The Power of Play in Life and Business with Jason Goldberg
23 Sept 2025 · 47 min
Podcast episode (I Heart My Life, ep. 207) hosted by Emily Williams interviewing life coach and business mentor Jason Goldberg. Jason recounts a childhood shaped by single-parent upbringing, lifelong struggles with weight and mental health, a 15-year tech career (first job at 17; director of engineering/operations), and a 2009 turning point when a bank card decline (four fast-food charges) catalyzed his dive into personal growth. Influenced by books and coaches (notably Steve Chandler and Byron Katie), Jason moved from tech into speaking/coaching (full shift by 2014). He developed the Playful Prosperity program (teaching how to be high-performing without excessive seriousness), prototyped content via 30 days of Facebook Live, and later shifted focus to coaching other coaches. Practical frameworks he shares include the "three Bs" for enrollment conversations — Booked (come from having enough clients), Blank (no agenda; hyper-present), and Bus (treat each call as if it could be the last). He discusses service over ego, covert contracts, maintaining playfulness in business, and a major personal failure (a 12-year marriage ending) that became formative. Episode closes with Jason's advice: identify the impact you activate in others (his: joy activation) and double down on that.
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Hi, I'm Emily Williams, the founder of the top success and personal development company for driven women called I Heart My Life. I grew my company from $442 to seven figures in my first 18 months, and since then, it's become a movement for women who know they're meant for something big and refuse to settle. At I Heart My Life, we operate with the belief that anything is possible and no dream is too big. We're all about combining business strategy, deep mindset work, high practices, money tips, and a whole lot of lifestyle to help you get the results you deserve in all areas of life. Because after all, we only get this one shot. This is your one stop shop for all things inspiration. So grab your favorite drink and a pen and a notebook and get ready to be inspired. Oh, and if you're not a member of our community, go to iheartmylife.com, join and receive all of our emails and announcements. And while you're at it, copy and paste this episode link and share it with three friends. Now onto the episode. Hey, it's Emily Williams, the founder of I Heart My Life and your host of the I Heart My Life show. This is episode 207, the Power of Playful Prosperity and Life and Business with Jason Goldberg. So Jason is someone I met about a month ago when I hosted an event in Austin, Texas, and he's someone I immediately warm to because of his incredible personality and just his welcoming spirit and energy. He's a life coach and business mentor, but he's so much more than that. In fact, on his Instagram profile it says making personal growth less personal growthy, if that tells you anything. And his podcast is called the Jason Goldberg Is Ruining Podcasting Podcast. So today's episode is full of so much joy and play and fun. And Jason also takes us back and shares his incredible story of completely transforming his life and his body. He was someone who at one point was over £300. He was burning the candle at both ends as an incredible employee in the corporate world and the COR in the tech space. And now he's somebody who obviously is doing something completely different. And now he's helping other people to transform their life as well as their business. So today's episode is quite a treat. It is jam packed full of tons of incredible content. So make sure you grab something to take notes with because you are going to need it. Let's dive in. This episode was sponsored by the I Heart My Life Mastermind. The I Heart My Life Mastermind is perfect for you if you already have a business and you're looking to scale. We cover tons of different topics. We cover marketing strategy, revenue planning, team processes, everything you need in terms of mindset, high performance, really taking care of yourself as well as your business, events, publicity. We literally have seven coaches under one umbrella to support you and give you the answers to all of your burning questions. We host regular weekly workshops where you get your personal questions answered. We have retreats, you have a private Slack channel where you get to ask questions 24 7. You have an extensive resource bank that helps you put in place our cash method in your own business and much, much more. This is one of the most inventive programs around. I don't know anyone else offering the service that we provide. So if you are interested in growing your business and transforming your life, definitely book a call with us. To learn more. Go to iheartmylifebooking.com and learn more about the I Heart My Life Mastermind. Welcome to the I Heart My Life show. Jason, I'm so excited to have this time with you.
I'm so excited to be with you here. It's not often that I meet somebody offline first and then online, but we got to do that cause we got to meet in Austin not too long ago, which was super fun. And I really enjoyed hanging out with.
You and James Same and I'm gonna be hearing your story for the first time alongside of our audience. So I'm excited to learn more about your background, but I really wanted to have you on the show because immediately James and I, when we first met, you felt like you had such a great energy and just you're so vibrant and you bring so much to a conversation in person. I know you'd bring so much to the show.
Well, I mean, I'm just ridiculously caffeinated all the time. That's what it is. I mean, if you catch me without coffee, I literally look catatonic and comatose. So luckily though, I KN that this was happening today. So I made sure to have my bulletproof ready to go. But no, I appreciate you saying that. I felt the same way about you guys and I'm excited to dive in.
Cool. So I always ask people tell me about the story behind the success. So take us back to where it all began.
Yeah, I think it's more the story behind the failures and then the success is kind of what was left over. And it's so funny because I don't even see myself as successful. And so maybe we need to turn this into a coaching session for me. But it's an interesting thing. I mean, I was raised by a single mother, single Jewish mother. So she can hear everything we're saying all the way in Florida. And I'm an only child, no brothers, no sisters. And dad left my mom when she was pregnant. Like, never seen him. He could walk by me on the street, I wouldn't know who he was. And so it was always just the two of us. And so that was great in so much as we had a very close relationship and I kind of was forced to grow up a little faster and to be more responsible and to kind of develop more of these kind of adult emotions early on. And that also can kind of be a double edged sword. Right? It can be a thing where you don't necessarily know how to process those things or how to manage those kinds of emotions. One of the ways that I dealt with that and I coped with that in growing up. And this is something my mom did as well. So it's something else we bonded over was food. My mom didn't really cook. I always say my mom knows how to make one thing really well and it's reservations. And so there was a lot of fast food and pizza and things like that. And so from a very young age, I struggled with my physical weight. So I was the chunky kid by kind of first grade, by high school, by 15, I was 250 pounds. And then in my late 20s, I had gotten up to 332 pounds. So that was kind of a reoccurring thing through my whole life. And that was pretty prevalent in my family, is that food was there when we were celebrating, food was there when we were sad, food was there when we were bored. Food was kind of the go to soothing mechanism. And so that kind of that weight and being a kid especially that's overweight and getting a lot of ridicule and getting picked on. And I don't at all minimize people's experience who were skinny because skinny people also got picked on. Kids can find anything to pick on. And so it really. I developed a lot of anxiety early on in life. I was always very stressed out. Even as a kid. I had a lot of depression. I was on antidepressants from the time I was kind of about 15 or 16 into adulthood. A lot of suicidal ideation, suicidal thoughts. And it was all kind of going back to this, not feeling enough, not feeling lovable and just not feeling like I had a lot of value in the world. And so what I ended up doing, for better or for worse at the Time was one of my natural tendencies. I've always kind of been kind of the class clown, center of attention, and I like to make people laugh. And I think I developed that in part because my family was very much that way. Uncles who were always making jokes and stuff. But I realized that if I could make people laugh, that humor felt like connection. And that humor made me feel like there was something I had to offer people. And so I really leaned into that. And then I also really wanted to have connection with girls, and I was not a romantic interest for them at all because I was the fat kid. But if I would sit there and really listen to them and really connect with them and be empathetic to whatever was going on in their world, even if they were just talking to me about my friends that they had crushes on, that allowed me to feel connection as well. So I say all this to say that my shadow of being really stressed and depressed and anxious and all that, these things, but desperately wanting to feel enough and desperately wanting to feel connected is what had me develop and cultivate these parts of myself that are natural parts of us. But I mean, really intentionally focus on humor and empathy, which has been a guiding force in my entire life ever since. And it's the way I connect with people and it's the way I serve, and it's a part of my business. So that's kind of like my very early on, kind of like, growing up story. And then I can talk about the professional side of that, if you want to dive into that or just want to see if you have any questions about that stuff.
Yeah. Thank you so much for sharing that. And I think it's so interesting to look at our childhood and identify the areas in which shape our adulthood. And we do a lot of this work within I heart my life, where we recognize we're bringing in certain stories and tendencies that are not only ours, but from previous generations. And the way that our family has shown up for decades, we bring that into adulthood, we bring it into our business. And I always say there's so much that we can learn from from that trauma, and there's so much that we can do with it that's good, but we really need to process it and figure out, okay, what do I need to release? And then how can I start to shift it and serve from a place of being whole and healed? And one of my clients has a great phrase. She says, you share from the scar, not the wound. So making sure that you're not sharing from a wounded place so I think that's really, really powerful and I appreciate you being so open about that.
Yeah, I think we need to do.
This because I think unfortunately there's a big misconception in the personal growth world, especially if you're a coach, that it means you have it all figured out, whatever the hell that even means, and that you are somehow immune from the human experience of suffering or stress or anything else. And I think that that's a disservice because it sets up unrealistic expectations for the people that follow us. So this is not about using vulnerability as a strategy, which I think a lot of people do sometimes. And well intentioned, I have a judgment about that.
But I think it is important that.
We do open up to share with people. Like, listen, it's okay if you've done 10 years of inner work on this thing to heal from when you were a kid and then you talk to your mom and you get triggered by something, it doesn't mean you fail that personal growth, it's just the human experience. So the more we can be gentle and easy on ourselves and realize that this is part of the human experience, while also understanding the way the mind works, the way the system works. Just like with anything else in the world, when we understand how the equipment works, we can better use the equipment. So it's just kind of holding that paradox of being able to be in both of those places at once.
Agreed. So how did you end up taking the experience, the trauma, all of that, and turning it into a professional career? What was your path on that journey?
Yeah, accidentally so, especially with what I'm doing now. So I got into tech very early on. Really early on. I was just a nerd. I just geeked out on computer stuff. I had an uncle who was kind of in tech and he brought me in at a really young age and started having me tinkering with stuff. So I got into tech pretty early. I got my first real technology job at 17 and then I spent the better part of 15 years in that industry, the last seven of which I was director of engineering and operations for a tech consulting firm. So I was in tech consulting the last seven years of my corporate career. And that was when I had this kind of big shift into personal growth because I had never been a part of personal growth at all. I was just an angry, depressed, stressed out human. And even though I was making well over six figures in my 20s and I had what felt like a perfect relationship at the time and had the house and the car and all the things I still just my experience of life, I didn't really feel like any of that made me happy, at least not for too long. And then it wasn't until I had this experience, which is kind of the first chapter of my book, Prison Break, which is all about breaking out of the prison of the mind, where I tried to make a purchase on Amazon for socks. Like I like funky socks, like novelty socks. And I went to make this purchase and my card got declined. And I wasn't sure why, because obviously I had enough money in the account for an order of socks on Amazon. And I tried it multiple times. Card kept getting declined. And I had so much anger in me back then that I just like stormed out of my office. And this is when I was still in my corporate job and went out in the lobby and I called the bank and I'm just ready to just lay into them and scream at them because this is not working. And they essentially tell me that my card is been cut off because of potential fraudulent activity. Instead of being happy and grateful that they're protecting my account, I got even more upset because that's just what I did. And I demanded to know what these fraudulent charges were. And it turns out that there had been four fast food transactions in one day. And they assumed that meant somebody had stolen the card and they were testing it because nobody would eat at four fast food restaurants in a single day. But I had eaten at four fast food restaurants in a day. And so it was that day I say, that's the day the universe cut me off. When a multi billion dollar bank said, we're taking away access to your money until you make a change in your life. And that's where I really started diving into personal growth. So 2009 ish is when I started getting into personal growth. I left my last corporate job in 2011, had a couple other startups. I had a transportation technology startup and then I had another startup in partnership with NASA and the space shuttle program while I was in grad school. And through that entire thing, I kept coming back to personal growth and I kept coming back to how much it was transforming my life from being coached and reading books and going to workshops and seminars and just seeing this change in my life of realizing Personal Growth 101 to all of us here and whoever's listening to this, but that I can actually play a role in creating my experience of life. And it was just like if you go to a restaurant you love or you see a movie that moves you, you can't shut up. About it, you got to tell everybody. And that's kind of how I decided to let go of all the tech related stuff I was doing and move into speaking and coaching in 2014. I've been doing that ever since.
Wow. Okay. So there's a few things I want to ask you about this. So 2009, you have this moment where the universe cuts you off. What is your first step into personal growth? Did you already know of personal growth? Did you have a coach in mind? Did you have a book that you had purchased but never read? What was that first step?
It's a great question. I had none of that. All I knew was that there were people around me, including my now ex wife, who had been through far worse traumas than I had and yet seemed to have a different outlook and a different perspective on life. And so being in technology, the way my mind typically works is reverse engineering, right? If there's like some big technical thing that we're trying to do, let's find someone who's done it and just reverse engineer and do the same steps and it works in a logical environment like technology. It's not the same when it's the mind, but there were still clues. And so what I saw there, that was the common thread, is that those people read books on personal growth. So I'm like, all right, cool, I'll get a book on personal growth. The first book I got, because everybody was saying, you need to read it. It was just like the thing to do was think and grow rich. And I hated it. I hated that book so much. And I'll tell you why. It's because I was so closed off to the idea that I could be anything but a prisoner of circumstance in my life. The thought that circumstance did not dictate my happiness or sadness was so foreign to me that as I'm reading the book, he's doing this thing. If you remember the book and maybe you remember this as I'm saying it, he keeps saying throughout the whole book, by now you've probably gotten the secret of what I'm pointing to. And I'm like, you son of a. No, just. Why are you saying the. Why don't you just tell me what the secret is? And anybody who would read that that had some openness and weren't so closed off would say, yeah, I see the secret. It's your thoughts, create your reality.
I get that.
I didn't see any of that. So I so hated that book initially. And it wasn't until I kept diving into personal growth and really, one of the first people that I think really, really hit home with me, somebody who then became my coach and is now still my coach and my friend and we've created projects together, is a guy called Steve Chandler. I don't know if you're familiar with Steve's work, but Steve wrote a book called Reinventing Yourself that I read. And that was the one where I finally started to get like, okay, I really can play a pivotal role in my experience of life.
And what do you think it was about that book that spoke to you and connected in a different way?
Yeah, it's an amazing question. So it's so funny you say that too.
No one's ever asked me that.
And it's a big part of, I think, why I do what I do now. Steve was the first person I saw that brought a conversational light, not so serious perspective to personal growth. Because it's very, very commonplace to be like, you're gonna do this shadow work and you're gonna go deep and it's gonna be painful and your friends aren't gonna recognize you and your family's not gonna wanna be around you. And I'm just like, crappy sales pitch guys, really? And it's maybe true. It's not that it's not true, but it just, it didn't feel accessible. And Steve is just one of these people who is able to do that. And that became a big part of me giving myself permission to do the same thing. Because again, humor being my thing, I think that's probably why it resonated, is because humor is a part of who I am. And so humor and levity and lightness can really be a conduit to transformation. And so that's what I got from that book. And it's how I teach and coach in the world now.
Amazing. I love that. And so what were some of your first steps after reading the book? What did you do to actually start to transform? Because, I mean, I want everyone to remember like you were deep into a thriving career, you were in a marriage, you had weight that you eventually wanted to lose. What was the process to that transformation?
Yeah, it's really interesting because I know from my own personal experience and especially being in tech, that I've always looked for and still to this day, many times look for the doing steps. Like, I want the three step process for transformation. And it's one of these things where insight is so powerful, that insight alone can be transformative.
Now if you get the insight and then you go back and lay on.
The couch again and keep eating bon bons. Then it's. Maybe it doesn't work as well, but real insight, real insight is transformative. And so, for example, Byron, Katie, who's another one of my top spiritual teachers who I know in my top three, she's right up there and she tells this story about one day, she's walking kind of in a deserted area and she comes across this rattlesnake that's there and she freaks out, sees all these pictures of the future where she gets bit by the rattlesnake and she gets, you know, the poison's coursing through her body and she's by herself and she drops dead and her body decays and nobody ever finds her again. And she has all these stories that just immediately run through her head without even trying. She's just being thought. She didn't create the thoughts, she's being thought. And upon slightly closer inspection, she notices that it's a coiled up piece of rope.
Right. It's not actually, it's not actually a snake. And so at that moment, she didn't need a three step process to deal with her issues with rope. She simply saw, oh, what I thought was a snake is actually a rope. My work here is done. So a lot of it was just allowing myself to sit in the inside. Doesn't mean there weren't steps as well. But a big part of it was me sitting in the inside of seeing something that made sense to me and then going out into the world and testing those insights as much as possible. Like being a skeptic, I wasn't like, oh yeah, this is great, it's going to work all the time. I was totally a skeptic. And so I said, I'm going to go out and test it. And so it was just testing the inside of like, okay, in this moment I want to blame this person for this thing. How am I maybe creating some part of this conflict with this person? How am I showing up in this place and just trying to practice the insights that I got from the books that I was reading and the coaching.
That I was having done.
Love that. So being aware and also being curious about what's going on.
Yes. Curiosity is such a big thing. Like that's something part of my kind of mantra that I have for myself. One of them is that I am rewriting my stress response to be curiosity and creativity instead of impulsivity and reactivity. Right. So my default growing up was like, if something went wrong, I would get reactive, I would get impulsive. I want to reprogram that stress response, to get curious about what's going on and then get creative about how to move through it.
Love that. And so at what point did you decide, okay, I'm going to take all this growth, everything I've learned, the personal development, and I'm actually going to turn it into a business and I'm going to move past the tech stuff, be my own boss. Like, how did you make that decision and how did that happen?
Yeah, I mean, it was scary as hell to leave my corporate job and then I had the two other startups before I got into coaching, so I got to kind of cut my teeth on that.
But they're totally different things than running a coaching business.
Really? NASA's different to coaching?
Just slightly. It's just a very small thing. There's actually some overlap, funny enough. But the interesting thing though is that a coaching business, and for anybody who's had a business that's not coaching related and then moved in, I'm sure they'll get this. And even if you just go into coaching as your first kind of venture, is that it feels like you're selling yourself.
Right?
When I was doing stuff with NASA.
I couldn't get rejected.
When I had my transportation startup, I couldn't get rejected. But now when it's me and it's my coaching and the ego goes nuts, it's a whole different set of things that you have to kind of deal with. So that was a big part of it for me. First and foremost is like really understanding that nobody's ever saying no to me any more than they're saying no to dessert from a server at a restaurant at the end of a meal, right? The server doesn't go back in the kitchen and somebody says no to the cheesecake and go, oh my God, what.
Am I doing with my life?
I'm not enough. I gotta figure this out.
It just doesn't happen.
They're just like, you want dessert? And they're like, no, we're good. Cool, no problem, I'll bring the bill.
It's not that big of a deal.
So there was so much of, of my people pleasing that I had as a kid and my desire to be.
Liked and all these things that ego based.
Socially acceptable kind of thing, trying to be compliant, trying to get people.
To like me, that separated me from.
Actually being of service. So instead of trying to please people, it was really a matter of how can I really focus on serving people. So that was such a big thing is going from ego to service and Going from pleasing to serving people, really, truly serving.
Did you have a moment where you're like, oh my gosh, I'm all ego here, or this is really affecting me, how people are saying no to me and then did you make a shift? Was that how it worked?
Yeah, I mean, I didn't realize that.
It was ego at first, but I.
Just, I realized that I would get really, like, irritable and almost like resentful.
Of the people that I was talking to and trying to help. And I'm like, don't you see I'm trying to help you? And it just, it was just, it was. There's so much ego and it's well intentioned. It's like, you mean well. But yeah. So I kept seeing it over and over again, and I'm pretty sure it was actually one of my first coaches that reflected it to me when I brought this kind of, you know, just being really. Yeah. Being irritable, being angry, being resentful, and really having the coach slow me down and say, you know, if you're doing something that is as Dr. Robert Glover has a book called no More Mr. Nice Guy, which is a great book. Whether you're a man or a woman, it's a great book.
But he talks in there about something called covert contracts.
And covert contracts is when you do something that seems well intentioned and loving.
And helpful and kind, but in the.
Back of your mind, you really want something to be reciprocated in return, and that is toxic to building a business, especially a business that has so much intimacy involved like coaching does.
Interesting. Yeah, that's really manipulative at its core. It's fair.
Yeah, it's very. And it's not manipulative, like vindictive, malicious. It feels nice and sweet, but it's absolutely still manipulative.
Yeah. Interesting. Okay, so this service piece is really key and we work with a lot of coaches at I Heart My Life. And people are always asking, how do I make more money? How do I get more clients? And I remember I had a conversation with a colleague years ago and he was completely in debt. His business wasn't growing, he didn't know what to do. So he decided to remove any idea of, okay, I need to make. Make sales and just focus on service. So every single day he was showing up on Facebook Live. He did this for six months, eventually offered something for people to buy it sold out. Now he has a multimillion dollar business. That's a very short version of the story, but that always stands out in My mind as an example of massive service. And what happens when you actually release this attachment to sales or getting it perfect and you're just. Just showing up heart first, ready to give to your community and your audience and the power of that. So what did service look like for you?
Yeah, so I didn't have a model.
For this back then, like a framework.
For it back then, but now I do.
Especially when it comes to having enrollment conversations, for example. Right. Cause that's where if you're having a sales call or an enrollment conversation, that's when all the confidence stuff comes up and are they gonna sign up? Kind of thing. And. And like we were just talking about. People sense that, right? Like, needy is an energy that people sense and they don't want to be around that, especially with a coach. Because when they're hiring you as a.
Coach, a lot of times they're borrowing your belief and your optimism.
And if you are showing up in a needy place, that's not leadership. Right.
Our clients want to be led.
They don't be told what to do.
But they want to be led.
And that's not leadership. So for me, what I finally realized, and it comes down to Buddhist principles and detachment and all these things, but I broke it down into something that I call the three Bs, right? So my three B model, to be super confident on sales calls and enrollment calls, and also to stay in a place of service.
So the first B is booked, right.
And so booked means I go onto this call, this enrollment conversation, with the perspective of, or through the lens of I'm completely booked.
It doesn't matter if you're the coolest.
Person in the world, the biggest vision in the world, the most money in the world, I cannot take you on. It's not possible. But I'm happy to see what I can do in this time that we have together to see if I can help move you forward. And so booked is the first one. The second one is blank. I have to come in with no agenda.
I have to be motiveless. I don't.
You know, in the beginning, when I.
First started coaching, I would never do video calls.
You're gonna love this. Anyway, I used to never do video calls.
I would only do audio because I.
Had seven pages of coaching questions laid out in front of me.
And like, while they're talking to me, I'm like, this. This one's good.
Tell me about your mom.
Oh, wait, that doesn't make sense. Nevermind. Okay, so.
And it was. It was. And in the entire time they're over there just wanting to be seen and heard and to have something that could potentially be helpful. And I'm sitting here saying, I can't help you right now because I'm trying to help you. So I. Give me a minute. And so blank was really going in saying like, fine, if you want to prepare in some way or you're dealing with somebody who's in a specific industry and you want to do a little bit of research in the industry, fine, but show up blank and then be willing to be so hyper present that you just respond to what shows up.
Right. You don't need to be right.
You don't need to be perfect.
You just need to really, really listen.
And help people see what clarity looks like for them. So that's blank. And the third one, this is where it gets a little morbid. This is the one where I lose followers every time I share this. So hopefully we'll see what happens here.
The third B is bus.
B U S bus. And what this means is that I want to go into an enrollment conversation.
And I want to pretend that I know, but they do not know that.
Right after this conversation, they're going to.
Walk outside, get hit by a bus and kill.
Right? And so if I know, but I.
Can'T tell them either, but if I.
Know that they can't be my client.
I want to make sure that this.
Last conversation they have is the most powerful conversation they've ever had in their lives.
Right?
There's no way they can be my client. They are literally going to perish from the earth, but they're going to get hit by that bus, feeling really, really good about what's possible in their life. Right?
And so when I come in with the book Blank bus, it just has.
Me show up in a place where I'm highly involved, highly engaged, highly present, highly attentive, but low to no attachment to any particular outcome or result.
Oh, my gosh, that is brilliant. I'm obsessed with that. And like, the bus piece for me adds another element. You know, I think so often we think we have all this time, and I hope that we do, but there's no guarantee. And so it's also like, from my perspective, I know you're not telling them they're going to be hit by a bus, but if we're looking to inspire people or display belief about what they're capable of, now is the time to do it. Now is the time to take action and for them to move forward to make that transformation. Because we're not guaranteed A certain amount of time. So that is awesome. My community is going to be obsessed with that. Thank you so much.
My pleasure. Yeah. Hope it's helpful for them.
That's awesome. So what were some of the first programs you developed or what were your services that really kicked things off for you?
Yeah, so I started off just doing one on one. And I remember I had my very first coach. I talked to him and I sat down. This is 2013, and he was a life coach, but he had never helped anybody who wanted to build a life coaching business. And so I asked him like, hey, I'd love to coach with you, but I'd also like to build a business. He's like, cool. I've never done it before, but I'm happy to see what we can figure out. And he was the first one where I came in, like, high energy, overeater, talking fast. Like I do hand motions, going crazy. People that are listening to this have no idea what that means for me, but I'm very expressive and I'm like, I want to do this and I want to build this program and I want to have this book. And he's like, listen, sure, that's all great stuff. And I wonder if it would be more powerful and more important for you right now to really focus on getting a level of. Of a track record and of confidence around your coaching process first, like really slow down and serve the people in front of you. And then as a way to manage your time and energy and as a way to scale your impact and your revenue, then look at other things you can do. That's not the only way to do it. That was just the way that. That was kind of presented to me and it felt good. So I did just one on one coaching for probably the first, I would say probably close to the first two years, year and a half, two years that I was a coach. And then I decided that I wanted to create some kind of a program because I realized, and this is actually, this was a big realization for me. And so if anybody watching this is a coach and you feel like maybe you're struggling because the one on one doesn't light you up as much, it's possible that you are a teacher who coaches. And that's a really important thing to think about because I never gave myself permission to do that. Everybody told me, like, well, a coach does this. They ask powerful questions and then they shut up and they let their client come to their own realization. And I'm sitting there sometimes like, God, I got this story. I Got this insight, I got this thing that I think could help. But no, that's not what we do as coaches. We are purely there to be a mirror and hold space for them, which is great and so true. And if you are somebody who loves to teach and loves to share wisdom, you can integrate those two things and it's okay. And so when I finally gave myself that permission to say, oh, you're not a coach, you are a teacher who coaches, that was so powerful for me to give myself permission and say, okay, I want to do something that does impact more people and allows me to be more in a performance kind of place. Right? This teacher kind of a place. So the big thing that everybody had come to me for and that I had become known for was playfulness, was having more joy. And so I decided I wanted to create this program called Playful Prosperity that everybody told me they hated the name. And I said, I don't give a crap because it resonates with me and it has alliteration, and alliteration is amazing. And so I created this thing called Playful Prosperity. And essentially, I tell people, anytime you create a course or even modules within a course, always think about what the before and after gap is. And so for my course, the before was, I think I have to be serious in order to be successful. And the after gap was that I can be just as high performing and highly productive without being successful serious. That was my guiding principle. I was like, okay, what can I put in here? What can I create? What can I share? What can I teach that inches people closer and closer to not being so serious, still being sincere, still being devoted and committed, not just being flippant and not having a plan or anything, but to do it with less attachment and less seriousness. And so I decided to create this program. And funny enough, the person you mentioned that decided they were just going to show up and do all the things very, very similar to me. So I was going to create this program, and I had all the fears in my head and a bunch of people telling me on the side, like, well, you know, you may not be able to sell a course if you don't have a big audience and all these different things. And I said, okay, that's kind of scary to put all this work into a course, and then nobody buys it. So at that point, it hadn't been too long before that that Facebook Live had finally opened up to us Normies. Remember, it was just celebrities and stuff in the beginning. Every week I would check, and I was like, I want to go Live so bad. It feels like it'll be so fun. And I was terrified, but it still seemed fun. And so when it finally became available to all of us and I knew I wanted to create this course, I had mapped out all these different things that I thought would be helpful to have in the course, but I had no idea, right? And so I said, okay, here's what I'm going to do for the next 30 days. Every single day, I'm going to go live and I'm going to teach these concepts. Now, maybe not to the full depth and extent that I would in a course, But I mean, 30 minutes to an hour, Facebook Live, where I'm teaching a thing. And then at the end of the 30 days, I looked at the things that got the highest engagement. I deleted those from Facebook Live, and I knew those would resonate with my audience when I taught them more deeply in the course.
Brilliant.
And it works so well. And there were some things that maybe didn't get as much traction, and I was like, I don't care. That needs to go in the course, and you can still do that. I wrote my book the same way my book was. I sent out newsletters to my list every week. And the things that resonated, I. I put aside for the book. The things that didn't, for the most part, I didn't put in some of them, I still did because screw them, it's my book. But putting that stuff out in the world and getting. It's like pre selling, but it's really just pre vetting that your content is something people want to see. And then I went and put like five or ten bucks behind each one of those Facebook lives to boost them, just to get a little more traffic so that I would have a better sample size of whether it resonated or not. And that's how I created my first course.
I love that. Oh, my gosh. Amazing. And is that something you still sell to this day?
So, funny enough, we stopped selling it. I didn't want to stop selling it, but we shifted into something else that required more of my attention. We actually gave away 500 copies of it during COVID And I also gave away some free group sessions with that program just to kind of support people. But it's something I definitely want to bring back. And it's something that's just been. It really is just. I love it. It has nothing to do with building a business directly. Of course. It has everything to do with building a business because it's. That's the interviewing stuff. But when I shifted more after three or four years of not coaching other coaches, when I shifted into that, I really went all in on that and playful prosperity went on the back burner. But we're talking about ways to bring it back because I just, I love it so much.
Amazing. So one question for you that I'm really curious to know is what has been the biggest challenge from your perspective in terms of building a business or platform?
The biggest challenge, I mean, there's so many. That's the other thing I think is a challenge in this industry is not everybody, but some of the people well intentioned and I love them. And if it's their truth, I'm happy that it's their truth. But that business should be something where it should be in such flow that it never takes any effort and it's an easy thing that happens in your sleep. And maybe that's the experience for some people. My experience is that anything that matters takes effort. And so it's been a lot of effort. But I think, I think the hardest thing for me personally is less of like logistical or tactical thing. It's me losing my spirit of play in the business building process. And I was thinking about this the other day and I was talking to my team about this is that in the beginning when there was like nothing to lose and I hadn't built the business up and it was a new thing, it was a little baby, I was too naive and too stupid to know that there was a possibility it wouldn't work. Right. Because I was just so excited. I was just playing, I was just having fun. And then the more successful I got or the more people we reached or the more money that was made or whatever else, it seemed like I started creating a story in my head that the stakes were higher, that there was more to lose. And that robbed me of my playfulness and my joy. That was such a part of who it was that I was in the beginning. And there's this saying that I love that one of my mentors said a long time ago to me is there was something that was working so well, I stopped doing it. And that was the thing for me. What was working so well was being in this spirit of play. And what wasn't working well for me was when I started taking the business too seriously.
And so how do you maintain that spirit of play on a regular basis?
Yeah, I mean, there's things you can do on the outside, right? Of course. For me, I really want to make sure that my business is not the center of my universe, because I have this belief. And this was something that actually came up, funny enough, when I went on a trip one time with Ajit and Ita, and Ari was there. Their little baby Ari was there. He was like a year, year and a half at the time. And there was a pool at the Airbnb we were at, and I was on Uncle Jason duty. And so he's running around and I'm trying to make sure he doesn't fall in the pool. And all weekend, I wasn't babysitting him all weekend, but all weekend there were other things that had my focus. And I realized that on Monday morning, my anxiety level was way lower than it normally was. And I realized that I had made my business the center of my universe. And anything that we make the center of our universe, whether it's our businesses, our relationships, even our kids, like, even if you have children, anything, you make the center of your world the center of your universe, you are going to spend all of your energy making sure that it is doesn't fail or fall apart, and that doesn't leave room for anything else. And so I decided that my identity, the new identity that I was going to start living into, was somebody who does not make anything the center of my universe except my own experience of peace and ease. So when I start getting stressed out, I ask myself, what am I making the center of my universe right now so I can get really hyper present and figure out what it is that's doing that. And then I ask myself, what would it look like to bring 5% more peace and ease into my experience right now? And that may be some deep breathing, it may be some meditation, it may be some working out, it may be some reading, it may be whatever. But it is just this constant checking in of, am I making this thing a bigger deal than it is? Am I taking this too seriously? And the more I can kind of slow down and get into that present moment, the more the natural play and joy starts to shine through again.
That's beautiful. Thank you for sharing that.
Yeah, my pleasure.
So we started this conversation with you telling me that it's been more about the failures than the successes. What has been your most important failure?
Ooh, most important failure. I would say my marriage ending was my most important failure. And I'll tell you why. We were together for 12 years. It was a really great relationship. That the reason primarily that it ended is that she became aware that she had actually been pushing down her true sexuality and she was a lesbian. And it took 12 years to kind of get to that realization. And I'm so happy for her that she now gets to live the life that she wants to live. But the way it happened, she came to this realization, and she realized she had been pushing it down for so long and that she needed to make this decision and really be true to herself. I was gone for two weeks. I was traveling around, doing a kind of a little speaking tour and working with clients. And so this was in the middle of the two weeks I was gone. She FaceTimed me when I was in an Airbnb in Denver and told me that she was a lesbian, she wanted a divorce, and she was moving out in two days. So that by the time I got home, she was completely gone. And I still had another week of things that I had committed to, speaking engagements, all these things all over the country. And I was devastated. Like, 12 years. I did not see this coming. I knew she was kind of struggling with the sexuality stuff, and we were working on that with her, but I did not think she was going to over FaceTime, say, I'm done, and I'm leaving before you get home. So now I have to go on for another week and speak at all these different events and be the joy guy and be the play guy. And I tell anecdotal stories about my wife on stage that are a part of my keynotes and all these things. And so the reason I say that it was my most important failure is because that was the time that I realized that if I choose to, I can give myself a challenge, which I did. For those next five days that I was still traveling, the challenge to myself was, for the next five days, can I channel every bit of pain that I'm feeling into the service of others?
Right?
Every time I start feeling this pain, can I go find somebody to serve and try to make their life better? Now, this doesn't mean don't deal with your crap and spiritually bypass. I was going to go home, and when I went home, I fell into a puddle and dealt with all the stuff. But for that week, could I do it? Because the challenge with entrepreneurship in general is that there's this beautiful ideal and this glamorized, pedestalized experience of being an entrepreneur that changes all these lives and makes all this money, which is all great as long as your preferences are being met, right? But what happens when your preferences aren't being met? What happens when things start being way harder than you expected? And you say, I didn't sign up for this. I signed up for transformation I signed up for growth. I signed up for fun. I signed up for money. I didn't sign up for this. I could have easily. And I wouldn't have found any shame for this or self judgment for this either. I could have said, I didn't sign up for having my wife leave me while I was on this thing. I quit. I'm done. But what I realized there is that it wasn't about what I signed up for. It was about why I was here. Right. What was I really doing here? Was I only here to speak and transform lives when that was convenient? Or is it really something that I felt true meaning and connection to? And so that experience, had I not had that experience, I don't think my convictions would have been tested to the extent that I know there's nothing that I've been through that I haven't gotten through. That's the only evidence I have in life. And I carry that going forward.
Thank you for that reminder that resonates so deeply with me. And I think if we allow them to, failures do show us what we're capable of and create that strength and resilience. And also show us, like you said, what are we really here to do? And ultimately, you're teaching, you're speaking. It's not about you. It's about service, it's about helping others. So we got to move out of our own way and like you said, still deal with what's going on, but keep that in the forefront of our mind.
Yeah, Absolutely.
Amazing. Well, I feel like I could do another, like five episodes just with you, but I have to ask our final question. We have to end it somewhere. So what is one way that you'd recommend based on your experience? Our listeners can create a life that's better than their dreams, better than their wildest dreams at this moment.
Oh, I love that. I would say to get really clear on. Okay, so another distinction really quickly. I love distinctions. I work a lot on distinctions because it's easy for me to remember this versus that. So when I first started getting into coaching and wanting to build this business, I was trying to figure out, like, what am I gonna be known for? For what's going to be my thing? What can I hang my hat on? What's going to be different than everybody else? And that was very stressful for me because everybody's done stuff and it's like, oh, I'm not as good as that person. And she has way more experience than me and he has a better production value and all these things. And it Wasn't until probably two years into my coaching business that I finally stopped pushing away and ignoring that. People would tell me, being around me right when I would come off stage from Aquino, very rarely would I have somebody come up and say, you are the most intelligent person I've ever heard in my life. Which is all I wanted them to say. I wanted them to tell me I was smart. But what they would say was, I don't know what it is about you, but I feel more joyful and playful just from watching you do what you do. And I kept pushing that away. Yeah, yeah, no, but tell me how smart I am and how the framework was really awesome. That's what I wanted.
Right.
And it finally hit me. I was on a press tour for Prison Break when the book came out and I had this anchor on a morning talk show that I was on. Tell me afterwards. You know, we just. I feel so much joy being around you. And my co anchor said it, and the green room people said it and the AV people said it. And it really landed for me that day that instead of focusing what I was going to be known for, I would focus on what I was going to be known for, activating in other people, giving other people permission to feel. And when I really leaned into that and I realized that was my true gift, joy activation. And I created this kind of one line life plan, one line business plan to leave everybody I meet with at least 5% more joy than I found them. That cleared the playing field and made it very clear what to do and what not to do, who to be around and who not to be around, what to focus on and what not to focus on. So I think that getting clear on what you're known for, activating the impact that you have on people, what you leave behind. When you leave an interaction with somebody, figure out what that is for yourself. Ask people that you love and that love you and that really know you, and then go all in on that, like, really find ways to amplify and magnify that in the service of others in any chance you get. And it will build your life and your business to a place where you will feel tremendous.
That's making me emotional because it just like hits home. And I think it's a way to give yourself permission as well to be all you like. I think sometimes we try and put ourselves into a box and we have to show up in a certain way and we have to resonate with a certain group of people or focus on a certain niche. And I think, like, you Said it's all about what you bring out in people. And I think for me, if I had to choose one word, it's probably possibility and supporting people and seeing what is possible for them, dreaming bigger and going for that thing. And that's really, really powerful to think about it that way versus, hey, I'm a success coach or business coach or a writer or whatever. So thank you for that.
You're welcome.
And I love that for you.
And that shows that's just who you are. And that's the thing, right?
Like you don't have.
That's not a manufactured thing. You didn't say, you know, I think it'll be the most profitable niche if I activate possibilities in people. Like, you can't not. It's just who you are. And there's not like limitless ways to do that. Like, you could be possibilities, you could be joy like me, could be peace, could be clarity, could be truth telling.
Whatever it is you activate in people, figure out what that is.
Go all in on it.
Where can people find you? Because I know they're going to want to follow you, feel that joy and experience everything you have to offer.
I'm usually just sitting on the beach in Venice.
You can just come up and say, hi. No, I'm just kidding. So you could find me on Instagram. I'm hejasongoldberg. Jason Goldberg was taken so I got the most pretentious name I could. Thejasongoldberg. And then my website, especially if you're a. If you go to be competitionproof dot com. That's the word bbecompetitionproof.com There's a free book you can get there on how to build a competition proof coaching business.
Thank you so much for your time. It's been one of my favorite conversations and like I said, I know this is going to be really supportive to our community and they're going to want more. So maybe we'll do more collaborations or something or have you on one of our stages someday because I know that would be such a gift.
I would love it. Thanks, Em. Thanks for having me on. I appreciate it.
You're welcome. I hope you enjoyed this episode of the I heart my life show. Now do us a favor and tell people about this episode. It's truly our duty to make sure that the I heart my life movement is spread far and wide. The truth is, life can be challenging, but it is possible for all women to love themselves and their lives. And while you're at it, send a link to this episode to three of your friends today, or maybe even post it on social media. Use the hashtag iheartmylifeshow. That's ihurtmylifeshow. And if you'd like to help me personally, then please rate and review this podcast on Apple Podcasts. Give us some stars, cheer us on, and leave a review. Because believe it or not, that stuff actually really does help. And I read all of them. Please remember, everything you desire is meant for you. And pop possible. Keep showing up, taking action, and believing in your dreams.
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