Transition to a Freelance Career: Lessa Chung’s Creative Liberation

Written by Christine Warner on April 5, 2017

“I find that I am more decisive about my vision as a freelancer. In a full-time environment, there were so many ‘cooks in the kitchen’ that I often sacrificed my vision to satisfy the larger group. My product has my conceptual thinking behind it, so I am ready to stand by it more firmly.”

Tokyo-based art director Lessa Chung’s creative career took off in New York, where she worked for several advertising agencies focusing on digital and social content. After her transition to a freelance career, she now splits her time between freelancing and language school in Tokyo, and she plans to start a master’s program in innovation design in the fall.

Lessa Chung, art director

During her agency days, Chung eyed freelancing but felt intimidated by the unknowns and balancing act. “Throughout my time working at ad agencies, I had multiple friends who made the jump. I initially envied it as this very brave, very impossible thing. I tried to dabble in freelance while working full-time, but found it impossible to balance.”

The Decision to Switch Is Often the Hardest Part

After further exploration, insights from friends and experts proved the transition to a freelance career was doable, lucrative and liberating. “To ensure my dive into freelance life wouldn’t be the end of me, I asked so many questions,” says Chung. “My freelancer friends were incredible resources. They were insightful, supportive and — most importantly — honest.”

Talented freelancers she met while attending the Secret Handshake Conference at the Art Directors Club in New York shared similarly realistic yet encouraging perspectives. This support chipped away at her doubts. “Once it didn’t seem impossible, it became a question of when.” When she and her partner decided to move to Tokyo, she took the plunge.

Healthy Work-Life Balance Inspires Creativity

Chung left her full-time role to prepare for the move and started to pick up freelance gigs. “It felt amazing and empowering. It countered all my initial misgivings and confirmed I could actually do this.” The ability to control her schedule and take time between projects to renew her creativity was refreshing in contrast to the grueling pace of agency work.

“I line up projects in advance to make sure I’m busy but not overwhelmed.” While she misses the camaraderie of full-time work, being her own boss taps diverse skills through full ownership. “I’m my own creative director, designer, accountant, finance person, etc. I enjoy having a hand in everything, because it’s made me take pride in what I do.”

The Reach of Digital and Personal Connections Brings in Work

Establishing a steady stream of clients was one of Chung’s initial concerns. “The idea made me so anxious. I’m also not a big fan of small talk or advertising my own skills. How could I effectively sell myself as a business?” She turned to social media and online networks to showcase her skill set and reached out to past professional connections to kick off her first projects.

“I updated my LinkedIn description to boost that SEO, became more active with my Working Not Working profile and redesigned my portfolio site,” she recalls. “I also joined a few freelance-specific networks to expand my reach and line up new opportunities.” Chung was surprised to find a wide variety of freelance environments: short-term, long-term and surplus work.

To anyone considering the transition, Chung advises just going for it. “It’s not impossible, but be practical about it. And be ready to be an active advocate for yourself and your career.” You can always return to a full-time environment if it’s not a good fit. In the words of Chung, “You have the power to steer your path forward.”

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