Teela Cunningham

The 5 month runway

What happens when you give up traditional expectations to fund your biggest dreams? Find out how Teela Cunningham went from crying during her commute to covering her family’s living expenses for a year with one launch.

Sometimes, Teela cried during the hour-long commute to her agency job as a graphic designer in Atlanta.

Her job was to help to create visuals for brands.

But she wondered if she was enough.

Her superiors kept rejecting her designs, and it made her question her worth as an artist.

Teela Working

Am I just not a good artist? Should I be pursuing something else? Nobody wants to use the artwork I'm making.

Maybe she’d chosen the wrong career?

But there was only one problem.

She couldn’t stop making art.

And she couldn’t turn off her desire to share it.

So she started focusing her attention on making art in the evenings. And instead of looking for affirmation at work, she started to share her work online instead.

creator drawing on tablet

People loved her work, and their positive reception changed her whole outlook. “I have something to offer,” she started to believe for the first time, a crucial realization for any artist.

And while that didn’t completely stop the tears on her commute, they transformed into a kind of liquid courage. Instead of crying in resignation, she’d ask herself bold questions, brainstorming ways to stop the tears; maybe she should look for another job?

But she wondered if she was enough.

Or maybe, just maybe, it’s time to start building her dream business?

Teela dreamt of having her own business since her first job out of college, where she worked for a small early-stage startup. The chaos she saw there empowered her:

I realized, it's okay if you don't have it all figured out. You can still have a business and figure it out as you go.

She was determined to figure out how to turn her art into a business that would allow her to quit her job.

“When I got home from the day job, that's when my life happened.”

When Teela was in first-grade, a friend asked her what she wanted to be when she grew up. Her answer was instant: “An artist.”


She asked for art kits every year for her birthday, and she’ll never forget her parents’ reaction when she’d show them something she created: “Oh, you're a great artist,” they’d say.

She didn’t know what it meant to be a professional artist then, but she knew it’s what she wanted to do, and she believed that somehow, she’d figure it out.

So when she started to feel artistically unfulfilled in her day job, she started a blog as a way to share more of her art. She’d started blogs in the past but struggled to be consistent, so she decided to call this one Every Tuesday, in hopes to dedicate herself to her craft every week, each Tuesday.

She started Every-Tuesday.com in October 2013 and shared her art along with written tutorials so others could create every Tuesday along with her.

Then, that Christmas, her fiancé bought her a USB microphone, and in January 2014, she shot her first YouTube video using the mic and sharing her screen.

She found it was more natural for her to teach using video. She kept going, sharing a new video every Tuesday, often staying up until after midnight to create.

Creator Portrait

She didn’t make any money with it. But she loved it.

When I got home from the day job, that's when my life happened.

Teela had no idea yet how to turn this thing she loved into a job, but she was determined, and she had that thing you can’t rush – momentum. By this time she’d created something new every week for almost two years.

It felt like a million dollars.

Teela followed several bloggers and YouTubers who made a full-time living with their work, but she had no idea how they were making money. But because of them, she knew that it was possible.

She wasn’t crazy.

She began with trial and error, putting herself and her art out there wherever she could, keeping her eyes wide open for any opportunity to share and teach, trying out new platforms as she heard about them.


Her original strategy was to try everything, hoping something would stick.

So when she heard about this new free online design tool called Canva, she submitted her designs. When she heard about a new platform called Skillshare, she created and sold her first online course on letterpress printing.

That’s when she made her first $600.

It felt like a million dollars.

It felt like hope: If she could make $600 doing something she had already been doing for free for almost two years, what else could be possible?

The momentum was starting to pay off, and it gave her the energy boost she needed to direct her attention toward figuring out how to build from that $600 and learn how to make a sustainable full-time living with her art.

Quote over artist workstation

Let's see how far we can go.

She kept making new courses on Skillshare, and every time she did, her income grew.

Painting and Letter Press

In addition to those courses she also created and sold hand-lettering fonts.

Through years of content creation and lots of trial and error, Teela’s business model was born: creating digital art products and teaching others how to create digital art products.

Getting in on some of those trends like hand lettering really helped her build momentum in the early days, but what helped her turn that luck into a sustainable business, was:

  1. Creating a lot.
  2. Paying attention.

In addition to creating constantly, Teela also put just as much attention on noticing how people were responding, especially paying attention to what questions they asked and what they requested more of.

She listened intently and let her audience inform what she created next.

Her business was built on a feedback loop: create, listen, create, listen, create, create, create.


But despite the new income coming in, her business wasn’t consistently matching the income of her day job. It was, however, requiring more and more of her time to keep up the pace of creation that was working so well.

She started to feel the tension, and wasn’t sure how much longer she could continue staying up after midnight to keep her business afloat.

She also had other things to tend to that year – 2015 – like planning her September wedding.


When she wasn’t creating for Every Tuesday, working at her day job, or commuting, she was looking for a caterer, a DJ, and a dress. They’d been saving money for a year to pay for everything.

As the wedding day grew closer, Every Tuesday continued to accelerate, until one day, momentum took over and not only did it begin to consistently match Teela’s income – but it looked like it might also match her fiance’s as well (he also worked at the same design agency and sometimes helped her with Every Tuesday).

They were both unhappy at their day job.

They couldn’t help but wonder; what would happen to their growing business if they both went all in?

It would be risky for both of them to quit at the same time, but they knew they could always go back and get an agency job. This business was growing and it felt like now was the time to see what it could really be.

But the income wasn’t super consistent yet. They would need some financial runway to feel comfortable enough to quit their jobs.

They remembered all the money they’d saved for the wedding.

Quitting their jobs sounded better than a wedding.

So instead of having a big wedding in September 2015, Teela and her husband got married at a courthouse and quit their jobs to go all in on Every Tuesday.

Their wedding money would give them five months of financial runway to see if they could make this work. If it didn’t, their plan was for her husband to go find a job.

But for the next five months, they vowed:

We're in this together. Let's see how far we can go.

Creator holding photograph

Really good marketing isn’t about having to brag about yourself or your art.

They were still absolutely terrified.

They’d said goodbye to stable income.

They had five months of living expenses.

Teela directed all her energy toward doing more of what was working, but now at an even faster pace with full-time dedication and her husband as a full partner.

Creator Graphic Every-Tuesday

She kept listening and kept creating – one of her videos on watercolor even went viral (it has over 2.8 million views to date).

YouTube became a place where she would beta-test her course ideas. If a video did really well, it was a good sign that it might be a great foundation for a course.

As she created more courses based on what videos were doing well, her income grew even more.

But what really changed everything for her, she says, was giving as much time and attention to learning online marketing as she did to her learning her craft.

I definitely invested a lot of my time into learning online marketing because I knew just being an artist and putting out really beautiful artwork wasn't going to be enough to keep my business running long-term. I knew that if I wanted to push my business to the next level I needed to learn online marketing, because that's something they just don't teach you in art school.

Easier said than done, especially for artists, so I ask Teela what helped her get comfortable with marketing as an artist.

Art Supplies

For her, it was finally understanding that really good marketing isn’t about having to brag about yourself or your art; it’s actually the opposite.

Good marketing is about understanding how your craft will serve someone else and then sharing your creative work as an act of service, making it all about your audience, not about you.

That was freeing.

To learn online marketing, Teela listened to podcasts, like Smart Passive Income by Pat Flynn.

She’ll never forget hearing Pat say, “If I could do it over again, I would've started my email list sooner. That's the biggest thing I would've changed.”

Teela started her email list right after hearing that episode.

But she was still scared.

“I have no idea what I'm doing.”

Teela knew that to do email well, just as when she started Every Tuesday, she’d need to be consistent so that they’d remember her.

But that’s when that new-platform-fear kicked in. You know, that moment you’re about to share your work in a new space and, even though you’re just beginning, you somehow feel like you’re about to walk on stage in front of a stadium full of people to give a speech without having anything prepared.

Creator creating

It’s terrifying.

But creators like Teela do terrifying things every day (or at least every Tuesday).

And the best part is when you walk onto that new “stage” you realize your imagination (or fear, for that matter) had tricked you.

It’s not a stadium, at least not now.

It’s more like your living room, a few of your closest friends on the couch, snacks on the side-table.

Teela wrote her emails honestly, telling her small but growing email list:

I have no idea what I'm doing, so I'm going to try and figure it out and hopefully you'll be along for the ride.

She started slowly, writing two emails a month.

I didn't want to inundate people with too many emails. I didn't want to discourage them from staying on my list. And I was secretly scared that if I started emailing them every single week that I would lose a bunch of people.

But Teela’s business name – Every Tuesday – kept nudging her to email weekly. Finally, she realized:

I'm Every Tuesday. It's okay to hear from me every Tuesday. And if they don't want to hear from me every Tuesday, then why are they following me? It doesn’t make sense for us to maintain this relationship if you don't want to hear from me every Tuesday.

Creator Graphic Every-Tuesday

While a few people dropped off, her list kept growing, and growing, and growing (people joined her list via the free resources she’d share on her YouTube tutorials).

And instead of being “annoyed” that she emailed them each week, instead, she got email replies like this:

Teela, I don't know if you're going to get this, but I just wanted you to know that I look forward to every single Tuesday now because of you.

Email, Teela says, was the key to the next phase of her business; she loved YouTube and Skillshare, but she didn’t own her audiences there. Email gave her the ability to bring them from those platforms onto her own, opening the doors for the course launch that would change everything.

Creator Graphic Every-Tuesday
Quote over art supplies

It was the first moment they truly felt like they could breathe.

Now that she had her own audience to communicate with directly, she felt ready to create longer, more in-depth, self-hosted courses.

Her first two self-hosted courses made five figures each.

Teela realized that people were willing to pay even more for a course that had more in-depth teaching. And self-hosted courses seemed like a great pillar for her business model – if they could have consistent five-figure launches, they could really keep this going.

Her third self-hosted course focused on teaching people how to convert their handwriting into sellable fonts.

LetteringBy this time, she’d been building an email list for two years and had created about 12 courses prior.

Creator Graphic Every-Tuesday

She launched her third self-hosted course in March 2017, hoping for another five-figure launch.

But that didn’t happen.

It made six figures in its first week.

That one launch covered their living expenses for the next year.

It was the first moment they truly felt like they could breathe, the first moment, two years after quitting their jobs, where they firmly, finally, felt like, “Okay. We can do this.”

Creator recording tutorial

“I wish I had known that back then.”

Sometimes Teela still can’t even believe that this is her life – she still vividly remembers what it felt like to cry on the way to work.

I ask her what advice she has for any creators who are there now, creatively unfulfilled in their day job, in pain, and perhaps also questioning their worth as an artist:

Whatever people are saying or thinking about your work at your day job, whatever is making you miserable, that's not your worth. However people make you feel, that is not your worth as an artist.

Your worth comes from how you feel about yourself when you're creating the artwork that you want to create for yourself. Stay focused on your aesthetic, the goals that you have, not the goals that other people have for you wherever you're working.

Stay true to yourself and stay focused on your own goals because that's what's going to carry you. I wish I had known that back then. I wish someone had just said that to me because I questioned myself so many times.

And it's really, really important to remember why you started this to begin with. I mean, you had a love for art, you had a passion for it at some point, find that passion again. Do it for yourself.

Creator Stats Teela
Teela and her husband still work on Every Tuesday full-time. They even paid off all their debt – their house, and all their student loans.

Do they regret trading a wedding for a business?

In a word?


Or even better, the answer can also be found in a name.

Last year, they had their first child. A baby girl.

Her name?



Creator Family

Support your growing business

ConvertKit helps creators like you grow your audience, connect and build a relationship with that audience, and earn a living online by selling digital products.

Start a free 14-day ConvertKit trial

Isa Adney

Isa is an author and writer and has profiled incredible creators and artists, including Oscar, Grammy, Emmy, and Tony winners. When she’s not writing or interviewing creators, she’s probably walking her dog Stanley, working on her next book, or listening to the Hamilton soundtrack for the 300th time.

< Previous Story
Empty Nesters
Next Story >
The Bulldog

The future belongs to creators

ConvertKit helps creators like you take their projects from idea to reality. It's never been easier to build an audience and grow a business. And you can do it all for free.

Launch your next project