Design Week Portland Freelance Freelancing

"You don’t realize how lonely independence is": the benefits of a little 'Overshare'


By Doug Zanger, Americas Editor

April 25, 2016 | 7 min read

On the surface, a sprawling warehouse doesn’t seem like the place to gather a few hundred creatives to intimately discuss some very personal stuff related to work — especially for freelancers. But freelancers are cut of a slightly different cloth, and tend to gravitate towards each other. Thankfully, the pervasive sentiment among freelancers is that it is good to share their ups and downs.

There is obvious competition, but the adage of “a rising tide lifts all ships” seems particularly apt as the freelance economy in the US continues to grow (according to the Bureau of Labor Statistics, 15.5m people in the US were self-employed in May 2015).

XOXO Outpost was actually the perfect venue — as Working Not Working hosted (and recorded for podcast) their Overshare series during Design Week Portland (DWP) in Portland, Oregon. A relatively new addition to the scene, Overshare’s first foray was last February in New York City and featured, according to Working Not Working’s Facebook page, “art directors/designers/lovers” Leta Sobierajski and Wade Jeffree. Their second, in March (also in New York City) was led by “designer/lettering artist/super nice guy” Jon Contino.

The special Portland version included illustrator, educator and collector Kate Bingaman-Burt (also one of DWP’s board members); Adam Garcia, creative director, designer and illustrator at Portland-based studio The Pressure; award-winning artist and designer Rich Tu; and co-founder of Working Not Working, Justin Gignac.

For the uninitiated, Working Not Working is a well-respected, invite-only community of top creative talent (mainly in NYC, LA and San Francisco) that facilitates creative love connections with agencies, brands and collectives. Founded by Gignac and Adam Tompkins, they count the likes of Wieden+Kennedy, Droga5, Facebook, Airbnb, Goodby Silverstein & Partners, 72andSunny and many more creative companies as part of their roster.

As host, Gignac deftly made topics that could be uncomfortable - such as mistakes, ruts, fears and failure - less agita-inducing. Granted, the panelists were of good humor — but the things they talked about were serious and likely on everyone’s minds. The big doses of candor that the crowd enjoyed were most welcome.

Garcia, for example, “was living in Philadelphia for two years on a mattress that I found in an alley. Now, I’m here with you guys,” noting that “those were dark, dismal times.”

Bingaman-Burt shared her constant fear of “just letting people down, almost to a detriment to my own well being, I think. I don't want to let people down.”

One of Tu’s issues was around when he could move out of his parent’s house, saying, “You leave school, you're $80,000 in debt, and then you want to be an illustrator. It's absurd. How are you ever going to make that back?”

It’s well worth listening to the upcoming podcast, because one could likely pick a few relatable and universal issues of their own — no matter the discipline — and find both realism and optimism.

There were particularly enjoyable parts of the discussion where Tu got into a snowman metaphor (“Once you start a career, once you get that ball rolling, then balls turn into snowmen and snowmen turn into, I don't know, abominable snowmen. Once you get on that track, then you realize, ‘Oh, this is a career."). Bingaman-Burt bemoaned the lack of tall bikes in Portland (it had to do with Portland’s penchant for all things weird) and Garcia praised the openness and welcoming nature of Portland.

Once the mics turned off, all four were accessible, honest and willing to spend some time with the 250+ people in attendance — their collective wisdom an important part of not just “who” they are but “why” they are.

“You don’t realize how lonely independence is,” said Gignac. “When I first started freelancing, I went to all my friends and I would say, ‘Oh my God, freelance is the best.’ You like hyping it up because you feel really great and getting a good check and all that. Then there is the reality. There's weeks that go by and there’s no gig and ‘what am I doing?’ Then there are also days that I'm working from home by myself and my wife comes home at seven o'clock and I'm like a puppy, running to the door because I haven't talked to another human being.”

Gignac pointed to the other three panelists as examples of the tenuous thread that is freelance life.

“I think the importance of things like this is letting people know that (freelancers) are not that unique and we are all going through the same stuff,” noted Gignac. “Even though these (panelists) are amazing and incredibly successful, they are really open about their struggles, which I think a lot of people can relate to.”

Garcia, for example, was very honest about his fears.

“(Freelancing is) always scary,” admitted Garcia. “I’ve kind of been addicted to the feeling of being scared. When I start feeling safe, when I start feeling protected, then all of a sudden I start losing interest and I just start hating whatever it is I'm producing. I don't feel like I have that edge, so really fear brings an edge to the things that I do.”

The common theme that came out of both the public talk and the private conversation among the panelists was that of humanity and togetherness. Bingaman-Burt, who has been a teacher for a number of years, espoused the importance of the “team” and “nice” mentality to her students.

“(I tell my students), two things,” said Bingaman-Burt. “You have to be working together and you need to be kind and empathetic. You’re probably going to be working with the same people once you graduate, so it’s good to be considerate. There will be criticism, but it’s okay as long as it’s constructive.”

Perfection is another bugaboo that torments creative professionals, but especially freelancers, since a constant flow of work is vital. Gignac, however, sees it in a slightly different light. To him, it’s more about self-awareness.

“There is a book called, 'The Gift of Imperfections' and the author, Brené Brown, had a thing in there about the difference between fitting in and belonging,” said Gignac. “Fitting in is changing yourself to be loved and accepted and belonging is being yourself and being loved and accepted. That was a life-changing thought for me. I thought, ‘Oh! I have been trying to fit into a lot of aspects of my life where I should just be myself.’ I'll find where I belong and I think that is where most people get hung up.”

Though there are certainly some distinct rewards, freelancing can be a lonely game. However, as evidenced by the discussion, there is an open, welcoming and supportive community at the ready as long as, according to Gignac, the most important person in the equation is cared for first.

“You are your true self and I am my true self and we all find where we belong, and then, things are pretty great.”

Photo credit: Aaron Lee

Design Week Portland Freelance Freelancing

More from Design Week Portland

View all


Industry insights

View all
Add your own content +