When life keeps moving you around, build something that can move with you.

Dawn Nicole was working in human resources management and loving it. She had an MBA, a clear career trajectory, and zero plans to become an entrepreneur. Then she married an Air Force officer.

"Human resources is not conducive to moving all the time," she says. After relocating repeatedly for her husband's military career, Dawn found herself at a crossroads familiar to many military spouses: how do you build a career when you might pack up and leave at any moment?

The answer, it turned out, was digital products. Today, Dawn runs a successful solo business selling Procreate brushes, lettering workbooks, and online courses through her Shopify store, with SendOwl handling the delivery. She's authored three books with Better Day Books, worked with brands like Krispy Kreme and Hobby Lobby, and built a following of over 84,000 on Instagram and 238,000 on Pinterest.

But what makes her story remarkable isn't the numbers. It's the system she's built that lets her step away whenever life demands it.

An accidental creative entrepreneur



Dawn didn't set out to build a lettering empire. After realizing her HR career couldn't survive the constant relocations, she went back to school for an advanced certificate in graphic design and branding. That's when a professor made an offhand observation that would reshape her future.

"My professor said, 'Oh, you have a knack for choosing typography for lettering,'" Dawn recalls. "But it wasn't really something that was taught."

This was 2012, and hand lettering wasn't yet the massive trend it would become. Dawn had stumbled onto something early, and she leaned in. She started blogging, which was easier to monetize back then, and began sharing her lettering work on Pinterest when that platform was just taking off.

The combination of timing and talent created unexpected opportunities. "I had a guy that was a buyer for Hobby Lobby reach out to me," she says. "And then I had Krispy Kreme donuts reach out to me and had me design a coloring page style Valentine's Day box."

She almost deleted both emails, thinking they were spam.

Building for flexibility, not just income

For Dawn, the appeal of digital products was never purely financial. It was structural. With three kids and a husband whose job could uproot the family at any time, she needed a business that didn't depend on her physical presence.

"Physical products don't make sense for me," she explains. "Digital has always been my favorite. Not only is it passive income, it just works better with our mobile lifestyle."

She spent seven years selling on Etsy before making the leap to her own Shopify store in 2017. When she set up the store and started researching options for delivering digital products, SendOwl had the best reputation. She's been using it ever since.

The Shopify and SendOwl combination has become the backbone of her automated business. "Some days I'm on the golf course and still made a couple hundred dollars because of SendOwl and Shopify and the way things are set up to work, even if I'm doing other things," she says.

That automation isn't just convenient. It's essential. With her husband's demanding military schedule, most family responsibilities fall on Dawn. The flexibility to work full-time some weeks and part-time others isn't a luxury. It's a necessity.

The value equation

When asked about pricing changes across the tools she uses, Dawn's answer reveals her pragmatic approach to business expenses.

"If you feel like you're getting the value out of the service, then you still have a choice," she says. "You can stay with the company because you're happy with it, or you can find an alternative option."

She's made both decisions at different points. When QuickBooks raised prices from $10 to $50 a month, she switched to a Google spreadsheet. When her email service costs became unsustainable at $300 a month, she moved to Flodesk. But SendOwl has stayed because the automation it provides effectively replaces what would otherwise require an assistant.

"I used to have an assistant to help me. Those are things I've cut instead and I've taken on doing more myself. But SendOwl allows me to do that since it helps automate my process."

She adjusts her SendOwl plan based on order volume, scaling up in busy years and down in slower ones. It's the kind of flexible relationship that works for a business with variable income, where some years hit six figures and others are less busy.

The three-thing system

Dawn's productivity approach is deceptively simple: three things per day, after her morning workout.

"If I accomplish those three things, then I'm free to go do other things," she explains. "Read a book, golf, whatever. But those three things are a non-negotiable part of my day."

The method emerged from hard-won experience. In her early years as a business owner, work consumed everything. "The biggest thing I sacrificed as a business owner back then was a quiet mind," she admits. "When you own your own business, you are thinking about the 800 million things you need to do all of the time."

It took over a decade to develop the discipline to let go, to accept that what doesn't get done today will still be there tomorrow. The three-thing approach creates a sense of completion without burnout.

How does she choose those three things? "There's something that I have to do. There's something that I want to do. And then the third one..." she pauses, laughing. "There's not a lot of rhyme or reason to it."

The mix of obligation and desire keeps her engaged. Some days it's accounting. Some days it's SEO research. And some days it's the creative work she loves most: sitting at her iPad and creating the next project she'll teach or submit to her publisher.

The email list lesson

If Dawn could give one piece of advice to new digital entrepreneurs, it would be about email.

"No social media or platform is as important as your own email list, because that is the only thing you own," she says emphatically. "If you lose Instagram tomorrow, what do you have?"

She learned this the hard way, having once accidentally deleted her entire list of 20,000 subscribers. After the initial devastation, she reframed the catastrophe. "I can start again tomorrow. I'm happy. I'm healthy. I'm still here. This is not completely unfixable."

Her approach to email reflects her broader philosophy about respecting her audience. "I take it very seriously that they're letting me into their inbox. We all get too many emails." She sends a monthly newsletter and occasional special announcements, always including something free: a hand lettering worksheet, a Procreate color palette, a brush set.

The restraint pays off. She maintains high open rates and click-through rates precisely because she doesn't overwhelm subscribers. "The quickest reason I'll leave an email list is if they're emailing me possibly once a day or multiple times a day, God forbid."

Growing through generosity

Dawn recently participated in a collaborative Procreate event organized by another creator. Nine artists each offered a substantial freebie, like a full brush set, hosted on a shared page. To access the freebies, visitors had to provide their email.

She got 1,200 new subscribers in one week - putting her on the road back to a robust list.

The approach reflects a quote she encountered early in her business journey: "Make generosity part of your growth strategy."

"I think when you give people something, you have to find a balance," she explains. "In the beginning I did too much free, but that was kind of the nature of blogging at the time. And now that I'm more of a shop, I do a little less free, but still quite a bit on my blog."

Her current model uses free content as a soft upsell. A 90-minute Procreate tutorial might be completely free to watch, but viewers often want to buy the brushes she used in the project. Value leads; sales follow.

The next chapter

With her husband approaching retirement after 24 years of military service and her kids finishing high school, Dawn is in a transitional phase. The family will stay near St. Louis until the teenagers graduate, but they don't plan to remain permanently.

For 2026, she's focused on two growth channels: building her email list through more collaborative events, and finally investing seriously in YouTube. She's noticed that her long-form videos are driving both subscriber growth and income, and the platform connects to her Shopify store through YouTube Shop, creating another automated sales channel.

"Pinterest started doing the same," she notes. "It'll tell me exactly how many dollars each week were earned directly as a result of my pins. And all that, when people are buying, is all automated. So I really don't have to do much of anything once I kind of put the content out there."

It's the system she's been building for over a decade: create once, sell repeatedly, and let the technology handle the delivery while she focuses on what she loves or what life requires.

When rest becomes mandatory

Dawn recently spent a month sick, the result of pushing too hard for too long. An obsession with her morning workout had crept into excessive territory, with two-hour sessions every day plus walking five miles on the golf course.

"Learning to rest better would be the advice I'd give myself," she reflects. "Because if you don't learn to rest yourself, at some point, your body will force you."

It's a lesson that connects to everything else in her approach: the three-thing limit, the monthly rather than daily emails, the automation that lets her step away. Sustainability isn't just about business models. It's about recognizing that the person running the business has limits too.

Dawn lost her father while she was in college. When she turned 43 recently, she gained the perspective that she was now the same age he was when he died. That perspective shapes how she evaluates problems.

"When you have gone through anything traumatic in life, you can reframe what's going on around you," she says. "Is this important in the grand scheme of life? Is this going to matter a year from now?"

The accidentally deleted email list? It's devastating in the moment but fixable in the long run.

The work that doesn't get finished today will still be there tomorrow.

And the business that can run while she's on the golf course with her husband, learning a new hobby before the kids leave for college? That's exactly what she built it to do.