This New Awards Show Is Exclusively Honoring Side Projects

Judges include chief creative officers from BBH, TBWA and VMLY&R

Instead of client work, The Side Show will reward projects created outside of working hours. Side Show
Headshot of Minda Smiley


If you have a quarantine side hustle that you’re particularly proud of, you just might be in luck: A new awards program opening submissions this week is solely focused on honoring—and giving cash prizes to—creative projects done outside of work.

The Side Show was founded by Josh D. Weiss and Sunita Deshpande, both freelance creatives in the advertising industry. Earlier this year, the two collaborated on a children’s alphabet book that features illustrations of animals. While discussing other projects that they could potentially work on together this summer, they came up with the idea for The Side Show.  

Agencies more or less expect creatives to have side projects in the works, according to Deshpande. She said The Side Show provides a way for them to show off what they’ve been up to outside of their day jobs and be potentially rewarded for it.

“We really think those side projects should be celebrated since creatives are now being asked for them anyway,” Deshpande said.

There are 10 categories that people can submit to, some of which include visual arts, music and podcast. Requirements for each category can be found on The Side Show’s website. Each submission costs $10, except for those submitted to the social good category, which is free. The deadline is Oct. 9.

In terms of cash prizes, Best in Show will receive a minimum of $500, while category winners will take home at least $100. However, Weiss said these figures could increase depending on how many entries, sponsors and donations The Side Show receives.

Students who wish to participate are being asked to respond to a brief: “Create a side project that positively impacts the mental health of creatives in the ad game.” Those who submit an idea will be charged $5. The winner will receive mentorship and portfolio review opportunities.

As of now, Weiss and Deshpande are covering the costs for The Side Show themselves, but they are actively looking for donations and sponsors. Mt. Freelance, an educational program for freelancers founded last year by two former Wieden+Kennedy creatives, has agreed to serve as official sponsor and provide the $500 Best in Show accolade.

Weiss said all the money The Side Show receives that doesn’t directly go toward covering expenses, such as maintaining the website and running sponsored posts, will be funneled into the awards.

“As soon as we hit that break-even point, every dollar is going to go back towards the prizes,” Weiss said.

Roughly 50 judges have agreed to participate in the inaugural awards show. The chief creative officers of TBWA\Chiat\Day New York, BBH New York, VMLY&R Kansas City and Erich & Kallman are taking part, as are a number of executive creative directors across the country.

Other judges include Keni Thacker, founder of 100 Roses From Concrete; James Kinney, Mother’s chief talent officer; and Aisha Hakim, founder of Fellow, an app for women who work in advertising.

Judging, which begins Oct. 18, will occur in two phases: The first set of judges will select shortlisted work, while the second group will determine overall winners.

Winners will be revealed during a virtual event called Creativity Week that Weiss and Deshpande are finalizing details for. Scheduled for the last week of October, the event will feature panel discussions and workshops. Invisible Creatives founder Maddy Kramer, as well as Pimp My Portfolio founder Camilla Ciappina, are a few of this year’s speakers.

Deshpande said she was in part inspired to start The Side Show after reading a Medium post by copywriter Brooke Strozdas that essentially tried to make the case for why agencies shouldn’t expect creatives, particularly younger ones, to have side hustles.


@Minda_Smiley minda.smiley@adweek.com Minda Smiley is an agencies reporter at Adweek.
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