Lisa, what have you been working on since we interviewed you in January 2012?
Lisa: The last three years have been enormously productive and fruitful. In 2012, I began making a shift towards doing more illustration and less fine art—not because I was no longer happy painting and having gallery shows, but because I ended up being offered more illustration and book opportunities. The pendulum is constantly swinging back and forth, though, so now I’m trying to get back into making more personal fine art, which has recently taken the direction of abstract paintings.
In August 2015, I did a month-long artist residency at Drop Forge & Tool in Hudson, New York. Most of the illustration work I do is for clients, so it’s not necessarily work that I invent on my own. I’m usually working with an art director, editor, or publishing company—and sometimes all three—who direct everything. During my residency, I was able to explore new materials and paint and draw new personal work.
Tell us more about Fortune Favors the Brave?
Lisa: It’s the second of two hand-lettered quote books I’ve published. In 2014, I put out a book called Whatever You Are, Be A Good One, which was a collection of hand-lettered quotations that sprang from a personal project I did on my blog in 2012 called 365 Days of Hand Lettering. I wanted to become a better hand-letterer, so every day for a year I hand-lettered something and posted it on my blog, and what I ended up doing a lot of were my favorite quotations. Chronicle Books—a publisher I had worked with before—approached me and said they wanted to make some of the hand-lettered quotations into a book. It has done very well, so before much time passed they said, “We want to make another one!” Fortune Favors the Brave is a very similar book: it features 100 quotations in the same size and format, but they’re all focused on courage, bravery, and being yourself.
[to Lisa and Clay] The two of you married in June 2013 and recently took the leap to work together. What is it like to be an entrepreneurial couple, and what led to that decision?
Lisa: Clay and I only started working together as business partners in April of this year, but we started talking about working together in 2014. I had become so busy that it wasn’t sustainable for me to do everything. I hired assistants from time to time, but I needed someone with more developed skills beyond helping me answer emails or ship orders. I needed someone to help me manage my day-to-day business operations and contract negotiations. Every time I thought about what I needed, I thought, “Clay has all those skills!” (laughing) I decided to just ask her what it’d be like to work together.
Clay: We went out to lunch on New Year’s Day 2014 and talked about what it would be like to work together. It wasn’t a foreign concept to us because we have many friends who are creative entrepreneurial couples, but I hadn’t pictured that for myself. At that point, I’d been working for someone else for almost 20 years: I’ve worked at agencies and publishers and, most recently, as the Director of Marketing for California College of the Arts in San Francisco. I had always been in an office working for an employer, so the idea of working with Lisa was exciting, but also terrifying.
I spent the entire year of 2014 becoming comfortable enough with the idea until I felt ready to tell my friends and family and verbalize the shift that Lisa and I were making. And it was a big shift: not only were we going to be working together, but we also decided to uproot ourselves and move to another city.
Lisa: Clay and I decided to move from the Bay Area, where we had both lived for many years, to Portland, Oregon, earlier this year. We wanted to move somewhere a little slower-paced and more affordable, but still have a great creative community. Moving to Portland made it feel more feasible for Clay and I to join forces around my business.
Clay: It was a difficult transition for me. I think it was easier for Lisa: her career didn’t really change and her family lives in Portland. All of that being said, when we finally landed in Portland, I felt excited and jumped right in.
I already knew Lisa’s business really well, so it was more about getting up to speed on a million different platforms, projects, and clients. I’m still learning every day, but luckily I’ve put some good systems into place.
In addition to setting up systems for Lisa’s business, we also spent a lot of time putting ground rules and norms into place before we jumped into the endeavor of working together. Because we’re also married, we wanted to make sure that we had some specific agreements and ideas about how we were going to co-exist all day, every day, both inside and outside of work time.
Lisa: (buzzer sounds) What is that? Oh, Clay is baking something. (laughing)
(Clay leaves to check on the oven)
Lisa: It’s been great, because there were certain aspects of my business that I didn’t trust just anyone to work on. Clay manages and negotiates all of my contracts with illustration and licensing clients. She brokers relationships for me, helps me manage my schedule, and thinks strategically about new projects and potential future endeavors. Plus, we already share expenses, so that made the accounting easier. She already knew my business so well, and I trust her, so it wasn’t like I had to train someone from the ground up. It was kind of a perfect solution to my feeling overwhelmed!
That said, there have been challenges. For instance, Clay has never worked from home before, and I think that has taken some getting used to. How does she get up every day and feel like a real, professional person even though she’s not leaving the house some days?
Clay: (returning from the kitchen) Yeah, working from home was a new challenge for me. I’ve embraced it now, but it definitely wasn’t as great as I thought it would be at first. Working from home sounds so comfy, but it can also feel isolating. We are still working on building out our studio and office space, so in the meantime I’ve explored different places to work around our home and tried working at a friend’s office or coworking spaces. It will be great when the studio is finished and we hire another person.
Lisa: The new studio is on our property, but it’s detached from the house: it’s great because it’s right there, but we actually have to walk to it! In the meantime, until the studio is finished, we’ve been working in our home, which makes it hard to separate home life from work life. I work at the dining room table while Clay mostly works upstairs in the guest room, so we’re making do for now.
Clay: One thing I’m still getting used to is having a new routine. I used to wake up in the morning and go to the gym and have a commute and drink coffee and chat with coworkers. That doesn’t exist anymore, so now I have a lot of those conversations online or over the phone. Lisa and I are doing a good job switching into work mode around 8:30 or 9am. Then we stop for lunch—and, obviously, sometimes we bake. (laughing)
Lisa: Something that is just as important is stopping at 5:30 or 6pm and saying, “Okay, work is over, and now we’re going to be a married couple.” Then we’ll watch TV or read books or go see a movie or have dinner with friends and not talk about work. You have to make time for both, and that’s been challenging: we’ve pushed each other back and forth about it.
It can be hard to stop working when you love what you do.
Lisa: Right. Sometimes we’ll be out to dinner after a long day and one of us will ask the other, “Is it okay if I just ask you one question about work?” Or, “Can we talk about what happened today? Can we process it?”
Clay: We do leave room for that. Sometimes you can’t avoid it!
Lisa: We also make an effort to create a separation between work and the rest of our lives, which are fortunately rich with other interests. We’re both athletic and love spending time outdoors, which is part of why we moved to Portland. We want to be able to have friends over and pursue our interests outside of work. That’s an important part of our relationship; we make sure that we still have romance.
What are you working on now, and what types of projects do you have coming up in the future?
Lisa: We’re working on a couple different projects right now, one of which is developing a new online class. Right now I teach a lot of online classes through various platforms like CreativeLive, Skillshare, and Creativebug. Those platforms are great, and I love working with them, but I also wanted to develop and produce my own three-day intensive online class, which I will offer directly to my followers. The class we’re developing will launch in January, and it’s called I Am An Artist: Taking Charge of Your Path to a Thriving Career. There are usually about four or five main problems or fears that hold creatives back from achieving greatness, and this class will be about overcoming those issues—things like developing confidence and voice.
It’s a lot of work to create an online class, especially developing the backend framework, the payment system, video hosting, and live chats. Clay is managing all of that along with a consultant, and I’m developing the content. It’s a huge project, but it’s something we believe could be really great for people.
I am also starting to develop some of my own products. I license my artwork a lot for all kinds of things like wallpaper, fabric, and stationery. I love working with outside companies, but I want to have more control over my own products and sell them myself. It’s a whole different return on investment. I’m starting with a 2016 calendar, limited-edition prints, tote bags, and then potentially developing other items.
As I mentioned, something I’m working on is getting back into fine art and making and selling original paintings. I get so much joy out of that, and I want to give people the opportunity to buy original works, so for the last year I’ve been working with a gallery in New York called Uprise, which sells my fine art.
Clay: Lisa also has another book, The Joy of Swimming, coming out next May with Chronicle Books.
Lisa: Yeah! I’m a lifelong swimmer, so it’s a book I wrote about all things swimming-related. There are essays and profiles of swimmers as well as bits of swimming history and culture, but also lots of hand-lettering and illustration. Apart from that, I’m also on the verge of signing a contract for another book, which I will write next year.
“We also make an effort to create a separation between work and the rest of our lives, which are fortunately rich with other interests…We want to be able to have friends over and pursue our interests outside of work.” /Lisa
What advice would you give to another couple who might be considering working together?
Lisa: Before you start working together, spend some time thinking through how you want to work together, and then hold yourself to all the agreements you make.
Something Clay and I did that was really helpful was holding a day-long retreat. About two weeks before we moved to Portland, we invited a business coach I had previously worked with to serve as a facilitator. We asked her to sit with us all day in order to help us hash out a lot of different considerations: What agreements should we make about working together? What were our different working styles, and how could we respect those in each other? We had been in a romantic relationship for seven years, but we rarely saw each other when we were working because she was at an office and I was in my studio or at home. I didn’t know how Clay worked—did she like talking all day, or was she the kind of person who wanted to put her headphones on and be left alone? This was a whole new world for us, so we talked about all of that during the retreat. We talked about how we were going to bring positivity to our working relationship and to the business, and we talked about financial goals. We made lists of agreements about how we would treat each other and planned out how we’d communicate when we hit sticky points—essentially preparing for worst-case scenarios.
Something else that was helpful was establishing what our individual roles would be in the business—what Clay was going to be responsible for versus what I was responsible for. I was used to doing everything myself, and I knew Clay was going to be taking some responsibilities off of my plate, but there were some things that I didn’t want to let go of.
Clay: It was extremely helpful to establish who was responsible for what, and we actually typed out job descriptions.
Something else to consider as a couple is whether you are starting a business together or if one person is joining the other’s pre-existing business. In our case, I joined an existing business. In many ways, that was much easier than if we had started together. Lisa was able to leave big areas open for me to move into and own. If a couple is joining forces as opposed to starting from scratch, giving the new person room and a sense of ownership makes a huge difference. Today, after five or six months, I definitely feel like a part-owner of the business.
Lisa: (to Clay) But you didn’t necessarily feel that way in the beginning.
Clay: (to Lisa) No, not in the beginning. At first I felt like I was working for you, but now I feel like I’m working alongside you.
Lisa: I realize that part of the reason everything has happened for us the way it has is because we happen to be two women, particularly two women who like to process things by talking. (laughing) So we’re always checking in by asking each other, “How’s this working for you?” Or, “Are you feeling okay?” It’s important to me that Clay is happy. I would much rather have her be happy without being my business partner than to be my business partner and be unhappy. It’s important to me that she feels excited and motivated every day by what she’s doing. Every day, we process how that’s going and what we can do better. Having open communication and being willing to make changes to what we’ve agreed on is of the utmost importance.
Clay: You need to have the willingness to assess, step back, and renegotiate if things aren’t going as planned. You can go into something with certain intentions, but as all entrepreneurs know, your first idea isn’t always the one you end up going with. You need to make adjustments along the way.
Would you say that moving from San Francisco to Portland in order to work together was the biggest risk you’ve taken in the last three years?
Lisa: Absolutely. It was a huge financial risk for both of us to rely on my income alone. I’m a working artist, so my workload ebbs and flows to a certain extent. When you’re self-employed, you have to have an enormous amount of trust that the universe is going to take care of you no matter what. I knew that my business could support both of us: in fact, I knew having another great mind in my business was going to make it more robust and increase my opportunities.
I feel a responsibility to Clay to make sure that our needs are taken care of; but by and large, more of the risk was felt by Clay. I have family in Portland, so moving here felt a little easier for me than it would have if we had moved to Georgia, where she’s from. I had to bear that burden with her, even though I kept saying, “It’s totally going to be fine!” In my mind, I wasn’t as scared, but I knew she was, so I needed to be there for her.
Clay: The biggest risk I’ve taken was moving from Georgia to San Francisco. I was 23, just a few years out of college, with no job, no community, and no family in the Bay Area. That was about 19 years ago, so moving to Portland was my second biggest risk.
How do you feel about taking a risk to move to Portland now that you’ve had time to adjust and settle in?
Clay: Now that we’re here, we’ve gotten into the flow of our work. Lisa was also away in August for her residency, and that gave us a chance to work separately for a while.
Lisa: Actually, my residency came at an interesting time. Being apart was an opportunity for us to assess if this arrangement we’d concocted was really working. I had been planning on doing my residency in New York for almost a year, so it wasn’t like the timing was strategic or anything. We knew being away from each other would help clarify whether we were both happy with how everything was going. It made us realize that we really do enjoy working together. We actually couldn’t wait for me to come back home so we could get back to working together again.
Something else we’ve realized is that Clay needs her own projects. Recently, a couple of our entrepreneurial friends needed help and have hired Clay to work with them on a project—to-project basis. She’s also started freelancing with a focus on marketing and operations, which brings in additional income and feeds her intellectual and social needs outside of my business. She’s become so skilled and efficient with the business that she has time to take on her own clients.
Clay: I’d previously entertained the idea of eventually bringing on additional clients and taking on my own projects. While Lisa was away in New York, I had the space I needed to think that through and see if it’s what I truly wanted. I realized that just like Lisa needs to do her own personal work and things that have nothing to do with me, I also need to go off and have my own experiences and projects. For example, I’m currently involved in a planning committee for a conference happening here in Portland this October called WeMake Celebrates, and I’m handling marketing strategy for two new clients.
It’s great that you two are able to chase separate passions and still build a business together.
Clay: It’s the healthiest option, but it wasn’t necessarily in the original plan.
Lisa: Right. Before Clay came on, my computer files were a mess and aspects of my business weren’t systematized—I mean, it was just terrible. Clay has literally organized my entire business. Because of that, everything is more efficient now, so she doesn’t necessarily need to work 40 hours a week anymore.
Clay: When I first started, we were both working way more than 40 hours a week because there was so much to organize and set up. I said to Lisa, “I don’t understand—how were you doing it all?” And she said, “I wasn’t!” (laughing)
About Lisa & Clay
Entrepreneurial couple, Lisa Congdon and Clay Walsh, are partners in business and life. Best known for her colorful, abstract paintings, patterns, and hand lettering, Lisa is a fine artist and illustrator who has worked for clients like MoMA, Harvard University, and Martha Stewart Living. Her latest of five books, Fortune Favors the Brave, debuted in August. Former Director of Marketing at California College of the Arts and marketing pro for the Gift Division at Chronicle Books, Clay has 20 years of experience working with clients and creative teams. In 2015, she joined Lisa Congdon Art & Illustration as Head of Marketing & Operations. Lisa and Clay live and work in Portland, Oregon.
“You need to have the willingness to assess, step back, and renegotiate if things aren’t going as planned. You can go into something with certain intentions, but as all entrepreneurs know, your first idea isn’t always the one you end up going with.” /Clay