How to Take Action in Spite of Self-Doubt | Jonathan Fields

How long have you been waiting to feel confident enough to do the things you dream of doing? Maybe to go for that new project or job, or approach someone you’re interested in dating, or maybe start a new side hustle or business, or start a podcast, write a book, make art, whatever it is.

We keep telling ourselves, Oh, I’m not confident enough to do that yet. But what if that was all an illusion? What if confidence was actually more fake than real, and waiting for it to magically arrive was stopping us from living a truly amazing life? So sure. We hear a lot of talk about how to become more competent.

Lemme do that. So, sure. We hear a lot of talk about how to become more confident in relationships at work and the pursuit of big visions, goals or dreams. But what if that confidence was really the wrong thing to be pursuing? What if in fact, That magical state of confidence even arrived, and it was actually not the asset or ally we thought it would be, but was rather a sign of an unwillingness to grow, to take meaningful risks that could lead to a better life, better relationships, better work experiences, and more.

What if, in fact, It was the very willingness to live, to make decisions, to act, when to take actions, when you not only were not confident, but literally could not be confident, given the circumstances, that was the real power move in life. What if cultivating the skill of unconfident action was the unlock key for so much?

And chasing confidence was really just this distraction that kept you from doing all the amazing things you dreamed of doing, and creating, and making all the awesomeness you’d love to bring into your life. And even becoming who you deeply yearn to become. Well, that’s what we’re talking about in today’s special solo episode, how to stop waiting for the magical and elusive confidence to kick in and just learn to take decisive action that leads to powerful, even life-changing outcomes, even when you don’t know how it’s going to work out.

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photo credit: Nick Onken


Episode Transcript:

Jonathan Fields (00:00:00) – It’s the moments that we are not confident, but we find a way to do it anyway that hold the greatest opportunity for growth, for connection and for impact. So rather than having a conversation around confidence, I think the more valuable conversation is what are those deeper skills, the meta skills that we really want and need to cultivate, the ones that allow us to act even when we’re not sure how things are going to end, even when we’re not very confident either in ourselves or in the idea, or in the possibility of what is spinning around in our head. What are the core skills that we can cultivate that will allow us to continue to assess the moment and then to potentially make decisions and take actions that would move us forward even when we are not fully confident and we don’t know how it’s going to end. I’ve got a question for you. How long have you been waiting to feel confident enough to do the things you dream of doing? Maybe to go for that new project or job, or approach someone you’re interested in dating, or maybe start a new side hustle or business, or start a podcast.

Jonathan Fields (00:01:21) – Write a book, make art. Whatever it is we keep telling ourselves, oh, I’m not confident enough to do that yet. But what if that was all an illusion? What if confidence was actually more fake than real and waiting for it to magically arrive was stopping us from living a truly amazing life? So sure, we hear a lot of talk about how to become more confident in relationships at work and the pursuit of big visions, goals, or dreams. But what if that confidence was really the wrong thing to be pursuing? What if, in fact, that magical state of confidence even arrived and it was actually not the asset or ally we thought it would be, but was rather a sign of an unwillingness to grow, to take meaningful risks that could lead to a better life, better relationships, better work experiences, and more. What if, in fact, it was the very willingness to live, to make decisions, to take actions when you not only were not confident, but literally could not be confident given the circumstances.

Jonathan Fields (00:02:26) – That was the real power move in life. What if cultivating the skill of unconfident action was the unlucky for so much, and chasing confidence was really just this distraction that kept you from doing all the amazing things you dreamed of doing and creating and making all the awesomeness you’d love to bring into your life, and even becoming who you deeply yearn to become. Well, that’s what we’re talking about in today’s special solo episode, How to Stop waiting for the magical and elusive confidence to kick in and just learn to take decisive action that leads to powerful, even life changing outcomes, even when you don’t know how it’s going to work out. So excited to share this deep dive on confidence with you today. I’m Jonathan Fields and this is Good Life project. So I want to take you back in time a little bit and tell you a story. This story actually takes place more than two decades ago in Hell’s Kitchen, New York City. A young dad with a three month old baby, a new home, married, living in the city that I had known my entire adult life.

Jonathan Fields (00:03:44) – And I get this idea in my head. I had left a big career in law to go back into the world of entrepreneurship and well-being, and started out by actually building a gym that I exited after about two and a half years, sold my interest in that, and I was living in Hell’s Kitchen, and I had this deep fascination with the world of yoga and the mind body connection, and I wanted to deepen into that. And I saw an opportunity to potentially create what I hoped would become one of the premier yoga centers in New York City. So I kind of went all in. I was searching around and I found not too far, just a couple of blocks from where we were living in Hell’s Kitchen, New York. And this is for those who don’t know, this is a part of New York City, which is sort of like over on the West Side, Midtown, which back then on a block by block basis, you never entirely knew what you were getting to meet up with. And it was a lot of adventure, a lot of fun.

Jonathan Fields (00:04:43) – The huge amount of change happening in the neighborhood. And I found this space. It was a second floor space in 115 year old building. And I met the the owner of the building there. Actually, we walked upstairs and we opened the door and it was kind of like this 2500 square foot open loft style space that was completely a wreck. It looked like somebody had been squatting in one part. It looked like the walls were coming down. Another part, it just it was a disaster. And I looked around and then I saw this beautiful giant all glass picture window on the second floor overlooking ninth Avenue, facing west. So we get late day sun straight into the practice room. And I saw it. I saw it clear as day and I was so excited. I literally ran home to Stephanie and my wife and I said, you’ve got to see the space. We went back, she saw it, and she’s normally my counter when I’m a little bit of a visionary who just believes anything can happen.

Jonathan Fields (00:05:43) – I’m deeply optimistic. She’s a grounding force and we’re a great balance in that way. And she looked at this space and she said, yeah, I can see this too. So we’re both on the same page. So we went home that day and had some back and forth with the building owner, and I found myself a couple of days later signing a lease for a floor and building a six month lease for a floor in a building in Hell’s Kitchen, New York, with a three month old baby in new home, married, living in New York City. I went home that night terrified, nervous, excited. All of the things that you feel when you’re about to start a new business and starting new businesses is not a new thing for me. I’ve literally been doing it since I was a kid. I know the feeling of it. I know the anxiety of it. I know the uncertainty of it. I’ve done well and crashed and burned enough times to know that I can find my way through.

Jonathan Fields (00:06:41) – But it was still all the feels, all the nerves. And a lot of that was because there was no guarantee this was going to work. There is never any guarantee that something like that is going to work. In fact, it was a huge risk. Something like 95% of all new businesses fail within the first five years. So if anything, the odds were against me, especially given the fact that I was planning to launch a yoga studio, having very little experience in the world of yoga. But I believed I could figure it out, even though there was no rational basis for me to be confident. There was just something in me that says, I don’t know if I’m the right person for this. I don’t know if it’s going to work out, but what’s on the line and the sense of possibility and potential impact was enough to drive me to keep doing it. So I went to bed that evening with all of the feels. I woke up the next day, turned on the news, and learned that a plane had hit one of the towers.

Jonathan Fields (00:07:46) – You see, I signed a six year lease for a Florida building as a new dad owning a home. Married the day before nine over 11 in New York City. So all those feels and anxiety and sense of uncertainty, and I don’t know how it’s going to work out that I had felt the day before. I now woke up to the realization that my city, the city that I had known my entire adult life and loved and lived in, was now going through something terrifying and profound. And as the towers fell. So did my heart. So did my soul. Everything was just crushed. And of course, two things started spinning in my head. One is, who did I know? Because pretty much anyone who had lived in New York City for any amount of time knew somebody who was at least down there. And in fact, we did know people who never came home that day. The second thing was, what am I doing? I literally just signed a six year lease for a Florida building, which is very risky to start what I hoped would be this great new venture.

Jonathan Fields (00:08:53) – And now I pile on top of that the fact that my city is in a state of profound loss and grief and mourning, and so much of it was, I mean, literally shut down the entire South part of Manhattan was effectively a zone that was taken over and so much business was shutting down. There was fear that went far beyond New York City, the entire country, and in fact, parts of the entire world just pulled back because they didn’t know what was coming next. The level of uncertainty was ratcheted to a place that probably until the last few years, I had never experienced before, and I had to make a decision. Do I continue to push forward with this dream, with this vision, with this endeavor to open a place of joy and community and breathing and possibility and peace and equanimity and movement and collective effervescence? Do I move forward with the dream to create that, given the circumstance that I was now faced with? And later that afternoon, my wife and I took our daughter, put her in a car seat, drove up to the home of our friend who was then the youngest partner in financial firm that was at the very top of one of those towers to sort of sit vigil and just be with his wife, who was also a friend of ours, and and hope and wait and pray.

Jonathan Fields (00:10:24) – None of that would be answered in a positive way. But as we drove home that evening, we were last ones to leave. Everyone slowly filtered out, and Stephanie and our friend went upstairs to read nine month Old Kid just some books and stories and put him to sleep. And they asked if I would go and sit next to the two and a half year old and read him a bedtime story. And I’m walking up the steps, and I remember opening the door and just seeing him sitting there with a little picture book on his lap and sat down and read, knowing that I had no idea if his dad was ever coming home again. And it was such a tough moment. Not just for me, you know, for everybody there. I was literally just playing a supporting role. And as we drove home that evening in partly silence and also partly just having a conversation and saying, how do we navigate this moment? There is profound uncertainty. I have no rational basis for confidence that moving forward with a business endeavor in the heart of New York City, in this moment in time, is the sound decision, or that I can make it work.

Jonathan Fields (00:11:31) – And yet, the very fact that we knew somebody who, at that point in time, we started to realize was increasingly likely would never be home again, brought me to the truth of my own mortality, the truth of the fact that we were promised nothing. Not another minute, another hour, another day, week, month, or year. And to the extent that I wanted to act in this moment to do the thing that both terrified me, but also had on the other side the potential for expression and joy and grace and impact. We decided that we couldn’t not say yes to that, and to also potentially creating a place of community and healing and solace at a time where the city that we love so much needed it more than ever was. I confident it would work? Anything. But yet I knew inside of me that I still needed to move forward. And we did. We had all of these plans that just I had experienced in the fitness world. So I knew how to launch a gym, and we were going to launch it in this big, fancy, new way and the way that the yoga world had never seen before with celebrations.

Jonathan Fields (00:12:46) – Of course, all that went out the window. We had to change everything we’re doing to really meet the moment and meet the soberness of the moment in a healing and respectful way. And as we opened, I remember to the date it was November 19th, 2001. We signed the lease on September 10th, the day before 911 made the decision to continue to move forward with it. Went in there and with my own hands, and the woman who would eventually become partner in the business, rebuilt the entire space from the ground up to be something beautiful. And we opened on November 19th. And people. Came. Not only did they show up, but they showed up in waves and droves and we had this just stunning place of community. And I remember teaching during that time every night, 630 class in 1000 square foot practice room, literally mat to mat with these 115 year old cast iron radiators clinking and clanging. And the entire picture window in the front is a sunset set early back then, because we were heading towards winter and the entire window just being fogged with the breath and the humanity and the expression of everybody in THAtrillionOOM 50 bodies moving in synchrony and harmony, often just lying on the mat and weeping because that’s what the moment brought out of them, and us and me.

Jonathan Fields (00:14:14) – And that grew over time to be a place not just where people got to exercise and do yoga and move their bodies and get fit and strong and flexible. But a place of community and healing and solace and a place where we ended up training hundreds of teachers from around the world, even in different languages, where tens of thousands of students would eventually come and become a part of the community and practice. And over the years, it grew into just this incredible experience. And that was all not because I was confident in moving forward in the beginning, but because I had developed the skills to actually say yes, to move forward when I was completely not confident. But there was something underneath it that drove me to still make decisions and take actions that led to an experience that has touched and changed my life and I know touched the lives of tens of thousands over a period of decades now. I was able to exit that when eventually my interest started to focus more in writing and doing all sorts of other things. In 2008, after seven years.

Jonathan Fields (00:15:33) – And that community remained stewarded for decades, and to this day remains a place where people can connect and practice. And I share that story because it relates to the conversation around confidence and the idea that it’s really not about having or waiting for the confidence to take root, to do the thing that you dream of doing in real life. We don’t need to be confident. In fact, I would even argue that the only way to be 100% confident, which is what so many of us wait for. The only way to be 100% confident about anything is if you’ve already done it, or someone else has already done the thing you dream of doing, and at that point, the stakes are so low, it just doesn’t matter to you or to anyone else anymore. It’s the moments that we are not confident, but we find a way to do it anyway that hold the greatest opportunity for growth, for connection and for impact. So rather than having a conversation around confidence, I think the more valuable conversation is what are those deeper skills, the meta skills that we really want and need to cultivate, the ones that allow us to act even when we’re not sure how things are going to end, even when we’re not very confident either in ourselves or in the idea, or in the possibility of what is spinning around in our head.

Jonathan Fields (00:17:08) – What are the core skills that we can cultivate that will allow us to continue to assess the moment and then to potentially make decisions and take actions that would move us forward even when we are not fully confident and we don’t know how it’s going to end. And when I think about these skills, it really short and sweet framework that comes to my mind and I call it the ABCs of Unconfident Action. And the A here is awareness and ease. It’s our ability to see clearly and to find groundless peace. The B represents bravery, a willingness to act when you don’t know if it will work. And the C is all about conviction and this is why it matters so much. So I want to dive into these three different things, because I think they’re really important for us to explore and figure out how do we actually cultivate that awareness and ease that bravery and that conviction, so that we can actually meet these moments of profound opportunity where we don’t know how things are going to end, but we can still say yes to them and open the door to just incredible experiences.

Jonathan Fields (00:18:22) – A vastly expanded and abundant life. How do you get these ABCs? Well, let’s kind of start from the bottom up here, and that’s with the C with conviction. Conviction isn’t the type of thing where you have to be 100% convicted or behind this, but you have to have a sense of conviction around whatever it is that you’re thinking of doing, even just a little bit. And what I found is that that sense of conviction that this is possible, maybe not 100% possible, but this may be possible. And I am deeply invested in this. That’s what I mean by conviction, is that I am vested and invested in this, and I find that the power move in cultivating conviction when we’re looking to actually step into doing something is to ask the why question, or sometimes the why questions. And the big one is, why is this important to me? Why does it matter so much? The reason this is so important is because anything that you say yes to that is genuinely worth saying yes to that holds the potential to change you in some way, to grow you in some way, to connect you both to yourself on a deeper level and to others in a meaningful way.

Jonathan Fields (00:19:44) – There is going to involve uncertainty. There’s going to involve unknowns, and you are going to face adversity and challenges along the way. It’s just the nature of anything genuinely worth doing. The illusion of a straight, easy path to whatever it is that you seek to achieve or become. It’s just a myth. It’s mythology. So let’s accept the fact that adversity and challenge are going to come our way. The thing that allows you to move through this adversity and challenge often one of the biggest things is understanding. Having absolute clarity around why you said yes in the first place. Why was it and why is it so important to me? Why does it matter so much? And I find often that there’s an exercise that people describe in various different ways. I describe it as the five whys can be incredibly powerful in these moments. To help you get to your why on a level that is deeply embodied and visceral. Because what tends to happen when we ask the why question like, why is this important to me? Why does it matter so much? The first answer that we give is kind of superficial, you know? So when I go back using the example of opening a yoga studio in Hell’s Kitchen, and if I answered the first question like, why is this important to me? Well, on the top, well, I’m an entrepreneur.

Jonathan Fields (00:21:13) – I love to start businesses. This would be a really cool business to have. Like I could see myself enjoying this. Okay. Surface level. Why right? Is that going to get me past the fact that I woke up the next morning and it was 911? Is it going to get me past all of the struggles and the challenges and the managing cash flow? And then when people would show up and then when they wouldn’t show up and personnel and managing a physical space and all that goes wrong with it, is that going to get me through? Is that level of conviction, that surface level? Why going to help get me through all of that adversity? Not a chance. You need to go deeper. Well, cool. What’s the second why? So I asked them why question again what’s underneath that? Well, if I think about it, it would be amazing to have a space where I could bring people together and actually have them form a community, because community is something that is getting really lost in the human condition.

Jonathan Fields (00:22:12) – And wouldn’t it be cool if I could build a business that would both support me and allow me to create a sense of community for people that maybe didn’t have it? Okay, so that’s a deeper level. Why? Interesting. Why is that all so important to me? Now I’m going to my third level. Why here? And I’m getting closer to a level of understanding why this matters so much to me, why it’s so deeply meaningful, that will give me the conviction that will help me, whether adversity that I know will come. So why? Why does that matter so much to me in this context, using the example we’re using. Hmm, why does it and these were questions that I was asking myself regularly back then and ask myself for years. And what I started to realize was that this was both a place not only a community, but a place where I could step into it and find a sense of belonging, but also a place where I could start to become the next version of myself, where I could actually deepen into the study of eastern philosophy, eastern traditions, to learn Sanskrit, to study the Bhagavad-gita and the sutras and all of these things that I had wanted to learn, because it was it was a deep fascination of mine, and I wanted.

Jonathan Fields (00:23:28) – The insights and the depth that I wanted to be able to study it and share it with other people. So this was a profound learning experience for me as well. Well, okay, now we’re getting closer to the core because if I lost that, that would also be a very personal loss for me. The opportunity for growth on a very deep and embodied level. Why is that so important to me? Huh. So I had to think about this at the fourth level of why there. And I realized that part of the reason that I was an entrepreneur was because I loved to make things that moved people. And that also allowed me to feel like I was fully expressing the essence of who I was. And this particular vehicle would allow me to do that, to literally get closer to the bone of who I was on the most essential level as a human being. If it worked out again and there are no guarantees. But if it worked out the way that I saw it in my head, this would allow me to be more closely in the world to who I really was at heart, in my essence.

Jonathan Fields (00:24:35) – And that really mattered to me. And I think especially then, because I was moving through a season of reimagining and rediscovery and trying to ask myself, who am I really? What matters to me and how might I show up? And that actually got me close enough. I didn’t even need to get to the fifth. Why? That got me close enough to understanding why this was so important to me, why it matters so much. It mattered to me as a human being, looking to go deeper into my identity and feel fully expressed and alive. It mattered to my deep desire to build a community where I could step into and be a part of it, filled with love and dignity and respect and healing and openness and spaciousness and abundance and acceptance. It mattered to me because I love building businesses, and this was a business that had so much soul and emotion and support to it. It mattered to me because I also wanted the opportunity to create something that would have a big impact on a lot of other people, and at the same time, support me and my family in New York City, especially at a time of profound uncertainty.

Jonathan Fields (00:25:42) – So all these levels of Y stacked up, and that gave me a level of conviction where when I looked at the deeply uncertain circumstances that I was facing, it allowed me to continue to say, yes, I’m still going to move forward with this. Yes, I realize that there’s a lot of risk here. I don’t know how it’s going to end and the stakes are very high, but it’s the thing that I can’t not do right now. And it allowed me as adversity came and it came over and over and over, sometimes in ripple, sometimes in what felt like sunni’s, it allowed me to keep going back to that deep understanding of why this mattered to anchor in that sense of profound embodied conviction and keep saying yes to moving forward. So that’s the see the conviction. Remember, we had sort of three elements of the framework conviction, bravery and awareness and ease. So let’s move up to the be the bravery part. And those who are familiar with Brené Brown’s work, who I love and who has been a past guest here on the podcast, may remember her at one point saying a phrase which I won’t get exactly right, but she basically says, don’t be confident, be brave, or don’t be courageous or whatever it is.

Jonathan Fields (00:27:03) – But bravery is at the center of so much of what we do. It’s about being brave and taking action, even when we don’t know how it’s going to end. When something genuinely matters, we are rarely able to have certainty or perfect information before committing and acting. And that’s where the bravery part comes in. And we stack this on top of the why the deep, embodied understanding of why this matters so much. And then it’s a matter of saying like, how do we be brave? How do we actually make decisions and take consistent action that will move us forward when there are very high levels of uncertainty, and especially when the stakes are high and when the stakes are not high, it just doesn’t matter. So none of this really matters and comes into play. But when the stakes are not in some way meaningful to you, if you never actually put yourself in a position where you have to take action, where you get to choose to take action and make decisions where the stakes are meaningful to you.

Jonathan Fields (00:28:03) – If you never put yourself in that situation, you are effectively foreclosing any opportunity of growth, of connection, of impact and expression, and stopping yourself from living a good life. So we have to put ourselves in these moments. And what we know is that when we put ourselves in these moments, we actually have not just a psychological often. Revulsion or sense of repelling from it. But we have a physiological rejection of these moments. It activates the amygdala, the sort of the fear center in our brain triggers the fight or flight or what’s been expanded to be fight, flight or freeze, or sometimes even people call it fight, flight, freeze or fawn reaction in our body, and that floods our body with a cascade of chemistry. The endocrine system kicks in, floods our body with a cascade of chemistry, including cortisol, the stress hormones in our body that make us feel physically uncomfortable, sometimes to the point of being physically ill. Now, when that happens, that is a reaction that is good and that is natural in our body.

Jonathan Fields (00:29:09) – It’s a reaction to danger. But when it’s triggered on a persistent basis or in reaction to actually things which are just high stakes and uncertainty or meaningful stakes and uncertainty, yet they’re also the gateway to possibility that stops us, that physiological and psychological feelings stop us from moving forward because we don’t know how to handle it. We just feel psychologically filled with anxiety and fear and physiologically filled with a sense of, I just want to be over this. Almost a sense of embodied dread. So what do we do with that? What do we do with that? Instead of backing away from all of these opportunities, possibilities where it’s uncertain and there meaningful stakes? But on the other side of that, if we say yes is incredible ness, how do we be brave in those moments and say yes to it? There are a couple of techniques that I’ve found really helpful. One is what is often called chunking. And when we talk about this, we’re talking about chunking both the stakes and the uncertainty. So we know that we respond to two things here.

Jonathan Fields (00:30:16) – One is the level of uncertainty. If there’s just a low level of uncertainty, we tend to react much less viscerally. Like we’re kind of like, okay, it’s uncertain, but probably only about 5% or 10% uncertain. I can handle that. That’s fine. But when it’s 20% uncertain, or 30 or 40 or 50% or 60 or 70% uncertain, then we start to freak out a little bit. Same thing with stakes. When the stakes are low, it really doesn’t matter to us, so we don’t really care. Sure, I’ll give it a shot. I’ll try it even if I have no confidence if it’ll work or not, because it’s just not meaningful. So we don’t really care. But when the stakes start to get higher, when they start to really involve our sense of self, when they make us have to put ourselves out there and risk being judged or ostracized or not accepted especially, or we’re losing status or whatever it may be, when those stakes start to rise, that’s when we start to pull back.

Jonathan Fields (00:31:13) – So one of the really effective tools here is to chunk both the stakes and the uncertainty into tinier and tinier pieces. So you look at that big thing that you’re thinking about doing the end, right? And you say, okay, what are all of the little steps that it would take to actually get to that place? And instead of saying, okay, so yes to this big thing and focusing on that big thing which is highly uncertain and highly like the stakes are sky high. Instead, we look at those 100 tiny steps, we chunk it down to 100 tiny steps, where now the level of uncertainty about that first baby step is much smaller, and the stakes associated with that first baby step are much smaller. And we say, you know what? I can deal with that if I’m just saying yes to that. If I hold the vision of the big thing out here in my mind. But today all I need to do is say yes to this first baby step where, okay, like the uncertainty is there, but I can deal with a low level of uncertainty.

Jonathan Fields (00:32:18) – And the stakes are so tiny in this one baby step, the first of 100 that it resets our psychology so that we’re much more comfortable saying yes to that. And then what happens is we say yes to that, and we devote a little bit of effort to it. We devote a little bit of time or energy or resources to it, and we’re like, wow, that actually worked out. And now we move to that second out of 100 steps that would get us to the really big vision. And we’re just a touch more brave now because we saw that we said yes to the first one and it worked out. We’re like, huh, well, if the first one worked out, maybe the second one will work out cool. And then we take the second. So what we’re doing is we’re slowly saying yes, not to the big giant thing, but to just tiny little steps along the way. That chunk, the level of uncertainty and chunk this stakes down to the tiniest little elements that our brain is much more comfortable saying yes.

Jonathan Fields (00:33:16) – And every time the step before it proves out, it makes us more comfortable continuing to say yes to the next one. Now, this affects every difference. Level of our lives. Yeah, we could talk about it in the context of big business, things we could talk about in the context of personal life. We could talk about it in the context of relationships and dating. You see somebody who you’re like, wow, this person seems amazing. I wonder if they would be potentially a great person for me to be in a relationship with, maybe even a long term partner with. Maybe they’re my life partner. They just seem incredible. But we’re also we’re really scared. What if we get rejected? What if it doesn’t work out? What if we invest all this time and years of our lives and then it doesn’t work out and we just spin in our heads like the uncertainty and the stakes get higher and higher and higher. We turn them into life and death. Right? Rather than just saying, well, what if we chunk, just chunk this, right? What if we said, like, what are all the steps between me sitting here saying that person is kind of interesting to me, and then being a life partner for the rest of our lives.

Jonathan Fields (00:34:21) – What’s the first baby step here? Maybe the first baby step is just to say hi. Maybe the first baby step isn’t even that. It’s just a DM them on an app, or get a text intro, or go out with a group of people where you just know that they’re going to be there and you can have a casual zero pressure conversation, and maybe the next thing after that, it’s like, oh wow. Like that was actually kind of a cool conversation. It seems like we both clicked. And then maybe you start to message each other. Maybe. So what we’re doing effectively without even realizing it. And so often we do this in starting new relationships, whether it’s a personal one, an intimate one, a romantic one, or even a business partnership is the way that we feel more comfortable stepping into it, even though we have very low confidence it’s actually going to work out in a really big, long term way, is we chunk the uncertainty in the stakes into little things, and those.

Jonathan Fields (00:35:14) – That technique of chunking helps make us brave in small, incremental, bite sized pieces until eventually we get to the bigger, longer term ones. And by then we’ve built our sense of bravery, and we look back on a body of evidence, a body of proof that these things can, in fact, work out for us. And it helps us keep to take that action even when, at the end of the day, we are never promised that anything is going to work out or sustain long term, even when it does. So that’s the whole idea of chunking stakes and uncertainty. There are a couple of other techniques that I found can be really helpful in being brave, taking action, and making decisions when we don’t know how things are going to work out, when we have to step into a space of uncertainty, of the unknown. And this is something that I actually wrote about in my book, which is literally titled uncertainty, which is all about turning moments of possibility and opportunity, where there’s fear and anxiety almost organically and naturally associated with them into just incredible outcomes, where we have to say yes to uncertainty and live in the space of the unknown, sometimes for longer windows of time.

Jonathan Fields (00:36:28) – And I started scanning and examining and interviewing a lot of different people in different domains who literally did this for a living, from entrepreneurs to artists to founders to writers, all different people. And what I found was a pattern that was fascinating to me and that was that a lot of these people would go into that space of the unknown. They would constantly say, I’m going to say yes to projects or ideas or things that would have social risks and financial risks and resource risks associated with them, and they’re highly uncertain. I don’t know if I’m good enough. I don’t know if the idea is good enough. Their job was to say yes to that in the moment of time, right? As an artist with a blank canvas, I don’t know if I’m going to be able to create something. I don’t know if I’m going to create something that other people will like or value enough to allow me to sustain myself as an artist, and yet I have to. That is my job to actually go to that space on a regular basis to create in that way.

Jonathan Fields (00:37:29) – And what I found was that this pattern that was so common across all of these people, and I realize that it’s actually a pattern in my life, too, was that they would basically create these completely systematized, automated things in their lives where they knew it was going to happen in the same way every single day. And I call those certainty anchors, and those experiences are moments that regular thing literally allowed them to touch into a level of certainty outside of the work of the space, where they knew it was their job to live in the space of the unknown. They would automate and create certainty around all of the other things, often tiny little consequential things, sometimes dozens in ways that would allow them to then touch into these certainty anchors on a regular basis and get enough of a sensation of grounding and certainty that allowed them to be baseline psychologically. Okay. And then know that they would have that normal, see that certainty outside of that container where they would have to go and float in a groundless state, but they would always be able to touch down into dozens of other moments of uncertainty.

Jonathan Fields (00:38:44) – These certainty anchors. And these were things as simple as wearing the exact same clothes or outfit every single day, or having a rotation where you literally had a week of outfits and you always knew exactly what was coming next. Eating the same foods for literally every meal of the day. Working out at the exact same time in the exact same place, sometimes with the exact same person every day. These are examples of certainty anchors that many of us create. We don’t realize that part of the reason that we’ve created them is because it’s giving us these anchors, these tethers, to certainty and to the known. And that creates enough of a sense of grounding that allows us to float more freely in those spaces where we have to be brave. And that is an incredible pattern that I’ve seen. And in fact, I do it often in my own life. As I mentioned, I am very happy eating the exact same thing for breakfast and lunch every day and not having to think about it, knowing it’s just going to be certain and happen in the same way all the time.

Jonathan Fields (00:39:52) – I would very easily and willingly wear the same jeans and the same t shirt every single day. You look at famous inventors and innovators like Steve Jobs, literally wore the same mock black turtleneck and jeans and sneakers every single day. You see this pattern in so many ways, so experiment with that. And that brings us to the third element of bravery that I found can be incredibly helpful in our ability to do the brave thing on a regular basis. And that’s what I call normalizing, unconfident, action taking. And this most often happens in groups. And the idea is when you are the only one who’s facing a situation where it’s highly uncertain, where the stakes are really meaningful to you, and you’re the only one doing it. That makes it so much harder because you both view yourself and you may be viewed by others. Sort of like the oddball, the risk taker, the one who’s always out there doing that thing. And it’s just, quote, not justifiable. But when you surround yourself, when you surround yourself with others who are also co strivers now, they may be working with you on the same project.

Jonathan Fields (00:41:06) – Maybe you’re in a startup or a company, or a project, or a team where you’re all striving to do something cool and new and different and innovative and you’re all working together. So all of those others around you in that same container with you may be the folks who help normalize the fact that you’re not the only one saying yes to uncertainty, saying yes to the unknown. When the stakes are genuinely meaningful, they’re all in it together. So you’re not the oddball anymore. That has a normalizing effect that allows us to actually feel much more comfortable with the notion of taking action and making decisions in the face of the unknown. But it also doesn’t have to be a team. We can actively bring together people in community to help us have that normalizing experience that allows us to be more consistently brave. And I’ve done that in many different ways in my own life. So, for example, I have a couple of different groups of people and we meet on a regular basis literally every month. In fact, funny enough, as I am sitting here thinking through this and recording, I know that tomorrow I have one of my regular calls with a group of people, and we’ve been doing this once a month for years now, and we are all entrepreneurs and founders and putting ourselves out there on a regular basis, and knowing that I am consistently held in that container of people who are co strivers, not working with me on the same team or project, but we’re all doing similar things with similar levels of uncertainty and the unknown and meaningful stakes.

Jonathan Fields (00:42:37) – It helps to normalize the experience for me. Artists do this on a regular basis by working in community or working in shared workshops or studios where everyone is facing the blank canvas or the blank piece of wood. Or writers do this in writers rooms where everyone is just kind of starting from the same place. So when you either find yourself on a group or team where you’re all working together towards that same thing, that can help normalize the experience. But we don’t have to rely only on that. We can bring together our own people who are co drivers with similar experiences, exploring similar moments and windows and seasons of the need to be brave. Or we can find those that have already been created and then step into those. So those three things chunking, uncertainty and stakes, finding certainty anchors or creating certainty anchors in our day and all the different places that we can, often in the places where we’re not actually being invited to say yes and step into the space of the unknown, and then normalizing unconfident action, taking off.

Jonathan Fields (00:43:49) – And by surrounding ourselves with people who are taking similar actions. Those three things can be incredibly helpful in cultivating the bravery needed to say consistently yes to things that really matter, but we just don’t know how it’s going to turn out. And that brings us to the final, the a part of the ABCs, and that is awareness in need. So I kind of cheated a little bit here by sneaking in ease after awareness or maybe two different things here. But awareness is the ability to see as much as you can the truth of the situation, to become aware of what’s happening both outside of you and within you. And the ease part is the capacity to cultivate ease or equanimity or peace or grace, whatever word you want to use when you are in these moments of elevated uncertainty and stakes, again, all in the name of possibility and connection and impact, the ability to create ease in those moments is incredibly important and powerful, so that just we as human beings who yearn to actually have some level of equanimity and peace so that we can move through these moments.

Jonathan Fields (00:45:09) – And instead of recoiling and being filled with fear and anxiety, we have the tools and the mechanisms to both become aware of what’s happening outside of us and inside of us, with clarity and truth and honesty and the skills to then say, even if I can’t change this or make it more certain, and the stakes are deeply meaningful to me, and I don’t know how it’s going to end. I have the skills to be able to actually find peace and equanimity in this moment. I cannot change the circumstances, but it can change my psychological and physiological response to this moment, and that gives me a sense of agency and control. Even when the circumstances outside of me are not entirely within my control. So the awareness piece here, how do we actually become more honest and aware of what’s happening outside and also what’s happening within us? So there are a couple of different tools that we can look at. Many people actually turn to journaling for this. For many, a daily journal is incredibly powerful at helping them really ask questions.

Jonathan Fields (00:46:15) – And one of the questions is, how do I actually truly feel what’s happening inside of me right now? Am I calm? Am I a peace? Am I freaking out? Am I telling stories that are true or not true? And journaling can also help us look at our external circumstances and be more honest about it and say, the great journaling prop is what’s really happening here. What is the truth of what’s happening here? What is the story that I’m telling about it? Is it true and what is the evidence of it? And these are sort of like variations of Byron Katie’s fantastic body of work, literally called the Work. A great way to actually gain awareness is to journal. For me, I tend to take a different approach. As much as I have said for years, I want to start journaling. There’s something in me that just I haven’t done it because maybe so much of my writing tends to be in different ways, in different venues and outlets. But for me, a mindfulness practice, literally a daily morning mindfulness practice, has been stunningly powerful as a tool to deepen awareness and at the same time give me access to ease.

Jonathan Fields (00:47:26) – So I love my mindfulness practice because it gives me this this sort of like double hit of awareness and access to ease. And part of that is because the mindfulness practice is different from other meditation practices, in that it gives you the skills to notice where your mind is at any given moment in time to increase your awareness. Am I drifting off somewhere else? Am I telling some story about something? Or am I genuinely present and my observing the truth of what’s happening both outside of me and my aware of what’s in me? So it teaches you how to train your awareness. It also teaches you how to notice what you’re paying attention to in any given moment. Have I spun out? Am I lost in what Tara Brock calls trance in my thoughts and my anxiety and my stories? Or am I here and present and aware in the moment? And then it allows you to choose to drop whatever it is that’s taking away from the present moment, that is taking away from truth, away from the reality. And just bring yourself back to what is happening in the moment.

Jonathan Fields (00:48:36) – And I found that this actually is an incredible practice, to be able to both become more aware of what’s really happening, the reality of what’s happening both outside and inside of you and to be able to keep touching back to a place of ease. But I want to add one more practice here that is incredibly powerful for me on the East side. And a lot of folks will think about meditation and mindfulness and think, well, I’ve heard about it, I’ve tried it. It’s not for me. I can’t do it, blah, blah, blah, all this stuff. And by the way, I thought the exact same thing for many years, including, if I’m being honest, some of the time where I was literally teaching yoga and meditation, I struggled so much with the meditation side. I used to find a lot of my meditation in movement, and I still do, but I always struggle with a daily seated practice until eventually I was brought to my knees about a dozen years ago and came to it.

Jonathan Fields (00:49:30) – And now it has been a devoted daily practice for me for that entire window of time. And that is a story for another time that I will probably share right here on the podcast at a later date. But this practice has changed me in such profound ways, largely because this made me really present. But part of what I’ve added into that practice on daily basis is breathing practices. And what I found is that whether you feel mindfulness or any form of meditation practice is or is not accessible to you. Breathing is. We all breathe all day, every day without thinking about it. What we know is that we can actually consciously harness and change the patterns of our breath, and that has a very direct connection to our nervous system. It helps to down regulate or up regulate our state. And what we know is that short, shallow, fast breaths up regulate our nervous system. It triggers us into that fight or flight anxiety, high energized state that is very uncomfortable for most of us. The opposite is also true.

Jonathan Fields (00:50:27) – Slow, gentle, especially extended exhales tend to down regulate our nervous system and in turn, our endocrine system and the chemistry that flows through us, sending us into a rest and recovery mode. A calm, peaceful, at ease mode so we can actually think about. Really working with our breath to manage our emotional and physiological state. And if part of what we’re trying to do here, when we’re putting ourselves into moments where we don’t know what’s going to happen, we don’t know what the end is going to be. The stakes are deeply meaningful to us. We’re being brave and taking action and making decisions, and it’s making us kind of uncomfortable, as it does for most human beings, right? The awareness lets us tune into how we’re actually feeling, and then the breathing allows us to change our state almost immediately, literally in a matter of seconds. So if we’re feeling anxious or tight, what we can do is slowly, just literally sit and close your eyes if you want and slow your breath intentionally.

Jonathan Fields (00:51:34) – Box breathing is something that a lot of people talk about is being very effective here, and that’s effectively just saying to yourself, there are four elements of breath. There’s the inhale, there’s the pause after the inhale, there’s the exhale, and there’s the pause after the exhale. So breathing isn’t actually just the inhale. And out here. There are the four elements. Box breathing invites you to basically make each of those slow and equal. That’s why it’s called box breathing. Sort of like four equal sides of a box in your breath. So if you think about, well, let me actually take my breath and try as an experiment, what if I inhale for a three count pause for a three count with an open throat and no pressure against the glass? Exhale for three and just pause gently with an open throat and no pressure for three. So that would kind of feel or sound like inhale two three pause two three. Exhale two three pause two three. And that can be incredibly effective in a lot of ways for a lot of people.

Jonathan Fields (00:52:39) – And the final way that we actually think about doing this is bringing it all together. So those are the really big tools that I like to think about in the context of taking unconfident action, where we want to be brave because there’s tremendous possibility and opportunity on the other side, but we’re not confident. And instead invite yourself to learn to cultivate the skills of the ABCs awareness and ease, bravery and conviction that will allow you to then say yes to these moments of profound possibility, without waiting for the magical fairy dust of confidence to drop into your lap, which for so many of us will never happen. So I hope you found that valuable and interesting, and you use and cultivate these ideas and these skills. Just start saying yes to these amazing possibilities in your life. So I hope you found this useful and interesting. As always, I enjoyed going deep into topics on these solo episodes. If you like this, if you want more, let us know. We’re happy to explore different topics, and if there’s a topic you want me to dive into, let us know that too.

Jonathan Fields (00:53:45) – And of course, if you haven’t already done so, please go ahead and follow. Good life Project in your favorite listening app. And if you found this conversation interesting or inspiring or valuable, and chances are you did. Since you’re still listening here, would you do me a personal favor, a seven second favor, and share it? Maybe on social or by text or by email? Even just with one person? Just copy the link from the app you’re using and tell those you know, those you love, those you want to help navigate this thing called life a little better so we can all do it better together with more ease and more joy. Tell them to listen, then even invite them to talk about what you’ve both discovered. Because when podcasts become conversations and conversations become action, that’s how we all come alive together. Until next time, I’m Jonathan Fields signing off for Good Life project.

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