Our 200-Day Creative Streak

psst...it's a Hidden Track!

On October, 23, 2021, my friend Felipe texted me.

In a conversation we’d had a few weeks before, he mentioned wanting to build a habit of doing something creative every day. I wanted in on this habit too, so on November 7, 2021, we both started something we’ve since dubbed “Creative 20.” Yesterday we hit our ((( air horns ))) unbroken 200-day streak. Every day for 200 days, we’ve done something creative for 20 minutes, sometimes less, but usually more. 

I just wrote something about “small victories” and deleted it. Why qualify it like that? Creative 20 means a lot to me and today I’m writing about it as The Drip’s first hidden track, a capsule post untethered to the monthly mixtape theme. (We’ll come back to wrap up PINK before the end of the month.)

I will preemptively acknowledge that there are many existing methods, advice books, and techniques to help artists overcome blocks and tap into their creative powers. Felipe and I consume and share a lot of this content. Perhaps the most well-known exercise for this is “morning pages” from The Artist’s Way by Julia Cameron, a journaling practice when you write roughly 3 pages before you start your day. What we’re presenting here is not original or revolutionary in any way, but it’s been a fun, meaningful, and now essential daily practice that we hope to invite others into, if you feel so curious. I happen to believe creativity becomes contagious when you collaborate.

But before we go further, let me introduce my friend: Felipe Diaz-Arango is a creative strategist for an ad agency. He is also a videographer, writer, and artist whose projects include Touchy Subjects, a documentary about the consent-driven, cuddling community in Chicago; newsletters and screenplays; paintings; and graphic design.

Illustration by Elspeth Michaels

And me: I’m a visual designer, with a background in museums, education, and more recently, healthcare. I’m also a writer (surprise!) and an artist who loves to work in ink, markers, spray paint and Procreate. I taught art and design last year at my old high school, which I loved, and I’m still involved with curating and hanging gallery shows there.

Illustration by Elspeth Michaels

So yes, we technically already do creative work every day. However the demands of our jobs, like all jobs, are so result-oriented that we often feel disconnected from the joy of making, the experimentation without the pressures of execution. The impulse for Creative 20 sparked from the desire to return to process and play, setting time aside to be prolific in our own personal projects. While there aren’t strict rules around what we consider creative, we don’t count the assigned work in our jobs as part of Creative 20. Projects that feel joyful and self-motivated count.

“It’s about self-expression that is imprinted onto the world somehow,” Felipe adds. “I have to feel excited to do it, and that I’m learning more about the craft. A lot of things count as creativity, but I didn’t want to fall into the trap that work assignments count.”

We text every day to let each other know what we worked on and for how long. At this point, we’ve gotten into an easy flow of feedback and encouragement. While our projects are separate, it still feels like a daily collaboration. Witnessing each other’s processes makes us feel more invested in our collective work, especially for projects that take longer to complete.

Last week, we talked and put together a mini-status report-meets-retrospective. We asked each other what we gained through this practice as we approached 200 days.

Felipe:

“I feel like being an artist is much more part of my identity. In my Instagram profile byline, I added ‘worker-artist.’ I don’t think I would have described myself like that before this. Identity is a weird, arbitrary thing—we give more credence to labels, but if there is something you do every day, you can call yourself that. My default is you can call yourself something if you can do it professionally or get paid, but that’s a dumb, capitalist way of thinking about it. I’m not the best painter, but I am a painter when I’m painting. I gained more confidence.

Creative 20 lessened my fear of taking action on these projects. The fear doesn’t go away completely—that dread or butterflies right before you’re going to start, but it’s way less. What’s cool is when I’m going to work on a design, I’m not as scared of failing at it. I have this feeling with everything I take on that it’s going to work out. I grew up with this story I would tell myself that I suck at drawing, but I gained a carefree-ness to try stuff out. There is no medium that feels like I don't have a right to try. I have the right to work in any medium, to try to tinker.”

Me:

“I agree with that feeling of being able to own that ‘artist’ label more. For me, it’s ‘writer.’ I started writing The Drip as part of Creative 20 a few months before I had heard of the Joel Gay Creative Fellowship. I’ve had this hip hop-meets-art history project idea since college, but I never gave it the time and structure it needed to develop further. Writing almost everyday for 20 minutes would turn into hours once I hit a groove. The more time I spent writing, the more I believed and invested in this idea. Creative 20 not only prepared me for the fellowship application, but even more so now, as I’m adapting to the rhythm of researching and writing weekly posts.

When I’m feeling overwhelmed by work, Creative 20 helps me compartmentalize and focus on a singular project, or offers the option to escape it. I don’t always use it to write—one of my favorite Creative 20 days was when I cooked a dinner for my family only using yellow ingredients, aka ‘yellow meal.’ (I’ve also done ‘orange meal’ and ‘red and green meal,’ but ‘yellow meal’ still reigns as my nephew’s favorite.)

Through sharing our project progress daily, I realized I got better at giving and receiving more direct feedback. I used to worry about hitting you up for feedback, or offering notes, but I don’t feel that squirminess anymore. I really appreciate that development, and I don’t think I expected that to happen when we first started. I see this improvement at work as well when I’m advocating for a design or pushing back on changes.”

I’ll be honest, as much as this practice has enhanced my life, there are times when adding more creative work to my day stresses me out, in a way that it doesn’t for Felipe. Sometimes I get mad at Creative 20, sometimes I think I’m better off taking a break, but I’m always glad and relieved when I finish. When I feel especially burnt out, I text Felipe about it and he’ll suggest amending the 20 minutes to 5, or doing something that requires less brainpower. When either of us feel dissatisfied with the outcome of that day’s creative output, we remind each other that it’s about the process and how the act of just doing it is still a win. I think we’re both surprised we made it to 200, and jokingly acknowledge that our streak wouldn’t have lasted this long without the support, accountability, and low-key peer pressure.

While we’re both aligned in what counts as Creative 20, we have different approaches. Felipe feels more creatively charged in the morning, for me it’s at night.

Choose your player: AM edition

Illustration by Elspeth Michaels

Good morning!

“It’s important for me to do Creative 20 in the morning. This habit is more ingrained and trusted at that time than doing it in the afternoon. Experiencing stuff drains my energy. With the previous day’s experiences and the added synthesis of dreams and rest, morning is brimming with semi-refined ideas. By doing it in the morning, I can spill out today’s concoctions of weirdness that brewed at night while sleeping.”

Felipe’s tips:

1. Make it as tiny as possible as a baseline.  One minute a day of working on something is enough and adds up. Don’t psych yourself out by assuming you have to do a lot.

2. Start a handful of projects, in different mediums if possible—switching between different ones ensures variety and staves off burnout.

3. Doing it first thing in the morning works best for me—it starts your day off with good energy, and there’s no stress about doing it later.

4. Keep a buddy or two to report to each day. It makes it less lonely and it’s often a good way to trade notes and feedback.

5. Thinking about what you want to do the night before helps make the action automatic the next day. Just allow yourself to change your mind to whatever feels more alive in the moment of creation.

Choose your player: PM edition

Illustration by Elspeth Michaels

Good night!

“I am not a morning person. While I wish I were, I have come to accept my unwavering night owl ways. I realized in this process that I need to live through the experience of the day to start churning ideas; I’m always brainstorming in the background. Doing my creative time after work feels more freeing to dig into my ideas, especially if I want to exceed 20 minutes. Running/exercising forms a core piece to my creative practice, so I like to have time for that before I settle in. It sounds funny, but being tired makes me more loopy and emotional, and for some reason it’s easier for me to tap into deeper, abstract thoughts.” (Questlove writes about this in his book Creative Quest, which I’d recommend!)

My tips:

1. Always carry a sketchbook/notebook with you. If you’re busy traveling or on the go, it’s easier to steal a few minutes here and there to sketch out ideas.

2. When you’re bored or overwhelmed, think about approaching a one-off task in a more creative way. When I cooked ‘yellow meal,’  it was a fun way to take a break from all the ink drawings I had been working on at the time. It tickled a different part of my brain. Sharing that experience with my family also created a meaningful memory.

3. Let fear and curiosity guide you. The more you’re in this space, the more primed you are to confront those more intimidating projects.

4. Consider the idea of “creative cross-training,” a term I learned from Suleika Jaouad from this episode of Life Kit. Try new things and allow yourself to be bad at them. It all flows into the same abundant creative well. (Check out her Substack: The Isolation Journals.)

5. Talk about and share your creative projects! It might feel self-promotional or congratulatory, but it’s not. Either way, who cares?! When you do this, it invites collaboration and builds community. You might get some helpful feedback too.

In the past 2+ years, we’ve been forced to adjust to an exhausting, unpredictable rhythm of separation. I know for me, keeping in touch with people through creative projects offers a kind of healing, consistency, and lifeline during the darker, more isolated days. Also, why does it feel like such a radical thing to give yourself time and permission to do your own creative work? Committing to yourself changes how you feel about yourself. Creative 20 helped me adjust during a transitional time in my life. I had moved to a new city for a remote-turned-hybrid job just as Omicron was popping off. It grounded me in a daily creative release and it deepened a friendship, incrementally and consistently. I’m beyond grateful for that, and I’m looking forward to how this practice evolves.

If reading any of this resonated with you, we hope you try it too in the ways that work best for your life. Feel free to leave a comment if you have any questions, insights, or resources from your own experience. And lastly, thanks Felipe!