Episode 60: Cathi Bosco

Hallway Chats

Introducing Cathi Bosco

Cathi Bosco is a creative professional, nature lover, and visual communications designer working to make the web a better place for all.

Show Notes

Website | C&D Studios
Website | Docs with Apps
Twitter | @bethebreeze

Episode Transcript

Tara: This is Hallway Chats, where we meet people who use WordPress.

Liam: We ask questions, and our guests share their stories, ideas and perspectives

Liam: And now the conversation begins. This is episode 60. Welcome to Hallway Chats. I’m Liam Dempsey.

Tara: And I’m Tara Claeys. Today, we’re joined by Cathi Bosco. Cathi is a creative professional, nature lover, and visual communications designer working to make the web a better place for all. Hi, Cathi. It’s great to have you here.

Cathi: It’s wonderful to be with you today. Thanks for having me.

Liam: You’re most welcome. Thanks for joining us, Cathi. Please tell us a little bit more about yourself, if you would.

Cathi: Well, I’m 21 years old with 30 years experience, as they say. I’m a mature designer. I work out of Connecticut. I have been self-employed since I was 30. That’s 21 years now. My husband’s also self-employed. We work really hard and fixed up an old farmhouse and graduated from art school and have been real self-motivated entrepreneurs. We’ve had highs and lows with that process. I started full-time on my own to stay home with my dog. I really recommend that as an incentive. If you want to start your own business, get a dog.

Tara: I love that. You and your husband both work for yourselves. Do you share an office or work from home? What is that like, being together that much?

Cathi: He does not work from home. I’m the one that works from home. When I first started working full-time designing and drawing and doing commission portraiture, I worked in an attic, and now I have a studio outside that’s connected to my garage so I have to leave the house to go out to the studio, which is awesome. He works outside the house. He’s a painting contractor so a little bit independent.

Tara: That’s great. Do you both then have a good amount of flexibility that you’re able to sort of pick up and go whenever you want to and give yourselves as much vacation time or is there more pressure when you’re supporting yourselves? You’ve always got to have work and it’s hard to say no to anything so you never take a vacation. What’s that situation like?

Cathi: Yeah, we never take a vacation calm. If we do, we go visit my family because I’m from Colorado. We rarely take vacations. Seems like my busy time is his slow time and his slow time is my busy time. Yeah, with the cost of health insurance and all of that. It is definitely more challenging.

Tara: Yeah, I can imagine that’s the case. I think a lot of people who are self-employed rely on their spouse or significant other to cover benefits like health insurance and it is expensive when you work for yourself for sure.

Cathi: It definitely is.

Tara: Can you tell us a little bit about where WordPress fits in and with your graphic and art background, how you came to be introduced to WordPress and how you use it?

Cathi: Absolutely. My background is in fine art. I’ve always been a visual artist. I started running with a trail running group in Connecticut when we moved here. The leaders of our running group had a little WordPress website. I started learning WordPress on that site. It was for building community and inspiring each other to run further, farther, longer. Some of the people in the group run hundred milers, there’s a lot of ultra runners and things like that. Everybody’s a little creative and entertaining with all of the training that goes into those types of adventures. I learned on that website. And then as an illustrator, I needed my own website. I needed a way to get my own portfolio online. I didn’t start out with my Portfolio on WordPress because that seemed a little bit daunting so I was using things like, oh, you’ve heard of Geocities and those old applications. Learning WordPress was very empowering to me once I got my portfolio moved into a WordPress website. I started empowering others with it. A friend started a craft brewery, I would build a website for them. I just really loved it and I became certified with the Adobe Suite so that I could do all of those interactive types of digital drawings. Because my studio was completely analog, because all I did was draw, and analog photography and film, and that sort of thing. I definitely felt very fortunate to ride the digital wave and to transition into completely– now we’re 1000% digital. But I still draw on those skills and I just love the web so much more because it’s immediately gratifying. You can share it immediately. It’s much more animated, interactive.

Tara: So your preference is digital over analog now?

Cathi: Yeah, I’ve done so many drawings and stuff over the years. We’ve just cleaned out our attic. I’ve done hundreds and hundreds of commision portraitures and I can hardly remember half of them that I’ve done. I know that people cherish their drawings that they do of their kids or their family or whatever we did for them, some sort of memorials. I did a lot of memorials. That was really fulfilling work but it’s just– I don’t know, it feels a little less interactive to me. It was meaningful work but I prefer this now.

Tara: Yeah, and people digitize all of that stuff now. You can now digitize it and perfect it and do a lot more than you could do when you were doing it just by hand. I know, I used to do illustration also. I look at the tools available now and I just think, “Oh my gosh, I would have saved myself so much time.”

Cathi: [laughs] I know, it’s true.

Liam: And you could have one pen.

Cathi: [laughs]

Liam: “Which one of the 87 pens do I want to use? I’ll just this one and change the settings.” It’s just amazing.

Cathi: Things have really changed and I’m so grateful that I was able to change with things because when I was in art school, there were no– it was beta VH 1, Analog Photography, Filmmaking was not digital.

Liam: I want to ask you about that because Tara and I both have print-design backgrounds and we’re perhaps not young enough to have started digital, we transitioned as well. I want to ask you about how you came to that kind of emotionally, psychologically, mentally? Because we’ve all embraced it, right? We make WordPress websites and we’re on a podcast. But there can be challenges and some things about web design I didn’t immediately like and I really struggled with from a design control standpoint. It sounds like you just loved the opportunity and didn’t have any qualms about embracing it, but maybe you can just dive into that a little bit for us?

Cathi: Well, it’s true. It was incredibly frustrating to learn the tools to express the way you wanted to learn to express because you couldn’t immediately use Illustrator or Photoshop, you had to learn how to make the kinds of visual representation you wanted to in a whole different way.

Liam: Sure. Because you could knock out a sketch of somebody and 20 minutes to an hour, again, depends on the detail and stuff, but if you’re just in Photoshop or Illustrator, it can take you an hour to figure out where to get started in Photoshop.

Cathi: Yes, I would give myself– I wrote a children’s book and I joined a children’s writing group, and my challenge was to layout, illustrate, write the whole book using Illustrator as a way to teach myself so that I could become fluent.

Tara: Did that take a long time? Was it faster than doing it by hand?

Cathi: Oh, no. It took a while. [laughter] No, it was really hard. Of course, I had to overcomplicate it for myself because I wanted each page of the book to connect so if you stretch it out long, it becomes one really long, long drawing. Of course, frustration factor there, how you have to learn how to do bleeds, and how to line things up, and folds, and all of that stuff, and make all of your illustrations line up. It was a good exercise but creatively, I had something to say so that helped. I didn’t have to think of something I wanted to do creatively. I had that in pocket.

Liam: That can make learning much easier if you know what you want. If you have a view of the end, then it’s just figuring out the technical of how to make that happen. Before I turn the mic back over to Tara, let me ask you one question. Illustrator or Photoshop?

Cathi: That’s like choosing a child. I would put them both in the boat and save them both. [laughs] The question I would ask is– now I’m using Sketch a lot and can I get rid of one, but I need all three now.

Tara: Yeah, I know. I’m trying to do that, too. I’m actually using Sketch to do some logo work because you can export it so easily to .spg but it doesn’t have all the stuff that Illustrator has. You can kind of copy and paste back and forth between them I think, but there needs to be something that–

Cathi: I love Sketch for laying out website designs.

Tara: Yeah, it’s perfect for that.

Cathi: I need to use my Illustrator program to bring smart objects over into Photoshop. I can’t do without any of them.

Tara: Yeah. We could geek out on design tools probably for a lot longer but I do want to kind of get away from the technical stuff a little bit and just talk a little bit more just about life and how you view life, and specifically how you view success, Cathi? You work for yourself, your husband works for himself, you’ve done that for a long time. I think that wouldn’t work if you weren’t successful at least in the ability to support yourselves. But can you talk to us a little bit about what success means to you in your business life, but maybe how that integrates also into your personal life as well?

Cathi: Sure. I was expecting a little bit of this question based on your podcast and I do love that about your podcast, that you talk about the human experience of things and challenges. I think for personal success, which is most difficult for me to probably articulate, I think I’m personally successful at being positive. I don’t think I deserve any credit for that. I think I’m just sort of born with this chemistry that can stay very positive through incredibly difficult challenges like loss, or illness, or any kind of strife. I’m able to stay really positive and that’s been a real key to my success as a personal person. Because I’ve had cancer a couple of times, I’ve lost relatives. Everybody has had a lot of life hardships by the time they’re my age, I suppose. That’s something that I’m really grateful for. I don’t really get myself a lot of credit for it but I’m really grateful that I have a very positive outlook on things. That’s how I would define my personal success. I still can eat an entire sheet cake if I’m really disgusted about something and I’m not proud of that. [laughs] And professionally, how do I define professional success? Professional success is, in my work, facing a lot of challenges because when you do creative work, you deal with a lot of rejection or a little bit forward, a little bit back. You’ve got three types of clients, ones that want you to just do all of the decision-making for you, those are really fun. Then you have clients that just want to use you as a tool to make whatever they think or to do whatever they think. They don’t want your advice. Some of those are unsatisfying. I don’t find that to be a successful way of working. But most of the time it’s 50/50. I’ll collaborate with you, I want to meet your vision and make sure that what we’re doing together, I can provide some insight based on my experience as well. Together, we come up with something even better than one of us can do alone. I love collaborating that way. Good collaboration is a success for me.

Tara: How do you find that? Sometimes you don’t know that until you’re already down the road with a non-collaborative client or project. I guess that’s something that you assess as you’re in the middle of it but it’s not something you can necessarily create or avoid.

Cathi: Right. That’s where experience comes into play. I try to nurture that in the relationship initially. Usually, you can tell right from the beginning if this is going to be a good fit, as they say. Sometimes, I’ll take on a project where I’m just the tool and I’m just going to execute these– that’s fine. As long as it’s well-defined up front. I don’t really have a preference but if there’s not going to be a healthy collaboration and a bad fit, that’s when I’m like, “Okay, we’ll just say this isn’t going to work.” And I’ll refer them to someone else. Over the last few years, I’ve really changed the types of projects we take on. I used to do a lot of ‘mom and pa’ websites, smaller local business, or people who are maybe finishing one career and moving into another of their own, little startups. Now I do much larger projects, and they’re mostly b2b projects. People are in that collaboration kind of mode more. That’s helpful.

Liam: Yeah, I find it’s really helpful to talk about how our clients work when we’re vetting whether or not to take on the work. And we just chat about what’s your flow, what works for you– because as you noted, Cathi, there’s a time and a place where you just want me to make the red bits red and blue bits blue, and you make this go over there. Yeah, I can do that, but if I think, “Oh, I would like to make the red bits orange.” And I have no creative say on that, and I thought I was going to have some, as creatives, that can be hugely frustrating. Isn’t it? That’s really interesting to try to weave that all together. I think I totally agree with you that after a few years in the business of trying to figure out how people work, there’ll get to be some telltale signs about, “Okay, this is how it’s going to be.” It’s as much as managing our own expectations as our clients, isn’t it?

Cathi: Yes, and setting those benchmarks like, “We’ll get to this point and you still have no idea what you want to do.” We’ll just set some benchmarks as little safety measures where we’ll go to this point. And then if it’s working, we’ll move forward, if it’s not, it’s not. Little safety nets are helpful.

Liam: I like that, I like that. To achieve this success, and we’re talking about professional success because it sounds like you’ve got a handle on personal success.

Cathi: [laughter] The sheet cake!

Liam: We all have our vices, we all have our challenges. And if you’re in a trail running club, then you’re the kind of person that can maybe eat a sheet cake and you’re going to pay for it days and maybe not for a year. We allow our strengths to compensate for our weaknesses. But let me talk a little bit about professional success. From what you were saying about good collaboration, what’s the single most important thing you can do professionally, or maybe it’s personally, to achieve that professional exist, to achieve that good collaboration?

Cathi: Communication, without a doubt. You have to be good at communication and overcommunicate sometimes. I think providing status updates on how work is progressing, talking about what expectations are. I’ve learned so much from collaborating with other professionals. I sort of needed to collaborate because I got sick some years ago, and I needed to be able to hand over the studio for a period of time to someone and I really hadn’t prepared for that. It also helped me with pricing work, to collaborate. Because I want to be proud of what I’m handing over to someone else or asking them to handle for a while or indefinitely. What would they charge for that? I don’t want to undersell myself. That was a good way to sort of make sure I’m not undercharging for the work I do. I guess that’s a personal problem of mine. Sometimes I underbid.

Tara: It’s common.

Cathi: [laughs].

Tara: Yeah, it’s common.

Cathi: Communication.

Liam: That’s a really good point and that’s a challenge certainly for a lot of self-employed. I remember I started working for myself part-time in about 2004 and by 2006, I was completely on my own. 2009, I hired an employee. Going from, “I make all the decisions, I do everything.” But also not in a legal way, but like, “If I don’t do it, nobody does it.” To, “Oh, somebody else wants to do some of this project. Alright, I guess I can share.” And I’m not necessarily deliberately selfish but I just wired myself to do all this and then to think about, “No, I do need to talk with them. I do need to share, I do need to collaborate.” That can be a challenge kind of figure out. I wonder how you walked yourself through that realizing you need to collaborate and then a desire and the value. How did you walk yourself through that?

Cathi: I think that I had a great mentor. Someone mentored me and then I began mentoring. I think that through teaching and sharing of knowledge, you begin to collaborate better. My first employee was a woman who was in high school, who was volunteering to learn a little bit, to get involved in some studio work. And then she became an employee for a while and she came back through college. I take on an intern for a few months and then they’ll stay with me for a period of time and right now, Ryan is with me. He’s been with me for some time now. He studied video editing so he doesn’t necessarily have a web background but he’s got a great design eye and digital background, we just click creatively and I’m happy we give him tasks because he teaches me a lot and I teach him a lot. I think mentoring back and forth helped me get comfortable with collaboration.

Tara: That’s really great that you found someone that you can mentor but who can also teach you some things and who, like you said, you click with. That’s almost a miracle to find someone at that point in their career that it works like that, that’s awesome. I’ve seen some of the videos that you posted lately and they’re wonderful. It’s a great service to offer.

Cathi: Thanks. He’s pretty terrific. He won’t be here long. I’m sure he’ll outgrow me soon.

Tara: Yeah, the problem with us as small agencies is that maybe it’s not full-time or it’s not the same kind of permanent long-time job. But that’s great that he was there, or is there for as long as he is. It sounds like a great fit for you.

Cathi: I’m working him, grooming him to be a good remote worker too, so when he does want to move to the woods in Maine, he’s got some part-time remote work he can count on. He’ll be around, we’ll be friends for a long time I’m sure.

Tara: Awesome. Cathi, I know that you started working a little bit with the WordPress team, I guess, and the design team there. Can you tell us a little bit about your involvement with WordPress?

Cathi: Sure. I’ve been going to WordCamps and WordPress WordCamp US the last few years, and I was not able to stay for a contributor day until this year in Nashville. I stayed for a contributor day because I had trouble beginning to contribute back to the design team online without actually working with some people, like at a contributor day where you have to learn Trac, and there’s GitHub, there’s the Slack channel, there’s the handbook, there’s all these different ways that the design team builds WordPress core and WordPress.org and all that stuff. It was just very difficult to become involved on the team. At contributor day, I networked with the people who were hosting the design table and really dedicated myself and found a group of people we can kind of make a buddy system to learn how to use Trac and to get in the flow of contributing. I highly recommend that. We’re starting to work on onboarding designers to the team for WordPress. We’re actually in the process of creating a buddy system set up so that people can sort of learn their way around Trac and how we triage and how we work on the design team. I love doing it, I’ve empowered people with WordPress over the years a lot. I get a little self-actualization personally for contributing back now. We’ve been doing some plugin designs, we’ve been trying to onboard more designers, laid out some pages for WordPress.org about how to create a blog. There’s really nothing on WordPress.org about how to make a blog or how to move your blog from another platform. I really like working on the WordPress.org stuff a lot and doing some of the design assets and I feel like I really want to see it grow. I love WordPress, I love that it’s open source, I love that it’s a content management system. I love the community. It’s just been a fantastic tool for me and it feels good to give back. It’s hard to find the time all the time. I’m not a big agency like Automatic or something that can just dedicate certain amount of staff hours. I’m putting in at least four hours a week, contributing and doing work with my team.

Liam: That’s a significant amount.

Tara: It is.

Cathi: Yeah, I try to keep it four. [laughs]

Tara: It’s interesting to hear that your experience at contributor day is what kind of pulled you in. I’ve tried a couple of contributor days and I find them overwhelming because there are so many people who want to help and there’s only so much that the person that’s sort of coordinating everyone can do. I think it’s hard to actually contribute sometimes at contributor day because nobody can really get direction of what to do next. If you’re able to have this buddy system, that sounds like a great plan. I would love to see that incorporated in other teams within contributor day, so that’s really good to hear.

Cathi: Yeah, because then we can follow up with each other afterward in the Slack channel on projects and the two of the ladies that I sort of buddied up with are now leading the design team. I think the design team has really done a lot this year. Well, with Gutenberg coming out I think a lot of designers got pulled onto that project a lot, too.

Tara: Great, that’s good to hear. I’m going to transition again and ask you another question that we like to ask everybody, which is about advice. If you can share with us some advice that you received, one piece or maybe two of things that people have shared with you and how you have incorporated that into your life, what it means for you?

Cathi: Well, I think I don’t have anything super profound to share but I will say, if you say you’re going to do something, you do it. If you can do that every day, say you’re going to do something and do it, then you’re pretty good. You’re going to manage your stress level pretty good. You’re going to get good feedback from the people around you. I think those are words to live by for sure.

Tara: Does that go for an internal dialogue as well as an external one?

Cathi: We have to be accountable to ourselves, too, yeah. I’m much better at the professional side of that, the external side than the internal because self-care is really, really difficult. With what we do, we’re always doing all these tasks and reaching and going further. We don’t always save enough time to take care of our internal selves. That’s something I really work hard at and struggle with at the same time.

Tara: Yeah, when you have your own business, there’s never nothing on your to-do list, there’s always something that has to be done. If it’s reconciling your bank account or updating your own website or creating a video for your website.

Cathi: You update your own website? That’s so awesome. [laughter]

Tara: It’s always on the list.

Cathi: Yeah. I walked this morning, I got my walk in. Even though it wasn’t quite as long, I tried to do that. I tried to immerse myself in nature and the beauty and the natural world for my mental and physical health on the daily basis. That’s my practice, that’s my meditation.

Tara: I like that advice and I’d like applying it to both conversations, both dialogues, with yourself and with others so thank you for sharing that.

Cathi: Sure.

Liam: We’ve got a little bit of time left and I just want to ask because we are human and I think while your advice is great, it’s one that a lot of us in time fail to achieve. How do you fix when you fail to deliver what you said you’re going to do? What does that look like? If the advice is, “Always do what you’re going to say you’re going to do.” And then you don’t because of life, what’s the next step?

Cathi: Well, I guess you apologize. Definitely don’t let it fester, just be accountable for that as well, immediately. Remedy it as best you can. Those are hard things to face up to because no one wants to not do what they say they’re going to do.

Tara: Yeah. I think also when you work for yourself, you’re accountable to your client for deadlines and things, but in my experience, deadlines are a little softer when you’re working for yourself with clients because often times, they don’t meet their deadlines of when they’re getting things to you. So I find in the times where something else has gotten in the way and the timeline has changed. First of all, clients aren’t sitting usually on the edge of their seat waiting for the design step that they haven’t put it on their calendar. So if you say, “Gosh, my week went crazy and I can’t get you that until next week.” That you’re not necessarily not doing it but you’re not doing it on time perhaps. It’s not as big of a deal as when perhaps you’re working through somebody else and they’re accountable to their client. Does that make sense?

Cathi: Yeah. My clients are waiting on the edge of their seats with their designs.

Tara: They are?

Cathi: Oh, yes. [laughs] And they pretty much always give me content on time. No, I lied about that. That’s not true at all. [laughter] But I think that– I learned this from collaborating with Jackie D’Elia, she sends a status update even if she didn’t get as far into the progress or far into the task as she thought, I’ve got a status update and I can take that to the client and let them know we’re progressing, this is where we’re at, and they really appreciate that. Even if you didn’t get it done as far as you thought you would be able to.

Liam: It comes back to that communication, doesn’t it?

Cathi: Yeah, everything seems to circle back to that. And when you work with friends– I have a client, I have a business partner– my studio, we do web design and graphic design and branding, but I also have a new business called Dots With Apps where we do apps for orthodontic practices using WordPress as a base. My partner’s an orthodontist and she’s a friend. We’re friends, we’re business partners, I’ve done her website for a practice and all this stuff. Now we’re in business together. We have to communicate five times better and as frequently as I would with a normal client or a partner, because we’re friends.

Liam: Absolutely. That’s a challenge. Communicating can be hard. Little things fest internally and then we, “Ah, I’m not going to bring that up to him.” And then eventually they don’t deserve to know it or– that’s a real challenge. This is a topic that I think could go on for hours. But alas, we are sadly, I’m afraid, out of time. Cathi, before we say goodbye to you, would you please let everyone know where they can find you online?

Cathi: Sure. I can be found on Twitter at @bethebreeze and my website Canddstudios.com.

Tara: Thanks so much for being here, Cathi.

Cathi: Thank you. Thanks for having me.

Liam: Thanks for joining us, it was an absolute pleasure. Bye-bye.

Tara: Bye.

Tara: If you like what we’re doing here – meeting new people in our WordPress community – we invite you to tell others about it. We’re on iTunes and at hallwaychats-staging.ulpgsyz6-liquidwebsites.com.

Liam: Better yet, ask your WordPress friends and colleagues to join us on the show. Encourage them to complete the “Be on the show” form on our site, to tell us about themselves.

Tara: If you like what we’re doing here – meeting new people in our WordPress community – we invite you to tell others about it. We’re on iTunes and at hallwaychats-staging.ulpgsyz6-liquidwebsites.com.

Liam: Better yet, ask your WordPress friends and colleagues to join us on the show. Encourage them to complete the “Be on the show” form on our site, to tell us about themselves.