLeverage.com, and please subscribe to Leveraging Thought Leadership on iTunes or your favorite podcast app to get your weekly episode automatically.