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A few months ago, I embarked on a 100-day journey of creating, with several thousand other souls around the world. A few days ago (and with apologies in advance to Willie Shakes for the reference) I screwed my courage to the sticking place, left my actual apartment, and met a handful of them in a local Los Angeles park.

I showed up with nothing but a boatload of social anxiety and a small sketchbook housing a sampling of the 100 days’ work. (Note to self: the next time you are invited somewhere to mingle with other humans, please read the ALL the instructions on what to bring!) But as I began flipping through other people’s sketchbooks and art pieces, I felt my anxiety melt away, replaced by excitement and wonder. Here were all of these people just like me, only different, taking a plunge into the unknown and committing to creating and publicly sharing one piece of a personal project every day for 100 consecutive days; not to mention the work, which was amazing!

meetup-post insta-100days

There was a collage project, several drawing projects, and a batch of photography projects. The parameters of the projects were random; some following no rules, others tightly orchestrated. They were made from years-old swipe and from state-of-the-art Japanese gel pens. They were hand-drawn, digitized, cut from pieces of paper, or done completely on iPhones. They were created to reinvigorate a professional practice by infusing it with new life or to reawaken artistic habits sacrificed, as they too often are, on the altars of demanding day jobs.

What they had in common, though, was that they were done. That alone made them awesome and I mean that in the traditional sense of the word. Here were a dozen or more people, one packet out of thousands, who, by making one thing every day for 100, ended up with a brand new body of work—not to mention a work habit.

I’ve written many times before about the virtues of doing a little bit every day, but it has only been this year that I’ve combined the magic of a committed group of people AND the internet to provide accountability. And the combination is magic: over the 31 days I drew daily, I could see my drawings improve. As for the 100 days in a row that I lettered, not only did my work get better, but I actually stopped worrying about whether it was good. Well, to a degree.

That’s a kind of freedom I’ve always longed for with my performing, but not found yet. So I figure, why don’t I continue to cultivate it in this new area of lettering and art, where the stakes appear to be lower for me, and see where it leads me? After all, by doing these two exercises I’ve certainly gained confidence in a lot of ways that have nothing to do with putting things on paper. My day jobs have gotten easier and I’m better at them too, now that I get my strokes and kicks elsewhere. And I’ve gotten more interested in what other people are creating because as a newbie in these areas of creation, I just can’t be jaded—it would be too ridiculous.

Which is why at this meet-up in the park, after a serious heart-to-heart with another participant (globe-trotting rare-book hunter by day, fine artist by night), I decided to commit to my first 365-day project, starting on September 13th. I’d been kicking around the notion of a year-long daily project since I started seeing results at around Day 40 of this last one, but was put off by the thought that I’d have to wait until January 1st to start. That is, until I realized I could start my year on any day I liked, today included.

Ultimately, I opted for September 13th: enough days away to solidify some parameters for the project, but not so far away that I’ll lose my inspired mojo from the meet-up. Besides, it happens to be my birthday, and I can’t think of a better way to live out my 55th year than to make a bunch of crazy art. Oh, which reminds me, if you are thinking of jumping in, consider the following:

  • Post publicly—definitely your output, but also your intent. Let people know what you plan to do. It’s somehow harder to let other people down than it is to bail on yourself. Instagram is great because it’s quick and easy, but Facebook, Twitter—pretty much anything but disappearing Snapchat will work.
  • Choose a unique hashtag and tag each post. It makes it easier to show people what you’re doing when they ask and it’s good for legacy. (I’m going to tag my own project with the hashtag #365to55, if you want to follow along and help keep me accountable.)
  • Also, choose some parameters. While I don’t regret deciding to letter every day, I now see how a few confining and/or defining elements would have been valuable: the amount of time I will spend each day (and no more!), so it doesn’t become burdensome; an “angle” other than the wide-open “lettering.” Toward the end of the 100 days, I came up with the idea of putting one thing I loved on a Post-It note every day. Suddenly, the project became lighter, easier, and far more fun. Specificity is definitely your friend in this regard.

If you feel inspired to do your own project, or if you have a project you’re already in the midst of, I’d love to know about it. You can do so here in the comments, or tag me on Instagram where I’ll be posting.

Happy making, fellow artist!

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BOOK(s) OF THE MONTH: Why did I wait two years to read The Authentic Swing, Steven Pressfield’s fantastic breakdown of generating work from idea to finished product? Because GOLF. Please—don’t be like me and let the analogies turn you off. There is so much good, inspiring stuff in here for artists and other makers of things that even if it mattered, you should overlook the golf business. As it is, it’s like the best of the (horror, crime, romance, sci-fi, sports, etc.) genres: transcendent. Highly recommended.

Colleen Wainwright is a writerspeaker-layabout who started calling herself “the communicatrix” when she hit three hyphens. She spent a decade writing commercials and another decade acting in them for cash money. Now she uses her powers for good instead of evil by helping creatives learn how to strut their stuff in a way that makes the world fall madly in love with them.