The Early Days: The Doubt, Dreams, and One Spark of Curiosity

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Jessica Walsh’s journey into design wasn’t perfectly mapped out. In fact, it began like most creative careers do—out of curiosity, experimentation, and an undeniable need to create.

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While other kids spent afternoons outside, Jessica was glued to her family’s clunky computer, teaching herself how to code and design websites for fun. She wasn’t trying to make money or win awards—she was just playing. But that play planted the seeds of a creative career that would one day inspire thousands.

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Fast forward to design school. Jessica’s talent was clear—she was the student who stood out. While others stuck to the rules, Jessica pushed boundaries with work that was colorful, daring, and full of emotion. But even the most talented graduates face the same daunting questions:

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• How do I stand out in an oversaturated industry?
• Will anyone take me seriously as a designer?
• What if I fail?

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Jessica’s first job out of college was in corporate design—a steady paycheck but a far cry from her creative aspirations. She felt stuck. The work was uninspiring, and her days blurred together in monotony. The spark that had made her fall in love with design was flickering.

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“I was miserable,” she later admitted in interviews. “I felt like I was creating for someone else’s vision, not my own.”

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That’s when Jessica faced her first major choice: stay safe, or take a risk?

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The Leap: Saying Yes to the Unknown

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Jessica’s big break came with an opportunity that most young designers would find paralyzing. At just 25 years old, she got the chance to join Stefan Sagmeister—a design legend—at his iconic studio, Sagmeister Inc.


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Stefan had noticed Jessica’s work and recognized her raw, fearless creativity. He didn’t just want her as an employee—he wanted her as his partner.

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Imagine that. At 25.

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It was a daunting offer. Sagmeister Inc. was already a big deal in the design world, and stepping in as a partner meant enormous pressure:

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• Could she hold her own alongside a giant like Stefan?
• Would people take her seriously?
• What if she messed up?

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But Jessica said yes—despite the doubts, despite the imposter syndrome. That decision changed everything.

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Fearless Work: Redefining Modern Design

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Together, Jessica and Stefan rebranded the studio as Sagmeister & Walsh, and Jessica wasted no time leaving her mark.

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She brought a new energy to the studio—work that was bright, conceptual, and unapologetically bold. Her designs were fearless, blending vivid colors, playful elements, and deeper storytelling in ways that grabbed attention and refused to let go.

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Here’s where her approach stood out:

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• She broke the “rules.” Jessica didn’t conform to the quiet, minimalist trends of the time. Instead, her work felt alive—vibrant, emotional, and unmistakably human.
• She took risks. While other studios played it safe, Jessica wasn’t afraid to create work that sparked conversation, even controversy.

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One of her earliest standout projects was the Aizone campaign. Instead of designing conventional ads for a luxury retailer, Jessica transformed typography into art. She paired bold letters with real-life models, creating visuals that felt like museum pieces—alive, colorful, and impossible to ignore.

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The campaign set a tone: Jessica Walsh was here to change things.

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The Power of Personal Projects: 40 Days of Dating

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Jessica didn’t just create for clients—she also created for herself. And one personal project in particular went viral in a way no one expected.

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In 2013, Jessica and fellow designer Timothy Goodman launched 40 Days of Dating, a creative experiment that turned heads worldwide. The concept was simple: Jessica and Tim, both single and unlucky in love, would date each other for 40 days and document the experience in real-time through design, writing, and visuals.

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Each day, they shared raw, honest reflections paired with beautifully designed graphics, art, and photos. The project was:

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• Deeply human: It explored love, vulnerability, and heartbreak in ways people could relate to.
• Visually stunning: Every day brought new, inventive design work that turned emotions into art.
• Authentic: Jessica wasn’t afraid to share the messy, imperfect side of herself.

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The result? It blew up.

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• Millions of readers followed the project online.
• Media outlets like The New York Times and Time Magazine covered it.
• The project earned a book deal and talks of a Hollywood adaptation.

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But beyond the numbers, 40 Days of Dating proved something powerful: Personal projects matter. Jessica showed that sharing your authentic voice—your fears, your experiences, your quirks—can create connections and open unexpected doors.

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“40 Days of Dating taught me that vulnerability is strength. When you share something real, people respond.”

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Going Solo: Launching &Walsh

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After years of success at Sagmeister & Walsh, Jessica felt it was time for a new chapter. In 2019, she launched her own studio—&Walsh—one of the few creative agencies in the world led by a woman.

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Starting fresh wasn’t easy. Jessica knew the challenges:

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• She was stepping out of Stefan’s shadow.
• She had to prove that her success wasn’t luck—it was hers.

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But Jessica leaned into what she did best: creating bold, emotional work that made people feel.

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At &Walsh, she continued pushing boundaries, working with brands like:

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• Apple: Helping one of the world’s biggest brands stay playful and human.
• Levi’s: Telling timeless stories with fresh, contemporary energy.
• Adobe and Snapchat: Pairing cutting-edge technology with storytelling that felt real and relatable.

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Through it all, Jessica’s mission was clear: to create work that wasn’t just seen but felt. Work that told stories, sparked emotion, and demanded attention.

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The Results: Creativity Meets Impact

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Jessica’s career isn’t just about awards or clients (though she has plenty of both). It’s about proving what’s possible when you’re bold enough to:

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• Trust your instincts.
• Share your voice.
• Create work that’s unapologetically you.

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Here’s what Jessica has built:

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• Global Recognition: From Adobe to Apple, Jessica’s work has shaped some of the world’s biggest brands.
• Viral Projects: Personal work like 40 Days of Dating and experimental campaigns have inspired a new generation of designers.
• A Studio That Breaks Barriers: &Walsh isn’t just about design—it’s about storytelling, empowerment, and redefining what creative leadership looks like.

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But Jessica’s biggest achievement? She’s created a blueprint for creatives who want to do more than “fit in.”

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Lessons from Jessica Walsh’s Journey

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Jessica’s story is filled with lessons every freelancer can learn from:

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1. Take the Scary Opportunities
   • At 25, Jessica said yes to being Stefan Sagmeister’s partner—even though it terrified her. That leap set her career in motion.
   • Lesson: Growth happens when you take risks before you’re ready.

2. Blend Personal and Professional Work
   • Projects like 40 Days of Dating started as experiments but became career-defining moments.
   • Lesson: Your personal voice is your superpower—don’t hide it.

3. Boldness Sets You Apart
   • Jessica’s work refuses to be ignored. Her bold, fearless style is what makes her unforgettable.
   • Lesson: Don’t water down your vision to please everyone.

4. Vulnerability Builds Connection
   • By sharing her process and imperfections, Jessica built a brand people trust.
   • Lesson: People don’t just connect with work; they connect with the person behind the work.

5. Create Opportunities, Don’t Wait for Them
   • Jessica didn’t wait for the “right” job or the perfect moment—she made her own path.
   • Lesson: If the door doesn’t exist, build it yourself.

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Final Thoughts: Your Bold Next Step

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Jessica Walsh’s story proves that creativity thrives when paired with courage. She wasn’t afraid to take risks, share her voice, and create work that mattered—no matter how scary it felt.

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And here’s the truth: You can do the same.

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Your next opportunity isn’t waiting around the corner—it’s something you create. So take the leap. Share your process. Start the project that’s been sitting in your head.

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Because, like Jessica, you might just inspire the world.

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Feeling Inspired? Here’s What to Do Next:

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1. Start a Bold Project: Whether it’s a case study, a passion project, or something experimental, just start.
2. Learn from Jessica: Check out her studio, &Walsh, for inspiration.
3. Get Tools to Grow: Usefreelance kit has resources, guides, and tools to help you take your freelance career to the next level.
4. Your next big opportunity starts with one bold step. Take it.