How I Found My Happiness

I thought happiness was about achieving more

I grew up in Taipei and came to the States for college at Brown. As a computer science major with a love of building products, I filled up my weekends with hackathons across the Northeast. At my fifth hackathon, I bonded with a senior whom I really looked up to and we co-founded a startup.

To be fair, my startup knowledge was quite limited at the time. I had never heard of Y Combinator. I had never read Paul Graham. While I don’t advocate following gurus blindly, I do see value in reading startup literature in retrospect.

The lack of knowledge didn’t stop me. I went all-in and prototyped a few ideas along the way. We entered a few contests, won some and lost the others, and eventually honed in on a salient product insight that had a sizable market. Though we worked very hard, we eventually gave up on realizing the big wild dream.

Though the startup didn’t succeed, it taught me so many lessons from navigating product-market fit to managing relationships with all kinds of people. It also opened so many doors, such as a program manager internship offer from Microsoft in my first year and many other big-name companies in the following years.


Am I happy?

I didn’t notice that I was optimizing for the wrong metrics. While I knew better to not aim for financial success, I was still playing the status game. I chose to interview at the most competitive companies in the world because I wanted to prove myself. I thought happiness is about achieving more. I thought I could acquire happiness.

However, I wasn’t happy after achieving all my goals. My coach recommended me to look inwards, so I started to review my journals, meditate, and study neuroscience. The more I learned about meditation and neuroscience, the more I began to tap into my soul. Eventually, I noticed that I was trapped by the initial “startup failure.”

Instead of suffocating the inner voice, I chose to accept the failure entirely. As I leaned into the moment, I was able to see my past from an objective point of view. I realized that I was stronger than my resistance. With this new awareness, I could finally move forward.


My renewed definition of happiness

Through my study of psychology, neuroscience, and spirituality, I learned to debunk some myths around happiness:

Happiness is the journey, not the destination

As I discovered earlier, achieving a certain outcome wouldn’t bring you happiness. Even worse, if your happiness is attached to the outcome, you may get to a worse state if you fail to achieve. Thus, it is better if you could find happiness before you attain the goal.

Happiness is found in the presence, not some distant future

This is aptly described by the I’ll be happy when syndrome. How many times have you told yourself, “I’ll be happy when I graduate / find a job / get married / have a kid?” If you constantly live in the state of acquiring happiness, you will never be happy because your happiness is constantly delayed. Life is a lot more fun when you choose to believe that happiness is found right here, right now.

Happiness is defined by personal measures, not external status

If you were like me, you may have internalized a lot of standards and sought after shiny status. For example, many people let the need to achieve financial freedom stand in the way of their happiness. This is dangerous because they are relying on external measures to feed their soul. I believe that the most sustainable way is to tap into your inner strength and define happiness on your own terms.

Happiness is the natural by-product of a well-lived life

To live well, we need to follow through on our promises and consistently show up for ourselves. Happiness will naturally come after we win our own respect.


While we all know the principles, the game-changer lies in the details and execution. If how-to guides were enough, why aren’t we living happily already?

  • We all know that exercise can lead to a better shape, but few people commit to their daily workout schedule.
  • We all know that reading can level up our playing field, but few people dedicate more than 1hr to reading.
  • We all know that new challenges are critical to progress, but few people carry out their new year resolutions.

For one, it is hard to escape the rat race when society is priming us to achieve more. For another, it is lonely to pursue the big hairy dream that feels right but runs on a super long time horizon. To ensure lifelong transformation, strategy and accountability are key.

So How Will You Measure Your Life?

In How Will You Measure Your Life, Clayton M. Christensen shared the three questions he used to ask Harvard Business School’s graduating class:

How can I be sure that…

1/ I will be successful and happy in my career?

2/ My relationships with my spouse, my children, and my extended family and close friends become an enduring source of happiness?

3/ I live a life of integrity — and stay out of jail?

In order to make good decisions, we need to do more than collecting past data because those data are only about the past. We need to construct theories that could explain what causes what to happen and why. Only with such theories can we better predict the future.

Finding Happiness in Career

Many people pick jobs for the wrong reasons and settle for them. Gradually, they accept that it’s not realistic to do something they truly love for a living. However, it doesn’t have to be this way. As I often tell my friends, you have the agency to design your career.

Professor Christensen pointed out that there are many events that cannot be explained by pure financial incentives. Compensation is in fact a hygiene factor. It has to be fair, but it won’t make you love the job. To escape the reality trap and find happiness at work, you need to seek meaningful opportunities that could satisfy the following motivation factors:

Hygiene Factor VS Motivation Factor

1/ Combining Deliberate and Emergent Strategy

Think of deliberate strategy as the current job you are doing and emergent strategy as the wildest dream you always want to pursue. For me, being a product manager is the deliberate path. At the same time, I am openminded towards all kinds of opportunities ahead.

During college, I would write down a list of experiences I think I would enjoy and test them with different kinds of projects and internships. Through this rapid experimentation, I quickly iterated, adjusted my expectations, and found the work I love.

2/ Testing Major Assumptions

Now you may be wondering whether your current or next job satisfies your needs. Here is the question Professor Christensen recommended us to ask:

What are the assumptions that have to prove true for you to be happy in the choice you are contemplating?

By writing down my assumptions for major projects, decisions, and life transitions, I was able to better wind up projects that fail to deliver promises. If you want to check whether you are implementing your desired strategy, take a look at your calendar and see how you spend your time.


Finding Happiness in Career

1/ Do The Jobs Well

In our daily lives, we have many “jobs” that we need to do. A good product or service is what does the job well. This job-to-be-done mindset is what differentiates IKEA from standard furniture stores.

IKEA does the job of furnishing a new apartment well. If you are moving to a new city tomorrow, you know that IKEA can provide the basic furniture that serves your needs. Specifically, IKEA has a big store to ensure that furniture is in stock, a large space to keep your kids busy, and a restaurant to keep you in the same building. IKEA provides a full experience that helps you get your job done.

In the product landscape, Alan Klement describes the process as finding a “better me.” A good product would help people feel better by using the product. A good example is Tiktok. Tiktok didn’t simply go viral because of the younger generation. The underlying principle is actually because it taps into the human desires of self-expression and creativity in its own unique way.

This principle also applies to your professional and personal relationships. By applying the job-to-be-done mindset to relationships, you will develop empathy to see what job your partner needs you to do the most. By doing that critical job well, you will not only make your partner happy but also strengthen your commitment to a more fulfilling relationship.

In Professor Christensen’s words:

The path to happiness is about finding someone who you want to make happy, someone whose happiness is worth devoting yourself to.

2/ Navigating The School of Life

Nolan Archibald, the youngest-ever CEO of a Fortune 500 company, shared the key question that drove his trajectory towards becoming CEO of a successful company:

“What are all the experiences and problems that I have to learn about and master so that what comes out at the other end is somebody who is ready and capable of becoming a successful CEO?”

While this is often not the most prestigious or high-paid job, this question helped him take on challenges that would lead to high growth.


If you are interested in another life analysis, I recommend David Brooks’s The Second Mountain. ✨

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