← Passion Struck with John R. Miles
Passion Struck with John R. Miles
Jason Silver on How to Use What You Have to Get What You Desire | EP 527
01:11:41
In episode 527 of Passion Struck, host John R. Miles welcomes Jason Silver, a multi-time founder, startup advisor, and author of "Your Grass Is Greener: Use What You Have, Get What You Want at Work and in Life."
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- [00:01]
Jason Silver
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- [00:40]
John R. Miles
Your phone and we'll pay it off up to $800. See how you can save on every plan versus Verizon and at&t@t mobile.com KeepAndSwitch up to four lines via virtual prepaid card. Allow 15 days qualifying unlock device credit service ported 90 plus days with device and eligible carrier and timely redemption required. Card has no cash access access and expires in six months. Coming up next on Passion Struck.
- [01:05]
Jason Silver
The way I tend to think about that is what I have control over are the decisions that I make. And if I'm clear with my intention, I might not get the outcome that I want, but I'm going to be trying to accomplish it in a way that I'm proud of. And I think the challenge happens when, hey, it's five years later and I look back and I say, oh, I have nothing that I wanted. It's terrible when you look back and you say, geez, I didn't do the things I wanted to do and now I'm in a position where I don't have the things that I want. That's different than looking back and saying, you know what? I'm proud of the way I tried to accomplish these things and it didn't work out in exactly the way that I wanted it to. Let's figure out how to do whatever it is we're going to do with the situation that we're in right now.
- [01:45]
John R. Miles
Welcome to Passion Struck. Hi, I'm your host John R. Miles, and on the show we decipher the secrets, tips and guidance of the world's most inspiring people and and turn their wisdom into practical advice for you and those around you. Our mission is to help you unlock the power of intentionality so that you can become the best version of yourself. If you're new to the show, I offer advice and answer listener questions on Fridays. We have long form interviews the rest of the week with guests ranging from astronauts to authors, CEOs, creators, innovators, scientists, military leaders, visionaries and athletes. Now let's go out there and become Passion Struck. Hey Passion Struck Tribe. Welcome to episode 527 of the Passion Struck Podcast. Before we dive into today's transformative conversation, I want to take a moment to thank each and every one of you for being part of this journey. Your dedication to growth and intentional living is what makes this community so powerful and I'm incredibly grateful for your support. If you're new here, welcome. You've joined a movement that's all about living purposefully and we're thrilled to have you with us. Earlier this week, I had the privilege of speaking with the insightful Eric Edmeads who shared his powerful strategies for lasting health transformation. We explored how small daily choices can impact our well being and even help us reverse chronic conditions like type 2 diabetes. If you're interested in practical science based strategies for optimizing your health, be sure to check out that conversation for our newer listeners. We've made it easy to jump into our content with our Episode Starter packs. With over 500 episodes, it can be tough to know where to begin, so we've curated playlists on themes like leadership, mental health and personal growth. You can find them on Spotify or@passionstruck.com Starterpacks and this is a great way for sharing this with your friends and family. And for those wanting to take these insights even further, our Live Intentionally newsletter provides exclusive content, exercises and tools to help you integrate these lessons into your everyday life. Sign up@passionstruck.com to join our community of purpose driven change makers. I'm also honored to share that the Passionstruck podcast recently won the gold medal at the 2024 Davey Awards in the category of Social Good. This award holds special meaning for me as our winning episode honored the legacy of Emile Bruno and his profound work in conflict resolution and empathy. Emile's story, shared in episode 504, is a reminder of the transformative power of empathy and intentionality in creating positive change. Winning this award is a testament to the impact that we're making together and to our mission of making intentional choices that help shape a better world. Now, today, we have a truly transformative episode for you. I'm sitting down with Jason Silver, a multi time founder, startup advisor and the author of youf Grass Is Greener. Use what you have, get what you want at work and in life. Jason's journey has taken him from pioneering AI startups to advising companies valued at over 2 billion but what truly sets him apart is his philosophy on redefining career satisfaction. Jason's new book challenges the notion that fulfillment at work means landing a dream job or making a huge career switch. Instead, he guides us to transform the work we're already doing, utilizing the skills we already have to create a more fulfilling and balanced life. His strategies are refreshingly practical, like how to do 5 days of work in 4 Advance your career without burning out and find genuine satisfaction right where you are. Jason's mission is deeply personal. After the tragic loss of his sister, he became passionate about creating a life with more meaning, both in and outside of work. Through his experiences, failures and successes, Jason has built a framework that empowers people to make work a positive force in their lives. Today, we'll explore his insights on reframing workplace challenges, making faster decisions, and cultivating a career that feels both rewarding and manageable. This is an episode packed with actionable advice and profound wisdom, so let's dive in. Thank you for choosing Passion Struck and choosing me to be your host and guide on your journey to creating an intentional life. Now let that journey begin.
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Jason Silver
After investing billions to light up our network, T Mobile is America's largest 5G network. Plus right now you can switch keep.
- [05:56]
John R. Miles
Your phone and we'll pay it off up to $800. See how you can save on every plan vs Verizon and at&t@t mobile.com Keep and switch up to four lines via virtual prepaid card Allow 15 days qualifying unlock device credit service ported 90 plus days with device ineligible carrier and timely redemption required. Card has no cash access and expires in six months. Guys, the only thing worse than losing your hair is waiting forever for it to grow back. That's why you need hims, where you can start seeing results in just three to six months. HIMS offers doctor trusted clinically proven hair loss treatments with ingredients like minoxidil and finasteride that actually work. The best part? The whole process is done from the comfort of your couch. You can choose chewable oral spray or serum options to fit your routine. It's 100% online. Just answer a few questions and a medical provider will determine if treatment is right for you. If prescribed, your treatment is discreetly delivered right to your door. Start your free online Visit today@hisss.com Passionstruck that's hims.com Passionstruck for your personalized hair loss treatment options. Results vary based on studies of topical and oral minoxidil and finasteride. Prescription products require an online consultation with a healthcare provider who will determine if a prescription is appropriate, restrictions apply. See website for full details and important safety information. I am so honored and thankful today to have Jason Silver on the passionstruck podcast. Welcome, Jay.
- [07:43]
Jason Silver
John, thanks a ton for having me. Really appreciate it.
- [07:46]
John R. Miles
Jay. It's such an honor for you to be here. I really appreciate you reaching out to me and making a case for talking about your life and more importantly, your book, your Grass is Greener, which just recently launched. Congratulations on that.
- [08:02]
Jason Silver
Thank you. Thanks a ton. When you go through these things, you think about how you're going to promote the book. And for me, speaking on podcasts is amazing. It gives me an opportunity to do a couple things at once. I get to meet awesome people like you and have great conversations and talk about the book and hopefully help folks that are listening, which is great. And listen to a bunch of podcasts. Came across yours. Really interesting. I'm like, got to reach out to this guy and you wrote me back. Something I really appreciate. He said, thank you for writing this yourself and sending it to me yourself. And I think that's the best way to do it. And I was really excited to get the response from you and very excited to see where our conversation goes today.
- [08:39]
John R. Miles
Well, awesome. I think it would be great for both myself and the audience to learn a little bit more about you. Can you discuss your upbringing and what were you passionate about growing up?
- [08:52]
Jason Silver
Upbringing and passion growing up. Good question. So I was born in Toronto, very lucky to have, I guess what you would call a very positive upbringing. A very caring family. Parents always supported me, and I think that kind of set me up to have an ingrained thing where I don't mind going after what feels crazy. Sometimes I'll do things and someone will say, like, how did you figure out that this was okay? People use the word like courage. It doesn't feel like that in the moment. It just feels right to me that when everyone's looking left, I tend to just have a tendency to go right. And that started relatively early. I got very interested in technical stuff, went to engineering school when a lot of my friends were doing very different things. Wound up getting a job as an engineer and did that for a little while and realized pretty quickly that I really enjoy problem solving, but I really like the people side of building businesses. And that's when I, you know, did the first kind of crazy thing. I left a job that was going really well by all conventional measures, and I found a startup. I didn't want to go to business school. I Had done a master's in engineering. I found a startup and said, hey, I think I can do business development. Nothing on paper says I can do it. How about I just come here and effectively work for free for a little while and let's see how it goes. Got very lucky. The CEO leadership there took me under their wing and gave me the whole, you could sit here, take notes, don't say anything, and learn as you go, which was awesome. Got an on the job mba and from there got very interested, very passionate in how do I build companies. Founded a couple. I was very early on, I was early on at Airbnb, which is great. Built an AI company back and forth was like the coolest thing on the planet, planet to do. And the thing I learned over time that I was most passionate about was I loved building businesses. But the reason why I love building businesses is because it creates a place for people to like, flourish. Right. How do I, like, figure out a way to make a company that allows people to do the best work of their lives that they're really proud of. Which has led me into this next phase and why I'm here. Talking about my book that I wrote and talking to you.
- [11:02]
John R. Miles
I want to talk to you a little bit more about Airbnb since you were there in the early days. I have a friend, Jim McElvey, who's repeat company founder. He was the co founder of Square, if you're not familiar with them, and actually mentored Jack Dorsy before they founded Square. But Jim tells me that the biggest reason that he sees companies fail is because they come up with this problem that only they can solve. Yet when things get tough or they need to find money, something else, they get distracted from the main thing, which was the problem they needed to solve in the beginning. And I look at Airbnb as someone who succeeded against all the odds. And if you look at the beginning of the company, there were so many times that the founders could have given up and it might even exist today. What was it about them that allowed them to stay the course and to stay committed to solving the problem in their unique way.
- [12:09]
Jason Silver
I should be clear, joined the company at a very amazing time. It was out of the very early stages. It was hundreds of people, not the thousands that it is today. And I got to experience an extreme up into the right that they had created. So in a lot of ways, I was the fortunate benefactor and jumped in at a really fun time. But a thing that always stood out for me. There is two things I think were always Pretty clear. Number one is you want to marry the problem, not the solution. It's an expression that comes up all the time. What problem are you trying to solve and how do you do an incredible job at that problem? And something that Brian, the CEO, talked about all the time, it was advice that he got early on is my understanding is it's better to have 10 people that love what you do than 100 people that kind of like it. And so we were constantly pushed and thinking about, yeah, this thing needs to scale, but how do you make sure you're creating an incredible experience for the people that really care about what you're doing and then trusting that's going to have the halo effect and the knock on effect that you want to have from there. And the second was don't kill the culture. What is the culture of the company? How do we show up to work every day? How do we work around each other? How do we treat each other? How do we treat customers? How do we treat users? How do we treat investors? Whatever. And being very cognizant of this matters a lot. It doesn't necessarily show up as a traditional business metric. There might not be a through line to what it means for revenue, but I felt a super strong culture there. When I joined. It was clear and evident that it was a big moving force in terms of how the company was working to get towards the outcomes that we all wanted to hit. And it didn't waver over the time that I was there while the company scaled incredibly quickly. And I think that did a lot to make sure that, yes, we're focused on the problem. We're focused on it in a very specific way, trying to get the right people to really love it. And we're very focused on the way we show up and how we do our work and how we show up for each other and our values and making sure that those don't get eaten as we scale up.
- [14:14]
John R. Miles
And I happen to see Brian on Jordan Harmiger's show and this was right either during the pandemic or right after it. And it was really interesting because at a time when people were holding onto their money, he did something very interesting and convinced the board to go along with it. And that was he took all the cash that they had on hand and he actually gave it all back to his hosts because he knew if he didn't take care of the host that they wouldn't be able to survive what was going on with their revenue streams going away. And then he did an even more interesting thing. Which was he went back to the market and then tried to raise another 3 billion while he was giving money away. Which when you think of what he was doing, it's really counterintuitive to that period of time.
- [15:07]
Jason Silver
So, yeah, it's counter to the what other folks might do. And it's directly in line with what I would expect, the decisions being made inside of Airbnb and I heard the expression a while ago, I'll probably butcher it. But it's something like, your values are what you're prepared to pay a price for. Right? It's really easy to live your values when everything's going great. It's really not hard to say we believe in our hosts or we support our customers or we support our people or whatever it might be. When everything's going great, you're not paying much of a price for it. But I really do believe that your values are what you're prepared to pay an active price for, to lose something over. I'm not shocked by Brian's decision because it's a very values based decision. The right thing to do is to help our hosts in this situation, which is directly in line with the values of the company, come what may. And if that costs us, we're going to have to figure it out. But that's the price we choose to pay. And now when I work with companies, it's something I talk to them about all the time, companies, and they have 10 different values. And I'm like, if you're paying a price for all 10 of these values, we're going to be out of business pretty soon. You can't pay all these prices all day long. You're going to get whittled down to nothing. Truly. What are you willing to pay a price for? That's really what the value is inside of the company. And that's why I think Brian means when he says we need to make sure the values stay alive. And that's something that is very easy to lose sight of, particularly when things are not going well. But that's when you need them the most.
- [16:33]
John R. Miles
I love that. And I think one thing you just said there really speaks to the purpose of this whole podcast and that you've read my book. I'm all about the importance of living intentionally. And I think when we live intentionally, it's recognizing those points when we are on that glide path and we're living our values because that's when things seem to go the smoothest. But also recognizing when you're not living your values, because I think that's when in life we face the most hardships. What's your thoughts on that?
- [17:06]
Jason Silver
Intent drift is a real thing. People talk about regret all the time and I don't have a perfect answer for it. I like the way Bezos talks about it, like regret minimization. And for me, the way I tend to think about that is what I have control over are the decisions that I make. And if I'm clear with my intention, I might not get the outcome that I want, but I'm going to be trying to accomplish it in a way that I'm proud of. And I think the challenge happens when, hey, it's five years later and I look back and I say, oh, I have nothing that I wanted. It's terrible when you look back and you say, geez, I didn't do the things I wanted to do. And now I'm in a position where I don't have the things that I want. That's different than looking back and saying, you know what? I'm proud of the way I tried to accomplish these things and it didn't work out in exactly the way that I wanted it to. Let's figure out how to do whatever it is we're going to do with the situation that we're in right now. But I think the real problem comes into play when are you clear with your intention. It's one of the things that I really loved about your book and felt really aligned with is I don't think in general we tend to take enough time up front to say, what's my intention here? What's important to me? Why is this thing important to me? Okay, let's go in and accomplish it. We tend to put all of our time and energy and focus and feelings of success around the outcome, which you can do all the right things and not get the outcome. You can do all the wrong things and luck into the right outcome. I think we're way overweighting the value of the outcomes. So big plus one for me on trying to be much more intentional upfront.
- [18:38]
John R. Miles
I'm a believer of not focusing as much on the outputs, but focusing on the inputs because that becomes the micro choices that you make every single day that determines your long term trajectory.
- [18:50]
Jason Silver
Yeah, I read a book, I often will make little kind of notes in the margin just to help stick it in my head. And I stopped because I was like reading your book and I was like, yep, yes, okay. I think I'm looking forward to the chat with John. We have a bunch of things in common which I think would be fun. Fun to find something we don't have in common too. Those are always good points as well.
- [19:06]
John R. Miles
Jay, I want to ask you another question about who you are so we can get to know you even deeper. I think that throughout my life there are people who have come in and out of it and sometimes there are those people who do seemingly little thing for you that end up staying with you forever. Has that ever happened to you?
- [19:33]
Jason Silver
I paused. Not because I'm trying to think of the one time that it happened. It's more because I'm trying to think of the many and what's the right story. It's funny, I find even the other way around. You talk about intent. I have always put a lot of time and energy and thought into like, how am I helping John in this situation? What can I do that would be, you know, great for John? And sometimes you come up with these big elaborate plans and oftentimes I find that the feedback I hear from people years later about the things I've done for them, that has been the most impactful is the thing I didn't even think about. I was like walking out of a meeting room and you happen to mention a thing and all of a sudden that was very impactful for them and it's a big huge moment in their life and you didn't even realize it. Back to the idea of values. And I've been very fortunate that I've had many moments like this where people have shared an important tidbit of wisdom with me that has like really helped me change the way I think about something where someone has taken an interest in my life and given me a really hard push that they maybe didn't need to. And that helped me rethink the way I was thinking through some stuff. I've had lots and lots of times where I've been talking to somebody and they think to themselves, oh, if Jay went and talked to this person, it might really help them. And they take five seconds and make a connection. And that five second connection turns into a massive win. To circle back to the conversation we had earlier. I've had a very non straight line career, so I've built a bunch of companies. I raised money and crashed a company once, which is always a fun conversation if you're interested in it. But what came out of that was I basically thought I had ended my career. I was relatively young at the time. I had raised money, I had hired people, crashed the company, returned very little of the investors money, had to let go of everybody thought I was a total, absolute abject failure. One day I get a phone call from one of my investors whose money I almost entirely lost. He says, jay, there's this great team. I think you might be interested in what they're working on. I'd like to make a connection. Would you be okay with that? You cannot say no to that kind of a of a response from someone whose money you've lost. Of course, that team turned out to be Airbnb. I got a job there. It was incredibly transformative for me. This is a person whose money I almost entirely lost, who had every reason to be like, I don't want to talk to this human being again. And they took the time to say something about the way that Jay held himself as we went through this process. Really rubbed off positively, I assume, on him. Let me make a quick phone call. I think he'd be a great fit here. It's going to be great for everybody. Turned into an incredible path for me. One phone call, one moment of kindness from a person who had every reason not to not to deliver to me in that way and certainly change the trajectory of my the holidays are here.
- [22:18]
John R. Miles
At the Home Depot.
- [22:19]
Jason Silver
So let's get to decorating.
- [22:21]
John R. Miles
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- [22:49]
Jason Silver
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- [22:54]
John R. Miles
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- [23:24]
Jason Silver
And no overdraft fees. Just ask the Capital One bank guy. It's pretty much all he talks about in a good way.
- [23:31]
John R. Miles
He'd also tell you that this podcast is his favorite podcast too.
- [23:35]
Jason Silver
Aw, really? Thanks. Capital One Bank Guy.
- [23:38]
John R. Miles
What's in your wallet? Terms apply.
- [23:40]
Jason Silver
See capitalone.com bank capital1na member FDIC.
- [23:47]
John R. Miles
Thank you for opening up that and there have been, like you said, it's hard to pick just one because I've had so many myself. But I remember a time I was at Catalina Marketing at the time I was over all the technology decisions, but I had a partner on the product side and he sold this whole concept to the board that he wanted to implement. And then at the end of the meeting basically turns to the board never mentioned it to me and all responsibility for it over to me. And I was really upset about it for a while and a person came to me and said, you, you need to come to the realization that whether you wanted this or not, it is now your baby to own and the sooner you take ownership of it, the better the outcome is going to be rather than you being spiteful over it. So it we were well on the way to starting to make it happen. And a critical part of the strategy was coming up with a new kind of business model for underpinning how the company was operating. And we were in a business where we were pushing. So what Catalina did was they were one of the companies, if not the first company, who was doing mass marketing of coupons in a personalized manner. But the way we operated is we push all that content. And a huge component of this new strategy was instead of us being a push, it was more a pull. So it was changing the business from only offering high CPM model promotions to being more like Google Ads where someone could come on to the platform at and at any time, look at what inventory space we had and decide how they wanted to run their campaigns. And when the CEO and the board ultimately wouldn't shift the model from push to pull, it had grave ramifications that have ultimately driven the company pretty much into bankruptcy. So not the way I would have wanted it. But it's one of those things that sometimes it's hard for people to see the long term benefits of making a major change in a business model. But I think one of the major reasons so many companies go out of business is because they don't look at the ways that they need to change if they want to survive in the future.
- [26:32]
Jason Silver
Yep, yep. Change is tough, that's for sure.
- [26:36]
John R. Miles
So you and I have something unfortunately in common that I'm sure neither of us wish we would have cured. Earlier this summer I lost my sister to pancreatic cancer and you start your book out talking about the heartbreaking moment when you had to inform your parents that your sister Rachel had a late form of cancer. I can't even imagine what that would have been like, having to tell them, because at least in my case, my sister was with my mom when they both called me to give the news. But I think whenever it happens, My sister was 46 at the time. I think your sister was 36 or 37. It is such an unexpected phone call, especially when you see someone who appears to be in perfect health. Did you have any inclination at all that something was amiss with Rachel, or did it hit you as a complete shock?
- [27:37]
Jason Silver
A complete shock. It was very challenging. I lack the words. And that you're going through something like, this is the best thing I can say to you, is that you can come out of the tunnel stronger than the way that you went in, which is something I didn't fully grasp before. And it was a terrible, I want to say moment, but many moments in my life where we were building this company and I was the COO there, and we had raised money and we were building the team, and I had a young son. And my parents left to go on vacation. And I got a phone call from my sister who had gone to her regular doctor's appointment checkup. And the doctor said, I just, you gotta get this. You gotta go to an emergency room and get something checked out. And my sister walked to the doctor's appointment. It wasn't like she was feeling terrible. And she called me. She didn't really even want to call me. She didn't even really want me to come. She was trying to, I guess, be strong and just, it's okay. I'm working on it. And I dropped everything. I'm very grateful for my family who rallied around me to enable me to go and do that. And I got to the hospital, and the scene was not what you want. She was getting all of the best treatment, all of the top doctors, all as quickly as humanly possible. And that might sound like exactly what you want, but when that's happening, you know that you're the worst case in the room. And when you're in the worst room in the hospital, that's not a good position to be in. And it became very clear very quickly. And I sat with her as she got all the tests. And once I got the lay of the land, I had to call my parents. And it was the single hardest phone call I've ever had to make. It was a terrible experience to call my parents while they're on vacation and explain the situation and hear my mom scream like I'll never I won't forget it. And my sister fought hard and nine months later she passed away before she turned 40 changed everything.
- [29:41]
John R. Miles
Well, I mean I hate that happened to you. I hate that it happened to me. And in the case of my sister, I don't think I've ever seen anyone fight something with so much passion as she did. I mean she tried everything she could from medical options to eastern medicine options to changing her complete diet the complete way she lived her life. And I guess what we both have is the memories and long legacy that they both left us. And I am at this period where I'm still trying to process it and what I'm going to do to honor her. I know after Rachel passed you mentioned in the book that turn your life into an ongoing experiment of me search in into positive psychology which dove you into productivity, mindfulness and other wellness practices. What were some of the key lessons that you discovered through your research?
- [30:46]
Jason Silver
I'm wrong a lot. I think that one really what I what kind of happened and looking back you can write it in a book and tell a coherent story about it and it's not always as clear when you're working your way through. And what I knew was that I was going down. I was not pointed in a great direction. I wasn't coping handling it was really hard. I was falling apart. I needed to do things differently and what that gave me that I had never really had before was okay what I'm doing isn't working. I don't know exactly what's going to work so let's just try all the things and see what works. And I went full Tim Ferriss style before he was huge and I really knew what that meant and I tried everything I had preconceived notions about oh therapy is for someone who can't handle their own stuff. I was very wrong about that. Therapy was incredibly helpful for me not just when you have something in quotations wrong you don't have to have an issue. It was a great help and has been a great help for me even all these years later. Meditation is something that has been a big part of my life and it's a habit that has has stuck from the experiments I was doing I thought that was for like hippies you can't be a type A and trying to accomplish all these things and take time out to umbaya meditate super arrogant way to look at the world wasn't right And I'm glad that it. The clouds parted and I saw it from just trying all these different things. And I kept a tracker. I was reading 100 books or more a year. If anything said, this is going to make you feel better or do better. I tried it pretty much, and I kept a big track. And I was like, well, I don't know if this is going to work. Let's see what happens. And that led to a lot of things not working, some in hilarious fashion, and a small handful of things really being incredible. And the more I found these incredible things and stacked them up on top of each other, the better and better I started to feel. Eventually, it plateaued. And I talk about that in the book and how that led to writing the book, but it was really a big moment of just, let's just get rid of all the preconceived notions. Let's flip all the assumptions on their head and let's see what comes out the other end of it. And that is a mentality and an attitude that has served me incredibly well. And it's the reason why the book exists. And it's the reason why I feel as positively as I've ever felt in my life now, five years removed from my sister passing away. And I felt a lot of guilt for a lot of years thinking, how is it possible that I can be living at my best as a result of losing my sister? And over time, I realized that, you know what, not talking about that and not living in this way would be the greatest disservice I could possibly do to her life. And she. And that experience gave me a big push to just. I want to pay this forward as much as I possibly, as much as I possibly can.
- [33:36]
John R. Miles
Well, thank you for sharing that. I know it's not easy to talk about. I'm going to now take us into your book.
- [33:42]
Jason Silver
Hard Pivot. Good call.
- [33:46]
John R. Miles
So your book is divided into multiple parts. The first part of your book really gets into how to change your work week from doing what you typically do in five days into four days. And the first chapter that you go into really has an interesting twist to it because you bring up the performer Bruce Springsteen and how he almost nearly crashed your career. Can you go into the event you were trying to set up and how Springsteen interfered with that, but what you had to do to overcome that and how it changed things.
- [34:29]
Jason Silver
This is an example of, I wish I had learned this lesson when this story happened. And we'll go back to Airbnb for it. I was at Airbnb and the Team came up with this amazing idea where we were basically taking. You can look them up now, they're all over the place, called a night ad. And we were taking all these unconventional places and turning them into Airbnbs that you could win a competition to stay at. Great for marketing, really fun to do. And we were working on this one where it was going to be a sports experience. Someone was going to get to sleep over in a stadium. They were going to start by getting a whole hockey experience. They were going to be hosted by a very famous hockey player. They get to meet the team, they get to see a behind the scenes stuff, watch the game, go to sleep at night while they're sleeping in a box, which is usually for corporates to, you know, hobnob in. We had turned it into what looked like a northern Canadian cabin. They sleep in the box, they wake up in the morning. The hockey rink had been converted into a basketball court. And they have a whole experience with the NBA. The next day they get to meet the team, do a shoot around. You got to watch the game. Really fun and amazing. This obviously is something that takes a long time to push over the line. We were negotiating with the NHL, the NBA, the stadium, the teams. There's just a lot of moving parts. We're walking into the final meeting after months of negotiation where I thought all I was going to do is sign the document movements. We're done here. And in that little pre meeting that happens when you're walking into a big important meeting, someone leans over to me from their team and they say, jay, we're super excited. We've got the dates. It's going to be awesome. And I don't remember where they were. I just remember that they were separated by three days. And I thought, oh no, the whole thing's ruined. What happened here? What? What do you mean? It's a three day separation. And they're like, yeah, it's no big deal. We're going to do the hockey thing. And then Springsteen has a concert, we're going to set it up, do the concert, tear it down, and they come back and do the. Do the battle basketball thing. My first thought was, we gotta move this Springsteen concert. To which the response was, dude, he's called the Boss. You don't move his stuff, he moves your stuff. So get that idea out of your head. And as soon as I knew we weren't going to be able to move his concert, I figured we were done. These stadiums are planning things way out into the future. Things get booked 12 months out to find a hockey and basketball game back to back, let alone one where there's availability for us. I thought, like, we're cooking no chance. And all of this happened because of a very simple miscommunication. I had effectively communicated all of the various components of the activation, but I had not effectively communicated that it needed to happen on back to back nights. And that is what pretty much blew it up. And if you fast forward to years later, that's when I realized that one of the most fundamental things holding us back at work are miscommunications. They are big, gigantic problems. Right? $1.2 trillion is being wasted every year in the United States of America alone due to workplace miscommunications. That is more than the GDP of all but 16 countries on this planet. Right? Meaning that most countries don't even produce as much as the US is wasting because of workplace miscommunications. And if you do the math, because you're a nerd like I am, 1.2 trillion is a big gigantic number. I don't know what to do with this number. It's really big. What does it mean for me? Well, if you reverse calculate and do the math, $1.2 trillion works out to a full day of lost productivity every week for every single person in the America. So if you are working in a job today, there is a very good chance that you are losing a full day because of miscommunications that are happening to you throughout your week. And if you can just find a way to eliminate these miscommunications, you can do the exact same amount of work that you do in four days to accomplish five days of work. And you have a whole extra day. I'm not saying your company is going to shift to four day work weeks. You have a whole extra day to do even more work if that's how you want to spend it or to spend it on other time. And certainly you will be way, way less frustrated. Because nothing is more frustrating than I'm working with John on a project. We have a great discussion about what we need to go and do. We think we're on the same page. We go and work on it. I come back to John two weeks later, I show him what I've done, and only then do we realize, oh, shoot, Jay, there was some kind of misunderstanding that happened when we got together two weeks ago, that two weeks of work is all or mostly wasted. You got to go back to the drawing board. Like there's nothing more frustrating than that.
- [38:58]
John R. Miles
Well, in the book, you go through that there are two different types of communication, visible and invisible. Can you talk about the difference between the two and how you make the invisible visible?
- [39:10]
Jason Silver
The whole idea of the book is trying to show people a way to enjoy their jobs more and do better at them. And the whole first third of the book is about eliminating things that are in our way. And that was one of the big learnings I had when I started experimenting with work, is I thought that by adding things into my job, it would get better. What I learned is actually removing them was the biggest help. And this is where my, like, deep dive on miscommunication started happening is, wow, this miscommunication stuff is really big. It's a very massive problem. If I can get it out of the way, it's going to have a big impact. The solution is insanely simple. The problem we talked about marrying the problem, the problem that a lot of us know but fail to remember often, myself included, is two different people interpret things in two completely different ways. Okay, so a visible miscommunication. Human beings are amazing at. That's when I say something to you and you don't understand what I've said. When that happens, your head cocks to the side, your eyebrows raise up. You, you're clearly looking confused. And unless I don't care at all, I'm going to recognize that, take a moment and try to explain it in a different way until the expression leaves your face. Visible miscommunications aren't costing us a lot. It's invisible miscommunications that cost us and what an indivisible miscommunication is when we've understood each other perfectly well but interpreted the words in a different way, and they are invisible because I can't see it. There's no look on your face. It looks like you got it. The most common question people ask when they communicate someone is, did that make sense? Did you understand? Was that clear? The answer to that question can be yes, and I could have a completely different understanding than you do. So it's not about if we understood each other. It's about how we understood each other. And when you realize that the only way to effectively communicate is to understand how the other person interpreted your words, that's when you can fix this really frustrating, gigantic problem that's happening to all of us at work.
- [41:14]
John R. Miles
And I love it because it does definitely have a huge impact that I've seen in so many of the different roles that I've been in. When communication is not well understood. Even when you're not in a large organization, this can happen in the smallest of teams.
- [41:29]
Jason Silver
Oh yeah. People think, well, I know John really well. We've been working together for years. Therefore we don't miscommunicate. I say, not true. I'll give you an example of the most common one that comes up with folks. If I say to you, I want to get this, I want you to get this done for me by end of day, right? You'll say, well, I understand. End of day. I know what the word end means. I know what the word of means. I know what the word day means. End of day. Got it. But what did I mean by end of day? Did I mean 5:00? Did I mean 5:00? Your time, my time? If we're in different time zones, did I mean end of day meaning 11:59? Is it okay if you get it to me before I start my day, the next day, before 9:00? Like, what exactly does that mean? And that can have huge implications. Can you get this done for me by end of day? Sure, no problem. I'm gonna blow everything out of the way and spend the last half of my afternoon getting all of this stuff done because you needed to get it for me by end of day, which is 5pm Turns out I didn't actually need it until I get into the office tomorrow and start working on stuff, which isn't until 10am you could have not blown up your afternoon. You could have done it first thing in the morning the next day, or you could have juggled your schedule in a bit of a different way to make it happen. And that's an example where end of day is perfectly understood but very often and easily misinterpreted.
- [42:48]
John R. Miles
Absolutely. Great example. So in this next chapter, you open it up with a quote from Larry Page where he says, there are basically no companies that have good, slow decisions. There are only companies that have good, fast decisions. And I'm going to go back to an example that I had in my book that represents this. When I was a young lad and I was a naval officer at the time, I worked on this Admiral task force where we were doing counter drug interdictions. And my first boss, I was so scared before I got there to actually take this job. And when you're in the service, it's not as if sometimes you get to pick where you're going, sometimes they pick for you. And that's what happened in this case. And getting ready to go to this new command, I mean, the great part Was it was in Key West, Florida. The bad part was, was the guy I was going to work for, his nickname was Fitz Hitler.
- [43:46]
Jason Silver
Oh boy.
- [43:46]
John R. Miles
And so I am like, what the heck am I walking into? And Bill turned out to be one of the best bosses I have ever served with because he was at times extremely challenging. But those times were always on a one to one basis. And he never under cut in public. In fact, I could say something 180 degrees incorrect and he would have my back, even if it was up to the admiral.
- [44:17]
Jason Silver
That's great.
- [44:17]
John R. Miles
But what I. But what I loved about him the most was that when an issue came in and when I was there, we had a major potential huge international incident because we were responsible in this command for what was going on in Cuba as well. And while I was there, a couple civilian aircraft got shot down by the Cubans. And Bill made a very quick decision, happened to be the right one on how to handle it. And he was absolutely the type of person that you would want in the foxhole. The person who took over from him had this outstanding reputation as a great guy, big family person, but he was one of these people who needed to get the input of 100 people before he would make any decisions. And so oftentimes when we were in the fast paced world of drug interdiction, by the time he would come around to making a decision, we had already lost the slot to do the interdiction or to make a difference. And really what I learned from this was that sometimes you just have to make a decision based on the information that you have. And oftentimes, as Larry Page was indicating, if you take so much time to make decisions, sometimes the moment passed you by to actually implement them and make a difference. Using that as a background, how can having too many cooks in the kitchen be a negative thing for companies?
- [45:54]
Jason Silver
I think when you take too long, I don't think you make decisions. Decisions make you basically and they get taken out of your hands because you might have three or four or five different options and you spend so much time deliberating them that by the time you get to making the actual decision, there's actually only one thing you can go and do that's not you making a decision, that's you getting backed into it. And if you do want to be intentional, you need to be decisive. And I work with a lot of companies now, so. So now what I do is I advise executive teams and help them build their companies. And one of the most common challenges I see is decision making velocity. It's very slow, which is very bad for the business and super duper frustrating for people. Right? There's nothing worse than knowing what you think you need to go and do. And you're waiting for it to go up the flagpole to this boss and that person and this team, and then here. And you're like, I could have just gotten the job done, you know, so much faster. We could have just made the decision already. And so having trouble making quick decisions is hard. And I think there's actually a myth that if you have too many people, you can't make quick decisions. And I think that's wrong. And I've seen it be wrong time and again. And I wrote what I wrote in the chapter because I really wanted to break the myth that too many people doesn't mean slow decisions. Bad decision making means slow decisions. You can have 50, 60, 70 people involved in a decision, and it can be very fast. I tell a story in the book about 1960s NASA. 1960s NASA obviously was trying to put people on a moon. In the. On the moon, they didn't have a very long time to do it. They had a massive budget. It was like hundreds of billions of dollars. 400,000 people were working at this, the company at the time on this particular project. The objectives were big, very challenging, on and on. All of the situations you think would lead to not great, not fast decision making. Their average decision time was a single day. Right. If they could have done this in 1960s NASA without slack and chat and email and cell phones and all this stuff, like, how is that possible when people's lives are on the line? Technology didn't even exist to make it happen. If they can do it, anyone can do it. I point to that example all the time. People tell me our decisions are too complicated. Well, is it more complicated than having a rocket with, you know, more than a million moving parts and sending people to the moon and back, they're like, no. Well, there are too many people involved. The budgets are too big, the risks are too large. Are we going to kill people? No. Okay, so it's possible. Let's figure it out. And as I started trying to figure out what is the reason for slow decision making here? How do we speed it up? What is getting in our way? I realized that we're actually building teams in a very positive way. But because we haven't changed the way we think about these teams, we wind up in these challenging situations, particularly as it relates to zip decision making. And that's all about diversity. And I am not going to make the case that diversity isn't amazing. It absolutely is. And if you don't believe that, you can go and read pretty much every study out there. And when I say diversity, what I mean is diversity of thought. Okay, so we want to have as much diverse thinking around a decision as possible. I'm not interested in people who will tell me the decision that I would have made on my own. I'm interested for someone to come in and tell me a decision that I would never have thought of, or to share context or thinking or an approach to this problem that isn't one I would have thought about that's going to make our decision better. Okay, but the more people we get and the more we build our teams for diversity, the more disagreement is necessarily going to come out the other end. And it's this disagreement that's the problem. It shouldn't be, but it is. The way that we're wired up is we're wired up to agree with one another. So in order for me to make a decision that I feel most comfortable with, I have to get everybody to agree. And my argument is this agreement is killing us. This is what's slowing it down. I do not have to agree, nor do I have to get everybody to agree with every decision that's made. Great teams who make fast decisions have learned that we don't need agreement, we need alignment. And this might sound like a nuance, but it is incredibly important. And so the key lesson here is the better you disagree, the faster you decide.
- [50:08]
John R. Miles
Just last night, interestingly enough, I was watching this Netflix special on profiling the Apollo program. And one of the things I learned from this was that even though they had this mass of people that you're talking about, the actual Apollo astronauts themselves were intricately involved in developing the rocket that they were going to be a part of. And so they ended up breaking down almost every single aspect of this into the most minute of points that they could. And each astronaut was then appointed to tackle that specific problem that they were trying to come to find a solution for to get this thing built. And so perhaps one of the reasons that they were able to do the fast paced decision that they were with that many people was because of how they parsed the ownership of the whole program down to these micro components, which is an interesting way to think about something that large and how they were able to accomplish it.
- [51:18]
Jason Silver
This is why I picked them to put in the book. It is a masterclass in complex and yet very fast decision making. And the reason why the topic I think is so important is he called it out. This particular chapter is in the first third of my book. It's just like the first chapter the average company is wasting for each person inside of it is wasting a full day every single week because of slow decision making, not time spent on decision making. Right. There was this amazing study that was done where they polled managers and they said, how's your decision making going effectively? And managers, there were 1200 of them, managers self reported that they were wasting 50% of the time that they were spending on decision making. Right? Wasting unnecessary, wasted time. And you see that. And then people think, well, I knew my manager sucked at decision making. Who do you think they're wasting that time with? It's you, right? And so we need to get better and faster at it. And by unpacking the NASA example and working on some of this stuff with the clients that I work on, what I realized is if you want one tactic, and I love people to take away tactics, this is what the book is all about. If you can talk or type, you could try every tactic in my book. And here's one you can go and try. Stop listening to the podcast when it's over, go try it at work. Right? The single fastest way to speed up decisions, decide who's going to decide. It's so simple, it's very hard to remember to do this. This is what NASA did incredibly well in that story. Decide who's going to decide. So the way most decisions go is John and I get in a room and we immediately start debating the decision. Right? What is it that we want to do? Do we want to turn left or do we want to turn right? You start arguing the merits of left, I argue the merits of right. We're having a strong, vigorous debate. That's fun. Great. We miss the most critical step. Who is actually going to make this decision? In the absence of knowing who's going to decide, you can't disagree because I will continually be trying to convince you that I'm right and you will continually be trying to convince me that you're right. And by the way, that's great. We want to be doing that because we want to hear each other's perspectives. But we need a way to collapse the discussion, the debate into a decision. And that requires a decision maker. So you might choose. We're going to take a vote, right? We have an odd number of people, or we're going to assign an odd number of people and we're going to argue as much as we possibly want until we hit the date for the vote. And on that moment we're going to take a vote and then everyone's going to get a line behind it. That's how we're going to decide. Fine. Other option is we're going to pick one of us. John and I are going to argue about which way we're going to turn. It's John's decision. Super duper. Right. And John lets me know, okay, I've heard what I need to hear. I'm going to make the decision now. But the most fundamental mistake that I see teams making is they dive right into the debate before they decided who's going to decide. So the most helpful thing you can do, whether you're the CEO or an intern, doesn't matter. The moment you hear that we're starting to debate a decision, take a half a second, raise your hand or do whatever you do in your meetings to jump in. Hey, everybody, just want to quickly clarify who's going to make this decision. Whose decision is this? And usually what happens in that situation is it feels like it gets way worse because we don't realize who it is. Or multiple people put up their hands that it's their decision. And this five minute debate, the five minute discussion around who's ultimately going to make this decision is incredibly helpful. Oftentimes I advise people to do this and the decision maker's not even in the room. Right. What are we going to accomplish without them being here? So just taking a quick second, it seems like it's magic. It seems like it's not going to work. I promise it will. Just try it out the next time you're in a meeting. You hear a decision coming up. Hey, just want to quickly clarify who's making this decision. That is beneficial information for the entire room. Worst case scenario. It was incredibly clear, hey, this is John's decision. And now everybody in the room has again been realigned that it's John's decision. It takes five seconds. But more often than not, we won't be sure we'll clarify the decision maker and that by itself is going to shave off a huge amount of the wasted decision making time that you're spending today. Just knowing who's going to decide is going to make such a big impact for you.
- [55:30]
John R. Miles
Yeah, I think that's a great point. I wanted to spend some time in the second section of your book. Your chapter four and my chapter four in my book are actually covering the same thing in very different ways. So my chapter's name is that is A mindset shift that you need to become a fear confronter, which is really working through your self doubt. Your chapter four is focused on how you use that self doubt or imposter syndrome as a superpower and how to tap into it. Can you talk about why you decided to approach it in that way?
- [56:07]
Jason Silver
I was really hoping you were going to bring this one up because I was reading a chapter and I was thinking about it and I think for me it's really this thing that the more folks that I work with, the more I Imposter syndrome is everywhere. Right. And I've struggled with it too. I was mentioned to you before we hopped in here. I've written this book. I'm very excited for it to come out. I don't feel like an author. I don't think I can swing with authors that are out there. And yet I aspire to. And you just. We all feel imposter syndrome. And as I was pulling the pieces apart and thinking like, what have I learned and how have I learned this idea of I want to help people enjoy their jobs more without changing their jobs. And one of the big things that's preventing us from enjoying our jobs is like the anxiety and self doubt that we fear around it. And I think a lot of the conventional terminology is not super helping. We'll start with the title itself. It's called Imposter Syndrome. Okay. Syndrome. Now the challenge I have with this is 80% of people agree that they feel imposter syndrome at work. 80%. So if you feel it, I feel it. We can't all be imposters. And like on top of that, in this day and age, I struggle to think about anything that I could get 80% of people to agree with. Okay, so if we're going to call imposter syndrome a syndrome, we really should be calling it like human syndrome. It's just like an outcome of being human. Like it's ridiculous. We wouldn't call it that. And so then we think, okay, well we all feel this thing and what are we trying to do about it? And conventional wisdom says things like, well, believe in yourself. Right. It's a light switch. Okay. And I liked in your chapter you talked about like, here are some ways to help you push through. And I'm not saying that there is not a place for that. It certainly is impactful and important. I just think that there's a missing part of the conversation here to add on top of that self belief, for me at least, is not a life a light switch that I can Just flip on and off. I'm not just, ah, I'm going to go do this thing and I'm going to bomb because I don't belong. Oh, just believe in myself and it all goes great. That's just not the way that my brain works and it's not the way that I've seen folks around me working towards it. And as I started to dive into the research, I started to see not only do I believe that you cannot turn it off, I don't think you should. Okay, so I think imposter syndrome has the potential to have an incredible superpower effect for you. The reason why I believe this is a bunch of really cool research. One of the most interesting ones I found was at the MIT Sloan School of Management. What they did is they took two groups of doctors and they put them through training where they were effectively going with trained actors who are presenting all sorts of different potential medical cases. And they have to try to diagnose them as they go through. Right. And as part of them coming through the training, they gave them some kind of a questionnaire or something to do, like a psych profile on them. But they didn't know that they were being psych profiled. And they put them into two groups, people that felt imposter syndrome and people that didn't. So let's call them the imposters and the confident folks. We put those two doctors in. I know you've read the book, right? So you know the outcome here. But the imposter group performed better than the confident group. Okay, so there's something about imposter syndrome there that's helping them. And it's the specific way that imposter syndrome is helping that I got really interested in. So what they found is in terms of their diagnostic capabilities, right? The actual job that they were there to perform, they were equivalent. So despite the fact that one group felt self doubt and the other group felt very self confident, they were equally as good at identifying whatever the issue that the patient was presenting. Where the impostors quotations perform way better is when the patients took exit surveys, they over and over again ranked the doctors better that came from the imposter group and they had no idea which group their doctor was in. And the reason why becomes obvious. When you see research like this and you take time to go through it, when you feel imposter syndrome, it makes you feel like you don't belong. I'm not good enough. I can't cut it with this group of people. What it also does for us when that happens is it makes us more other focused. We think about other people more. The more you think about other people, the more empathetic you're being, the more you show them that you care, and the more they're actually going to feel like you're doing a great job for them. And so actually, the experience and feelings of imposter syndrome are triggering something in us that make us a much better teammate. And I don't think it's something that we just want to turn off. Right. So the question is, what do we do instead? We could definitely dive into that if you want, so folks can have a bit of a tactic. Is that a good direction to go?
- [60:40]
John R. Miles
Yeah, let's do that. I always love to give people takeaways, so that would be perfect.
- [60:45]
Jason Silver
Okay, so the question is, like, what do you do instead? And to really think about that, you have to unpack, like what imposter syndrome means. And it's basically a feeling that you, like you don't belong. You're trying to build more belonging. You're in a group of people and you think, wow, these folks are really smart. Way smarter than me. I'm not smart enough to be here. Or in my case, let me look at a bunch of authors. Like, I'm not a good enough author to fit into that group, whatever it might be. You're feeling like you don't belong there. What is the absolute best way to build belonging? Again, you can turn to research here, which is really helpful. It's a thing that we've known for a long time. It's been 80 years or so, or maybe more, since how to Win Friends and Influence People came out. And that book talks about this particular tactic a lot. I think we just sometimes forget it. It's asking questions. When I ask John a question in a conversation, he is more likely to like me because I'm showing a genuine interest in him and I'm trying to learn about him, and I'm not just talking about myself, which people don't like as much. So questions are the, like, antidote to imposter syndrome, if you want to think about it as a symptom. Okay, but there are some caveats here. Luckily, there were some folks that went and did a bunch of research that I would never want to do. They wanted to figure out what is the. What are the best questions in the right scenarios. And I'm very grateful that Harvard put a team together and they were like, let's go and study this thing. They asked people all sorts of questions in all Sorts of different situations. My favorite slash, least favorite because I was thinking about what it would feel like to be the researcher asking people these questions was they actually asked people like while an adult, have you ever felt sexual desire for a minor? Super awkward, right. And the person on the other side of the conversation didn't know what was going on, they just thought they're being interviewed. And then at the end they would rank all sorts of different things, likability, things like that. Right. So deeply uncomfortable questions in all sorts of different settings. They asked some that weren't as deeply uncomfortable as that. But what they found is actually people like you more when you ask them questions in a one on one setting. They don't like you more when you ask questions in a group setting. And when you think about how to apply this to work, what I realize is, well, most of our interaction, especially when we're feeling imposter syndrome, is usually in a group setting, right. We're sitting in a meeting. And when I'm sitting in a meeting, if I ask John a lot of questions, John is going to like me better. But everybody else who's watching the interaction is actually going to prefer John because John's providing the answers. And so you want to find the right way to ask questions. And the best way to do that is in a one on one setting. That's where it's going to build the most, the most kind of trust, belonging, likability, whatever it might be. And so what I recommend for folks is when you're feeling imposter syndrome, don't try to switch it off. Recognize that it's doing something beneficial for you, which is it's helping you be more other focused. You're going to be thinking about your colleagues, which is going to help you make a better, become a better teammate with them and have more feeling of belonging. And then number two, go and deploy the tactic to help you build more belonging, which is find somebody in the room, whoever it might be, and find a way to go get one on one time with them. Maybe it's like over lunch, maybe it's in a one on one meeting that you schedule, maybe you're going to grab coffee, whatever it might be. This works because number one, it builds a greater sense of belonging. And two, if you ask them the right questions, you will get a lot of information which will help close whatever knowledge or skills gap you might actually have in place, which is also going to help with this feeling of quote unquote imposter syndrome. So feel imposter syndrome. Let it Be a trigger for this is okay, everybody feels this. It's going to make me more other focused. That's great. The in quotation solution here is who's the right person for me to book a one on one with? Let me get them and ask them a bunch of really good questions in a one on one session. That's going to help me build that sense of belonging and it's going to help me close the knowledge gap one on one questions.
- [64:35]
John R. Miles
So one on one questions are the key. Thank you for that pointer for everyone. I think it's a great one and you're absolutely right. The questions that we ask do help form that tighter bond. So keep that in mind.
- [64:49]
Jason Silver
A lot of times people will ask me, well, that's great. I don't know how to ask great questions. I think everybody does. The other thing that the Harvard study showed was the best one on one questions are follow up one on one questions. And I think that's great. I'm happy the science worked out that way because follow up questions are the easiest. Right? You don't have to come up with some amazing thought provoking question questions like help me understand whatever that thing is John just said or what do you think about some idea I've had Or what did we not discuss that you think we should have? Which is a great question. But these follow up questions work great because they show the other person that you're really listening to them. I can't ask you a follow up question if I wasn't listening to you, so you might think you have to come up with some beautifully eloquent question. Find the person, get them in a one on one, listen to them, ask them a follow up question.
- [65:38]
John R. Miles
Awesome. Well, Jay, the last thing I wanted to discuss with you was something that ties us back to the original story of your sister and finding a way to pay this forward. And the topic here is you're never going to enjoy your job if you're not experiencing joy in what you're doing. And in the chapter I'm talking about, chapter eight, you express it this way, the more you enjoy, the better you do. Can you talk about this through your story of meeting Jordan Banks and maybe who he is and why this encounter with him was such a powerful moment for you to understand the importance of joy and how you were crafting your career.
- [66:28]
Jason Silver
Jordan probably fits into one of those examples that you asked earlier of what's a small thing somebody did for you that had a really big impact. And at the time I think I was at Airbnb at the time, I think I can't remember exactly when it happened many years ago. And I was introduced to Jordan and Jordan is a relatively big name in tech. He at the time he was running Facebook in Canada and doing all sorts of stuff with Facebook. He was early on at ebay. He's the kind of person where when I looked at his career, I saw the boxes that he had checked along the way and I was thinking to myself, great, how do I do that? But faster is what was going through my head. And I got an opportunity to have a meeting with the guy and I came in ready with all of these questions that were essentially, how do I figure out how to do what you did faster? And I'm super glad that he derailed the whole conversation because they were like derivative. It wasn't a bunch of interesting questions. I don't know what it is. I would learned from him, honestly, in that. And he asked me, what do you want to do? And I told him, I want to build a billion dollar business. And usually when I told people that it's a big, audacious goal, usually people would push back and say effectively, like, you can't do that. Building a billion dollar business is really hard. What makes you think you can do it? They'd be pushing in that way. Jordan had the completely different push, why do you want to do that? How are you going to feel while doing that? And it like knocked me back in the chair a little bit. And I was just like, well, what do you mean? I sputtered through the rest of the meeting. I don't know why he ever took another meeting with me. And he did, which I'm very grateful for to this day. But my answer was some version of, well, obviously I would want to build a billion dollar business. Like, why wouldn't you want to do that? And the lesson he was trying to teach me, thankfully it did bang into my head over time, was how it feels while you're working towards your goals is equally as, if not more important than the goals themselves. If you don't enjoy the process of getting there, if you're not going to enjoy what it's going to feel like once you've accomplished those goals, what's the point in them? You know, why? What is it about a billion dollar business that you're interested in? How do you want to feel? How do you want to experience it as you're working your way through? And he gave me an exercise that was very helpful for me and I've since kind of shifted it around this idea of enjoying so I can show people, like, the power and impact that they can get if they're really enjoying what they're doing day to day.
- [68:55]
John R. Miles
Well, I love the story. I've been on both sides of that, where I've had almost the same exact discussion with a mentor on me wanting to climb up the ladder and him almost having the same discussion. And I've had the same discussion with a number of founders and entrepreneurs that I've tried to coach who want all the success but don't necessarily understand what comes with it and what it's going to do to their personal lives.
- [69:22]
Jason Silver
I can give folks an exercise that's great, and there's just a lot of interesting research out there that shows that if you enjoy your job more, you're going to do better at it. So you're more likely to accomplish these goals that you have. But most folks are not enjoying their job as much as they could be, potentially even at all. And I think that's where a lot of the book came from is as a Type A, I want to accomplish stuff, whatever it might be. It's like enjoyment comes later. That's always how I thought about it and trying to work that into the conversation now. So it's actually, if you do some intentional things here that are in your control to enjoy your job more, it's going to make you way, way more impactful. So there are exercises in the book. We could talk about them now, I'm not sure how we're doing on time, but I'll let you steer the.
- [70:06]
John R. Miles
Well, I'm going to let the listener buy the book to get their exercises.
- [70:10]
Jason Silver
I would love to buy the book.
- [70:12]
John R. Miles
And I'm going to ask you a final question, and that is, how do you hope readers of this book will be impacted?
- [70:21]
Jason Silver
I want people to feel like they're. I want people to feel like they're good. Like, I want to say to people like, you are good. And I don't mean that in the sense of, like, John, you're good at what you do. What I mean is that you have a lot more agency than I think you might think you do to change the situation that you're in. And often I find that a lot of the rhetoric out there and a lot of the playbooks that are out there are really about changing our environments, getting into a new team or a new project or a new company entirely. And what I find happens in those situations is we change jobs or we change work, and because we aren't changing the way that we work. A lot of the bad juju just comes back later, right? Miscommunications. If they're continually happening to us and they're happening us at our job, go get a new job. It's going to keep happening there. And so rather than assuming that you have to change your environment, there are some things you can do to think about changing yourself, changing your approach to work. And I really want people to feel like, listen, you have more agency than you think you do. You can change the way that you're working and have a bigger impact on your day to day. You can enjoy the job. You already have a lot more than you think you can. You can do better at the job that you already have, a lot more than you might be today. And it doesn't take some big, massive professional development. I have to go and become an expert at XYZ to go and make that happen. That's what I really want people to take away from. The book is like, it covers nine of the most common workplace challenges, a very disarmingly simple tactic that pretty much anyone can try. And I feel really good that if someone picks up the book, you try all nine. Worst case scenario, a small handful of them are going to have a big impact and you're going to see just how much agency you have. It just takes flipping the paradigm on its head a little bit. So I'd like people to feel like, man, I have so much more control than I thought I did over my job, my experience and my job and my performance in my job.
- [72:18]
John R. Miles
Well, Jay, thank you so much for that and thanks for this conversation and for this great work that you're putting into the world. If people want to know more about you, where's the best place for them to go?
- [72:27]
Jason Silver
Best place to go is YourGrassisGreener.com that's the website for the book. Would love folks to pick up the book. There are links there to do that. They can get in touch with me through the webpage there as well. Always would welcome feedback, always welcome hearing how people are doing. But would love folks to head over to YourGrassesGreener.com, click on through, pick up the book and help me learn that I maybe can be an author and give me whatever feedback you have. Would love to hear it. Well, Jay, thank you, thank you and thanks, thank you to everybody who made it to the end here with us too.
- [73:00]
John R. Miles
Wow, what an inspiring and thought provoking conversation that was with Jason Silver. His insights on transforming the work that you're already doing and leveraging the skills you already have are incredibly relevant for anyone seeking to create a fulfilling career without waiting for the perfect opportunity. One of the biggest takeaways from today's episode is the power of reframing your mindset to see opportunity in what's right in front of you. By being more intentional with our work and learning to navigate challenges, we can find purpose and joy right where we are. As you reflect on today's episode, consider one specific strategy you can implement in your life. Whether it's increasing your productivity, balancing work and personal goals, or aligning your daily actions with greater purpose, Jason's insights provide a roadmap for making each day count. If you enjoyed today's episode, please take a moment to leave a five star rating and review. Your feedback allows us to keep bringing you impactful conversations and helps others find the show. And if you know someone who could benefit from Jason's message, sharing this episode with them is the greatest compliment you can give us. For those interested in taking these lessons even further, I invite you to consider bringing me in for a speaking engagement tailored to your organization or event. My keynotes are designed to ignite, change, drive growth, and create intentional impact in teams and individuals alike. Learn more about how we can collaborate@johnrmiles.com speaking remember, you can find links to everything we discussed in today's show@passionstruck.com and if you'd like to watch our conversation, head over to our YouTube channels, John R. Miles and Passionstruck Clips. Don't forget to check out our sponsors and deals@passionstruck.com deals to support those who support the show. Be sure to follow me on social media to stay connected and up to date on future episodes. Just search for John R. Miles on your favorite platforms. Next up on Passion Struck, I'll be joined by Bo Eason, former NFL player turned acclaimed speaker and author whose insights on personal greatness and storytelling will inspire you to think differently about what it takes to excel in any field. BO brings a powerful message on resilience, dedication and the relentless pursuit of excellence. You won't want to miss it.
- [74:58]
Jason Silver
Usually your best story is the one you don't want to tell. Isn't that funny to say, like, there's a lot of stories that we want to tell, right? Like about, oh, I won the championship. Look at my trophy. I'm sure Tom Brady loves telling that story. Look, I won seven Super Bowls. I want to know the lowest moment Tom Brady's ever had, because that's the one that has the most connective tissue to it.
- [75:33]
John R. Miles
Thank you as always for your time and attention. Remember, the fee for the show is simple. If you found value in today's episode, share it with someone who could benefit. And as always, do your best to apply what you learn here so that you can live what you listen. Until next time, live life. Passion Struck the holidays are here at the Home Depot, so let's get to decorating. Find your perfect tree in our huge assortment of shapes, sizes and styles. Like the easy to assemble Jackson Noble fir with pre lit branches perfect for styling with all your favorite ornaments. Or the Flock Starry Light Frasier fir with over 1900 pre lit memory wire branches that keep their shape so it's ready right out of the box. Find the perfect tree now at the Home Depot.
- [76:30]
Jason Silver
Imagine what's possible when learning doesn't get in the way of life at Capella University. Our Flex Path learning format lets you learn on your own schedule. A different future is closer than you think with Capella University. Learn more at Capella. Eduardo.