Graphic designer and calligrapher Katie Upton was laid off, so she turned what had been a side hustle into a full-time career. Here’s how she built her small business.

As told to Brandi Diaz

I was in advertising for five years. It was a great experience and I learned a lot—I probably would not be able to do what I’m doing now had I not had that experience. I was always the graphic designer in advertising who was super artsy. I was always the person they’d go to for the hand-drawn type or really cool typography.

I always had in the back of my head I’m not going to do this forever, thinking how can I make typography my every day job?

I was living in Connecticut while I was in advertising and started taking calligraphy courses in New York City at the School of Visual Arts. It was awesome and cemented that this is exactly what I want to do.


I started using the calligraphy in my job, day to day, and tried to fit it in more on the side. People would hire me to do the calligraphy on their wedding envelopes and invitations, and I thought I really love this, I really want to do this. I kept on working in advertising, though, and had them transfer me up to the office in Boston to be closer to family.

So we moved up here, and I worked for the same company for about a year, and then I got laid off. And had I not been laid off, I would not have done this.

I was comfortable: I was getting a salary and health benefits and 401k. After I got laid off, I interviewed and tried to do something else in house, but nothing worked out. I thought this is a sign, it’s not working out for a reason. And at that point I was thinking if I’m going to have a full-time job, I want something that’s meaningful to me. Now is the time.


I’d started picking up more freelance and calligraphy work, and it honestly just took off. Now I don’t have time to even take on a full-time job, if one were to come along.

I went to social media to build the business. I do a post a day. I started doing positive, optimistic quotes. Some are silly, but I wanted to focus on things that make me happy. People started to respond. Then the weddings started picking up. Most of my audience is from social and word of mouth.

I create a lot just for me, but then also sell it on Etsy. Etsy is such passive income: I made this for me, but why wouldn’t I put it up? I also do SoWa and other markets. I do get custom requests, but I tend to do quotes that I’m inspired by, I hang them up in my house. That’s how I’ve always felt about calligraphy: It’s an escape from negativity, but it’s also become my craft. It’s making money doing what you love, which is great.


I’m always working on my own art, but I also regularly take freelance jobs, which are the big money makers. Assignments can be PowerPoint templates, brochures, things I can do easily and make decent money. I do that to pay for health insurance.

With all the calligraphy, that’s on my time, that’s what I can do when I want. And because weddings are so spaced out, I can work with brides months in advance and can judge my time based on scheduling. Every day is full! I’m still working 9 to 7. It’s not by any means any less busy from when I was in advertising, but I’m happy to get up in the morning and start working, rather than dreading going into an office.

I’m super organized, but I tend not to make a schedule. I do have a routine: get up, walk the dog, make breakfast, start working. Every project has its own timeline, I tend to check day by day as I finish projects: I’ll schedule, reschedule, or move things around. In my head, I know how long it’s going to take me to do something. I’m my own project manager, which is also stressful, but I don’t mind it.


I try to do one conference a year, such as the Yellow Conference in L.A. It was awesome because it was all focused on positivity and being an entrepreneur, but using your skill for good. I try to do design and calligraphy workshops. I like learning from other calligraphers, because everyone is different. I try to keep in touch with everyone who has taught me something—former professors, bosses, networking contacts—because you’ll never know when you’ll need them.

For those hoping to make a living through your art: Just do it. I honestly wouldn’t have done it if I wasn’t laid off. You get so comfortable that you have to push yourself to take the leap of faith and do it; you know it will be hard at first, but it’s worth it. Always work toward it, but it may take awhile.

Most of the hurdles are finance-related: I have jobs lined up to a certain point, but there are gaps. I try to save as much as possible. I have a budget and my husband has a full-time job; he’s been a godsend to help support our lifestyle. But our lifestyle has drastically changed. I used to spend money on lunch out every day and Starbucks every morning and we’d go out all the time. I feel like I’m still spending that money, but instead I’m spending it to grow my business and invest in myself.

On the tax side of it, I’m not an accountant, and every project is different for me, so that makes it hard. With taxes and the business side, I just want to understand it better, and feel comfortable doing it and doing it correctly.

I want to keep building what I have. Every day I just experiment. I try something new every day.

Follow Katie Upton on Instagram @katieelizabethlettering.


Brandi Diaz is a writer, photographer, and filmmaker based in Boston.

Photos courtesy Hannah Cohen

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