Two years ago, my father passed away at the age of eighty-eight. I turned fifty in that year. I was struck with the realization that life is too short and our time on this earth is very precious. One of my father’s last words was “life is like a dream”. If life is but a dream, how do I make it a good and happy one with fewer regrets, which I can cherish in my last moments? 

In the last one year, I was growing increasingly disgruntled with the company I was working for, which was one of the Mag7. The company culture was deteriorating and I became no longer interested in the work. I had learned and grown my professional skills a lot and benefited financially over the years working there, but I reached a point that I didn’t want to continue to tolerate the negative aspects and trade off my precious time for the paycheck. 

I thought about four options – 1) Switch team again within the company; 2) Switch company; 3) Leave the company to FIRE; 4) Leave the company and try to build something on my own. 

I thought through the pros and cons for each of the options. For option 1, I looked through all the openings within the company for several months, I did not find a team or product area I was really passionate about joining, and I knew that many of the company culture problems would stay the same even if I switched to another team. I had to be honest to my feelings, so I didn’t pursue that. 

For option 2, again I didn’t find a company that I genuinely was excited about joining given the company’s mission and culture. Another consideration is that the new generation of AI native companies typically demand very long work hours and high intensity. Given my age, I don’t think it’s wise for me to be embroiled with the 9-9-7 work culture, and trade off my health. In my 20’s or 30’s, I went through that work pace, but now with family responsibilities, young child and elderly parents to take care of, I don’t think it’s worthwhile for me to sacrifice my family and health. 

For option 3, I think it is still too early for me to retire and sit on the beach every day, without engaging in productive work and being intellectually challenged. I will be bored and it will not be healthy for me mentally, and I want to set a better example for my son in elementary school. 

I chose option 4. For my entire professional life, I have always worked for companies, followed other people’s rules, and contributed to other people’s businesses. In other words, I have always been playing other people’s games. It’s time for me to find my own game and play the game I truly enjoy, for the second half of my life. If I am lucky, I have another thirty years of productive life which I can dedicate to that game. I think finding the game one loves and keeps playing it throughout life is the closest thing to the meaning of life. Also recognizing the life stage I am in, I want to strike the right balance among productive work, health and family. Ultimately I am optimizing for happiness and contentment, and health, family and work are all essential pillars for happiness and contentment. 

I realize that my choice was motivated by 1) my desire to regain more control over how I use my time and energy; and 2) my goal to optimize for more balance and happiness in life. 

This is not an easy choice, as I will have some short term financial sacrifice; I need to adapt to a new condition of life; I have to define and structure the new work for myself; and I need to stay motivated and disciplined without any external pressure. 

I think the best course is to stay true to myself, follow my own interests and passion, and always have the courage to change and try new things at any age in life. 

A Decision Steward’s Reflection

At first glance, this is a decision to leave a successful Big Tech career. But the deeper decision is not simply whether to stay, retire, or build something new. It is whether to continue following a well-established path—or create the time and freedom to discover what might make the next 30 years meaningful.

The contributor has not yet found that “something.” That makes the decision more uncertain, but not necessarily less sound. Sometimes we expect people to identify their next destination before permitting themselves to leave the current one. Yet remaining in an all-consuming role may leave little room for genuine exploration.

Annie Duke warns against “resulting”: judging the quality of a decision solely by how it eventually turns out. As she writes in Thinking in Bets:

“What makes a decision great is not that it has a great outcome. A great decision is the result of a good process.” — Annie Duke

Whether the contributor eventually builds something important, finds fulfillment through community, concentrates on family and personal stewardship, or changes direction again should not determine whether this was a good decision. A good outcome can follow a poor decision, and a thoughtful decision can still produce disappointment.

The more useful questions concern the process: Did the contributor honestly examine the available alternatives? Did he recognize what he was no longer willing to sacrifice? Did he understand the financial and personal consequences? Did the decision reflect his values and the realities of his current life stage?

His reflection suggests that it did.

But leaving is only the first decision. The next challenge is to turn an open horizon into thoughtful exploration. What possibilities will he test? What experiences will help him distinguish a passing interest from a purpose worthy of the next chapter? And how will he explore without prematurely forcing himself to name one new “game”?

Perhaps the courage in this story lies not in already knowing what comes next. It lies in acknowledging that the old answer no longer fits—and accepting a period of uncertainty in order to search for a more authentic one.

The question this leaves for our community is:

Must we know exactly what comes next before leaving a path we already know is no longer right for us?