TL;DR:Cait Lam built a creative career rooted in joy and service, designing accessible branding for small businesses while sharing her process online. When financial pressure threatened to stall her mission, Dare to Dream gave her the stability and validation she needed to keep going without compromising her values. Keep reading to see what’s possible with the right support, and enter this year’s Dare to Dream Challenge for your chance at $100K.
When Cait Lam walks the streets of New York City, she doesn’t just see sidewalks and storefronts—she sees an open canvas. As a sketch artist, brand designer, and Creator, she has built her career on the belief that creativity should be fun.
For Cait, a Dare to Dream 2025 top five winner, content creation is less about optimizing for the algorithm and more about using her art as a way to tell a story. This belief—that joy and consistency eventually create their own luck—has guided her from experimenting as a Creator during the pandemic to making it her full-time career.
She’s become best known online for her videos designing logos, sketching strangers, and documenting the behind-the-scenes of her creative life. And her business is grounded in service: she keeps her rates low to support small businesses, and uses her platform to give opportunities to those who wouldn’t otherwise have access to professional branding.
Here’s how Cait built a purpose-driven creative career and how Dare to Dream helped her keep going.
The Path From Creative to Creator
Cait is a New York–based sketch artist, brand designer, and Creator who built her career through social media. Showing up on camera wasn’t a sudden pivot—it felt natural. She credits this to her upbringing: her dad was a photographer, and she and her younger sisters often filmed vlogs and edited photos in his studio.
But the real turning point began in the early days of COVID-19. After getting sent home from her sophomore year of college, Cait seized the opportunity to build something of her own. She challenged herself to an ambitious goal: posting content every day for 30 days.
At the time, she wasn’t a professional graphic designer—she’d only ever designed for clubs at school. But she decided to use the challenge purely as practice, creating fake projects for celebrities. It didn’t feel like work—it was just fun to pretend she was a famous designer.
Her consistency paid off. Around day 27 of the challenge, one of her projects went viral. Suddenly, she was landing her first real design clients and bringing in projects from social media.
That’s when Cait realized that in today’s world, clients looking for a designer aren’t searching Google—they’re finding someone whose process and style resonate with them on their explore feed. So she set out to build a freelance design business, backed by a Creator career that documents her work.
The Harsh Realities of Freelancing in NYC
After finding early success, Cait pursued her lifelong dream of moving to New York City. She diligently saved money to make it happen, but it didn’t take long for the harsh realities of being a young, self-employed freelancer in the city to set in.
Cait found herself in a financial crisis. She faced several painful, expensive lessons—everything from unexpected tax bills and fines for lack of health insurance to disastrous contract terms that left her waiting for months to get paid, or not getting paid at all.
She ran through her savings so quickly that she had to drain her Roth IRA early, which triggered even more taxes. She was broke and scrambling to cover her rent.
“I was like, oh my gosh, I’ve run through all my money. Like, I actually have nothing left. And I have rent coming up.”
Despite financial pressure, Cait’s commitment to service never wavered. She gained massive community support and became known for her distinct style, sketching strangers and revamping the branding of local small businesses.
She documented everything, sharing her process on social media. The videos of local cafés repeatedly went viral and became the backbone of her creative brand.
Helping small businesses she loved felt incredibly rewarding. The only catch? They rarely had the budget for extensive branding, so Cait often spent long periods on projects without earning much for the work.
Staying Mission-Minded: Cait’s Submission
Entering the Dare to Dream Challenge wasn’t just about winning a prize, but continuing her mission. Cait didn’t want to pivot from designing accessible branding for local businesses that couldn’t afford big-agency rates—but financially, she was struggling to keep going.
“I thought if I could set myself up financially, I could maintain my rates for these smaller businesses and continue to work with them.”
The prize money would give her the breathing room she desperately needed to continue serving her community without burning out.
In her submission video, she detailed how she’d use the winnings to launch a “logo lottery,” offering full, professional branding for free to a random small business each month. Instead of sharing broad generalizations, she broke down her specific action plan and made her entry sound less like a pitch and more like a genuine promise to her community.
Dare to Dream Top 5: What Winning Meant for Cait
When Cait found out she was a Dare to Dream winner, she was relieved. Although she didn’t win the grand prize, the $10,000 helped offset some of the financial pressures she was facing, giving her stability so she could focus entirely on her creative pursuits.
As a freelancer struggling in a high-cost city, the funds went straight to covering her rent (which she says was a godsend).
But for Cait, the most impactful part of winning was feeling seen—that thousands of people believed in her concept, style, and mission. After sharing her submission video on social media, she’d received an outpouring of community support. And now, being selected as a winner gave her added validation.
The momentum following Dare to Dream was tremendous. Her video sparked massive demand for her logo lottery—bringing in thousands of submissions from thriving small businesses, struggling enterprises, and even student clubs.
It also kickstarted a new phase of business growth, generating so much branding work that Cait found herself financially stable enough to continue working with local small businesses.
Moving Her Mission Forward
Since Dare to Dream, Cait’s business has stabilized, and her audience has continued to grow, bringing in a steady stream of design clients. She’s been able to visit pop-ups in Boston and New York, travel to Canada, and see her logos printed on coffee cups and storefront windows—reminding her of the impact her work has beyond the screen.
And she’s proud of the fact that despite this growth, she hasn’t raised her rates. She intentionally keeps her work accessible, so she can continue supporting the small businesses that need it most. Today, her design and logo work serve a different role in her life—not as her primary source of income, but as a way to stay rooted in the community that has given her so much.
That stability has also allowed Cait to protect the part of her work that matters most to her: joy. Rather than letting pressure dictate her process, she’s found ways to keep the act of creating sacred. When she sketches strangers, she focuses entirely on the moment, then documents the process later. It’s Cait’s way of maintaining her creative spark without letting the need to appease the algorithm spoil the art.
“When I’m out sketching people, I don’t record a single thing. I just sit out there and draw and have the time of my life. And then I go back, and I record myself going in and drawing a line here and a line here… and that really helps me maintain the joy in all of it.”
What the Right Support Can Do for Your Dream
Cait entered Dare to Dream at a crossroads—financially stretched, emotionally invested, and determined not to give up on the work she believed in. Winning didn’t change who she was or what she wanted to build. It simply gave her the stability and validation to keep going, without compromising her values.
Today, Cait still designs accessible branding for small businesses and prioritizes joy in her process. The difference is she’s no longer doing it from a place of constant financial strain and self-doubt, but from a place of momentum and confidence.
If you’re in a similar position—where you believe in what you’re building, but need support to keep going—this is your sign.
We created Dare to Dream to support creatives like you who have a vision but need the backing to build it: Financial resources. Structured support. A real community behind you.
So share your dream—the business you want to build. The impact it could have. And discover what can happen when you choose to bet on yourself.
👉 Enter the Dare to Dream Challenge for your chance to win $100K
Follow Cait’s journey:
Stan Store: Cait’s Stan Store
Instagram: @caitshouse
TikTok: @caitlinnlam
YouTube: @caitshouse
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