Stephanie Halligan is the blogger behind The Empowered Dollar and Art to Self. The Empowered Dollar won a Plutus Award for Most Humorous blog in 2014. Stephanie has doodled since she could walk and talk, and she has created a successful business based on her ability to draw, as well as her passion for helping people make the most of their finances.

Stephanie is an inspiration to many bloggers, especially entrepreneurs looking for a bit of a pick-me-up. Through her outgoing personality, and her insightful drawings, Stephanie reaches entrepreneurs, bloggers, non-profits, and consumers in a way that empowers them.

Stephanie Halligan

One of the most inspiring aspects of Stephanie’s story is how she has gone from being employed by someone else to turning her passion into a business that allows her to live the life she wants. I wanted to learn more about the inspiration behind her latest project, Art to Self, and how she finds the energy to keep moving forward.

How did you prepare to make the leap from being employed to being self-employed?

I knew I wanted to have a few months of savings in the bank and pay off my student debt. That meant saving up a lot more and getting aggressive with my loans toward the end of my job. I also kept working on the side and keeping my client pipeline “alive” before I took the leap.

What are some of the skills you have that transferred well from being employed by someone else to being self-employed?

I worked for a startup before venturing out on my own, so I got to practice bootstrapping, and working with the minimum amount of resources. I also became really clear on what I want for my days to look like, since my days were so hard at my former employer. So I would say I learned how to get by on the basics and create a life I want.

You already have success with The Empowered Dollar. Why did you decide to start Art to Self?

Art to Self was born out of two needs I had: to do art every day and to remind myself that I’m doing a good job each day. I tend to be hard on myself (like any entrepreneur) so now I get to send out a daily doodle and positive affirmation that I know makes me feel good and makes others feel good too. Thus, a daily art inspiration and affirmation email was born.

What were some of the things you did to prepare to launch Art to Self?

I underprepared. I realized I needed to just start, otherwise I would never get going. And since it’s a daily email, I know I need to focus on the long term and just get going today.

What is the most challenging aspect about keeping Art to Self going?

Getting caught up in growth. I love creating the art and writing notes every day. And while I am marketing it here and there, I have to remember that the growth will be slow. And that’s okay.

Do you have other projects you are working on?

I just launched a course to help freelancers and solopreneurs price their services and charge what they’re worth: YouDeserveMore.co. I’ve been getting so many questions from fellow entrepreneurs about how to price their work. I took all our conversations and what I learned from raising my own rates and put it into a course to help people break through their blocks around setting prices with confidence.

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