Productivity Tips: How to Run Your Indie Business Like a Pro

Creative superhero, rock star illustrator, and entrepreneur Willo O’Brien knows a thing or two about productivity tips.  As founder of WilloToons and co-founder and VP of Marketing for Stitch Labs, Willo is a pro at keeping her indie business seamlessly organized.  I recently spoke with Willo about how she keeps her businesses running smoothly and what productivity tips work best for her..

As a person who wears many hats, what productivity tips can you share for keeping your indie business organized and productive?  Do you keep a schedule, or do you start with what is most pressing and work down from there?

I'm a firm believer in having good systems in place. Just like keeping a house clean and de-cluttered, keeping my life and indie business together is all about having a consistent, reliable place for everything. Here are the three core systems I use to stay organized:

  • Tasks/to-do lists: I used to use Things, but now I use Asana
  • Notes: Evernote
  • Calendar: All of my calendars are hosted on Google, but I interface with them using BusyCal, which is like iCal, but better. 

The key, in my opinion, is putting to-dos on the calendar. We often schedule meetings or lunch dates, but as an indie business owner, it's crucial that we schedule time for our tasks and ourselves.

A long to-do list can be daunting, because there are often high expectations around what you can get done, with no regard to how they will fit in your actual day or week. Seeing how tasks fill the calendar gives me clarity around how long things take, which helps me plan more efficiently. I admit I don't always get to it every week, but when I do, it really helps me make conscious decisions about my days, and gives me a visual account of how I've spent my time.

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A few more applications I rely on for keeping my business organized are StitchShoeboxedMailChimp

What was the first big move you made in your indie business to increase organization?  Was it an easy decision?  If not, how did you learn to let go and seek help?

For my WilloToons product line, I first hired someone to help with my order fulfillment. I ended up giving her a fancy title of Merchandise Manager, because she not only helps ship orders, but she stores my inventory, and manages inventory between both of my online stores. She's my bookkeeper now, too. Yes, she's amazing!

However, it should be noted, it wasn't as easy as I make it sound. It took me a long time to learn how important it is to know my strengths and accept my weaknesses. Many indie business owners try to do everything themselves, and it's not sustainable or smart. I sometimes feel like the reason why I had my product line was so I could learn how to ask for help. It was challenging at first, but now I've become a modern messiah around the gifts and wonders that come from teamwork and collaboration with others.

What do you think is the number one hurdle that prevents indie business owners from taking advantage of the best productivity tips? What can we do to be as productive and organized as we would like?

Options. There are SO many different ways to do everything. Finding "the best way" often leads to wasting way too much time researching, or is simply paralyzing. As indie business owners we have unlimited ideas, but funneling those ideas into productivity tips — preferably ones that will lead to profit — can be overwhelming.

Finding an experienced mentor can save so much time and agony when trying to make your passion into an indie business.

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,, 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 balance. 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. Channeling her creative passion into a new venture, Willo is now Co-Founder and VP Marketing at Stitch Labs, a design-focused business tool for entrepreneurs who make and sell products. A perfect fit with her career and expertise, Willo is now able to support business owners with an elegant tech solution that helps save their precious time and energy, so that they can sustainably grow their business.

Willo can be found as @WilloToons on everything... say hello! 

Check back next week for Part 3, as Lisa Anderson Shaffer learns to tackle that overwhelming pile of papers and to-do's with the tips she's learned from the pros!

Resource category 



Use IQTELL as your Productivity app and manage you To-do lists, Evernote and all your calendars on the same app and for free...just a suggestion :)

Robyn Coburn

Please, please, please set the links in your blog posts open in a new window!

I am giving up reading here today because click-click-clicking back to the original blog post is such a pain.

MaryAnn @ Craft Maker Pro Software

I've been using a tool/software so I can organize everything I needed to do and achieved the goals I've set for my business. This software really makes my inventory tracking a lot easier, accurately price my product and a lot more.

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