Episode 174 // Figure It Out as You Go with Cathy Heller

May 1, 2018

Today’s episode is one simple (and powerful) reminder: It’s all doable, you just have to figure it out. Cathy Heller of Don’t Keep Your Day Job is sharing the importance of showing up and trying again and again until you find what you’re supposed to be doing. For any boss who has ever doubted themselves, this is an episode you can’t miss.

Learn More about the Topics Discussed in this Episode
This Episode Brought to You By:
"There are so many ways to make a living and find your tribe and do it in an unconventional way."
- Cathy Heller

Discussed in this Episode

  • Cathy's entrepreneurial journey
  • Having the drive to figure it out
  • Putting yourself out there before you know all the steps along the way
  • What is the most important thing to being successful besides talent?
  • The importance of authentic human connection
  • How to deal with the comparison trap
  • Taking rejection as information
  • Time management tricks when you're going after so many different opportunities

More from Cathy Heller

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Braid Creative

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Almanac Supply Co.


Kathleen Shannon 0:01
Hello and welcome to being boss,

Emily Thompson 0:04
a podcast for creative entrepreneurs. I'm Emily Thompson.

Kathleen Shannon 0:07
And I'm Kathleen Shannon. I'm Kathy Heller and I'm being bus.

Emily Thompson 0:15
Today we're talking about following creativity, dealing with rejection and finding success as you figure it out as you go with Kathy Heller. As always, you can find all the tools, books and links we reference on the show notes at WWW dot being boss dot club.

Kathleen Shannon 0:32
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Emily Thompson 2:05
Cathy Heller is a firehose of inspiration. She started out as a singer songwriter and found success licensing her music to TV, film and ads. Quickly she became a standout in her field and was featured in magazines like billboard variety and the LA Weekly. She's now the host of the popular podcast don't keep your day job or recently given the number one spot on iTunes recommended list of shows for the new year. Each week, Kathy encourages 1000s and 1000s of listeners to find more purpose in their life and get paid to do what they love full time. Kathy's Girl Next Door approach and out of the box hustling style is helping so many people feel hopeful and excited about what lies ahead. Kathy often says a purpose is the opposite of depression. And she is truly lifting others to be the happiest versions of themselves.

Kathleen Shannon 3:03
Kathy, welcome to the show. Hey, thanks for having me on. So you also have a podcast and it is called don't keep your day job. That's correct. So tell us a little bit about like your entrepreneurial history. Have you had a day job? Did you quit your day job? What was that? Like? What are you up to now give us like the whole story in a nutshell,

Emily Thompson 3:27
the rundown.

Cathy Heller 3:28
It's always so fun to be asked about yourself, isn't it? You're like, ah, Is it my turn? Well, okay, here we go. Again, yeah, that's why I love doing a podcast because people love to talk about their life. I feel like everybody's always saying like, do you see me? Do you hear me? Do I matter? So thank you guys for making the space for me.

Kathleen Shannon 3:49
You we hear you and you matter and everybody's stories resonate in different ways, right?

Cathy Heller 3:55
Totally, totally. It's really so special to like, just like, uncover everybody's adventures. So yeah, all of those things pertained to me, I've had day jobs, I've quit day jobs. I've started my own businesses. And I have a podcast and it all started. I was born at a very young age. But um, when I was a kid, I love to write music. I thought that every kid did that, like walked around, like scribbling down notes of lyrics. And I turned out that's not exactly what every kid did. But my parents had like a really just not good. It's like an uncomfortably horrible marriage. My parents wanted it was splitting up and it was not so fun. It was a kind of a like a rough time. And music was always this thing that would make me feel better. And I used to think like one day, I'm gonna get out of here and I'm gonna write songs and people will hear me and I won't be invisible and I'll fill up stadiums and that'll just be sort of my way out. You know, it was like what kept me going and the music felt such Good released to express myself and my parents. Well,

Kathleen Shannon 5:04
where were you living at the time? Were you in LA? No,

Cathy Heller 5:08
I would never. I never have been here till I moved here with like a suitcase and nothing like 500 bucks. Like the stories all tell. I grew up in South Florida in a suburb. And it was like not very, there's no like counterculture, like the we had like a Chili's. And like a, our biggest cultural thing was like a borders, books and music. You know, it was like, hard to be an artist there. And I felt really like other all the time. Anyway, my parents wanted splitting up and I went through some stuff. My mom was, like, always suffered from depression. And there was just so much like gloom and doom, like nobody felt like good. It was just kind of like, you know, there's no spirituality. There was no real reason for anything. And I was just kind of like, this can't be it. This is like such a bummer. Anyway, I barely graduated from high school barely showed up to high school, the day of graduation. I wasn't supposed to graduate because I had so many unexcused absences. And my grades were terrible. And my teacher had pity on me and said, Get the hell out of here. I know, you don't want to stay here. I know you want to get out of this town. And he passed me. I should really thank him for that. Anyway, I went away to a state school. And I barely got in, I had to go to like academic probation just to like stay. And I just started studying stuff. Anyway, when I got out of college, I was like, I'll move to LA. I want to be a rock star. And we and so did you end up studying music in college. So I started out doing like musical theater. And I loved the theater people because they felt like my people. And then I started taking classes in eastern religion, because it looked really like cool to have like some perspective on why the heck we're here. And that led me to like a comparative religions major. So I ended up studying all the religions of the world. And it was just cool. Like, I got to read books on meaning and write papers on purpose and get a college degree. But I didn't know what the heck I would do with that. So I still stay true to like the I'll just be an artist. And I was in a band in college. And I wrote for the college newspaper, and I tried to be like an activist and make friends and do college stuff. Anyway, I came to LA with no one not like a parent paying the rent, and not a friend in the music industry and no way of knowing anything. and got a job on Craigslist, and started paying my own bills and started trying to figure out how to get a record deal. And this is where my show sort of begins. My show I podcast started a year and a half ago, but the premises and the things that I like discovered I teach, which is you don't have to have these resources that you think you need. like everyone's like, well, if I don't have the time and the money and I don't have the contacts, then I'm just doomed. And that girl over there, she just got lucky because she has a parent who knows somebody or she's got someone who gave her a trust fund. But guess what, you don't need any of those things. You could have a mom who's manic depressive, and who barely can take care of herself, let alone you and a dad who you don't know where he is. And you can have no money and you could still figure it out. Because when we have when we have a really big sense of determination and we are resourceful, we can kind of figure out anything. And so I hate when people say well stop being so idealist and people sometimes just can't. It's just, you know, they have to, like, succumb to the inevitable. And I say no, no, no, no, that's that's not true. So I got a job. And the other thing is that people will say like, well, there's no real way for me to do it. It's either where I am or being Beyonce are where I am or being Ilan musk. There are so many ways to make a living and find your tribe and do it in an unconventional way. And that's what I figured out. So I tried to get a record deal because the only thing I knew about being paid to write a song, or being artists was getting a record deal. So I worked super hard to do that. Just trying to meet anyone who I could write a song with and then trying to find money to create a record with and just trade demos, and trying to figure out who the people were in the labels who How do I get a meeting and I don't know that three years later, after writing songs and songs that were mediocre, and then better songs, I finally got a record deal. I got a record deal with Interscope, and I was sitting there like in the recording studio with Ron fair, like watching him record Lady Gaga, Papa Razzi. And I was like, here I am. And it worked out and oh my god, that was like three years, but that's pretty easy. And I'm here and they're asking me what I want from Starbucks, and I'm recording music and I'm getting to watch other celebrity artists. And about three months later, I was driving In my little car, and I got a phone call, can you pull over? I pulled over and he said, we're gonna drop you from the label. And I said,

Oh, no, right. So I said, well, that's that's not good. And he said, No, it's not. It's because the songs are sort of like these, like Michelle Branch meets Lisa Lowe meets Sheryl Crow. And they're sort of like conversational and cute, but they're not like big pop sensation songs. And we're not sure if you're going to be able to do this new wave of like, what's going on on the radio, and so we're not going to take the chance. So we're gonna let you go. And I was like, Oh, no. So once you meet the Wizard of Oz, and he tells you, he cannot get you home, then what do you do? Right? So I thought, I guess that's it. For me. There's no music career, because I didn't see any other path. I didn't, nothing was ever modeled. Right. So there I go. Looking for my other identity. I'm like, maybe I'll go get an MSW and I'll be a shrink because I basically was my mom's shrink my whole life. Or maybe I will get a yoga certification, because I've been doing that for a few years. Or maybe I'll take a class and interior design, because I'm kind of creative. So I try all of those. And I'm, like, so anxious, and I'm gaining weight. And I'm like, not myself. And for two years. I'm like Barbie, like, I'm trying to be astronaut Barbie and vetinary. And Barbie, I'm wearing all these hats and suits. And I'm, like, ridiculously unhappy. And I can't figure out why. Because all of these things could make a decent life, you know. So a couple years into all of that I even got a real estate license, someone's like, well do that, you know, you should always just try that. I do all those things, somewhat successfully. Like I had, I started like teaching my yoga to kids, it was kind of working. And I found little grooves and I still was just miserable. I felt like a fraud, you know? So, um, because I wasn't being myself wasn't in alignment with myself. So I was kind of feeling like, Oh, no. Anyway, two years later, I'm like, having this moment where I'm just like driving and crying. And the sunblock is in my eyes. And I'm by now My eyes are like stinging, so I have to pull over I can't even see. And I said to myself, I have to figure out a way to write music. I have to there's got to be another way. So what you seek is seeking you, like we know from Rumi, right? That's like he's like the most, I don't know, quoted poet of all time. And I, that week, I read a Billboard magazine, which I hadn't even picked up in like three years, because it was too threatening to like, even look at it, I had to convince myself, I don't want that. I don't want to do it that. And so I pick up this Billboard magazine, I see an article about indie artists who are licensing their songs to TV shows like One Tree Hill and Grey's Anatomy. And at eight ad agencies are using their songs for Old Navy. And I'm like,

Kathleen Shannon 12:58
it's funny that you're bringing this up, just because I remember the rise of like the Grey's Anatomy, like bringing some people who are my friends who write music into the stratosphere, you know, like stuff like that is just like wild. Okay, so this is happening. And then what?

Cathy Heller 13:15
So then I thought, finally, something like a light bulb went off because it was models. I saw it. I was like, I never thought of that. I worked so hard to get a record deal. Wait, what if I put all of my like, focus on it? What if I did some research, watch some shows? took some notes, what are the storylines? What are the sounds like production wise? What kinds of songs are being used in all these ads? And maybe I could like intentionally write songs that would fill the vision of these other projects, and then that could maybe pay my bills, right? So I set out to do that. And so I did some like reverse engineering and did some googling and looked at who the artists were. And I was like, okay, so there's like Regina Spektor and Ingrid Michaelson and, okay, so the Lumineers. And what are they doing? And what are those songs about it? Oh, okay, I kind of get what the sound is. That's not so different than what I do. What if I could just like, kind of bring that into the studio with me and be inspired by that? And so then I start googling, like, who are the producers? Who did this record? Who did this record for this indie artist? Oh, I'll reach out to those people. How do I find their emails? Well, I'll look for them on Twitter. You know, I start like doing this reverse engineering and researching. And then sure enough, you know, some people say no, or they don't respond. And a couple of people say yes, like, come on in. And oh, yeah, I get what you want to do. And oh, your sound is pretty okay. Yeah, I could see how we can kind of like, you know, sort of create your, your vibe to fit that. Let's do that. And so I write an EP, which is like five songs. And then I started to figure out like, well, who are the people? What's the name of the person who like choose the song? So I was like, oh, let's call them music supervisor. That's a person who chooses a song for a TV show or, and so I'm like, How hard is it can be to like, there are people right, so like, I'll figure out a way to break through the noise. I'll send them a short and sweet email that has nothing to do with me. I'm not gonna like be myself that like never works, I'll just offer to bring coffee to people's offices, I'll be like, do you want Starbucks like, I'm gonna have a cup pop over. Anyway, I made this like really lame PDF, that's an mochas and music. I'm not a graphics person like you at all, no skills there. And I put a little picture of a cartoon girl with a guitar, and then a plus sign, and then a picture of a Starbucks latte. And I was like, Hey, I'll bring you a Starbucks. I'll drop you off some music and I will be out. I will not try to like weasel my way in for a meeting. I'll just bring you some stuff. Would you like it? I sent that to like 60 people whose addresses I just looked around for. And 26 people responded and said, why not? You could bring me a latte. That's fine.

Kathleen Shannon 15:40
That's a great conversion rate right there.

Cathy Heller 15:43
26 not bad. And I got 26 licenses the next year. They, yeah, they all use my music. In fact, just before I got a text from a friend who said, Hey, I go to my kids go to school with Kevin Edelman. Kevin Edelman is the music supervisor who's done shows like The Mindy Project and How I Met Your Mother, and he gave me my first license. He was one of those 26 people, she just actually got that text today. Anyways. So I start writing more music, more music, more music, and I start making money. And I made like, 200 grand, and then like 300 grand a year. And I bought a house. And I was featured in magazines like billboard, and variety. And I'm talking like, like in my office over here, if I turn the computer, which your fans can't see, but there's like several magazines where I was like full

Kathleen Shannon 16:36
page features. So cool, right?

Cathy Heller 16:39
So by for figuring that out. Yes. And so I had a career and I got to write music. And I could still go get milk at the story because nobody knew who I was. But I was like making a great living like I was like a lawyer salary, doing just being a Disneyland everyday. Which to me being in the studio is like being a Disneyland. And then I started being asked to speak people were writing articles about me. And the articles were titled like writing her own check, DIY hustle. Like, I did this all by myself. And how did you do that? And I'm like, I don't know. I like people. I'm not afraid to be uncomfortable. I work really hard. I had no one to like, fall back on. So

Kathleen Shannon 17:20
I just wait, I have a question. You're getting like this publicity and attention for someone being kind of behind the scenes like you can buy milk and whatever Do you have like a PR team now at this point pitching you? How are these articles coming to you?

Cathy Heller 17:33
So I also did that. I was like, What? See your liking yourself? Yeah, I was like, why can't I look at like who the music editors are different magazines and blogs and just see if this is interesting. And again, when you're sending I'm good at sending emails. It's not about like long winded like, hey, it's not. It's like if you went to a dinner party, you wouldn't say to someone like, What's up? What's your name? Tim? Cool. Do you have 10 minutes sit down for a second. Okay, so here's this is everything. And you just wouldn't tell people your whole CV, you'd be like, you try to look for how you guys Connect, and you'd ask them questions, and you'd make it more about them. So my emails are usually really personable. And they have nothing to do with like music. Like if I sent someone an email today, I have three little girls, I would probably say something like, Hey, I'm a mom of three kids. When I'm not braiding hair and singing frozen songs, I host a podcast Do you want to be on it? Like I just talk like a person. And I don't really try to impress people because nothing is impressive, really, at this point except for connection. Because especially like if you're writing to somebody who's chooses songs, or us person that who's writing to an editor or a billboard and you say anything about like, they're they've heard all that right. So it's more about like, your superpower is you like trying to get you in there and then try to connect with them outside of the business thing of a jigger. So I sent like, 500 emails, and I don't have a constant contact, I just send like an email and it takes time. It takes after right like 20 a day for a few weeks. And then I send emails. And sure enough, I heard back from like nine or 10 people and they were like in the biggest magazines for me for music variety, billboard USA Today, music connection LA Weekly, it worked out well for me. Anyway, I got asked to speak and from speaking, I wound up thinking, what else can I add to this? Well, artists are asking me if I could pitch their songs. So I started an agency, I now have like five people who work for me full time and we represent about 60 artists, and we've helped them make lots of money. So that's been great. And then from there, I said, What else could I do? I was like, Well, people keep not getting it and they send me songs and they're not exactly right. What if I started a course. And I like to teach people ahead of time proactively how to know what to send, what songs to be working on how to do that engineering of like what what they need and solving problems because successful people are not looking for opportunities. They're looking To solve a problem for someone else, and so I started an online course, which again, I had no idea how to do it. I was like building the engine while flying the plane, like trying to figure it out. And the course made, it made over a million dollars in its first year, which was ridiculous. I mean, it was crazy. And then one of my students from the course said, you should start a podcast, because you're really inspiring. And like 85% of this has nothing to do with music. It's just about like, if you're creative, how do you like get that? Sort of like stuff out of your head to get beyond yourself? And keep staying in it? And how do you reverse engineer? And how do you send an email? How do you pitch yourself? And how do you. And so I realized that there's four ways to make a living, you could be the maker, like you can make the song, right, you could be teaching how to write songs, like you could be a dancer, or you could teach dance, you could be a potter, or you could teach pottery, then you could be a curator, like in my agency, I'm curating like, I'm helping other artists to get their stuff, you know, to the right person. And then there are some people who they're not songwriters. And they're not teachers of songwriting, but they just want to be the curator, they just love that. So they're either a music supervisor on the other side, or they're an agent. And then you could be an investigator, which is what I started doing with my podcast, which is like, maybe you're not going to make pottery, teach pottery or curate pottery, but maybe you just love it, you want to talk about it, you want to create a blog about it, you want to write a book about it, or you want to start a podcast about it. So there's like four ways. So I realized that from like, my own life, and so I started a podcast called don't keep your day job. And it's been a year and a half. And it's been just the most fun thing. And every one of these things was a side hustle. Like I had jobs, you know. And then I would like, finally have enough of a runway that I would jump off the lily pad to the next job. And then I just kept adding other things as side hustles, including, I have three little kids, like I have a 17 month old, a four and a half year old and a six and a half year old. And it's all doable. You just have to figure it out. It's not it's it's a juggling act. But that's it. I'm done. That's my story. We're not done. We're not even done yet.

Kathleen Shannon 22:14
I have a list. So you go first, Emily, and then I'll get to my questions. Oh, no. I mean,

Emily Thompson 22:20
I think one something you just said about like, you can figure it out. I think one of the things that really stands out for you is that you wanted to figure it out, where you had found a place in your life where you know, you weren't happy and you recognize that you weren't happy, and you wanted to fix it, and you would do anything it took to fix it. I think I find that super inspiring. And and I love that it's given you this perspective of just being uncomfortable and going for it. And at the moment, that's all I have to say no questions, I usually just soak all that in for a second.

Kathleen Shannon 22:54
Okay, here's what I've got. I there's something that you said about just this resourcefulness. And that is something that we value so much as creative entrepreneurs, and it's the thing that we have found really makes us successful. It's like that kind of grit and resourcefulness. But something I've been thinking about lately is I think that they're even probably Trust Fund babies, not about say like, oh, boohoo Trust Fund babies. But if you don't have that kind of like resourcefulness, there is no amount of money that is going to buy you the success, or the creative career that you crave. Like there is a part of being in it and figuring it out as you go, that is a part of the process that makes you who you are. And so I was wondering if you could touch on the idea of really figuring it out as you go as a part of the actual career itself. Because for me, there's so often we're like, Okay, I need to figure this out. And then I will be where I want to be. But lately I've been thinking like, Oh, wait, figuring it out is a part of the thing. Does that make sense? Totally. Yeah. No, I

Cathy Heller 23:58
think that everybody struggles with this. In fact, I think this is like one of the biggest issues. I mean, I feel like there's so much good stuff that never sees the light of day, because people are thinking like, but I can't put that out until I figured this out. So there's so much good stuff never sees the light of day like the end, you know, like and then it just doesn't get out there because people are second guessing it or overthinking it. And I think my one of my like, I guess greatest skills is like this. I'm not trying to be perfect at anything. So I'm willing to sort of like put it out there and like Emily, you know, just said, which I thought was like a really good point to highlight as being being okay with being uncomfortable. And I think that that's really an important thing. I think that we have to sort of embrace that. And the thing that's, I think like really missing if you don't sort of put stuff out there while you don't have it figured out is you're not going to get that sort of really important beta piece. The beta is just like the most important part. And so we're all in beta. I mean, I'm still a beta human being and my wife and mother and podcast, it's always a beta, right? We're always trying to grow and level up and all that stuff. But it's really like crucial that we sort of, we do stuff. And then we sort of put it out. Because we've got to get that assessment, we've got to get that feedback, we've got to figure out, like, what is going on, instead of like, if you're sitting here. And before you hit go, you're trying to know the next 18 steps, like, what if you have this, it's a blog, or it's a script, or it's an Etsy shop, and you're gonna wait until you have all this stuff figured out. And then you come to find out when you finally feel like you're ready, whatever that means, because no one is. And then you find out that there's like this one product, that's the thing that everyone resonates with, like they just wanted those stamps, you made those rubber stamps. So you spent all this time trying to be ready and prepared, whatever that means. And you needed that feedback, actually, because that's the thing. So if you don't put stuff out, you're robbing yourself of that thing. That's actually going to crystallize everything. So I think that we've got to do and do and then just get dirty and messy and put stuff out and then grab that feedback, because not only will you get the assessment, and then you can like make tweaks and changes, but you get momentum, right. It's amazing how so many people are afraid that it's not enough. And there's like tribes waiting for all of us who are really like, they're actually happy with what you have right now. They think it's enough. And like, while you're working progress, like you're now gaining momentum, and you're able to, like, get this one thing happening. Like I remember when I had you on my show, and you were like, try to make $100 you know, like, right, like, so there's stuff that can start happening, which gives you that little confidence every time and then you can go Oh, I'm so glad I put it out there now, because I come to find out that I mean, for me as a songwriter. When I was like starting and sharing stuff I'd like write a song and share it, write a song and share it. And there were so many times where somebody would say, you know, so I'm glad you shared that with me, because we would never use that song. Here's why, you know, like it has this thing needs to be fixed or this thing. And I'd be like, Oh, I'm so glad I told them now before I wrote a whole record. And then I was stuck. Right? So, um, let's all just decide, you know, let's make a decision that Enough is enough. And we we need to be uncomfortable and a mess. And the world I think more than perfection. I think what the world deeply craves is authenticity. So if you're humble and you don't have shame around the fact that you don't have it together, I think the world actually goes cool. I got you like I'm the same way. So come right over it. I'll give you sort of, I'll give you the respective telling you what's working and what's not. And you'll be okay. You know.

Kathleen Shannon 28:00
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Cathy Heller 29:25
So I don't think it's because I'm the most talented songwriter, I know people who runs circles around me, and I think that I'm just good. I don't think I'm fantastic or amazing. I think I'm just good. And my songs continue to get licensed all the time. And I see that as other people not showing up because there's no way you know, McDonald's keeps using my music because it's the best music or Target or Walmart or I just heard a theme song for Netflix. It's That's ridiculous. I know so many people who went to Berklee school. Music and Belmont and full sail and all these great music schools who are just so much better. And I think that it's a combination of two things. I think it's definitely having that grit. Like I my husband says, Kathy, you have the will of a small country, like when you say you're gonna do something. He's very scared of me. Like, she's got that look in her eye, What's she gonna say? And then she knows I'm gonna do it. Um, you know, even with my, my kids, I got married at 30. And just figured having kids would be like, just kind of easy. Like, I wasn't, I didn't feel like I was like, quote, unquote, like too old. But I had issues getting pregnant I had to have. I went through nine rounds of fertility treatment and miscarriages and giving myself injections. And I was like, I'm determined. So I have three kids. And the whole time I went through it. People were like, I didn't even know that like, you don't complain about it. I'm like, everything in my life has been like this. Like, I'm a C student. Like, I don't, nothing comes easy for me. So I wasn't I don't know. It doesn't it doesn't put me off. I'm not like, Oh, God. It's like, of course, you know, like, I didn't even speak to my dad for years. Like he showed up at my wedding. I'm like, Hi, stranger, like I have never had anyone there. So it's like everything is kind of a struggle. So the grip is really important. But the other thing is this, this is the thing that people lose sight of, I think it's super simple. There's a line in the Talmud that says that words from the heart, speak to the heart. And I'm telling you, when you are just present for other people, when you're super genuine, and you're willing to show up, it breaks through that noise. Like I think the way that I write an email, the way that I go to a meeting, it's not salesy. It's It's It's, I'm not there to do my elevator pitch. Every time I meet somebody, I'll be on a plane sitting next to someone we get off the plane, the person says, I don't know why I just felt like I could tell you my whole life story. And I'm like, because we're, we speak the same language. You know, like, I'm a broken soul. You're a broken soul. I love the shit out of people. I love people, you know, people are like obsessed with animals.

And I get that because animals are great. I'm a peep. I'm into people. Like, I think that each one of us is just like, really important. And I just watch how people, they just walk around like feeling like they're not enough, like, no one cares. And I kind of want to, like foster the whole world. You know, I know what it feels like. Maybe that's why. So I walk in with that to every email, every conversation. And I mean it. And then I consistently mean it. So like, I'm the one who recently I called this woman at the ad agency, and I said, how's your grandma, because last time I talked to her, she was like, my grandma not doing well. And sorry, I know, that's not relevant. I was just having a bad day. And I was really close to my grandma, cuz she was like, the only parental person my parents were like, so consumed with their own stuff. And so when my grandma died, I know how like, that was like hard. No one loves you like a grandparent. It's like different. So I called her and she said, I just started crying that you called me like, I can't believe you asked me about that. I'm like, Wow, I can't believe I'm the only person who asked you about that. Like, that is weird to me. People are in so much pain. And it's so unnecessary. Pain in life is inevitable, there's going to be pain, there's going to be yucky stuff, hard conversations, traffic. But suffering is not necessary. And the suffering comes because we really feel alone all the time. So I just don't front, like I don't post on Facebook, and curate the most perfect parts of my life. Like, when it's my anniversary with my husband, if I post something, I'll say, God, it's the hardest work, we have such a hard time seeing each other. And once in a while we do and then it's great. And most of the time is so painful, you know, like, it brings up all your stuff. And so I think having the ability to just show the heck up in all your stuff. I think people go oh my god, I don't know why but I like feel good around this person. So we can all do that. That's like the greatest thing you can do. And so when I go on a meeting, like I remember at Interscope, even how I got through like talking to the woman on the phone. And like the way you even speak to people the way you make eye contact the way you I don't know and maybe it has a lot to do with the fact that I did take that detour in college and start figuring out how to meditate and meditating was so painful and caused me so much anxiety and it still can and but just having a little bit of that in my life gives me something of a grounding so I can you feel it when people walk in the room? I think so. And then you can create that ruins for other people, when you're like, anchored in like, it's all good. We're all human. We're all equal. people, when they talk to other people, when they send an email, when they walk into a meeting, they put on their like business hat and their business face. And they try to be this other version of themselves. I don't think that works. There's so much static, I think human beings are looking to connect. So I think if you know that, you're enough, and you show up and you, I think that that actually would then kind of, actually, that really is a new level of grit. Because if you say like, yeah, I'm gonna be gritty, I know, it'd be pretty, be persistent. But then you're really uncomfortable when you have to get out of your own comfort zone and reach out to this person you don't know, like, that's why cold calls or cold emails or going into a meeting. I, of course, I'm uncomfortable on a certain level, because these are strangers. But I kind of know that if I like feel my feet on the ground and feel my sit bones, when I sit in that chair that I could actually like, make the person's day maybe better, like I could just show up and listen. And so I think people feel that stuff. And I think trusting that you're enough, then I guess, is what it comes down to like, being enough like knowing that, you there, you're an original, like there's never been and there will never be a you write every person has a different fingerprint, literally. Which is kind of insane. Like if you think about that from like, a logical perspective. And then you, you know, question the fact that there's like a creator, that makes no sense, because why do we need different fingerprints, like, we could just have all had the same one. We're different, we're unique. So your, your you is your superpower. So I think I keep that with me. And because I know that about the person I'm talking to I sort of like non verbally let them know that they're that special. And I'm curious about people, and I like people. So I think that the people part, and the grit together, I can like push through any door, you know, and I want other people to kind of know that stuff. So.

Emily Thompson 37:02
Okay, I have a question about this amazing grasp of authenticity that you see. And is it something that you were just born with? And you just get it? Or is it something you've had to cultivate along the way?

Cathy Heller 37:15
Well, I mean, I think it's like a combination. I it's a combination of a few things. First of all, my parents are new. Our new yorkers, we moved to South Florida early, we're supposed to retire there, right. But we moved there when I was a kid. So the New York thing is my whole family, all extended family that's like brings in a little bit of that like just realness. We're also I'm Jewish. So there's like a lot of again, just like, that's part of the culture is kind of, you know, you put out your opinions, you say how you feel you're sort of encouraged to talk to adults. And then I think having parents who made me their therapist, in a way was so uncomfortable, and awful and painful. And I'm still in recovery from that. But at the same time, I learned how to handle feelings that were probably too much sometimes for other people. And then I sort of got really good at taking care of other people making a space like, I'm the one who when someone's just in it, they know that I won't try to cheer them up. Like I'll hold that space for them, I'll let I'll let them have a ugly cry or just Yeah, like life is not always great. So I can be with that. So that that's helpful. You know, I don't feel the need to make everything rosy all the time. And that's part of my childhood. And then I think cultivating like a spiritual practice in my life makes that you know, just easier on many levels. I spent also I took like a summer trip to Jerusalem when I was in college and went back after college and stayed there for about like two years before I moved to LA and learned how to I don't know just see the world differently and integrated it a little bit into my self. So all of those things, I think help but when you when you really grasp the the specialness of every human and you also have a capacity to be with pain. I think it helps you show up. Really, you know.

Kathleen Shannon 39:39
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Cathy Heller 41:10
That's really kind that's such a. I mean, that's such a nice reflection. That's really nice. Yeah, I don't feel sorry for myself, you know why? No one's crying for you, you know, it's like, we have Wi Fi, we have running water, there's people who don't know where their next meal is gonna come from. And no one's crying for anybody. And it's such a waste of time. And, you know, part of it is I saw that in my family. You know, there's other family members of mine who just lick their wounds, and they play that victim card, and it just really doesn't serve them. And everyone's had everyone like everyone, you walk by today, or you pass in the cars next year. They're all hurting, like everyone's got their own flavor of suffering. And so it's not really relevant. It's sort of like, so what, what are you going to do with it. And part of the beauty of having parents, you know, my dad who walked out, and I didn't really hear from him for a while, and he was never really there to begin with. And he's actually deaf, too. So that's another level of like, not really being able to hear that causes him his own pain and his own rage, and he has his own issues. And so I really feel for him too, even though I also have really hard time with how he expresses himself. But when no one's really cares, I'm not going to like sit there and go, Yeah, tell me all of your problems. And I really got to keep feeding that you've learned to, like, get over it, because it's not going to pay the bills. And yeah, that's a great unifier. We're all suffering. So it's time to like, yes. And okay. Yeah, that's what the mind does. The mind likes to chew on stuff. And it's such a waste, and we could sort of focus on other things. And then there's like a plasticity to your mind, which is amazing. And you can actually, like, give yourself more oxygen, like, really, like, it's just amazing, but you have to, you have to work on it. And it's not easy, and it sucks sometimes. And it's okay, you know,

Kathleen Shannon 43:02
I want to pull back out to the business side of things. And yes, I love the comparison trap. Because even I have to admit, whenever you said, you know, and then I launched this course, and it made a million dollars. I was like, Well, shit, you know, like, I went into that place where it's like, I'm Beyonce, or I'm nothing, I'm launching a million dollar course, or I'm nothing, you know, like, it's easy to find yourself going there, no matter probably how successful you are, you're probably always falling into that. And I think that that can be really discouraging. And I think it's like almost, you know, you've been touching on rejection. And I feel like that kind of inner comparison is almost like rejection before you even get started. But have you ever struggled with comparison? Again, I don't feel like you probably do or you don't spend a lot of time letting that get in your way from, you know, continuing to show up. But what would you say to someone who is struggling with like, oh, man, I might not ever make even $35,000 a year doing what I love? How would you kind of advise them to keep going?

Cathy Heller 44:09
Yeah, I mean, I feel like those are two questions. Two great questions sort of put together. And the first question has to do with comparing yourself and the second question is like, I think you were saying like, what if I'm, you know, looking at all these people who are already doing it and feeling like there's not enough room for me and I might not make that much money? How do I keep going? So those are two great questions. The first one is, of course, I struggle with that I struggle with everything. I'm, you know, such a work in progress. I just don't stay in the struggle. That's what it is. You know, like, I've trained myself to have different habits. But of course, I start to feel down and lousy and then I go, Whoa, what's this? I'm taking a shower and everything's fine. Now there's like this awfulness in my shower. It's like, I can't enjoy it because I've got all this stuff in my head. And then I'm like, okay, and sometimes it stays for four hours, sometimes days for a couple days. But I notice it, you know, I have an ability to Like, cultivated that ability to like notice it and go, alright, let's see what we're gonna do with that, you know, but you know, even with you guys actually, like when I first started a podcast, I saw you guys sort of like up on the charts, I was just starting, I was like, how am I going to do that? You know, how am I going to like, look at them, you know, look at how shiny they are in the top, like, you know, 50 shows.

And there's always that feeling, you know, and now some of my other podcast friends like Jenna Kutcher, like, there's friends of mine, Seth Godin. Like I actually talked to him today. But there was a time where like, he was one of those people like, oh, like what he's doing, you know, what about me? comparing, here's a couple things that so here's a couple things, we compare our behind the scenes mess, to people's highlight reels. So that's not really fair, right? We're not comparing apples to apples, we're comparing like, this is what you think it looks like, this is what you see. And then you're in your stuff. And you're like, Oh, no, this is terrible. Those are so not the same. When you see somebody, you know, win the Olympic gold medal, you don't see Serena Williams, when she's like, literally like going to cough up blood because she can't do it anymore. And she's on the court, and she's working out and she's crying, and she's going up against herself. And it's always you against yourself. And there's all that stuff. And we don't see all those moments. So that's First of all, we need to like, really, like, give some reverence and respect and really honor the work and not throw ourselves under a bus and go, Well, it looks so easy. And if it's not easy, and it doesn't come quickly, for me, there's something wrong No, like, that's a very millennial thing like Fred Astaire, if you watch a Fred Astaire like, number from like, you know, the, the 30s 40s he is a master. Right? And and if you watch people who are masters of things there should be a respect for It's okay, give yourself some grace, things take time. You know, and if you keep working hard, and then you listen for feedback, listen for what the world is saying, Yeah, sometimes you're trying to be an actor. And then the world says, huh, that doesn't happen. But maybe they're saying, be a writer, be a writer, or maybe they're saying, Don't be an actor, be a director. But like, if you if you if you do and you do when you do, and you assess, you will get led to where you're supposed to serve. Right. So that's number one. But don't don't look at somebody else and compare and go What is wrong with me? Because there's, you know, it's like, I heard this great little story. I'm sure everybody's already heard it. But like, someone walks up to Picasso and says, Hey, he sees sees him in a restaurant, you know, can you can you doodle something free on this napkin, he doodle something, and the woman goes, That's amazing. And she's about to walk out. And he's like, that'll be $48,000. And she says, $40,000 that took you like 30 seconds? And he said, No, I took me my entire life to be able to doodle that for you in 30 seconds, because it took a long time to become Picasso. You know, not everybody is born. Mozart. Right? Some people it takes us time. That's good. That's great. We should we got to get prepared for that. So I'm always like in it for the long stretch, and I'm in it for I take that ego out and go Where am I really supposed to serve? Right? So if it's, if it's not going to be a podcast, I trust that by like putting my all in and jumping in with two feet, I'll get told the world will let me know if it's not quite right. And maybe there's one aspect of it that I intuitively knew about, but it's really in a different form. And there's been for everything that's been successful that I've done, there's been like 12 things that never worked. Like. I started a show at one point in 2009. And it was called the peaceful place. And it was a Mr. Rogers, where I was like writing songs about mindfulness to children. And I actually sold the idea to the Jim Henson Company, and we made a pilot. And then we tried to sell this show to PBS and Nickelodeon sprout and Disney Channel. And they all said, No. And I worked on that for two years. And thank God because I look back and go, I sort of knew that wasn't it, but it felt at the time, like, maybe I'll take this spirituality and mindfulness and this music, and I'll do it for kids. Maybe kids is less intimidating. I don't know why I thought like, maybe that would work. It didn't work. The world said no calf, this isn't this isn't right, something's off. It's not exactly where you're supposed to serve. So I trust that. And I've also to three, I guess it was like three years ago, I wrote a book on songwriting. I wrote a book a full book, I just sat down and banged it out. And I pitched it to live agents and publishers, and no one really responded. And then one person said, Can I see more pages? And I sent it and nobody wanted it? Everybody said no. And then I started a podcast, right? This is like, after many other things I just happened. I'll try that. I'll try that. And two weeks after my first show launches, I get a call from my now lead agent who says, this should be a book. I then pitch like, barely anything like I wrote up an outline and one chapter, sent it to a few publishers and we had a bidding war with like the biggest publishers and I wound up getting a very big book deal. Like I can't even believe how much money they gave me with St. Martin's Press, which is an imprint of Macmillan. To do a hardcover book So, you see that Do you see how like, there's stuff that doesn't work because that might not be your thing. And that's good. That's the world saying, that door, that's not your door, go, go try that other door, that's your door. That's the door. Everyone's waiting for you to walk through. It's sitting there waiting. So that's one thing. And then as far as like,

Kathleen Shannon 50:19
you're so good at taking rejection as information. Like this is another thing from this conversation. They're like, okay, it's just more information. Right. Thank you. Thank you. Yeah, I was listening to Oprah interview, Maya Angelou. And just I kind of know about my Angelou. It's kind of like I kind of knew about Mount Everest, but I didn't really know about Mount Everest. So I wanted to go see it with my eyeballs like, Maya Angelou is one of those, like, I kind of know about her, but I don't really know about her. But listening to her talk. She was just dripping in gratitude. She was like, thank you. Thank you for closing that door. It's gonna lead me to the right one. You know exactly what you're saying here. So I'm sorry. Keep going. Keep That's

Cathy Heller 50:59
beautiful. I love that idea. I love how well you're able to like step back and then put things into these sound bites that could each be like their own like meme. Like, I love that you're like, rejection for you is information. Like, that's great. I love that never

Kathleen Shannon 51:13
coming up with podcast titles.

Cathy Heller 51:18
And I love that if I close my eyes, I would think I'm talking to Drew Barrymore because like you have her voice, it's so cute. You're not the first person you said first not is I know your little list. No, no, it's just this. No, it's not the list. It's like, I mean, I'm a sound person, I write music. So I like to sound like her. She'd be a great podcast guest, by the way. Anyway. Um, so the other part about like, what if, you know, there's already all these people, and I'm comparing myself saying like, you know, I might not make $35,000. So here's what i think i think that there is so much room. It's just unbelievable. Like, the more that I've lived my life, there is so much room for new people and new ideas. Again, like if you're genuine, and you really, you're speaking from a place of truth that is felt that is so rare and so important. And if you're doing that thing that you're supposed to do, you're walking through the door you're supposed to walk through, you will find your tribe, whether it's fashion design, whether it's a blog, whether it's a restaurant, your own coffee line, you're gonna find your tribe, if there is like true passion and enthusiasm, and it's the thing you're meant to do. It is waiting there for you. And the coolest part. Like I mentioned, I, you know, I did a class that made like, over a million dollars in its first year. So that's, I guess, that was a combination of like, something I liked. I was good at that. Also, that was the right door for me, right? Like people were like, yeah, you're good at that. That's, that's something you really do you have to offer. And what's amazing is I didn't need 1000s of people to take the class I needed. Like 850 people like to take a class 850 people out of all the musicians in the world to know about me and decide to spend 100 bucks a month on a class and they did it. And it wasn't that big of a deal. Like it's not that many people 850 humans, like how many people are there who like hand calligraphy and hand lettering or pottery or baking sourdough bread? Like, there's so many people. So how amazingly exciting is that? That like you don't need, you know, even with the podcast, it's amazing how like, yeah, you know, we have a great audience. And we probably have, like, 40 50,000 people listening to us a week, which is awesome. But that's not that many people in the scheme of things, right. And like, if I want to, let's say launch something now, like, I want to launch a course. I mean, if I had like, 1% of that, like, take my course, like that would be crazy, right? You know, but you don't even need that. Like you can have half that and make, you can have 100 people take your course for $100 a month and make $100,000. And I know a woman who I want to have on who's making seven figures because she's just obsessed with hand lettering, and she created an online course that she doesn't even teach. She just likes it. So she brought in people who wanted to speak about it and just facilitated it. And there she goes, like, I mean, it's just, it's all so not that hard. Like, we just got to start. And I guess I always feel like Yeah, why not? Let's just try it.

Emily Thompson 54:16
Right door after door after door. Because I think what I see what I think we all probably see it far too often is people who get a door closed on them and they just sit there and pout about it for far too long. And that's not how you're going to find anything that you're supposed to be doing.

Cathy Heller 54:32
No, that's such a waste of your time. And yeah, there's so much time and energy spent on complaining the spelling of

Kathleen Shannon 54:39
time and energy. I want to know I we need to wrap this up. But I want to know your time management tricks and tips because you have three kids, you're trying all these things. You're sending out emails, you're showing up one at a time, all the things you're doing all the things and so I want to know more about your time. management and because I like asking two questions in one, I want to know more details about your spiritual practice.

Cathy Heller 55:06
Wow. Okay. So as far as Time management is concerned, it's a couple things. First of all, I have a team, I delegate stuff, it's not easy to be a boss, it's hard, you have to learn how to not be everyone's best friend, that's my biggest challenge, because I want to take care of everybody. And I have to learn how to say, you know, here's a boundary, here's an expectation, but I've gotten better at that over the years. So while I'm doing this with you, right now, there's one to five, five other people running my licensing agency, who are also the same people who handle my music, online class for musicians. And then for my podcast, there's three other people who helped me to just, you know, edit shows and come up with some like content that we can put out that maybe be like a sort of a cheat sheet, something that's like extra content from from an episode. And so there's that. So that's helpful. And then for my book, like I'm writing a book, and I have an agent and an editor, and that'll help. So having a team super helpful, I used to have, I didn't have that. And I used to, like literally get chest pains. And I would wind up I had pneumonia twice. And I had shingles like on my face in my eye, like I had the worst kind of shingles, I just would not know how to delegate. So I didn't want to close one business, I would just and I was just couldn't breathe.

So delegating and having like a great nanny, and then also, I have a housekeeper and then also I realized, and it's that's my biggest hurdle, because I had so much guilt in the mom area. And so for a long time, it's only been a year that I've had full time help. Before that I used to have like three days of help. And I tried to get all of this done in three days. And I had to learn to like be with the fact that I really feel better about myself. And happier when I'm working. And my kids probably then will be happier because I'm more fulfilled. So I had to come to terms with that, which was so hard for me, I had a lot of old beliefs around what that would mean. And because I come from a lot of pain, I thought my kids were feeling the same neglect. And so I had to fix that. But my kids don't know what it's like to have a mom who's suicidal. So thank God, right. So they didn't feel that same pain. So I learned that it's okay for them to have a nanny and I picked them up, I stopped work every day at 330. And then I'm on so I at least get I wake up at 530. So I get from 530 to 330 to bang it out. And if you're busy and you only have a little bit of time you get more done. So that's helpful. And I carve out time to walk and meditate which actually gives me the rest of that day after I do that, it gives it more juice. So I've sort of learned that that's my fill up, I got to get my Philip in. So charges my batteries. So um, I would say for me the delegating, and then that's that really helps. And then just prioritizing, you know, like not trying to do every business in one day. So maybe one day I'm recording an episode. And then I need to have like one meeting at an ad agency about this song that we're working on with like Coors Light. But then tomorrow, I'm going to work on my course. And I'm going to come into the course for an hour and try to let go of trying to be everything to everyone every day. It's that's important. Otherwise, you just really get sick and I've gotten sick before and at something. It's hard for people who are really Taipei and excited you can take too much on. So there's that and then my spiritual practice is like it's an interesting thing that you put those two things together because I couldn't do one without the other. And I'll tell you something, that's really cool. So in Judaism with this idea of like the Sabbath, right, and so Christianity took that it's a great idea, right? Take a weekend. It's really you know, the word sabbatical comes from that, right? So I do that. So Friday night sundown to Saturday night sundown. I am with the world the way it is I'm not trying to change it. I'm not trying to create anything. I'm not trying to do anything. So I take a tech break, I unplug, there's no cell phones, there's no video, there's no chat. It's just, this is the world right now. And it's good. I'm going to be grateful for it and whatever's not good. I'm gonna let that be okay. So I spend 25 hours a week, where I am just present and take a walk, go to synagogue, there's an amazing meditation class I do Saturday mornings, I go to a pretty hippie dippie Synagogue. So it's pretty cool. And I just spend that time. So I've got that day. That's like an anchor. That's really important. You know, if God could rest for a whole day and include that in his seven days of creation, that means that that one day doing nothing is important. That's actually part of the creation to stop and take it in and be with it. He didn't say I created the world in six days. And then I spent a day resting he said I created the world in seven days. So there's a day to be with what is like that is a part of everything. Imagine if steve jobs created this incredible apple and he doesn't take any time to sit with it and go Ah, I just breathed that in, you know, we got to take some time. So the spiritual practice, I've got that. And then there's this place in LA called unplugged. It's in West LA. But there's, I go there to meditate. And that's great. And there's also other resources. UCLA has a mindful awareness Research Center, I've taken classes there, try to, you know, have apps on my phone, if I only have 20 minutes, sometimes I'll just try to sit down and meditate. Sometimes it's really stressful, because your mind is like jumping around. But if you don't judge that, and you just notice your thinking, and you just bring your attention back, even that actually helps so much. If you could just get rid of the judgment and just notice stuff. It's fine. Just bring that attention back. So all of that is super helpful. It's like oxygen for me.

Emily Thompson 1:00:50
I love it. And what makes you feel most boss,

Cathy Heller 1:00:54
most boss? Well, recently, I've learned this word, and it's a word that's very underrated and underused, it's called No. And, and it makes me feel really boss to be able to say, and just let it land. no apology, just say, No. Okay, so I'm gonna let you go, you know what I mean? Like that, that is so fierce when I can do that. And that comes in many forms, like sometimes with my kids like, well, I want this other. No. Okay, so we're gonna move on to the night, you know, not known. And then now, you know, there's room for you to argue with it. Sometimes it comes with my husband. It's like, you know, calf, how about this? And I'm like, thinking that's not up to my standard for whatever. And I'm like, no. And sometimes it has to do with business people I'm working with, and someone who works for me, and I have to say, No, it's not gonna work, we're gonna have to do different. So knowing how to put up a boundary, take care of yourself. We live the lives that we are willing to tolerate, and we get what we think we deserve. So we've got to take responsibility for that. That is super important. So you take that on, and say no, and you need to

Kathleen Shannon 1:02:09
write Amen. So good. So good. Kathy, thank you so much for joining us today. I feel like I'm more inspired than I ever have been before with a guest. Oh, my God, this has been change. That is just your story. It's Yeah, thank you.

Cathy Heller 1:02:30
That was ridiculously kind and made me feel taller. And I think you're both delightful, and really doing what you're supposed to do. And I can't believe that you have that feeling about the million dollar class, because I assume that you already done 15 times out. So if you want to talk about that offline, we should because I love talking about it. So that is so sitting there. And Emily, I want to have you on my show.

Emily Thompson 1:02:56
So we'll work I'm down. I'm totally down. Thank you so much for joining us. And last but not least, where can people find out more about you

Cathy Heller 1:03:04
so they can listen to the podcast. Don't keep your day job where you can find it on Apple podcasts or on Soundcloud or don't keep your radio calm. And I also have like a Facebook group for don't keep your day job. I pop in there like once a week you can find me on Instagram at Kathy dot Heller and Cathy's with a C. And that's it.

Emily Thompson 1:03:24
Love it. Thank you. Thank you so much.

Unknown Speaker 1:03:26
Thank you.

Kathleen Shannon 1:03:29
Hey bosses, I want to tell you about the CEO day hit. The CEO day kit is 12 months of focus planning for your business in just one day. So Emily and I have packaged up the exact tools that we've been consistently using for years that have helped us grow from baby bosses to the CEOs of our own businesses. gain clarity find focus get momentum, prioritize your time, make better decisions and become more self reliant with the CEO day kit go to courses that being boss dot club to learn more and see if it's a fit for you and your business. Shout out to this episode sponsors including fresh books cloud accounting go to freshbooks comm slash being boss and enter being boss in the How did you hear about us section two try it for free. Go to 20 twenty.com slash being boss that's 22 zero.com slash being boss to get some really good stock photos and they're gonna get through a few free ones your way and then of course fabfitfun calm enter the code boss so you can save $10 off your first box making it only 3999 Thank you for listening to being boss. Find Articles show notes and downloads at WWW dot being boss club. Thank you so much to our team and sponsors who make being boss possible our sound engineer and web developer Corey winter. Our editorial director and content manager Caitlin brain, our community manager and social media director Sharon lukey and are being counted David Austin with support from braid creative and indicia biography,

Emily Thompson 1:05:04
do the work. Be boss and we'll see you next week.