Creator Q&A: Making big moves with artist Shelby Abrahamsen

Customer Stories
9 min read

You might have read how artist and entrepreneur Shelby Abrahamsen grew her email list to 60k subscribers or what it took for her to make irresponsible art, but recently she's made some big pivots to her business.

Biggest detour or pivot your business has taken since you first started
When I first began blogging, I was exclusively creating content about bullet journaling. After five or so years of this, I naturally began to drift from this topic because I felt like I had conquered that mountain and had little left to share. However, I felt like I was stuck in that topic and couldn't deviate for fear of losing all of my existing audience.

I wanted to pursue my art further without the constraints of bullet journaling keeping me in a box. After a difficult period of self-reflection, I finally decided to push forward with the art content and see what happens.

I'm still in the process of seeing where that road will take me, but my great fear didn't come to pass. I didn't lose my existing readers, and my business didn't collapse.

In fact, most people were extremely supportive of my journey and cheered me on. This was an enormous change for me, but I'm so glad I pushed past the fear to break out of my box.

The most recent obstacle you've overcome in your business
Video production has been slow, clogged, and convoluted for years. We have patched it with various services and fixes over the years, making it overwhelming to pursue new ideas or finish old projects. So many projects died on the cutting room floor thanks to a poor video editing system.

We finally broke down and hired our first employee to handle it, and the amount of relief I feel is already palpable. I can't wait to see how we can tackle video projects moving forward.

Biggest transformation from when you started your business to today
After eight years in a mid-sized city that didn't particularly excite or inspire me, we finally moved to Chicago, and I'm LOVING it. I was always afraid to move somewhere more expensive because the fear of failure was intense.

But after eight years, we decided that we were done with the fear and excuses.

We sold our house, our car, and most of our belongings to start fresh in the city. It's been the most creatively inspiring transition of my life, and our business has already grown in the short time we've been here. I love being surrounded by the diverse culture, creative people, and a dynamic environment that keeps me on my toes. I finally feel like I'm where I belong.

Hardest part of being a professional creator
Not being taken seriously by peers, relatives, strangers, etc. There is a particular “starving artist” trope that makes folks a bit condescending when they hear I'm a professional artist.

It's particularly frustrating being talked down to or treated like this business fell into my lap when I know how hard I've worked. I've worked so many nights, weekends, and holidays over the years. And a paycheck? Forget about it! I've sacrificed comfort, security, and stability for this job, and being treated like a trophy wife with a fun little blog is extremely irritating.

What helps you with burnout
I just had a major period of burnout earlier this year that completely upended my life. I talked to my doctor and therapist and got diagnosed with depression.

After taking some time away from work, taking care of myself, and some handy antidepressants, I started to come through the other side.

And loneliness is no stranger to me. I am fortunate that my husband and I both work on this business together, so we aren't truly alone. But despite general support, I never felt like friends and family really understood our choices or lives.

Moving to Chicago has helped tremendously in this regard, along with getting a studio in the Kimball Arts Center. This has put us right alongside other entrepreneurs, creators, and artists, and I finally feel like I fit in.

I hope to make some deep connections with other artists in the coming year so I can share this passionate side of my life with another person (my husband Jon is not the artistic type).

Business stats

Website &

Years in business

Online content creation

Income streams
70% Memberships for Course Platform
20% Ads
10% Affiliate

Average annual business income

Photos by @saragardnerphotography

Current location
Logan Square, Chicago

If you could only have one metric you could look at in your business
Email subscribers. It tells me a great deal about my audience and what they want from me as a creator. Plus, I find that email subscription numbers aren’t as wild and mysteriously algorithmic as social media or website traffic; I can easily grasp the metric and understand how to affect it.

The analytic you check most often
Click rate because I’m always tweaking my copy. If someone is willing to click a link to check out the offers I provide (or conversely, they AREN’T clicking it), I want to know so I can improve my craft.


Book that made a big difference for you as a creator
For inspiration: Big Magic by Elizabeth Gilbert. This book made me think about the creative process differently, and it made me understand my inspiration, process, and growth as a creator.

For business advice: Who by Geoff Smart. With the advice from this book, we finally were able to tackle the enormous process of hiring with more confidence (it used to scare the beans out of me). We just used these techniques for our second hire, who starts in two days!

Favorite podcast that’s helped you as a creator
This is a silly one, but NADPOD (aka Not Another D&D Podcast). I love listening to professional creative people have fun, be silly, and build amazing worlds collaboratively. Listening to their antics helps remind me that I don't need to put caps on my creativity – it can lead to some unexpected places if I only allow it.

Best online course you've ever taken
The Perfect 100 Day Project: Your Guide to Explosive Creative Growth by Rich Armstrong

Best conference you've ever attended
AdThrive Conference in Austin (2019)

Favorite creator right now

Habits and tools

One habit you do almost every day that supports your creator life
Walking my dogs – no, really! Getting outside and paying attention to the world around me inspires me every day. I'm always on the lookout for beautiful homes, interesting people, friendly dogs, lush gardens, city mushrooms sprouting in unexpected places…the world is full of wonder, but you have to go outside and NOT be on your phone the whole time.

Favorite software tool right now
Jasper AI has been a super helpful fella when it comes to writing emails or blog posts. He knows just what to add to help me get unstuck in my writing process.

Best money you've spent on your business
Hiring! We used to do everything ourselves, which spread us thin and made everything so stressful. Hiring people can be a wildly intimidating process, but taking things off of my plate and bringing on fresh new talent is a brilliant use of business money.

Best hire you've made so far
We just hired a video production lead, who technically hasn't started yet. However, video production has been one of the biggest thorns in the heel of this business, and I'm excited to finally see what happens when the rubber meets the road with video.

Best thing you've STOPPED doing in your business
Reading and responding to every email that comes in from our amazing readers. I used to spend a ton of time answering each one in-depth, and it would take ages.

And unkind emails would eat me alive because I took it so personally!

Now I have someone handling emails for me, which saves me my time and mental health. They make sure to send through particularly positive ones to make sure I'm reminded of the impact my work can have on people – those emails keep me going!

Best thing you've done so far to grow or scale your current business
Hiring and outsourcing.



Favorite part of ConvertKit right now
The funnels are so easy to set and forget! Especially during busy times of my life (such as my most recent move), it gives me a great deal of peace of mind knowing that my email list is being taken care of.

When you switched to ConvertKit
About seven years ago or so – ConvertKit has pretty much been with us since the beginning.

The most important piece of data you look at in ConvertKit
I always look at open rate above all else.

Closing thoughts

What you’re working on right now
Foxsy! We've spent nearly the past year building our new art education platform online with the help of other incredible creators, and we're so excited to see where it goes. We moved to Chicago to give us more space to grow Foxsy, both literally and figuratively. We have a larger studio where we hope to bring in local artists to teach and share their craft, and we've hired our first Chicago employee to grow Foxsy even more. I can't wait to see what it becomes in the next few years!

Dream come true moment
Moving to Chicago. This was the moment that we went all in for this business and truly bet on ourselves.

Best part of being a professional creator today
Freedom, hands down, is the best part of being a professional creator. I love knowing that I can do whatever I set my mind to – no boss, no restraints, no holding back. I sometimes need to remind myself that I have this freedom because it's easy to let fear put you in a box, but I always come to the same conclusion: This is my life, and I can do what I please.


You can follow Shelby on Instagram @littlecoffeefox, sign up for her newsletter, or learn more at and

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