The first reboot
15 years ago, I left corporate work to care for my mother, who has cancer. That responsibility continues today. I’m also raising young children, so this next chapter is taking shape in the middle of family life.
I built a new working life around writing and teaching. My background in real estate and finance, and my Stanford MBA, gave me useful material to draw on. Over time, that became three books and courses with more than half a million enrollments across Udemy and LinkedIn Learning.
Those were ways to make something useful from what I knew, within the life I needed to lead.
Why another chapter now?
Since ChatGPT and other AI tools arrived, I’ve seen a significant decline in the books and courses that supported that chapter. People have new ways to learn. I’m feeling that change firsthand, even as I explore what the same tools make possible.
Something can work for years and then change. Experience still matters, but the way we put it to use may need to change with it.
I want to find out what a meaningful next chapter can look like for someone in midlife, with experience to draw on and responsibilities that do not disappear. I’m giving myself a six-year horizon to explore that question, one practical experiment at a time.
What you’ll find here
A question worth thinking about. Something I build or try because of it. A resource you can borrow.
Some projects will be useful. Some will be fun. Some will be a lesson in where my time and money did not need to go. I’ll share the costs, corrections, and uncertainty that help you decide whether an experiment fits your own life.
You can come for a single resource or follow the longer story. You do not need to be in real estate, know how to code, or have a neatly packaged plan.
An earlier version of this site already mixed practical philosophy with useful tools. In 2019, I wrote about our experience of time and made a spreadsheet to explore the idea. That archived essay is a reminder that these questions have been with me for a while.