The Problem With “Just” Scratching Your Own Itch

Tell anyone in Silicon Valley that you’re stuck for startup ideas and they’ll probably shrug and say: “Just scratch your own itch.” In other words, if your foot is tingling, you don’t need to wait for Apple or Google to sharpen their nails. You can innovate by solving that problem yourself. If you do it well, chances are other people will find it helpful too.

The challenge is that there are endless itches in the world. How do you know when you’ve found the perfect one to innovate on?

I went to Heather Hiles for answers.

Hiles grew up as the only person of color in their high school’s AP classes. “It was very fragmented,” they told me. “The people who looked like me were the bus drivers.” Banning racial segregation in schools could not prevent the informal segregation Hiles and other children of color experienced.

After high school, Hiles was accepted into UC Berkeley and received a scholarship to play basketball. They were raised by a single mom who was thrilled when she heard the news.

But Hiles turned the offer down. “I wanted to be protesting and doing all the cool things people from all over the world do at UC Berkeley,” they said. “I didn’t want to be at the gym.”

To fund their education, Hiles worked throughout college, running an after-school program for local school children. There, Hiles quickly realized that the inequities they witnessed growing up were not an exception — they were the norm.

Hiles’ foot was tingling.

But their first company was not a panacea for educational inequity. It was a secure document-sharing site that they worked on with a colleague. It was an itch — Hiles frequently struggled to share photos with their family — but it wasn’t the perfect one. Hiles and their co-founder struggled to get funding and attention.

As they scrambled to keep the company afloat, Hiles stumbled upon a different idea: online portfolios. But their cofounder vehemently shook his head at the idea of pivoting.

The perfect itch is the worst one: the mosquito bite that inevitably ends up bleeding, instead of the vaguely annoying sensation on your back. While vaguely annoying sensations require mere tweaks to solve (i.e. buying a back scratcher), mosquito bites require bold solutions (i.e. the termination of mosquitos). Secure photo sharing was Hiles’ vaguely annoying sensation. Educational inequity was their mosquito bite. “I had seen that injustice for so many years,” Hiles said. “Nothing could be more motivating than that.”

So, Hiles started Pathbrite on their own. Pathbrite was an e-Portfolio platform that helped students document their learnings. Teachers could map out skills for the students to work on that would help them reach their goals. It ensured that future teachers wouldn’t have to start from scratch to learn how to best support each student. Seven years later, Pathbrite was acquired by Cengage, one of the largest education technology companies in the world.

So, what’s the secret?

Hiles’ success stemmed from finding the perfect itch. Educational inequity was fundamental to the way they grew up and contributed to their feeling of being an outsider. It was a problem they could dedicate their life to. Even post-acquisition, Hiles has stayed committed to bridging inequity. Hiles serves on the Board of Directors of Udemy, is an ex deputy director for postsecondary success at the Gates Foundation, and was the founding CEO of the world’s first fully online community college.

Many startups today fail because the problems they tackle are too small. They are improvements to existing products, instead of innovations driven by a larger mission. Deciding to create a company for waterproof phones may solve your itch of being clumsy near the pool, but it needs to be driven by a larger mission to sustain itself. For example, Steve Jobs started Apple with the itch of needing tools for his mind that could simultaneously advance humankind.

Whether it’s goodness-driven like Hiles or progress-driven like Jobs, innovation starts with finding the perfect itch. It needs to extend beyond minimal discomfort to unbearable pain.

What’s your mosquito-bite-sized problem? What’s stopping you from solving it?

This article is part of my series about achieving the impossible. Read the last article here and subscribe to future updates by clicking the orange mail button on this page near my name.

Want to stay in touch? Come say hi through my newsletter, Twitter, Instagram, or LinkedIn. You can connect with Heather Hiles on Twitter and LinkedIn.




Author of “Think Outside the Odds” & student at UC Berkeley. Thinking about empowering the underdog and how we can all live more intentional, innovative lives.

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Vedika Dayal

Vedika Dayal

Author of “Think Outside the Odds” & student at UC Berkeley. Thinking about empowering the underdog and how we can all live more intentional, innovative lives.

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