Words With Creatives: Inspiration from Artists & Creative Entrepreneurs

Words With Creatives: Inspiration from Artists & Creative Entrepreneurs, featuring Sarah Morgan (xosarah.com), Danny Gregory (Art Before Breakfast), Caroline Winegeart (Made Vibrant) & David Sherry (Death to Stock).

As our month of exploring creative business comes to an end (okay, so it's been more like a month and a half) I thought I would try and do something special for all you fabulous folks out there.

My goal was to reach out to a whole bunch of creative mavens who inspire and motivate me to see how embracing creativity has changed their life, and to get their thoughts on creative business. I hope you enjoy this collage of insights.

Was there every a time you wanted to give up on your creative project/passion, and what got you through the rough patch?

Caroline Winegeart from Made Vibrant

"I was about 6 months into Made Vibrant trying to get the business off the ground (at the time I was operating as a freelance design studio) and while out of town for a friend's birthday, I woke up to find that I had $0 in my checking account, $0 in my savings account and my credit card was maxed out. I was $7,500 in debt. Yikes.

Projects were just trickling in so slowly in those early days, and, frankly, I wasn't confident enough to ask for the amount of money I knew I should be getting paid. I strongly considered throwing in the towel and looking for a job, but thankfully my entrepreneurial-minded partner, Jason, discouraged me. He reminded me of just how capable I was and gently pointed out to me that I was operating my business from a place of fear: fear of clients turning me down if I asked for too much money; fear that I wasn't qualified enough to do what I was doing; fear that I wasn't unique enough to carve out my own place online.

Once I hit that financial rock bottom, it's like I was finally able to give myself permission to really go for it because there wasn't much else to lose. The second I returned from that birthday trip, we sat down and mapped out a plan for getting out of debt, I restructured my website to focus on one single thing — brand design — and I raised my prices. I decided that if anyone was going to believe in me enough to pay what I was worth, I would first have to believe in myself.

Slowly, as the weeks went by, my intentional confidence turned into a more natural, real confidence as clients started showing up in my inbox. It was that momentum that finally allowed me to launch my first e-course and that's when the entire business changed for me.

Because I was able to push through the fear, take ownership of where my business was lacking and find confidence in my unique voice, the business and community have evolved into more than I could have ever imagined. Today I'm debt-free, the business is more profitable than ever, and best of all, I'm able to connect with real people and encourage them to be the best versions of themselves. Sometimes it really is as simple as believing in yourself and putting in the work!"

Caroline, Made Vibrant

Share with me the best thing about your biggest failure (best outcome/lesson learned).


I think the best learning is that you just have to keep trying things and failing over and over again. Once something does work, you say, "ok, I just have to keep trying again until something works" - so persistence is the best lesson to pick up.

David Sherry, Death to Stock

What has being a creative business owner given to you/how has it improved/changed your life?

Amanda Wright of Wit + Whistle

Being a creative business owner has most importantly given me freedom. Freedom to follow my impulses and make whatever pops into my head, freedom to work when inspiration strikes instead of being confined to the hours of 9–5, and freedom to strive toward my own goals instead of someone else's. I'm excited to get to work each day, and loving what I do is the best gift I could ever hope ask for.

Amanda Wright, Wit + Whistle


I think the best thing about owning a business is the platform that it provides you. It's almost like a tool that let's you reach out to more people you'd want to get to know, collaborate with brands you love, and pursue other passions via the business. You can use it as a great excuse to do a bunch of the things you already wanted to do!

David Sherry, Death to Stock

Sarah Morgan of xosarah.com

Being a creative business owner has given me the opportunity to grow and change far more than I would have at a corporate job. Being the sole person guiding my business has been exciting and empowering. It gives me the ability to experiment, learn, try new things, and collaborate with lots of different people without having to adhere to someone else's goals, standards, or expectations.

Sarah Morgan, xosarah.com

What was your first creative passion, and who nurtured that spark?

Keiko Brodeur, Small Adventures Journal

I grew up in a musical household and took music lessons from when I was very young up until college. My mom always supported my passion for music by taking me to my lessons, concerts of artists I liked and wouldn't let me quit studying even when I was going through some rebellious teenage times. When I decided to change my major from music to graphic design she didn't miss a beat and supplied me with whatever I needed to dig my heels into something new. Both that stick-to-it attitude and willingness to learn a new skill has gotten me this far in my artistic pursuits.

Keiko Brodeur, Keiko Brodeur Illustration & The Small Adventures Journal

 What habit or personality trait do you think truly enabled you to succeed?

Kelly-Ann Maddox of Kelly-Ann Maddox.com (formerly The Four Queens)

I have a strong desire to communicate ideas. I love exchanging, corresponding and debating in general, and I like to play with concepts to discover what I really think of them. I am always eager to get other people's opinions and to give my own, especially when I have absorbed some new information that I wasn't aware of before and I want to 'test' it out by throwing it into the conversational mix. Expressing my ideas has been a defining characteristic of my business, and the more I have gone in search of new material and different subjects to have an opinion on, the more I have followed through by expressing that opinion on my blog and channel. This gives people a rich sense of what I'm all about. I consistently permit my ideas and opinions to evolve, but I am not afraid to put that evolution on show so that others can benefit from it in some way.

Kelly-Ann Maddox, kelly-annmaddox.com

What creative tool/resource could you not live without?

Podcasts! And audiobooks, it's such an amazing way to consume vast amounts of knowledge while you're on the go.

David Sherry, Death to Stock


Tell us about one book that changed your life in a big way.

When I was in my late thirties, I started to draw. Actually, I started to keep an illustrated journal of my daily life which caused me to start drawing for the first time since grade school.  Soon, I had amassed a lot of sketchbooks filled with the story of my daily doings. My dream was that one day I could do some spot illustrations for a book or magazine. Eventually, I decided to pick a publisher and send them some of my work. To my surprise, they were interested and offered to publish a whole book of my work.

After we started to work on the book, the editor asked me what I thought would be the organizing idea behind the book. I threw out various ideas, none of which were adequate. Finally she asked, "When did you start drawing?" and I told her it was just a few years before. Then she asked me why, what had happened to start me on this path. I explained that a few years before, my wife had a terrible accident. She was run over by the New York City subway train and left paraplegic. In a search for meaning, I had started to make art. She said, "That's your story!" And I replied, "I don't think I want to share that with the world. I just want to have a book of my drawings." This conversation went on for a while until I realized that I wasn't going to have my book published. So we tore up the contract and went our separate ways.

A couple of years later, another editor convinced me that I should share my story. And by then, I felt ready to do just that. And so my drawings, the story of my wife's accident, and the change it brought to my life became a book. The book was called Everyday Matters and it changed my life. Not only did it start me on a path that has since become my full-time job and led me to write another half-dozen books, but it taught me the power of vulnerability, of honest, of sharing, of art. I discovered that by being willing to expose myself, I would learn the truth of what was in my heart. I could find others who would add further depth to what I was discovering about myself. And by putting down my everyday truth on the page and putting it out there, I saw myself clearly in a way that has unburdened me in many ways. Everyday Matters taught me the transformative power of creativity, of honesty, and of courage. I didn't know that stuff was in there when I wrote it. But I'm glad I found my way to it eventually.

Danny Gregory, Art Before Breakfast

Thank you so much to all of the participants for taking the time to share with me their thoughts and experiences.