How My Life's Meaning Evolved over Time

“For the meaning of life differs from man to man, from day to day, and from hour to hour. What matters, therefore, is not the meaning of life in general but rather the specific meaning of a person’s life at a given moment.”

— Viktor E. Frankl, Man’s Search for Meaning

In my post last Sunday, I spoke to my own personal meaning in retirement, starting at age 51, which is largely defined through the lens of the ABCs of Meaning (Agency, Belonging, Cause) with high levels of Agency and Belonging, but not through a Cause. In this post, I want to continue answering my friend’s question about how life’s meaning evolved for me over time.

Cutting to the chase, I think this is only a question I asked myself during three periods in my life — once from ages 34-38 during a midlife transition, once during a 9-week sabbatical while “back in the saddle” in Silicon Valley, and once now in middle adulthood as I’ve taken an early retirement!

Early adulthood

My early adulthood was rather typical, but perhaps a bit accelerated. By age 32, I was already an officer of a publicly-traded company, had a previous startup that I had already left go public, bought and sold a condo, owned a 4-bedroom house in Silicon Valley, gotten married, had a cat, and had one kid with a second on the way. I don’t think I pondered much about the meaning of life, as I believe my life’s meaning was more characterized by the pursuit of career achievement and establishing a stable life structure.

Midlife Transition

Carl Jung wrote about a midlife transition in men, typically starting at age 40, but often as early as 38. I believe I hit this midlife transition in full-swing by age 36. When I was 34, I already engaged in a life-reset by leaving Silicon Valley as a burned-out startup tech exec and returning home to the Seattle area to be closer to our kids’ grandparents. I ran three marathons in three months (Portland, Silicon Valley, and Seattle). At age 35, I bought a 2-seater (a 2002 Audi TT ALMS limited edition), typical of the stereotypical midlife crisis. (Pictured below is me years later with the car, which I still own in 2024!)

Also that year, I had gotten into cycling, and that year, among many other rides, I did a one-day STP (Seattle to Portland) “double-century” (a 200 mile bike ride). I also ran another marathon (Seattle) that year, too.

By age 36, I discovered I had an interesting case of diabetes. Like other Asians in America who later contracted this disease, I wasn’t overweight nor did I experience any symptoms. I revisited my diet completely, settling on Dr. Bernstein’s Diabetes Solution, which worked for a number of years. I also investigated various forms of alternative healthcare, including environmental medicine, chiropractic, and water fasting. I started meditation. (I recommend Mindfulness in Plain English for those who want to start). This was a period where I started to reassess my life goals and values. I looked for meaning and read Halftime: Moving from Success to Significance by Bob Buford. From a spiritual perspective, I also became a fan of Conversations with God, which many find heretical. (I do not.) This marked a period of questioning for me. From the standpoint of the ABCs of Meaning, I was exercising a lot of agency.

At age 37, I took a sabbatical from work, taking over 7 months off and not accomplishing much in a traditional sense. I volunteered for a non-profit. I got into a life coaching business with a friend. I started a photo kiosk business and placed my first machine, initially at a tourist shop in the Pike Place Market (Simply Seattle) and later at a high-end grocery store in Bellevue (Matthew’s at Lakemont). Probably the most traditionally productive thing to look back on was a month-long driving vacation over the summer with our young kids. 

At age 38, I spent about almost a year doing my first interim exec consulting gig for a local Seattle startup (All Star Directories). I really enjoyed working with the founder and the team. The problem space was really interesting in constructing a two-sided marketplace — having to attract prospective students on one side and to sell high-quality leads to for-profit schools seeking enrollments. At the center of this two-sided marketplace was a web infrastructure that would convert visitors into leads through content, merchandising, and web design. It was a whole new space for me personally, and I was an interim head of product focused on this website conversion. The value created ultimately resulted in a successful exit by the founder to private equity.

Separately, I had also gotten loosely involved with a company started by a former Tibetan monk (a longer story) and the former author of Norton Commander. At one point, I wondered if being a freelancer was going to be the way to go for me to afford me the most life freedom.

Ultimately, I believe I suspended my pondering on life’s meaning, as our kids were young and so was I. There is a Buddhist expression:

“Before Enlightenment, chop wood, carry water.

After Enlightenment, chop wood, carry water.”

For those unfamiliar with the expression, it basically means that no matter where you are in your enlightenment journey, you still have an obligation to care for your body, care for your family, and do your part in the community.

So ultimately, I decided to get back on the conveyor belt and return to Silicon Valley to join Barracuda Networks.

Back in the Saddle

From ages 39-49, I was back in the saddle at Barracuda Networks. We grew the company from its early days to becoming a publicly traded company. I put in a lot of hours and a lot of emotional energy. Candidly, I look back at this period as one of being on a bit of spiritual auto-pilot, only pulling my head up once during a 9-week sabbatical to revisit life’s meaning. Some highlights during that sabbatical period included taking time to start home brewing beer (jokingly called Tsing Pao in honor of another famous beer) and my first visit to a Buddhist meditation retreat (Spirit Rock). The net on revisiting life’s meaning in that time was an acknowledgement that the mission there at Barracuda wasn’t done yet, despite the issues the company faced at the time.

I cherish the time in my memory and value the relationships I made at Barracuda. I still keep in touch with many of those whom I worked with during that period, and many of my former colleagues are readers of this Substack!

Middle Adulthood

With the support of a very good friend, I returned to Seattle to help with his startup, and I began to revisit life’s meaning again. I was the first person on his advisory board, served as the company’s first CMO for a time, and then returned to the advisory board. By age 51, I got to the point of retirement to really pursue what Jung describes as Middle Adulthood, as a shift toward deeper meaning and more reflective pursuits. So this is where I am now, exercising a lot of agency, and it is why I am writing this Substack!

An otherwise typical path?

While I have been blessed with several periods of reflection in my life (during a midlife transition from ages 34 to 38, my 9-week sabbatical while “back in the saddle”, and an early retirement at age 51) I believe my life so far has followed a pretty typical path in another sense. I was entertained to hear Jack Ma, founder of Alibaba, speak about this very topic in his own reflections.

He provides his own basic framework and my life so far has mapped pretty well to it:

• Before 20 years old, be a good student.
  I did this all the way up until age 23, when I received both my bachelor’s and master’s degrees in electrical engineering from MIT.
  

• Before 30 years old, follow somebody. Go to a small company. In a big company, it is good to learn processing. You are a part of a big machine. In a small company, you learn the passion. You learn the dreams. You learn to do a lot of things at one time. It’s not about which company you go to but rather which boss you follow. A good boss teaches you differently.
  I did this all the way up until age 34. While I did my engineering internships at a big company (Weyerhaeuser) and had a great boss, I ultimately kept joining smaller companies, starting right after school at Oracle where I also had a great boss. I followed that stint at Oracle with the greatest learning in a single year of my career at my first startup, Visioneer. Then, I had two really great bosses at my second startup, Latitude, where I joined as employee #30 as a product manager and left as the VP of Marketing of a publicly-traded company.
  

• From 30-40 years old, you are working for yourself, if you really want to be an entrepreneur.
  This is where I differed from the path. As mentioned above, I spent ages 34-38 in a midlife transition through a couple of stints as a startup tech exec in Seattle, some time off, and then my first stint as a consultant on an interim exec assignment. I then hit “pause” on my midlife transition to take the next phase.
  

• When you’re 40-50 years old, focus on the things that you are good at. Don’t try to drop into new areas. It’s too late. You may be successful, but the rate of dying is too big.
  I spent ages 39-49, focusing on what I was good at, having returned to Silicon Valley with Barracuda and growing the company as it went public.
   

• When you are 50-60 years old, work for the young people. Because young people can do better than you. Rely on them, invest in them, and make sure they’re good,
  This is where I’m at now, and I’m working for friends who are younger. (I’m currently 57!)
  

• When you are over 60 years old, spend time for yourself. On the beach. Sunshine. It’s too late for you to change, normally.
  The future is a mystery!

So, to answer my friend’s question from the previous post, I’d say that my life's meaning did evolve through periods of my life. Through most of life, I was basically following Jack Ma’s (or more broadly, tech society’s) gameplan. During three critical periods, I was granted the gift of being able to exercising agency:

• During my midlife transition, I had the ability to explore a lot of directions, not all of which were seemingly productive at the time, even though I now have a newfound appreciation for the learning. 

• During my sabbatical while “back in the saddle”, I exercised agency and knew I was choosing to go back into the grind. 

• And now, during my early retirement, I am exercising agency to explore my own emotions and relationships. And being able to go out for beers on weekday afternoons doesn’t suck either!

I’m interested to see what’s next!