This story begins in midlife…
About ten years ago, I had a conversation with Bill Cheswick about mentorship. I’d heard he enjoyed mentoring and wanted to learn more about the mentor’s perspective (we often focus on what a mentee gains, but not the mentor).
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Bill admitted he was nervous about Retirement. He worried he’d feel useless on the farm and disconnected from young people. Bill, one of the fathers of the network firewall, was retiring from Bell Labs after an extraordinary career of Innovation. His concern was simple but profound: would all he’d worked for go untapped by the next generation?
What struck me was how familiar his worry sounded. I’d heard the same from nearly 40 other mentors. They all shared a need to feel relevant, useful, and purposeful.
Almost two years later, I reached back out and asked Bill if he’d like to try mentoring in schools. His answer: “Yes! As long as I don’t have to do any administrative work. I just want to mentor.” That was enough for me. A small group came together. We got Bill and a couple of others into classrooms, my dad designed a logo and website, and Jura Zibas, a lawyer, volunteered to handle our legal work. We were fewer than ten people, without a roadmap—just a group having fun and bringing mentorship into schools. (You can read about this whole journey and all involved in The Mentorship Edge.)
Within two years, it was clear we needed to build something real. In 2019, The Mentor Project officially became a 501(c)(3). From there, everything accelerated. Sixty mentors in six months. Eighty in nine months. One hundred in a year—with a waiting list.
What started as a passion project that “could never grow” (because, as people told me, “the top Experts in the world don’t have time to mentor”) just kept growing. And those same experts proved the skeptics wrong, time and again.
Last year alone, we gave more than $3.5 million worth of mentorship hours to students in five countries. Today, The Mentor Project spans seven countries, with mentors who not only teach but also support each other – forming companies together, writing, creating, and even traveling to spend time with one another.
And now, in 2025, it’s time for me to pass the baton. I’m thrilled to hand leadership of The Mentor Project to Patrick Kelley and Jennifer Wade. Both are deeply involved already, both bring extraordinary business acumen, and both are ready to scale The Mentor Project to its next chapter.
People ask if it feels like I’m losing my baby. The truth is, it feels more like becoming an empty nester. When my boys went to college, my husband and I felt that emptiness, but also pride, optimism, and the excitement of new opportunities. That’s exactly how I feel now. The Mentor Project is “growing up,” and I couldn’t be prouder of where it’s headed. I’ll still “visit on the holidays”!
I’m excited (and a little nervous) to begin my next adventure: My Legacy Tree. More on that soon.
I’m grateful—for the pivots of choice that midlife allows, for the personal Growth it brings, and for the extraordinary friends and colleagues who’ve walked with me to this threshold and cheered me on as I step into the next one.
In some ways, it feels like my first days of college all over again—full of excitement, Anxiety, wonder, and hope about what the future holds.
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Originally Published on https://deborahheiserphd.substack.com/
