285:How to Rebuild Your Life From Scratch by Following What Feels Alive with Jonathan Fields

On the outside, Jonathan Fields had it all. He was a successful New York City lawyer pulling in six figures, wearing tailored suits, and working on billion-dollar deals. But on the inside, he was quietly falling apart. Working 100-hour weeks and living on caffeine and takeout had taken a toll, and a sudden health crisis forced him to reckon with a hard truth: the life he’d worked so hard to build was slowly destroying him.

That wake-up call didn’t just spark a career change—it sparked a full-on reinvention. Jonathan didn’t just switch jobs; he left law altogether to become a $12-an-hour personal trainer. Everyone thought he was out of his mind. But that decision opened the door to something far bigger: a journey into entrepreneurship, wellness, and ultimately, his life’s work.

In this Plot Twist episode, Jonathan shares the raw truth behind his pivot from law to wellness to founding the Good Life Project. He opens up about ego, identity loss, starting over in your thirties, and why success often comes disguised as failure. You’ll hear how his Sparketype framework was seeded in the rubble of 9/11 and how teaching yoga reconnected him to a sense of purpose he hadn’t felt since childhood.

If you’ve ever felt like you were climbing the wrong ladder, or wondered what it might be like to trade prestige for peace, this episode is for you. It’s a story about trusting your gut, letting go of expectations, and building a life that actually feels good on the inside—even if it doesn’t make sense to anyone else.

Transcript

JF: “ I literally had the job that so many of us had worked so hard to get. And it was not an easy job to get. And there was a lot to it. And so when I walked away, especially not to go to another job or not to become general counsel there, not to go in-house with the client, which is what most people do if they leave and serve of like a mid-level associate which is what it was, but literally like my departure memo, which got sent around the firm 'cause every time someone left, he sent a departure memo around. It effectively said, Hey, I'm leaving the law firm, but I'm also leaving the practice of law to go lead people up mountains and take them mountain biking and play with them in the park. And the hush talk from the people who were at my level in the firm was not kind.”
 
 

[INTRODUCTION] 

 Hey, it's Light. Welcome back to the podcast. So on the outside, everything looked great for Jonathan Fields. He was a high powered lawyer in New York City making six figures, rocking the fancy suits, checking all the boxes of success. 

But on the inside, he was barely holding it together. Years of overwork and stress caught up with him until a sudden health crisis forced him to stop and rethink everything.

And in this plot twist, Jonathan shares the unlikely pivot that changed his life. He left law to become a $12 an hour fitness trainer, and that decision led Jonathan to become a bestselling author, a major podcast host whose show I've been on a couple of times, and the community builder that he is today. 

In this episode, you're gonna learn how to recognize when success is quietly wrecking your wellbeing, how to navigate identity loss in big transitions, and why starting from scratch might be the smartest move you can make. 

We're gonna begin with the moment that Jonathan's body gave out and how that sparked the reinvention of everything that came next. Let's dive in.

LW: You had some immune problems, or something like that, right? You're 30, 31-years-old? What was that like? Because now, I'm sure you're making your six figures and you're seeing all this money, but how do you feel about yourself inside and physically and mentally?

JF: Yeah, I'm crashing inside hard. You're right, I'm making my six figures. I'm wearing my really fancy suits. I've got the business card that everybody wants.

LW: Do you still have the gym this body? You still had that six-pack?

JF: No. I'm a physical wreck at that point. Because I'm not leaving the office. I'm basically working a 100 hours a week. Because when you get paid, when I was getting paid, essentially, you're turning your life over. Especially in the early days. That's, you earn your chops. No, within a matter of weeks, I was put on a deal. I barely went home for probably three weeks. I was living on chocolate, caffeine, and takeout. I was a physical and emotional and psychological and probably, cognitive wreck. This is just what we did. It's a day in the life.

You do it in no small part. Either because you love it, which wasn't me, or because you got your eye on what you hope is the characters being dangled, which is partnership 10, 12 years down the road. I could care less about that. I ended up in such bad shape, that I was doing this one deal. Two, three days before, I just felt this pain in the middle of my body. I just ignored it and it got worse and worse and worse and worse, until I could barely breathe. I was doubled over. But I'm still working and nobody's paying attention, because everyone's in their own hazy space.

We hit the button on the deal. I went home. I went straight to my doctor after passing out for a little bit. Then, he looked at me and turned a little bit white. He's like, “There's something large inside of you that wasn't there a few months ago when I did your physical.” Took me to an infectious disease guy. Within a matter of hours, I was checked into the hospital and had emergency surgery, because had a huge infection that had mushroomed into a baseball size thing in the middle of my body, and ate a hole through my intestines from the outside in.

I think, the assumption back then was, I think, you probably had an infection brewing in you for a while and your immune system basically, had nothing left, because your body was in such bad shape. It just mushroomed into this thing. Thankfully, it all went really well. I knew at that point, I was on my way out. I didn't leave for the better part of another year, because I wanted to figure out what the next step was going to be.

As I started to realize I was going to go back into the world of entrepreneurship and movement and well-being and human potential, I also realized that I was going to start over, and very likely, either make nothing, or make a very small salary, especially compared to what I was making. I was working almost entirely just to make plans and bank money and give myself a cushion for the next step.

LW: This is the craziest part of the story to me. Because I think it would just be unfathomable for many people to leave a high-paying job, where you're literally toying with billions of dollars to becoming a trainer at a gym for $12 an hour.

JF: Yeah. That hurt. It hurt my ego more than anything else.

LW: Did you get pushback from your colleagues, your friends, your parents, and anybody? Who are your supporters? Who is cheering you on? Who's pushing back, that made you really rethink this plan?

[00:39:08] JF: Yeah, so my wife. Our relationship was very young then. Stood by me. We started dating when I was just graduating law school. She starts a relationship with a rising lawyer in New York world, and financing, this and that. All of sudden it’s like, “Ah, he’s 12 bucks an hour, wearing running shoes, tights and a ratty old t-shirt and playing with people in Central Park.”

She was there for me. My family was there for me, too. I don't think they understood what was going on with me, but they gave me space to work it out. They weren't pressuring. They weren't like, “You're making a horrible decision.” Again, it was one of those moments where when I reflect on so many other folks, I was in such a fortunate place in that my parents, who I love and I'm close to, did not just really place all of these things expectations about what they felt was the appropriate decision for me on me.

They were like, they told me what they thought, but they were also, liked your life. Do what you got to do. That was a great gift. Sure, a lot of my friends who I went to law school with could not understand, because I literally had the job that so many of us had worked so hard to get. It was not an easy job to get. There was a lot to it. When I walked away, especially not to go to another job, or not to become general council there, or not to go in house with the client, which is what most people do, if they leave in a mid-level associate, which is what it was.

Literally, my departure memo, which got sent around the firm, because every time someone left, you sent a departure memo around. It effectively said, “Hey, I'm leaving the law firm, but I'm also leaving the practice of law to go lead people at mountains, and take them mountain biking and play with them in the park.” The hush talk from the people who are at my level on the firm was not kind. The private notes that I got from people, like senior partners in the firm, which basically said, “God bless. Go do this. Do it now.” That was really strong validation, because these were the people that all the younger people were working to become. Then some of those people were saying to me, “You know what, man? Go do this thing now. This is your choice.”

I’m like, I don't know if it's going to work or not, but this is the moment to try. I think that helped bolster me a chunk. It was still, there was a minute of really wandering in the dark and wondering what I was doing. In certain days I’m being like, is this in any way defensible? I had planned for it. I knew I was going to go into a space, uncertain and you had to learn something from the ground up. I went to the fitness industry. It was my first step out, because I think, it was being so somatically-oriented, and having abandoned it during my time in the law, I wanted to get back to it personally. Also, I was really curious about the business, and what was working, and what was not working.

I just had a really strong sense that there was a lot that was not working, and there were a lot of people that were not being served, and that there was a better way to do it. I want to learn it from the ground up. I'm sure, I could have found my way into a management level position in the industry and started there, but I wasn't interested in that. I want to learn what was happening on the fundamental point of contact between one human being and another, and on the floor of the gym, not too dissimilar to the floor of a dance club. There's a lot of threads that weave together.

There's this big social dynamic. It's humanity. It's all different parts of humanity, unfolding. I wanted to learn that. I was like, okay, doing the $12 an hour thing just to learn this from the ground up. My ego took a little while to be okay with it.

LW: You're also not just a trainer. I mean, you've been exposed to a world that most people will never know even exist, but they feel the effects of it everyday without realizing it. You're now thinking like a venture capitalist, and you're thinking like a lawyer. You're bringing all of that with you, so it's not just, you learn how to teach people how to do this exercise. It's like, let me see how this business is built, and how it grows, and how we can do it more efficiently and all of that.

JF: For sure. I mean, my time in the SEC, we spent a lot of time deconstructing businesses to understand where things went sideways. That blended with my own experience, with my own businesses. It allowed me to see a lot of different things. Stepping into the floor as a personal trainer with a background in law and finance, when a lot of the clients who can afford that level of service have similar backgrounds, it actually gave me a really interesting competitive advantage. Because I can have conversations and rapport with many of my clients about things that were really unusual for somebody.

LW: They must have been shocked that you knew some of these issues.

JF: Yeah, totally.

LW: Then working at the gym.

JF: I’d start talking to them about the markets and what I thought was a sophisticated way. I have no idea if it really was or not. Yeah, you would see the eyebrows raised and their head would cop and be like, “Wait. What? You know this stuff?” Because we all make assumptions about people.

LW: I want to flash forward a bit. We don't have to get into so many details around what happens next. You sell your wellness business. You leverage that a little bit later, at a very peculiar time. I would say, looking at your whole trajectory, you have a knack for timing. You have a really good knack for timing. This is just, talking about this first example.

JF: Yeah. I don’t know if it’s good, but there’s definitely a knack.

LW: No, it is good. It is good. We'll tie that together in a minute, but talk about leasing that floor of the building and the circumstances around that.

JF: I had opened my own facility in the fitness world, and grew for two and a half years and sold it to some investors, and then I got curious about the yoga world. I had developed my own practice. It’s very, very young in the practice. It actually started with breathing. Because as a lawyer I was so stressed out, that I needed something to help down-regulate my system really quickly. I would find myself hyperventilating on adversarial calls and I was like, “This is not okay.”

I started with Pranayama, Then I really became attracted again, the somatic side, the Asana and the movement. I got curious about the business. That’s just the way my mind works. I scan the universe in New York, and I was like, oh, there's a lot of great studios back then. I mean, it's nothing like it is now. Also, a lot of them were steeped in certain parts of tradition that were very off-putting to people who are not yet a part of the traditions.

I want to create something that was different, something that was accessible. I got this idea in my head. I'm walking by a space a couple blocks from where our apartment was, then in Hell's Kitchen, New York. It looked literally, it got bombed out floor in a 115-year-old building. I looked inside. I was like, “Oh, we could turn this into something really cool.” I signed a six-year lease for that floor in a building three blocks from our apartment, new home, married, three-month-old baby. The date I signed the lease was September 10th, 2011. A day before 9/11.

LW: 2001.

JF: 2001. Yeah, sorry. Yeah, woke up to the awfulness on every level. That was 9/11. In my city, in New York City. At least one person who was a friend who didn't come home that day. It was a really powerful moment for me. Because it really brought home the fact that we have no promises. Immediately, I was wondering who do we know who's in the towers, because pretty much every New Yorker knew somebody.

Then I was like, “Am I really going to launch a business into this? I got a family. I need to do what I can to take care of them emotionally, psychologically, and financially, especially then.” Knowing that I knew somebody who didn't come home, and the devastating effect it had on their family, it was one of the things that along with a bunch of other just emotions and feelings, experiences, really reminded me that we just have one pass through. I want to make the best use of my time.

To me, opening a business that was not just a business, but was a place of community and healing and breath and movement, was the thing to do, as scary as it was. I mean, it's scary to launch a business in the best of times. It was terrifying to launch it then. But we did. Eight weeks later, we launched the center.

I mean, people were walking around then, literally, wandering around the streets in days. Complete and utter days, nobody knew what to do. People just wanted to do something to help and to feel better, but nobody knew what to do. The smoke still filled the air, all the way up to Midtown. It was a very bizarre, surreal, sorrowful, painful moment. To be able to create something where we could bring people together in a safe space, and join them in movement, join them in music, join them in breath, join them in just being allowed to feel in community was astonishing. We went forward with that.

Because of that, we grew into a big, successful community and also a successful business on the backend of that. Yeah, it's a really powerful experience. Again, on the one hand, you could say, right moment, right time. On the other hand, you could say, absolute not right moment and not right time, because would have been a whole lot easier to open something in the best of times, with good economics and doing all sorts of things. In terms of having meaning and knowing that we were doing something – we're playing a part that was much bigger than what I ever conceived. It was really powerful experience that has really stayed with me in a lot of different ways.

LW: I was living in New York at the time, and I was – no, it was about three, four years into my yoga practice at the time. I remember, there only being a handful of yoga studios. There's OM, there was Jivamukti.

JF: Jivamukti. Yeah.

LW: Maybe a couple of others. I was going to Equinox a lot, taking their yoga classes. I remember when Sonic opened, actually. I feel like, that experience, it reintroduced New York City to community, to connection with one another. People were all of a sudden, very friendly with one another. I think, for the purposes of building a community, that you really can't get a better time, then people actively seeking out, I need to know who my neighbors are, because I was in their living room during 9/11, and I even then, never met them before. We just started talking and asking each other how we were doing and things like that.

JF: It's interesting, because reflecting now, my experience of that moment was the six months or so following it, I mean, I was in my own altered reality. I was launching a business and trying to be there for my wife and baby girl at that time. Also, there was this profound sense of brotherhood and sisterhood and fellowship, and just wanting to take care of each other that lasted for three, four, five, six, seven months.

Upon reflection, I've since learned, while that was my experience, that was not in fact, the universal experience that if you didn't look like me, if you were a sick, or if you appear to present in any way, shape or form to be Middle Eastern, that you became an instant subject of violence, and of ostracism. My experience of profound, both sorrow, but then also fellowship, and open arms and shared humanity, I've learned since then, for others, it became an absolutely terrifying, for very good reasons, time to be in this country.

I was blind to a lot of that for a long time. It’s really a conversation and seeing the work of Valerie Core, who helped open my eyes to a lot of that also, who grew up as part of the sick community, sick faith, and sharing the experiences. Then, hearing the news stories, which really didn't land then. Upon reflection, I think as I've expanded my intentional reexamination of my place, and what society really is and isn't all about. I have a different frame on that time now. I know what my experience was, but I also know that that was not the experience. It was profoundly different, depending on who you were.

LW: You went ahead to sell that seven years later. In the process, you innovated, video, yoga, and all these kinds of brilliant, cool things and started Good Life Project. You have mentioned that you started thinking about Sparketype decades ago. When exactly did that first bubble up in your awareness?

JF: Yeah. I think, it was actually 9/11, to be honest with you. I think, it was that moment when I started asking the big questions, and realizing how important it is to use whatever time we've got, and realizing that most of our time, for most of us, is going to be spent working. Depending on who you ask, and depending on who you are, you spend something like a third of your life sleeping, a third of your life working and a third of your life doing random other stuff.

These days, I think, actually, that's not true. These days, I think, people spend more than a third of their life working. I think, the average workweek has gotten – expanded pretty substantially. There's very little differentiation. Boundaries have fallen away with the connectivity and technology. The expectation that you're always on for so many people is there. I mean, you know this, because this is something that you've lived in, so intentional about not stepping into, or really defining exactly the way that you want to live and the way that most people haven't.

The seeds were planted then, because it just got really curious about how people were showing up, and living their lives more broadly. I think, that's where Good Life Project really found its seed. Like, how do we live a good life? What are the components of that? Part of that was always work. The seeds were planted back then. I've really focused in a lot more in the domain of work, probably in the last five to 10 years, and really said, “Okay, so what is this thing called work? How do we both show up and contribute to the world in a meaningful way, but also, do it in a way that gives us back a sense of meaning and purpose and access to flow states and feeling we're fully expressed, and we're excited and energized to do the thing that we want to do?”

Because if you look around, and you ask most people if they feel that in the context of what they're doing, the answer is no. Or, if it's a yes, it's a fleeting thing. They felt that here. They felt that there. They don't know why. They have no idea how to repeat it, how to replicate the feeling, let alone, the notion of making it a sustained thing. For the few people that do, it's usually comes from a place of profound service and sacrifice, which can be really, really important, but we all access that feeling that state in different ways.

I got curious about it, because I would know an artist who is deeply, deeply fulfilled, and they basically exist in their own creative cave, and they're not – in their mind, they're not like, “Ooh, I’m making art to be of service to this person, or to this community.” Yet, they are utterly alive and they have a profound sense of purpose. It's like, we're missing pieces of the puzzle. We've got little drips of answers, but there's got to be more. It started to form into a bit of a quest over a period of years.

LW: When did you first notice that sparked feeling within yourself? Do you remember that moment in time when you were like, “This is it. This is what I've been looking for”? For me, when I've met my meditation teacher, when I moved to LA in 2002, and I was in his presence, and I was like, the way he's making me feel is the way I want to make other people feel. My whole life trajectory shifted in that moment. What was your moment?

JF: For me, it wasn't an association of work. It goes all the way back to where we started the conversation, which as a kid, I was always making stuff. The feeling of being able to create, very often working with my hands. I love the physical act of creation. It brought me to that place that I still yearn to go today. I've since upon, spending a lot of time reflecting and deconstructing what is that state? What goes into it? What are the components?

Realize that even though I didn't call it work as a kid, nobody was paying me to do it, I was investing effort fiercely, often for days and days and days. I would lose myself. I was working hard. When I talk about work also, it probably makes sense to share that I'm not necessarily talking about the thing you get paid to do. It's really nice when it is. I use the word more generally as any way that you choose to invest effort, to invest yourself in the process of devoting effort. That's work. It takes work.

When we can do that in a way that makes us feel alive, and also be compensated for, that's an amazing thing, because then, it can sustain us in different ways. I worked hard to make a lot of different things as a little kid. Some of it, I was paid for, some of it not. I also painted album covers on jean jackets, when I was in high school to make my walking around money, in addition to other things. I would lose days in the basement, just painting. That state to me is magical.

When you ask me, when did I first know, I knew that things like that made me feel a way that I want to feel from my earliest memories. The notion of having that feeling in my work, probably touched down for real when I was teaching in college, because I would just completely lose myself in that experience. It was an incredible thing to do. That was my work. That was how I was building a company at the same time. The notion that I could potentially have that feeling, doing something that would support me, that was probably where it really touched down in a way where I would associate those things with each other.

LW: I guess, what I'm asking is, I think a lot of us have childhood memories of using our imagination and playing fantastical games and really being in the moment. Then, we lose it as we become adults and we get bogged down in the slog of just day-to-day, 9 to 5. Not a lot of us regain it. I feel like, that's what your current work is here to help us do. Maybe even develop language around it, so we can articulate it for ourselves, so we don't have to think it's our imagination that this is something that's nudging me, or urging me, or pulling me towards this way of life. I guess, that's what I'm asking is when did you rediscover it as an adult? Was it when you owned the yoga studio? Or you saw that community getting built?

JF: Yeah, it was probably as a yoga studio. Because I definitely did not have it when I was practicing law. Yeah, it was almost the exact opposite of it. I would think that I was there for eight hours, and it was an hour, which is an awful experience. It was the yoga. In the fitness world, that was more of a business. I learned a ton from building my own facility. There's a lot of fun. I think, really, the deeper sense of showing up and feeling like I'm doing the thing I'm here to do was really probably, touched back down in the yoga experience.

In no small part also, because I think, part of it is I was – it was a blend of entrepreneurship, which I love in this process of creation. It was every day, because I was teaching also. I'm literally stepping onto a floor and I'm creating a moment, or experience not dissimilar to way back in the DJ experience. I'm seeing the effect. It took me somewhere. I would blink, and I'd be teaching a 90-minute class now literally like, I taught in a way that forced me to be hyper-present and to be in a flow state the entire time.

I would teach. If you stopped me 48 minutes into a 90-minute class and said, “What are you going to say next and what sequence or posture? Are you going to offer next year students?” I couldn't tell you. It was a 100% in the moment. I was in the room with everybody, scanning to try and to feel into what they needed, and any given moment in time, and just, I would give them what I hoped was what they needed.

There were times where I would step onto the floor feeling terrible. I mean, brutal headache. As soon as I started into class, everything else vanished away. I was in that state. I would step out then and have thinking, like the toilet would be overflowing, because I was an entrepreneur and we have three people working there, I think would go and plunge it. There was enough of this stuff that was amazing that took me there, in the context of the reality of building a business. That was probably the thing that really reminded me of who I was, and what was possible. You could feel this way in the context of the central thing that you do.

[END]

 Thank you for tuning into today's episode with Jonathan Fields. If you'd like to follow his work, you can find Jonathan on the socials @JonathanFields, or visit goodlifeproject.com to learn more about his books, podcast, and community.

And if you enjoyed this conversation, be sure to check out his first appearance on my show, which is Episode 73, where we talk about his full story, the complete Journey from leaving law to opening a yoga studio, and eventually to launching the Good Life Project. 

And if you know of someone else who's out there making the world a better place, please send me your guest suggestions at light@lightwatkins.com. Also, please take a moment to rate and review this show. It really does help. And in the meantime, I hope to see you next week for another story of an ordinary person doing extraordinary things.

Until then, keep trusting your intuition. Keep following your heart, and keep taking those leaps of faith. And remember, if no one's told you lately that they believe in you, I believe in you. Thank you and have a fantastic day.