A Tale of Becoming Two Jeffs

A look back on the 4 times I did each of the Inkygoodness 28-Day Challenges

I partook in a bunch of 28-day illustration challenges hosted by Inkygoodness over the last year. Four, to be exact!

The way it worked was quite simple: our host Lisa invited real industry folks to set mock creative briefs, and we all did our best not to turn into Tonya Harding as we competed for prizes like commissions and mentorships. The 28 days included masterclasses from other illustrators, regular workshops with each other, and live feedback sessions from the pros.

Granted, I felt like how Jeff Goldblum looks in this for about 60% of the time, but I like to think I have more to look forward to these days.

#1: The Editorial Challenge

The very first challenge I did was the 28-Day Editorial Challenge in April 2023. It was mayhem right from the beginning. The mock briefs were for three wildly different publications, ranging from a culture & lifestyle magazine to a spread in a kids’ magazine. The whole thing felt like being in an American Idol audition.

For Frankie Magazine’s brief, “History’s Deadliest Garb”

I was hopeful, but as soon as folks started sharing their initial drafts, I felt doomed. I pushed on with a sense of dread at some points, but learned things about myself:

• I worried too much about impressing literally everyone, and that actively worked against me. The more I tried to mold my work into the judges’ expectations, the worse I felt.

• I took it too personally when I felt overlooked by the judges. I sat with the dark feeling for longer than I should have.

Yikes. Was this what a midlife crisis felt like?

I survived the first challenge, but came out with shaky legs. I had never been pitted against 150+ people for one task before. I felt a little disappointed, but at the same time, I was surprised by and proud of the work I produced.

#2: The Branding Challenge

In July 2023, the next 28-day challenge focused on branding for a fictional music festival and an alternative meats product campaign.

I put most, if not all, of my energy in developing my technical skills further. I admit that the conceptual side of things suffered. But boy, was I having the time of my life with these digital textured brushes.

Poster for Oat Studio’s fictional music festival

The pressure got to me by the end, and I felt like I delivered a mixed bag. Some pieces I loved, others I was happy to exclude from my portfolio. I mean, slabs of alternative meats posing with vegetables for a family Polaroid? I wasn’t even drunk or anything when I thought of these.

For Fiasco Design’s alternative meats campaign “Curious Meats”

#3: The Packaging Challenge

November, 2023. Tired of feeling like a loser, I made a promise to myself this time around. I approached the briefs like I did with invitations to dinner parties with friends-of-friends: I wasn’t there to impress. I was there to get drunk on my “Staff Picks” wine and have a good time with strangers.

Surprisingly, with that slight adjustment to my mindset, I found a looseness and brightness to my work that seemed to resonate. I opened up to the new friendships I had made, and spent more time getting to know other artists through their work. So much more enjoyable!

Coffee packaging for a fictional Australian roaster for Lynn Bremner

This piece stood out for a bonus brief, and was commended by illustrator Lynn Bremner in the end. The pride I felt stuck with me, and this marked the point where I felt like I was finally getting the results that I had been looking for.

It had all the notes I wanted to hit: composition, technique, and story.

Similarly, this piece for a fictional hot sauce brand made an early impression for similar reasons. Unfortunately I wasn’t quite there with the final execution. I fell down at the very end, struggling with the challenge of fitting all the details of my work into a sticker that was no smaller than a large Post-It.

Lita Rita hot sauce label for Wonderkind Co

#4: The Branding Challenge, Part 2

In the last challenge that just ended this May 2024, I had an opportunity to try again. It had been a full year since the first one in April 2023.

Outside of the 28-day bubble, I was working out my own pathway into children’s illustration, book covers, and longer narrative projects. I decided to use this time as a vehicle for my own goals, understanding that what I delivered may not be fully in line with the creative briefs.

With the glitter of my previous attempts still stuck on my fingers, I once again shuffled into the room carrying no expectations. I had no other agenda but to make friends and have a good time. Time to bust out the “Staff Picks” wine again!

I loved this piece, which wasn’t chosen, but something I definitely planned to repurpose into something more appropriate for my portfolio:

For Vault49’s tequila seltzer brand

Nobody’s work was better or worse than mine. But some were just more aligned to the specific ask. The judges and mentors were just as diverse as we were, and it took four installments of these challenges for me to finally get it.

“Strikes and gutters, ups and downs.”

I needed to focus on the long game, and I’m really glad I did. Again, I didn’t win any commissions with fancy agencies or 1:1 portfolio meetings. Expecting to hit the target for each and every brief was unrealistic and somewhat delusional. I mean, you don’t go on Tindr expecting to swipe right 100% of the time, do you? Otherwise, my friend, may I suggest a different platform for you? Even Jeff Goldblum had to live with a tumultuous IMDB filmography—and he was all the better for it!

It wasn’t really about winning the challenge—but about people finding the right fit. The key to me was to keep producing, building a body of work that I could edit and refine over time.

These challenges felt like little pressure cooker environments, and each time I came out of them with something different. Not well-cooked or well-presented, but at the very least something that went through some kind of process to transform into something that wasn’t there before. I developed a brighter outlook and confidence in my work, as well as a more solid sense of community.

I enjoyed jumping into these a lot, especially seeing myself grow as an artist in my first year—and having several portfolio pieces to show for it. I ended up with twelve projects in one year! And all of them free for me to revisit and refine as I keep going.