Her Story
About Tamara
Tamara Bissell is the founder and creative force behind Pithitude and Donna Lake LLC, where she combines illustration, writing, humor, and entrepreneurship to create distinctive products that connect with audiences through wit and relatable storytelling. Her giftware business features a diverse range of illustrated products, including magnets, dish towels, T-shirts, hoodies, drinkware, and other unique gifts. Tamara began her entrepreneurial journey in 2010 by selling sarcastic illustrated buttons on Etsy as a creative outlet during a period of personal grief. What began as a small creative endeavor evolved into a thriving Oregon-based business, formally established in 2017, with a retail showroom, production facility, online presence, and wholesale operations. Before becoming an entrepreneur, illustrator, and writer, Tamara worked as a laboratory technician in a hospital microbiology lab. Although writing had been part of her life since childhood, she did not begin drawing until around the age of 40 and is largely self-taught, having chosen not to pursue formal art training. Her work is distinguished by a clever, specific, and often sarcastic sense of humor that transforms everyday experiences into relatable stories and memorable designs. In addition to her creative businesses, Tamara is committed to giving back to her community. She supports literacy through SMART Reading in Oregon, produces merchandise for local nonprofit organizations such as the Pride Parade and Wild Rivers Film Festival, and is an active member of Women in Business. Tamara attributes her success to persistence, creative authenticity, and the ability to evolve as both an artist and business owner. She has learned the importance of delegating in order to protect the time and energy needed for the creative work that only she can do. Her professional philosophy is simple: make work with a specific point of view, accept that it will not be for everyone, and learn enough about the business side of creativity to give good work a chance to survive. She believes the right audience cannot find work that its creator is afraid to make, share, or stand behind.
Her Interview
Ten minutes with Tamara
01What do you attribute your success to?
I attribute my success to persistence, creative authenticity, and the willingness to trust my own voice and vision. I have learned that success does not come from trying to create something that appeals to everyone, but from developing work with personality, purpose, and a genuine connection to the right audience. My journey has also taught me the importance of embracing growth and stepping beyond my comfort zone, particularly in learning the business side of entrepreneurship, including production, finances, rights, and operations. By combining creativity with practical knowledge, remaining open to reinvention, and continuing to create work that makes people feel seen and brings laughter into their lives, I have been able to turn a deeply personal creative outlet into a sustainable and meaningful business.
02What’s the best career advice you’ve ever received?
The best career advice I have ever received is to stop trying to do everything myself and focus on the things only I can do. As an entrepreneur, I initially took on nearly every responsibility, from creating artwork to managing the operational demands of a growing business. Learning to delegate and trusting others with areas such as bookkeeping and production allowed me to protect the time and energy needed for my creativity. I have learned that making space to draw, write, develop characters, and create new work is not an indulgence; it is essential to my well-being and to the continued growth of my business. By protecting my creativity, I am able to stay inspired, continue evolving, and bring the ideas that give my work its purpose to life.
03What advice would you give to young women entering your industry?
My advice to young women entering the creative and entrepreneurial industry is to stop waiting for permission to create and trust the value of their unique voice. Make the work, continue developing your craft, and do not compromise what makes you distinctive simply because it may not appeal to everyone. At the same time, learn the business behind your creativity, including finances, intellectual property, production, and operations, because understanding the business gives you greater confidence and the ability to protect your work. Most importantly, identify what only you can bring to your craft and make a deliberate effort to protect the time and space needed to create, grow, and bring your vision to life.
04What are the biggest challenges or opportunities in your field right now?
With the rapid changes in technology, small businesses have more opportunities and more pitfalls than ever. We have access to tools and platforms that used to be out of reach, but there’s also an enormous amount of noise. The challenge is figuring out which tools actually serve the work, and how to reach the people who will genuinely connect with what you make. That path keeps shifting.
05What values are most important to you in your work and personal life?
The values most important to me in both my work and personal life are originality, creativity, humor, and connection. I am especially drawn to the different ways people can take a familiar idea and make it their own through a distinct point of view.
I believe laughter can help people through difficult moments, and storytelling can make people feel recognized, understood, and less alone. Whether I am creating a character, making a product, or simply finding the funny in something true, I want the work to create a genuine moment of connection.
I also believe literacy is non-negotiable. Being able to read, understand, question, and communicate clearly affects every part of how we move through the world. Supporting literacy in my community is one way I can contribute to something I believe matters deeply.
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