The Coolest People I Know: Stephen Pao, aka "The Retired Techie"
Meet Steve, who retired early from a demanding career in the world of Silicon Valley tech to explore his personal world. Find out why this MIT grad feels like he never really finished 3rd grade!
I recently had a great conversation about creating a prime-time life in retirement with Stephen Pao, who is also a writer on Substack and publishes his newsletter, The Retired Techie. Steve worked for 30 years in the tech industry in Silicon Valley and then later in Seattle. He held executive positions for companies in the last 20 of his career before retiring in his early 50s. In his fast-paced career he was part of seven start-up companies and went through the launch of two IPOs. He now lives life at a slower but rewarding pace in Portland, Oregon.
Sally: Hey Steve, I discovered your publication called “The Retired Techie” not long after your launch. I was drawn in to read what you share with readers about your post-retirement life. I’m new to this same phase in my life so I’m very interested to learn from and relate to others who’ve left their careers behind in pursuit of a “new chapter.”
You retired from a successful career in tech with a lot of high-demand roles. Was there a particular event that led you to retire from full-time work in your early 50s? Or was it a series of events?
Steve: Sally, thanks for reading what I share! I started to write on Substack as more of a personal journal that I put out there to keep me motivated to keep writing!
In truth, there was a confluence of events, largely related to my continued discovery of my life’s meaning.I did have what we call “workplace burnout,” but I was fortunate to have had two breaks during my career to explore life more.
My first was in 2004 after I left a job to evaluate what was going on with my health. My second was in 2011 while I took a nine-week sabbatical as my company was in flux, and that turned out in the end to be a CEO transition.
After going through my second IPO with a company and serving as a division GM for a publicly traded company, I moved up to Seattle to help a friend with a startup. By the end of 2017, we had both raised a Series B round at the same time my younger daughter had gotten in early decision to college. And, my wife realized that her 20-year career as a stay-at-home Mom was being outsourced to East coast colleges! Thinking about all of this change, I realized I was ready for a new chapter as well.
So, we held hands and jumped off the full ship of full-time work together.
Our younger daughter went off to college on August 17, 2018. On August 18th, our moving truck showed up to move to Portland, where we officially started retirement!
Sally: I smiled in our conversation because you use the term “retired” so easily- I struggle with what to call this phase of my life where I’m working but I don’t have a job. The best word I’ve found to describe it is “striving”- I still strive to create work and put it out into the world.
Talking with you, it seems as though you’re still striving to accomplish new things- like writing on Substack, for example. Do you have a legit “bucket list” of things you want to do or places you want to go? Or do you follow opportunities more spontaneously?
Steve: I didn’t have a bucket list when I retired. I just started by trying new things. I started volunteering for a local tech association to help businesses here in Oregon. I started doing angel investing. I started a consulting practice, largely to help friends with their venture-backed startups.
Of course, during retirement, we experienced COVID, too. So that was six months of our family, all together. And that was a gift to have to reset our relationships with our kids as adults as we were all crammed into our 2-bedroom / 2.5 bath retirement condo!
We did go places. First on the list was a fasting clinic in Germany to try a 28-day fast as an attempt to “reset” my health a bit. But most of our traveling has been to see people. We went to visit our kids at their college parents’ weekends at Yale and Carnegie Mellon. We went to visit our older daughter in Bangkok when she was working at the UN and in the UK while she was getting her master’s at Oxford. We went back to London to visit our younger daughter while she was getting her master’s at University College London. We also did a driving vacation for a month last summer to see old friends.
This year, so far, we went to Japan this year as a family to see both friends and my wife’s relatives. We did a spring break trip to Spain with our younger daughter while she was still studying in Europe. We just got back right before Halloween from a trip to Princeton to see our older daughter, as she’s doing her PhD there right now.
I am 57, and I think this is a perfect time to transition…to fully focusing on ourselves.
Sally: You shared with me the theory by Jack Ma, former founder of Alibaba, about the trajectory of a career over the decades. Can you share this theory here that might provide insight to others in their 50s and beyond who are fearful about a life post-career?
Steve: Jack’s theory on the stages of work basically said that in your 20’s, you should go in search of a job with a good boss. Your 30’s are a good time to explore all of the options for your career. In your 40’s, you should focus on what you’re good at, and in your 50’s, go work for people younger than you.
And in your 60s forward, focus on yourself!
I am 57, and I think this is a perfect time in our lives to transition from working for the young people (as I’m doing with my current consulting business in a sort of semi-retirement) to fully focusing on ourselves. For both me and my wife, Marsha, it’s a period of life that nature never intended us to have because we are “empty nesters” and not yet grandparents! Before birth control, this was an impossible period to have, but we’re blazing this trail now!
Sally: Your Substack newsletter is called “The Retired Techie,” but you’re not strictly writing about the tech world. This is more of a journal of your personal experiences and insights that you’re choosing to share with the world. You’re writing about yourself and “the rest” of your life beyond work. What made you decide to publish a journal like this for others to share this side of you?
Steve: I have been exploring this myself. I once had a friend who skipped the third grade, when we used to learn how to write cursive. He told me that even as an adult, he never really learned how to do something basic like write a “z.”
I think for me, I spent my life as a nerd. I went to MIT. I worked in Silicon Valley. I was an introvert. My kids say I have undiagnosed ASD. I didn’t literally skip the third grade, but somehow I think I skipped some things that normal people do, and I missed some important life lessons that I’m learning now in my 50’s. I thought I’d write some of them down and share in my Substack journal because there might be others like me who didn’t learn these things either.
Sally: I was dreaming for a few years of leaving full-time work before the standard U.S. retirement age. And then I was able to make it happen. I’ve thought about whether I “manifested” my dream by focusing my thoughts on it and then seeing opportunities appear that made it happen. What’s your interpretation of “manifesting” in terms of making what you dream of actually happen?
Steve: I just think that sometimes the right people show up in your life when you need them. Somehow, the forces of the universe draw people and opportunities to you. I think you’re right- that you have to see when this is happening and pursue them. This has happened to me multiple times.
My first startup that ultimately did an IPO while I was there came by way of a former coworker who found out randomly that I’d gotten laid off before I did! We had a mutual friend whose girlfriend was a headhunter. She had the inside track on who was being laid off at my company and heard about me. At the same time my friend’s company was about to make an offer to someone with a similar skill set to mine. I ended up getting in at the last minute and beating out the other person for the new job. Crazy coincidence.
My first consulting gig came because a guy who I’d met once called me out of the blue because he was too busy to help a client. It turns out that the client was a friend of a friend and had an employee that used to work for me. Total coincidence.
My first experience of alternate life journeys came to me when I was in a doctor’s office and met a guy who’d read “Halftime: Moving from Success to Significance” by Bob Buford, which was helping me understand what was happening with my midlife transition. Total coincidence. There have been many other books that people have told me about first, including “From Strength to Strength: Finding Success, Happiness and Deep Purpose in the Second Half of Life” by Arthur C. Brooks, but “Halftime” was the first one I’d read along those lines!
The list just keeps going even now with retirement opportunities. Heck, even doing this conversation online was the result of you showing up in my life!
I also think there are a lot of ways that I needed to refine how I prioritized friends and family in my life. I think I realized before that I was probably pretty lonely back then.
Sally: What are some aspects of your post-career life that you really enjoy but didn’t really know you would- or even know that they’d be in your life- before you stepped away from a full-time career? Tell us about the pleasant surprises and the disappointing discoveries.
Steve: This isn’t related strictly to retirement but to life. I think the most important discovery is that no matter how hard we worked at being parents and no matter how hard we tried to do the right thing, there are still traumas that we imposed on our kids. I think the thing I didn’t think about but have realized is the need to reset and nurture adult relationships with our kids in different ways.
I also think there are a lot of ways that I needed to refine how I prioritized friends and family in my life. I think I realized that I was probably pretty lonely back when I was working. I am super lucky that my wife and I have been friends since we were kids and that we as romantic partners just kept getting closer over the years. But we moved around a bunch, I worked a lot, and I am a natural introvert. I believe I was part of what’s now being called a “friendship recession.”
I just realized in retirement that I had to be a lot more intentional about friendships, and I am really enjoying it.
Sally: Are there any new ideas of “what I might do next” coming into your thoughts now?
Steve: I think this is less of a focus in general, as I realized in 2023 that I was “doing” too much. After realizing this, I basically spent the bulk of last year unwinding a lot of the stuff that I was involved in, much around the consulting side. And I wiped the slate clean for 2024.
It was a good time to do that. We had a number of deaths among close family and friends this year, starting with the passing of my mother-in-law on January 15th. It’s not been a good year for that, as I’ve had a friend lose both of his parents, one friend that lost a 19-year old son, and we lost my closest first cousin on my mom’s side of the family.
So, after the dust settled on much of that, I just decided to start a Substack. I’m like 20 articles in right now, so I am just getting started! I am not sure if it’s going to ever be more than a personal journal that other people read, but I am putting some time into it and having people give feedback and comment on what I’m sharing is a great benefit that might keep me writing.
For now, I think I am in a mode of “being” rather than “doing.”
Sally: I really liked this newsletter you published several weeks ago. I hope those enjoying reading about you and your journey will read more from you.
@Sally Doran - thanks for the shout-out and for letttng me be a guest on your new Substack series!