Willo O’Brien – Founder of WilloToons

[quote style=”boxed”]Recognizing that as an entrepreneur or creative, you’re putting your heart and soul into your work, and that it’s so important to stay connected to the passion and inspiration that drives you. Furthermore, as we get more connected online, we’re finding ourselves more disconnected to our physical bodies. Our health and happiness is paramount to our productivity![/quote]

Willo O’Brien has made a career out of creativity. As an artist, social supercollider, and self-described geek for over a decade, Willo has a passion for empowering fellow creative entrepreneurs.

Willo’s online home since ‘99, WilloToons.com, has served as a platform for selling her ‘geek meets rock ‘n roll’ product line, for showcasing her illustrations and designs, and as an outlet for her thoughts on business, technology, and work/life integration. In 2011 she premiered WilloToons Connect, a video series dedicated to discussing Creative Sustainability with other successful artists whose craft has evolved into a business.

Willo shares her expertise advising startups, coaching creative small business owners and speaking at events around the country. Willo can be found as @WilloToons on every social platform out there…. say hello!

What are you working on right now?

After a year serving as Co-Founder & VP Marketing at Stitch Labs, I decided it was time for me to dive back in and fully embrace my work as a Creative Business Coach. Within a few weeks, inspired and in the flow, I launched RE:CONNECT – Get Unstuck & Find Your Magic; a 5-week ecourse led by me and my collaboration partner, artist and author Mati Rose McDonough. We successfully completed our first run – completely exceeding all of our expectations – and are in preparation for launching our second one now.

I’m also developing a few additional courses dedicated to helping creative entrepreneurs thrive, and ‘passionate workaholics’ stay in love with what they do.

Where did the idea for WilloToons come from?

I’ve been self-employed for 10 years now, and there have been a few companies (and a lot of ideas!) within that time, but the current incarnation of my work is really centered around Creative Sustainability. Recognizing that as an entrepreneur or creative, you’re putting your heart and soul into your work, and that it’s so important to stay connected to the passion and inspiration that drives you. Furthermore, as we get more connected online, we’re finding ourselves more disconnected to our physical bodies. Our health and happiness is paramount to our productivity!

What does your typical day look like?

As I’m writing this, I’ve challenged myself to a very focused month of creation and change. I’m partaking in NaNoWriMo – which I share more about here – and that has me writing up to 1600 words a day. Hence why you’re finally getting this interview from me. 😉 I’ve also let go of my iPhone in bed habit, and have sworn off drinking this month, in addition to creating a few other healthy habits. All that is to say, my days are a lot different than they were just a month ago.

Given that I set my own schedule, these days I gently get out of bed (no iPhone consumption and trying to be on a regular sleep schedule vs setting an alarm) and make tea in preparation to sit down and write. Other engagements are meeting with my collaborators to discuss next steps on our projects, meetings with coaching clients in person or over the phone, and getting out of the house for a walk or hike. Evenings, when not writing or working on a project I’m passionate about, I spend time with friends. Every day is different and I like that.

I’ve had many years of my life going really fast, with mountains of work to do at a breakneck pace. These days, through meditation and conscious intention, I’m attempting to create space in my mind and slow time down. It’s working and it’s glorious. I invite you to join me!

How do you bring ideas to life?

Collaboration and execution with a plan and a purpose. I worked solo for a long time, and while I am still very self-motivated, I absolutely adore the magic of collaboration. It’s important in this process to recognize where it’s feeling stuck, and where you are finding the creative flow. Mastering that, and honoring the ebb and flow of the cycle, takes patience, but in the end it’s so worth it! The purpose for me often goes back to a bit of an accountability piece. Recognizing the larger gift in what I’m creating and how it will help others is what wakes me up in the morning.

What’s one trend that really excites you?

Health awareness. Apps like SuperBetter and Lift that help individuals track how they are taking care of themselves, as well as more advanced technology for the medical/hospital space. This is an area that is ripe for innovation, and it’s really exciting to see venture dollars being invested in sensible and sustainable solutions for the emotional and physical health of the human race.

What was the worst job you ever had and what did you learn from it?

I haven’t had many traditional jobs in the last 10 years, but I most certainly have had clients and projects that have made me miserable. The biggest lesson I learned in being a freelancer early on is that “I won’t be a victim of my own choices.” Meaning, I am the one who has the choice to take on a certain project. I have agency to say yes or no. I am the one who sets the boundaries and expectations. Therefore if I’m feeling miserable, or not ok about how something is going, I can’t sit around complaining and being a victim about it. I am the one who has to make the change.

If you were to start again, what would you do differently?

I would know my worth and charge more. I feel like I left thousands and thousands on the table in the first 5 years of my business. I wanted to help, the work came easy to me, but others wanted it and I needed to recognize that I deserved to charge more. Level up my game, own my awesomeness and get serious about making a serious profit.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Stay humble, keep learning, and don’t get caught up in perfectionism.

What is one business idea that you’re willing to give away to our readers?

There is power in the series.

If you could change one thing in the world – what would it be – and how would you go about it?

Human suffering. Teach love, compassion and acceptance.

Tell us a secret.

Embarrassingly the email with these interview questions has been sitting in my inbox for 9 months. You initially made contact right after we’d closed our seed round and the next 5 months at Stitch was super busy! After leaving Stitch I launched back into launching ReConnect, and didn’t focus on anything else but getting that off the ground. Anyway, all that is to say I try to keep close to inbox 0 and this is a great example of how I didn’t transfer it to my To Do list or calendar (my preferred GTD flow!). Correcting this today by answering & emailing you the answers, obviously, but this is not the modus operandi I preach. The good news is I managed to go from about 140+ emails to 13 today. Progress!

What are your three favorite online tools and what do you love about them?

Evernote, Dropbox and Asana help me efficiently organize the information in my life.

What is the one book that you recommend our community should read and why?

Start Where You Are, by Pema Chödrön.

What’s on your playlist?

The Lumineers, Faded Paper Figures, Stars

Three people we should follow on Twitter and why?

@joelgascoigne – Founder of @BufferApp, consistently tweets excellent resources for productivity and entrepreneurship.

Two that regularly make me laugh out loud: @MrsRupertPupkin + @ShitNobodySays

Who is your hero?

Jen Louden, a pioneer in the self-care movement. Her dedication to her truth, and willingness to give and share her knowledge with others is so inspiring to me.


WilloToons’ Blog, Video series and more:
WilloToons on  Twitter:
WilloToons on Facebook:
WilloToons on LinkedIn:
WilloToons on Flickr:
WilloToons on Tumblr: