#26 - Better Together with Lisa Congdon and Clay Walsh

What happens when you go into creative entrepreneurship with your significant other? And what about when you've established a business as a creative solopreneur and then ask your significant other to quit a dreamy job and work with you? Today's episode gives us answers to these questions and more.

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Kathleen Shannon: 0:04

Get your business together, get yourself into what you do and see it through.

Emily Thompson: 0:10

Because being boss is hard, winning work and life is messy. Making your dream job of your own isn't easy.

Kathleen Shannon: 0:18

But getting paid for it, becoming known for it. And finding purpose in it is so doable

Emily Thompson: 0:25

if you do the work, being Vox, a podcast for greed of entrepreneurs from Emily Thompson and Kathleen Shannon. Welcome to Episode 26. With our guest, Lisa Congdon and clay Walsh, this episode is brought to you by fresh books cloud accounting.

Kathleen Shannon: 0:47

Alright bosses, if you all don't know Lisa Congdon, you're in for a treat today. Lisa is a full time working artists. You may have seen her work in Martha Stewart Living the land of nod. And even at the contemporary Jewish Museum and Bedford gallery. Lisa has written five books including art Inc, the Essential Guide to building your career as an artist, and whatever you are be a good one. She also writes a daily blog about her work life and inspiration. Now, if you're already a fan of Lisa Condon, you might know her wife, Clay Walsh, we have clay on our call today too, because she just left her Boss Lady job working as the Director of Marketing at California College of the Arts. She made the scary leap to join Lisa as a head of marketing and operations for at least a Condon art and illustration. So what this means is today, we're going to be talking about being an artist for living, quitting your day job and what it's like to work as a couple, including how to set up goals and expectations for running a business together, while still maintaining a healthy life outside of work. So Lisa clay Hello, welcome to being boss. Thanks for joining us.

Unknown: 1:58

Thanks for having us. Thanks so much.

Kathleen Shannon: 2:00

All right, I want to start by talking to you, Lisa, a little bit about becoming an artist and doing it as a career. Tell us a little bit about yourself.

Unknown: 2:11

Well, um, when I was 31, I think maybe I was 32 I can't remember exactly. Um, I was a project manager at a nonprofit organization. I started kind of at the associate director level had worked in this organization for many years already. And I got an itch to be more creative. And my brother at the time, he's two years older than I am, he was also living in San Francisco. And we decided to take an art class together, he needed to fulfill a requirement for a program, he was in an elective requirement. And he didn't want to take the class by himself. So I took it with him, I had no idea none at the time that this would put set me on the trajectory that I'm on, or that I've been on for the last 16 years. But I went to this class with him, thoroughly enjoyed myself. And it wasn't even like at that class, I was like, I'm going to be an artist, you know, um, but I went home and the class ended and I didn't want to stop. And so I started filling my time outside of work with painting and drawing and collage. Now, I am been doing this for 16 years. So if you look at the painting and collage and drawing that I do now, it's you know, rather sophisticated, but at the time, I had no idea what I was doing. I was a total beginner, my work was really terrible, actually. But I loved it. And I had fun. And that will that's what was important. And for me, it was just a great outlet outside of work. And so I did that for a few years just randomly took art classes here. And there just made a lot of stuff by myself at my kitchen table. I was single for many years at this time. And so it was like how I entertained myself after work and on the weekends when I didn't have anything else to do. And then in around 2005, four or five in there. So I've been at it for two or three years, I started a blog. It's a different blog than I have now. And I joined flicker, and I met all these other people who were, you know, making stuff and had, you know, where the DIY movement was kind of starting around that time on the internet. And I met a lot of other artists and I was also sewing a lot and met other people who were sewing and quilting. And so I just sort of became immersed in this world, but I wasn't really selling anything at first and then I'm slowly President Trump 2005 2006 I started getting emails and comments. Like I would love to buy that thing that you're making, because a lot of what I was posting on my blog and on Flickr were the things that I was Making and But meanwhile, you still have a day job, right? Oh, meanwhile, I totally had a day job. This was not anything. Yeah, like, this was just a hobby for me. Okay. And, um, so people but people started asking me to buy stuff and like my work was really inexpensive at the time and there's no way I could have made a live living even if I sold a lot of it. So, um, and I was totally ill prepared to be a full time artist. But I got this idea in my head that if I worked at this for long enough, and in the right way is that I might be able to eventually do this for a living. I wasn't exactly sure how. And then by 2007, I was I had opened an Etsy shop and I had like my first two illustration jobs, which were really small and paid like $200. But, you know, I took them, and I left my job. Eventually, in 2007, I opened a store for a few years with a friend of mine. So that was a way for me to be self employed, but not rely solely on my art practice to sustain my life in San Francisco, which, let's face it was, is and even then was an expensive place to live. So that combination of things for a few years was great. And while I owned the store and left my job, I continued to work on my portfolio and figure out different income streams for myself, put my work into the world, take advantage of all the new social media. And by 2010, I realized that I was making full time I was making enough to support myself full time. Barely but enough. And so my friend Rena and I who owns the store together, we decided to sell the store. And it was that Rena Tom, yeah, okay, yeah, no that Yeah, Rena, and I actually the way we met is Reena used to own the store rare device in New York. And I had a show there. And that's how we became friends. And then she moved to San Francisco and we opened her device together.

Kathleen Shannon: 7:10

Okay, so Rena Tom, for those of you who don't know, and I think that she's probably most well known right now for make shift, which is her co working collaborative workspace. We should have her on the show.

Emily Thompson: 7:23

I agree. I love Rena,

Unknown: 7:25

just you totally should. She's serious boss. Yeah, and no, yeah, call each other boss. Yeah, actually, that's true. Like when we start, we opened the store together. It was the first time Well, she had been self employed for a while, but I had never been self employed. And so I needed to call someone boss. Someone else and then she decided to call me boss back. But anyway, yeah, we on the store together. Meanwhile, it was great because I could, I was learning a lot from Rena, who knew a lot about the like wholesale retail part of, you know, entrepreneurship, or creative entrepreneurship as an income stream. So I learned a lot from her. And I learned how to own a store, which was a great perspective for me to have. Even though I realized after a while, I didn't want to do it anymore. I really wanted to just be an artist full time. So we closed the store, she went on to open to make sure societies one in Brooklyn, one in San Francisco, and then one in Brooklyn. And I ended up just, you know, kind of launching my full time art career.

Kathleen Shannon: 8:26

Okay, I have a couple of questions. I want to jump in and ask like a web plane, did you feel like an artist? And at what point did you feel like an entrepreneur? Well, I probably

Unknown: 8:36

felt like an entrepreneur before I felt like an artist. Like, I know that sounds really weird. I've written a book, a business book called Art Inc, about making a living as an artist. So I felt like an imposter a lot in the beginning, because I didn't go through the formal channels to become an artist, I sort of like, It all happened by accident, my except my success. You know, I just felt really lucky the whole time. Like, you know, and also that I was sort of, at this party that, you know, that I that I wasn't invited to, and that I was gonna get kicked out eventually, for not being, you know, legitimate or whatever. So, I realize now that was ridiculous, but that's the way I felt. And I understand now that that's how a lot of people feel, especially people who are self taught or who enter the art world, or the crafting world or the being a boss world later in life, like I did. So. I definitely like being an artist. I felt more, you know, more intimidated to call myself that and proclaim that about myself not being an entrepreneur. What didn't feel as hard to me, I think because I was a boss at my former job. Like I managed people. I worked my way up in this nonprofit organization. I had a lot of I had some success. And so I felt it felt easier for me to just say, Oh, I'm a I'm a small business owner, I own a store. Um, I sell things we've been it was for me to, you know, be like I'm an artist because somehow that felt more pretentious or more like I should I, you know that I wasn't really a real artist.

Kathleen Shannon: 10:14

So did you have a turning point, though, where you did feel like a real artist, or that you could at least claim that title was at that first illustration job, or was it,

Unknown: 10:23

it was actually way after that, I mean, I struggled with imposter syndrome, you know, which is, for those of you who are maybe listening who don't really know what I'm referring to, it's really just this feeling that a lot of people have, that they that they somehow don't really belong in whatever sort of entrepreneurial or business endeavor that they're, they're in, and that you think that, you know, everybody else knows what they're doing, everybody else has legitimacy, except you, and that you're sort of faking it, or that other people don't, you know, are judging you in some way. And I felt that way for a long time in the art and illustration world. And, and then I found myself sort of, like, pretty upset about it internally, like, a lot of self judgment. And a lot of stuff that I realized, the more I reflected, was really holding me back in terms of putting my work into the world, or just sort of being a generally happy person. So I literally woke up one day and was like, This is bullshit, you know, I have to own my identity as an artist, I need to like, be this person who, who owns not just this not just being an artist, but like my path to getting there, that just because I didn't go to art school, or I didn't train at risk D or, you know, meanwhile, I had all the same clients, or a lot of the same clients that very well trained, or, you know, people who I thought were real illustrators had, it was only my perception of myself and how I thought other people would perceive me, that was holding me back. And then I realized, no one's even thinking about that you shouldn't be thinking about it either. And, in fact, that a lot of the stuff that I was ashamed of before like that, I didn't start drawing or painting until I was in my 30s. And I was, at that point already in my 40s. were things that I should own and embrace and use to my advantage. And I realize now that all my work experience and all my life experience have actually helped me sort of like fast track my success, because I learned so much about how to be in the world and like how to be a good boss, how to be a good business person, how to work with clients, how to be polite, and professional over email, how to respond quickly how to meet deadlines.

Kathleen Shannon: 12:40

I mean, I did go to art school, and I went, I thought I was going to go down a fine art path, but ended up doing graphic design. And what I found is that no matter how talented you are, if you want to make a career, in anything, being your own boss, talent isn't enough. Like you have to have the systems in place, which I'm also excited to talk to you about. Because one of the things that you said is, how do you prepare to be a full time artist and not being prepared to be a full time artist? So I want to talk a little bit about that. But first, I want to pause and talk about clay and Lisa, how did the two of like, at what point did you two meet?

Unknown: 13:18

We met about almost seven years ago, I'm on an online dating site. And we like we both joined the site, like the same day and met that week. I was not someone that I could picture myself on online dating. I had never done it before. Lisa had before. And I just was not into it. And I had a friend that convinced me that I should and I said fine. And I did it and well, it worked out Yeah. And then we like within a week. Um, we we didn't even ever go on dates with anyone else from the online site. Like we met each other first. And then that so it was kind of like we forget we met online because it happens so fast. People go through months and months and months and months and months or years of like trying people out before they meet the right person or they just give up because they think I didn't have to go through the only person I've ever dated online and the last person Yeah. And then clay at the time was working in like high tech marketing. And I at the time my art career hadn't really I was I owned the store. My art career was sort of like a half time thing that I wanted to be a full time thing, but I was having a hard time getting it off the ground at first. And so she's really seen me like kind of understands my business and what I do pretty intimately even before she was working with me because she sort of met me when I was at that crossroads of like, Am I going to work my ass off to make this happen? Or because I was like in debt and I was you know, I had to borrow money from you? quite a bit. Yeah, and I was really struggling and she was like look you either have To figure this out, or you have to go get a job again, and I was like, No way, am I getting a job again? So I figured it out. And so she sort of seen me along on that path. And then about a year or so we got married two years ago. And then about a year and a half ago. It was like January 1, like the first week of January, that time when you're like, Okay, what is getting? What's this, you're gonna be about or what are our goals? And we talk about that a lot in our life in general, like, what do we want out of life? How can we make that happen, we're very sort of like intention based driven. And I was talking about how I loved the work I was doing. But I was starting to be really overwhelmed by all of the opportunity that I had, I mean, all of the stuff that I worked for was happening, and I was not able to sustain it, I knew that I wouldn't be able to sustain it much longer by myself without completely burning out. And you were burnt out, I was already burnt out at that point. And taking a toll just in general, there was a lot of late nights, and I had a regular full time job. So I could leave my job at the job and come home. And there were really a lot of late nights of, you know, her working late, or I would help with the FCC orders or whatever it is. And I've traveled with her on several business trips and meetings and things like that. So I was pretty involved, but just kind of from a partner standpoint, right? And then we were like, well, what would it be? Like? Let's just brainstorm what would it be like to think about how we, how what, you know, like, what's the what are, first of all, what are potential solutions to this problem that I had that my business was exploding, I could hire somebody, I could hire I could. But I needed somebody at a sort of higher level than an assistant, somebody who could do both administrative stuff, but also strategic stuff and had a lot of expertise. And clay at the time was the Director of Marketing at California College of the Arts, where she had been for six years. And so we started talking about what it would be like for her to join me as my business partner, and helped me manage all of these parts of my business that were taking me away from drawing and painting and creating the artwork. I'm good at those things also. And I like them. But I just didn't have time to do the administrative and strategic and business partnership part of what I do. And also make art, I did have an agent. And that was really helpful at the time. But I needed more. And so we took a year and a half to really think it through, what would it require, maybe would have to leave the Bay Area, because it's really expensive. If we're just going to live off one income, what other sacrifices could we make to make this happen? And then how can we make this like working relationship that right, that is going to make our lives happier and more fulfilled? And yeah, and here we are. Alright, well, so

Kathleen Shannon: 17:57

let's jump into that clay. Did you love your job that you were working out? Like, it doesn't seem like you were miserable? Yeah. So tell us a little bit about that. Like, what was it like going from day job to then making that leap?

Unknown: 18:12

Well, it was not an easy decision. And I put Lisa through a roller coaster. And not to mention, I was sort of on a upward ladder there. at the college, I started working there and oh nine. And by the time I left, I was the director of marketing and had built a team hired an amazing creative team. And I really enjoyed my boss, my boss was hilarious and so supportive, and let me do my thing. And in a way, I was a little entrepreneur in my office and started systems and processes for the department. And the team and I managed this entire internship program of graphic designers too. And it just was really like on paper. The job is is awesome. I mean, it's it's sounds like a sexy job, right? So for a while, it was my dream job. And we lived right down the street from it. And when we lived in the Mission District in San Francisco and I rode my bike there took me five minutes and Lisa joined me for art openings at night. And we just had this really cool thing going where Lisa was doing art during the day and in the art world and I was bringing her to illustration shows and I was meeting students and it was amazing. And it just got to be too much over time the workload increased. We moved to Oakland and my commute turned into a two hour round trip a day. That was huge. Yeah, you don't really love your job as much when you have to commute that far and I was so jealous of of Lisa's. It just that was when I kept saying like you know I work really hard but I also get to make all these choices about how I spend my time when I work when I go on vacation, how I you know and I think clay started to realize lies that being an entrepreneur. While it I mean, I think she saw me work really hard. And that kind of scared her a little bit. At the same time, I think she could see like how my income was increasing every year, like, the success I had was exponential to the amount of work I was doing. Were at her job, she would work really hard. And it wouldn't lead to anything except, you know, so called more work. Yeah, I found that the better the more you do, the more people want your work or want what you do. So So for me, there was a point where I my work was I was doing really well. And we were doing amazing things that I would have to have a keep a low profile, because if I ran into an important faculty member, they'd say, Hey, I saw that video you create, and I really need that too. And if there was no, it would never would end. You know, I couldn't build more or, you know, bring on anyone else. There's a limit. And it wasn't nonprofit college. So So the answer is really that yes, it was a dreamy job. But you know, a broader over. Yeah.

Emily Thompson: 21:04

Welcome to the dark side, like earning potential take time off whenever you want and work whenever you want. It's

Unknown: 21:10

kind of nice. I got to the I really am one of those people that needs to work out. Every day I run, I swim, I go to spin class, I've done triathlons in the past, I just need to do that before work. And so all I could do it after work. I'm not you know, I'm not picky. But I got to the point where the commute was so long that I was getting up at 530 in the morning to go to these boot camp classes. And I was so tired at eight o'clock pm, I've already passed out on the couch. And now we don't get up any earlier, we still fit in our workouts and our workday and having dinner with friends and stuff. So yeah, the life is just so much more, more than I could ask for in terms of the free time. And I'm someone that needs a lot of free time. And I just didn't have that.

Emily Thompson: 21:58

I want to know how it is. So once you took that leap, how that changed, like your relationship. Because obviously you guys go from from having, like, separate lives, basically, to really sort of sharing everything, but like, you know, enjoying it potentially like a whole lot more. So what was that? Like? Yeah, how did it change your relationship?

Unknown: 22:20

Well, we were really proactive in the beginning about setting ourselves up to do this as well as we could we knew that even if we did set ourselves up, we would still falter. But I worked with a business coach for years. Her name is Tiffany Hahn, and she I hadn't been working with her for a few years. So that was earlier in my career. And we actually had alt summit this year, I was the keynote speaker and we went to a lot of sessions together. And at that point, Clay hadn't left her job yet, but she was about to, but we were really thinking about this idea of collaborating and working together. And also that we're married, we're wives, we have this whole other life together, and how can we set ourselves up so that we had boundaries around the right things. And we were operating from the same understanding about how to approach the business and how to work together. And I just got this idea that we should spend have like a retreat with Tiffany, where she kind of helped us figure out, you know, what are our goals? What are the ground rules for working together? Like, how can we communicate respectfully to each other? And when we don't? How can we deal with it? How do we get clear on who's doing what and what our roles are? Like? How can we set ourselves up for success? Not that we still wouldn't be, you know, confronting difficulty. So we did spend a day with Tiffany and we wrote all kinds of commitments to each other, which we're still referring to now. And it was such a valuable day. That I think, if we hadn't done it, we'd be struggling a lot more. And we're still struggling with trying to do exactly what you guys are asking, which is, you know, figure out how how do you work together when when you're also in a relationship? And then how do you stop at the end of the day, and maybe not talk about work? You know, what the best thing is, is in San Francisco, we have this. And we're growing that here in Portland too. But we just moved from the San Francisco Bay area to Portland about almost two months ago. So our community there was full of creatives, and so many of them were couples. And when we had friends from three fish studios who ran their printmaking studio, and they were business partners, and you know, we have friends Betsy and Chuck who run art licensing and branding company together and just to see how they work together, and we really reached out to them and just ask them, you know, how's it going and you know, they're there. There's no right or wrong way. But I think we're being really intentional with this and we're still learning and we talk things out and, you know, some of the rules that we had that, you know, they're not strict, but you know, at the end of the day, let's kind of like, have signals like the laptops close, and I walk the dog and we start dinner and PR comes on, or we have plans. And so it's not like this around the clock thing. Trying to kind of have boundaries, boundaries. And, you know, like, there's ways that you there's a comfort level you have with the person that you're in a relationship with, which leads to sometimes talking to them in ways that you are not proud of five minutes later, but you know, that's what happens, right? I think, you know, with family or that's, and, um, so I have to remember that, you know, um, especially when we're working together, it's really important that, you know, because this has been my business for so long, and I'm bringing this person on, and that who I want to share equal power, but that is easier said than done. And I may speak to her in ways or use certain facial expressions that indicate that I'm, you know, disapproving of some choice she's made, even though I've told her go off and take leadership and ownership of whatever it is gonna take some time for that, but just that I like, I think we both had to have humble humbling moments where like, she'll be like, that was really patronizing the way you just talk to me, you know, and you have to see those things in the moment. And I have to be like, you're right, I am so sorry. I'm going to work on that. So you have to talk about things in the moment, and you have to be willing to work them out. And you have to be willing to say you're sorry, and move on. Because I think just like in a relationship, romantic relationship or work relationship is no different in both parts of our life. We have to we can't carry around resentments or angers we have to get them out in the open and we have to work through them really quickly. So we're working a lot on that.

Kathleen Shannon: 26:52

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Unknown: 28:30

I think it's both because I mean, obviously my brand developed both because of my artwork and also my presence online. So I write a blog, I have an Instagram account. So it's not people see me as a human being and my artwork. My name is attached. I don't have a you know, I'm not Bluebird studios, you know, I Lisa Congdon, art and illustration. So, um, I anna and i have been the face of my brand for a long time I teach I have, you know, all these other things going on. And so clay had to be okay with that. And I am okay. Yeah, yeah, she's totally okay. You have over there. Yeah, she did, because there was no turning back, you know, however, I'm part of the reason that I felt so strongly about having someone like either clay or someone like clay come on to support my business, as opposed to just hiring a, you know, an assistant for however many dollars an hour a week, which in some ways might have been the cheaper option was that I realized that the only way that I was going to grow or scale my business or meet financial goals that I had made for myself, or you know, do projects that I wanted to do was by bringing on another person and the the calculated risk that I took was that paying somebody is much of the income that I bring in paying somebody else to support my business is going to pay for itself like five or 10 fold. clays, all right, I'm already able now to take advantage of opportunities that I wouldn't even had time before to respond to the email. Or were actually seeking out some new business relationships. And that's not something I would have had time to do. The fact that clay is just constantly so responsive to clients and people who expressed an interest in working with me, and sets up all the backend stuff for me. So that all I have to do is get clear, you know, what my art direction is? If it's an illustration job, or what the parameters are, if it's another kind of project, it's great. And so I think, you know, we haven't gotten to the point yet where we can measure really like the impact of clay being on board. I mean, I could measure it, but and I think in a year, we we literally will be able to measure it in dollar signs. And not that that's what it's all about. But we're we're keeping track of our workflow in a way that, you know, Lisa is really organized, and she's done this amazing job for all of these years, by myself, right? But we're able to really keep a log of everything we're working on, along with what's coming in and what's going out. And not to mention just the opportunities that you know, they're broken out. I mean, there's not just, you know, illustration work. I mean, there's also publicity and partnerships and collaborations and new business development. In fact, we're developing new products, too. So that's not something that Lisa was doing beforehand. So, I mean, I'm really excited about it. I think there's a lot of potential. And it's definitely really challenging. For me, I think the learning curve is pretty high. I there was a lot that I needed to learn, despite all the experience that I had. And despite all that she knew about my business, right? Yeah, just there's so much to learn every day. And I think the one thing is, and I think that, you know, you know, you guys are solopreneurs. And I'm sure most of your audience are as well. And Lisa was, but just for me, I just, you know, I worked in an office and there were people around all the time, and I had assignments and deadlines. And you know, there was really kind of, even though it was hectic, I knew what to expect every day. And it was annual A lot of things are cyclical, there's nothing cyclical about what we're doing. I mean, working in higher education is extremely cyclical. Yeah, every week is new, we don't know, it's all what comes into the email box, you know. So I mean, sometimes you can plan and we're really trying to be more strategic. But you know, being an entrepreneur, especially a creative entrepreneur, is a lot of sort of reacting to what opportunities come your way and figuring out how to make them work or not. Right. And so I think, by working together, there's a level of productivity that can happen now, which wasn't possible with Lisa's workload. I mean, it was really just whatever she could get to, and a lot of things weren't able, she wasn't able to get to. So it's good. And then we're also being strategic about what we say yes or no to. And that also feels really good. How are you strategic about

Kathleen Shannon: 33:15

what you say yes, and no to? Oh, we have a series of questions that you ask yourself, everything was said. So tell me because I need to know.

Unknown: 33:25

It's so I wrote about this a little bit in our in my book. So this like criteria criteria for saying yes or no. And it's an exercise that I did with Tiffany, my coach, a few years back, where, because I was really struggling. This was before, I even had as much opportunity as I have now. And but you know, we all know that stuff that you get used to over time, that feels easy. When you when it first starts happening for you, it feels really overwhelming. And at the time, I was overwhelmed by all the choices that I had. And so we made this list of like, what are all the things that least are important to you, Lisa, when you consider saying yes or no to a job? And of course, money was one of them? How much does the job or opportunity pay? How much time will it take? like do I even have time to do this, which is something that I unfortunately didn't pay enough attention to and committed to a lot of things along the way that I didn't have time for, and hence the all nighters. Does this project resonate? like is this like something that gets me excited? Is there you know, is there a sort of like resonance with either aesthetics of the company or their brand or their mission and vision that like feels very connected to who I am and what I do? And then there are probably some others but like exposure that less important for me now in the beginning, Was this something that were there was this an opportunity that would lead to other people hearing about me who might not have heard about you know, maybe it's doesn't pay much or it's pro bono, but you know, You have some not here. Yeah, I did some work for the Obama campaign, for example, where like, I, I didn't really have time to do it, but I did it because, you know, it was like Michelle came knocking Michelle came knocking. Yeah. So anyway, um, did you get to talk to Michelle Obama? No. But she did tweet out some of the work that I did for them, which is great. Yeah, so So now, it's not like we sit and say, number one, what is the pay? And number two? Does this resonate, but it's so ingrained? We will kind of like clay will read me an email now that's like, okay, we just got this email from blah, blah, blah, they want you to do this. Or, you know, here's what they would need it. And by when and sometimes she'll read it to me, and I'll say no, like, in two seconds. It's not that I'm not. It's just like, maybe not one of the five things I talked about is, is you know, so there's, there's got to be at least one nugget. And then if there's one nugget, then we dig deeper into the other stuff. And it really all depends. Sometimes I'll I don't have a lot of time, but I'll make time for an opportunity that just feels like something that I'd want to be part of. But yeah, those are pretty much the the main things we look at. And because ultimately you don't, I don't want to destroy the quality of my overall life. There's no point in doing this. If I'm going to be so stressed out all the time, or unhappy or not have time to be with the people I love and take time to enjoy this beautiful place that I live and enjoy my relationship. I will say, I mean, since we've moved here, our free time has really freed up. Yeah, no, it's great. All right, yeah, we've really didn't have a lot of time to enjoy our friends and the opportunities in California as much as we would want to. And just being here is really fun. I mean, we're going to go on a bike ride this weekend, and we hang out with Lisa's parents and family and sister lives here. And so there's just it's, it's pretty exciting. We're just in this exploring mode. And we're not No, we're busy. But it's not at the level where we're not having a life. Yeah, I mean, we want to scale my business for sure. And at some point, we may hire another employee, but not at the expense of our happiness and the quality of our life. I'm 47 years old. So I'm like, you know, I've already worked so hard since I was in my early 20s. Not always at this, but it's something I've always been pretty driven person. And now's the time that I'm I want to travel, I want to enjoy myself, I don't want to work more than 40 hours a week, if I can help it. I want to enjoy my weekends, I want to enjoy my family. I don't have kids. So I can, there's a lot that I can do with my time. And a lot of my friends don't have that time and I want to be able to enjoy it as much as I can just rub it in their face. Yeah.

Emily Thompson: 37:47

Oh my god, I'm gonna ask you, Lisa. So you your decision to bring on someone to really sort of help you in your business and not in a minor way, not in like an assistant way but in a very huge role is something that scares the crap out of a lot of solopreneurs I mean, a lot of them have a hard enough time hiring an assistant or hiring like even a virtual assistant, someone who has helped with the small stuff, but your first step was to hire someone to really manage a very large part of your business. So can you just quickly hit on hit on what what that decision making was like for you? Was it something that really did scare you and and you just spoke on like how it's really helped your life? But did you really anticipate it and just

Kathleen Shannon: 38:33

chat about that. And maybe even like, I'm curious to like the aspect of giving up some of that control. And I think maybe it's easier whenever it's your wife, like if I could, and I my business partner is my sister so it feels very much like I can give over some control to her I would kill to have my husband quit his job and come work for me but but there is an aspect of giving up that control that feels really scary.

Unknown: 38:58

Yeah, and in some ways, admittedly, it was easier to give up control to the person I'm married to than to some random person who I might have entered a partnership I'll actual contractual partnership with you know, I sort of trust clay in this way and trust that she understands me and appreciates me given even with all of my faults and shortcomings, and that she sort of knew fully what she would getting be getting herself into I think that's a lot, at least for me felt a lot easier than if I had hired someone or gone into a business partnership with somebody who I would be paying the same amount of money that I'm paying her but you know, with health insurance and all these other sort of like layers, not that I'm not paying for health insurance, but um, but you know what, it's different when it's another person that you that that is from sort of outside of your family. And so in some ways that made it easier in some ways that made it harder because now as you said, like I have this responsibility to her, of course, it's stripped scared the crap out of me like, what if all of a sudden I stopped making enough money to have a really good year last year, which positioned me really well to bring her on? And also to have clay say, Oh, yeah, we can do this because your track record is that you, you know, you, you could support to people. And but we also have this understanding that if after trying this for a while, and it doesn't work, she's going to sort of be able to walk away, I don't necessarily think that's going to happen. I mean, our marriage comes first. Yeah, so and that was what was the most important thing to us. And even if if I had hired somebody from the outside, I would have wanted there to be an out for that person, because you never want to sort of force somebody into something that makes them feel trapped. I was scared, because I knew that, you know, I was going to be responsible financially. But we also have to had to shift the thinking. So clays now responsible also for, for helping to bring in the income, this isn't about me play working for me, and I have to feed her and pay her and pay her health insurance. This is about both of us being proactive about making an income and figuring out the best ways to do that. That also means that I have to listen to her opinion about and her perspective on what she thinks it's going to take, it can't always be me making all of the decisions and having all of the power. And so I'm having to give up a lot of control, in many ways, but I actually like it, I kind of feel like it relieved in a way like, there's no way to describe this, I guess most of your listeners are solo on solopreneur printers, and they understand what this feels like. But there's this huge, like alone feeling that you have, like, everything falls on you. And I used to wake up in the morning and just be like I have so much to deal with today. And I would like not be able to eat for like three hours. And because I was so overwhelmed. And I don't feel that way anymore. Like sometimes I get a little stressed out by having to finish certain things are deal with some this or that in a project. But now I know I have clay like she's helping me like I have support and somebody who's right there with me. And I just don't feel alone anymore. And there's it's indescribable that I can get up and do what I do every day. And I make money from it and have this person who's like on board supporting what I do on the art making part of what I do and and joining in my businesses and is invested in what I do as as I am. Not just because she loves me, but because you know, she's invested in making the income that we want to make to support ourselves and live a good life. So and we're both invested in not failing at this. So that feels good. And that's been really apparent. Yeah. I was just gonna say what I used to come home from the office, I was so fried because I was talking all day. At my last job. I had upwards of 14 meetings a week. And I had several employees and we were constantly talking and it was an open workspace. And then I would commute on this bus with everybody talking or just on my cell phone imagine was just just just constant stimulation, and I would get home. And we would be sitting down for dinner. And Lisa would just like talking, I'm like, Oh my god, I love you. But I can't I just went I had I had been alone all day like not talking to anyone. It was jarring. But I understood it was just tough because I was just done with work. And I was able to shut it off. And she just was waiting and waiting waiting to talk. And it's so nice that we can now we can just talk during the day about and process it all in real time and then enjoy our relationship is I think actually gotten better. Like at dinner, we talked about other things.

Kathleen Shannon: 43:56

Well, so I'm curious actually, like what a day in the life looks like for you. And I guess specifically even Lisa, like, how much of your time before clay came on? Like if you had to draw a pie chart? Were you actually doing art and illustration? Like the thing that you love doing the most? Or that your that your brand is centered around? Is this talent that you have? How much time did you spend doing that before? And how much time do you spend doing it now? And like just kind of like if you could walk us through your day from start to finish? What kinds of things clay Are you responsible for doing what is your day look like? And Lisa What is your day look like?

Unknown: 44:31

Well, it used to be that I would you know if it was a pie chart, I would say it was half and half and it had to be like because I I you know in some days, I probably could have spent more time and some days I did spend the entire day doing non art stuff just to sort of like support the art making part. But by default at some point or another I had to like make the work to turn in. And that's I think what makes being what You know, being a graphic designer and illustrator and artists different, like you actually have to produce stuff. And there is are ways to make passive income. And we're working on that more and more. But a lot of what we do, what I do is actually making stuff, even if it's stuff to post on my blog or post on Instagram, you know, promotion is part of part of my job, too. So now, I would say that it's probably. So it's 5050, I would say I spend more like 65 or 70% of my time making art and 30%. Other, we haven't. And that's partly because clay is still learning all and we're still developing all these systems, she's still learning, I still have to help her with some backend stuff on the website and things like that. And also, I don't know that I ever want to have my hand completely out of all of that stuff. If that were the case, then clay would end up doing every nitty gritty thing, every piece of administer boring administrative stuff. So we do things together, we share a locking and shipping or both. Yeah, like, it's not like, Oh, I have this person working with me. Now I am not going to touch packing and shipping Etsy orders ever again, like we both do that. I still do most of my own social media. Clay is helping me with an editorial calendar and scheduling it and coming up with ideas for things I can write about and post about and things like that. But I don't know that I'd ever want artmaking to be the full pie. This person, right? Yeah, I like actually other parts of it too. But it's so much better to be spending 65 or 70% of my time making art than it was 50. Even though I like all the business parts of it. Not necessarily all of them. But a lot of them. I'm glad to have turned those over to somebody else who I trust so much to handle them for me because has really changed things. We get up in the morning, like we go work out most days, sometimes together, sometimes separately, we belong to a master swim team, we go to spin class, we this morning, we weren't running, sometimes we do it together, sometimes separately, and then we come home, shower, eat again, and get to work usually by 830 or nine. And then the whole day is some combination of communicating about what we're going to do that day to each other and what our goals are. And then trying to break it down. There's a lot of disruption that happens. But email comes in and you have to deal with things that weren't on your to do list sometimes. Yeah. Yeah, my job is pretty much all marketing and operations. So it's broken down sort of, like 60% operations, 30% marketing and 10% new product and business development. So that 10% wasn't something that was necessarily prevalent in Lisa's past role, because I think it was a lot of on the receiving end, like Oh, these new projects are coming in. And so we're trying to be more strategically we talked about earlier about developing our own product lines or other partnerships. So that's been fun. But yeah, my day, you know, it's it's different. I had so so many meetings at my last job. And every job I've had, I've been, you know, working in an office for 20 years. So being employed by employer. So now I have to structure my day differently. And we're creating just a lot of to do lists and tasks lists, and we have our workflow, so many shared documents in Google. Oh, yeah, it's crazy. But they really worked for us. And I have a few that are just mine. And she has some that are just hers, right? A lot of stuff that we check in, in developing systems, because now she answers my email, like what do I need to look at or not? One thing I will say and this is a commitment, we made it that day long retreat we had before we started working together was that we were going to stop and eat lunch together every day. And there would be no eating lunch in front of the computer. And or going out Yeah, and so we do go out to lunch about once a week to and it's been great. Like that's something I never could have wrapped my head around before. Like I never stopped working even when I was eating like I might stop for five minutes to prepare something but or to grab put some leftovers in a bowl and put them in the microwave. But there's this hilarious cartoon or some sort of meme or something that I saw once about how like the work at home Freelancer was like eating like raw edamame, a from the freezer and like Clif Bars and stuff. I mean, I wouldn't say Lisa was that bad but she definitely ate like at her desk and in my Yeah. And so now we're like, we stop and we say okay, what do you want to stop for lunch today? Like today? We had a conversation. Oh, we're taping. What's being boss ladies at noon you want to eat? It's lunchtime. Right? So shall we before, shall we after we actually talk about it. We talked about a ways to do meal planning for dinner. But now we do meal planning for lunch and it feels really civilized. And we actually Don't force ourselves to stop talking about work during lunch. But we force ourselves to sit down at the kitchen table and eat. And that's been a total life changer for me. And one of us will stop in the afternoon and walk the dog. We bought a house recently, and we have all kinds of contractors and things happening with that. So we have to often stop during the middle of the day and deal with people who work during the day. And so we take turns doing that sometimes we do it together, it feels very flexible now that there's two of us and not just me that I can take more breaks and, and go with the flow more. And that feels really good. And then we kind of by four o'clock, we're like, when do you want to wrap up today? And I might say, I really need to work till 630. I've got to finish this. And sometimes I say, let's wrap up in 30 minutes, you know, and we call it call it an early day depending. It's a kinder, gentler Lisa Congdon, are you guys mind sharing some of the other? Like, what are some examples of some of the other commitments that you made during that day long retreat? Um, well, you know, I feel like, there was like a setup sort of working together ground rules. And like keeping it positive. I'm a very sort of solution oriented person, one of the ways that I feel that I, one of the things that I think has contributed to, like living this life that I've always dreamed of, is always even when something appears to be going wrong, like, what's the positive spin on this? What can I learn from this? How can I take this and move, change it and move it around? How can I use this situation to my advantage? How can I get out of this situation quickly for a positive ending, whatever it is, keeping it positive. And saying solution oriented, felt really important to me. And that was a something that clay was really on board with too, which is really hard sometimes, right? Because you find yourself complaining about a client or a situation or this thing is never ending. So that's one norm we have mutual trust and collaboration. Just respectful, calm conversations and keeping things light and not so serious. And, you know, I mean, we have this phrase called we chose this. Yeah, we chose this like, it's even when it's hard this is this is a choice we made. So let's make let's make it fun. Sometimes that's putting on music and dancing around the apartment a little bit. Sometimes we just listen to fun path podcasts like yours, and others that we enjoy. And like I said, it plays like how do you when she she's asked me a lot of questions that she started, she's like, how do you keep this on? You know, like, how do you not go crazy. And it's like, Well, again, I chose this. So I get I'm the boss, I get to decide how I spend my day. And I, I know that all of this, even though it's overwhelming is like where I want to be. So I, if I want to drink tea, when I want to drink tea, I drink my tea, if I want to watch an episode or a marathon of some TV program on Netflix while I'm drawing, then I that's what I can do. Like you cannot you can't do those things in an office necessarily. And you have to make your own rules when you're your own boss. So I said to clay, make your own rules. If you want to go to a cafe every day for a certain period of time, that's fine with me. Or if you want to, you know, blast music and your headphones or listen to certain things or work certain hours and take breaks at certain times then do that. So giving each other a lot of we decided early on that we were going to give each other a lot of freedom to kind of create the work life day. Yeah, that feels good

Kathleen Shannon: 53:36

is fun for you. So clay what after working somewhere for 20 years, what are some of those rules that you have had a hard time letting go of? So I remember even whenever my sister quit her job as a VP, creative director to join forces with me, one of the things that was really hard to let go of was like the physical tangible job jackets that we would use back in our ad agency days to like, keep track of our jobs. And I was like, Oh, no, Google Docs, like, we don't need job jackets, you know, something like that. That was like a really hard thing for her to break. And so there has there been anything like that that's been hard for you to kind of let go of or that that kind of structure that you crave? And then on the flip side of that, what are some new rules that you've created for yourself?

Unknown: 54:21

Well, I think what's been the most challenging for me is that I feel that I'm trying not to feel like an employee or that I you know, expect things to be exactly like a 40 Hour Work Week. And I think I bring that to this new position. And that's probably a good thing. I mean, I don't know, I think that it's actually going fine. I think that what was the second part of your question was like, what what you're saying what,

Kathleen Shannon: 54:51

like, Is there anything like any sort of that structure that you are having a hard time letting go of or that you crave or that you know, and like you just said you're kind of boring. Some of that to it. But then also, is there anything or what are some like the new rules and boundaries, because I think that whenever you leave your day job, it's like the world is your oyster, you can do whatever you want now. And so it is kind of, I think, important to not just throw all the rules out the window, but to create your own rules. So like, what are some of the rules that you've created for yourself?

Unknown: 55:23

Okay, so what the what the leaving behind things, actually, the the, in we're working on this with Lisa, but I, while I complained about all those meetings, they're actually really effective. I love brainstorming, and I love mapping things out. And I love to talk. And, you know, I, it got annoying, but I did have an employee who I loved, who who interrupted me quite a bit, and I just would always just stop what I was doing and say yes, you know, then he would talk. And it was good. And sometimes I go interrupt him and you know, it was sort of that atmosphere of, of talking things out, and then projects would come up. And then you would walk out for coffee, and you'd see co workers it was just has such a big identity at my last job and cetera. But she told me this morning when we were running, actually, which is when we kind of work a lot of this stuff out. She was like, I realized that one of the things I'm missing is this idea of like brainstorming and collaborating and getting on the same page with you so that I don't feel like I'm guessing all the time. And can we make more time I know, you want more time, you know, you want to I don't want to take too much more time away from the actual drawing and painting you need to do. But can we make time for more more brainstorms and meetings? And I was I love those two, actually. So I was like, Yes, let's do it. So um, what we're trying to do is take that aspect of clays job that really worked for her this like team idea and brainstorming sessions and like creative thinking with another person. And bringing that into my business as a way to really like figure out what's next for us or, or even how to get through a sticky situation that we're having on any particular day. Yeah, and I actually recently joined an all women's mastermind group. So that's a monthly group that there's seven of us. And so it's really new for me. But so far, it's been really helpful for me to talk about what's going on with my business and what I'm struggling with, and what I'm challenged with, and getting just a lot of advice and interesting perspectives. And the group is interesting. It's, it's, no one is doing what I'm doing so and they're not doing what each other are doing. So there's no competition or anything like that. It's just really smart women. So that's been really helpful, too. It's, I think it's just like a little extra bit of like giving me what I'm craving. So those are some like new things that I'm working on. And you know, I've really worked really, really, really hard at, I work hard at everything I do. But my last job required me to be on that a level that was very burnout, audible. And I'm like the new rule I'm creating as to just kind of be a little bit more laid back and stress free and sort of not like this whole idea of like kind of trying to find humor and things and taking things lightly, more lightly, I think is really important because we're not you know, I was working at an art college. And I know, it seems crazy to think that, you know, it wasn't brain surgery, anything like that. But there were times where I'm thinking, Oh my gosh, like, you would think that we're like doing brain surgery. You know, we're like trying to Worlds the world revolved around everything I was doing is so stressful. I mean, it was in our colleges institution. You know, it comes with a lot of red tape and bureaucracy, and it was very, very stressful. And I'm just not going to let myself get stressed out anymore. Yeah, like Tiffany would in our in our retreat. At the end. She was like, what's your motto? Like? It's just our like, yeah, we love what we do. But really, it's it's just art like, No, no, no client no fan. No, you know, no annoying person. No annoying situation is really worth losing your mind over because yeah, it's it's just art. You know? if so how? how stressful it can be really make this, you know, we don't need to make it super stressful. So yeah, so yeah, not that art isn't amazing. But it's Yeah, no, it's

Kathleen Shannon: 59:23

so funny because I think it is easy, especially if you're type A or driven. No matter if you're doing brain surgery or art or whatever you're doing, you're going to be able to create your own stress in it. So I was even having my tarot cards read recently in New Orleans and the tarot card lady, she was like, and maybe you could read anyone this way, but she was like, Don't make stress where it doesn't exist. And he's like, Oh, you're so right. But I love I want to say I love how you guys attach like a motto or a mantra. So we chose this and it's just art. I think that that is so important in keeping things light, like that's a really good way just to have those little triggers that remind you of what your goals are and what your boundaries are.

Unknown: 1:00:08

Yeah, we find ourselves reminding each other of that, like I would say, on a daily basis, those little things that we've come up with that are sort of like the, you know, the foundation of our relationship and what we're doing every day. I mean, we have really lofty aspirations and goals, for my for my art career and for our business, but not at the expense of, of our of our happiness and a sense of equanimity. All right, any

Kathleen Shannon: 1:00:39

final advice for being a boss in work in life? For our listeners?

Unknown: 1:00:43

You go first? Oh, gosh, well, I think this is where the working 20 years and an office comes. But I just I personally don't do the pajamas in bed kind of thing we get I for me, I get enlisted to I mean, I get dressed every day. And and and, you know, do my hair, I'm wearing dressy, dry clean shirt. Not just because we're being recorded either. And, and just make the bed immediately. Yes. So. And you know, I really actually, this is, again, probably coming from my experience, but I really do like the whole nine to five thing I like being available when other people available. And I like to, to, you know, close it down at the end of the day. I also just really think that it's a, I think what I learned in managing people I was the supervisor for and had other interns and students that I worked with. But I think just working with them, and just the communication skills that I gained over the years of sort of giving feedback, and also just having to manage so many different people's expectations on a daily basis, I just feel that communication, as an entrepreneur is so so important to not just leave it to email, I think if you need to talk something out, you should pick up the phone, she gets on the phone all the time. It's something that I don't like to do. So. Yeah, I think it would just I just I'm used to talking things out with people. And that's an experience that I think is extremely valuable. I mean, I've had to fire someone, you know, that wasn't pleasant. I've also got to hire people and give them positive feedback and reviews. And so I just have so much experience kind of just cutting to the chase now, but I didn't have before. And so I think that's going to help with our negotiations and in working with clients. And that just makes me feel like a boss. So I don't know how else to say it. You know, that's just just just not being scared to just talk things through and just being really confident in your communication with people, whether they're vendors or people you would hire customers. Yeah, that's sort of my philosophy. Anyway, Lisa? Um, well. I think the main thing for me is this idea of confidence that that clay just alluded to, but this idea of owning whatever situation you're in, or whatever your particular path or experiences I feel that I hear so often from people, Oh, I wish I could do what you do. Or I wish I could be this or that, or I wish I could do this or that. But I'm not young enough. I'm not pretty enough. I'm not smart enough. I'm not organized enough. I'm not talented enough. I have five kids and drive around in a minivan. I lifted out that last week, from an actual person, you know, how do I? And um, my, my answer to that is, um, it may appear as though I have the perfect career life situation, but I don't and none of us does. We all sort of make do with what we have or embrace what we have, and really make that the thing. So whatever your life is, whatever your experiences, whatever your ages, whatever, you you know, whatever, own it and make it a positive thing and something that you embrace and not something that you're ashamed of. I mean, that was for me, the turning point in my career was when I stopped being embarrassed by these things that I perceived as shortcomings and started embracing them. So I started writing more on my blog about the fact that I'm almost 50 and that I didn't start my career till later in life or that, you know, all of these things that felt me were a source of embarrassment for me are now the thing that actually I feel like connects me to the most people in my audience. People want to hear the real story of you and owning your experience at all, every part of it, even the parts that make you anxious, I feel like is really important and sort of people will start to perceive you as somebody who, who, you know, has their shit together and or history together. And you know, no matter what Your life experiences think about it like mean there are bloggers and business owners and artists and designers out there from every possible you know, walk of life, religious background, economic background, and the people who are successful all have one thing in common and that's it. They're not trying to hide who they are, what their experiences they're trying to use their life experience and their perspective to grow their business and and so instead of making excuses like owning your experience and and doing it anyway I feel like is what makes people a boss, and it's what made me a boss essentially.

Kathleen Shannon: 1:05:39

Hey, guys, I wanted to tell you about something fun that we're doing. Coming up this fall, Emily and I decided that we wanted to go on vacation to New Orleans, one of our favorite cities in the world. And we thought wouldn't it be fun if we invited you to come along? Go to being boss calm slash Nola. And learn more about taking a vacation with us. We hope to see you there.

Emily Thompson: 1:06:02

Thank you for listening to being boss from Emily Thompson and Kathleen Shannon find Show Notes for this episode at love being boss calm. Listen to past episodes and subscribe to new episodes on iTunes, SoundCloud and Stitcher. If you like our podcast show us some love by reviewing being bought from iTunes and share it with a friend. Do the work. Be boss and we'll see you next week.

Unknown: 1:06:48

Amen.

Kathleen Shannon: 1:06:53

How to Get it in there somewhere. So people in our Facebook group has started a drinking game. Where every time Yeah, every time we say Amen, take a shot or okay. They said whenever I say

Unknown: 1:07:07

I know you're talking about anyway, so we had to get the awa Yeah, that was really late. But good. Good job we'll

Emily Thompson: 1:07:16

work on earlier.

Unknown: 1:07:18

Just trying to get our listeners drunk at the end.