We’re excited to introduce you to the always interesting and insightful Carissa Flores. We hope you’ll enjoy our conversation with Carissa below.
Carissa, thanks for joining us, excited to have you contributing your stories and insights. Can you recount a story of an unexpected problem you’ve faced along the way?
I started pursuing my small business at the end of 2019. Energized by doing the calligraphy for my own wedding, I created some envelope and seating chart samples and asked friends if I could do their wedding calligraphy. I finally got my first wedding envelope client whose wedding was scheduled for spring 2020, and in early 2020, a few more signage and envelope orders trickled in.
But I started to realize something was changing when the quarantine began. One after another, weddings were postponed, then canceled, including my client’s. My hopes of starting my business with the 2020 wedding season were shattered.
Still filled with energy and inspiration for calligraphy, I shifted my focus. I created signs for drive-by graduation and birthday celebrations. I sold hand-lettered decals for storefronts with messages about wearing masks and social distancing. I used my platform to share hand-lettered messages about racial justice. I designed literary-themed postcards and mailed them to my high school English students so they wouldn’t feel so alone during my Zoom classes.
I even created digital game boards that I called “Takeout Bingo,” encouraging neighbors to visit the local restaurants in the Bay Area that were struggling and post about it. This activity helped my husband and I to meet local restaurant owners and feel more connected to our community too!
Fast forward to 2023, and my business now does consist of a lot of wedding calligraphy like I once dreamed, in addition to teaching Sip & Script modern calligraphy workshops. But when I look back on everything that I learned and all the creative outlets I found during COVID, I’m glad my business didn’t go according to plan. Because my plans got derailed, I grew closer to my community and learned to do so much more with my creative skills.

Carissa, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
For over 15 years, I have been practicing calligraphy, the art of writing beautifully. I serve wedding and business clients in the Bay Area, California, and my passion is adding a hand-lettered touch to every event. From show-stopping seating charts to your loved ones’ names written beautifully on place cards, I believe hand-lettered details make all the difference for events.
In addition to day-of wedding items, I am available for live calligraphy and engraving. I love doing calligraphy in front of people so that they can see the careful artistry that goes into my work, and they can have their items customized in any way they want! I could engrave wine glasses or bottles, for example, or create gift tags for the items your customers are buying for the holidays.
You can also find me teaching calligraphy workshops at local restaurants and shops in the evenings. These Sip & Script classes are a laid-back environment where I share everything you need to make calligraphy a rewarding hobby or business. I partner with amazing businesses and love sharing my passion with beginners.

Is there something you think non-creatives will struggle to understand about your journey as a creative?
My field of calligraphy is a little bit niche: it’s not quite stationery, and it’s not graphic design, but it’s somewhere in that neighborhood, mixed with event planning and art. It’s not a requirement for a wedding or event, like catering or a venue, so often clients only choose it when they have room in the budget. Wedding calligraphy is so niche that major industry websites like The Knot don’t have a category on their website for it, even though it is seen at so many weddings.
For that reason, it’s challenging for the general public to understand how to value the work of calligraphers–in other words, what to expect with pricing. Our rates are often calculated based on the materials plus the time. Because we set our own prices, we have to decide what an hour of our time is worth, keeping in mind that it is skilled labor based on years of practice, and of course, we often become more efficient with our time as we get more skilled.
It’s also so important for calligraphers not to undercut each other and devalue the work as a whole, so clients can trust that my rates, and the rates of calligraphers like me, are based on the market rate for this type of work.
And ultimately, how can you put a price on something that is created by hand? We’re usually not using fonts or stencils, either — this is work produced with my own hand and my hours of loving work. We all hope you’ll see that the thoughtfulness and care reflected in our calligraphy is worth the prices.

Looking back, are there any resources you wish you knew about earlier in your creative journey?
I would encourage my beginner self to seek mentorship and calligrapher-specific resources sooner. I’m the stubborn type, so I’d rather learn things the hard way than ask for expert advice. Once I started taking courses, following other calligraphers, and asking questions in online forums, I realized other people were freely offering information that I had struggled and sometimes failed to figure out through trial and error.
Now that I’m open to learning from others, I have benefited so much from business mentorship and online courses such as the Pro Wedding Calligrapher course by Shaochen at @monsteragold, business resources from Marie at @maidenseptember, calligraphy tips Becca from @thehappyevercrafter, and so much more. At the very beginning of my calligraphy journey, I took a Skillshare class from Bryn at @paperfinger that made me absolutely fall in love with the art form, and my first time meeting up with other calligraphers in real life was at a calligraphy shop in San Jose that was run by Queeny at @travelingcalligrapher. And I finally felt like I was “official” when I bought Molly Suber Thorpe’s book, The Calligrapher’s Business Handbook.
I would be lost without the community of calligraphers I have found online! I am also so grateful for incredible collaboration and community with my fellow Sip & Script instructors across the country, and I belong to a few Facebook groups where calligraphers and lettering artists can ask questions and seek insight.
Creative types sometimes think that we have to have original ideas 100% of the time, and wow — that couldn’t be further from the truth. In the calligraphy world, we often use the phrase “community over competition,” and I’m grateful that I’ve found my way into this community.

Contact Info:
- Website: www.dosfloresdesigns.com
- Instagram: @dosfloresdesigns
- Facebook: https://www.facebook.com/dosfloresdesigns/
- The Knot: https://www.theknot.com/marketplace/dos-flores-designs-fremont-ca-2042615

