Retiring from a High-Tech Career and Exploring My Psychology
Stephen Pao Answering the E³ Q&A
I am proud to be a new Medium writer for “E³ — Entertain Enlighten Empower.” I’m following a suggestion from Malky to introduce myself by answering 11 questions from a Q&A list and to add one of my own. Here goes!
I write about my retirement journey, which has largely been spent picking up the pieces from a life spent too focused on an intense career as a high tech exec and outside my introverted (INTP) personality preferences. As someone who naturally dissociates from my emotions, I’ve been working on myself to improve my relationships with others. Heavy, right? On the lighter side, I also share tips about the mechanics of retirement, including friends, finances, healthcare, estate planning, civic engagement, and even singing karaoke! It’s a bit all over the place, which is why I’m exploring Medium as an outlet!
Where is your favourite place in the world? Portland, OR, USA. I often describe Portland with a “Goldilocks” metaphor — not too big, not too small, and just right. I’ve been lucky to go to school in Boston (MIT) and spend my high-tech career in both Silicon Valley and Seattle. I find the pace, the attitude, and places to go out “just right” for me. Plus, I rarely have to drive anymore. I still have a 2002 Audi TT ALMS with only about 100K miles on it, almost all of it driven while I lived in California!
My favorite film. This is easy — The Matrix. It is spiritual cinema masquerading as a sci-fi, martial arts, and action film. The film captures my feeling that our souls are playing out a simulated existence with artificial rules. The truth of this film becomes even more pronounced after stepping away from the working world, which imposes some very unnatural influences on how people think, talk, and act! I liken retired life to Zion, or “the real world” in the film.
My favorite music. I’m a child of the Eighties. I was and am a big fan of Depeche Mode. I recently saw them live at Moda Center when they came to Portland. Both Dave Gahan and Martin Gore are in their early sixties, but they are still rocking it! Like me with karaoke, they had to change the key of Martin’s arrangements a bit to sing hits like “A Question of Lust,” but I still enjoyed it!
My favorite TV series. I really appreciate Shrinking on Apple TV. I mentioned how I’m using my retirement journey to work on myself. Between my wife and I, we have three therapists: my personal therapist, her personal therapist, and a couples therapist to keep us off the path of “gray divorce.” The series is centered around the lives of three therapists and their own relationship challenges. The writing is so good. As someone personally experiencing a bit of therapy burnout from all the introspection in my retired years, I appreciate how the show finds both humor and touching moments in very real life situations.
Where do you invest your money? I have most of our money with two money managers now: JPMorgan and Northern Trust. When I was younger, I discovered I was pretty good at buying stocks and terrible at selling. By delegating the responsibility, I know I’m giving up fees, but I also free myself from the emotion and hoarding mentality. I still do invest a bit directly, but I’m trying to tamp that down!
How much money do you need? Like other Gen Xers who experienced both the dotcom crash and the Great Financial Crisis (GFC), I have terrible anxiety about “The Big One” hitting. Our current situation with the “Trump Slump” now in March 2025 isn’t helping! Probably the answer to the question of how much money I “need” at any time is “about twice as much as I have.”
What is your best piece of leadership advice? Since retiring, I’ve done quite a bit of consulting, coaching, and angel investing. I continue to return to some advice I learned early in my Silicon Valley career at a course run by Stanford Business School. The exercise starts with a question — “What is rule number one to having a successful business?” In response, I get so many answers related to execution in functional areas like product development, quality control, marketing, sales management, or finance. The classic answer, of course, zooms out a level — “To be in the right business.”
What enrages me about modern life is that facts no longer matter to the average person. Replacing fact-based reporting with social media is causing real harm in the world right now. It’s not just “entertainment” or “satire” but misinformation.
The last thing I googled. I just looked, and I’m embarrassed to admit that my last Google search was “define testatrix.” One thing I’ve done in retirement is update our estate plan, and I encouraged my mom to do the same. When reviewing her updated will, I noticed her attorney used the term “testatrix” which I’d never heard before. It means “a woman who has made a will or given a legacy.” Doh! I think I should have known that term by now!
I recommend you visit my Substack (retiredpdx.com) if you want to see some of my raw journaling. I’ll put more curated pieces on Medium, but I publish on my Substack twice per week about whatever comes to mind. One of our older daughter’s friends, who (like my daughter) is a Princeton sociologist, commented that they found it interesting just to see what someone in my stage of life chooses to write about!
And now for my own question. This is a new one for me in retirement..
What do you do for a living? This is how the conversation goes:
Others: “What do you do for a living?”
Me (enthusiastically): “I’m retired!”Others: “What do you do with all your time?”
Me (smiling): “Dick around!”
As a retiree, I no longer define myself by what I do for a living, but I’ve found that with new people it is often a lot to explain that I define myself by who I am, not what I do. I’ve found it easier to just say “Dick around!” because that response makes people laugh when they don’t want to learn more. And it makes those who do want to learn more interested in having further conversation!
These were some “quick hits” and I could write (and have written) a ton more on each topic. Do any interest you further?