On November 7th, my friend Felipe and I hit the 1-year creativersary of us doing something creative every day, a practice we’ve since dubbed “Creative 20.” For a quick recap, we spend 20 minutes (give or take) working on our own various creative projects separate from our 9-5 jobs. Then, we text each other what we did as a way to stay accountable and keep in touch. I wrote about it a few months ago when we hit Day 200, and if you’re curious to learn more about how we started, check out this post: Our 200-Day Creative Streak.
As you can see from Felipe’s tally sheet, we made it to 365 days with no skips, and our streak is still ongoing and immaculate. But to keep it real, I feel compelled to admit the close calls over the past year, like that one night I jumped out of bed in a panic just in time to jot some ideas down in my sketchbook after almost falling asleep. We managed to do it in the quiet of our respective apartments, on trains and planes, through jet-lagged mornings, after fun nights out, early before work, late into the wee hours, during the crunchiest of work deadlines, in defeated moods, on energized highs, with friends and family, feeling inspired, fighting exhaustion—here we are. Through COVID and through health, till death do us art. It started as an experiment, turned into a commitment, settled as a practice, and eventually evolved into a habit. It’s a ribbon I tie around the end of each day, a gift to myself. And for all the days that kicked my ass this past year, I’m really proud of this milestone and of us.
Now, a full year in and counting, Felipe and I caught up last week to talk about what we learned about ourselves, the process, and how our expectations measured up. While most of my Creative 20s have been dedicated to writing this very newsletter, (the product of which some of you have been reading since April—thank you!) I’m sprinkling in a few photos of other projects I worked on as well.
How do you break through what holds you back?
We both reflected on our attitudes around creativity before we attempted this daily goal. Did Creative 20 change our relationship to the things that historically blocked us? We identified overthinking, the fear of rejection, and imposter syndrome as our biggest obstacles.
On Overthinking: Yes!
Felipe: “It’s helped me start more projects, there’s less paralysis to try. I’m pretty sure I wouldn’t have taken on the video project that I'm working on right now, if it weren't for Creative 20. It works the muscle to just take action. Creative 20 taught me how much I really do love drawing. For some reason, I had this story in my head that I suck at it, but now I don’t feel that way as much. It gives me the permission to try.”
Me: “I’m a huge overthinker, and I’m grateful that this helps me push past it. I think inertia plays a factor into creativity too. It used to take me a lot of time and mental energy to settle into starting a project, but now I feel ready and primed to jump in. Especially on busier, more demanding days, I’m a lot better about stealing 5 minutes here, 10 minutes there, making some incremental progress so that it keeps me motivated. For me, having a weekly writing deadline also helps me focus on the time I have, and to move on when it’s time to publish.”
On Rejection: Yes!
Felipe: In theory, Creative 20 does help me with rejection. I’m definitely less fragile mentally and more impervious to what people have to say. I applied to a couple of things this year and I did not feel any psychological pain about not getting them. I shrugged it off, I forgot about it. It’s a nice contrast from early 2021, when rejection would send me into negative self-talk around being not good enough. People write how rejection is a primal fear for humans. It’s not just “no,” it’s a brand of inferiority— you’re exposed as deficient, undesirable. On the most extreme level, you’re cast out from your tribe and left to die. The anxieties of it—I’ll never fully get over that, but with Creative 20, the cost of rejection isn’t high because you have a lot of agency. It’s your own game—you’re always participating, no one can sideline you.
Me: Right! There are no gatekeepers to your practice. Honestly, I’ve gotten rejected from so many things in my life, but in time I’ve appreciated how those ‘no’s’ guided me towards other wonderful, unexpected, and meaningful opportunities. I don’t think the fear of rejection stops me from trying or applying to things, but it can definitely sting and affect my confidence. I had a tendency to stay in those negative feelings longer than I do now. I feel like I’m on my own rhythm of creating and any external criticism or validation feels…irrelevant to that practice. Rejection doesn’t define or change my desire to keep making and sharing my work.
On Imposter Syndrome: Err…kinda? Not really?
Felipe: I was hoping this would help with imposter syndrome, but I don’t think it goes away. I’m more prepared to take chances, but I still have fear around it. I do think Creative 20 disconnects you enough from imposter syndrome to do things in spite of it.
Me: Same—I’m not sure if I feel a difference in how much I feel imposter syndrome now vs. a year ago. It’s something I always have to work at managing. On some level, doing something every day gives me more confidence to identify as the action, i.e. ‘I write, therefore I’m a writer,’ but it’s not always the case. However, I do think a little self-doubt in the right context can serve you—it feels more like a tool now, less of a weapon.
For both of us, our favorite projects included our friends and family, as collaborators and participants. Felipe’s standout from this year was a parody sports documentary he made for his friend’s bachelor party. He premiered it movie-style in a room full of his friends, on a projector with popcorn. They loved it.
Felipe: “I’ve enjoyed a lot of projects this year, but the things I make for my friends are usually a lot of fun. I know they don’t have a lot of standards, and yet I still put so much effort into them not because I want to impress them, but because I want to delight them.”
I spent my favorite Creative 20 days drawing together with my then 5, now 6-year old nephew. It’s totally our thing! We sit together in the kitchen and draw flowers, paint abstract shapes, and build small sculptures. Our current favorite is FIRE CRAYONS, where we light a candle and dip crayons in the flame for a few seconds before flinging the melted wax across the paper. He tells me wise things like, “What’s great about abstract art is that there are no mistakes!” One time when I asked if he wanted to listen to Beyoncé while we drew, he answered, “Yes. Beyoncé is an artist for something else. She’s an artist for music.”
The times when my friends joined me in sketching, writing, or brainstorming ideas became treasured moments and memories too. It’s a bond forged in building ideas together and sharing in a process that’s always slightly vulnerable no matter how long-standing the relationship. These are the Creative 20s when I feel most energized and exposed, totally immersed in the present. On Day 335: Felipe and I finally did Creative 20 together when I was in Chicago. It felt natural but also surreal to be in the same space creating. (We still texted each other after. Again, it’s a habit!)
Our conversation evolved into discussing motivation as it relates to overthinking, the fear of rejection, and imposter syndrome. When did we feel the best in this process? For both of us, the projects inspired by delight and joy, motivated by building connections and making memories proved to be the most meaningful.
Felipe posed these questions, which I kept thinking about after we spoke:
“To me the holy grail is, can you find the drive to push yourself to do things better out of pure enjoyment rather than the fear of not belonging, or feeling undeserving? Or competition? Or is the work rooted in not feeling ‘enough’ or seeking validation from other people?”
If I had any expectations from this past year, it might have been an aspiration to produce more finished, polished work—culminating to that ever elusive portfolio. I feel that way about my writing, 100% due to the support and opportunity provided from my Joel Gay Creative Fellowship. That said, I only felt ready to apply for it because of the momentum Creative 20 generated in my life. It drowned out the noise of overthinking, rejection, and imposter syndrome, and allowed joy and curiosity to ring through. The ‘no’ became ‘why not?!’
Apart from these weekly essays, I haven’t completed most of the drawings and paintings I started. Surprisingly, I don’t feel burdened or disappointed at all by that. What I lack in finished product, I gained tenfold in process and perspective. I have “I want to draw with Auntie!” I have memories of and future plans for collaborations with friends. I have a better relationship with my fears around producing and putting my work out there. I still have imposter syndrome, but it’s at a volume that I can tune out better now, maybe it’ll improve with time.
And I always have hope that even the worst day will get better just by making a little space for myself to express an idea.
Day 377: Fired off this post!
Thanks Felipe, to the next 365.
Thanks for reading.
your art it beautiful!
I always feel so inspired when I read about/see your art. Thank you so much for sharing!!