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Bob Ross-Inspired Painting: A Creative Team-Building Event with Pinterest, Hosted by Dragonfly Designs

At Dragonfly Designs, we believe that creativity is a powerful tool for building connections, which is why we love hosting group events for budding artists of ALL ages! This was beautifully showcased at a special corporate event for Pinterest employees from their Palo Alto and San Francisco locations. Our larger team, led by the talented Art Instructors Tamara and Hamilton, guided participants through a unique and immersive experience inspired by the legendary Bob Ross. The result? A group of hard-working professionals were transformed into passionate artists for the day!

Channeling the Spirit of Bob Ross

A fan of Bob Ross since her teenage years, Tamara immersed herself in his world to prep for the occasion: “I’ve watched Bob Ross for years on TV, but being Bob was a whole different thing.” To truly capture his essence, she watched countless episodes of Bob Ross on TV to get ready for the event. As you can see, from the iconic puffy wig to the 70s-inspired bell-bottom jeans, she embraced the role with enthusiasm!

Through her preparation, she noticed how Bob Ross’s teaching style evolved over the years—from a more structured approach to one that exuded creativity, love, and acceptance. This transformation in his style was something she wanted to convey to the participants. “I wanted them to take away that feeling and create a piece of artwork they could be proud to hang on the wall at home,” she shared.

Bringing Art to Life for Beginners

Also embracing the spirit – and attire – of Bob Ross, Hamilton focused on making the experience accessible and enjoyable for everyone, regardless of their artistic background. He spent time understanding the medium, practicing techniques, and drawing inspiration from Bob Ross himself. “My goal was to get the participants to have a good time, but also to walk away with the confidence that they too can learn to do art and that it’s not intimidating,” he explained.

For many participants, this event was their first foray into watercolor painting, so Hamilton emphasized the forgiving nature of the medium, encouraging beginners not to stress. “Just build up slowly, starting from your lightest values, then layering and layering to get beautiful contrasts,” he instructed them.

 
A Day of Creativity and Connection

The event was filled with moments of joy and discovery. Participants stepped out of their comfort zones, trading their usual tasks for paintbrushes and palettes. The instructors loved seeing the concentration and determination on each face as they guided them through the creative process. 

“My favorite part of the event was interacting with the courageous people who came out of their cubbies to become artists for the day,” Tamara recalled. Hamilton added, “Watching people’s art unfold and seeing their concentration as they tried to replicate certain techniques was really fun and inspiring!”

Takeaways for Aspiring Artists

For those new to watercolor, our instructors have some Bob Ross-inspired wisdom to offer. “Have fun, keep at it, and remember that painting is like any other skill—you get better with practice,” said Tamara. “Don’t stress about it too much,” Hamilton added. “The medium is very forgiving; you can always use water to wipe away pigment if needed.”

Hosting a Group Event with Dragonfly Designs

At Dragonfly Designs, we are proud to help people unleash their inner artists. This Bob Ross-inspired event was not just about painting; it was about fostering creativity, building confidence, and creating lasting memories. Our team is passionate about bringing artistic adventures to life and would love to hear about your vision for an upcoming gathering. Click here to learn more about hosting a group event with us, then contact us to start planning a fun event for your team, friends, or family!

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