From Water Bills to World-Class Typefaces: Jen Wagner’s Rise in the World of Font Design

Jen Wagner shares her journey from aspiring orthopedic surgeon to powerhouse type designer is a testament to the power of reinvention. In this episode, Jen shares how a series of unexpected life changes—culminating in a leap of faith to go full-time freelance—led her to create a thriving font design business. Learn how her goal to “just pay the water bill” evolved into a full-scale creative venture and hear how her strategic focus on output, simplicity, and persistence led her to dominate the design world. Whether you’re looking to start your own business or elevate your creative work, Jen’s journey is a must-listen for every female entrepreneur ready to embrace both failure and success.

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Press play for the full interview or keep reading below!

• [00:00]: Introduction to Jen Wagner and Her Journey
• [03:13]: From Medicine to Design: A Career Shift
• [06:07]: The Struggles of Freelancing and Finding Direction
• [08:54]: Discovering Typography and Font Design
• [11:56]: Setting Goals and Finding Success in Type Design
• [15:12]: The Importance of Output and Practice
• [17:53]: Education and Growth in Type Design
• [20:53]: Transitioning to a Full-Time Type Designer
• [23:55]: Navigating Pricing and Market Positioning
• [26:59]: Building a Business and E-commerce Strategy
• [30:05]: The Evolution of Jen’s Business Model
• [32:59]: Final Thoughts and Advice for Aspiring Creatives
• [37:07]: Finding Permission to Change
• [39:55]: Navigating Business and Family Priorities
• [44:44]: The Balance Between Goals and Natural Flow
• [46:37]: Trial and Error in Licensing and Pricing
• [51:09]: Conversations Around Money and Value
• [58:40]: Celebrating Success and Imposter Syndrome
• [01:00:06]: Embracing the Journey of Entrepreneurship

 

 

 

How Jen Wagner Gravitated Toward Design Over Sports Therapy

From the time I was in eighth grade, I was dead set on becoming an orthopedic surgeon. I wanted to go into sports therapy. We were living in Denver at the time, so my dream was to be an orthopedic surgeon in Vail, working with athletes. I thought, “This is it — I love sports, I love medicine. This will be perfect.”

Then, sophomore year, I took a biology class and realized — I hated it.

Around that same time, my mom — who had us young — decided to go back to college while we were in high school. She studied medicine and eventually became a nurse practitioner. So while I was in high school, she was in college, and I got to watch her pursue medicine. Between seeing her journey and my own experience in that biology class, I realized I needed a career shift. I just didn’t want to go down that path anymore.

From there, things got a bit wishy-washy. I’ve always been a creative person — drawing, painting, calligraphy, photography, design — those were always part of me. So I started doing design just for fun. Funny enough, I even traded design work for the National Honor Society Club at school in exchange for them checking off my attendance when I wasn’t there. I was bartering in high school — “If you say I was in NHS, I’ll give you some t-shirt designs.

So yeah, design was something I naturally gravitated toward. Creating beautiful things has always felt like a core part of who I am, and design became the way I expressed that. I ended up doing it for a long time.

 

A Non-Linear Career Path

I was so unsure of what I wanted to do with my life that I decided to study business and marketing. I really enjoyed those topics. I’d always been entrepreneurial — even in elementary school, I was selling lanyards. In high school, we bought screen-printing equipment and set it up in the garage, so I ran a small screen-printing business during my senior year and into my freshman year of college. I also did photography and basically tried everything I could get my hands on.

Eventually, I went to CU and got my degree in marketing. During that time, I was working full-time at a church as their creative director, which — even though it was technically part-time — was more like 50 hours a week. Life was busy. I graduated from college in 2015 while juggling all of that.

At that point, I was freelancing about 30 hours a week on top of everything else — I was just constantly working. Eventually, I thought, “You know what? I think I can quit my job at the church and go full-time freelance.” Working at a church had never been my dream — it wasn’t my life goal — and I realized I was doing something I didn’t actually want. I was unhappy, so I took a hard look at my life and decided to make a change.

But the day I quit my job at the church, almost all of my freelance work disappeared. I went from 30 hours a week to just five. Within days, I got emails from clients saying, “Sorry, we know we said 20 hours a week, but our budget changed,” or “We can only offer you an admin role,” or “We need to pause projects.” Everything just fell apart all at once.

And then, about a month later, my parents got divorced. A few weeks after that, we experienced a very early miscarriage. It felt like everything in my life was unraveling. We had planned our lives around having dual income, so now we were trying to figure out how to make it all work. We did make it work — but I was deeply stressed.

 

Separating Your Self Worth From Your Income

I grew up tying my self-worth to my income. So when I wasn’t making money, I felt completely worthless — like nothing I did mattered, and neither did I. I was scrambling to find ways to make money. I started an Etsy shop with calligraphy products, did wedding invitations, and tried anything I could — but nothing really stuck. And on top of that, I wasn’t even enjoying any of it.

Eventually, I threw in the towel and started applying for marketing jobs around Denver. I got pretty far with one company — I was three interviews in — but the process was dragging out. Around that same time, the one freelance client I had left said, “Hey, let’s pause our projects until we know whether or not you’re taking this new job.” It made sense, but it left me with nothing to do for about three weeks.

That’s when my husband, who had watched me try and fail for months — eight months at that point — said something that changed everything. He said, “You have three weeks and no obligations. Use this time to make something just because you want to. Don’t worry if it makes money. Don’t worry if you’re good at it. Just make something you’re curious about.”

 

Becoming a Font Designer

So I thought, “Well, I’ve always loved typography and been interested in font design.” I had searched for specific fonts for my own projects and couldn’t find what I was looking for, so I ended up just drawing the letters myself. That got me wondering — “Is there an easy way to turn this into an actual font?”

That’s when a friend told me about a company called Fontself — this was back in 2016 — that had just released a plugin for Adobe Illustrator. It let you drag and drop your alphabet into the plugin, and it would generate a working font file. At the time, there were no online resources or tutorials for learning type design. YouTube was still mostly entertainment — not a place to learn this kind of thing. So I just started experimenting.

I had also recently been accepted to Creative Market, and my original plan was to sell illustrations and lettering there. But I decided to try uploading a few of these fonts instead. Honestly, my goal was modest — I just wanted to make enough to pay the water bill, maybe $40 a month, and treat myself to Chipotle once a week.

That was my dream — “If Creative Market can help me do that passively, I’ll be over the moon.” I’d had zero wins all year, and I just needed something to work.
But that first month, I ended up tripling the income I used to make at the church. It wasn’t a huge amount, but it was enough to feel like, “Okay — this is a real job.”

 

Selling on Creative Market

. Once it was uploaded, it was pretty passive. I knew I didn’t know what I was doing, so my fonts were super simple — all uppercase, numbers, basic punctuation. No kerning, no finessing. It was just… what it was. And I priced them accordingly — $9 to $12.

But because they were so simple, I was able to make three fonts a week and just keep uploading. And honestly, that was such a helpful thing early on — I learned that sometimes repetition is more valuable than quality when you’re just starting out. Every time you start something new, you learn something new. You get faster, better, and you start noticing things you want to do differently.

I think in my first couple of months, I made around 25 fonts. And because I was feeding the Creative Market algorithm so consistently, they were like, “Cool — anything Jen puts out, we’re going to push.” And when you’re uploading three products a week, it kind of looked like I came out of nowhere. And honestly — I kind of did.

 

Setting Simple Goals to Get Started

I think having those goals be so simple and sweet made it low-pressure enough for me to actually enjoy it. If I had gone into it thinking, “I’m going to make this my job,” it would’ve immediately turned into something stressful — just like everything else I’d tried earlier that year. I had started so many different things with that mindset, and none of them were fun.

But because this was just a hobby — something I was curious about — it stayed enjoyable. I remember thinking, “If I can make $60 a month doing this, yeah, that sounds good to me.”

 

The Importance of Outputs

It worked so fast — which I know isn’t typical — but I also think that if you look at the quantity of work, it makes sense. Like, if someone gives themselves a year to make something work and they put out 25 fonts in that year, that’s solid. But I put out 25 fonts in two months. So yeah, it’s not always linear like that, but the numbers help explain it.

The further I get into any creative pursuit, the more I realize how important output is — especially at the beginning. Not for the reasons we usually think, though. It’s not just about volume for volume’s sake — it’s about the training. It’s how you get better. And it also shows other people that you’re serious.

We live in a songwriter and artist town, and I think about it like this: If you’re only releasing two songs a year and only posting about those songs twice, we don’t even really know you’re an artist. But if you’re showing up every week with new content, you’re communicating that you’re taking yourself seriously — and you’re improving every time you create something.

 

Jen Wagner on Setting Pricing in the Beginning Of Business

There were other type designers out there, but they were way better than me at the time. So I just looked at what they were charging and thought, “Cool, I’m going to price under that.” I wanted people to feel like they were getting what they paid for. I didn’t want to deal with people being frustrated by the lower quality — because honestly, I couldn’t fix it at that point.

It’s funny — it’s evolved so much over the years. I feel like it’s only in the last two years that I’ve actually felt like a real type designer. I was totally self-taught until 2020, when I finally got some formal education.

 

Deciding to go “all in” on becoming a type designer

I enrolled in a program at the Cooper Union. I was supposed to go in person — it was a six-week program in New York, and we were going to move there for a couple of months. But then COVID hit and everything shut down. Fortunately, they ended up moving their year-long program online — which they had never done before.

At the time, you could only learn type design in person at six schools in the U.S. — it just wasn’t something you could access easily. I had kind of resigned myself to the idea that I’d just have to stay self-taught and hope I could figure it out on my own. But I hit a wall. I started recognizing, “These things I’m designing don’t look right… but I don’t know how to fix them. And there’s nothing out there to teach me how.”

By that point, I’d already been designing fonts for about three years, and I thought, “Okay, this is my job — I’ve been doing this full-time. Let’s make it official. Let’s get some actual training.”

 

Getting educated on type design

So I applied to both the Cooper Union program in New York and another school in Paris. These days, there are so many great online resources to learn type design, but back then it felt like you either went to one of those programs or you stayed at the same skill level. And for me, that was getting really frustrating.

Once I went through that program, I could see an immediate difference in my work. The quality jumped significantly. A few typefaces in, I remember thinking, “Okay, I think I can actually hang with the bigger foundries now.” I started to feel like I had outgrown Creative Market. It had been a great place to start — and I still think there are amazing foundries on there — but I wanted to take things to the next level.

 

What Business Looks Like Now For Jen Wagner

I mean, it’s all the same — and also totally different. It was always licensing: you’re putting a digital product up on a marketplace, and people pay for a license to use it in whatever context they’re licensing it for.

The pricing has changed significantly since I first started, mainly because the quality of my output has improved. That’s also shifted the types of licenses I’m selling. Now, a few times a year — not constantly, but consistently — bigger corporations come through and say, “Hey, we need a large-scale license.” So the size and scale of the licenses have grown in line with the quality of the work.

After getting an education, I was finally able to create the kind of work I’d always wanted to — which was type families. Before that, I was only doing single-weight, single-style fonts, which created some limitations — not just in design, but in what I could reasonably charge.

It didn’t feel right to be charging $60 or $70 for just a single font. That’s not absurd in the industry, but for me, it felt like too much for what I was offering — especially when it wasn’t a full typeface.

And just to clarify for anyone listening: a font is one specific weight and style — for example, Times New Roman Bold is a font. A typeface is the full family — all the weights, from light through bold, plus italics and everything else

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Increasing Pricing as a Type Designer

So, getting that education allowed me to start creating typefaces, not just individual fonts. That shift gave me the ability to charge more, which was great — because a big goal of mine, in growing what is essentially an e-commerce business, was to increase my average cart value. I started thinking about upsells — whether through licensing or additional font offerings.

When you’re only selling individual fonts, it’s tricky. If a customer doesn’t need six different fonts for their project, they’re not going to buy them. So creating higher-value, higher-priced products was a huge step forward.

And I still find myself going back and forth on this — like, How can I create something higher-ticket, as the buzzword goes, in a way that I feel really good about? Because a core part of my business ethos has always been about making beautiful, quality type accessible to as many people as possible.

I hear people say, “You need to charge more for your typefaces,” and I’m sure I do. But I also remember being a freelancer. I remember how it felt when spending even $50 on a font felt like, “Are you kidding me? I’m only making $200 on this whole project.”

 

Jen Wagner Shares On Keeping Her Typefaces Accessible

And I hope, for anyone listening, that you’re making more than I was back then — that you’re charging more. But I also know how hard and limiting it can feel when you don’t have access to quality type outside of Google Fonts or Adobe Fonts.

The so-called “real” foundries — and I say that with a bit of insecurity, like “I’m not a real foundry… those are the real foundries” — they often price their type families starting at $450 or more, and that’s on the lower end. Then there’s logo licensing, and everyone has different terms. It can get really expensive really quickly.

And while I want to keep pushing forward — to create better and better work, and eventually reach a world-class foundry level — I also want to keep my work accessible. But I don’t know if those two goals can really coexist.

Because to create typefaces at that level, it often takes a team of people, not just me. And it takes time. That means if I’m only putting out one typeface a year instead of six, it naturally has to be priced higher.

That’s the tension — trying to grow your skill and your business, but also loving and caring deeply for the people you’re creating for. And I feel that tension every day.

 

Marketing a Business That Requires Volume

Okay, so my website was honestly an afterthought until 2021. Up until then, I was making all of my income through Creative Market. But over time, as the platform grew and their leadership changed, the company went through a lot of transition — and with that came changes to their commission structure.

It started as a 70/30 split, then shifted to 60/40, and eventually a year later, it became a 50/50 split. I don’t think they can go lower than that, just because of competition from other platforms — but still, a 20% pay cut really hurts. And when you have no control over that, it’s really scary.

So, all the way up until that point — especially around 2018 — things started changing drastically for me, income-wise. That’s actually when I started running ads. And — funny backstory — it was because I hadn’t been saving for taxes. But I realized — I think it was September 2018 or 2019 — that I was going to owe probably $17,000 in taxes that I hadn’t saved for. And I was like, “I don’t know where this money is going to come from… but okay, let’s figure it out. This is the reality, so let’s deal with it.”

 

Diving into the data

That’s when I really dove into the data on Creative Market. They gave us some backend analytics — things like how many likes a product had, how many views it got, etc. And I noticed a pattern: the more likes a product had, the more it sold. There was about a 50% like-to-sale ratio — so if a product had 500 likes, it had sold at least 250 times, often more.

Once I saw that consistency in my data, I started using it to do my own market research. I began looking at other fonts that were selling well and estimating, “Okay, how much money has this font probably made for this creator?” That gave me a better sense of what kinds of fonts I could create that might perform well, since they’d already been market-tested.

Then I realized I could also calculate, in a rough sense, how much money I was making per view on a product. That’s when it clicked — “Oh my gosh, I should be running ads to my Creative Market listings.”

So I started advertising. And when a product performed well, the Creative Market algorithm would push it onto the Popular page, which led to even more organic sales. And I was like, “I figured out the secret!” And it worked really, really well.

But then, of course, our commissions kept getting cut. And eventually, I hit this point where I was like, “This is working really well for me… but I don’t actually own this business.” It was one thing after another. Things were going great, but I still felt totally out of control. And then in 2021, we had our first kid, which made everything feel even more out of control.

 

Choosing a website platform

I realized that if I wanted to take myself seriously and really dignify my work, I needed to own my business. So I started driving my ads to my own website instead of Creative Market.

At first, I was on Squarespace, but they only allowed one type of digital product — I couldn’t offer different license types. So I made the switch to Shopify. That move was stressful and kind of a mess, but I figured it out.

And it actually started doing really well. Before that, my website was only generating maybe 5% of my annual revenue, and then it jumped to 25–30%. But then I started running into limitations with Shopify too — especially around design flexibility, blogging, and SEO. It just wasn’t very friendly for what I needed long-term.

That’s when I realized I probably needed to make the leap to WordPress — which was terrifying. But that’s also when I stumbled on Tonic and bought a Tonic template. I was like, “Okay, I’m going to figure out Showit.”

So in 2022, she helped me move everything from Shopify to WordPress and Showit, and from there, things kind of just blew up. Now, Creative Market only accounts for maybe 30–35% of my monthly revenue — sometimes less — because I’ve really gone all in on my site.

I now have an agency running Pinterest and Facebook ads, and we’re spending a few grand a month on advertising. Every piece of content I put out is focused on driving traffic back to my site. My organic SEO also performs really well.

So yeah — it’s definitely been a journey.

 

Jen Wagner on Changing Priorities During Different Life Seasons

It is tough. I think we once heard someone say that balance isn’t real, but harmony is—and I really believe that. Our seasons of busyness ebb and flow in different areas. Sometimes it’s being really busy with the business, other times it’s being really busy with family, and sometimes it’s just the heaviness of life that keeps you so busy.

I think the other areas of life have to shift and move around to create that harmony. It’s when all the levers are turned up to 10 that things get really difficult—you kind of have to pull the emergency brake and figure out what’s going on.

Hopefully, you have people in your life—whether it’s your partner, friends, or family—who can tell you, “Hey, something’s off, we need a reset.” For me, family is always first. My kids, my husband—those relationships are my priority. That doesn’t mean it’s always perfectly that way. Life gets busy, deadlines creep in.

But having a partner who can pull you out of it and say, “Hey, I get it, but we need you here,” can really help keep things from derailing too much.

 

Setting Goals to Create Harmony

I think the more goals I set, the more I realize I need to stop. I’m naturally a driven person, and I always want things to be their best. But for me, goals can actually be distracting. I spent years getting hyper-focused on income goals—and I didn’t even hit them until I stopped worrying about them.

I just started doing more of the things that came naturally to me and filled gaps I saw in the market. Even before my journey with designing Type, trying to focus on making money and having that be the goal—it just didn’t work. I’ve now hit my income goals without trying. But not because I didn’t do the work—I’ve been doing all the things that actually lead to the goal, instead of just constantly thinking about the goal.

I know that running ads and getting more traffic to my site is going to generate more revenue. That’s a lever I can pull. So then I ask, “What collaborations can I do with creators—like Tonic?” She kind of made Editor’s Note famous. Those kinds of collaborations are so valuable. And now I see that—it’s low effort for me. So it’s like, okay, how do I give creators access to make with my work? That also affects pricing—template licenses aren’t cheap. A lot of creators avoid them because they can be abused, there’s a lot to monitor, and they can get expensive.

But look at what happens—it gets your work out into the world. That generates more revenue in the long run, because people are buying licenses for their social media, and suddenly it’s all circulating back.

 

Talking About Money with Jen Wagner

I think my “problem,” and it’s not really a problem, is that I love beauty and I love quality. And those things can be really expensive.

I want to make a lot of money. And I used to feel so ashamed and embarrassed about that. But it’s not because I want the status—it’s because I want to be able to walk into a vintage store and say, “I want that couch,” and curate beauty without limitations. I want to extend that even into how I live as a person and as a mom—like ordering takeout and not stressing about it, because I know I’ll be a better mom tonight if I don’t have to cook.

Making money has given me the ability to create pockets of beauty in ways that don’t create more stress. And I don’t think you need money to do that, by any means. We’ve been broke, and we were still creating a beautiful life. That’s just your baseline for how you exist—whether your income changes or not.

But I won’t pretend I’ve kept my personal needs small just to feel virtuous about it. And that in itself is a luxury—I know that’s not common. My income has been pretty steady, at least in the sense that it doesn’t dip below a certain level. But having kids has changed the margins a lot. Childcare is expensive, feeding them is expensive—and throwing 30% of that food in the trash is also expensive.

When I was first starting out… I don’t know, it’s hard for me to talk about money without feeling weird about it. I do feel good about my relationship with my business, but I also—yeah, talking about money is a big insecurity of mine. So if I sound like I’m fumbling through it, I am.

I think being someone who’s been on the other side—who’s been broke, and honestly still is in some ways, especially when the things you love don’t necessarily bring in income—I’ve learned that lowering your standard of living in order to do what gives you more life is always worth it. That was true when I had nothing, and it’s still true with a successful business.

And I can also say, on the flip side, that making more money by doing less of what you love is not worth it. That, to me, is what starts to feel like selling out. As soon as I start creating things just to make more money, they don’t work the way I think they will—and I’m miserable. And that extra money? You don’t even feel it.

 

What Jen Wagner is Doing Now

There’s also a resource I kind of just word-vomited into Google Docs and formatted—it’s been super helpful because so many creative business owners really struggle with email marketing. That’s something that significantly changed my business when I started focusing more on my website, and honestly, it’s not as intimidating as people think. So, it’s just an Email Marketing for Creatives guide. It’s a free resource—basically everything I wish I had when I started.

Right now, I feel like I’m in a place where what my business is putting out and what I’m creating visually feels congruent with an older version of me—but not who I am now. And I’m excited to sit down and ask those harder questions again, which I think we need to ask often: What do I want? What do I want to create? How do I want to feel when I put this out into the world? How do I want to feel when I see my work in the wild?

Those shifts can be scary. It’s starting to look like less output, and that’s a little terrifying. But it also feels more aligned with my life, with who I am, and the pace I want to be moving at. And honestly, that approach hasn’t failed me yet—whereas following that red-alert alarm in my brain usually doesn’t go well.

 

More from this Episode

To hear the full story and more about Jen, press play on the player above for the full interview or click here to download the transcript.

 

 RESOURCES MENTIONED:

Email Marketing for Creatives Guide

Font Pairing Guide

Jen Wagner: Hard Deadlines are Toxic Motivators

*Tonic Site Shop

*Showit Website Platform

*Some links above are affiliate links which means I receive a small commission when you choose to purchase through my link. I only recommend tools I love and use myself!

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Jen Wagner

Jen Wagner is an independent Nashville-based type designer known for her candid approach to type design and business. The attention to detail and quality of her typefaces reflect her core belief that beautiful type should be available to as many creatives as possible. With nearly a decade of experience, she has cultivated a reputation for crafting obsession-worthy typefaces that resonate deeply with designers of all kinds and skill levels.

CONNECT WITH JEN:

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