Simple Steps to Start Enjoying Work Now with Guest Expert Jason Silver Smith

Ep: 265

Are you feeling stuck in your career? Does it seem like finding real fulfillment requires a massive change?

It can be easy to think that change has to mean overhauling your entire career, when in fact, there are small shifts we can make to unlock progress that leads to more career satisfaction, helping you identify what’s really holding you back from happiness and recognizing your true potential.

Today on The Bridge to Fulfillment Ⓡ, Blake welcomes Jason Silver Smith, author of the book, Your Grass is Greener. He’s an entrepreneur who got his start at Airbnb, and today he helps leaders build great, lasting companies that people actually enjoy working for. He’s a sought-after public speaker, instructor, and advisor on how to transform work into one of the biggest drivers of positivity in your life.

In this episode, Jason shares how the unexpected loss of his sister led to a transformation in how he wanted to live and work. You’ll learn practical tactics that can eliminate miscommunication in the workplace for good. You’ll also learn how aligning work with personal strengths helps unlock career potential, increase workplace productivity, and lead to more workplace happiness.

What You’ll Learn:

  • How a life-altering experience shifted his perspective (8:57)
  • Experiencing post-traumatic growth (14:06)
  • Tactics to find more joy in the work you do (18:41)
  • Recognizing your agency in life and work (29:38)
  • Why real change is about the small steps we take (39:34)

 Favorite Quotes:

  1. “The hardest moments of our life often become incredible blessings that we didn’t see in other ways.” –Blake
  2. “There is no job, no career, ever worth your health or ever worth your life.” –Blake
  3. “When things are going really well at work, it spills over into the rest of your life. You have more energy. You’re fired up for what’s happening in life. And the better you feel in life, the better you do at your job. And up and up and up and up and up we go.” –Jason Silver Smith
  4. “If you don’t know what you’re great at, it’s hard to know how to deploy that in a workplace setting. And when you’re not doing what you’re great at, you’re not doing the best work, and you’re not enjoying it.” –Jason Silver Smith
  5. “When we accomplish something incredible in our lives, it’s usually not some massive shift that happened overnight. It’s usually the culmination of a bunch of small steps we took over time.” –Jason Silver Smith

 

Additional Resources:

Connect with Jason:

Book: http://www.yourgrassisgreener.com
Business: http://www.thejasonsilver.com
Better Work Newsletter: http://www.thejasonsilver.com/newsletter
Linkedin: https://www.linkedin.com/in/silverjay/


Get clarity on where you are on your journey to career fulfillment, where you’re headed, optional paths to get there, and the right next step to take.

Start your complimentary, Personalized Career Fulfillment Plan by going to www.thebridgetofulfillment.com/pcfp

Transcript

Jason Silver 0:00
A lot of the rhetoric that is out there, I think, doesn’t help people, because it feels like what’s required to make it feel better, or for you to do better, is some massive shift. Meanwhile, we all know that when we accomplish something incredible in our lives, it’s usually not like some massive shift happened overnight. It’s usually the culmination of a whole bunch of small steps that we took over time.

Blake Schofield 0:28
Hi, I’m Blake Schofield, founder and CEO of The Bridge to Fulfillment. Mom to three, USA Today top 10 professional coach, and former corporate executive who got tired of sacrificing my life for a comfortable paycheck. My mission is to expand perspectives to achieve greater impact at home and work without sacrifice. This is The Bridge to Fulfillment. On today’s episode of The Bridge to Fulfillment, I’m talking to guest expert Jason Silver. He’s a multi-time founder of kids and a multi-time founder of companies. He gets his biggest thrill helping modern employees and their teams unlock a better way to work. Surfing is a close second. He was an early employee at Airbnb and helped build an AI company from the ground up, back before AI was the cool thing to do. Today, he advises a startup portfolio valued in the billions on how to build great, lasting companies that people actually enjoy working for. He’s a sought-after public speaker, instructor, and advisor on how to transform work into one of the biggest drivers of positivity for your life. When he’s not busy helping people solve their hardest workplace challenges, Jason’s kids are busy reminding him just how much of a work in progress he still is, too. I loved my time with Jason. I think he brings really tactical, simple, easy strategies you could bring to work today to bring more fulfillment, more happiness, and more ease in your work. We had some really touching conversations about his own personal journey that led him to really shift how he thought about and was living in work. And one of the things I felt was really powerful was his discussion around how do you want to feel at work. It really echoes so much of the work that I do in helping people understand the power that we each have to truly create the type of career and life that we want. And so, with that said, I’m so excited to welcome Jason to the podcast and introduce him to you. Welcome, Jason, to The Bridge to Fulfillment. I’m so happy to have you today.

Jason Silver 2:41
Very happy to be here. Thank you, Blake.

Blake Schofield 2:44
So, as is typical, I always like to start with learning a little bit about you. What can you share with me and the audience about your background and sort of how you ended up on the path that you are on, and what you’re going to share today?

Jason Silver 2:58
It always feels like one of these questions, like, when I explain it, it sounds so well structured and thought through. And it was like anything, anything but that. But yeah, the high level is I did engineering in school. You know, engineer by training. Thought I was going to be very technical. Did a master’s in engineering. Got a job as an engineer, was working a great job. Did my first real entrepreneurial thing, and I was like, Ooh, I want to do business. I was very interested in not just the problem-solving, like, technically, but how do you build a great team? How do you turn a concept into, you know, a successful business? And I didn’t want to go back to school. I had done a lot of that. Got very fortunate, found a startup not too far from me. Said, “Hey, nothing on paper says I can do business. How about I come here and let’s see what happens?” Very, very fortunate. It worked out great. I learned a bunch. Got to see what it was like to, you know, raise money, do partnership deals. I got the “Okay, Jay, sit here. Don’t talk, but take notes, and you can, like, get all the exposure you want,” which was awesome. Founded a couple of my own companies, crashed one of them, wound up at Airbnb in the relatively early days there. So I got to see what the big up and to the right feels like. After that, I was building an AI company back before AI was, like, the coolest thing on the planet to do, which was a really interesting, exciting time to be involved in it, and then hit kind of a challenging moment in my life that had me rethink it all, kind of question all the assumptions about how I was living, and shifted my focus to really helping people work better. You know, how can you enjoy your job more, and how does that lead to more performance? And yada yada yada, wrote a book, and now I’m talking to you. There’s the arc.

Blake Schofield 4:35
It sounds like you had a lot of growth, a lot of change, a lot of momentum in your career. I worked in a startup fairly long in its startup phase, Stitch Fix, before it IPO’d, and I helped launch their plus-size business from scratch, and then IPO’ing not that much after. And so, I know the level of resilience, adaptability, uncertainty, constant movement that happens in startups, and the degree of devotion sometimes that can take. And so I’m interested to hear a little bit more about what happened in your career that was that big trigger or big change moment that caused you to say, “Whoa, what I’m doing isn’t really what I want to do going forward,” because I believe that we all have those moments, and how you choose to handle those moments has a massive impact on your personal health, happiness, success, balance—all of those things. What was that moment? What were you experiencing that caused you to say, “Wait a second, this isn’t working anymore”?

Jason Silver 5:38
It was experience, kind of in my life overall, and unfortunately, it is not a joyous experience. You know, I was building this AI company, very much your traditional type A, just, like, hard-charging as hard as I possibly can. Had a young kid, and one day, my parents went away on vacation, and I got a phone call from my sister. My sister was in the hospital, and she had gone for, like, a regular checkup to her doctor, and her doctor said, “You gotta go to the emergency room and get something looked at very quickly.” And she was calling me because my parents were away, and she wasn’t, you know, sure what to do. And I went down to the hospital, and it was not a good scene. They were obviously very concerned. She was getting every scan very quickly. All the doctors were around her and paying attention to her, and we found out relatively quickly she had a very late-stage, very aggressive form of cancer. And that was probably the worst moment in my life. And the second worst moment in my life was having to call my parents, who, like I said, were away on vacation, and tell them, “I’m here with Rachel. It’s not looking good. You gotta get on a plane and get home.” And it was not stuff that you forget. Nine months later, my sister passed away before she turned 40, and, you know, it’s one of these things where if you don’t question what’s going on in your life and how you’re living your life when something like that happens, you know… I don’t know. But it was, it was a big, hard shove. It was something I never thought I would experience. You know, it’s my older sister, and watching her go through that, and then coming out of the other end, as it does, changed me in a very material way.

Blake Schofield 7:14
Yeah, I’m so sorry to hear that. Thank you for just being honest and sharing that experience. I know that you’re not alone in that. And, you know, what I often see is the hardest moments of our life often become incredible blessings that we didn’t see in other ways. For you, in that experience, was it just a recognition for you of, like, “Man, I put so much drive and energy in my career, and I need better balance,” or were there things that you looked at that you wish that you could have maybe changed for your sister, that you felt like would have created a different outcome?

Jason Silver 7:47
Kind of both, I guess. You know, I think the first thing with my sister was that it was probably the first real experience I had in my life with my sister being ill that I was powerless to do anything about. You know, there was no amount of solution. And you mentioned startup resilience. It’s like when you’re in that kind of a space, see problem, smash problem, move on to the next problem. There was no amount of talking to doctors, finding doctors, finding this treatment, that treatment. There was nothing to do there other than, like, shifting my mentality, which was very hard for me, to one of, like, how do I make this experience as good as it can possibly be for myself, my sister, and everyone around. It was very, very hard to feel that powerless. And, you know, that was challenging. But I’m grateful that I had the recognition somehow in the moment, and, you know, good conversations with my sister and prioritized the time as we were going through it. And, you know, I can look back at that time and say, I don’t have regrets. It was out of my hands, you know.

And I think what it did for me, though, is it helped me realize I don’t regret the way that I was living my life. I think it flipped the way I was thinking about it on its head, where I had always said that family was the most important thing for me, and I think what that meant was—and I’ve described it this way tons of times in the past—was if I’m in a meeting and I get a phone call from the doctor’s office because my kid was there and they need to talk about a thing, I will drop the meeting and deal with the doctor without question. However, I’m pouring 125% of myself into my work, and that’s kind of hurting the way I’m showing up for everybody around me in the present. But the justification for it that I always had was, “I’m doing this for my family.” I didn’t feel like I was doing it for ego. It wasn’t because I wanted to be big and rich and famous. It was like it’s going to create some future imagined situation where it’s all going to be great, and we’re all going to be really happy.

And I had this very visceral experience that was, first of all, you may not get there. I had a very, very close and real experience with death that just showed me best-laid plans—you can’t know. And the second same thing was, well, who knows what it’s going to be like when you get there, if you’re not living how you want to, and you’re not showing up how you want to on the way there. Is it really worth it? And so I think that didn’t change my prioritization, but it changed the way I was living my priorities day to day.

Blake Schofield 10:17
That’s so good. What you speak about, one of my mentors often talks about espoused values. These are the things I say I value, right? My values in action and are in alignment. And I think that can be one of the hardest things for us to really look at as a mirror. I say my family is first, but I’m constantly working all of the time, so much so that I, you know, I’m rushing around to make it to my kids’ things, or, you know, don’t have the time to have the real quality time on the weekends or at night or whatever with my kids. Then is there a huge disparity between me saying this is my value and how I’m actually showing up in the world?

For me, that was part of what I experienced in my corporate life was that big shift of, you know, really family and my kids being the highest priority, but often my, you know, fear survival base—this is what it takes to survive and be successful in work and in my career—would end up driving my actions that were very different than how I actually wanted to be. And I think that that is a really common thing that happens, especially for Type A, especially for high achievers. And I think often what we don’t realize is what you’re talking about, which is, what time do you really have? And from a health perspective, what’s happening as you’re experiencing what you’re experiencing?

You know, it’s interesting. I had an experience a number of years ago, actually 2010. I had left a company I had been working seven years, 70 hours a week. I knew inherently, if I didn’t leave that company, I was gonna have a heart attack before I was 50. I just could tell the level of stress was so high. And I’d moved to another company and was really happy. And I had a friend that was at my old company, and she was 29 years old. She and I were in a lot of discussions about the levels of stress she was under at work. The boss that she worked for—she did not feel safe underneath. The boss actually chastised her or made her feel unsafe to go to the doctor during the day.

That’s not what—nope, that is not what you want. And she went to visit her brother the weekend before we were supposed to talk, and she was going to send me her resume, and she ended up getting violently ill and passing away at 29 years old. Oh, and that experience of looking at someone so young who was so sick but ignored the internal signs of her sickness for the level of stress that she was putting on herself and her job on a daily basis profoundly changed my perspective because there is no job, no career, ever worth your health or ever worth your life.

Blake Schofield 13:38
And so I can really relate to your story about your sister in that. That moment for me went, “What in the world?” Because I absolutely know that that work scenario and the belief system she had, and her putting that job ahead of herself and her own personal health, was a huge contributing factor to her passing away at such a young age. And I think often when we get started in these careers and these high-powered, you know, “I got to keep moving up. I have all of this pressure,” we believe that how we feel today is how we’re going to feel tomorrow, and we can become really disconnected from ourselves—connecting to how we’re feeling, how we’re taking care of ourselves and others.

And I see that a lot, especially with people in corporate, repeating the same types of cycles that I was in, that my friend Renee was in, and perhaps that might have been a contributing factor for your sister as well, of just not being able to be fully in touch with how they’re feeling or taking care of themselves because of the pressure of everything else.

Jason Silver 13:58
Yeah, you know, I mean, again, sorry you had to go through that situation. And I think it seems like it did something similar for you that it did for me. I always knew about post-traumatic stress, but it turns out there’s this thing called post-traumatic growth, which is, you know, the substantially happier, substantially lesser-known, I guess, syndrome, or whatever you call it.

I consider myself to be very fortunate that I had some very, very significant trauma in my life, and I’m one of the few lucky people who, for me, it turned into an incredible driver of growth, and I owe that to my sister. And, you know, she lived her life in a very different way. She wasn’t, you know, operating the way that I was. I don’t think there’s anything she could have done differently to know that this was happening. It was going on in her body, and there were no real symptoms or signs that it was happening.

And, you know, she wasn’t deprioritizing it, to the best of my knowledge. You know, she was just kind of always living her life in her way. And it was, you know, a challenging experience to go through and reflect on life and think about the impact on mine, and particularly to be able to sit here now and say, I’ve never felt more impactful with a unit of my time than I do right now. I’ve never felt more centered, more clear, or happier than I do right now.

And for a long time, I dealt with a lot of grief because how can I say that my life is in most of the ways I can measure it better now than it was when my sister was alive? And I couldn’t talk about it. I didn’t feel comfortable trying to say it. I felt like I was going to be judged regularly until I kind of realized that the truth of it is, if I could bring her back, if I could give away everything that I learned between then and now to get her back, I would do it in a heartbeat. But I can’t. And that’s why now I’m kind of on this mission to just—like you don’t need the grief, you know, to get the benefits.

And it’s recognizing that, you know, the gift that I got, I would like to return, but parts of it were a gift nonetheless. And I think the best thing that I can do to kind of carry her memory forward, at least for me, is to share them as much as I can, you know. And I think that’s the thing I’m really passionate about doing now, is just showing how—I still describe myself as a type A, but I think about it differently. I’ve never been more impactful, but I’m focused more on enjoying myself more along the way.

Because if you read the research, the more that you enjoy what you’re doing, the better you do at it. You know, it’s not some fluffy like, “We’ve got to sit around and Kumbaya and all drink some Kool-Aid and have our feet up and have fun all the time.” That’s not what I’m saying. But when you’re in a zone, when you’re enduring your employment all day long, like the odds that you’re also going to be great at it are lower, right?

When you enjoy what you do, you do better at it. And the better you do at it, the more you enjoy it. And the more you enjoy it, the better you do. And it’s this, like, amazing flywheel. And then when things are going really well at work, it spills over into the rest of your life. You have more energy. You’re fired up for what’s happening in life. And the better you feel in life, the better you do at your job. And up and up and up and up we go.

So it’s less of like, my perspective radically shifted and all of a sudden all I cared about was enjoying myself all the time. It was just a recognition of, like, I was over-invested in the future and under-invested in the moment. And how can I transition this a little bit more—not saying like blow all your money and don’t think at all about the future—but are there some things you can do differently?

And by just kind of questioning all the assumptions I had about how I’m supposed to work, and how I’m supposed to live, I kind of started to see, like, a bunch of these assumptions aren’t serving me. I can both accomplish a lot, be a high achiever, and be thinking about enjoying myself now, not just later. And I think that realization—which, you know, I’m thick-headed, it took, like, I probably ran, I don’t know, well north of 100 personal wellness and workplace experiments on myself, of like doing things in different ways, and I kept a tracker, and like, does this help? Does that help? You know, I was working late, working early, working six days, seven days, two days, four days, not setting goals, setting more goals. Polyphasic sleeping, cold plunges—you name it, like I’ve tried all of it.

And the learnings that I was getting out of that were surprising to me. They were counterintuitive in a lot of ways. I thought it was like a scale where you either enjoy it or you’re impactful. It’s rarely both. And what I learned is actually there are some core assumptions about the way that we’re working. We can change these things. There are some pretty simple tactics you can put in place. And when you do, you enjoy it more, you do way better at it, and the impact on your life is incredible.

Blake Schofield 18:27
I love it. Can you share with us some of what those are? What are some of the things you can put into place to figure out how to enjoy your career and therefore your life more?

Jason Silver 18:36
Yeah, I think we can go in whatever direction you want. The idea from the book is basically to take nine of the most common workplace challenges and share an incredibly simple tactic. The rule I had for the book is, if you can talk or you can type, you can try every tactic in my book. And the challenge with it is, you hear things like, “Work smarter, not harder.” That comes up all the time, right? I find that statement borderline offensive. You know, I don’t wake up every day thinking, “Okay, what do I have to get done, and what is the absolute stupidest way that I can think of to accomplish these things?” I’m trying to work smarter, not harder, but what do I do with that kind of thing? And people say, “Find a job that you love, and you’ll never work a day in your life,” right? Okay, no one’s trying to work a job they hate.

What I found is actually removing things rather than adding things was most helpful. So examples of things like this—a common one I talk about all the time—is that in the United States, $1.2 trillion is wasted from workplace miscommunications every year. Big, huge number, right? And they suck because you usually only find out about them afterward. That’s why we waste so much, right? I’m talking to you, we think about a project we’re going to go work on, there’s been some fundamental misunderstanding, we go work on it, come back after two weeks, and it’s like, “Oh, Jay, I wasn’t thinking about it that way.” The work goes in the garbage. That sucks, right?

If you’re a nerd like me and you do the math, that amount of money works out to a full day of lost productivity for every single employee every single week. So that’s how much miscommunications are hurting us at work. And then you think, “Well, how do I improve this?” If I could just fix my miscommunications, I could save a full day every single week, meaning I could literally do five days of work in four with no change, right?

So I was looking at ways to improve communication and found something called a “brief back,” used in the military because it’s not a “ha-ha, we had a miscommunication,” it’s loss of life if we aren’t on the same page. It’s when a listener repeats back what they’ve heard, and it stops miscommunications in their tracks. Why doesn’t this happen in the office? Because it’s awkward, and you can sound like a jerk.

I tried a lot of ways to land a brief back. Most make you sound like a jerk, and nobody wants to work with you, right? So we might be talking, and I’d say, “Hey, Blake, can you just tell me what you heard? I want to make sure you were listening.” No one wants to work with that human. Instead, if you keep it focused on yourself—”Can you let me know what you’re taking away because I want to make sure I did a good job getting my point across?”—it’s about my job communicating, not your listening or intelligence.

It’s awkward the first time you do it, but if you do three of these, you will find at least one situation where there was a miscommunication, and the other person will thank you for saving time. This is a simple tactic; if you can talk, you can try it at work.

Blake Schofield 23:49
I love that. It’s funny; I actually learned that technique back when I worked at Target and what a huge impact it makes in moving things forward. And it’s interesting. I think it seems very small, but there’s usually what I find, internal resistance to people applying that for the very first time, because there’s this whole thing of like, “Oh my gosh, I am going to get feedback, and what if I did something wrong?” There’s a level of vulnerability in being willing to say, “Hey, can you share with me what you heard? Because I want to make sure I did a good job,” right? It opens the door for someone to say, “You’re a terrible communicator,” or “No, I don’t understand anything,” or whatever it might be. But there is such incredible power in that.

I’ve seen exactly what you said: the thing is identified, the person appreciates it, they actually feel that there’s open dialogue. It becomes much faster, much smoother, and much easier over time. As a team, they begin to see how they maybe miscommunicate to people and start applying it. It is this beautiful ripple effect. I agree with you. It’s an interesting thing; we spend a lot of time on tactical skills, and yet almost all of the reasons why we’re not successful as individuals, in relationships, and in companies come down to our relationships with ourselves and others, and being able to understand the blind spots that we have, what we actually need, and what others need, and making sure that we are all in alignment and not perceiving things inaccurately.

Jason Silver 25:16
Yeah, like, that’s the whole point I’m trying to make. You can do a whole load of professional development, and I’m not saying that stuff’s not going to help. I’m not saying that getting a new job, a promotion, or jumping to a new project won’t be beneficial. There are times when you need to do that, particularly if you’re in a toxic environment. Sometimes changing the environment is what you need to do.

But when you look at the Great Resignation—millions of people changed jobs—and they did a big survey: 80% of people regret their decision to change jobs. I think that’s because we don’t change the way we work; we just go to a new place in a new environment, but the same workplace challenges come flooding back. If your communication isn’t on point, you’re going to have miscommunications at the new place just like you did at the last place.

What I found is that there are these small tactics, and it’s great you’ve experienced the brief back. It’s not common in a lot of places. There are ways to fix miscommunication, speed up decision-making, and prioritize more effectively. Imposter syndrome is another topic. The conventional wisdom of “just believe in yourself” often doesn’t work. When I’m feeling self-doubt, what can I actually do about it? I’ve spent a lot of time helping people with these issues and doing research around them. I think there’s a better way.

Blake Schofield 27:13
Oh, I completely agree with you. In fact, pretty much every single person has imposter syndrome, especially if you’re a high achiever, and most of us don’t even understand that it’s part of the growing up process and how we experience things as a child, not being able to understand what our parents’ reactions are and internalizing a lot of that. I completely agree with you. There’s so much conventional wisdom like “hustle, grind, push through it, move forward,” but you’re never going to overcome your subconscious without doing the work.

I also thought it was great talking about the migration of people and jobs. This is something I’m incredibly passionate about. It took me over a decade to see the patterns of fulfillment and unfulfillment in my career. I worked at five different companies over 18 years, and what I always tell people is that they believe the problem is the toxic boss, the company, or the career path. But they’re not actually solving the root cause of why they’re unfulfilled. To your point, they’re continuing that cycle somewhere else, probably improving some things but still dealing with the core root problems because they are the same person moving. People believe their circumstances need to change when almost always it’s the internal that needs to change. When the internal changes, they can accurately shift external experiences or move into an environment that’s better for them.

I love hearing you talk about that. That 80% statistic doesn’t surprise me. It’s a huge part of why I tell people that if you’re unfulfilled in your career and you’re not clear with great depth about why, you’ll just end up back in the same place after spending all that time and energy interviewing and starting over.

Jason Silver 29:26
Yeah, this is why we call the book Your Grass Is Greener. I want to show people they don’t have to look over there. The common expression “the grass is always greener on the other side” is true, but I want to show people they have more agency than they think. The job they have can be better than they believe, and it’s not through the things they’re being told need to change, like a job title. Sure, a new title might make you feel better for a while, but it’s not what truly moves the needle.

I wanted to give people a playbook. Try to solve these nine most common challenges at work first. If those don’t improve things, that might indicate you need to change something external. But before making that change—which is hard to reverse—work through these first. To your point, there’s an exercise I cover in the book that I do with clients: get a two-minute timer, take a piece of paper, and write down everything your iPhone or smartphone is good at.

Blake Schofield 31:00
Oh, I love that!

Jason Silver 31:01
Yeah, take two minutes and write down everything your smartphone is good at—maps, email, Instagram, whatever it is. When the timer is done, you’ll have a list of things your smartphone does really well. Then flip the paper over, set the timer for two minutes, and write down all the things you’re great at. What I’ve seen time and time again is that people finish the smartphone list way faster and have more items on it than they do on their personal list.

The realization is that we often know more about the thing we carry in our pockets than we do about ourselves. If you don’t know what you’re great at, it’s hard to deploy that in the workplace. When you’re not doing what you’re great at, you’re not doing your best work, and you’re not enjoying it, leading to the idea of “best practices” that drive me crazy. Best for whom? The way I do something and the way you do it are unlikely to be the same. Sure, sometimes a task has one optimal way, but often, the approach should vary based on individual strengths.

Take the example of Google Maps; it gives you options on how to get from A to B—by walking, driving, or taking the scenic route. The same applies to work. If you and I are tasked with giving a project update, and you excel at data analysis while I love giving presentations, we should approach it differently. You might send a detailed email and follow up with questions, while I might create a presentation and engage the team in person. If we swapped, neither of us would be happy or do our best work, even though we’d solve the same problem.

Blake Schofield 33:34
Exactly. That’s such a powerful insight. I think many people lack self-awareness about how they work best, leading to unhappiness in their role. They assume everyone works the way they do, which creates challenges, especially for leaders. If you don’t understand your own work style, you can’t recognize it in others, stunting growth across the board. The happier and more aware you become in your career, the better you are at recognizing and empowering those around you. Fear of deviating from a norm or perceived expectation can limit everyone’s potential.

Jason Silver 35:49
Yes, and that’s where a simple shift can make a big difference. One exercise I use when helping teams with quarterly planning is not just asking, “What are we going to do?” but also, “How do we want this to feel along the way?” It’s a question that often stumps people. We plan the “what” meticulously, but the “how” is assumed and implicit.

But when you take 10% of your planning time to think about how you want the process to feel, it changes everything. Maybe you want it to be enjoyable for your team, or maybe you acknowledge that it’s going to be intense with everyone putting in extra hours for a short period. The key is being intentional about it. When everyone knows the plan and how it should feel, they’re more aligned, and that alignment carries through the project.

People often assume that working long hours is inherently miserable, but that’s not always true. There are times when pulling 70-hour weeks can feel exhilarating if everyone knows why it’s necessary and what the outcome will be. It’s different when the team is all in, working together with a shared understanding, compared to when people are just grinding away without context or direction. Taking that bit of time to ask, “How do we want this to feel?” helps leaders communicate more effectively and set the right expectations.

Blake Schofield 38:26
I love that. It’s so simple but so impactful. This approach isn’t just for teams; it works on an individual level too. Asking yourself, “How do I want to feel when I go to work each day?” is powerful. Identifying the gap between how you currently feel and how you want to feel is the first step toward making changes, even small ones, to close that gap.

Jason Silver 39:17
Exactly. The rhetoric out there often makes it seem like you need a massive overhaul to improve your situation. But in reality, the incredible things we accomplish come from a series of small steps taken over time. You don’t have to make a huge change all at once. Start with a small action that aligns with what makes you feel good at work, even if it’s just a few minutes of doing something you enjoy.

Stack those little changes, and you start building momentum. Five days of small changes lead to a better week, four weeks lead to a better month, and so on. It’s a snowball effect. The idea that enjoying your job more requires a major change is misleading. Sometimes, focusing on those little things, like the iPhone timer exercise, can make a big difference. You’ll see tangible results without feeling overwhelmed.

Blake Schofield 41:24
I completely agree. However, there are situations where taking small steps can be risky, especially for someone who’s deeply unfulfilled or burned out. If someone is at a five or below on a fulfillment scale, and they’re only going through the motions at work, making small changes could delay more significant action they need to take. There’s a risk of hitting a breakdown point, leading to major setbacks like a layoff, performance plan, or health crisis.

If you’re experiencing cycles of burnout, high frustration, or emotional detachment, it’s crucial to take a more substantial approach and seek help. Waiting too long puts you in a vulnerable position.

Jason Silver 44:30
Absolutely, there’s no one-size-fits-all solution. For someone at an extreme level of burnout, a bigger intervention might be necessary. The back third of my book is about how to progress faster without waiting for a promotion, which is out of your control. The question is, what can you do for yourself without relying solely on external validation like a job title?

Often, I work with people who feel stuck after being passed over for promotions. It’s important to understand what that promotion represents for you and how you can make systematic changes even if you don’t get it. You have to start taking steps to shift momentum, even if they’re small at first.

Blake Schofield 47:11
I agree. It’s easy to get stuck in the idea that only big changes will help, but taking small actions can make a significant difference and provide clarity. When you feel better, you gain perspective and can make more strategic decisions about your career. Often, people don’t realize the power they have to create change within themselves, which in turn allows them to make better external changes.

Thank you so much, Jason. This has been a great conversation. We even ran over time! Is there anything I didn’t ask that you’d like to share?

Jason Silver 48:15
No, I think you covered everything.

Blake Schofield 48:21
How can people find your book?

Jason Silver 48:28
The easiest way is to go to yourgrassisgreener.com. There, you’ll find all the links to pick up the book or get in touch. It’s available on Amazon, Barnes & Noble, and other places where you find books. It’s highly tactical and designed to help people with clear, actionable solutions. Yourgrassisgreener.com is the best place to start.

Blake Schofield 49:16
Thank you so much, Jason. It’s been a pleasure. I hope our audience takes just one or two things from today and puts them into action to see the impact it can make.

Jason Silver 49:30
Thank you. And thanks to everyone who made it to the end with us. I really appreciate it.