
Jen Sincero spent 40 years living in garages and scraping by before she hired her first coach and tripled her income in three months. In this raw conversation, she reveals the identity shift that changed everything and why the scariest financial move you make might be the one that sets you free.
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Lewis Howes
Drewski Live with your legs man.
Jen Sincero
Santa Santa, did you get my letter?
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He's talking to you Bridges.
Lewis Howes
I'm not.
Mrs. Claus
Of course he did.
Lewis Howes
Right Santa, you know my elf Drew Ski here. He handles the nice list.
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An elf?
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Jen Sincero
Nice.
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Lewis Howes
And I wanted to start with.
Asking you a question about money and talking about money for a moment because I Feel like a lot of people are in fear around money right now. They're scared, they're uncertain of what's going to happen with all these things in the world around money and inflation and crisis and all these different things. I'm curious, with all of your research and all of your feedback from your audience with your book about money, what do you feel like is the number one thing that holds people back emotionally and mentally around believing that they are deserving of.
Jen Sincero
Of making the money they want about the deserving piece?
Oh, wow. Well, first of all, I think that a lot of people think it's not okay. Like there's a real morality around making money.
Lewis Howes
Really.
Jen Sincero
Because think about it, we really focus on greed. And when you desire money, it's not the same as being greedy, but I think that we combine those two things.
Sponsor Announcer
And.
Jen Sincero
And so of course, if you decide that you want to make money, it's. You don't tell people. I remember, like, when I was on my path to like, get rich, people were grossed out. You know, it's not. I mean, I always compare it to like, if I was like, I'm going to lose £100. People were like, go. You be like, I'm going to get rich. They're like, you're disgusting.
Lewis Howes
Wow.
Jen Sincero
You know, so there is a real judgment around it.
Lewis Howes
Why is that? If someone's ambitious around making money and creating financial abundance for themselves, why is that?
Jen Sincero
I think because there is an implied morality piece where you're going to do things that are really bad for everybody involved. Like, you're going to money is the main goal, so you'll do anything to get rich. I think there is this really weird perception of that. And I do think that, you know, the news definitely focuses on all the evil that people do to make money. And so, I mean, you know that you rarely hear about people giving lots of money your way or doing wonderful things with money. It really is about how evil the rich are.
Lewis Howes
Yeah, it's more rare to hear people are giving, but you don't hear about it that much.
Jen Sincero
Yeah, not so much.
Lewis Howes
And it's also, here's the interesting thing, because we've also been taught to diminish our giving. Like to not talk about our giving, to make it anonymous. Don't brag that you're giving. Where I actually have started to prescribe to maybe talk 50% of the time about what you're giving. And the other 50% of the time it doesn't have to be, you know, you telling the world about it. But I think when you say, here's what I'm giving, it inspires other people to be generous and giving as well.
Jen Sincero
Absolutely.
Lewis Howes
And it doesn't have to be only money, but it can be your time, your energy, your resources, another way. But I think sharing about it sometimes empowers other people to be more generous as well.
Jen Sincero
I agree. And it also takes away the stigma that you're an egomaniacal fathead and that you want, like, all the praise for being such a good guy. But. And why not? Like, we talk about other good things. We do. It's just money. You know, I've written about sex, I've studied religion. Money is, by force, far the most loaded.
Lewis Howes
The most loaded?
Jen Sincero
Absolutely. It's the dirtiest topic.
Starbucks Announcer
I don't know why.
Jen Sincero
And I don't. I. I really don't. I don't. It's interesting, though. Like, did your parents talk to you about money? You know, I grew up a little bit.
Lewis Howes
Yeah, a little bit.
Sponsor Announcer
But.
Lewis Howes
But there was stress around money.
Jen Sincero
Right.
Lewis Howes
Which caused it to feel more unsettling. So there was some conversation, but most of the conversation was stressful or their relationship wasn't peaceful.
Jen Sincero
Right.
Lewis Howes
So I was like, okay, well, if they're not peaceful, but they're working really hard and money is tied to working hard, then something must be off.
Jen Sincero
Exactly.
Lewis Howes
And it wasn't a money issue. It was just an emotional healing issue.
Jen Sincero
Right.
Lewis Howes
And that just happened to be mixed in with money.
Jen Sincero
Yes. And so in your little brain, you put it attached to money makes stress. Yeah, exactly.
Lewis Howes
What was your perception of money before you started to make it versus when you started to make it?
Jen Sincero
Well, I grew up in a super WASPy household, so, you know, we don't discuss money. Like, it's, you know, dirty and uncouth.
Never learned anything about it at all.
Lewis Howes
And no education around it? Hell no.
Jen Sincero
Oh, my God, no. Like, nothing. And so when I. So I was very of the mind that it wasn't cool to want to make money, you know, the unholy dollar. Like, I was a rock and roller, so I was like, more about the art.
Lewis Howes
And you're not going to sell yourself out.
Jen Sincero
Exactly. Selling out, like, what a concept. Selling out basically means you're getting paid for doing what you like. Why is that so bad? Right. And then the whole starving artist crap and all that stuff. Yeah. And that rich people sucked and I was too cool to focus on money. I also believed I sucked at making it, which was the truth. I also had a weird feeling that, like, I was. It was almost Like a different species. It's almost like me. There's me and then there's grownups. Right. And I felt that way about money too. Like, there's me and there's people who actually make like real money and have big houses and fancy cars and like, do stuff like. But I was, I was like the child version of that, you know, always sitting at the kid table financially. And so it was a total identity shift that I had to go through where it was like that I could open myself up to, like, being somebody who could receive that kind of wealth. It was a real big shift for me.
Lewis Howes
Do you think we have to go through an identity shift in order to see money differently and to be able to receive it differently?
Jen Sincero
I think you do, absolutely. That's a really great way to go at it.
Lewis Howes
So what was your, you know, the key words around your identity with money, when you didn't have much versus the key words that you would speak about within yourself or what money is once you started to unlock more money?
Jen Sincero
Well, it wasn't necessarily around identity, my words, because I did have two very serious mantras, but there was a lot of visualizing myself with money. Like, I wrote about buying the Audi and you are a bad. And like, I'm not the kind of person who drives an Audi. Are you kidding me? Like, and like almost feeling like this. The guy who is like, test drove it with me would be like, get out of here. I know who you are.
Lewis Howes
You can't afford this.
Jen Sincero
Exactly. So, so, but my mantra is really like, and before I started making money, I said, I can't afford it to pretty much anything you could throw at me. My first words out of my mouth were, I can't afford it. And I.
Lewis Howes
What are we doing when we're, we're saying that whether it's true or not.
Jen Sincero
True, we are buying into an identity is somebody who can't afford stuff. We are also proving it. You know, what you speak, you want to prove because you want to be right. And it is sort of the foundation of your reality. So when I say I can't afford it a hundred times a day, I'm subconsciously pulling in proof. Like, look at the car I'm driving. I'm living in an alley. Like, I make this much money a year. I'm, I'm building all the foundational blocks to prove that I can't afford it. And that becomes my reality, and then that becomes my, I like to call it familiarity zone, because comfort zones are not comfortable.
Lewis Howes
Interesting, right?
Jen Sincero
So, so then I'M just proving it over and over and over, and that becomes my reality. And then to shift out of that literally means to obliterate your reality and your identity. Right.
Sponsor Announcer
So that's why it's like an explosion.
Jen Sincero
It is.
Lewis Howes
It's like you have to have a. Like a death, an explosion, a bomb almost to go off.
Jen Sincero
It does. And it's killing off your old identity. And this is why I'm going to totally go off on a segue here. But this is like the number one question I get at my talks is what do you do when the people closest to you don't support your growth? And the main reason they don't support it because you're killing off the person they love.
Lewis Howes
Oh, man.
Jen Sincero
I mean, think about that. Like you're changing who you are and they're comfortable with who you are, and they feel that's their reality, too, is. Is caught up in who you are being. So when you decide to change, you're killing off their buddy or their whatever, and you're screwing up their reality because you fit into theirs.
Lewis Howes
Wow.
Jen Sincero
So it's really a thing.
Lewis Howes
It's so interesting. I was telling someone on my team this a few weeks ago that in the different seasons of my life from 18 until now, I have had all these amazing experiences, from school to sports teams, to moving to new cities, to finding new groups and communities. And a lot of them I've.
Outgrown in certain ways or just transitioned out of. Maybe not outgrown, but just. I've gone to do other things and continue to try to evolve. I'm not saying I'm better than, but I've continued to try to evolve and let go of the old me. And some of them don't like it. And I lose friends totally in the process of changing myself, reinventing myself, letting go of old behaviors and stepping into a different identity. And it's not easy to have communities that you love and people you are familiar with and hanging out with that support you. And you go to parties and do whatever activities, and then all of a sudden they stop returning your calls.
Jen Sincero
Yeah.
Lewis Howes
And they stop texting you back. And you feel sad, hurt, you know, disappointed that you're trying to go somewhere and they don't support that. It's a scary time.
Jen Sincero
Yeah, it is. It's very lonely. That's why it's lonely at the top.
Lewis Howes
What suggestions do you give to people then, who are shifting their identity, stepping into a new reality for themselves and their friends don't like it, Their family doesn't like it. Their communities don't like it, and they're telling them to, hey, come back and hang out with us. What do you say to them?
Jen Sincero
Well, first of all, really make the decision. Are you going to stay small and shrink just so that you can be around those people and make them comfortable, or is your comfort more important and your growth more important? And also, it doesn't serve them either. Like, if you all stay at the same low level because not everybody ditches you, there are some people that are just like, oh, my God, you inspire the crap out of me. I'm going to do it too. Right. So focus. It's all where you place your focus. Right. And then also focus on who you're going to meet now that you're getting big.
Lewis Howes
Right, Right.
Jen Sincero
Those exciting, inspiring people who are turned on by the same things you are, who are doing the same things you are. Like, it's all about where you put your focus.
Lewis Howes
And you can only. I mean, I really only have maybe five to seven close friends that I can actually spend meaningful time with outside of my girlfriend, which I spend a lot of time with outside of my team, which I'm spending time with during the day.
Jen Sincero
Yeah.
Lewis Howes
There's only so many nights and weekends that I can spend quality time with people. And you may need to open up space to invite in people that are at a. I don't know, an awareness or a support or a level of thinking that you want to be at as well.
Jen Sincero
Right.
Lewis Howes
To create that time and connection with. So it's scary, though.
Jen Sincero
If it's not scary, you're doing something wrong though, right?
Lewis Howes
That's true. So how old were you when things started to shift psychologically, mentally and emotionally? And did you create a bomb? Was it more of a slow breakthrough for you and shifting this identity and this old skin?
Jen Sincero
Yeah, Yeah, I was 40. It was in my 40s. Yeah. You know, I really struggled and suffered for way too long. I mean, don't get me wrong, I had a fun life. Like, I was going on road trips and I was in a band and I was doing all the things I want to do, but financially I was just.
So stuck and stubborn in my thinking, you know, and so that's actually how I finally picked up a self help book. Like, I was. I mean, self help was as ugly as making money was for me. I was always scared I'd die and they'd find them in my house because I was too cool. And that's when I was just like, I have got to do something. And that's when I started reading them when I was sort of end of my 30s, beginning of my 40s. But it was in my 40s that I hired my first life coach and went totally into debt for it. Like, put it on my credit card, called her and begged her for the money back. And luckily she was a great coach. She's like, that could be the most important money you ever spend. And then I was like, front row doing every single thing she said. And luckily she was an excellent coach and I tripled my income in like three months.
Lewis Howes
And wow.
Jen Sincero
And then once things. Once I saw myself do that, then I was like, okay, this works, this works. And then I was just a straight A student, just doing all the things.
Lewis Howes
Just kept showing up.
Jen Sincero
Oh, I kept doubling my rates and kept cold calling and doing all this stuff that I was just like. But. But it was so cool at the same time, like, it was so fun because one of the things about being stuck is that life force that's going through all of us, right? Like, it was about the money, but it wasn't about. It was about the money. Money is great. I don't want to. You know, I love having money. It's so. It's just freedom and options, right? Money is just freedom and options. And who does not want that all day long? But also it was about the life force that. That I knew I could be doing better. There was just so much Jen Sincero that wanted to like, go shine basically, right? And I was blocking it off. I could just feel it. So it was just this clogging and this like, frustration that once I hired the coach, like, I was. I was in the game and I was. I was playing and I was taking risks and I was doing stuff I'd never done before. And it was so exciting. It was so alive. You know, it's a life force. Money is currency and currency is energy, and that energy is a life force.
Lewis Howes
And wait, when you were feeling stuck financially and around money, was it more of a thinking or a feeling in your body and an emotional connection to it, or was it both?
Sponsor Announcer
Both.
Jen Sincero
Definitely both.
Lewis Howes
What was the thought and what was the feeling tied to it?
Jen Sincero
The thought was, I am never going to get out of this. I'm 40, I'm living in a garage in an alley. I've never been able to make money. It's just not something I personally can ever do. And then more subconsciously, you know, lots of things subconsciously, but, you know, it's not okay to do it. I discovered that I had a really. The Biggest block for me was, if I get really rich, I will. My father, who wasn't able to show love very comfortably, would always give me a 20.
Lewis Howes
Or that was his way of.
Jen Sincero
Yep. And I was like, if I get rich, I don't need dad anymore.
Lewis Howes
Oh, wow.
Jen Sincero
And it's like putting a knife in his heart.
Lewis Howes
Oh, my goodness.
Jen Sincero
That one blew everything open for me when I realized that. And.
So, yeah, so those were the things. But it was really hopelessness, Just like frustration and hopelessness. Like, how am I ever going to get out of this?
And then I guess the feeling was hopelessness. Despair, sadness, anger, frustration, Resentment. Yeah, resentment. Yep. Everything.
Lewis Howes
Now, did you resent people with money back then? Was it like, oh, you know, screw them, they're entitled or they have this or whatever.
Jen Sincero
Anybody who talked about it, I was really resentful of. I was like, shut up, don't talk anymore. Yeah, yeah, yeah, yeah.
Lewis Howes
And what happens if we don't speak about money in a healthy way?
Jen Sincero
We perpetuate it as being the big boogeyman. Yeah. And I think anything that's hush hush has. And I do. I relate it to sex all the time. Like, we're all supposed to be really good at sex, but you're never allowed to talk about it, and you certainly don't learn about it. So it's like this weird, weird, mysterious, dirty thing. It really is. I mean, it's dirty. Money is dirty, you know, I don't want your dirty money. Like, you know what I mean?
Lewis Howes
It's dirty until you don't make it dirty. Right, exactly. Change it.
Jen Sincero
Exactly. So just by, like, airing it out and talking about it and being joyful about it and talking about what you do with it, joyfully and sharing it and making it and being happy that you made it and not, you know, it's so not a big deal. And it's like, we all need it, you know, it's so funny. I always think, like, you know, if I told the average person, like, I'm going to give you 10,000 bucks, they'd be like, sweet. And then, you know. But talking about, like, how do you feel about rich people? How do you feel about people who make tons and tons of money? And the disparity, you know, the difference between that. Like, you want it, but there's still dirtiness around it. Which is why I put in two of my books to write that letter to money because it's a really interesting exercise.
Lewis Howes
You wrote like a love letter to money.
Jen Sincero
Yeah, you just write a letter to money as if it's a person almost. So it's like, I love you. I wish I had more of you, but I don't trust you. And I feel like a dirty for even saying that. And, you know, all. So all the. All the things, and then you can see what you got going on.
Lewis Howes
This is a topic that I've been fascinated about for decades because I didn't have money at one point. Also, I was living on my sister's couch for a year and a half. I couldn't pay for the rent. I didn't buy food. I was just, like, living off of her for a year and a half when I was recovering from a surgery, a wrist that I broke playing football, and I was afraid of it. My father also got into a pretty.
Bad car accident a year prior to me getting injured, where he was kind of that, like, lifeline for me where he'd give me a hundred bucks when I needed it and paid for things and just said, hey, you know, go live your dreams, and when you're done, we'll figure out what you're gonna do with the job.
Jen Sincero
Right.
Lewis Howes
He got in a car accident. He had extreme head trauma, was in a coma for three months.
Jen Sincero
My God.
Lewis Howes
Ended up surviving, but wasn't able to work anymore. So he was physically alive, emotionally and mentally kind of not here. So he. He passed a year ago, but it was 17 years of him struggling, right, to try to recover. So I had this, you know, father backup to support me financially, in a sense. I mean, just give me a 20 or 100 bucks here and there, and he was no longer able to do that.
Jen Sincero
Wow.
Lewis Howes
So I remember being fascinated by this conversation 20 years ago because I was like, I don't understand it. I don't know how to make it.
I don't know why anyone would give me money. You know, where is my value come from? Like how to ask someone for money when I don't even know what skills or values I have?
Jen Sincero
Right, right, right.
Lewis Howes
And early on, I started to learn from these mentors and coaches teaching me about money. And one of them was around the way we speak about money. Because if we are essentially saying, this is bad and evil, or I'm not good enough for this, then why would that thing come to us? If we think it's bad and evil, we're going to be rejecting it, or if we don't think we're deserving of it, why would we receive it? Why would we bring it into us?
Jen Sincero
Right?
Lewis Howes
And so I had to really shift this conversation. You know, 20 years ago, around Money and do what you talk about, which is just having more open conversations, not talking about it like it's this hush hush thing, but just being more open and conversational and not being so emotionally like heightened.
Jen Sincero
Yeah.
Lewis Howes
When you talk about it and learn from a peaceful place of talking about it. So I love that you have this write a letter to money.
Jen Sincero
Yeah.
Lewis Howes
And really I tell people like, if you want your money to appreciate, you must appreciate.
Jen Sincero
Exactly.
Lewis Howes
And treat it like you're the greatest lover of your life.
Sponsor Announcer
Right?
Jen Sincero
Yes.
Lewis Howes
Treat like if you want your partner to be investing in you and to be giving you words of affirmation and physical touch and like gifts. If you want all these love languages, then you've got to pour into and appreciate the partner you're with.
Jen Sincero
Absolutely.
Lewis Howes
Tell them how grateful you are every day. Tell them what you love about them, what you see in them. And when you appreciate a person like you said, or if you appreciate money, it can appreciate in value and come to you in return.
Jen Sincero
Absolutely. It's energy and it really that like money is currency and currency is energy. Like, like I had to hear it like 6,000 times before I really got that. Money is energy. It's a frequency. So when you raise your frequency and get into alignment with it, and that whole alignment thing is all about none of the limiting beliefs, just just being in surrender and in alignment and having it flow in. So.
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Jen Sincero
Me what my mom, you know, what my words were. So at first it was I can't afford it. And then I eventually went to money flows to me easily and freely. And this is still while I was living in the garage, still while I was, you know, so in debt. But I had started doing all the energy work around it and I was like, all right, what are my blocks? Like when, when you write a new mantra, it's all about like really like the letter to money. Like what just kept coming up and that, that I was stuck and that it was hard and that I didn't know what I was doing. So there was like hard and stuck and confusion. So flowing easily and freely was just like, yeah. Even though I did not believe it at first, like it wasn't about believing it. It was about the feeling because we are emotional creatures and you know, that emotion, the frequency of emotions was, you know, the flowing, the easily and freely flowing was really, really powerful for me.
Lewis Howes
So now when you write a statement or a mantra that you're wanting to Step into, but you don't believe it yet. Is that lying to yourself? Or how do we overcome this thing that, okay, this is what I want and this is what I'm stepping into and the feelings I want to experience, but I don't have it yet. I don't, I don't. And that's not actually true yet.
Jen Sincero
Okay, I'm just gonna say if you are not successful at what you want to be successful for and you're feeling stuck, you're already lying to yourself because you're buying into the identity that is not in the flow. So that's the lie. So money flowing to me easily and freely because I live in an abundant universe and I am a creature who receives. That is the truth. So even though the identity that I'm in is not believing it yet, it doesn't matter. What matters is that I'm feeling it for. So I always tell people, like, you don't have to believe it at first, like, but you have to feel it. So that's why what the words make you feel like are the most important part about it. So ease and free and flow was the most important part of that.
Lewis Howes
Do you feel like, okay, you said you're around 40 years young when this kind of happened. Was there something in your life that was like, I'm just sick and tired of feeling this way after two decades. Or like, I just want to see what's possible for me in this next decade. Was there something around that time that made you say, all right, this hasn't worked for 40 years of my life. Yeah, now I'm going to try something different.
Jen Sincero
You know, I think it was. There really wasn't like I didn't almost get hit by a bus or, you know, I just, I. First of all, it's so boring being broke. Like, you can't do anything right, really, you can't do anything. So. And, and I think it was just sort of a. It's almost like I ripened, you know, it's almost like how many times do you hear something before the aha moment? You know, why does that suddenly happen? I think you just finally are in a place where you can hear it for some reason. So I had started reading the self help books and I was really into it and you know, I made a bunch of half attempts at like getting my act together, but I think it was just, I think I just ripened. And then I, I made the decision, like, I think really living in. And it was like a one car garage. Like it was small.
And I Think after a little while of that, I.
Lewis Howes
Was like, I'm sick and tired of this.
Jen Sincero
I am 40 years old. You know, I could do better than this.
Lewis Howes
Right, right.
Jen Sincero
And so I think I was just so sick of myself.
Lewis Howes
My friend Dean Graziosi says we pay attention to what we pay for. Do you think you making this investment in a coach made you pay attention? More to. Okay, now I gotta make my money back and I'm gonna make more than my money back. So I'm going to focus, I'm going to do all the painful things that she tells me to do and I'm going to be the best student I can be. Is that what your thought was because you invested?
Jen Sincero
Definitely. And I will say though is I've had clients pay me lots of money and not do a damn thing. So it's not a guarantee. So that is part of it for sure. Because I've also given like free coaching sessions to my friends and it's like the biggest waste of all of our time. Right. But. So I do think that the exchange of money is very, very real. But I think more importantly your attitude and the decision.
Lewis Howes
It's deciding.
Jen Sincero
Oh yeah, yeah, yeah.
Lewis Howes
Because you can decide to invest but you're still not committed to taking the action and doing whatever it takes.
Jen Sincero
Absolutely. And I've got been given things for free, especially at that time in my life, like anything I could get my hands on. I was straight A student, so the money did have something to do with it. But I was.
Lewis Howes
But you were also committed. Free pay, whatever.
Jen Sincero
I was ready. No, I was.
Lewis Howes
You were all in.
Jen Sincero
Oh my God.
Lewis Howes
Before you weren't committed.
Jen Sincero
Yes.
Lewis Howes
Because you had the emotional blocks that were just half.
Jen Sincero
Yeah. And so I do think it was that sort of. It's sort of like the water hitting the rock and then it's the Grand Canyon. You know, like reading the self help books like I did, I had started that a couple years before the garage. So I was sort of priming myself and then finally I was just like.
Lewis Howes
I'll do anything, let's do this.
Jen Sincero
Hit me. Yeah.
Lewis Howes
What was the book that really inspired you the most?
Jen Sincero
The Science of Getting Rich by Wallace Wattles.
Sponsor Announcer
Yeah, that's great.
Lewis Howes
A get one.
Jen Sincero
I mean not only because it's like this big, because I'm super impatient, but I mean it's super cryptic. It's like it's all about the universe being a thinking stuff and when you impress your thoughts into the thinking stuff, it becomes real and material world. And I just, I just, it really, really really spoke to me. I've read it hundreds of times. Really? Yes. Yeah.
Lewis Howes
What was the biggest takeaway from that book?
Jen Sincero
So happy you asked, because I talk about this line all the time, is to think what you want to think is to think the truth, regardless of appearances. So this is everything, right? So mindset is everything. So regardless of appearances, regardless of the fact that I'm living in a garage, in an alley, driving a car with no grill, like those are the appearances. But to think what you want, and I think the want is so key too, because that's your, that's your authenticity. That's not like thinking what other people think you should do and how you should live your life. To think what you want, the purpose that you were put on planet earth to live out. That's the truth. That is the truth. So your desires are the truth, not what's physically around you.
Lewis Howes
Wow. So how do we know that we are in harmony and congruency with our desires? That it's for something not just selfish and self serving by itself or ego driven, but more, I don't know, driven by something greater, you know, because if someone says, well, I want to make a lot of money, or I want to make a hundred thousand dollars in a year, or 500,000, or whatever it is, or millions, how do we line up our desires with our authentic selves so that we don't hurt ourselves in the process of making money or it become overwhelming, daunting or draining?
Jen Sincero
I think you always come back to, is it fun? Does it give me energy or deplete my energy and does it have meaning? Those are the three things that I'm really living my life by these days. And.
I think that if you're in alignment with those three things and other things, certainly, but those are sort of my big three.
Lewis Howes
Is it fun? Does it give me energy and does it give me meaning?
Jen Sincero
Yeah. And is it meaningful? Yeah.
Lewis Howes
Is it meaningful? Yeah, I like that.
Jen Sincero
Yeah.
Lewis Howes
And where were you at 39 doing things that weren't fun, that drained your energy and gave you meaning?
Jen Sincero
Yeah, pretty much. I mean, I was a freelance writer hustling my butt off. And then like when I really did the math, I was like the amount of time I spent hustling for this gig and they don't pay that well, like magazine articles. Come on. I was making like, I was probably losing money, quite frankly.
So. Yeah, no, there was, there was none of that. It was not fun. It was exhausting. It had some meaning, but you gotta get all three, you know? Yeah.
Lewis Howes
Or at Least start working towards it. Because you may not be able to at this season, but you gotta focus on can I get one?
Jen Sincero
Can I get one? And is it leading in the direction of something that is fun, that is gonna give me energy and has meaning? Because you're right. Like when you're building a company or when you're doing something like, it is exhausting, but if it's still exciting and fun and has meaning, then yeah, yeah, it doesn't get to be a picnic all the time.
Lewis Howes
When was the biggest aha moment for you then? Like, was it after you made a certain amount of money or a client paid you something, or was it just a feeling you had, like releasing all of it in the process of working? Like, when was that moment where you're like, I'm actually emotionally and mentally free around the idea of money.
Jen Sincero
Oh, interesting.
Lewis Howes
Maybe I'm not funding.
Jen Sincero
I will tell you. No, I actually did and I did put it in. You are a badass. I put it in one of them. It was when I had. Oh my God, it was such a cool moment. So, because money is currency and currency is energy, right? So we're really going to get woo woo with the money, like really shifting the mindset around money. And I. And bring me back to my story. If I go off on a tangent, because I'm about to go off on a tangent, I want to remember, but I.
Lewis Howes
Money is currency and currency is energy.
Jen Sincero
Yes, money is currency. Currency is energy. And I've had so many clients that have told me, and it's happened to me too, where they manifest when they get into the meditation and they start to raise their frequency and they focus on the amount, the exact amount comes in from outer space that you didn't even think of. And so my story is around that, where I was working with my coach and we were really going to shift my money reality. And so she's like, you know what amount of money would be really great for you to make right now? Like, what would have a lot of meaning? And I was like, $10,000, because I'm $10,000 in debt on my credit card and I hate being in debt. She's like, perfect. And so she's like, okay, so how soon are you going to make it? And she goes, you know, like about a week, two weeks. Because I, you know, and I was at the time making like 30 grand a year. I was like, my God, If I made 10,000 in a week, that would be incredible. And I was like, but you know what I got to do it in two days because I know myself, and I won't keep myself in that frequency. Like, I'll lose steam and I'll decide that. Like, nah, it's not. I can't do it or whatever. Like, I knew that the stuff would start creeping back in, so I was like, all right, 10 grand in two days. She's like, great, okay, so how are you going to do it? At the time, I had this little online coaching business that I had just started coaching writers. And I said, I'll get three private clients, blah, blah, blah, blah. So then we're, you know, putting all the pieces in place. And then she's like, okay, and is there anything else? And I was like, well, you know, there was this guy that I was coaching years ago. He was my first private client. I was charging him like 50 bucks an hour. And I was like, I could also call him and see if he wants to work with me again. And she's like, okay, great. And we're still on the phone. And I check my email and he has written me. I have not thought of this man or communicated with him in years. Email. He's like, you know, are you still coaching? Can you help me? When can we start?
Lewis Howes
Wow.
Jen Sincero
And so she's like, okay, here's what we're gonna do. We're gonna put together a $10,000 package for him, and you're gonna sell it to him right now.
Lewis Howes
Holy cow.
Jen Sincero
I know. And I was like.
I was charging him 50 bucks an hour. I was. And I really adore him. He's such a special person. And I was like. Felt like, you know, a greedy pig, blah, blah, blah. All the things. Fraud, complex, gigantic imposter syndrome. Oh, beyond. Beyond. And so we put. She's like. And what we'll do is we'll put together a $15,000 package and a 10. So the 10 looks cheap. And I was like, I can't do 15. She's like, all right, 12. Pain in my ass. I did a 12, sent it to him, and literally wanted to throw up. I was just like, if he. Because I really cared about this guy, he bought the 12.
Lewis Howes
Holy cow.
Jen Sincero
I know.
Lewis Howes
I should have made it 15.
Jen Sincero
I know. Exactly.
Lewis Howes
I know. Well, here's the thing, you know, it's not like you were charging him 12 hours on an hour. Obviously, you created a position packaging of services that would over deliver that would serve him a big way.
Jen Sincero
I worked with him for five years after that.
Lewis Howes
Exactly.
Jen Sincero
Yeah, yeah, yeah, yeah.
Lewis Howes
So it's not like I'm just going to Charge some number and give very little.
Jen Sincero
Oh, no.
Lewis Howes
You made sure that the value was there.
Jen Sincero
Totally.
Lewis Howes
How did you learn to package and position your value to be able to charge for what you wanted?
Jen Sincero
My coach helped me put it all together, but then I had to rise to that frequency. And I'll tell you, you know, when you're charging something that scares the out of you, you show up with your A plus game. Like. And he did too. Like, it was a lot for him too. We knocked it out of the park.
Lewis Howes
Because you pay attention to what you pay for.
Jen Sincero
Yes.
Lewis Howes
Right?
Jen Sincero
Yes. Yeah, totally.
Lewis Howes
You'll rise to the occasion. Like, I gotta focus.
Jen Sincero
Yes.
Lewis Howes
I gotta give. I got to show up on time, deliver the results on time.
Jen Sincero
Absolutely.
Lewis Howes
Give my best here.
Jen Sincero
Yeah.
Lewis Howes
Interesting. So now here's. I'm curious about the next thing. Was that everything to the story? First off, I want to make sure I get. Yeah, okay. Money is currency and currency is energy. I'm curious about the next thing. So once this happened and you sold a $12,000 package and you were like, this is crazy and this is more money than I've ever made in my life. Essentially, in two days. Did you fall back at any point or did you stay focused?
Jen Sincero
Oh, interesting.
Lewis Howes
Because sometimes people get an opportunity and they get excited and then. Well, I tried it again. It didn't work. So maybe this is a fluke. Maybe this was a one time. And the thermometer goes back down to what they're comfortable or familiar with.
Jen Sincero
Very common. Very common. I did not. But only because I continued to get coaching and I got bigger and bigger and bigger packages. I mean, I was paying six figures by the end, 100 grand for like.
Lewis Howes
A year of coaching or. Wow.
Jen Sincero
So I just. Because I knew myself, I was like, I am rickety in this whole sort of wealth consciousness department. So I knew that I had. It's like getting a personal trainer. Right. So I just kept investing in the coaching and now. Now I'm good. But I do still have to work at it.
Lewis Howes
I mean, it's different levels.
Jen Sincero
It's different levels, you know, and you.
Lewis Howes
Feel comfortable at this level, but if you want to break through.
Jen Sincero
Exactly.
Lewis Howes
Do something you've never done. You've got to have a different frequency still.
Jen Sincero
Right, Exactly. You get, you know. Yep. Oh, there's always more growth to be had.
Lewis Howes
Do you feel like you're kind of at like a block right now? Because again, you've sold, you know, I don't know, 5 or 10 million copies of your books, you've got coaching program, you've got all these core success, financial freedom, all these different things. But is there like a level you've reached that you feel like, okay, well, can I break through that? This is so much now and I feel abundant, but could you break through?
Jen Sincero
If I want. If I could decide what I want the next thing to be yet I'm still in that sort of incubation period of like, what would be fun, give me energy and have meaning. I'm getting there. Like, I definitely feel like I'm getting there and I'm doing a lot of things that meet those requirements in the meantime. But it's not the big.
Lewis Howes
What's your biggest. What's your biggest fear or insecurity around money right now?
Jen Sincero
That I don't know what to do with it when I make it. Like, I'm good at making it. My bookkeeper called me one day and she's like, would you please just open a savings account at your bank? Because I had like a million dollars in my checking account. This was a while ago. I finally got my. So I've hired financial plan. Like, I've hired people who. Grown ups who know what they're doing with money, but like, I'm teaching myself about it, but I find it boring. I find investing boring and confusing and out of my league. So luckily there are amazing people who know what they're doing. So I have finally gotten that team together.
Lewis Howes
Gotcha.
Jen Sincero
And there is a little tiny part of me, if I gave it any attention, that is a little scared it's all gonna go away.
Lewis Howes
Really?
Jen Sincero
Yeah. But I don't. I'm not. It's not that bad. And I probably should not even speak it out loud.
Lewis Howes
Yeah, well, you're being, you're being honest about it. I think there's one thing about speaking it out loud so it doesn't happen, but another thing about saying it so it doesn't have power over you.
Jen Sincero
Right. Yeah.
Lewis Howes
You know, it's like, we'll take that. Like, you're afraid to have the conversation around money. Yeah, I'm all believer. Like, don't speak into something in existence you don't want to happen. But I think, you know, when I started talking about my fears, my shame and my insecurity, it actually felt like the poison was coming out of me. And now I could see it outside of me or I could have a conversation with it as opposed to it being in me and afraid to talk about.
Jen Sincero
Right.
Lewis Howes
And then I could get coaching about it.
Jen Sincero
Right.
Lewis Howes
And then I could, okay, let me create a game plan. Okay, well, I'm afraid of it, but now I have a coach to help me, you know, invest it the right way and whatever I need to do.
Jen Sincero
Yeah.
Lewis Howes
You know, so.
Jen Sincero
Yeah.
Lewis Howes
As opposed to ignoring it and just. I hope I don't lose it, but I don't want to speak about it.
Jen Sincero
Right. That's a good point. That is a good point. Okay, I'll tell you another one.
Lewis Howes
What's the other one?
Jen Sincero
The. The other one is that I'm gonna make too much of it, and I won't. And it is. It's kind of like the same as the first one, but I won't know what to do with it. Like, I'm scared of it coming in too fast and too much because it's gonna bury me alive almost. Yeah, I know. I know. And so this is why. So I bury me alive kind of. Yes.
Lewis Howes
Why would it bury. Why would money bury you alive?
Jen Sincero
Just telling you what I.
Lewis Howes
Well, this is the interesting thing, Jen. I think it's powerful that you're talking about this, because there's different levels of insecurities or fears at the stages of money we make. And when I was broke on my sister's couch, I had a lot of fear and insecurity, uncertainty of the future. And then I remember, in one day, I made $6200 in an hour doing, like, a live webinar selling a program. This is in 2009.
Jen Sincero
Okay.
Lewis Howes
Well, there was, like, courses and webinars, all this stuff.
Jen Sincero
Yeah.
Lewis Howes
And I go, I'm the richest man in the world with $6200. Now, I had to split that with the person who promoted this training for me, but I still felt like $3,100 in an hour. I go, I could do this every day for the rest of my life. Right. Because I was sleeping on my sister's couch.
Jen Sincero
Yeah.
Lewis Howes
But there was still. I never made six figures, and so there was still a challenge, like, how do I do this and how do I manage it? And I understand it. And now taxes, what all my money's gone from. I just made money. I have zero again. And this fear of, like, this tax thing. And then you get to the next level. The next level. Next level. And I just think there's different challenges or things we get to overcome at every level of money as well. Sure.
Jen Sincero
Yes.
Lewis Howes
You know what I mean?
Jen Sincero
Level. New devil. Right? Yeah.
Lewis Howes
So one of the fears is, will the money bury me alive?
Jen Sincero
Yeah.
Lewis Howes
Why do you think that is?
Jen Sincero
Like, oh, gosh, why do I think that is? I think it's my insecurity about not knowing what to do with it when I had, when I had very little of it, I could manage it. Right. That was easy. And then as I started getting more and more and so I do have pieces in place, but I've opened, I've hired a new financial team so I can make like build the nest. And it will come because I was like, if I don't take care of this, I will literally block it. I will energetically block it if I'm scared of it coming in and think it's going to bury me alive. Like, that is not a abundant mindset, you know?
Lewis Howes
Sure.
Jen Sincero
So, yeah, So I, I just created the nest. So now bring it on, universe.
Lewis Howes
Right, Right. So now you can, you have, you have a foundation for it to come in.
Jen Sincero
Yeah. Yeah. So it's not scary anymore because I know where it's going to go.
Lewis Howes
Yeah.
Jen Sincero
But I realized that I was just like, wow, I am kind of scared of it coming in too much. I know. It's interesting, isn't it?
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Lewis Howes
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Lewis Howes
I think we all get to experience at different levels how to break through. Otherwise it wouldn't be interesting if it was just, I don't know, there's no obstacle.
What do you think are the key things that abundant mindset people around money do differently than scarcity Mindset people around money, if you had to say three or five kind of key things, they.
Jen Sincero
Appreciate it. As you said that that is a biggie. They appreciate it and they speak about it as they love it. They're not weird about it. They're also generous with it because when you pinch yourself off from giving, you that is sort of a subconscious way of saying there's not enough to go around and it's not going to, I'm not in the flow. So when you don't give generously, it's because you're scared that it's not going to come in anymore. They take risks. You know, you got to take risks. You are where you are because you've been doing what you've been doing. So if you want to change your life, you've got to do stuff you've never done.
What else? Wealthy people, they learn about money. Like you, you focus on money. Like, that was such a big thing for me too. Like when I was broke, I, I never wanted to think about money, right? I was all about writing songs and, you know, doing much, you know, more noble things.
Lewis Howes
Sure, sure.
Jen Sincero
But then, but when you're broke, all you think about is money. Like, I don't really think about money that much now that I have it. Like, but every single decision you make when you're broke is about.
Lewis Howes
So I would have to pay for this Exactly. What happens if I don't have money?
Jen Sincero
Right. You wake up in the first thing in the morning in a panic because you got to pay your bills. So you're always thinking about money. So it is really just sort of getting in the flow with that and just, you know, being on good terms with it and focusing on it and. And, you know, how are you going to make it? Like, being realistic about your income streams and, you know, and if you want to make it, you've got to coax it in, you know, give it. Yeah.
Lewis Howes
I'm curious about this. Okay.
Jen Sincero
You.
Lewis Howes
You're a starving artist. You wanted to do noble things, which. About art and making art and all these different things.
What would have happened if someone would have said, jen, you know what? I love that you're an artist. I love that you have this, you know, passion for art, and you want to keep doing this, and this is the way you've been for 40 years, and we don't want you to change. Here's 100 grand a year for the rest of your life. Don't worry about money. Up to 100 grand. What would that have done to you if someone would have given you 100 grand a year and you would have just been like, okay, I'm gonna write and do whatever I want? And how do you think it would have been? Mentally, emotionally, spiritually, versus you having to risk emotionally and mentally you getting to heal, let go, overcome.
Jen Sincero
Right.
Lewis Howes
Challenge yourself into asking for money, into becoming something greater than that. Limiting belief. What do you think? Where do you think it'd be now?
Jen Sincero
Probably would have spent it on beer. Honestly, back in those days. Yeah.
Sponsor Announcer
Yeah.
Jen Sincero
I mean, I wasn't. You're absolutely right. It's a frequency, you know, it's like. It's like.
I don't know. I mean, I always. I always had.
I guess I'm gonna say gall. That's not the right word. But I did. I did do a lot of stuff that was pretty edgy, and I pushed the envelope a lot. So I may have gotten there, but I don't think it would have been as exciting as it was to do it myself. There really is. You do grow. And they say, you know, starting your own business is the best personal development course you can possibly take, because all your stuff comes up. Right.
Lewis Howes
All of it. So relationship training, it's leadership training, it's inner child training, Everything.
Jen Sincero
Everything.
Lewis Howes
Everybody is pushed.
Jen Sincero
Totally. So. So it wouldn't have been as satisfying, I don't think. I think I still would have done it, though, because that is kind of my personality. When I'm ready to change, I'm ready to change and I do it, so. But I think it wouldn't have been as glorious and I'm definitely. I probably wouldn't have written you are at that. Which totally changed my entire life.
Lewis Howes
So it changed yours, but also changed other people's lives.
Jen Sincero
Yes.
Lewis Howes
So it's who you become, the lessons you learn, the wisdom you have.
Jen Sincero
Yes.
Lewis Howes
To then be able to be of service and teach.
Jen Sincero
Yeah.
Lewis Howes
From your own experience.
Jen Sincero
Exactly. Yeah. The book about me getting 100 grand a year just for being would not be that interesting to people.
Lewis Howes
Right? Yeah. Right. That's interesting.
Jen Sincero
Yeah.
Lewis Howes
What is the question you get asked by your readers the most that you wish they truly could hear and believe the answer to?
Jen Sincero
Oh, so many. Well, the one that I said about, what do you do when the people closest to you don't support you? Another one is how do you keep the motivation? Like, you know, we go to these seminars, we read books, we listen to the podcasts, and we're all raring to go.
Lewis Howes
And then a month later you go back in your old podcast.
Jen Sincero
Exactly. Yeah.
Lewis Howes
So how do you stay motivated on your vision and on your growth journey?
Jen Sincero
Well, I call it going to the spiritual gym. And you've got to have a spiritual gym practice because you do not get to work out physically and then stop going to the gym once you're in shape. So just because you got in shape at the seminar or listen to the podcast or whatever, you don't get to stop doing stuff. So. And it doesn't. And you know, everybody, I'm gonna working so hard to start my business. I don't want another thing to do. So it's like it can be 20 minutes. You know, you working out for 20 minutes a day can do a lot of great things. So it's like spiritual gym workout, meditate for 15, read a self help book for five. Like, what music are you listening to? Who are you hanging out with? What makes you feel like you could flip over a car? Like, what are those things? And do them every single solitary day for 20 minutes. It's not that big a whoop dee doo, you know, when you think about that, it's going to change your entire life, you know, so. And take it as seriously as anything else, because that work will make everything else that you're taking seriously and trying to achieve so much easier. And, you know, I'm giving a lot of talks right now, and the thing that I'm just so excited and I'm so excited to be speaking right now too, because it reminds me it's my spiritual gym, right? Like, we all need it. So. But the thing about. Because we are spiritual creatures, having a physical experience, right? And if you. And like, instead of just giving it lip service and talking. Yeah, yeah, I know that. But think about it. We are the universal intelligence that created everything that is we are our thoughts, our universal intelligence, the stuff that created everything that is. Why are we not more stuck up? Why are we not feeling so powerful all of the time if we're really going to believe it, if we're really going to go steroids on Woo Woo and go there and really, like, if you thought about that all day long, about your thoughts being, you know, when you're in alignment, not the garbage thoughts that you think, but when you get quiet and you tap into your inner yippee skippy, as I like to call it, and you're there and you're in the flow. It's like, it's so exciting, right? Instead of spinning out on how pissed off you are at somebody, you're freaking out about this.
Lewis Howes
Judging people or judging people, what we.
Jen Sincero
Do all the time, right? If you can just catch yourself. And that's why awareness is the key to transformation, right? So you just catch yourself when you're in the spins. And. And this is why meditation is so important, because it gets you into the habit of catching yourself, right? Because you're trying to stay clear. So. So it's not just about catching yourself in meditation and moving the thoughts away. Meditation is practice. We're doing it all day long. So catching yourself and be like, ah, I'm going to tap back into universal intelligence, the stuff that created all that is so. And then just going from there.
Lewis Howes
If you could reflect on. You are a bad. Which when I read it, it gave me like this jolt of energy because I was like, this is exactly what I want to talk about consistently. You know, I had, I had the school of greatness I think had come out for maybe, I don't know. I think I read your book maybe a year after I started. I saw it on the shelves, but I ended up getting it maybe a year after I started the show. And I was like, this is amazing. I'm so glad you're talking about this because it's everything that I believed in and everything I wanted to continue to express in my own way. If you could reflect on one idea from that book and you can only share one idea.
Jen Sincero
You're so mean, man. All right, let me take A book.
Lewis Howes
That you believe is the thesis of the book that you want people to remember and remember a concept, a phrase, an idea from it. What would that be for you?
Jen Sincero
Well, kind of what I just said. But since I just said it, I'm going to use my point for another one. Use my one thing. My one thing I get to say. I really believe that if we all did something that scared us every single solitary day, our lives would change so quickly. We wouldn't know what hit us. Right.
Lewis Howes
Let's go, Jen.
Jen Sincero
And scary in that, like, terror excitement way. Like terror excitement. Like you don't have to, like, run into traffic, you know, but something that's, like, in the direction of where you want to go that scares you. Because fear is the sign. It's the compass that you're getting outside of the familiarity zone.
Lewis Howes
So true.
Jen Sincero
Right? So if you just take those steps outside and just do the scary thing every day. Every day.
Sponsor Announcer
Wow.
Jen Sincero
Because that's. That's really. When I was making all of my huge financial transformations, it was always, you know, my coach would always tell me something. I'd be like, totally didn't want to do it, but I knew if I did it, it would transform my life. And it was exciting, you know, it was like leaping into the void. Just like.
Lewis Howes
Yeah.
Jen Sincero
And that's a sign. Yeah.
Lewis Howes
I have this concept in my latest book, the greatest mindset called creating your fear list. If you want to become fearless, you've got to create a fear list that's brilliant and really go all in on this. This is something I did as a teenager in my twenties and my thirties, at different seasons of life. I was like, what is the thing that makes me feel so insecure right now? I had a lot of false confidence, and I was like this jockey ego. Like, I'm big and tough and I'm an athlete and I can dominate on the sports field. But then I couldn't talk to girls without being sweating and being terrified. I couldn't dance or sing in public without being humiliated or whatever it was. I couldn't speak in public also. So all these things I wrote on my fear list in my 20s, after I broke my wrist and was on my sister's couch, I was like, I'm already humiliated. I have no money. I'm living in my sister's place for a year and a half. My dad just went through this thing that I don't have him really in my life anymore.
My passion, my dreams are gone. So I have. What do I do now? Let me just conquer all My fears. And it was the greatest gift I gave myself because it gave me so much belief and confidence in me. Every time I would just get a little bit better in my fears. It's not like I had to overcome it all in a day, but I just saw a little bit of progress every day and practicing my fears, public speaking a little bit every week. I was like a little less nervous, a little more confident, a little more skill every week over a year's time where I was like, man, I'm a powerful human being. I can do anything now let me figure out the next fear. And just kept repeating it and, and I'm still in that now. Like I'm, I'm trying to learn Spanish and I still get insecure like speaking Spanish. I'm still like a beginner, but it's like I gotta keep practicing and a little bit of growth every day a little bit better. You know, I don't have to be fluent overnight, but what am I overcoming just little by little? That really gives me a lot more confidence in self and belief. And I think my thesis is self doubt is the killer of dreams.
Jen Sincero
Right.
Lewis Howes
When we doubt self, it's really hard to do anything courageously because we're constantly in doubt mode.
Jen Sincero
Right.
Lewis Howes
So I loved your book about stop doubting yourself and start stepping into your greatness.
Jen Sincero
Yeah.
Lewis Howes
And a lot of people are stuck in doubt. What do you think beyond facing fears we can do to believe in ourselves more and overcome the self doubt that we have better?
Jen Sincero
I think not waiting until you're ready. You know, and this is kind of saying the same thing like facing the fear but like making sure everything's perfect. Making sure you've got all the money tucked away. Making sure you're the right weight, you know, whatever. Like, like just doing it now, you know, just do it now and take action now is, is a really big one, I think. And.
And also.
You know, paying attention again to how you speak about yourself and what you think about yourself and what you, how you treat yourself. And you know, I wrote a whole section in Bad Habits about boundaries. You know, boundaries are huge when it comes to self care and self doubt. And we make lousy boundaries and put everybody in front of us because we want to be liked and you know, and then we're passive aggressive and resentful which is super fun for everyone, you know, so it's like, but you know, really getting clear on who you are and what you love and making that a priority.
Lewis Howes
When did you stop abandoning yourself?
Jen Sincero
You know, I still do it Sometimes, of course. I mean, yeah, yeah.
Lewis Howes
In what ways do you.
Jen Sincero
Oh, God.
Lewis Howes
Is it in relationships? Is it in self care? Is it in the way you talk?
Jen Sincero
Not speaking? You know, sort of not standing my ground in the moment. If somebody says something really crappy, you know, and it doesn't have to be. I'm not. I also don't want to be the personality police. Like if someone's gonna say something, but more just not saying anything. Like, instead of like brushing it over because it's awkward, just letting it sit there like the big turd it is and let it. Everybody, like have a good look at it instead of helping them recover or, you know, just like in the. In the moment is always interesting to me. So slowing. So my mantra for the past five years has been like, slow down and shut up. Like, just slow down and shut up. Like I'm, you know, just listen and just choose your words wisely.
Lewis Howes
You don't have to react to everything.
Jen Sincero
Exactly. So, yeah, for sure.
Lewis Howes
Personality police.
Jen Sincero
Yeah. It's not your job to teach everybody how to behave. Let them say what they want. Let them, you know, and this is all part of my whole, like, not giving a crap what people think of me. It's just like, think what you like, think what you like. It's not my right.
Lewis Howes
It's almost. It's almost, you know, in a way. And I've done this many times. It's not like I'm saying I'm above or anything, but when we judge another person because they didn't do it the way we liked it, or they think they should do it or it's appropriate in the setting. We are being judgmental. Yeah, we are being judgmental. We're not accepting. I'm not saying that's the right or wrong thing to do, but it's just something to notice. Yeah, there's a judgment that's happening.
Jen Sincero
Oh, yeah.
Lewis Howes
And when there's a judgment, there's usually a right and wrong.
Jen Sincero
Yeah.
Lewis Howes
And so it's just. Is that serving us in the flow of our peace, our happiness, our abundance and being in harmony with the world. And maybe there is a time where we need to step up and create a boundary and say something and say, get away from me or whatever it is. But.
Jen Sincero
But it's really more about. It's the inside job thing where it's none of your business, you know, that's their journey. So that's really, you know, and I don't think we ever get there. I don't think. I think it is human to Judge and judge, you know, and it's fun. Come on, let's be honest.
Lewis Howes
Sure, sure.
Jen Sincero
But. But I do think that it's a very worthwhile way to spend your time, like, working that muscle and just getting. Because it's also more fun, like, if you don't. If you just leave it to them and let them do it. It's. It's. You're not spinning out on it anymore. You're not focusing on it, which pulls more of it into your radar anyway. Like, if you can just. Just focus on what feels fun and good and true and just, like, let them have it back.
Lewis Howes
Right? How important is healing our past and our thoughts tied to having peace around making money?
Jen Sincero
Super important. Because if you're. Because if you go out and make a ton and you're still weird about it, right. You're first of all not going to enjoy it and you'll probably lose it or you'll be, you know, put it in a hole in the backyard and never spend it or hoard it. Yeah, yeah, yeah, yeah. So it is.
Lewis Howes
What is the thing that people should focus on healing the most in order to set themselves financially free?
Jen Sincero
I think it's different for everybody. I think we all are fed different lies and fears and things. So I think it's. But.
Figuring out what your bag of worms is, you know, you got to get clear about that. And I'll tell you, the way that I discovered the big kahuna for me, which was my dad, like, stabbing my dad in the heart, like I was talking about earlier, was spending money. So the way that I. So I did. I did the Letter to Money. I was doing all. I was really serious about figuring out my stuff with money. And I was at a coaching seminar, and this coach was speaking from the stage, and he said that he charged $85,000 a year to work with him. And I. He was great, and I really loved him, and I totally wanted to work with him. And when I heard $85,000 because I had been doing all this work on my wealth consciousness, instead of being like, he's high. Like, what a. You know, but about a million.
Lewis Howes
He's crazy. Yeah, yeah.
Jen Sincero
Very rational excuses not to do it. Instead of going there, I went to, okay, how am I going to get 85 grand? Like, that's where my mind went first. And that's only because I'd been going to the Financial Spiritual Gym for so long that that's where my mindset was. So I went, how am I going to get $85,000? And I had a vision of my father, and a lot of stuff comes to me visually. A vision of my dad. And he always wore this yellow V neck sweater, and he had his hands in his pockets, and he was looking down at the ground, really sad. And I was like, oh, my God, that's it. It's going to kill him if I get rich because he won't be able to show me he loves me anymore.
Lewis Howes
Oh, my gosh.
Jen Sincero
It was so profound. And that really was a straw that broke the camel's back for me. It was.
Lewis Howes
So what did you do after that? Then?
Jen Sincero
What was interesting, I ended up not working with that coach, but I got you thinking about. Yeah, but I ended up hiring a different coach, a lot of money a couple weeks later for the same amount.
Lewis Howes
Oh, wow.
Jen Sincero
Yeah.
Lewis Howes
And so how did you heal that belief around, like, I'm gonna kill my dad if I make a lot of money. Did you have conversations with him? Did you do something internally? What?
Jen Sincero
It wasn't about him at all. It was about me and my perception. So what I started doing was visualizing him being so proud of me and supporting me and being happy and, like, turning it around. Just being like, he's. He's going to be so relieved that I can take care of myself, because my dad was. Had me when he was older. So it's like, he'll. He'll feel so rested. And. And the other thing, too, that was so funny. Like, my relationship with it was pretty. Was pretty rough. And so whenever. When I started getting. When I started making money and I would tell him about it, he didn't really listen very well. And I'd be like, dad, you know, I just got paid this much. He's like, that's nice. He has an Italian accent that I always try to imitate that I'm terrible at. But at the end of the call, he'd be like, you know, do you need some help financially? And I'd be like, dad, I just told you that. And so I'd get, you know, all after the yellow sweater, hands in pockets moment, I was like, it's the only way he knows how to show love. So I could be like, dad, I just made $10 million. And at the end of the call.
Lewis Howes
He need 20 bucks.
Jen Sincero
Do you need 20 bucks? I'd be like, you know, that'd be great. Thank you so much. And I can see how much it meant to him. And I get 20 bucks and everything's good. So it was a really beautiful. And it really healed my relationship with him a lot.
Lewis Howes
Wow. Did he say I love you? Did he speak?
Jen Sincero
Oh, he always said I love you. Like, he was, he was good that way, but he was a real. He just, he was a super introvert and he just was really uncomfortable with emotions. Yes. And he's Italian. I thought they're all screaming and yelling, you know, I was like, are you sure you're Italian?
Lewis Howes
Sure, sure. But that was his way of showing affection and that he loved you by, by this act.
Jen Sincero
And he also was raised to think men are providers and that's how you show. Yeah.
Lewis Howes
Even if you make money, I'm still going to provide and support you.
Sponsor Announcer
Yes.
Lewis Howes
What do you think would have happened if you would have stopped allowing him to give you, you know, 10, 20, 50 bucks?
Jen Sincero
What a really good.
Lewis Howes
If she wanted to give it to you, what would have.
Jen Sincero
It would have really hurt his feelings. Like, it really would have made him feel cut off from me.
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Lewis Howes
US.
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Lewis Howes
So this is interesting because you don't need someone to pay for you for things, right? Like you can pay for your own life. You can pay for food and dinner and trips in your home. Like you don't need someone to pay for things. The thing that I've learned in the last couple of years of being with my, with my girlfriend Martha is that It's. It's. You know, I don't.
She can take care of her own stuff, and she takes care of certain stuff, and there's certain things that I take care of for us, and I take care of myself financially in certain ways. But.
I've gotten to the point where I don't feel like I need to pay for everything, to feel like she. Like I'm enough.
Jen Sincero
Right.
Lewis Howes
Like I'm. I'm good enough or that I'm deserving or worthy, or this is my value. And being able to give everything financially now, again. And I don't want to rob her of being able to pay for the things that she's made her money. I want her to be able to pay for certain things for herself. But it does mean I get to show up.
In a different way. Maybe not financially, but spiritually, with my presence, with my generosity of my words and my. My time, my thoughtfulness, and provide value in other ways not tied to money. And sometimes that can be uncomfortable if we haven't trained ourselves how to provide value outside of money in relationships. And I've had to learn that. And it's been a powerful breakthrough in a lot of ways. It hasn't been in the last two years. It's been like a decade of me doing this, but it allows me not to feel like, oh, she's paying for her own food right now. I'm worthless.
Jen Sincero
Right.
Lewis Howes
You know?
Jen Sincero
Yeah.
Lewis Howes
Then I'm. I'm nothing to her, you know?
Jen Sincero
Right. Yeah. Yeah, yeah.
Lewis Howes
And it's been a. It's been a. It's been powerful to empower her to be able to make decisions financially.
Jen Sincero
Yeah.
Lewis Howes
Which she was doing before me. She doesn't need me to do that.
Jen Sincero
Right.
Lewis Howes
She was already doing that.
Jen Sincero
Yeah.
Lewis Howes
But to me, not feel like I have to pay for everything.
Jen Sincero
Yeah.
Lewis Howes
And she just has to, like, let me provide. Yeah.
Jen Sincero
I know. It's interesting.
Lewis Howes
It's a. It's more of a mutual providing of value in the relationship intimately, peacefully. Like, the highest currency for me is peace.
Jen Sincero
Yeah.
Lewis Howes
I would take peace over money all day long. And she brings peace to the relationship. Therefore, I don't need her to ever spend money on anything. Just be peaceful. And I'm. You've got a happy man.
But. And I think that's just something to look at. Like, what. How can you bring value into a relationship not related to money?
Jen Sincero
Yeah. Well, listen, Louis, I'm cutting you a check after I leave. Like, the fact that you said that right after. I was like, of course it's my Daddy stuff. I mean, come on. Yeah. Yes. No, that is something to look at for sure.
Lewis Howes
What was the best lesson your dad's taught you?
Jen Sincero
You know, he.
Oh, I don't know if this is such a great lesson, but it's a really funny line, so I have to say it. But I remember when. I think he taught me a lot about perspective because he grew up in Italy, in Naples, and he didn't come over here until he was in his 20s, and so I did. And he just always thought American children were so spoiled. He was like, oh, my God, you whiny little. Like, I can't even believe. So I remember, like, one time, like, in college, I was like, dad, will you help pay for therapy? I'd really like to talk to a therapist. He's like, you don't need therapy. You know what you need? A war fought on your soil.
Lewis Howes
Oh, my gosh.
Sponsor Announcer
Okay.
Jen Sincero
Right. Good perspective, but just sort of his. I mean, I think also that you can love in different ways. Like, I feel like that's sort of what he has really taught me. You know, with the money, stuff like, that was just his. You love however you can. And that he really did. I mean, the guy could not look at me without crying. Like, he just. That. But he couldn't express it, so it was like. It was like he couldn't. And I was so angry at him for so long. For not telling you certain things. Yes. And not listening to me the right way and all this stuff. And I'm just so. He lived into his 90s, and I'm so glad he did because I feel so good with where our relationship was by the time he passed, because I put down the bag, you know, I was like, let it go, Jen. Like, he is doing his best, the best that he can, and he loves me. And how lucky am I that I have a dad who loves me that much? So it was really, really great. So I just feel like he really taught me a lot about. It doesn't have to be the way you expect it to be. It can be different. Somebody can love you differently than you would love them, and then you expect it and to be grateful as that they do.
Lewis Howes
Yeah.
Jen Sincero
Yeah.
Lewis Howes
That's beautiful. I love that.
Jen Sincero
Yeah.
Lewis Howes
I want to ask you about coaching because I've heard coaching a few times as an athlete. I know the value of coaching from sports into business. I have a relationship coach. I have a, you know, health coach, nutrition coach. I have coaching in every area because coaching worked for me as an athlete to get to my goals. And Accomplish the dreams that I had in sports. So when I transitioned from sports into life, the first thing I did is look for mentors and coaches to guide me on my path. I don't think I'd be where I am today without having great coaches and guides. Do you think we should all find a money coach or have some type of coaching within money? Whether that's a financial advisor or. Or maybe it's reading your book around money or listening to content about money or. Should we have guides and coaches?
Jen Sincero
Yes. I mean, especially if you're not making it, like, right, you need money and you. You need it now, you know, so get a coach. Like I always talk about, Olympic athletes have coaches. Why do you think you and your scraggly little. Trying to scrape it together? Why do you think you don't need one? You know, that's what got me doing it. I was just like, who am I kidding? I've been trying for 40 years on my own, and I couldn't do it.
Lewis Howes
Right.
Jen Sincero
Yeah, No, I think coaching. I think coaching. Because also, we all know what it's like. Like when you're saying, you know, how would I coach somebody who's going through what I'm going through? Super easy. Right. When it's not me. So that's what a coach also does, is like, they see they're not in your forest with all your trees. Like, they're looking at it without all your around it, you know, so they can see it so much more easily. And so a good coach can save you so much time and money in the long run.
Lewis Howes
Do you have a coach right now?
Jen Sincero
I don't have a coach right now. Yeah. But I'm still in that sort of incubation. So I need a coach to help me figure out what I want to do. Yeah. No, but I'm not scared of hiring that way. Man.
Lewis Howes
I love hiring. But you're in a season of discovering and reflecting on what you want next.
Jen Sincero
Yeah.
Lewis Howes
You've done so much in the last decade and.
Jen Sincero
Yeah.
Lewis Howes
And now you're figuring out, okay, where am I at, what I want to contribute or how do I want to show up?
Interesting come to you.
Jen Sincero
It's fun. And I'm still. And you know, I'm still doing stuff. And I really believe in not sitting around and trying to figure it out. Because when you're about to do something new, you don't know what it is. You never done it. So you gotta go out and do stuff.
Lewis Howes
Try things.
Jen Sincero
Try things. So I'm out there trying things for sure. And I'm, you know, and I'm still doing all the bad stuff. You know, we've got a lot of really cool things happening in that arena, so. So that's all super duper fun.
Lewis Howes
That's great. That's great.
Jen Sincero
But just, you know, living the dream.
Lewis Howes
Jen, I got a couple final questions for you.
Jen Sincero
Okay.
Lewis Howes
What is the thing you're most proud of that most people want to know about you?
Jen Sincero
I would say that I'm a really good friend. I have friends. I have lifelong friends from forever. And a lot of them. And we're just like a family. And I have. I feel like I'm an art collector and I have all these masterpieces of humanity that I just. I pick good ones.
Lewis Howes
That's a great.
Jen Sincero
And I keep them around because they're really important to me.
Sponsor Announcer
That's cool.
Lewis Howes
Yeah, I like that explanation of it.
You're an art curator of humanity. I am.
Sponsor Announcer
I like that.
Jen Sincero
I'm telling you. I want to have an unveiling, which will just be called a party to.
Lewis Howes
Some people, but I like that a lot.
I asked you this question on our previous interview. That was a virtual interview. But I'm curious your response to it now.
Jen Sincero
Okay.
Lewis Howes
So we'll have to reflect afterwards on what those answers were before to where they are now.
Jen Sincero
Pressure thought.
Lewis Howes
This question is called the three Truths. So imagine a hypothetical scenario. You get to live as long as you want to live on this earth. But then one day you turn off the lights in this physical world.
Jen Sincero
Okay.
Lewis Howes
And you get to create and achieve and accomplish all the things you want to do. But for whatever reason, all of your written, audio and video material has to go with you.
Jen Sincero
Okay.
Lewis Howes
From all your books and this interview. And everything is gone. Hypothetical scenario.
Jen Sincero
Okay.
Lewis Howes
But you get to leave behind three truths. Three lessons you would share with the world. And this is all we have left of your. Your words. What would be those three truths for you?
Jen Sincero
Well, let's see. Three truths would be the most important thing to develop if you want to really live an awesome life. Is your mindset. Really develop your mindset and pay attention to it.
Do the scary thing. Definitely do the scary thing every single day. And.
Have as much fun as you can. Like, what else are we here for?
Lewis Howes
Yeah, that's beautiful. You have.
Again 10 year anniversary of youf are a badass. You've got other amazing books as well. You're a bad at making money. You're a badass.
Sponsor Announcer
Every day.
Lewis Howes
Bad habits. So many amazing books. Number one Yorktown bestseller. You've got an amazing course I believe as well.
Jen Sincero
Coaching course, group coaching course.
Lewis Howes
So fun at Jen sincero.com S I N C-E-R-O.com where they can get that information. What do they get in this course, in this coaching?
Jen Sincero
Well, I'm doing it live now, which I haven't done in eight years and it's so much fun. I missed coaching. I really miss talking to other people. And it's. I've been selling it as a DIY course for a while, but now I'm back in it. So basically you get. It's eight weeks long. You get and we. And what I love about this course is I wrote it right after I finished writing you are about it. So I put in a lot of like time management and sort of like, you know, brass taxi kind of thing. And every other week is a spiritual element. So you start applying the spiritual to the tactile. So because I really feel like, you know, we talk about all this stuff but unless you're actually doing it while you're taking action, who cares? So people, it's been so much fun. So basically you get a video at the beginning of the week, you get a PDF with the video and then every other week you get a 90 minute coaching, group coaching call with me.
Lewis Howes
That's cool.
Jen Sincero
That's recorded so if you can't be there, it's fine. Or a guided meditation or a guided motivational.
Sponsor Announcer
That's beautiful.
Jen Sincero
Something or other. Yeah, it's really fun. And a Facebook group where you can hang out with the other people in the course.
Lewis Howes
Everyone could use more coaching from you. You this energy, I love it. You're also on social media everywhere, Jano, everywhere. On Twitter, Instagram, Facebook. What's the main platform you hang out the most?
Jen Sincero
I like Instagram the best. Yes.
Lewis Howes
Okay. Make sure to follow you there. So if you enjoyed this, make sure to follow, share a story. Leave a message about your biggest takeaway from this episode on social media and also in the comments below over on YouTube. I want to acknowledge you, Jen, for your journey. You being an example of what's possible for people, someone you know your whole life until you're 40, really being stuck in a mindset and having the courage to break through, through taking action on your fears consistently, through investing in yourself, through investing in coaching, through being willing to risk, feeling vulnerable, feeling overwhelmed, feeling embarrassed, feeling like a failure at times and doing it consistently over the last, I guess 15 plus years now. So I really, really acknowledge you for you being a channel to share this work with the world and impacting so many people along the way. It's been a beautiful journey to watch. I'm a fan of you, your work, your books. It resonates so much with me, so I acknowledge you for the gift that you are to humanity as well. It's beautiful.
Jen Sincero
Thank you so much.
Lewis Howes
You're welcome.
Jen Sincero
It's so nice to meet you in person. You're like the easiest but you're totally kindred. You are like you're just there all day. Yeah.
Lewis Howes
My final question is what's your definition of greatness?
Jen Sincero
Allowing yourself to be, do and have everything that lights up your little heart.
Sponsor Announcer
I hope today's episode inspired you on your journey towards greatness. Make sure to check out the show notes in the description for a rundown of today's show with all the important links and if you want weekly exclusive bonus episodes with me as well as ad free free listening experience. Make sure to subscribe to our Greatness plus channel on Apple Podcast. If you enjoyed this, please share it with a friend over on social media or text a friend. Leave us a review over on Apple Podcast and let me know what you learned over on our social media channels. Lewis Howes I really love hearing the feedback from you and it helps us continue to make the show better. And if you want more inspiration from our world class guests and content to learn how to improve improve the quality of your life, then make sure to sign up for the Greatness Newsletter and get it delivered right to your inbox over@greatness.com newsletter. And if no one has told you today, I want to remind you that you are loved, you are worthy, and you matter. And now it's time to go out there and do something great.
Mrs. Claus
Hey there, it's Katie Nolan, host of Casuals, the sports podcast where we don't care how much you know about sports sports, we're just happy that you're here. Every week I hang out with some of my good friends to discuss the biggest stories across sports and entertainment, but in a way that's like fun and not boring. Want to know Sue Bird's favorite Diana Taurasi story? Or how heavy the Larry o' Brien trophy is? Or even what baseball team is right for you based on your moon sign we got you. Listen to Casuals every Tuesday and Thursday on the SiriusXM app or wherever you get your podcasts.
Jen Sincero
Bye.
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Podcast: The School of Greatness
Host: Lewis Howes
Guest: Jen Sincero
Episode Title: The Identity Shift That Unlocks Wealth
Date: December 5, 2025
This episode explores the deep emotional and psychological barriers around money, featuring bestselling author and coach Jen Sincero ("You Are a Badass") in an in-depth conversation with Lewis Howes. The discussion unpacks why so many people struggle to feel deserving of wealth, how our identities shape our financial reality, and the crucial role of mindset, emotional healing, and taking risks in transforming one's relationship with money.
“When you desire money, it’s not the same as being greedy, but I think that we combine those two things.” – Jen Sincero [03:05]
“We are buying into an identity as somebody who can’t afford stuff ... that becomes my reality.” – Jen Sincero [08:32]
“You’re killing off your old identity. And ... the main reason [people don’t support your growth] is you’re killing off the person they love.” – Jen Sincero [09:28]
“Are you going to stay small ... or is your comfort and growth more important?” [11:36]
“I tripled my income in like three months. And then ... I kept doubling my rates and kept cold-calling.” – Jen Sincero [14:09]
“To think what you want to think is to think the truth, regardless of appearances.” [29:35]
“You do not get to work out physically and then stop going to the gym once you’re in shape … spiritual gym workout, meditate for 15, read a self-help book for five ... do them every single solitary day.” – Jen Sincero [49:43]
“If we all did something that scared us every single solitary day, our lives would change so quickly, we wouldn’t know what hit us.” – Jen Sincero [53:17]
On Identity Shifts:
“It's a total identity shift ... that I could open myself up to being somebody who could receive wealth. It was a big shift for me.” – Jen Sincero [06:34]
On Sharing Generosity Publicly:
“When you say, ‘Here's what I’m giving,’ it inspires other people to be generous as well.” – Lewis Howes [04:46]
On Emotional Blocks:
“If I get really rich, I won’t need Dad anymore. And it’s like putting a knife in his heart.” – Jen Sincero [16:18]
On Daily Money Mindset:
“If you want your money to appreciate, you must appreciate it and treat it like you’re the greatest lover of your life.” – Lewis Howes [20:47]
On Taking Scary Action:
“If we all did something that scared us every single solitary day, our lives would change so quickly, we wouldn’t know what hit us.” – Jen Sincero [53:17]
This episode gives listeners not just a playbook for wealth, but a challenge: Transform your identity, confront your inherited money stories, and relentlessly practice the inner work as much as the outer. Embrace scary growth, talk openly about money, and see abundance as energy—then build systems to hold it. Ultimately, aligning your actions with fun, meaning, and energy is key to both wealth and fulfillment.