Ending my tech career on a high note



Yep, you heard right. I am leaving my tech career to pursue a totally different domain, with a goal to bring more joy, meaning, and impact to people’s lives. Before I get into that, I want to express my gratitude…

I am ending my tech career as the CIO of Rapid7, which I never would have imagined 23 years ago when I moved to Silicon Valley to get a job as a C++ developer at Serena Software, innovating in software change management and devops (thank you, Doug). I have had the pleasure of working with really smart people on really hard problems like closing the security achievement gap, all while having fun at the same timeRapid7 has been an amazing platform to learn, grow, and have a positive impact on customers and society. I am filled with intense gratitude for our customersand all the people that invested in my development.

This was a difficult decision, not made lightly and let meshare how I came to it… I had a great job, working with smart people on hard problems, but something wasn’t sitting right… ​

I had this low-grade anxiety caused by a conflict between my inner self and outer self that was bringing itself to awareness more and more.

I had to dig in it to discover what was going on. In Walking with Purpose, I described a High Sierra backpacking trip where I lacked motivation and discovered that I had lost the passion for long solo trips. I hit high snowpack at Precipice Lake, sat down, ate a candy bar, looked at my light alpine gear, and decided to turn around. The risk and grind of pushing through six feet of snow over multiple passes was not worth the reward. As soon as I started heading back, I was filled with purpose and passion to return safely to my family. I experienced hours of flow and joy in the two days it took to get back to the truck and realized the importance of purpose. This trip gave me hours on the trail to inspect motivation and purpose.

When I inspected my anxiety, it was coming from the fear that I was not using my remaining years to work on something more aligned to my purpose and passion. So what is that purpose and passion? Well, I have had the pleasure of working on really hard problems from open source cultural resources management for the National Park Service, to devops at Serena, to cyber security at Rapid7, with purpose-driven colleagues, for almost thirty years now. The favorite part of those experiences, most recently, was helping others achieve their potential. The technology, organizational, and operational stuff was not as motivational for me as it used to be. I was moving from operator to coach more and more every day, and that transition was bringing me joy. I was transitioning to using my crystallized intelligence and relying less on fluid intelligence and wrote a blog about it here.

Meanwhile, Kerri and I had been experimenting with this concept of “Being Well” with a variety of personal and community investments. Kerri created Be Well Gardens which is about connecting families to wellness through food, influencing thousands of kids and hundreds of families over a decade. In 2018, we launched Be Well Retreat, Kings Canyon, which is an experiment in connecting families to nature for wellness which has influenced over one hundred families in three years. In 2018, I started this blog to capture my research on non-invasive neuro-hacking through meditation and neurofeedback. Putting this all together, we believe we can help individuals and families achieve more joy, meaning and impact in their lives through nutrition, nature, and non-invasive neuro-hacking.

Well, I am transitioning my CIO role to someone new (at the time of writing this, not hired yet, here’s the job description, send references our way!) and will remain at Rapid7 to the end of the year. After that, I look forward to having time to drop the kids off, pick them up, and giving Kerri more time to invest in her career. We are thinking about launching a second Be Well Retreat for families to experience off grid and tiny house living at our Onyx location and maybe someday I will get around to building that climber’s retreat at our Joshua Tree location. I look forward to building some new structures, Kerri will dial in the irrigation, and the kids will build forts and play with the dog. I am most excited to have more time to engage in aimless play with my family.

To feel competent in neuroscience, I enrolled in a master’s program at Kings College London and will graduate in early 2024. Part of my research will be on the effect of contemplative practices on anxiety and depressive disorders (I will share my hypotheses in later blog posts). I also enrolled in the peak performance instructor training at Flow Research Collective to better understand the neuroscience and practices for peak performance and to be certified to teach others. Specifically, I am interested in learning the triggers of group and individual flow to make peak experiences repeatable and common. Both of these will lead to research, open source templates/frameworks, and coaching services that I call “Be Well Mind”. Stay tuned for more details on the launch! I also plan on continuing the rewarding advisory work I do in education and tech startups.

As the sun sets on my technology career, I am happy, challenged, and motivated like never before. My friends, family, and colleagues have been incredible through this transition and I appreciate and love you all! I can’t imagine ending on a higher note.

Be well,


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