Typism Feature Interview: Kristen De Palma
Jan 19, 2025
Known for her detailed, vintage-inspired lettering, Kristen De Palma creates meaningful artwork for brands, including book covers, packaging, murals, and more.
Kristen has worked with brands such as Adidas, Pepsi, and Jagermeister and recently launched her first lettering course on Skillshare. Her award-winning line of floriography seed packets is sold across North America and beyond.
What initially inspired you to start lettering, and how did you discover your passion for it?
I’ve always been fascinated by lettering of all kinds, even when I used to write notes in elementary school and would practice using different fonts. I signed up for a few online courses but never found the motivation to start or complete them.
Finally, a local calligraphy workshop was being hosted, so I signed up. That short workshop was all I needed to fall completely in love with drawing letters. I became obsessed and practised every single day after the workshop, and it’s now been almost 10 years!
Can you share a pivotal moment in your lettering journey that significantly influenced your artistic style?
Yes, and it’s actually slightly embarrassing. Early on, I really liked this particular lettering artist’s style that I found on Instagram, who was really established in their career and had a lot of followers. I was brand new to lettering at the time, only a couple of months in and had maybe 30 followers on Instagram, but apparently, I was taking too much inspiration from that person because she reached out to me directly to tell me to stop ‘copying her style basically’.
I was SO embarrassed and completely distraught at finally getting to engage with my lettering hero, and this was the interaction we had.
It taught me two really important lessons that have shaped my career:
1) Get your inspiration off Instagram! I immediately unfollowed this artist and started looking elsewhere for inspiration to develop my style. I dove deep into vintage lettering in antique shops and practised my lettering without any influence at all. This helped shape my style in my own unique way.
Rather than taking this experience as a discouraging thing that would deter me from developing, I used it to excel in the other direction.
2) Be the artist you’d want to meet. After reflecting on that experience, I decided that I would never want to be an artist that tears people down or discourages them from practising or feeling inspired in the way this artist did to me really early on in my practice. There’s going to be people that ‘copy’ your style, inevitably—that’s part of the deal when you share your work on a public platform.
Rather than operate from a mindset of scarcity and always looking over your shoulder, there’s a different way to approach it. Instead, you can choose to build others up and be confident in your own style. That’s the path I’ve chosen to take.
Who are some of your biggest influences in the lettering community, and how have they shaped your work?
LOL, see above! I won’t mention who the person was. In terms of positive influence, though, there are a few artists who have really helped shape my journey as a lettering artist.
Of course, the queen of lettering, Jessica Hische, is a professional yet down-to-earth person, and I really admire how willing she is to share her knowledge with others when it comes to pricing, etc. Taking her ‘dark art of pricing’ course in my first year of doing this full-time helped give me the confidence to charge my worth.
Lauren Hom’s ‘HOMwork’ challenge was super inspiring to me as I was building my practice. It kept me motivated to create and share new work. She is also such a positive example of someone who chooses to build others up and helps to create community over competition. There are many others, too, but these two women stand out the most to me!
What advice would you give to aspiring lettering artists who are just starting and seeking inspiration?
In addition to my answer in #2 (get your inspiration off of Instagram!), I always remember something that sign painter Mike Meyer told the class during a course that I took back in 2018—he said that to succeed as a sign painter, it takes three things: desire, dedication and discipline. I would say that the same recipe applies to hand lettering or truly building any new skill set.
There is no secret trick to becoming great; it just takes time and practice, so you really have to want it.
How do you stay inspired and motivated when facing creative blocks or challenges in your work?
I’m never waiting for inspiration to strike. I’m consistently drawing every single day, no matter whether I feel motivated or not. In that way, it’s become a habit rather than something I need to feel a certain way in order to do.
If I’m ever feeling stuck on a particular project or like I need a certain spark, I always believe in changing my scenery. I’ll go antique shopping, for a walk, to a museum, etc., in order to see and experience new things. That always seems to work for refilling my inspiration bank!
What are some essential techniques or skills that you believe every lettering artist should master?
I think that lettering artists should have a solid foundation of understanding letterforms and learn to draft letters with pencil and paper before beginning to master digital lettering. I believe there’s so much value in learning the traditional way, with no shortcuts or special brushes, so you can appreciate the craftsmanship and, as Picasso said, ‘learn the rules like a pro so you can break them like an artist’.
Can you describe your process for developing and refining a new lettering style or project?
I love to look at references from a variety of sources to inspire a strong direction—that might include reference books I have on hand, previous work I’ve done, Pinterest browsing, and most often, heading to an antique shop to peruse old tins, packaging and ephemera.
Once I have a sense of what visual direction I’d like to head in, then I’ll begin sketching on my iPad. I always start with loose sketches, exploring many different layout options before landing on one that works best.
Refining with details and landing on a colour palette is usually where I spend most of my time, and that’s where I really zone out and enjoy the process.
What resources or tools have been most helpful in enhancing your lettering skills?
I started with pencil and paper, but the iPad + Procreate has definitely been the level-up tool for my skill set that really allowed me to translate my work to commercial projects. I remember getting my first magazine commission, and I was literally scanning an ink drawing and trying to clean it up in Photoshop—never again!
That said, Procreate was a learning curve for me—it took me about a year of practice before I was more comfortable working digitally than on paper.
How do you approach continuous learning and skill improvement in your lettering practice?
I’m always taking in new information and inspiration, remaining open to growth. I think a lot of it relates to your mindset—if you think you know everything and are the best, then you’re not growing. I’m forever open to getting better and exploring, and I’ve always been really interested in learning opportunities in my corporate career as well as my artistic career.
Everyone has a unique teaching style, and I have never not taken at least one thing away from each class or talk that I invest time into.
Can you share an example of a project or challenge that pushed you to grow as a lettering artist?
Nearly every project has something new to take away from it, but over the last year, there have been a few client projects that really pushed me to evolve the illustration side of my artwork. I usually have shied away from drawing anything other than letters and flourishes, but I’ve absolutely loved exploring more elaborate illustrations alongside my letters!
How did you transition from lettering as a hobby to making it a sustainable business?
It certainly wasn’t overnight. I had been lettering as a hobby for about seven years before I turned it into a full-time career.
Over that time, I had built up a good list of clients and a solid social media following, and I was getting progressively busier with projects.
Eventually, I started thinking, ‘what type of success would I see if I started putting ALL my energy into this instead of just 10%?’
In April 2021, I started putting everything I was making from my lettering commissions aside in a savings account and decided to put my notice in that fall. I tried to forecast how much income I could make from this, but I was severely undercharging at the time, so I wasn’t sure how feasible it would be. Once I started charging appropriately, I was able to make it a sustainable career for myself.
What strategies have you found effective in promoting and monetising your lettering work?
I love using my marketing background to speak my clients’ language and connect my artwork to their strategic priorities. I also always think from the customer’s perspective, which has really helped me land proposals!
Can you discuss the role of community and networking in building your lettering business?
After I left my corporate career to pursue lettering full-time, I was really nervous that I wouldn’t have a community around me and people to bounce ideas off like I had in my office job.
I couldn’t have been more wrong because the lettering community is amazing! I have really enjoyed getting to know and collaborating with fellow artists in the lettering and art community—it’s so helpful to validate and discuss what you’re going through, like pricing or client challenges.
Working together rather than working from a scarcity mindset helps to strengthen the overall industry.
What advice do you have for lettering artists looking to diversify their income streams beyond freelancing?
I’d suggest starting small and testing—that’s a real benefit of being a small business owner, which is that you can be nimble.
For example, I was interested in launching my own product line of seed packets—but before committing to thousands of items in inventory, I started with just a small run of a few of each design and tested them locally in my community.
Once I got some validation that people were digging these, I could then commit to scaling up and ordering more.
I think this can apply to many different revenue streams—it’s riskier to go all-in in one direction, like art licensing, only to discover later that you don’t really enjoy it, or your designs maybe aren’t working in that stream.
Start small, test, measure, refine, and keep building—and be ready to switch directions if it’s simply not working!
Secondly, pay attention to what’s working already and comes naturally for you. It’s easy to get distracted by something shiny and new, but you might already have a revenue stream that you haven’t made the most of exploring yet.
For example, maybe a lot of your client work involves requests for book covers. Maybe it’s time to start thinking about working on your own book, leading a workshop, or creating a digital product all about book cover design! Or, maybe you have a lot of unused client project designs that aren’t specifically branded—that’s a great start for an art licensing portfolio.
How do you balance the creative and business aspects of your lettering career?
Because of my 10+ year career in marketing strategy before becoming an artist, a business mindset comes naturally to me. A large part of being creative is problem-solving, which is a lot like business, so they truly go hand in hand for me.
My creative process usually starts with looking at the question of, ‘what problem am I solving?’ and that helps connect the work that I do to a business mindset while I’m creating. Sometimes, the problem is more business-forward, like “we need to get customers to buy more of our product”, and sometimes it’s more creative/art-forward, like “I want to make people feel good”.
What does being part of an online lettering community mean to you, and how has it impacted your journey?
I’m super inspired by the lettering community, and I find it has impacted my journey by making me feel like I’m not alone in this solo business! It’s great to connect with other artists to stay inspired, discuss challenges and share industry knowledge with each other.
Can you share a success story or milestone in your career that you're particularly proud of?
I’m particularly proud of having launched my own line of seed packets through my gifting company, To & From Gift Co. This was an idea that seemed unattainable while I was balancing lettering alongside a corporate career, and I’m so proud that I not only made it happen but now sell my products in retail shops across North America and beyond.
This collection of products is a reflection of something I’m incredibly passionate about, and it really connected and resonated with people, which is such a special accomplishment for me.
What trends do you see emerging in the lettering world, and how are you adapting to them?
Obviously, the evolution and emergence of AI have been hot topics for the artist community in recent years, and I think, ultimately, it will only lead to more of an appreciation for human-created art. I’m trying to find ways to use AI as a helpful tool rather than being scared of it. Things like chatGPT can actually be really helpful when drafting client emails.
How do you manage your time and stay organised with multiple projects and commitments?
This is a constant challenge! Work ebbs and flows, so sometimes I am completely overwhelmed, and other times it feels totally manageable. I am a naturally organized person, so I don’t ever miss deadlines, but I definitely experience burnout at times. I’m always trying to remember that rest is productive!
To stay organized, I always create project timelines within my client contracts and add all the key dates to my Google tasks. This keeps me on track and accountable.
What future goals or projects do you have for your lettering career, and how are you planning to achieve them?
Looking forward, it’s a goal of mine to continue building my portfolio of art licensing & teaching products. Because I won’t really want to be up on a boom lift painting a mural when I’m 50 (because my back already hurts), I want to be able to rely on having some passive income streams. I’m working on my next Skillshare class at the moment, with plans for many more to come, and I’m always creating new designs to add to my art licensing portfolio.
We hope you enjoyed our feature interview with Typism 100 member Kristen De Palma.
For more of her work, visit Kristen’s website or follow her on Instagram @kdpletters
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