Jonathan Fields: Self-Inquiry – The Ultimate Life Hack?

March 10, 2019 | Episode #3

Jonathan Fields, an expert in applied personal development and human potential, shares a cornucopia of useful tools for living a life deeply aligned. The core tool is self-inquiry, a practice Jonathan notes was a foundational part of education amongst the Stoics, Greeks, and others, and one that is lacking today in a way that can easily lead us astray. Combined with thoughts on disrupting yourself in the spirit of continuous growth, listeners will be inspired to think of life as a “continuous project.”

“One of the biggest shifts that I have made is a long-standing commitment to self-inquiry. I think we’re sort of in a moment where we’re so externally focused… technology gives us a ton of stuff and it flattens the world. At the same time, it also pulls us out of ourselves.”


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Jonathan Fields: I think the biggest shift has been me realizing that whenever I can’t make a fairly quick decision, it’s generally not because I don’t know the right choice. It’s because I haven’t investigated my own internal drivers, preferences and orientations at a level which would make the decision clear.

Manisha Thakor: Hello and welcome to the true WELLth podcast where each week we bring you thought provoking insights from a wide range of experts with one specific goal in mind. To help you identify what tiny tweaks, radical reboots you can make so that the way you spend your money and your time is in deep alignment with what matters most to you in life. I’m your host Manisha Thakor. My guest this week, who you heard in the opening is Jonathan Fields. The bio he prefers is simply New York City dad, husband, maker. If you’re itching to know more about Jonathan’s professional background, I’ll sum it up as this. Jonathan is an SEC and megafirm lawyer, turned award winning author, serial entrepreneur, an expert in applied personal development and human potential.

Manisha Thakor: Jonathan has founded a number of wellness companies, taught everything from yoga and mindfulness to entrepreneurship and innovation. Wearing this latter hats he’s led workshops, events, and retreats around the world for thousands. When it comes to the concept of holistic wellbeing, Jonathan is both a seeker and a teacher who shares his knowledge in a very down to earth and practical manner. But I think the best way to get a feel for Jonathan and his work is to hear from him directly.

Jonathan Fields: I have caused some pretty big painful at times disruptions in my own life just because I realized that what I was doing was not aligned with who I was, what I cared about, and the way I wanted to live my life. So I mentioned in a past life I was a lawyer, and I started out in the federal government working for the SEC and then moved into one of their sort of giant firms in New York City. And realized pretty quickly after actually landing in the hospital, I’ve been having emergency surgery, that it was not my path. I don’t knock the practice or the pursuit of law, just wasn’t for me, especially the way that I had been going about it.

Jonathan Fields: So I made a decision as a lawyer after having invested time and money and going to law school and then building a career to essentially walk away, to say, “You know what, if I have had some level of success in a career where I really had no genuine passion or drive to go anywhere within the career, I didn’t want to be a partner. I didn’t want the carrot that was being dangled in front of me eventually.”

Jonathan Fields: Then I would ask myself, “What if I invested that same level of energy and intentionality into something where I did care? And at the same time I’ve always been deeply interested in sort of the human condition, in wellness and the mind body connection and in building things. I am fundamentally what I now know to be and what I call myself is a maker, which means I make ideas manifest. I love the something from nothing process and when it can be wrapped around a subject area or topic that I really feel strongly about and be in service of others, then that’s a pretty cool thing.

Manisha Thakor: Like many longtime New Yorkers, Jonathan was going about living his daily life when the shock and horror of 911 hit. In the ensuing years I’ve heard many stories of people for whom this was an exceptionally catalyzing event. One that like a diagnosis of a serious illness or death of someone you care about deeply shakes you to the core and literally forces you to stop the hamster wheel of modern life and rethink everything. For Jonathan, this was indeed the case.

Jonathan Fields: Back in 2001 I was married, I had a three month old baby, a new home, and I was looking to start a new venture that would in some way be based around community and service. And I was fascinated by yoga and the yoga world. I had in a very past life been a lawyer, then become a founder in the world of fitness and wellness and then sold the company and I was looking for something new to do. And I got fascinated by the idea and the possibility of opening a yoga center in New York City. And I signed the lease for … I signed a six year lease for a Florida building and I signed that lease the day before 911. And I woke up the next day and we all know what happened that next day. Being a very long time New Yorker, first thought is just the horror of what was happening and who did I know.

Jonathan Fields: Because anybody who was in New York for any amount of time knew somebody who sadly was lost that day. And then the next question was, “Am I really going to do this?” I mean, I have to support a family and it’s hard to start a new company in any climate, but you know, to do that in the context of a city that was just absolutely blanketed in pain and an economy that was in shock. It was a really tough choice. But what I realized over the next couple of weeks really thinking it through and having experiences and reflecting on one of the people who I knew who never came home to see his kids was that we really, we have one pass through. You know, we have one shot at this thing called life.

Manisha Thakor: Fueled by that powerful reminder that we have just one pass through this thing called life, Jonathan found his answer.

Jonathan Fields: There was still … If there was a need for a community and healing and movement and breath before this moment, it was exponentially magnified after. So I decided to go ahead with that and went to work, built that for a number of years in … I actually seven years in I guess it was, at the end of 2008 sold the company and it exists to this day, some 17 years later, it’s still this beautiful center that’s in service of a lot of people in New York now having probably tens of thousands of people pass through, having trained hundreds if not thousands of teachers who are around the world teaching at this point. So it was an amazing experience to be a part of.

Manisha Thakor: Disruption. It’s a word that Jonathan embodies. Well, that’s just the way it’s always been done, is not a phrase you’ll hear coming out of Jonathan’s mouth, “Furthermore, this drive to disrupt extends to himself and disrupting yourself in the spirit of continuous growth is often the hardest thing to do.” So after Jonathan sold his business in 2008 this serial entrepreneur switched gears yet again, and entered a new phase of making and of building. This time he shifted his focus to becoming an expert in applied personal development and human potential. So Jonathan, I can’t help but wonder, having heard so many stories through the course of your current work and taught so many lessons to others, what do you feel is the biggest shift you’ve made in your professional life to improve your overall wellbeing?

Jonathan Fields: Yeah, so it’s a great question. I think the one of the biggest shifts that I have made is a longstanding commitment to self-inquiry. I think we’re sort of in a moment where we’re so other focused and so externally focused and technology is actually, while technology gives us a ton of stuff and it flattens the world, at the same time it also, it pulls us out of ourselves. It makes us so focused on telling a story to the world very often that is not that related to who we are, and what we really care about, rather than focusing inward. Taking time in solitude, exploring, being still and really going through a process of self-inquiry to understand who am I, what drives me, what do I care about? What matters to me? Who matters to me? And how do I want to invest my energies, whether it’s in work and relationships and health. As I kind of look out into the world that we see a lot of people suffering from what they would say in some way, shape or form is decision fatigue.

Jonathan Fields: And I actually don’t believe the problem is an inability to make decisions. I believe that the problem is an extraordinarily high level of self-ignorance, and not ignorance in a judgemental way. It’s just that we’ve gone to school to develop expertise in all sorts of domains and processes and tools. But rare is the person who’s actually devoted themselves to a genuine sort of progressive educational process of self-inquiry. And you know, that used to be the heartbeat of education. You know, if you look at the ancient Greeks, the stoics.

Jonathan Fields: If you look at the ancient philosophers and a lot of other cultures, everything started with really deep self-inquiry and self-exploration and contemplation. And that’s kind of been stripped from the process of education these days. And for some reason I had a sense of this and also realize that I just really didn’t know well that I want it, and probably over a period of decades now. I think the biggest shift has been me realizing that whenever I can’t make a fairly quick decision it’s generally not because I don’t know the right choice. It’s because I haven’t investigated my own internal drivers, preferences and orientations at a level which would make the decision clear.

Manisha Thakor: Jonathan’s point about the importance of developing the skill of engaging in a lifelong process of self-inquiry, self-exploration and contemplation as a means of making decisions that are truly aligned with who you are, sure hit home with me. After 25 years of working in the world of financial services, I’ve observed that for a fair number of people, myself included, money can be the driving or sole determinant of what they do or don’t do with their time. Alas, that mindset can easily lead to a life half lived. So I asked Jonathan when he talks about these disruptions and shifts in his personal life, what factors does he consider?

Jonathan Fields: Sometimes the answer is the thing that allows me to go from one thing to another, to another, blind faith, and sometimes stupidity. It’s not always smart, but what I have learned is that, and also, money does matter to me. I’m in the middle years of my life. I’m married, I’m a father, I live in New York City. It is not an easy thing to sustain yourself with a family in New York City. So for me, and you know I’m also, I’m at a moment in my life where I am not willing to go back to zero. I’m not willing to live in a van, I’m not willing to have to start over. And as always, like no judgments for anybody who would make a different decision or be put in a position where they have to be there.

Jonathan Fields: But to the extent that I can sustain sort of the lifestyle that I’m comfortable with now. I want to do that. And at the same time, I’m also acutely aware of the need to do that in a way that allows me to do work that is the truest, fullest, most aligned expression of who I am, of my identity, my capabilities and abilities, my preferences and drivers. So, I started thinking about the idea of running a series of experiments, because the truth is, yeah, most of us never actually go through the process of just iterating on trying to find the sweet spot between what fills us up, what allows us to come alive, what the world needs on a level where they will compensate you for it in a way that allows you to live comfortably and sustainably. And a lot of us actually, we end up locking ourselves into financial circumstances very early in life, especially people who have a very highly leveraged educational experience where it doesn’t allow us to run those experiments. Or at least we feel like it doesn’t allow us to run those experiments.

Jonathan Fields: So I’ve kind of taken the approach and said, “Kind of part of my job is to just keep running those until I find those moments, those projects, those sweet spots, those companies where I feel like I can be that person.” And there have been times where I have found them really quickly. There’ve been times where I have found it and it’s been fantastic for a season. And then I evolved and grew and it was time to … Or the market evolved and grew, or the entity that I created shifted and it was time to move on. And for me, it’s funny, I think about an old friend of mine, Seth Godin. He, after being published by traditional publishers for many years and having mega best-selling books with them, he decided that he wanted to take a different approach and he started his own publishing company and he called it The Domino Project.

Jonathan Fields: And I asked him, “Why is it project?” And he said, “Because it doesn’t lock me into something and say like, this must succeed.” It allows him to approach it in a way, and he says, “Okay, this is an interesting experiment. I don’t know if it’ll work. I don’t know if the market will want it. I don’t know if I will feel the way that I thought I felt about it, but if I say that this is a company and this is what I’m devoting myself to and it must work, then it creates a mindset that is not permissive.” It doesn’t allow you to be agile. It doesn’t allow you to actually re-evaluate if things aren’t lining up right and say, “This was a really good experiment. I learned a ton and it’s time to move on.” And but by sort of in your mind saying that this is a project or an experiment, it lets you enter the experience with a very, very different mindset and your metric becomes, “What can I learn from this?” Rather than this must succeed. It makes it a very different experience.

Manisha Thakor: Looping onto that, the roots of discontent in many people’s lives often comes from a misalignment of how they spend their money and their time with what’s most important to them in life. Have you had any recent “aha” moments when you realize that you are discontent?

Jonathan Fields: I have had so many “aha” moments where I have realized that I am fiercely out of alignment with everything that I claim to hold dear. Maybe among the more recent ones was actually in towards the end of 2017 I had … I was coming off of having started a new venture the year before, supporting it, growing it, it was flourishing. It was successful. I was working on building media and doing some other things and I hit a point in the fall where I realize I was completely and utterly burned out. I just had nothing left to give. And it was affecting my state of mind. It was affecting my health. And I’m the guy who sits there and says, “Don’t do that.” I’m the guy who publicly proclaims like there’s a different way to go about it. And yet just like everybody who I am in service of and I think about and hopefully create solutions for, I’m human.

Jonathan Fields: There are times where I push too hard. I don’t listen to myself. I don’t listen to my body. I don’t watch the signals, because I’m just … I get overcommitted to particular things. What I realized was that, reflecting back to what I shared earlier, my primary driver is the drive to make. I am happiest when I’m in the cave creating, I am. That is kind of what I’m here to do, and what I realize is that when I get too far away from the process of me being in my creative space, really going deep into the process. That I began to suffer and I began to be of less use to others and my ability to make, to create, to innovate, to bring forth new ideas, it really suffers. And I become stifled. And if you add to that, if I am building something where part of what I need to do is be very forward facing, be around a lot of people and be very service facing, then that compounds it because I’m also an introvert.

Jonathan Fields: I get full, I get my energy from solitude or from being around one person or a small number of people in sort of like calm or quiet or deeper conversation. When I am around large numbers of people for long amounts of time, very forward facing, that actually takes energy from me and I need to refuel. And so it was a blend of me not honoring my social orientation and doing work that did not allow for me to also really fully express my sort of primary driver for my essential nature. Those things centrally are the two big things. Those sent me, they really took me out of alignment and I felt it in a huge way. I was just physically and emotionally empty and I had to hit reset.

Manisha Thakor: Hitting reset isn’t always easy to do, and nor is it easy to recognize the form it needs to take, but hitting reset may be precisely what has to happen for one to live a life rooted in wellbeing. To recognize when and how to accomplish this reset requires that mastery of self and introspection Jonathon spoke so eloquently about. Something I found very inspiring for those of us who may be at the early stages of this journey is that there are daily rituals that aren’t nearly as drastic as a complete reset, yet can still result in deeply impactful shifts in your life.

Jonathan Fields: So the daily habit that most strongly supports my personal wellbeing is mindfulness. Mindfulness on two levels. Mindfulness in the context of how I live my life on a moment to moment basis, trying to be present in real time to who and what’s in front of me so that I can take it in and be more proactive, responsive and intentional rather than reactive. And mindfulness in terms of an actual sitting daily meditation practice. So I wake up first thing in the morning and I actually do a Pranayama or breathing practice, and then I move into a seated mindfulness practice and it’s the same six days a week. I change it up on Sundays because I actually do a meta or loving kindness practice on Sundays instead. But that has been my pretty much daily practice since 2010 and it’s been pretty transformational.

Jonathan Fields: And one of the most powerful things about the practice is not even what you notice is different, but what you notice isn’t happening anymore. It’s a much subtler thing. So what you’ll notice is that things that would trigger you don’t catch you as much. Things that would cause stress or anxiety you’re able to breathe through and let go of. Things that you would spin. You’re able to see yourself spinning and choose a different response. People in your life you become more present for. You start to see them more rather than seeing the pattern that you had formed around them when you were 16 years old and responding to that. And you start to see bids for attention and be able to respond to them in a way which deepens relationships. So for me, it’s been a really powerful practice of both learning how to direct my attention to the people in parts of life that matter most to me. Learning how to drop the thoughts that are least helpful and come back to the present moment and try and enjoy what’s in front of me.

Manisha Thakor: Reflecting back, I think what I love most about this conversation was Jonathan’s commitment to self-inquiry as a means of leading a life that brings both personal joy and at the same time enables a contribution back to the greater good in whatever way one feels called to do so. Jonathan’s observation that technology has woven itself into the everyday fabric of our lives, so much so that many of us have ended up overly externally focused and disconnected from ourselves also really resonated. I found Jonathan’s comments inspiring me to want to seek that place of stillness and quiet presence necessary to shift from a worldview driven by an inner focus to a worldview experience to the much broader lens of an expansive outer view. Lastly, I was also struck by just how freeing Jonathan’s view of himself as a maker can be. By relieving himself with the pressure of perfectionism and replacing it with an approach of experimentation, Jonathan has put himself on a sparkly path that allows for continued growth and evolution in all aspects of life.

Manisha Thakor: To learn more about Jonathan and his work, simply read the show notes for this episode at, remember that’s wealth spelled W-E-L-L-T-H. In the show notes for this episode, you will find links to Jonathan’s primary website,, and to his most recent project called Sparketype, which helps people explore and answer the age old question of, “What am I actually doing with my life?” In the show notes, you’ll also find Jonathan’s full bio and all social media. If you aren’t already following Jonathan online in some format, I strongly encourage you to do so. His life insights are like a bubble bath for the brain.

Manisha Thakor: Lastly, here it comes. The shameless, heartfelt, from the soul plea. If you enjoyed this podcast, we ask from the very tips of our toes. If you would consider taking less than five minutes of your time to go to our show page on iTunes and leave a detailed review, hopefully a five star one. These reviews are the primary way other listeners on the same journey as you find this podcast, if you’ve ever had an itch to pay a kindness forward, this is a quick and powerful way to do so. I’m Manisha Thakor, and that’s it for this episode of the true WELLth podcast.

Announcer: The true WELLth podcast is made possible by Brighton Jones, an innovative wealth management firm founded 20 years ago in Seattle. Today, Brighton Jones serves a nationwide client base with the singular goal of helping them live richer lives. Today’s episode was edited and produced by Stan Hall with help from John Dougherty, Hallie O’Reilly, Michael Stubel, Marc Asmus, and Chris Sylvester. For more info on our show, visit

Resources Cited in the Episode
Jonathan Fields' website
Jonathan Fields' books