Episode 131: Building a Creative Career From Scratch | Jess Goldsmith | Founder of Chick of All Trades & Women of Type
Jess Goldsmith didn’t wait for someone to tell her she was an artist. She decided she was one and went all in. With no formal art school training, she built a thriving creative career from the ground up, working as an art director, illustrator, and the founder of both Chick of All Trades and Women of Type. Her story is proof that you can start with nothing but determination, sharpen your skills along the way, and create opportunities that didn’t exist before. We explore how she navigated her early freelance days, landed her first clients, and built a community that champions women in design. Jess shares what it’s like to balance business strategy with creative passion, why mental health advocacy matters in the creative industry, and how resilience plays a role in every success story. For anyone building a freelance design business, growing as a creative entrepreneur, or looking to make their mark in the art world, this conversation is full of real-world advice, inspiration, and proof that you can define success on your own terms.
“I started by choosing it. I told people ‘I’m an artist’. I didn’t allow other options to seep into my reality.”
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Follow along using the Transcript
Chapters
00:00 Claiming the title of artist
02:15 Starting without a formal art school path
04:30 The leap into freelance design
06:05 Lessons from early client projects
08:40 Launching Chick of All Trades
10:15 Building the Women of Type community
12:50 Balancing creativity and business strategy
15:20 Advocating for mental health in the design world
17:45 How resilience shapes creative careers
20:10 Collaborations and dream clients
22:30 Advice for aspiring freelance designers
24:15 Creating work you want to be hired for
26:00 Staying inspired and avoiding burnout
28:40 Defining success on your own terms
How did you know that it was gonna be a good idea for you to like work with us? And I was like, literally, because when I got the email from you guys, I started dancing in my seat. I was so excited. I was, I was so hyped up about it and I still am. And every time I talked to them, every time I have a meeting with them, I'm just like, guys.
That's Jess Goldsmith and this is The Powerful Ladies Podcast.
Hey guys, I'm your host, Kara Duffy, and in this episode I'm excited to introduce you to Jess Goldsmith. She's an artist and illustrator and entrepreneur, graphic designer, art director and owner of Chicken Ball Trade and Women of Type. She's built her successful career. End business as a contract designer based on her tenacity, resourcefulness, and her commitment to her dream to be a career artist in addition to killing it in her work.
She's also a force to be reckoned with, with commitment to supporting mental health advocacy, women's empowerment, and making sure we're all working towards a better tomorrow. If you are a creative like Jess looking to make the leap into working for yourself, having your own business, or taking your current business to the next level, I encourage you to book a call with me@karaduffy.com or check out all the ways I can support you@learn.karaduffy.com.
From private coaching to a business mastermind, I run to free downloads. Online courses are even my Thrive membership for powerful female business owners. There is guaranteed to be an answer for many, if not all of your what's next or how do I or should I? Questions you will have about you or your business?
Not sure where to start. Email me hello@karaduffy.com
Well welcome to the Powerful Ladies Podcast. Hi. Thank you for having me. Let's begin to please everybody who you are, what you're up to, and where you are in the world.
Hi, I am Jess Goldsmith. I am an art director, illustrator and graphic designer, and I'm in New York, Brooklyn, specifically.
I love it. Um, and we of course met because you're one of my amazing coaching clients, and I met you by doing a, um, clubhouse guest panel event for Yeah.
A mutual friend of ours and a past client of mine as well. Um, and so it's crazy to me how we all get connected and kind of passed on to the people that we need. Um, how has that also impacted the rest of your career? Like going from like one connection to the next?
Yeah. Um, it's funny, I'll, I'll find that.
Like I met someone or spoke to someone like three years ago and then. Now I'll have some, like a friend of theirs, message me or email me like, Hey, I got your contact from this person. And I'm like either trying to remember who they are or I'm like, I think I met them, but it was like years ago. Um, and it's, it's funny the way that like we stick out in people's minds like months, weeks, years later.
Um, and yeah, that's, it's, it's pretty cool.
Well, in addition to, um, having your own design business, you also run a pretty significant Instagram account and group called Women of Type. Mm-hmm. Um, tell us about women of Type. How did that start? Why does it exist? Why does the world need it?
Yeah. So, um, I love typography.
I love lettering. It's like part of the bread and butter of what I do in my own business. And, uh, this was like the start of the pandemic. I was just at home and I was like. I wanna be featured on one of these pages. My work's great, but I wasn't being featured, so I was, I, I was just like, okay, I'm gonna create a page and I'll just feature other people and then, you know, I'll stick myself in there sometimes.
And it really like grew exponentially over just like, I think by month. Two or three. There were already like 25,000 followers, which was really cool. Um, I think it's a great way for people to discover new artists, female artists. Um, yeah.
Well, what I'm curious about is how did you become a designer? How did you go from, oh, how did you get to where you are today?
So, um, I've always been a creative person my entire life. My mom. Um, she recently gave me like a scrapbook that I have from when I was like two years old of like my doodles. So creativity has been inside of me my entire life. And, um, I struggled for a little bit trying to figure out what I wanted to do. I didn't go to college immediately after high school.
I like took some time to kind of figure it out, which I didn't, I had no idea what I wanted to do, so I ended up. Being a preschool teacher for a while. Um, then I was selling men's wear on eBay for a few years, and then I was just finally like, okay, I hate all of this. I, or not even hate it, but just like, this isn't me.
Like I'm not feeling fulfilled. I have to do something creative. So like, I went back to my roots of painting, drawing, trying to sell my art. And that's really hard to do if you haven't done it before. You know, like it's, it's, it's rough and the market is so competitive. So I was like, okay, if I wanna sell any of my work, then I need to learn, uh, marketing and I need to learn digital marketing.
So I took a course and through that I had to start designing these ads. And then I was like, oh shit, wait, I love designing these ads. This is so much more fun. Um, so it kind of segued into that in like a weird roundabout way.
And how did you decide, I'm going to do this on my own versus work for any of the potential brands or companies or, you know, even agencies that you could have brought your skills to.
Yeah. Um, in the beginning, I wish they hired me, but nobody got back to me. And eventually I was just like, okay, fuck it. I'll just do this myself. And I mean, it, it's not as easy as, you know, A to B. There were like a million. Pain points that I had to go through, and it was like a rollercoaster. But yeah, that's, that's essentially how it went.
I was just like, okay, I, I have to do this because I can't, I'm, I wasn't getting hired. I wasn't even getting interviews. Um. And now that I'm doing it for myself, I'm killing it.
You are? Yeah. And what I love about you is that, you know, I work with a lot of creative people and a lot of designers, and what I think is amazing about you is that you really have this balanced approach of being creative and loving the design process, but you also really love a lot of the business pieces you love.
Really do. Yeah. Yeah. You love getting the sale, you love doing, you know, PR you love. Do you love the art of the business as much as you love the art you're creating? Is that how you've always been or is that something that you've developed as you've been running your own business?
I think maybe I've always been that way, but haven't recognized it until, you know, I came into like full adulthood and business womanhood and all of that.
Um, real, like looking back, I'm like, oh yeah, that makes sense. But like, I bounced a lot from Think to Thing because. I want it. I, I just like the climb. Mm. You know, so working as a freelancer, yes. I have projects that go for X amount of time, and then they finish and they wrap up. Even if it's a permalance shop, you know, six months, eight months, whatever.
Um, but there's always that climb. There's always that chase and, yeah, that's, I, I really enjoy it.
And you work on a lot of really cool projects. So you do both advertising work, you do production, you do, um, also just like commercial shoots, tell me and everyone listening about like the variety of what you do.
Like I said, lettering is like a big part of like the bread and butter for base. So, um, doing like illustrative pieces, um, either for ad campaigns or just like I. Um, social media pieces that brands wanna use to promote their products. That's always fun to do. Um, and a friend of mine got me into production, so I've been doing a little bit of art direction here and there for commercial shoots, um, photo shoots and like smaller commercials.
Um, but yeah, it's, it's been exciting. It's, it's fun. I, like you said, I really enjoy it. Yeah. And yeah, I get to be creative every day.
For somebody who's listening to your story and being like, I want to make a living doing art. I wanna make a L level, well make a living, designing. Um, what advice would you have for them?
Like where, where should they start?
Um, so I guess it depends on like whether or not you went to school for it. I didn't. But if you went to school for it, you probably already have a pretty extensive network of people that you can reach out to. Um, otherwise I would say. Still reach out to people in your network just to let people know, Hey, this is what I'm doing, this is what I wanna do, et cetera.
Um, but like create work that you wanna be hired for. I wanted to get hired for illustrations for brands. So I just busted out a ton of those and eventually I started getting hire hired for those exact jobs. And now I'm, I have my eyes on like doing some editorial stuff, so I'm like, okay, I need to sit down and create like a series of editorial pieces that don't necessarily connect to anything but could potentially be used, um, in publications.
Well, I love that idea of creating what you want to be doing. Just, you know, basically doing it for yourself and to have it in your portfolio and show that you can. I think the other big question is how do we decide what to charge? Because when you first start, like art is so subjective, it's so hard to be like, this is worth a million dollars.
Yeah. So how have you gone through the pricing journey and how are you still on that today for how you work with different clients?
I'm definitely still on that journey. Um, but I was charging so, so, so, so low. Um, in the, in the beginning it was like less than my hourly rate Now for like a full logo, um, I think, I don't think there's any one answer for what you should be charging, but like, you need to charge your worth and then you need to charge more and then you need to charge even more on top of that.
Um. You know, you're gonna go back and forth with clients being on the phone, going through meetings, going through iterations, and before you know it, like you might think like, wow, what, uh, whatever arbitrary number. Like, okay, I'm getting paid a lot of money, but it's like, how much money are you really making based on the hours that you're working?
Mm-hmm. And taking all of those talks and little things into account and like the brainstorming sessions and sketching things out and, you know, things like that. And I, I think. That can be applied to pretty much like any field. Um, obviously you're not gonna be doing like creative brainstorming and sketching for, I don't know, something else for some other non-creative field.
But it, it can be applied and like, you want, you don't just wanna make a living, you want to have like a really nice, comfortable, dare I say, cushy life. Mm-hmm. Um, yeah. And it's, it's possible, but it's a little uncomfortable in the beginning to like. Um, like, charge more than you feel like you're worth. But once you keep doing it, you're like, oh, yeah, okay.
I'm just gonna keep asking for more money and like, what's gonna happen? They'll say no, and then it's like, okay, is this open for negotiation? Let's see.
Mm-hmm. I know I always get motivated when I hear what parallel brands are charging, and I'm like, wait, what? Yeah.
If you think about like the amount of money that like these global brands have, it's, it's a lot.
There's a lot of money to go around and there's a lot of money for you to get paid. You.
Yeah. Well, you just have gone through, you know, a year and a half of, of going through a pandemic in Brooklyn. Mm-hmm. You in that year, you've gotten married, you've expanded your business like so much has happened.
There's also been, um, you know, some emotional up and downs about what's happening in the world. First question, how did you survive pandemic in a New York City apartment and how did you, how did you grow your business while in lockdown?
So the answer to the first question is barely, like, I barely survived.
It was the first, the first couple of months I, I kind of broke down a bit because, you know, I think like everybody else we're like, it's just gonna be a few weeks, it's just gonna be a few weeks. And it just kept going more and more and more and more. And we're kind of still in it. And yeah, I, I kind of lost my mind for, for a little while and I was not doing well and I was like on a downward spiral.
Um, but taking care of my mental health certainly helped me. Um, having my dog, having my therapist, having my husband, having my medication definitely helped. Um, and then, you know, I did throw myself into my work, so luckily a lot of brands. This is a buzzword, pivoted from, you know, having people in their campaigns to illustrations and drawings and lettering because like, they couldn't, they couldn't have like formal or like regular photo shoots.
And honestly, that helped me. Um, I feel guilty saying that COVID helped my business when I know so many people suffered and continue to suffer. But it, in terms of what it did for me and what, you know, my, where I went with my career, um. Yeah, it kind of blew up in 2020.
Well, and I think it's smart, right?
You were paying attention to what was going on. You didn't,
yeah.
You also pivoted, right? Yeah. Who, who you could reach out to and what you were looking for. And you know, I think so often there's just, especially when we're stuck at home, there's like, what else do you do? Like, let's be in that exploration zone.
Who else can we talk to? Mm-hmm. Who else can I network with? Who can I connect to? You know, like, yeah. Thrive community, um, creativity built that Marika's made where I met you through like, there's a lot of these organizations that popped up because we knew we had to be connected. Yeah. Um, I think it's also really cool that you've done an amazing job of combining what matters to you in the world with the work that you do, um, and one of the, uh, clients that you have to work with right now.
The, um, American Prevention, I'm gonna say it totally wrong.
The American Foundation for Suicide Prevention. Thank you. Um, the, I get it wrong, but it's, it's a, it's a mouthful.
It's, um, but the fact that you care so much about mental health and that you get to work with them and they're so excited to be working with you and like to be able to merge what you really care about and the business that you have into one, like how did you make that happen and how does that occur for you?
Yeah. So first of all, I know you didn't ask this, but it feels amazing. It feels like so much of my life has come full circle, um, where I was in a really bad place like little over 10 years ago. And it's come to where I'm able to help people now that are potentially in that really bad place through my work.
Um. So that's really exciting for me. Um, a lot of my work and what I put out is like mental health based, just because that's so important to me. So they found me through that, you know? Um, and I, they asked me, I did an interview with them and they asked me like. How did you know that it was gonna be a good idea for you to like work with us?
And I was like, literally, because when I got the email from you guys, I started dancing in my seat. I was so excited. I was, I was so hyped up about it and I still am. And every time I talk to them, every time I have a meeting with them, I'm just like, guys, I'm so excited to be doing this with you. This is like, it, it feels like one of the most important jobs that I've had and it's just so perfect for me and who I am and what I advocate for.
And it, and it's not that you're doing this pro bono, like this is a legit paying client. Yeah. Like it's the trifecta of everything that you want. Yes. They're, they're paying you what you're worth. There's multiple parts included in the agreement. You care about them. You love working with them. Like when I talk to people about like, how do you land a dream client?
Like they literally check every box that I would've recommended that you have. Yeah. Um, and how does that start to shift how you're looking at other clients and other opportunities?
Yeah, it's kind of like I get to pick and choose now, whereas maybe like a year and a half ago it was like, I'll take whatever job I can get, but now.
A, I'm, I'm more like well known in like the design and creative community, so mm-hmm. It's, it's a little bit different. Like, people will hire me for me, not just because they need a designer or an illustrator. Um, which is great. It's also really exciting. Um, yeah. Um, I've definitely gotten more selective now if something doesn't resonate with me.
Um, just like. Or if it doesn't feel good or it doesn't feel fun or exciting, I'll, I'll turn it down. Which like, in the past I wasn't able to do that from a financial standpoint, from an emotional standpoint. I was like, but oh my God, I'm trying to build this career. Like, how am I gonna turn down a client?
That's crazy. That doesn't make sense. But it's like, you can work with 10 clients that pay you a hundred dollars, or you can work with one client that pays you a hundred thousand dollars and then you know, it, it, it doesn't just, even out, it's like the, it's exponential because you're also doing something that you love.
Um, so yeah, that's, that's kind of how it's manifested in my career now. And like, um,
there's landing a dream client, there's now knowing that that's a new benchmark. Yeah. And what are other benchmarks that you've started setting, you know, for yourself? Like how many hours you work or what days you work?
Like what else, what other boundaries are being built as your business grows?
Yeah. Um. Definitely the days that I work. Um, once in a while, I still work on weekends if I'm like taking on a lot of work and there's a lot of deadlines, but generally I'm just, I'm out of office on weekends. I need, I need to rest and like, because I'm a human being and in the past it would be like working eight days a week, you know, so that's, you know, that's one thing.
Um, I also won't charge like less than a certain amount because I'm like, I need to have X amount of money. On X amount of days in order to be X amount of fulfilled financially. Um, and that's that on that like, you know mm-hmm. There's, I, you've probably seen the, the meme of like the, the artist singing, like it takes it long 'cause it.
Um, it takes me fucking hours and it's like, yes, it costs that much because it takes me fucking hours, but also because I said so. Mm-hmm. You know, it's like I, I've built this career for myself and around myself to the point where I don't have to work with every single person and I don't necessarily want to work with every single person and I charge a premium for my skills, um, and how I can get my clients from point A to point B.
Did you, do you come from a creative and entrepreneurial family and would 8-year-old you be like, of course, is what you would've been doing?
Um, yeah, I think so. I come from an ENT entrepreneurial family. Um, myself and two of my siblings run their own businesses. My dad has always worked for himself. Um, a lot of people in my family have always worked for themselves.
Not always in the creative field. My mom was a graphic designer before I was born, um, but like before computers. And I'm like, I would never do that. That's, that's crazy. That's, that's absurd. So like, kudos to her for, for trying to make that happen because that's, that, yeah. Me thinking about, I remember her like cutting the pieces and, and placing them together and I was like, you can just click, you know.
Um. Yeah, looking, looking back, I think if 8-year-old me saw me now would be very proud, very excited, and just like, yeah, just hell. Excited.
And how does it work? You know, you got, uh, married recently. How have you balanced, you know, living with your partner and him having a more traditional job and you having a very untraditional, you know, work hours, work schedule and process.
How do you guys balance that? So. You get time for each other, you know, individual space and yeah, you feel like you're actually in a relationship, not just roommates.
So it's actually really hard. Um, this, this 2020 pandemic year taught me like, you know, we always hear like relationships are work, but like once you're stuck inside with somebody for a year and a half, you're like, oh, this is what they meant.
Um, thankfully he, he's working full time in the office now, so we have like those work life balance boundaries. Mm-hmm. Um, not every evening, but most evenings once he gets home, that's kind of like when I shut down. My work. Um, sometimes I end up working a little bit later, but again, that depends on like, just what's going on in my work life.
There's just like a ton of projects, a ton of deadlines, all of that. Um, yeah, I mean definitely the pandemic was definitely trying on every single person. I don't think it's necessarily natural for us to have been that on top of each other. Um, for that amount of time without leaving the house,
do you think that being in New York City and in Brooklyn gives you an advantage?
As a designer?
I really used to think yes, but most, if not all of my clients are outside of New York. Mm-hmm. I actually. I'm trying to think if I have any clients in New York. Oh yeah. The American Foundation for Suicide Prevention happens to be in New York, but I think they found me because of Instagram, like algorithms or searching, but not necessarily in Brooklyn.
I can ask them. Um, yeah. Yeah. So, no, I used to think like New York, Brooklyn, it's so designy and trendy and whatever, and like all of those things. Yes, for sure. Um, but for like the height of my career, I've been stuck inside anyway. Mm-hmm. So, you know, I don't know. I, I, I would say it doesn't really matter where you are.
You can be successful anywhere.
Well, we ask everyone when they hear the words powerful and ladies. How do they define those words individually? And do they mean anything different when they're combined?
Um, I think when they're combined they're like descriptive of each other, you know? So like they have that relationship, but also similarly, like, I think ladies, women are extremely powerful beings and creatures.
Um, and when I think power, I don't really think like. The typical, like, I'm, I'm so powerful and I'm reigning over a nation and whatever. Like, I don't know. For me that doesn't do it. It's more of like the power to make changes, um, like in like your small bubble and like hopefully that spreads positive changes and, um.
Power within yourself to just like be happy because like it's actually not that easy to just be happy. Oh, maybe for some people it is. I don't know. But from my experience, it's not that simple. It's just like, just do whatever you want. Just be happy. Just like be this, like it's not, there is a lot of power and strength that comes in, uh, from that.
And part of what I think is so fascinating about you as well is that you care so much, right? You care about what's happening in the world. You care about, um, how people are being treated and respected. Um, it's really hard for a lot of people who are so empathetic to see what's happening in the world in the past, even just two years, and feel like, what do we do?
You know, how do you, how do you process those feelings yourself and, and what actions, how do you channel all that energy? 'cause you are, you're a force, right? Anyone who gets to spend time with you, they're like, okay, like, what do we do with all this energy that is just like, where do we direct it? So, you know, how, how do you process it?
And then how do you, as you kind of said, like put it back out into your community.
Yeah. So. I remember you and I had a conversation not too long ago, like one of our sessions, and I was just crying the whole time and I'm like, I can't handle what's going on in the world. There's so much hate, it's just like, what the fuck?
And I asked my mom this recently and I was like, was the world always this bad or am I just an adult now? And she was like, no, it was always this bad. And I was like. Kind of gives me hope that like we're on like an even keel of badness and not like going on a downward spiral, which is like, it's like pessimistic optimism.
Um, but it, it is very hard to cope with. I am, I don't know if I'm like, what people recognize as like a full empath, but I'm certainly an extremely empathetic person. So seeing all the pain in the world is, is very hard for me to, to, to cope with. Um. I do cry about it sometimes. I think that's okay. Yeah. I talk to my therapist a lot about it.
Um, and I try to put more positivity out through my work and through women of type. Um, I post a lot of like positive, uplifting messages and I, I stepped away from posting a lot of political things on women of type, um. Because like I was just getting, not a ton, but I was getting like some hate comments and I, I can't take it honestly.
Mm-hmm. Like, I'm just not strong enough to be that person and I don't know if I wanna be strong enough to be that person. Um, but yeah, it's, it's hard to, to cope with it. Mm-hmm.
Yeah. Well, and it's, yeah. Oh, go ahead. And there's just been so many conversations I've been a part of recently of. Especially, you know, women and girls in Afghanistan or Yeah.
You know, that's the one that's getting the most attention right now, but when we look, there's women and girls all over the world who need help. Yeah. Even in our own communities.
Yeah.
And you know, we've been partners with women for men.org since the beginning, since before we existed as a, an official LLC and.
Part of it's been because they're doing the work like this. We share so many values and, and how we mix things. And I'm glad that they have people on the ground who can do this. And I love that they've been incorporating, educating and including men in what they're doing. 'cause you know, we can't, we can't just have half the population changing.
Right. Not the other half. Um, but it, it does get overwhelming. Um, but to your point of creating positive messaging, like that's why I do this. Like it's, I don't know if it makes it better. I don't think it makes it better to fight against whatever side it is that you don't like. So it's like how can we keep coming back together?
And
yeah,
I agree with you of getting hope of like seeing past generations, but like my parents were talking about. Like to them, the mask, wearing a mask or not wearing a mask is very similar to like when they put the seatbelt law into effect. Oh. And nobody wanted to wear seat belts. Interesting. And now, today, like we don't even think about like Right.
Wearing a seatbelt, just
click it
in. Right. You just click it in. Uh, so it's interesting to see how every generation goes through similar steps as we evolve, but I, there's definitely, I think, a feeling that. My generation, like I'm on the border of like millennials and Gen X, I guess whatever that middle section is, all the way to Gen Z.
It's like we are like, no, no, no, no. This is not moving fast enough. And that makes me feel better, that more people are like, this is not moving fast enough. And I, I feel hopeful, like I'm, I'm traditionally an optimistic person anyway, but I still feel like I see. I see more people taking actions than not, you know, here in California, definitely.
Yeah. Mm-hmm. We're going through the, uh, governor recall right now, and everyone's like, what do you think? I'm like, honestly, I think that regardless of what's happening wrong or right in this state, and there's a ton that is not going the way it should be for how powerful California is in all sorts of ways.
And it's like just moving the blame around. It's like, if you want something to change, go do it. Right? Like we keep trying to pass the buck and I'm like, that's not how it works. Like a democracy is not like I hired you, you handle it. Bye. Right. Yeah. You know, it's like, you know, we, I was even having a conversation with a friend yesterday about littering.
And they're like, there are certain places you would never dare litter. Like you just pick up your own shit.
And yeah, I don't, I once, I dumped a guy once, 'cause I saw him littering and I'm like, are you fucking kidding? Like, are you joking?
Yeah. Like what? No, no, no, no, no. And I know it's exhausting to hold ourselves to the standards that we want to see in the world, but like we have to, like, it has to start with us like.
We, you know, there's so much we can do, as you mentioned earlier about like, it, it starts at home. It starts at like how we're taking care of ourselves, how we take care of the people we care about. If we can't take care of the people we care about, how are we ever gonna take care of people that we don't even know exist?
Yeah, that's true. That is definitely true. And I, I like what you said where like, you know, you're optimistic and you're seeing that like younger generations, our generations are, are kind of pushing for like, go faster. Go faster. So. I think, I think there's some optimism there, but like, you know, like I called it before, it's like pessimistic optimism where I'm like, this still sucks, but maybe just a little less than before.
Yeah, yeah. You know, just, just like a drop less.
Well, I know for me it's so important to surround myself with women who I admire and who are up to something and doing what they love. How have women impacted your life and how have they supported you in getting to where you are today?
Well, I think like most of my friends are women and they're all pretty awesome.
Um, so I've been really lucky to have some phenomenal friends that are so supportive. Um. And they're always just like shouting me out, like, and, and putting my work out there and talking about me and my work, and they're like, oh, I referred you to this person. I'm like, that's not what I do, but oh my God, thank you so much.
You know? Um, yeah. My support system has been really, really great. I've, I've been so privileged in that way to have people that love and support me in my work.
And when you're looking for, to inspiration, you know, what are you doing to say on trends and to, to keep your creativity muse going? Are there books, podcasts?
Do you take trips? Like what do you do to, to. Be at your best and to stay creative.
So one of the things that I do to like get in my creative mindset is binge. SVU. Um, there's just something about it that like gets me in the zone. I don't know, like I'm not even necessarily watching, it's just kind of like on and I'm there and like I have my iPad and I'm like starting to sketch.
So like that's just like a little thing that I do that gets me in the zone when I'm having like a creative block. And it works almost every single time. It's. It's kind of insane. Um, it's a great trick for myself. Uh, I used to travel a lot pre pandemic, and that was extremely inspiring, but obviously now it's a little bit different.
So I've been taking some smaller road trips and I love antiquing. I love antiquing, and I get so inspired seeing like, just like old toys and old things, and then like the lettering on books and old cans, like, oh, I love that.
Really lights me up. When you go anti, do you find yourself filling the car back or are you more like, I'm gonna browse and take photos?
A
little bit of both. There have been times where it was like, I don't think we have enough room for all of this. Like, we have to drive back. What are we doing? And then there are times where it's like, okay, I really need to hold myself back. So like I'm just gonna take pictures of things. Um, yeah, a little bit of this, a little bit of that.
But like if there's something that like, I really like fall in love with, I'm like. Take all my money. I
need
it.
I know I haven't been to New York in so long. I really am excited to get back soon. I keep thinking it's gonna be like next month and then restrictions keep hanging on and I'm like, no. Like we have to change it.
'cause there's something traveling to me is the, I don't know, it's like reading books and traveling are like the two things I don't think I can live without. And you know, after people of course, but. It's coffee. It's been, and it's been hard, like there's plenty of books to read during quarantine, but not being able to travel and just feel the different energy of places.
The, there's truly a rhythm and a smell and the, even like science and colors like are just different. Like, you know, if you're in New York City. Yeah. Like you, you, you can't smell. The smell
are really not great. But, but yeah. You know, if you're in New York, I mean, it's loud. It's, it's weird because people that aren't from here or don't live here have such a different perspective.
I would say even people that aren't from here, but have lived here have a very different perspective because like I would say New York is extremely romanticized. Mm-hmm. But like for good reason too. I mean, I would agree that it's the best city in the world. Um, no offense to everyone else that thinks their city is better, it's just not.
Um, but yeah, living here my whole life, it's kind of like a little bit over. Like I just, I maybe I can use some peace and quiet. Maybe I can use like, you know, not waking up at 3:00 AM with like a motorcycle going by my window. Um, yeah, I can do without the smell, stuff like that, but. I do have like those touristy days where I'm like, wow, New York.
I made it a big apple.
Yes. And plus you have the advantage of having your family there too, right? You, you're born and raised. Yeah, I was born
and raised here. Mm-hmm. My parents still live here. My parents live like probably 20 minute drive from
me.
Yeah. Mm-hmm.
I think that makes such a difference, right?
Because if you live in an amazing place and your family's there. You see it in all these different levels, you are like, yeah, we, we used to go to New York as kids 'cause my parents are from New Jersey. And when we would go into the city, it was like, Ooh. Right. And you could see a city at different ages.
It's so, yeah, it's just different, you know? And, and I remember everything fe everything in New York still feels huge as an adult, but as a kid it's like, oh, it's for sure what it still is.
I mean, I don't even go into Manhattan that often, but like when I do, I'm just like, these buildings are really big.
They're massive. What, like, you know, the skyline doesn't get old either. Mm-hmm. Um, I can kind of see it if I like, peek my head out my apartment window and like turn my neck a bit and it's, it is beautiful every time. And I think like we have so many different neighborhoods that all have like their own feel and all like vibe to them.
Um. So yeah. Okay, fine. I guess New York is inspiring. Fine. You got me.
When you think back on the journey that you've had, and you look at some key moments where you're like, this is what my life has pivoted. When have that those moments be, and what triggered them?
Okay, so like one of them that comes to mind immediately is.
Um, I, I lived in South Florida for two years. It was really nice. It was like I, I was working but it was almost like I went into like early retirement 'cause I was living in Boca. Um, but I had like a really nice place and it was so cheap. 'cause it's Florida and I was in the sun all the time, which I thrive in.
And I made some really amazing friends and some shit happened and I had to move back to New York and I had to move back in with my parents. And I was like, I've been living on my own for like three or four years. To something like that at the time. So like, that was a huge setback for me, and it was like kind of devastating.
Mm-hmm. And I was just like, okay, this sucks. I need to save up enough money, make enough money to like get a place, figure it out. But at the same time, I had just decided like that, that's when I decided like I am having a creative career. I don't care. I don't care what it is. I, I need to be creative. I can't be bouncing around from like.
For me, they were bullshit jobs because I didn't care about them. I wasn't passionate about them. So like bouncing around from one bullshit job to another and like that's what they were. They were jobs, they were not career paths in any capacity. And for some people they probably are and, and would be.
Yeah. Um. But I really, I'm, I'm a very decisive person, so like, once I make a decision, it's not like, okay, like maybe I'm gonna try this. It's like, no, that's it. This is what's happening. It's, it's not an option anymore. It's not a question. This is just it. So like, I remember going through like that process of realizing and deciding like, I'm gonna have a creative career, and it was really exciting and also really hard and scary at the same time.
Yeah.
I, you know, a lot of people ask like, how do you just start? And I think that's the first step. You just decide. Yeah. You just decide. Yeah. So when you decided, did you know how to make it happen? Did you know what it would look like? Did you know Not at all, how you get
there? No. A big thing for me was that I stopped, so at the time I was selling menswear and eBay and I stopped telling people that I, I was still doing it a little bit on the side, but I just started telling people like, oh, what do you do?
Oh, I'm an artist. That's it. Like I, I didn't allow like other options to like seep into my reality. I was just like, this is what I am, this is who I am, this is what I do. And I was very poor for a very long time. I remember my first year doing that. I made like less than $20,000. Mm-hmm. And I lived in this really scary apartment, um, with two other people, and it was dirty and gross.
And one of the roommates, like I had, I, there, there, there was something like she had her, her own issues and like, I'm not gonna judge her for them, but like, she was very scary. Like she would like get in my face and try to fight with me. She would like, if I would leave my room, she would throw garbage at me and like that's, yeah, it was, it was very scary.
It was, it was just a scary environment for me to live in. Like at night, I would lock my bedroom door. When I left, I had a key, I would lock my bedroom door, which like I had roommates before that and after that, and I never did that because I trusted that they wouldn't try to hurt me. Mm-hmm. Um, but that was not the situation here.
That's also like a very New York thing. I feel like. A lot of people that either have moved to New York or live in New York have a story about a roommate that was probably trying to get violent with them. But anyway, yeah, to my point, it wasn't easy. Um, I didn't show any of that part of my life to the world except for like, you know, my close friends and my husband, who's my boyfriend at the time, like they all knew the situation.
But I think from like an outside perspective, it seemed like, oh, she's just like being artsy and like random, you know? But no, it was, it was
terrifying and I hated it. Yeah. Ar artsy and random often means broke and figuring it out.
Yeah, that's exactly what it is.
Yeah. Like I remember when, um, like the Sperry top cider, like started look, came back in like, like the early earliest glimpses of hipster coming in.
Yeah. And they're like, why are these, like, why is everyone starting wearing these? I'm like, they got them at a thrift store. Like, yeah. This is not, like, they're not buying them new. Like, get out here.
Yeah, that's true. Yeah, for sure. Um, yeah, it was, it was like that.
So where do you get the confidence to declare it and then be like, all right, fuck it.
We're gonna figure this out. Like, how do you have the confidence to just go like one step at a time? Like when you decide I'm going this way, like, what's the next thing that you do?
Um, it's a good question. I don't, I don't really know. I, I kind of just. Do it. Like, I don't know. You have, we have Google, Google's a really great source to really like, figure out anything.
I think I also have like a very false sense of, um, confidence because like my parents were always like, you're amazing. You're the best. You could do whatever you want. And I'm like, are you sure? I can't do math? Like, but they, they instilled that in me and I'm extremely grateful because that false sense of confidence turned into a very real sense of confidence that exists in my life that it's just like.
Like you said before, I'm, I'm like a force and when I wanna do something and when I decide to do something, whether or not it's that day or that year, like it does happen.
Mm-hmm. No, because you know, so many people are stuck in that place of I want something else, but I don't know how to get there. So I guess it's not for me, and I think people miss that.
It sounds totally insane when we say yes to things the first time. Like it's almost like having to go back to being a kid and being like, I'm gonna be an astronaut. Like it's, that's how much thought often goes into these things. Mm-hmm. And we have no idea what the next steps are, but you just be like, all right, I don't know.
Let's, what can I figure out today? Yeah. It's, it's a lot. You know, people ask me if I have like a three and five year plan. And I'm like, yes. And it's like five bullet points. Like I, it would not pass. Yeah. Uh, you know, an academic stuff test of like, is this a plan? Because it's more of like, I know where I am and I know where I wanna end up, but how we get there between, it's like, I don't know, like it'll keep changing, but I know how I wanna feel when I get there.
I think a lot of people get really scared about like the not knowing how to get there and like, you really need to just let go of how you're gonna get there and just trust that it's gonna happen and like, that's scary. A lot of people fail, but I'm a very big advocate on saying it's not failure unless you give up.
Yes. And I think that's really true because you could just be redirected in a completely different way. Like mm-hmm. I took a digital marketing class so I can sell my paintings, and then I was like, eh, gonna switch. I'm actually a graphic designer now. Um, and that's not what I had intended on doing. In fact, when I did go to college.
Which I didn't graduate from community college. I, my first semester I took a graphic design class and I freaked out because I didn't know how to use any of the computers or the Adobe products. I cried in class and I left. I was a big baby. I was a big fucking baby, and I left. Um. But now I'm just like, what a joke.
Like I could do this in my sleep.
So how did you end up learning? Did you go back to class or did you just say, fuck it, I'm gonna teach myself? No, I,
I taught myself. Mm-hmm. I taught myself. Um, and I, I don't, I don't know everything, but I do things in ways that work for me that are efficient for me. Mm-hmm.
And people like it and brands like it. I keep getting hired. So, I mean, it's working. Yeah,
well, there's always, even people who go to school, some of the smartest people I know who have the most degrees, are the most stuck in like being afraid of what they don't know. They don't know, like they're, they're not qualified.
And I'm like, you have 500 degrees. What do you think you're not qualified for? Whereas other people who have figured it out on their own, they're much more likely to be like, I can do it. Because you know, you can figure it out.
Yeah. Yeah. I think it's that realization that like you don't need a clear path to get from point A to point B.
Like you might hit some brush, you might hit some tall grass, a river, whatever, but like you can just kind of manufacture the ways to get around those obstacles. Yeah. You know, obviously not everything, like, we're not, we're not, we are magic, but in, in a different way, you know, but like, I, I don't know. Yeah, there's, there's ways to get from point A to point B without having a clear path.
Mm-hmm. Uh, so we talked a little bit earlier about, you know, what frustrates or upsets you in the world, but what are things that frustrate you in like that you just. Always are like, Nope, we're fixing that. Nope, we're changing that. Like, in your own life or what you interact with. Um,
Ooh, I don't know. Or like another pretty, I think I'm a pretty easygoing person that I'm just kinda like me, whatever.
Like this doesn't bother me. Um, I will change the channel if sports are on. Don't, don't like that. Um, don't like sports, don't like math, but I mean, I don't know otherwise.
Or maybe another. Do you, do you have
like another example of like in terms of what?
Yeah. Or like what are things you, you realized that you do, like, you're like, like what would your husband say?
Like, oh no, you do this all the time. Like, is it like tidy things up? Is it movie things? Is it re hanging in a picture? Oh, I'm really messy.
I'm a, I'm an extremely messy person and I don't like cleaning. And the cleaning drains me. I don't like it. One thi I like when things are clean, but I don't like doing the act of it.
So. That's definitely something that I should work on, but it's also like, I don't want to work on it because I don't want, I don't wanna be that person that's always cleaning. You can, my previous roommate, not the one that I had all those problems with, but one of my best friends, she'll tell you I'm, I'm a very messy person.
Um, but I found the solution. I can make more money during a certain amount of. During a certain period of time if somebody else is cleaning for me. Mm-hmm. So it's like, yes, it's a privilege and it could be expensive to hire a cleaning person, but like during those five to eight hours that that person is cleaning, I can make more money in my business and I'm able to pay them a, like a normal wage for it.
Um. So that's my solution. Just delegate the task out to people that mm-hmm. Want to do it or have the means to do it. I don't have the means to be a clean, cleaner, a neater person. I'm not dirty. I'm just not, I'm not tidy.
Yeah. No. And that's what I, you know, people get so nervous about delegating and you gave the exact example.
I would, yeah. If, if you can delegate it to somebody for half of what you can make in that same hour, I don't care what it is, delegate it. We get so hung up on having to do everything ourselves, and that is a lie. Such a lie that we have been told.
Yeah, I do have an issue of like letting go of that power within my business, like mm-hmm.
I think I'm almost at the point where I probably need to hire an assistant, like either somebody that can help me out with my work or kind of like take on certain tasks. For me. Um, but I'm just, I'm too, I'm too afraid. I'm not there yet. So like, I don't feel that pressure. Um, but there, there are some weeks where I'm like, shit.
Like, mm-hmm. I think I have to hire somebody. And like I'm, I'm just like not ready to like hand over that trust because like, this, this is my baby other than my dog. This is the only other baby that I, that I have and wanna have. And I, I have to take care of it.
I have a, another client who I'm like, you need an assistant.
And she's like, why? I'm like, because think about all the hours you're spending and they have a physical office with employees. I'm like, you're calling about the electricity you're calling when the air conditioner breaks. You're making sure there's toilet paper in the bathroom, let alone 150 other things.
And I'm like, why? Like just 'cause you can do it doesn't mean you should at all.
Yeah. I think I would really like to have like an in, I mean, I think everybody would like to have an in-person personal assistant. Um, and that it would be easier for me because it would be like, Hey, can you go grocery shopping for me?
Hey, can you go get my coffee? Hey, can you do this? You know, and like writing an email, um, just like learning my tone of voice, so like mm-hmm. Writing an email, making phone calls for me, like calling the cable company to make sure that like my WiFi's working, all of that, like mm-hmm. I can handle that. But I think that if I'm gonna be paying somebody as an assistant, it would need to be like, probably working with me and like.
I don't know. Just the idea of that is terrifying.
Yeah, so scary. I think the, the boss, the most boss comment I've heard about delegating on this podcast came from Casey Wilson, the actress and writer, and she said that when she was first coming up through Hollywood, she was. Uh, a bunch of personal assistants and she never did like any of the work.
She always had another personal assistant that she hired who was actually everything was delegated to so she could go and auditions, and it cracked me up that she's like, I'm just gonna work this whole system. And whether people know or not, we'll figure that out later. But she basically had her own like personal assistant side hustle happening that she was just.
The middleman and I think it's really interesting to like have that perspective. Like, no, I have to go over here and I have to earn money, so how can I make it all work right now? Yeah.
Yeah. I. I definitely agree. Um, we'll, we'll see if I ever allow that trust to, I'm sure it will, because I'll get to a point where like, I really won't have a choice.
It's like either stay where you are and don't grow or hire somebody and then grow exponentially like it's gonna get to that point. I'm kind of thankful that I'm not there yet because I kind of like need to gather myself. But I don't know, probably next year this time I would've, I'll probably have already hired an assistant.
I love it.
Yeah.
Well, so we ask everyone on the podcast where they put themselves in the powerful lady scale, zero being average, everyday human, and 10 being the most powerful lady you can imagine. Where would you put yourself today and where would you put yourself on average?
Is it like really narcissistic of me?
If I say 10 and 10?
No, I've had people say 15.
Oh, shit. Okay. Then 20.
What makes you pick 20? I don't know, because I. Maybe not 20. I, you know, I'm not, I'm not trying to like, go off the rails and like become like a, a crazy dictator with my power. But I, I don't know, I, I feel power within me. I feel power to help myself and help the people around me and through that hopefully, and, and eventually help the world to be a better place.
Mm-hmm. Um. Yeah, I think just like being powerful within yourself is actually so powerful because it gives you the opportunity to inspire people around you. Whether or not you know it, like it doesn't matter if you know it or not, it's, it's very, very likely still happening.
Mm-hmm. I love that. So I know that we have a lot of exciting things coming up for you.
I know you and I are working on co-hosting an event that'll come up at the end of the year, um, or before the end of the year. Um, what else is going on with, uh, for you and how can people follow you, find you and reach out to either Connect, do PR, or work with you?
Yeah. So first of all, please reach out to me for PR and work opportunities.
I'm trying to up my PR game. Um. I am here to be featured in publications and to create, uh, work for publications. Um, so yeah, definitely hit me up there. My email address is the Chick of All trade@gmail.com. My website is chick of all trade.com, and you can find me on Instagram at Chick of All Trade. Um, currently I am working on a couple of social media pieces for Hulu for a show that's coming out.
Um, I can't talk too much about it, but I'm very excited about it. And like we mentioned before, I'm working with the American Foundation for Suicide Prevention and I. Created all of the cover art for their, the cover art and the key art for their campaign. They did an interview with me. I'm gonna be on some speaking panels, so I'm just like so beyond stoked to be working on that.
Um, also the thing for Hulu is surrounded around mental health too. So it's really just like a really a perfect puzzle piece to go into the, the picture of my life and career.
Well, please make sure that you tag me and powerful ladies and all those things. 'cause then we can reshare and people know what you're talking about so they can get excited and Yeah.
And see the reveal. Um, you know, as we're wrapping up today, for everyone listening, whether they're trying to get into a career, creative career path or not, like for people who are just looking for what's next in their life, what do you want them to know? What do you want them to remember?
I want 'em to know that it's scary, but like, who cares?
Like just do it anyway. Like it, it doesn't matter that it's scary. One of my, I don't know who it is, you guys can Google it, but like one of my favorite quotes is feel the fear and do it anyway. Mm-hmm. It's fine for it to be scary. It would probably be weird if you weren't afraid to like make a huge jump and change in your life, in your career.
Like it's very normal, but like just do it anyway. Like think of the worst case scenario and then realize it's probably not even gonna be close to that.
I love that. And feel the fear and do it anyway as a book. Um, it's a book title. Oh, it is as well? Yes. Oh, okay. I should read
it. Yeah.
And for you and anyone else who wants to get it, um, it'll be in the library.
So if you go to learn.care deputy.com and you can get my whole library for free, but that book's in there. Oh, that is so good to know. I, I can't believe I didn't know it was a book. No, it's like one of the original self-help books. Yeah. Is, it's classic. Funny. I say
it all the time, like just talking to friends, talking to myself, talking to my husband.
I'm like, who cares? Just do it anyway. Like who, you know. Yeah.
Well, we, we have to, right? Because our, our, yeah. Our brains are, are built so well to protect us and for our survival.
Yeah. Um,
but sometimes we have to tell our brain. Thank you. I heard you we're doing it anyway. Buckle up. Mm-hmm.
Yep. Exactly. Yeah.
Well, it's been such a pleasure to hang out with you this morning. Thank you so much being a yes to me and the powerful ladies, and I hope I get to have you on again. Yeah, I would love to. Thank you for having me.
Thank you for listening to today's episode. All the links to connect with Jess are in our show notes@thepowerfulladies.com slash podcast. Want more powerful ladies, come join us on Instagram at Powerful Ladies. We can also find some free downloads to start being powerful today. Subscribe to this podcast and help us connect with more listeners like you by leaving us a five star rating and review.
If you're looking to connect directly with me, visit kara duffy.com or come follow me on Instagram at Kara Duffy. I like to thank our composer, audio engineer and magician Jordan Duffy. Without her, this wouldn't be possible. You can follow her on Instagram at Jordan K. Duffy. We'll be back next week with a brand new episode.
Until then, I hope you're taking on being powerful in your life. Go be awesome and up to something you love.
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Instagram: @chickofalltrade @womenoftype
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Email: thechickofalltrade@gmail.com
Created and hosted by Kara Duffy
Audio Engineering & Editing by Jordan Duffy
Production by Amanda Kass
Graphic design by Anna Olinova
Music by Joakim Karud
