The 2-year Experiment That’s Quietly Changing My Life | The 2x20 Project™ Update

Learn more about working with Jonathan to craft your 2x20 Project™. https://stephanie197.typeform.com/to/a4Z3ruFC#at_click_id=xxxxx Tired of drifting through life on autopilot? Jonathan Fields shares his raw, uncensored journey of intentionally redesigning his ideal life over two years through bold experiments. Discover the breakthroughs, fears confronted, and radical decisions that emerged as he realigned his path around health, passion, and joy. If you crave more simplicity, significance, and authentic living, this candid exploration offers an inspiring blueprint. Episode Transcript https://www.goodlifeproject.com/podcast/2x20-project-update Check out our offerings & partners: Take Our Podcast Listener Survey http://goodlifeproject.com/survey! Join My New Writing Project: Awake at the Wheel https://jonathanfields.substack.com/aboutVisit Our Sponsor Page For Great Resources & Discount Codes https://www.goodlifeproject.com/sponsors/ Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Jonathan Fields?

  So what if you took two years to completely redesign your life? Not just tweak it around the edges, but I'm talking fundamentally reimagining your next 20 years to center greater joy, deeper meaning, more significant impact, or whatever mattered most to you. What would you do? What would you dare to try, to learn, to do, to build? Well, for the past 17 months, I have been living that question. I've been running a series of experiments, some small, some really big, confronting my deepest fears, holding dear to a beginner's mind, learning a ton and uncovering some uncomfortable truths about myself and the way that I've been working and living.

• 0:45Jonathan Fields?

  And what I have discovered is really shaking everything I thought I knew about work, creativity, and what it truly means to live a good life in the best of ways. I'm somebody who has literally been studying the question of good work, good love, good living as my profession for more than two decades. And in this episode, I'm pulling back the curtain with a big update on what I call my two by 20, based on a guiding question. What could I learn, do, or build in the next two years that would set up my next 20 to center simplicity, significance, and joy? Now, I first shared this project with you about six months ago, I guess. And since then, I've been running new experiments and learning so much.

• 1:29Jonathan Fields?

  And today, I am sharing the last six months, the raw, unfiltered journey, the breakthroughs, the breakdowns, the moments of clarity, and the moments of just utter confusion. I'll share all new insights, struggles, experiments, and awakenings that I have experienced since first sharing this adventure with you six months ago. And I'll reveal the one thing that I've been hiding or avoiding for years, the fear that's been holding me back, and the radical decisions that I'm making to finally confront it. So if you're feeling maybe lost, restless, or just plain curious about what your own next chapter could look like, this episode is for you. It's a roadmap for anyone who's ready to stop settling and start designing a life that truly sets their soul on fire.

• 2:14Jonathan Fields?

  And don't worry, if this is your first time hearing about this thing I call the 2x20, I'll also do a bit of a recap of what it is, why you might want to explore your own version, and how. So buckle up, because this is going to be a bit of a wild and, for me, deeply vulnerable ride. I'm Jonathan Fields, and this is Good Life Project.

• 2:42Speaker 01

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• 3:15Jonathan Fields?

  Good Life Project is sponsored by Steo. So I am not in the studio today. I'm actually out on the trail in the Rockies at about 6,000 feet above sea level in Boulder. The leaves are exploding with color and just stunning out. And yes, I'm wearing my favorite Steo hat, and just last night I was wearing one of my favorite Steo jackets, which, if you know me, is not unusual. I wear the hat almost every day, and my Steo jackets pretty much live on me all fall and winter. There's even a Steo shop back in town, practically in my backyard. Here is why I love them. Steo is designed and tested in Jackson Hole at the base of the Tetons by locals who ski and bike and hike and climb and fish there pretty much every day. They have been at it since 2011, so they know warmth and they

• 3:58Jonathan Fields?

  also know style. Everything I have from them, it works great, it holds up in every condition, and also looks awesome. And their hometown down is 800 Phil Down, but if Feels more like just your favorite hoodie than a puffy. And ski season is almost here, so gear up now the way that the locals do. Go to stio.com/goodlife for 20% off your order. That's S T I O dot com slash good life. stio.com/goodlife. Stio, designed and tested in Jackson Hole. Good Life Project is supported by Ernesto rugs. So a small confession, our front porch has been the most neglected corner of our homes since we moved in. It's the first thing anyone steps onto and it's been kind of greeting people with a sad, too small mat.

• 4:41Jonathan Fields?

  Ernesto sent me their samples and now they're making us a rug. And the cool thing is for $10, you get five oversized 12 by 12 samples. So you see the colors at real scale in your own space before you even get it. So we lived with all five colors for a few days and cool morning light and golden afternoon light. And we're sure to be roused on the sky, but Caldwell just kind of kept quietly winning. The thing you're certain about isn't always the thing that fits. And because Ernesto rugs are custom sized, cut to the ins. The one we ordered is made to our exact six and a half feet by nine feet space, not close enough. Visit ernesto.com and order five samples for only $10 and you'll get $50 toward any rug of your choice.

• 5:24Jonathan Fields?

  That's E R N E S T A dot com. So it all started with a bit of a quiet inner whisper that grew too loud to eventually ignore. Not long ago, I found myself at this personal crossroads. By all external measures, life was good. I was doing work that mattered with people I cared about, grounded in values that I spent years identifying. And yet there was this persistent question tugging at me. Is the way that I'm feeling today, especially about my work? How I want to feel for the next maybe 20 years or so of my life, my next major season of contribution? And surprisingly, the honest answer was no. That realization, it hit me pretty hard.

• 6:07Jonathan Fields?

  How could I, someone who's devoted my life to exploring meaning and purpose? Reach a point where is this really it kept echoing in my mind?

• 6:18Jonathan Fields?

  And it sounds almost crazy on the surface. I had clarity on my spark attack, the work that makes me come alive. I was aligned with my core values and I was immersed in missions that mattered. And yet, something felt a bit off. And I remember sitting with that uncomfortable truth, that even a good life can drift away from what truly lights you up. And in my case, an inner voice was calling for another level of simplicity and significance and joy in my day-to-day experience. And rather than ignore that whisper, or panic, and make a rash life change, I chose a bit of a different path. I turned my questioning into an experiment. I secretly launched what I came to call my Two by Twenty, or Two by

• 7:02Jonathan Fields?

  Twenty Project. The name comes from a simple idea. What if I treated the next two years as a bit of a dedicated laboratory, to design the next 20 years of my life? Two years of intentional exploration, learning, and bold little experiments, to set myself up for an incredibly vibrant next two decades or so. It felt like a daring but exciting proposition, a way to actively shape my future, rather than passively default into it. And this approach was very different from typical New Year's resolutions, or midlife crises impulses. Instead of making one big bet, or overthinking my next move, I embraced a mindset of curiosity

• 7:46Jonathan Fields?

  and play. I'd run lots of small experiments, in all areas of my life, gather real experiences and data, and then let those guide me. In other words, I wouldn't just think about what might make my life richer. I'd go out and try things, and see how they made me feel. And this notion of living life as a series of projects wasn't entirely new to me. In fact, I realize I've always been doing it, to some extent, even the name of my company. And this podcast, Good Life Project, it literally contains "project" in the name for a reason. I've often launched new ventures or creative endeavors by saying, I wonder if I'd enjoy this, treating them as explorations rather than permanent commitments. And that framing

• 8:31Jonathan Fields?

  takes the pressure off. It makes growth feel fun and experimental instead of do or die. So in classic form, I approached my own crossroads as a grand personal project. I kept it secret at first, for quite a while, actually. It was just for me. I was a bit nervous to share it publicly. It felt so personal, and I also didn't want external noise or expectations creeping in. But I dove in enthusiastically, starting this journey of learning and doing and building across different facets of my life. Little did I know how transformative it would become. So, over time, as I confided in a few close friends, and this was months

• 9:14Jonathan Fields?

  after I'd started, actually probably close to a year, and I started sharing what I was up to, the reaction surprised me. Instead of saying, "That's a bit bonkers," they wanted to know more. In fact, one friend just outright challenged me. He said, "You have to share this. Others could potentially really benefit from hearing about it." And that nudge is why I'm here talking with you about it today, and why I first shared it six months ago. What began as a private quest has evolved into something of a shared journey. So in our last 2x20 episode, where I introduced the whole concept, I laid out the backstory of my plans, and I'll link to that in the show notes, just in case you're curious. Now, about, I guess, 17 months or so into this project, I wanted to update you on what's

• 9:59Jonathan Fields?

  been happening, the ups, the downs, the surprises, the powerful insights that have emerged, sometimes not ones I necessarily want to face, but really important ones. My hope is that by opening up this process, it might spark ideas for your life, too, or at least make you feel less alone if you're asking similar questions about what's next.

• 10:23Jonathan Fields?

  So let's dive a little bit into, especially for those who are newer to the two by 20 concept, I'll do just a little bit of a debrief from my last one, so you understand what this whole thing is really about. So first, why two years and 20? You might be wondering why that two-year experiment or 20-year vision. In my case, it was really about my age. I had recently turned 58. I'll be honest, the number 60 was looming on the horizon and feeling a little bit weird. And with it, the realization that I may have about 20 or so productive, vibrant years ahead in this next chapter of life. And it felt like an important window, roughly two decades where I could still do meaningful

• 11:08Jonathan Fields?

  work and create and connect and contribute at a high level. Knock on wood for health, right? I wanted to enter that next 20-year chapter with intention, rather than wake up maybe a decade later and think, I wish I had set myself up for this or pursued that. I saw these next two years as a bit of a chance to course correct and design for the long game. So why not just plan for 20 years outright? Well, 20 years is a long time, full of unknowns, but two years is a timeframe close enough to feel real and actionable. It's long enough also to allow significant changes to take root, but short enough to

• 11:50Jonathan Fields?

  create some urgency. And by treating these two years as kind of an incubator, I could try a bunch of different things in a relatively contained period and just see what sticks. It's kind of a bit like a startup accelerator, but for my life, rapid prototyping new ways of living and working now to yield compounding benefits later. So as I see it, when you orient towards the long game, the decisions that you make, they start to change in a really big way. You think less about immediate rewards and more about what will matter a decade, maybe two from now. And that shift in perspective, in horizon alone, can be

• 12:33Jonathan Fields?

  transformative. For me, it brought a kind of peace and clarity. I wasn't in a rush to force an answer overnight. I gave myself permission to live in the question for a while, which is something that we humans aren't always great about. And I should note here, you don't have to be anywhere near 60 to undertake your own two by 20. You could be 30, asking what you want your life to look like at 50, or even 18, contemplating the next 20 years ahead, or you can adjust this however it feels good to you. Make it a one in five or a one in 10, whatever it may be. The framework is flexible. The key is feeling that pull to reimagine your path and being willing to devote focused time to it.

• 13:15Jonathan Fields?

  In my case, two years just felt right as the incubator, the experiment time. It was both manageable period and symbolically significant giving my life stage. And the next 20 just seemed to work as sort of like the next really substantial season of contribution. Now, whether I end up sustaining any of the things that I'll start into or continue forward for another 20 years or not, maybe, maybe not. But when I use that, when I use that as a decision-making criteria or heuristic, it changes the way I make decisions. It lets me let go of all sorts of really less significant things and focus my energy back on the things with truly

• 13:59Jonathan Fields?

  big and deep and rich potential. Let's talk a little bit more then about that guiding question and also the three buckets. So clarity is important in a project like this. I knew I needed an anchor to guide all these experiments, or I might just drift or get overwhelmed. So I crafted this guiding question for my two by 20. It was, what might I learn, do, or build in the next two years that would center the next 20 around simplicity, significance, and joy?

• 14:32Jonathan Fields?

  That single question became my North Star and it remains my North Star. So let me break that down a little bit. Learn, do, or build. Why that language? This phrase reminds me that this is an active exploratory process. I wasn't going to think my way to a new life. We get so caught up in trying to think our way into the future. We can't do that. It never works. I had to get out of my head and take action. Whether it's acquiring knowledge, taking on new activities, or creating something tangible, forward motion is key. Analysis has its place. Contemplation, thinking has its place. But in moments of life that really matter, you can't think your way to an answer. You've got to do your way there.

• 15:17Jonathan Fields?

  So I've come to trust that lived experience is really the best teacher. So this project was about trying stuff and learning from doing rather than endless rumination. What about the next two years? The two-year window? As we discussed, this set my time container. It's kind of like a personal challenge. For two years, I commit to being open-minded, proactive, courageously experimental. Knowing that it was a bounded timeframe gave me both comfort, you know, that feeling like, oh, I can do this for 24 months. And also a bit of a kick in the pants. Don't waste the opportunity because the clock is ticking. It also helped me avoid the trap of inaction. I made a rule for myself. Inaction is not an option.

• 16:01Jonathan Fields?

  If an experiment didn't pan out or felt wrong, that's totally fine. I could drop it guilt-free. But then I had to move on to the next one. No languishing, no wallowing. Keep the momentum. This mindset has kept me from getting stuck if something failed. A failed experiment was still a useful experiment because it gave me data on what doesn't work and freed me to try something else. Okay, what about that 20-year window? This is the horizon I'm aiming for. I was essentially asking, what foundation can I lay in this short period that will allow my, in my case, my 60s and 70s and beyond, to be as rich and fulfilling as possible?

• 16:42Jonathan Fields?

  It's not about predicting the future, but rather about aligning my life now with the direction I hope to grow into. By focusing on that long-term vision, I found that my priorities and even daily habits started to shift in meaningful ways. And I started thinking about longevity, not just physical or cognitive, but creative and emotional longevity. What do I need to put in place so that I can keep doing things I love, keep contributing, and stay healthy and connected over the long haul? Those became my guiding considerations. And then there's that phrase, simplicity, significance, and joy. These three words are core qualities that I crave more of in my next season. They're highly personal. Everyone's might be different.

• 17:25Jonathan Fields?

  For me, significance means pursuing things that genuinely matter to me on a heart level, things I find meaningful and purposeful, where I can feel fully expressed, regardless of external validation. It's not about ego or legacy or what I should do. It's about what lights me up and feels important in the grand scheme of my life. Next, simplicity. And that was about dialing down complexity and stress. And I realized I had been very good at adding complexity, building businesses, launching big projects. And while that brought success, it also brought a near constant background hum of stress. And I am yearning for more ease and grace in how I live day to day.

• 18:08Jonathan Fields?

  Life is going to give me plenty of complexity, whether I ask for it or not. To the extent that I don't have to pile onto that, I am trying to choose not to. So life will always have it, but I don't need to create extra on purpose. And I started asking, well, how can I make this simpler in every experiment? And finally, that last word, joy, the last part of my big guiding question. And maybe the most important, to me, joy is about being fully present to the good in my life. It's less about bursts of happiness and more about sustained senses of lightness and gratitude and delight in the ordinary, being able to actually see

• 18:49Jonathan Fields?

  the humor in even hard things. I want to laugh more, to savor more, to feel my eyes cringe up and light up and wonder and just have a sense of appreciation regularly. And part of that is arranging my life so that joyful moments are more likely, like doing work I love, spending time with people I love to be around. And then part of it is also an internal practice of simply noticing joy that is already there, even when things are hard. And having these three qualities defined was crucial. They became a filter for me. Every potential experiment, I'd ask, will this potentially lead to more simplicity,

• 19:30Jonathan Fields?

  more significance, more joy? And if an idea didn't align with at least one of those, preferably all of them, I put it aside. For example, when considering a new project, I'd check myself. Am I doing this out of habit or because I just, I know how to do it? I'm pretty sure I could, quote, succeed at it, or maybe fear of missing out? Or will it truly simplify or enrich my life? And this kept me honest, and it's keeping me honest, not that I always stick to it, but I try, because I have a lifelong habit of saying yes to too many things. In fact, one of my guidelines was to resist the urge to commit too early to any one thing. I knew that I would be tempted to latch on to a shiny

• 20:12Jonathan Fields?

  new idea just to escape the discomfort of not knowing. Maybe you have been there too. And the mantra became, hold the door open longer than feels comfortable. Keep experimenting and gathering evidence before locking into any one big direction.

• 20:30Jonathan Fields?

  So lastly, the two by 20 intentionally spans all domains of life. Early on, I realized this couldn't be only about my career or contribution bucket. A good life is a balanced life. The classic Good Life Project model talks about three good life buckets. Vitality, connection, and contribution. So in brief, vitality is your state of body and mind, your physical and mental health and energy. Connection is the depth and quality of your relationships with others, with yourself, even with something greater if you have a spiritual leaning. And contribution is how you contribute to the world, often through work, creativity, service, the things that you make and do that leave a difference. So these buckets are deeply interconnected.

• 21:15Jonathan Fields?

  If one runs dry, the others feel the strain. And I knew that if I poured all my experimental energy into just quote, "work" or the contribution bucket, I might end up with a thriving business, but a broken body or a lonely heart, clearly not a win. So I made sure to design experiments in all three buckets. And I used them as sort of like the three major experiment domains to see if I could bring them all along on this two by 20 journey. This was a key insight from the get go. Any quote, "next 20 years" vision worth pursuing had to address the whole of life, not just one part. And with that guiding question, these principles in place, I embarked on my two by 20 journey.

• 22:00Jonathan Fields?

  So let me share with you some of the most significant experiments that I've been running in each of the three buckets. Vitality, connection, and contribution now. Along with the honest truth of how they've been going. I have had some wonderful wins. I've also face planted quite a number of times, but all of it has been rich with lessons.

• 22:23Jonathan Fields?

  And we'll be right back after a word from our sponsors.

• 22:27Jonathan Fields?

  Good Life Project is sponsored by Quince. So these days, I tend to want fewer things made well. That's how I'm thinking about gifts this year, and it's why Quince is on my list. So Quince makes elevated everyday essentials from premium materials like Mongolian cashmere, organic cotton, and stretch denim at 50 to 80% less than similar brands. Cashmere sweaters start at just $50. They work directly with ethical factories and cut out the middlemen. Our executive producer, Lindsay, actually just ordered their organic cotton denim chore jacket in indigo blue. Her verdict: dreamy and soft. She also grabbed Quince's bees oil wood conditioner. It's made in the USA from beeswax and mineral oil. It's food safe, and it's lovely on cutting boards and bowls. And I actually just got the yummiest

• 23:11Jonathan Fields?

  button down from Quince, which is great as the weather gets cooler. So give the gift of quality this holiday season. Download the Quince app for app exclusive authors, or go to quince.com. Get free shipping on your order and 365 day returns. Now available in Canada and the UK too. And when Quince asks where you heard about us, let them know it was Good Life Project. It's the best way to support the show. Good Life Project is sponsored by Talkiiatry. So you know that moment when you finally say, okay, I need some help? That takes courage. And then you start calling psychiatrists and hear, we're not taking new patients, or our next opening is months away. Talkiiatry exists to change that. Unlike therapy only platforms, Talkiiatry is psychiatry. It's

• 23:55Jonathan Fields?

  a 100% online practice where a medical provider can diagnose conditions like anxiety, ADHD, depression, and more, and prescribe medication when it's appropriate. All 800-plus clinicians are in-network with major insurers. Take a short assessment, get matched, and have your first visit in days, not months. More than 300,000 patients have already found care through Talkiiatry. So head to talkiatry.com/goodlife to complete the short assessment and get matched with an in-network psychiatrist in just a few minutes. That's T-A-L-K-I-A-T-R-Y.com/goodlife to get matched in minutes. Talkiatry.com/goodlife.

• 24:35Jonathan Fields?

  Good Life Project is supported by Kachava. So I used to think being salty was reserved for bad moods and pretzels. But lately, I have come to realize that a little salty edge actually makes life, and especially dessert, way more interesting. Any pastry chef will tell you that a pinch of salt isn't there to ruin the party. It's there to make the sweet parts just really shine, which is exactly what Kachava pulled off with their new salted caramel. First sip, I actually laughed. It's that good, rich caramel, a little salty edge, and none of the sugary drawbacks. And it's still the Kachava that I count on. Two scoops for complete nutrition with plant-based protein, fiber, greens, and so much more. No artificial flavors, colors, or sweeteners, no fillers, no nonsense.

• 25:20Jonathan Fields?

  Which if you're feeling a little salty yourself is kind of the point. Embrace your salty side. Go to kachava.com and use the code GOODLIFE for 15% off your order. That's Kachava, K-A-C-H-A-V-A dot com, code GOODLIFE.

• 25:37Jonathan Fields?

  So let's start out with my 2x20 experiments that focus in on my vitality bucket. I decided to start with my vitality bucket because without energy and health, it's kind of hard to do a lot of other things. And in my late 50s, and one thing that's very real at this stage is my body's natural aging process. To put it bluntly, if you don't actively work against it, you begin to lose muscle, strength, and mobility every year. It's actually part of the process of aging. And I want to try and see if I can either stop that or reverse it because I want to be as able as I can be to participate fully in what is available to me. So fast forward 10 or 20 years of neglect.

• 26:20Jonathan Fields?

  And if you don't do anything about these things, you can be looking at a vastly diminished capacity to do the things you love, possibly even facing preventable health issues or limitations.

• 26:32Jonathan Fields?

  I'm pretty determined, to the extent that I have any sense of agency or control over this, not to let that happen. So a big part of my vitality experiments has been establishing robust physical practices and mental health practices that can carry me into the coming decades. Now, for me, one experiment was deceptively simple, just walk more and do it in nature. After a lifetime in New York City, my family, we moved to Boulder about four and a half years ago now. So we're in Colorado and I suddenly had the Rocky Mountains literally in my backyard, the Front Range of the Rockies. I mean, I live at nearly a mile high, 5,500 feet above sea level, and within a matter

• 27:15Jonathan Fields?

  of minutes, I can be in just gorgeous places. So I realized I had this tremendous gift right in front of me, the ability to hike beautiful trails anytime. And hiking had always been something I enjoyed occasionally, like if I was on vacation, but I never really made it a regular routine. So I asked, what if I changed that? What if I integrate hiking into my weekly, even daily, life? Would it boost my vitality, not just physically, but mentally and emotionally, too? So I started small, just going out on local trails whenever I could. I didn't have a lot in my body or my lungs when I began. And pretty quickly, I felt the pull. There's something almost sacred about being out in the early morning light, feet on the dirt, surrounded by trees, the silhouette of these gorgeous flat-armed

• 27:58Jonathan Fields?

  mountains, holding the town in its cradle. It feeds not just the body, but the soul. So over time, I started upping the ante. I asked myself, could I potentially hike maybe four or five mornings a week? This was a bold ask for me because, truth told, I am not a natural morning person. In fact, I've long had a story about myself that Jonathan is a night owl who hates early mornings. But as with many stories, it was worth challenging, right? This is another interesting experiment to run. And, you know, I really started in just in a summer where it was getting pretty hot. It gets really hot out here in the afternoon. And the morning was the only real workable time to hit the trails without just feeling

• 28:43Jonathan Fields?

  like I was cooking in the sun. So I turned it into an experiment. Rise at 6:30, do my usual meditation and breathing, and then head out around 7:00 AM for a hike several days a week. The first week was rough. Let's just say at 7:00 AM, my body was highly skeptical of this plant. And I recall stepping onto the trail one groggy dawn, thinking, this first mile feels borderline evil. My muscles were stiff, my mind was just, I just kind of wanted to be back in bed. But I'd set a rule for myself, unless I was feeling truly ill or injured, inaction was not an option. So I kept moving and a funny thing happened around the 10 minute mark. My body just kind of woke up. The stiffness melted away,

• 29:27Jonathan Fields?

  my heart rate rose and a sense of vitality and even curiosity and joy started to kick in. By 20 minutes, I was genuinely enjoying myself, breathing in the fresh morning air, noticing the deer, the rabbits along the path, the occasional bear, yes, feeling my mood lift. And by the time I reached a halfway viewpoint, maybe a couple of miles in, I was just so glad that I had done it. And every single time I would come home around 8:30 or maybe nine on a long day, just feeling alive. And my mind was alert and my body energized. And on top of that, I had this inner smile, knowing I'd already done something deeply nourishing for myself before the workday even began. And this experiment taught me

• 30:10Jonathan Fields?

  a few things. First, it rewrote my narrative about mornings and my identity around not being a morning person. Turns out I can be a morning person if I'm doing something I love and find meaningful. And the joy of the hike itself became my morning coffee. Okay, so I still had coffee after, but I'm actually on decaf now, but you get the idea. Second, it reinforced how tightly the mind and body are linked. So those hikes, they didn't just strengthen my legs or lungs, they improved my mental state, my patience, my creativity during the day, my focus.

• 30:45Jonathan Fields?

  I often came up with my best ideas for writing or for creative pursuits or for business while I was out on the trail, not staring at a screen. And third, I learned that consistency often requires structural changes, even if they're small ones. Originally, I thought I could just fit hikes in whenever. I mean, come on, it's out my front door, I'm next to the Rockies. How could I not fit it in? But I wasn't doing it. So maybe in the afternoon, I would sneak it in some days, but afternoons just kept getting derailed. Work, calls, or just fatigue or tiredness would interfere. And hikes just wouldn't happen if I left them till later. So the realization was, if I want something to stick, I might have to rearrange my day and make it a non-negotiable part of my morning.

• 31:29Jonathan Fields?

  That was a key lesson. Our good intentions often fail from not a lack of desire, but a lack of just a clear slot in our calendar and the right conditions. Then, of course, winter came. We get some real snow here at altitude. Thankfully, the sun is often out and it feels remarkably warmer than the temperature would suggest it is outside. And I wanted to see if I could actually stick to this commitment even through a snowy winter at altitude. And I'm also not a very cold weather person. I kind of like it just tempered in the middle. So I shifted back to afternoon hikes to better coordinate with the warmest part of the day, invested in cold weather hiking apparel, because if

• 32:13Jonathan Fields?

  you have the right gear, it helps with everything. I got back to three times a week because I wanted to be realistic too, but was proud to be able to say that I hiked through the entire winter for the first time since moving to Boulder in almost five years this winter. And another component of vitality that I decided to dive into beyond my commitment to hiking was strength training. Now, I hadn't lifted weights seriously in years, despite all the research that I know about how incredibly important it is, especially once you were sort of like into and past your 40s. I've always been drawn more to activities like body weight exercise or yoga and figured hiking gets my legs to work out. But as I reached

• 32:56Jonathan Fields?

  But as I researched more on aging, I kept encountering the importance of resistance training for everything from maintaining muscle mass to metabolic activation to bone density. So somewhat begrudgingly, I added a "strength experiment" to my vitality bucket in the 2x20. Commit to regular weightlifting routine. I started very humbly, just a couple of days a week of basic full-body workouts at the local rec center. Honestly, it was a little intimidating at first. I felt weak, which I had never felt in my life. Exercises I used to do easily in my 30s were now challenging. Like the thought of pull-ups, where I used to be able to just knock out sets of them,

• 33:39Jonathan Fields?

  I was like, "Oh, wow. Time of not doing this has taken its toll." But I also approached it with curiosity rather than judgment. Trying different programs to see what I enjoyed and would stick with. And over the months, I kind of found a groove. A mix of hiking for cardio and mood, and weights for strength and resilience and long-term muscle and bone preservation. And the results, I am no bodybuilder, nor do I ever aim to be, but I do feel stronger and more capable. And I just know that I'm doing something that is really good and important for my mental and physical well-being, not just today, but for years and decades to come.

• 34:22Jonathan Fields?

  Each hike or workout is kind of like a vote for the future me, the 70 or 80, maybe 90-year-old that I hope will still be trekking up trails with a pack on his back. I actually regularly see folks on the trail here, who I don't ask their age, but appear to be in their 90s. And it is just profoundly inspiring to me. In vitality, I realize, it isn't just about the body. It's about the mind. It's about your confidence and your sense of freedom. When you feel strong and well, you move through the world with a certain lightness and confidence. You're not as afraid of trying new physical things, of adventure and play, because your body is up for it. And that feeling is so priceless.

• 35:06Jonathan Fields?

  So to the extent that my body has the ability to do this now, and it might not always, and yours even right now might not, and that's completely fine. You know, my quest has been, what is my body capable of doing? What is available to me? And how can I explore that?

• 35:26Jonathan Fields?

  Not every experiment was a home run, by the way, especially in the vitality bucket. I did play around with diet tweaks. Some actually have become sustained changes in the way that I feel in my body. Some completely fizzled out, like trying to cut chocolate, for example. I mean, come on, just no. There is no world where I want to thoroughly be around and never have chocolate. I also attempted to shift my sleep schedule to an earlier bedtime to support those dawn outings. And that one's kind of still a work in process. My body doesn't reset all that well when I do that. Old habits die hard, and I am naturally more of a night owl than a larken. The key has really been approaching these as experiments and not strict rules, not have to succeed type of things.

• 36:11Jonathan Fields?

  So when my afternoon hike idea failed, I didn't beat myself up. I noted why it failed, heat and scheduling in the summer months, and I just tried a different approach. And then I switched it up again to accommodate the seasons. When a dietary change made me miserable, I gave myself permission to drop it. The mantra in action is not an option. It doesn't mean push through everything, no matter what. It just means if something isn't working, do something else. Keep iterating. That mentality has kept me surprisingly positive. I don't see those missteps as failure now, just data on the path to living better in my two by 20.

• 36:51Jonathan Fields?

  And one kind of fun side effect of my vitality focus is that it's often overlapped with the other buckets. For example, sometimes I'll go on those morning hikes with a friend, catching up as we climb. And boom, that's connection and vitality all at once. Or I'll have my best creative ideas for work, contribution, right? During a solo hike, mind clear and open. It's just a great reminder that these good life buckets, connection, vitality and contribution, they're not isolated. A single activity often fills multiple buckets. And overall, I'd say my vitality bucket is significantly fuller today than it was a year ago. I have more energy, less stress, stronger body, practices I genuinely enjoy to keep me feeling alive.

• 37:34Jonathan Fields?

  And that foundation has been really crucial because it gave me the stamina and optimism to tackle some deeper introspective stuff in connection and especially in contribution, which I'll get to, where I've had to actually face some interesting things. So let's talk about the connection bucket experiments that I've run as part of my two by 20 since we last connected in the last six months or so. So my focus was on really relationships with my family, with my friends, chosen family, community, and even a sense of something larger, for lack of a better description. Connection is such a core part of a life well-lived, yet it's just so easy to neglect when we

• 38:18Jonathan Fields?

  get busy or ambitious in other areas. I have been just stunningly blessed to be with my wife for more than 30 years and married coming up on 30 years, like 20 plus years, 27. And we have a daughter who we're just so madly in love with, who's recently ventured out on her own in the world. And I also work closely with my team at Good Life Project and have a very close circle of friends and community. And these relationships, they just mean the world to me. But meaning the world to me and showing up for them intentionally can be two different things.

• 39:02Jonathan Fields?

  So in my two by 20, when I looked at my vitality or my connection bucket experiments, I really set out to actively nurture my connections and even build new ones. One of the most impactful experiments has been a simple weekly ritual with my wife. So we call it our Sunday morning check-in. Now, we've known about the three buckets for years, after all. I developed them and even wrote an entire book about them, but we realized we weren't explicitly using them in any meaningful way to maybe check in on our relationships. So we thought, why not try a weekly practice where we sit down together and talk through each of our buckets as it relates to life and to us? So here's how it works. Every Sunday, after, depending on the weather, I get back from a morning hike or do my morning

• 39:47Jonathan Fields?

  practice. Make some coffee. We settle in on the front porch if it's beautiful out or couch in our living room and we just each share how we're doing in our own personal vitality connection and contribution buckets that week. It's kind of like this gentle state of the union for our relationship and life type of experience. And I might say, you know, this week my vitality felt a bit low. I wasn't sleeping well. I skipped exercise on two days and maybe I noticed I was kind of cranky. I think I need to prioritize a nap or a lighter schedule this coming week. And she might share how her connection bucket is feeling with me or with our daughter or with friends. For instance, maybe, you

• 40:29Jonathan Fields?

  know, I feel like I've been a bit checked out or buried in work or I miss our evening walks or, you know, whatever it may be, we've made it a point of focus to also use I statements and not we statements, which is interesting because often we're told to do the opposite, especially in context of like business and work and leadership, make it a we statement, make it inclusive. But what I found is it's so easy to water down or to hide behind we statements or avoid hard feelings that you are having, not we are having, or struggles by using that shared language instead of just owning how we each individually truly

• 41:13Jonathan Fields?

  feel. So that was another kind of awakening as we deepened into this practice over the last six months or so. We also discuss our connection with each other. Are we feeling in sync, distant? Have we been making time for fun and affection? Are there any little grievances or needs that went unspoken during the week? It's a safe space to surface those things before they grow into real issues that could be much more derailing. We talk about our extended connections too, whether we've touched base with close friends, how family members are doing, even our sense of connection to community or whatever sense of spirituality we have that week. What this ritual does is it opens consistent lines of communication and adjustment.

• 41:58Jonathan Fields?

  Instead of drifting apart slowly or accumulating misunderstandings, we catch them early. It creates a container where both of us feel heard and supported and where we actively work as a team to keep our buckets in a healthy place. And it's amazing how something so simple, a simple structured conversation, once a week can markedly improve your sense of connection. And this is an experiment that worked really well and has now become a fixture in our lives. Another connection experiment that I've tried revolves around friendships and social life. As an adult, especially past midlife, you know, it actually takes a lot of effort to maintain or make new genuinely deep, real friendships. We all get busy.

• 42:42Jonathan Fields?

  Weeks or months can slip by unless someone reaches out. I cherish my close friends. I tell my good friends that I love them all the time. And I also know that making new friends or deepening newer friendships is important, especially after moving to a new state like we did. You know, we kind of blew up our whole life and we're starting fresh in an entirely new place. So I set a goal to arrange two, quote, friend dates per week. These could be as simple as a video chat with an old friend back in New York or anywhere else around the world. I'm very fortunate to have a friend community that's kind of distributed literally around the planet. Or it could be meeting someone local here in Boulder for that ubiquitous Boulder activity, a hiking chat.

• 43:26Jonathan Fields?

  Here oddly, people don't just go for coffee. They'll go for a hike together, which can be awesome. Sometimes you do just want to hang out and have coffee, as my wife sometimes reminds me. Scheduling two friend meetups each week was an interesting experiment. You know, on the one hand, when I pulled it off, it was amazing. It felt great. I'd have these energizing conversations and laughs and heart to hearts or sometimes talk about really hard things that we were moving through and feel heard and seen and supported and sometimes emotionally and physically hugged. Sometimes it was just casual fun and I think, why don't I do this all the time? It really did fill my connection bucket. I felt more supported and connected to my community.

• 44:09Jonathan Fields?

  On the other hand, I discovered there can be weeks where this goal is tough to meet. Life happens. Maybe I'm traveling or they're traveling or have a heavy workload prepping for an event or a deadline. A couple of times I found myself actually stressing about an upcoming planned hangout because I felt pressed for time, which is ironic since friendship shouldn't feel like an obligation. And I even noticed that if I force it during an extremely busy week, I might physically be with my friend, but mentally still be at my desk or my computer, wherever it is I'm working on, which really isn't fair to them or to me. So the lesson there was about being flexible, holding these things lightly.

• 44:53Jonathan Fields?

  The experiment started with kind of a rigid goal, two per week, no matter what. But I realized it's okay to adapt, to acknowledge the realities of life. Now I treat it as a kind of like an average, an intention rather than a hard rule. So over a month, I want to be able to say that, you know, I have had, let's say about eight friend connections, so an average of about two a week. If one week is zero because I'm just slammed, then I actually will try and double up or increase the amount that I have in other weeks. And I also learned to pick timing wisely, scheduling friend time when I can truly be present, like maybe a Friday late afternoon when work is winding down and I'm a little

• 45:38Jonathan Fields?

  bit useless anyway from a work standpoint, instead of mid Wednesday when I'm just in the thick of everything. This way, it stays a joy and not a source of guilt or pressure. And the big takeaway from this, even the things that we do for connection and joy can inadvertently become stressors if we treat them too rigidly. I had to remember the spirit of the experiment, which was to enrich my life, not add another item on a to-do list. And lastly, a, I guess it was a subtler but profound part of connection for me, this was another experiment, was spiritual or nature connection.

• 46:21Jonathan Fields?

  I have always felt something special in nature, a connection to a larger whole. Like, that's kind of where I go to experience something spiritual. Making hiking a regular practice, it also kind of doubled as a spiritual nourishment experiment, you know, which is part of connection, you know, if you feel a sense of connection to something bigger than yourself. There were moments on a quiet trail at sunrise where I just felt deeply connected to everything, call it nature, universe, God, whatever you want to name it. That sense of awe and belonging in the bigger picture, a larger context, became more frequent, and it's been just really nourishing and healing and inspiring.

• 47:06Jonathan Fields?

  You know, I don't have to show up at a building and do some official form of worship, at least in my context, that may work fantastically for you. I find that I can get a really similar feeling when I step into nature. It reminds me I'm not alone, and it instills a sense of gratitude and stewardship for what's around me and for life. So, in a way, my connection bucket experiments also blur beautifully with vitality, as I mentioned, and even with creativity and purpose. And if vitality gave me the energy to pursue change and go out and do these things, connection gave me the support and the motivation to deepen into them. Knowing I have loving relationships and actively nurturing them created a bit of a safety net

• 47:51Jonathan Fields?

  also. It's easier to take risks in other areas when you know you've got people who care about you no matter what. And by the way, if you're listening and thinking about your own life, I can't recommend that Sunday check-in enough, or any regular space to just communicate with your loved ones. It's such a simple thing that anyone can try, and for us, it's really been a game changer. And you can even do this just with, you know, like, close friends or chosen family-level friends, so that you feel like there's never anything building between you. Okay.

• 48:28Jonathan Fields?

  Now it's time. We are going to drop into the contribution bucket experiments, which is where the biggest things have happened, the biggest awakenings, the biggest experiments, sometimes the biggest confrontation with what's happening inside my heart and head. So the contribution bucket is really what catalyzed the entire two by 20 journey for me. Essentially, the work I do now and how I bring my energy, my effort, my love, my spark type, my taste, identity and gifts to the world. This is what that is, right? So it's been really important to me to run really intentional experiments as part of

• 49:10Jonathan Fields?

  my two by 20 that focus into this domain. This is also where I felt the most tension initially. I was working hard and achieving, but something in the way that I was working or what I was working on, it wasn't giving me the feelings that I yearned for, not entirely, not that it's devoid of it. I do enjoy and like and feel nervous by a lot of what I do, but there was enough of it that wasn't getting me there. And I started questioning what was sustainable, right? So remember those three magic words for me, and yours could be different, simplicity, significance and joy. So a large part of my two by 20 has been about reimagining my work and creative expression.

• 49:54Jonathan Fields?

  This bucket has several experiments from exploring new professional roles to rekindling old passions. So one big question on my mind was, in my next season of work, do I want to work more intimately with people rather than at scale? Over the past decade, honestly, two decades, my work with Good Life Project has been mostly through media, podcast conversations, books, speaking in large groups, creating tools like spark types. You know, these often reach millions, sometimes even like Good Life Project has literally been listened to and viewed over 100 million times. It's been just stunningly impactful, but often on a truly one to many level.

• 50:42Jonathan Fields?

  And I started to wonder if I was missing a component of one to one, or at least one to some smaller group, more intimate interactions, like coaching or mentoring or teaching in a more personal setting. Now, I have a very past life background as a lawyer, and I'm an entrepreneur, and I've done plenty of advisory work. I've done a lot of work that would be considered sort of like strategic advising, and probably on some level, coaching in one to one with small teams, with founders, leaders over the years, and really enjoy it. But I was curious what it would feel like to potentially work with individuals on a deeper, personal journey. So people in the thick maybe of navigating meaning and purpose, transitions, kind of like I've been.

• 51:27Jonathan Fields?

  And to test this, one of my early experiments was actually on the learning side. I was wondering, do I need to actually get training or certification or learn more? I've done a metric ton of this in the past, but I was like, is there something else that I actually need to know before I can even run the experiment of working with people on this level? So I decided to become a student again as one of my experiments. Specifically, I enrolled in a three-month intensive training program for Unique Change Facilitation Modality, somewhat unconventional approach to personal development, to coaching, that I'd had my eye on for actually over a decade. I'd seen so many colleagues go through it, was intrigued by the tools.

• 52:09Jonathan Fields?

  And part of my hypothesis was that maybe this might not only teach me new techniques to help others create change, but also clarify if I enjoyed that kind of one-to-one work enough to make it a part of my next 20 years, or if I might enjoy it. So imagine me, 58, sitting in a classroom, sometimes in person. I'd got on a plane, sometimes virtual, doing homework, doing my readings, doing my assignments, practicing techniques with fellow students, basically re-immersing myself in quote "school." After So many decades, always being on the other side of this type of experience,

• 52:51Jonathan Fields?

  the one teaching, advising, or presenting, I was now in the student's seat. This was really humbling, but also really exciting. I learned a lot during those three months. And the modality itself was fascinating and did equip me with some new tools for understanding human behavior and guiding transformation. But here's what else I found. The modality and the way it was taught, it also didn't quite resonate with me. I won't go into details, but the style of practice felt just misaligned with my intuition and values and it's a perfectly valid approach that works for many, but it wasn't right for me. And additionally, I remembered something about myself. I am a bit of an, what we call, I guess, an autodidact, meaning like I'm a self-learner

• 53:36Jonathan Fields?

  more than anything else. I learn by immersing myself in things and doing. I love learning, but I tend to prefer self-directed learning or one-on-one mentorship over broader classroom type of settings. And in the group program, I often caught myself analyzing the teaching format instead of fully being in the student experience. And as somebody who has done so much instructional design, so much teaching, so much facilitation for so many years, that is one of the things that's hard to pull out of. It's kind of like an occupational hazard for someone who designs learning containers and experiences for others. And just to be sure, though, I went ahead and even after I decided that wasn't quite right for me, I'm like, well, maybe it's just that there's something different that

• 54:21Jonathan Fields?

  would be more right for me. And I didn't want to just sort of, you know, like completely run from this idea. So even though I looked at that prior experiment and said, okay, learned a lot, but also learned that I didn't want to continue along that path, I went ahead and I rolled in a second, much more in-depth, eight-month training. And three months in.

• 54:46Jonathan Fields?

  The very same feelings were starting to bubble up. The learning container, it was good, it was solid, but it wasn't right for me. Nor was the nature of the content or the pace of the learning and instructional design. So I could have looked at this and said, but I committed to it. I have to do it. But that's not the ethos of the experimenter. So I withdrew from real time participation, knowing that when it ended, I would then circle back and move through all of the educational content at a much more accelerated clip that then would work for me. And at the end of those experiments, I had a bit of a mixed report. On the plus side, I did confirm an interest in working closely with people on potentially meaningful life questions.

• 55:30Jonathan Fields?

  That curiosity was still there. On the minus side, I realized that this particular path and maybe formal group trainings in general, it's not how I wanted to get there. And it wasn't really adding to what I felt was increasing my understanding of my value if I decided to step into that domain. The great thing about framing it as time bound experiments was that I didn't feel bad about walking away from either of these afterwards. In the past, I might have thought, you know, oh, man, I invested so much in that training. You know, I learned a very specific modality. I guess I kind of have to follow through and incorporate that method into my work or maybe build a whole practice around it. Not now, I don't feel that way. I gave myself permission to say, well, that was interesting.

• 56:15Jonathan Fields?

  I learned a lot. And this approach, you know, there are little things that I'll carry forward, but more or less it's not for me. I declared those experiments complete and learned what I could learn from them and moved on, carrying forward the clarity and the wisdom that they gave me. And along the way, I also, I did another sort of like micro experiment. I spoke to a small number of friends who I trust deeply, who are, will always be honest with me, who have also been coaching and advising at the absolute highest levels, each for more than two decades. These are people who are wildly accomplished, work largely just with CEOs and senior leaders and have long waitlist.

• 56:56Jonathan Fields?

  And they said to me the exact same thing. No certification or training is going to give you what you need or want right now. You have literally been doing this for people, for leaders, for organizations for years, which has never called it coaching or advising officially. It was always, you know, strategy work or something like that, or consulting. But it's really all the same thing. And you've got deep chops and frameworks and approaches and wisdom and a powerful track record of accomplishment. So if you want to do this, they said, stop futzing around with more education and just, well, I'm not going to use like the exact language, but just do it. It's good to have friends who will tell it like it is.

• 57:39Jonathan Fields?

  So yes, more advising slash coaching might be my future, either individually or intimate group experiences. But no, I don't need to force myself into an existing mold or extensive multi-year certifications if they don't feel aligned. For many people, they do, and it's a fantastic move. They just weren't right for me. I can chart my own approach, perhaps blending what I already know from decades of experience with a few select new tools that I find useful. And funny enough, because of the incredible response to the whole two by 20 framework, which was never the early intention, some of this may well revolve around guiding others through their version of a similar process. And I'll share a little bit more on that when I wrap this up.

• 58:24Jonathan Fields?

  So next up in the contribution bucket, when it comes to experiments, was a return to my creative roots. Long before Good Life Project or even the businesses that I've run existed, I was a writer and a maker. I painted and drew and built things nonstop as a kid. That is my spark type. The primary is the maker. And I even renovated houses through college. Sure, it gave me money, but I also did it because it's almost like I couldn't not do it. It was a part of me. In my twenties and thirties, I blogged prolifically, like really deepening into writing, started writing the first of what would become a string of books. I am a maker through and through. That's what gets me up in the morning and drives me.

• 59:06Jonathan Fields?

  I even started my public journey with a blog called Awake at the Wheel back around 2008 to 2010 ish, which has had a rebirth in the last year. Writing has always been a part of me. I've written books. Of course, but in recent years, here's the thing, I wasn't writing as regularly just for expression or sharing ideas. I missed that. There's a kind of thinking that only happens when your pen hits paper, your fingers hit the keyboard in a free-form way, and I felt a bit disconnected, really, from my own voice, my own creative expression. I felt like I was performing to other people's wants.

• 59:50Jonathan Fields?

  So I launched a bit of a public writing experiment. I revived that Awake at the Wheel name from the early aughts, this time as a newsletter on Substack committing to writing a weekly essay or articles. My single promise was a weekly wake-up call to help you feel more alive and less alone. By the way, that's still going. You can go and read it if you want. This was both exhilarating and a little bit scary. Exhilarating because the first time I hit publish on a piece and send it out to subscribers, I felt this rush I hadn't felt in years. Scary because I wondered, do I still have things to say that are in any meaningful way different than anyone else? Will I be able to keep up the cadence?

• 1:00:34Jonathan Fields?

  What if it becomes a quote, "burden"? And I promised myself I'd do it for at least a few months and then evaluate. This was another experiment, right? Initially, I was brimming with ideas, topics I wanted to explore, stories I could share. The reception was encouraging. Folks started signing up and reading and commenting, and some of them replied with really beautiful thoughts and insights, which made me feel like it's a two-way conversation again. It was like, really like the old, the old golden days of blogging. I feel like such an old codger when I say that. It definitely scratched that itch of significance and joy for me. I mean, I was engaging with meaningful topics and reconnecting with a craft that I love. However...

• 1:01:18Jonathan Fields?

  True to form, I almost sabotaged this very experiment early on. So how? By overcomplicating and overpromising. The very thing I'm trying to not do as part of my two by 20. I got overly ambitious and started imagining a whole platform. Maybe I should do multiple posts a week. Maybe add a page here with bonus content and all sorts of commitments and expand into community feature and build, you know, like webpages and this and that and events and all sorts of stuff and courses and programs. My brain was on fire with possibilities because this is what I have done for most of my past, you know, like 25 years. I'm a maker and this is kind of the mode that I've been in. But I noticed something.

• 1:02:01Jonathan Fields?

  I started feeling pressure instead of joy. It was the exact opposite of simplicity. I was taking a lovely, simple writing practice that let me express what was on my heart and, and mind and turning it into a complex project with expectations and attachments. And one day I sat down to write and I felt dread, like, ugh, I quote, have to do this. People are waiting. And then I caught myself. I remembered, you know, the whole point of the two by 20 was to find joy and meaning and not create new burdens. So I hit pause and reevaluated.

• 1:02:45Jonathan Fields?

  I consciously stripped the experiment back down to its essence. I literally, there are a whole bunch of people who are signing up for sort of like bigger, you know, better, more complicated, more abundant promises. And I literally shut that down and refunded everybody's money very quickly. Just write one heartfelt piece a week became the focus in my real voice on topics that feel alive to me. No grand plans, no audience growth tactics, nothing beyond this. That simple shift. So this was almost like running a new experiment within the experiment. It brought the joy rushing back. I fell into a comfortable weekly rhythm. Saturday mornings became my writing time.

• 1:03:30Jonathan Fields?

  I'd make a cup of coffee, sit in a cozy chair by the window and just let the thoughts and the feelings flow. And some weeks the words came easy, other weeks it was more of a slog. But net-net, I was kind of loving it and still am. And it felt like a part of me that had been dormant. You know, the maker part, where I was writing simply for the purpose of writing, it started to wake up. And as of now, I've got that awake-at-the-wheel substack going for just about a year. And it's growing really quickly. Over 10,000 subscribers have become a beloved part of my week and regular readers. Will it turn into something bigger? I don't know. Maybe, maybe not. The thing is, I'm not intentionally forcing it to.

• 1:04:15Jonathan Fields?

  Like, I don't have this now thing that says it has to. It's simply an ongoing experiment in letting creativity be just creativity. Without immediately trying to monetize it or turn it into a massive thing. This has been a huge lesson for me. Not everything you create has to become an enterprise. It can be enough that it brings you and maybe a handful of others joy. And ironically, by keeping it light and joy-driven, it has grown organically and steadily on its own. Simplicity and joy for the win. So other experiments under the contribution bucket, art-making for the sake of making,

• 1:05:00Jonathan Fields?

  or art and making for the sake of making. So I mentioned writing, but I also have a more tactile, creative side.

• 1:05:11Jonathan Fields?

  As I shared, I used to paint as a kid and into my teens. I was the art kid who could lose hours to a canvas or a sketch pad. And that part of me, it kind of got left behind as quote adult responsibilities took over. And lately, I felt this strong urge to get my hands dirty again, to play with colors and wood and shape and anything and even metal. I literally started doing metalsmithing. I've been taking classes in metalsmithing, which is freaking amazing. And just start to create more things in the physical realm. So I planned experiments around physical and visual art. As I mentioned, one is metalsmithing, like learning to actually make things with silver and mixed metals and jewelry and things like that.

• 1:05:55Jonathan Fields?

  And I'll probably start to share some of that fairly soon. It's wildly embarrassing, but at the same time, it's not because I'm a total newbie and loving it. And I also want you to feel like it's okay to be a total newbie at something too and take a long-term horizon on what it would feel like to deepen into it. Also, visual arts, like I'm looking at setting up a simple art corner in my home office or my garage, actually easel paints, maybe a woodworking bench and give myself permission to just dabble and experiment and grow, not for a product, not to sell. I mean, if that happens one day, who knows? But that's not the initial intention. I don't want it to be.

• 1:06:36Jonathan Fields?

  It's just to re-experience the process of creating without any big stakes other than, is this helping me feel more alive? Actually, put a date on the calendar to have my first quote art day and I bought some supplies. I have consistently done this by deepening, as I mentioned, into things like metalsmithing. And now I'm shifting more into visual arts and I'm going to start writing a lot more in a more personal way. And let's just call this a series of ongoing and evolving future experiments. But just the act of preparing for it even has given me butterflies, a good time. It's like making a playdate with my childhood self.

• 1:07:20Jonathan Fields?

  I anticipate that even if what I create is Really not all that interesting aesthetically. The experience will be meaningful and it will grow and change over time. I'll start to gain skills and capabilities and be able to more readily close the gap between my own aesthetic taste and my ability to create work that meets it. So one realization I've had is that creativity is also a form of self-connection. When I allow myself to play and make, I connect with deeper layers of myself and often that reflects back into how I show up in work and relationships with more wholeness and joy.

• 1:07:59Jonathan Fields?

  You know, before I wrap up on the writing experiments also, or the art-making experiments, there's a blend between art-making and writing that's kind of starting to emerge. Last November, a friend of mine asked if I would do this, join her in doing this thing that is called Nano Remo, which is shorthand for National Novel Writing Month, where hundreds of thousands of people from around the world commit to trying to write a crappy first draft of a novel in 30 days. So you have to average about 1,500 or 2,000 words a day to do this. So of course, I had no time, no business doing this, so I said yes. And I got two weeks into that before life really intervened and business got really complex and I had to pull out.

• 1:08:44Jonathan Fields?

  But I was able to generate about 25,000 words towards this and I've never written fiction in my life. I didn't read a lot of fiction until very recently and there was something really magical about just the whole idea of not writing about what I know in a real-world, utility-oriented context, but literally making up a world that did not exist, making up people that did not exist, making up backstories and interactions and moments and characters and qualities and storylines. It's tapping into a part of my maker side that is really powerful. And I set that aside, but I am going to dive back into that and continue with that experiment of writing fiction and see where it leads.

• 1:09:30Jonathan Fields?

  And we'll be right back after a word from our sponsors. Good Life Project is sponsored by Bombas. So my wife Stephanie has been one of the great gift givers in our family. And her secret is that the best gifts often aren't the flashy ones. They're the ones that people reach for on any given day without even thinking about it. That's why so much of my list ends up at Bombas. Fuzzy Sunday slippers for the friend who lives in sweatpants from November to March. Merino wool and cashmere blend socks for anyone who runs cold. That would be me, by the way. Ski and running socks for the ones who refuse to slow down. Also me, by the way. And water resistant suede booties. So cushy. My executive producer Lindsay actually more or less lives in hers. And

• 1:10:11Jonathan Fields?

  here's what else makes it a good life kind of gift. For every item you purchase, Bombas donates an essential clothing item to someone facing housing insecurity. One purchased, one donated. Over 200 million donations and counting. So every gift you give is really two. So head over to Bombas.com/goodlife and use the code GOODLIFE for 20% off your first purchase. That's B-O-M-B-A-S dot com slash good life, code GOODLIFE at checkout. This message is brought to you by Apple Card. Ah, fall, that cozy season where we swap the swimwear for sweaters and sunnies for scarves. But before the Halloween decorations are put away or Thanksgiving table has been set, there's already holly jolly music playing

• 1:10:55Jonathan Fields?

  in the grocery store, reminding you that the year is coming to a close. Time to kick end of year into high gear. When you use Apple Card with Apple Pay, you earn 2% daily cash back on all purchases, including food, decorations, gifts, and more. Get a head start on your end of year purchases. Apply for your Apple Card in the Wallet app on your iPhone today and start using it right away with Apple Pay. Subject to credit approval. Apple Card is issued by Goldman Sachs Bank USA Salt Lake City Branch. Terms and more at applecard.com.

• 1:11:30Jonathan Fields?

  Fairlight Project is sponsored by Vinted. So here's a question that I have been sitting with. How many things in your closet were bought for, let's say, a version of you who never quite showed up? Maybe it's the tailored jacket for the dinners you were gonna go to, or someday pieces with the tag still on them. They're lovely clothes. They're just not yours anymore. That's where Vinted comes in. So Vinted is a secondhand marketplace app where everyday people sell the clothes that they're not wearing to people who actually will. Listing on Vinted is quick and simple. You take a few photos, write a short description, and you're done. Once something sells, Vinted creates the prepaid shipping label for you. There are also no seller fees on Vinted. So whatever your piece sells for, you keep.

• 1:12:12Jonathan Fields?

  What I love about that is how it turns letting go into something that actually feels good. You get more room, a little extra money, and maybe a closet that reflects who you are right now. So see what's hiding in your closet. You might be surprised how much you can earn with Vinted. Download the Vinted app for free and start listing with no seller fees. So you keep everything you earn.

• 1:12:34Jonathan Fields?

  Spinning into more ideas in the world of ideas, it also reconnected me with speaking. So, you know, for many years, I did a fair amount of public speaking and keynoting and facilitation. And I've really pulled back. Over the last couple of years, I pulled back a lot on giving talks or keynote speeches, partly the pandemic, put live events on hold, partly I was just busy with other projects and also building two different businesses. But as I imagine the next 20 years, I asked, do I see myself potentially on stages again, sharing ideas and insights, and maybe just stories as literally as a form of artistic aesthetic expression

• 1:13:19Jonathan Fields?

  and energy in a live room? And probably to my slight surprise, the answer was yes. I do miss that spark of live connection with an audience. And I have new things that I want to say and share now, new ideas, new stories after all these experiments and lessons that I wonder if they might really resonate, especially in this moment in time, and especially with people who are navigating transitions or seeking more fulfilling lives. So I've begun to accept a few new speaking invitations as experiments. Instead of reflexively saying, no, I'm not available, or I'm not doing that right now, I started saying, you know what? Let's try saying yes to a couple and see how it feels.

• 1:14:04Jonathan Fields?

  So, you know, I gave a small talk at a conference not long ago, and let me tell you, I felt a little rusty at first, butterflies in the stomach and all, as you should. But once I got going, it was like this muscle memory kicked in. I was in my element, just interacting with a live crowd, sharing ideas and stories, feeling that immediate feedback loop of energy. And I came off stages buzzing with aliveness. And it confirmed for me that speaking in a balanced way, not making speaking my living, again, really, remember, this is not what this is about, right? But bringing speaking, more speaking into the blend of what my next 20 might look like, that might very well be a part of that next season.

• 1:14:47Jonathan Fields?

  The key will be doing it with clear intention, new topics I care deeply about, and events that align with my values. And also to balance things, so not so much travel or frequency that it disrupts the simplicity and connection that I want. I've actually become deeply interested in what I call being wired for possibility, and I'm excited to speak more on this in the future. And in two by 20 style, I'll probably try a handful of talks and then evaluate how it's affecting my life before ramping up further. So far, so good, though. It's been a lot more joy than stress. And yes, lest I forget. There is another book on the horizon.

• 1:15:29Jonathan Fields?

  Actually, there's more than one other book on the horizon. If you knew the list of books that I want to write right now, it would probably keep me busy for the next 15 years. And likely not just traditional publishing and prescriptive nonfiction, which has been what have kind of built my bones in for the last 15 years or so as a writer and as an author. I am excited to explore a more bespoke artisanal approach to publishing, creating small batch, genuinely beautiful, limited edition social objects, and potentially even taking people along on the maker's journey behind the scenes. And I'll probably be sharing a whole bunch more on that in the not-too-distant future

• 1:16:14Jonathan Fields?

  as that next experiment really starts to take shape. So stay tuned on that. Now, last but not least, within my existing work at Good Life Project, we have been innovating and iterating. After 13 years, Good Life Project itself is probably ripe for a little bit of reinvention, conveniently aligned with my own personal explorations. So the team and I, we've been just testing ideas and formats to serve the community. We've been exploring video for the first time in over a decade, just to see how we feel about it and to see how people respond to it with more visual conversation and storytelling, and how we like creating it.

• 1:16:59Jonathan Fields?

  I'm not sold, but we're running the experiment and will likely ease into more of a selected episode format or a micro documentary format. These are all experiments that we're kind of looking at and thinking about running. And maybe we'll even hit the road at some point later in the year and do some live taping events, which would be super fun to all be together in a room, asking questions collectively.

• 1:17:26Jonathan Fields?

  So as you can tell, the contribution bucket was a big area of focus. It had the most moving parts and some of the biggest personal challenges for me. Changing how I work, confronting fears of irrelevance or failure, rediscovering buried passions. It's still very much in the process, but I already feel a significant shift. If I compare how I feel about my work now versus a year ago, I feel more energized and creative and aligned and alive. There's a spark of possibility that had dimmed a bit for a while and is now starting to glow a little bit brighter. And crucially, I feel like my work is starting to align more with who I am now, not who I was 10 years ago, or 15 years ago, or 20 years ago.

• 1:18:10Jonathan Fields?

  And that's a critical distinction. Many of us get stuck doing what we're good at and known for, long after it fulfills us. I was determined not to let that be my story, and I felt like maybe I was falling into that a bit. So this two by 20 has been a way of proactively updating my story while I'm still in it, so that the next chapters and seasons reflect my own personal evolution. Now, there've also been some pretty personal awakenings and deeper realizations here as we kind of start to head towards a bit of a wrap up. So as much as I love discussing the external experiments, the hikes, the writing, the

• 1:18:53Jonathan Fields?

  training programs, some of the most profound parts of this journey have been the internal shifts, the realizations and breakthroughs in my mindset, emotions, and understanding of myself. So I thought I would share just a few of the big ones with you because I suspect they're fairly universal in a lot of ways. So one is about embracing creativity as identity, not just activity.

• 1:19:18Jonathan Fields?

  One breakthrough has been a reclamation of my maker self, Jonathan the maker, as a core part of my identity. Somewhere along the way, in the busyness of building companies and producing quote, "content," I had unknowingly put some of my pure need to be a maker on the back burner. So yeah, sure, I was creating things like podcast experiences, companies, tools, businesses, but it often had this, almost like utilitarian flavor tied to outcomes and results, and providing economic value for others and solving problems for others. Through the experiments in writing and considering art and speaking and working with my hands,

• 1:20:04Jonathan Fields?

  I reconnected with the artist inside of me. I had this moment after publishing a particularly personal essay on my Substack where I felt naked and vulnerable, but also authentically myself. It was like, oh, there you are, Jonathan. The writer, the storyteller, the artist who finds meaning in shaping words and ideas. The one who doesn't always have to make things purely in service of solving a problem. The one who simply needs to make as a way to feel alive, to breathe, to fully express my unique aesthetic sensibility and taste, and to evoke emotion, starting with my own. And I realized that for me, creativity, it's not a luxury.

• 1:20:47Jonathan Fields?

  It's not like, oh, this is something that you earn your way into or buy your way into being able to do.

• 1:20:53Jonathan Fields?

  It's a necessity. It is literally a part of my DNA that gets snuffed out when I don't honor and center it. If I go too long without making something for the sake of expression only, my spirit just starts to wither. And this was a huge realization. It was, you know, honestly, it wasn't a realization. This was a homecoming for me because I've always known this about myself and had walked away from it in so many ways, for so many reasons. You know, many of them practical and real and trying to be a quote, "grown up."

• 1:21:27Jonathan Fields?

  But there was a piece of myself that was always left out of the room, and I was aching because of it. And acknowledging this, it changed how I prioritize my, my energy and my time. I used to treat creative pursuits not tied to, quote, solving a problem as secondary to real work. Now I see it as non-negotiable. It's just a part of who I am. Even if it never makes me a dime, or even if no one else ever sees the output, the act of creation, of making, keeps me in touch with my soul.

• 1:22:01Jonathan Fields?

  There was actually a poignant realization during one of my hikes. Trail is great for epiphanies, by the way, where I recalled myself as, as a kid, painting in this tiny makeshift studio in the corner of the basement of my family home, just utterly alive in the creative process. And I asked, what's really different now? And honestly, the main difference was that back then, I wasn't worried about an audience or a business model. I created because it brought me joy and helped me make sense of the world. And I smiled because I understood I could have that again, right now, at this age, in this stage, and in the season to come.

• 1:22:45Jonathan Fields?

  The conditions have changed, sure. But the inner maker is and has always been alive and well. So I made a kind of vow to that younger me and to my future self, never abandoning your maker spark again. No matter how, quote, practical life gets, yes, I need to pay the rent. We need to have, you know, meet all sorts of responsibilities and obligations, but always keep an outlet that is just for exploration and expression. And this mindset is now baked into my two by 20. I see myself, you know, in my 60s, in my 70s, my 80s, maybe later, just still writing, not just commercial books, which I also do love to write, but also beautiful, art-centric, aesthetic, social objects,

• 1:23:29Jonathan Fields?

  getting back to photography and printmaking, which are other maker passions, painting and doing large-scale design work and making music, not for any reason, except that it's who I am. And that feels incredibly freeing and joyful, too, and vision. And will I at some point find maybe interesting ways to create something bigger around it? Economic structures to support it? Maybe. Lots of ideas already floating around in my head because as we've already established, that's the way I'm drawn. And you may even see some come to life in the fairly near future, again, as experiments. But the bigger awakening is this, whether I do or don't find ways to, quote, "fund

• 1:24:11Jonathan Fields?

  these things," they still need to happen because when I make things, I am, plain and simple, alive. So that's been a huge homecoming for me. Another one is about really redefining work and success on my own terms. Right? This insight has been kind of around the need to redefine success in the context of work. It's so easy to carry old metrics of success with us. Titles, incomes, levels, audience size, number of projects completed, reviews, blah, blah, blah, blah, blah, blah, blah, blah. And just because I've literally worked for myself, built my own companies and endeavors for the better part of my adult life now, doesn't mean I'm immune to this.

• 1:24:54Jonathan Fields?

  For years, I unconsciously measured myself by how big of an impact I was making in a visible sense, in a financial sense. How many people did we reach? What's the next big project? Am I staying, quote, "relevant" in the fast-moving media landscape? What are we earning? How much can we give or give back? These questions can drive you to do incredible things, but they can also drive you out of your mind. When I stepped back, I realized that I was at least in part chasing some of those things out of habit or fear. Fear of maybe not mattering, fear of wasting my talents, fear of letting people down if

• 1:25:33Jonathan Fields?

  I didn't keep leveling up, fear of not being able to actually take care of providing some sort of sense of security and stability and safety. And through my two by 20, I've really deliberately paused that chase to ask, what truly matters to me in my work now? And the word significance, it kept bringing me back to meaning. Was my work deeply meaningful to me regardless of how it looked from the outside? So when I talk about significance, I'm not talking about necessarily significance to others. I'm talking about, does it matter to me? And I had to face the fact that certain aspects of my work that quote, looked successful externally,

• 1:26:18Jonathan Fields?

  they weren't feeling all that meaningful internally anymore. They just didn't matter all that much to me anymore. That was a tough awakening. It meant that I might step away from things that people know me for, things that are quote, successful. It also meant possibly disappointing some expectations. But the breakthrough was giving myself permission to prioritize my inner alignment over external approval. So what does success look like to me now? And again, it's a bit of a moving target and it probably will be for a long time. But right now it looks like creation, simplicity and service intertwined. It's having a work life that is spacious enough to not crowd out my health or family.

• 1:27:02Jonathan Fields?

  It's focusing on projects that I would do even if no one paid me because that means they're driven by genuine curiosity and passion and expression and alignment. It's also measuring impact in depth, not necessarily breadth, which is also a bit of a shift for me. If something I create helps a smaller number of people in a truly profound way. And when I use the word help, by the way, even if it just touches or moves them, that's more satisfying than something where maybe I have some sort of superficial thing that is going out into the world and it's reaching millions. For example, if I end up maybe coaching or advising or mentoring

• 1:27:45Jonathan Fields?

  a handful of individuals over a window of time in their own 20 by 20 transformations, and that changes the trajectory of their lives, that might be more fulfilling than getting millions of downloads or views. Or if I documented a creative journey, invited maybe smaller community of people to come along, then distilled it into beautiful artistic social objects and limited edition art house books, large scale prints, you know, with maybe only a few hundred, a few thousand of these things ever being created and interacted with, rather than the mass scale that I have come to operate at, that would still be deeply nourishing to me, maybe even more so. And this has been a shift from my earlier mindset.

• 1:28:29Jonathan Fields?

  I still value scale and reach. I mean, I'd love to do both depth and breadth, but I've realized that I won't chase breadth at the expense of depth. So one concrete realization, I don't actually want to build a big new organization or venture right now, even though I'm tempted. There is a voice that sometimes pops up and I see something, I'm like, there is something that I could do, that I know I'm skilled to do, and there's a need in the marketplace. But I'm at a point where I'm like, but should I? Probably not. Just because I can doesn't mean that I should. And in the past, I might have automatically thought, I need to scale this into something big, even if I start something small. I need

• 1:29:12Jonathan Fields?

  to build the brand so I can impact millions and potentially even exit, like I've done with a number of past ventures. But big often conflicts with simplicity, with ease, with lightness, with joy. I've done big. I know what comes with it, staff, systems, complexity. I'm more interested right now in lean, honest, and focused. In small experiments, tight teams, agile changes, this was crystallized by that moment. I nearly overbuilt even the newsletter idea striving to grow to hundreds or thousands or millions and build a suite of offerings, caught myself and thought, yeah, they're saying impulse to maximize and monetize. What if instead, I just let it be intimate and be good and be true?

• 1:29:56Jonathan Fields?

  And that moment kind of symbolized a larger shift. I'm learning to trust that doing less, but more meaningfully, can actually yield not just a happier life, but also plenty of quote, "success." And yes, even financially or reputation wise, if that's something that continues to be really important, the difference is that becomes a byproduct, not the central goal. It's funny, I talk about how to live a good life and the three buckets and all these principles. And I genuinely believed them before, but through this process, I've had to kind of relive them all at a deeper level. It's one thing to intellectually know, don't let the contribution bucket dominate at the expense of others.

• 1:30:38Jonathan Fields?

  And actually another to make the hard choices to ensure that it doesn't, or to ensure that we're filling it in a way which is genuinely holistic and harmonious. And I had a few gut check moments where I had to turn down opportunities that would potentially refill the contribution bucket from a reputation or economic side, but empty out who I was and the meaning side, or maybe really drain my vitality or connection buckets. And saying no is hard, but also empowering. Every time I honored my new definition of success, I would feel assertive integrity, like I was becoming more whole. And maybe the final realization here is around facing fear and uncertainty with compassion.

• 1:31:23Jonathan Fields?

  Let's talk about fear, our old friend fear of change, of failure, of the unknown. You think that since I literally wrote a book called Uncertainty a dozen years ago, about leaning into the unknown, I'd have this part down pat. And in some ways, yes, I have a lot of tools for dealing with fear and uncertainty and the unknown. And I've gotten much better than I used to be, but I'm also human. And when it came to really actually shaking up my own life, fear absolutely reared its head. In the early days of the two by 20, I had a subtle fear, what if I do all these experiments and still don't know what I want for the next 20 years? I mean, what if I come out quote, "empty-handed," so to speak?

• 1:32:07Jonathan Fields?

  Also, what if I really discover that what I want requires really disruptive changes? Like, walking away from current endeavors, or moving, or something drastic? Am I prepared for that? There was even a fear of, what if I publicly share this journey, and then it doesn't work out? Will I just look foolish, like a failure? And one of the biggest fears underneath was a fear of also wasting time or talent. At this age, you become acutely aware that time is finite. Devoting two years to experimenting felt right to me, but the fearful part of me whispered, what if you waste these two years and come up with nothing to show?

• 1:32:47Jonathan Fields?

  You could have written two more books in that time, or doubled down on the known successful stuff. This is where the concept of experiments really helped me reframe. By telling myself, this is intentional R and D for my life, I treated it as valuable in its own right, not as a waste or a detour. I had to frequently reassure the anxious part of me. Learning is never wasted. Growth is never wasted. If I do something, and then learn nothing and don't grow from it, which is pretty much impossible if I pay even the smallest attention to what happened, maybe that's a waste. But that's not what's happening here.

• 1:33:29Jonathan Fields?

  Even if some experiments lead nowhere, knowing what doesn't fit gets me closer to what does. So I also confronted a fear of uncertainty, in the sense of not having a clear, maybe, identity for a while. When you step back from what you've always done, there can be a void. People ask, so what are you focusing on now? And if we'd feel a little bit vulnerable, say, um, not entirely sure. I'm still doing the big things that I'm known for to a large extent, but I'm also trying a bunch of things. Our society loves clear answers and elevator pitches. And for a period, I was deliberately living in the gray. That was sometimes uncomfortable.

• 1:34:12Jonathan Fields?

  I had to remind myself that not knowing is not a sign of failure, it's actually a necessary phase of creativity, growth, and change.

• 1:34:23Jonathan Fields?

  In fact, uncertainty is the fertile ground where all possibility lives. I know this intellectually, but I got to practice embracing it emotionally. I cultivated patience with open questions, almost like sitting with a meditation mantra. When my brain wanted to lock in something prematurely, just to have the answer and just say like this, this is solid, this is what I'm moving forward with, I gently say, wait, dude, just chill, stay with the process. More will be revealed in due time. And it was again and again, as I stayed in it, in the space of uncertainty and tried more things. And fear also showed up in some specific experiments.

• 1:35:06Jonathan Fields?

  For instance, when I decided to return to public writing, I had the fear, what if no one cares about what I have to say anymore? I was starting literally from zero, entirely new platform. What if my ideas aren't quote, original enough, or my story is meaningful enough? Or in the art experiment, you know, like even before writing, I had comical fear. What if I totally suck at painting now? And I just confront my lost youth or, you know, metal smithing, like what if I absolutely suck? Which I did and do, but that will change. But by that point, I had flexed my courage muscles enough that I can answer back. And what if you do suck? Then you suck, but you'll likely enjoy it anyway. And no one needs to see it.

• 1:35:50Jonathan Fields?

  You're doing this for you. And as I began taking those metal smithing classes and total newbie and like slowly stepping back into visual art making and design. Are my chops, you know, like really good? No, but is the stuff that I've done in the past coming back really quickly? It is. And is the stuff that's brand new to me? Something that just feels amazing, even though I'm a total newbie? Yeah, it does. When I let go of having to be the expert in the room and just reconnect with the fact that I'm finding new ways to lead with my maker impulse, everything falls into place and I come so fully alive.

• 1:36:31Jonathan Fields?

  I've really learned to talk to my fear with a lot more compassion and humor. Instead of making fear an enemy, I treat it as a somewhat misguided friend trying to protect me. Thank you, mind, for trying to keep me safe from embarrassment or failure. I've got this. Even if it goes south, I'm going to be okay. And I will learn something. There's a particular insight about fear that came to me from failed afternoon hiking, actually, in the coaching program experiments. So sometimes we fear making a change because we imagine we're stuck with it if we choose it. But through this process, I also learned that almost everything is adjustable.

• 1:37:15Jonathan Fields?

  I tried afternoon hikes. They didn't work, so I adjusted to mornings and back to afternoons as the season changed. I enrolled in training programs. I didn't like them. I tried another, same result. So I didn't pursue that approach to what felt like a potential fertile option, advising in that same way. I ran a bunch of experiments with my health. All gave me new insights, whether I stuck with what I tried or not. Again, remember, life without chocolate? Hmm, not a good experiment for me. The world didn't end in any of those cases. This seems obvious, but think about how often we avoid trying something because we're afraid it won't be right for us. We forget we have the agency to course correct.

• 1:38:00Jonathan Fields?

  Realizing I can say no or change direction at any point took a lot of the pressure off making the, quote, "perfect" choice. It made me braver to try things that had been on my curiosity list for a while because I knew it wasn't a life sentence. It was just an experiment. Emotionally, learning to live with uncertainty and fear has made me more resilient and open. I don't get as easily thrown by not knowing. I've become more comfortable in that in-between space where a lot of magic can happen if you don't rush to close it. And this is something I deeply want to share with others because so many of us abandon dreams or changes out of fear. If we can shift the mindset to one of playful experimentation, fear loses a lot of its teeth.

• 1:38:45Jonathan Fields?

  It becomes, if not fun, at least less paralyzing. And you realize, hey, I'm still here. That fear came and went like a wave, and I am actually making progress. And that brings us to a realization around evolving identity and purpose. So a significant realization has been seeing my identity evolve and being okay with that. For a long time, I was Jonathan Fields, the Good Life guy, or the author, or the entrepreneur, or the founder. And those labels, they're fine, and they're not entirely untrue. They are a part of me, but they can also box you in, or in this case, me in. This journey has helped me expand my sense of identity.

• 1:39:30Jonathan Fields?

  I can now comfortably say I'm also an artist, a teacher, a student, a mentor, a hiker, somebody who loves people around him and loves nature. The point is, I contain multitudes, as we all do, and we don't have to be just one thing for the rest of our lives. It seems obvious, but many of us subconsciously believe, I chose this path, I guess this is just who I am now. This is my, quote, "lot." I have actively broken that notion for myself. Now I see my identity as more of a mosaic, pieces, old and new, growing and changing. Some pieces from earlier in life, like painter, artist, maker, or blogger, are being added back in. Some pieces may fade. Maybe I won't be a CEO, or producer, or anything, who knows?

• 1:40:15Jonathan Fields?

  And some new ones may be forming, maybe advisor, mentor, publisher, really become part of who I am moving forward. And this ties into this word, "purpose." I used to articulate a sense of purpose as something like, you know, to help people live more meaningful, connected lives through writing and teaching and all this other stuff. And sure, that still resonates, but I probably tweaked that a bit now. You know, like, having a sense of purpose in this next season is more around to live my life as fully and authentically as possible, and to help others do the same in whatever ways I can. The first part is important. It's not selfish, it's actually the foundation.

• 1:40:58Jonathan Fields?

  I realize that by courageously living my own questions and dreams and sense of self, I become a better guide for others. It's the idea of embodied wisdom, which literally is the seat of everything in Good Life Project, finding teachers who embody the wisdom that they share, versus just, quote, "intellectual knowledge." So I see it as part of my purpose to be the experiment, not just run experiments, to walk the talk of the good life, even as I talk about it. And the second part of purpose, helping others, also has taken maybe a more intimate flavor. Previously, it was through broad context and enterprises. I suspect in the next phase, maybe it'll be more of a mix, still broad reach through things like podcasts

• 1:41:43Jonathan Fields?

  and books, but also direct reach through perhaps more intimate advising or small group experiences, aesthetically oriented, social objects, and crafting containers for intimate, shared, creative journeys, or teaching, as I mentioned. So my purpose is clarifying into something like, be true, trust that it's enough, and let that be a catalyst for meaningful change. Whether that's change in an individual over a coffee, or change in a reader through a book, change in an individual who's moved by some visual work, or change in a student over a semester, or just my own freedom to allow myself to change. And also to savor a life that I'm living while I'm at it. To laugh, to love, to create, to enjoy this

• 1:42:28Jonathan Fields?

  ride, to fully express who I am and not hide anymore. Purpose doesn't have to be this somber, grandiose statement. In fact, one of the big insights is that joy itself can be a purpose. Creation for its own end can be a purpose. Spreading joy, being creative, living joyfully, that's as worthwhile as any other purpose. After all, why do any of us seek meaning or success? Ultimately, I believe, because we think it will make us happy or fulfilled. Joy is both a means and an end. And one more identity shift here. I embraced being, this is gonna sound so weird, an elder member of Generation X in a new way. Right? Might sound really random, but it's come up so many times during this

• 1:43:13Jonathan Fields?

  project, when so many people who are a similar age as me are like, that, what you're doing right now, that's where I am. And I don't have a lot of other people that can have these conversations with that, I can deepen into that, understand the history and the context and the references.

• 1:43:29Jonathan Fields?

  I was researching societal trends. I noticed how my generation, I'm Gen X, generally folks in their 40s to late 50s, often get labeled as the forgotten middle child between Boomers and Millennials. And indeed, we are. We have been the invisible generation for most of our lives. The figure it out on your own generation, the don't expect too much generation. I mean, hell, our rally cry movie when we were younger was the iconic grunge-themed reality bites. Gen X has its own existential things going on, often caring for kids and aging parents, often at a pivot in career, et cetera, and not a lot of cultural spotlight

• 1:44:09Jonathan Fields?

  or serving headed in our direction. And I felt this strong identification, like, hey, that's me and my peers, and we have unique struggles and gifts, and nobody's really paying attention to that. It dawned on me that perhaps part of my emerging purpose is to be a little bit more of a voice or support for my generation as we navigate midlife and beyond, to give words, language, expression to what so many of us feel, what we've navigated, but have never fully, truly expressed, or even a little bit. And one of the things I've been told by so many, so many amazing people over the years, who've welcomed me to speak or read what I've written, is that in some way, shape,

• 1:44:53Jonathan Fields?

  or form, I helped give language to what they've been feeling, but have never been able to clearly articulate or share. And to the extent that that's true, I love being able to play a part in letting so many people who felt largely invisible for so long finally feel seen. We are a smaller cohort, but we're at this critical juncture of life. This realization is still percolating, but I mention it because it gave me another lens of identity, not just Jonathan, the individual, or the other things I talked about, but also, frankly, Gen X Jonathan, who can maybe help bridge wisdom between generations. It's a more collective identity, which feels meaningful to me. And in essence, I'm coming to see the next 20 years, not as some fixed identity or career path, but

• 1:45:38Jonathan Fields?

  as this rich landscape, where I'll play many roles, sometimes the creator, sometimes the guide, sometimes the student, sometimes a friend, and that's beautiful. Sometimes the maker. I often picture my 80-something-year-old self and ask, what would make him proud or satisfied, looking back? And the answers are rarely, oh, he made a lot of money, or he was really well-known. They're things like, he loved deeply, he never stopped learning, lifted up others, he made beautiful things that moved people, he experienced the wonder of life fully. That perspective has been the ultimate guide. It cuts through just all the noise. And if an experiment or opportunity wasn't contributing to the possibility of that

• 1:46:22Jonathan Fields?

  kind of reflection, I would reconsider it. And that brings us to an invitation here. So I have shared a lot about my journey, the concept, the experiments, the hits and misses, the inner journey. And now I want to turn the lens toward you, the listener, maybe the viewer. You might be thinking about your own life as you hear this. Maybe you're at a pivot or craving something more. Maybe you feel a whisper, like I did, asking, is this what I want for the next season of life? Maybe even focusing particularly on your work. And if so, I'd invite you to consider embarking on your own version of your own two by 20, or make it a one by 10, or a five by 30, whatever it is. The numbers

• 1:47:06Jonathan Fields?

  aren't magic, it's the spirit that counts. You don't need to wait for some perfect time or permission. You can start with a simple commitment. I'm going to run a life experiment. It could be as small as trying a new morning routine for a month to see how it affects you, or as big as exploring career change over a year, or maybe longer. The key is to approach it with curiosity and playfulness. And remember, experiments have no failure, only data. That mindset is deeply liberating. It allows you to try things without the paralyzing fear of making the quote, "wrong" choice permanently. If something doesn't work for you, just adjust and try again. If you're feeling inspired, or even just curious about

• 1:47:48Jonathan Fields?

  this idea, I'd love for you to treat this podcast, this conversation, not just as my story, but as a prompt for yours. You might journal about it, or talk it over with a friend or partner. What might my two by 20 look like? If you could ask a guiding question for your next phase, what would it be? Mine was about simplicity, significance, and joy. Yours might be about adventure, or love, or impact, or maybe security, creativity, or community. There's no right answer. It's about what themes speak to you. I'd also want to extend a bit of an invitation for maybe more direct engagement, and maybe something that would see our experiments coming together. Earlier I mentioned I was exploring more one-on-one or small group mentoring as

• 1:48:30Jonathan Fields?

  a possible part of my next season. Well, I decided to dip my toes in that water as a part of my own 20 by 20. I'm not announcing a big coaching program or anything, keeping it simple, remember? Like, I decided not to do that stuff, but I'm gonna do two things. One, I'm gonna open up a small number of times to start working with just a few individuals in individual or potentially even small group coaching mentorship capacity, specifically around crafting and navigating their own two by 20 or similar journeys. Think of it like a guided incubator for personal change. I'd help you formulate your guiding question,

• 1:49:14Jonathan Fields?

  design the container for your two by 20, run experiments in your buckets, and be there as a sounding board, and if needed, accountability partner as you explore and grow and learn, and then create. And I'm approaching this very playfully. It's as much a learning experience for me as it would be for you in a way. Coaching others through their two by 20, through your two by 20, will be one of my next experiments in the contribution bucket to see if this is something that energizes me and creates real impact for people and for me. And second, I've been talking with my team, and based on the incredible response that we've had this whole two by 20 concept, we're looking at hosting an intimate, kind of high-touch,

• 1:49:54Jonathan Fields?

  three-day-ish, in-person, two by 20 retreat in the fall. It'll be a chance to gather with me, with a couple of folks in our team, and a small number of just like-minded people at a similar point in life. This will not be a big event. And to begin the process of designing your own next season. So if you're interested in either, there will be a link at the top of the show notes to learn more. And if it feels good, you can go ahead and check it out and explore what

• 1:50:28Jonathan Fields?

  Working together or joining us on retreat might look like. So if, as you listen today, you felt a little spark, a little, oh, man, I want to do something like this in my life. And if you'd like some guidance or fellow travelers who are a bit further down the road and maybe just traveling alongside of you, consider this a personal invitation to work, to play, to learn and grow together and to maybe craft a pretty stunning next season of work, life and love together. I genuinely believe that we learn so much from each other's journeys. I know hearing other people's pivots and reflections has given me courage in the past. And if my journey can do that for you in any meaningful way, I'm just deeply honored and I would love to hear about yours. So don't hesitate to write in with your own experiments or epiphanies.

• 1:51:13Jonathan Fields?

  Who knows? Maybe future experiment will be us compiling some sort of beautiful collection of shared stories of people moving through their own profound transitions and sharing the patterns and stories, particularly insightful and beautiful way. It could become maybe a movement of sorts, but again, not going there, not getting too deep into the let's build this into something bigger type of mode. I want to keep it beautiful, intimate and meaningful for you. And as we come to a close, I also want to reiterate something important. You don't need to overhaul your life to get value from this approach. Even if you stay in your job or your role in your city with your responsibility, you

• 1:51:55Jonathan Fields?

  can still infuse this spirit of two by 20 experimentation and renewal in small ways. Maybe it's dedicating one evening a week to that passion project or having deeper conversations with your partner, using those three buckets as prompts, or maybe trying a new workout or spiritual practice. These little practices or experiments can rekindle a sense of agency and excitement about your life. It's like turning on a light in a room that was dim. Suddenly you see possibilities where before there were routine and habits and maybe not a whole lot of joy or feeling.

• 1:52:32Jonathan Fields?

  And I also want to acknowledge, if you're listening and feeling, well, that's nice for you, Jonathan, but I have X, Y, or Z constraint. I get it. Not everyone can just redesign their work or take on multiple changes at once. Responsibilities like caring for family, financial pressures, health issues. Life is real and often challenging, especially now for a lot of folks. But that's exactly why I believe in the power of micro experiments. You can start right where you are with whatever you have. Maybe your two by 20 is more internal, two years to double your self compassion, or two months to try new practices to help with anxiety or stillness. The scale can shrink or expand to fit your reality. And remember, this is not a competition or a comparison game.

• 1:53:16Jonathan Fields?

  Your journey will look different from mine, and that's how it should be. Success in this is simply that you feel more connected to yourself and what makes you come alive. So as for me, my two by 20 project is ongoing. I'm just starting to move into what I call the build phase, where some of the things that I've learned will turn into more concrete new chapters. I will keep sharing as I go because I've come to really enjoy living just a bit more out loud with this, knowing that it might help others. It's funny, I started this as a almost secret project, and here I am spilling the tea on all of it. Life is kind of beautiful that way. When we share from the heart, I feel like it just creates these ripples that connect all of us. And I want to leave you with an image.

• 1:53:59Jonathan Fields?

  Imagine yourself two years from now. It's a sunny morning. You wake up feeling good. The details of your life may not be drastically different, or maybe they are. Maybe you're in a similar home or job, maybe did make a bigger, more meaningful change. But the key is, inside, you feel more you. You have crafted your days and commitments in a way that brings you energy rather than takes it from you. You're working on things that matter to you. You're taking care of your body and your heart and your mind. You're connected with people you love. There's a sense of alignment that your outer life is catching up with your inner identity and aspirations.

• 1:54:42Jonathan Fields?

  You might smile and think, I'm so glad I experimented and listened to myself back then. That's the picture I hold for myself and for you. Not a perfect life, but a good life, a true life. So thank you for listening and joining and walking alongside me for this adventure. And again, if you're at all curious about working together, joining me on retreat, or in some way exploring your own 2x20, check out the link in the show notes and see if it speaks to you. Until next time, I'm Jonathan Fields and this is Good Life Project. This episode of Good Life Project was produced by executive producers Lindsay Fox and me, Jonathan Fields. Editing help by Troy Young. Christopher Carter crafted our theme music.

• 1:55:24Jonathan Fields?

  And of course, if you haven't already done so, please go ahead and follow Good Life Project in your favorite listening app or on YouTube, too. If you found this conversation interesting or valuable and inspiring, chances are you did, because you're still listening here. Do me a personal favor, a seven-second favor, share it with just one person. I mean, if you want to share it with more, that's awesome, too, but just one person even, then invite them to talk with you about what you've both discovered, to reconnect and explore ideas that really matter, because that's how we all come alive together. Until next time, I'm Jonathan Fields, signing off for Good Life Project.

• 1:56:20Jonathan Fields?

  Today's episode is sponsored by NerdWallet Wealth Partners. Are you on track for financial independence? If you're on track, the same way you're getting back to the gym, as in, maybe next year, then this one's for you. NerdWallet Wealth Partners offers free tools for high earners who'd like an actual answer instead of a vibe, like their calculator that estimates if you're on track for financial independence. Plug in a few numbers to see how your savings path may support your goals. Think of it as a fitness test that you can take sitting down. Or their wealth-building checklist for high earners. It's a step-by-step guide for prioritizing your dollars once you're making six figures. And if you still have questions, you can connect with one of their financial advisors who specializes in working with high earners in their 30s and 40s. Good news, this is one workout you can actually finish.

• 1:57:04Jonathan Fields?

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