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Episode 54

How to Fail Forward

Girl Gang Craft the Podcast is back! It’s our first episode of 2023, and we’re excited to be back on the (digital) air.

On this week’s episode, Phoebe takes the mic solo to reflect on some of the experiences that have contributed to her success and personal growth - citing “failures” as a student, early employment, college, and most poignantly, in the process of launching a new business. She explains the extreme discomfort that can come with feeling you’ve come up short - especially in a space you’re passionate about. For Phoebe, that discomfort came from failing her AP Art Portfolio, freshman Environment Science in college, and venturing into the world of biz - craft fair rejections. Long story short, it can feel pretty uncomfortable to sit with shortcomings, especially when they’re happening in a space you’re passionate about.

While acknowledging that failure can happen on a large scale of severity and consequences, Phoebe speaks to her own experiences processing her failures as opportunities for growth, leaning heavily into the need for those creating a business to be able to pick themselves up - no matter how bad it might feel - and try again (or try different!)

Phoebe concludes that the ability to encounter, sit with, and move beyond failure is one of the hardest skills we have to learn - but it’s never without benefit to whatever life throws at you next.

Episode 54



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Phoebe Sherman

“I remember feeling so awful when I got denied from these (craft) shows. It made me question my worth, my work, my plans - my life plans. If I had quit - GGC would not exist today. Maybe I got practice failing.”

[2:48] Phoebe shares some of her “notable” failures from before her life as a biz owner. “I failed my AP art portfolio in high school…I sobbed and sobbed, and was so uncomfortable and upset. I thought I was a failed artist. But now, I'm a full-time professional artist and teacher - so take that college board. I also didn't do so well in Environmental Science freshman year of college - I thought environmental science was going to be my major. But I hated it. Then I found feminist studies. And here we are. So cheers to that.”

[7:30] In the early days of Instagram, Phoebe was determined to brand her first product-based business - what she describes as a “shitty jewelry line.” Her profile pic? A logo she hand-drew - and then took a picture of.

“I was a printmaking major at Santa Cruz, and printmaking requires a lot of big heavy things that I didn't have access to post-college - but I did have access to beads and feathers, and I loved making things with my hands. So I started a jewelry line. This was my first dive into Instagram marketing, my first dive into branding, and my first glimpse into the craft fair world…I hand drew my logo and took a picture of it. That was my profile pic.”

[9:45] “I remember feeling so awful when I got denied from the shows - it made me question my work, my worth, and my plans - life plans. So I decided to throw an event. The first craft fair I threw was at my yoga studio in Alameda. There were just a few of us showing and selling and honestly, the audience was pretty dismal. It didn't feel great.”

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Phoebe Sherman

Failure sucks. But that failure is a part of business - a part of life. The difference between a successful entrepreneur and an unsuccessful one?...The successful ones keep going. They keep trying despite all of the failures - despite the shitty views, the low sales, the unsuccessful launches. They try it again - maybe with something slightly different - and they learn along the way.

Phoebe touches on the importance of not letting low turn-out, views, or pretty much anything - prevent you from making another go at it. In the case of GGC, its success quite literally depended on Phoebe’s resistance to admitting defeat.

“I decided to throw another event at Lucky Dog cafe in Oakland, in August of 2017. I got together with 15 of my maker friends, and had a little event. I knew I wanted it to be femme-forward. And so I called it Girl Gang Craft. I started an Instagram, figured out how to get people there. And that day was magic.”

Bigger ideas, bigger problems
[12:37] While her introductory experiences in the craft fair world took place in small spaces, Phoebe was not prepared for the headaches that came with upgrading her event space.

“Once we got to a real venue, things got complicated…there were conflicts between the venue and the city. I needed the event permit, and the venue owners didn't want me to get an event permit. In their mind they had been paying the fees to the city of Oakland that basically allowed all events - (both public and private) to not need an event permit, fire sign-off, and insurance. Things got complicated and tense. There were emails, calls - it was so stressful. I thought I wouldn’t be able to have this event. I remember thinking, “I’ll be letting all my vendors down and letting all the market-goers down, and it’s going to be embarrassing, right?”

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Phoebe Sherman

[16:16] Despite being unable to resolve the permit issues between her venue and the city, she decided to play it cool and let the venue make the calls with compliance. While she doesn’t recommend it, staying under the radar paid off.

“I learned a ton about the bureaucracy of the city. I learned about event permits, fire permits, and ABC permitting. I’m not telling you to break the law, please and thank you. But I am saying there is a learning curve in these systems. I learned about working with venues and advertising for events and making layouts - I learned that there's often a way forward.”

[19:34] Phoebe’s got a decent amount of craft fair success under her belt since her small-time days in the Bay Area. But she still faces feelings of failure with online launches - explaining how difficult it can be to anticipate the kind of marketing, subject matter, or delivery that is going to make for a successful online course.

“My last failure - or at least my most recent - (because it certainly won't be my last) was my Reels course last fall. Or at least, it really felt like a failure. I'll tell you these launches eat me alive. It's terrible. I have circular thoughts. I'm constantly checking my social networks, constantly checking my social metrics, constantly refreshing the landing pages. Maybe it's because I'm putting a piece of myself out there - maybe because these launches are relatively new offers.

“I launched the course, I got about three signups. This was devastating. Why did such a low percentage of participants from the challenge sign up for this class? Maybe it was the price…we did offer payment plans. So maybe it was the timing. Folks didn't want to commit to the six weeks. Maybe y'all hate video? I'm not sure. I'm still not sure.”

Despite low turn-out, Phoebe treated it as a beta-opportunity - and ended up having a blast, getting the opportunity to educate - something that brings her serious joy.

[23:32] “I was ready to cancel the whole thing. But I did treat it as a beta class, I invited a few of my peers into the class to try it in exchange for feedback and testimonials. And honestly, the class was great. The students learned so much - I had so much fun, because I love
Teaching.”

[22:52] She ended up with some valuable lessons, too. Or at least a plan for next time.

“What did I learn from it? I was going to do it again. But a lower ticket offer, and less time commitment.”

Follow GGC founder Phoebe Sherman's personal journey @phoebesherman on Instagram.
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