Inverting the regrets of the dying

A few years ago, a palliative care nurse published a memoir in which she shared the top five regrets of the dying:

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
2. I wish I hadn’t worked so hard.
3. I wish I’d had the courage to express my feelings.
4. I wish I had stayed in touch with my friends.
5. I wish I had let myself be happier.

These regrets are endemic in society today - especially in an Asian country such as China - because the culture encourages or even celebrates the life choices that lead to regret.

For example, I work with undergraduate students every day, and I find it disturbing that many parents make the major decisions regarding their children's overseas studies and career direction. More generally, we are conditioned to care deeply about what others think. In China with the young generation, this is embodied by the epithet "别人家的小孩".

For most who don't rebel by lying flat, a 996 work schedule awaits the "lucky" ones with jobs in China's tech companies and securities firms. An entire country's culture (Japan's) is built on propriety and concealing one's true feelings. With excessively long work hours, there's no time to meet with friends. And as materialism strengthens its hold, fewer people discover the insight that long-lasting happiness actually springs from internal contentment and not from extrinsic factors.

Social pressures produce an enormous amount of inertia that makes it difficult to change (or even see) these problems in our lives. To devise an effective strategy for avoiding the aforementioned regrets, we can turn to another of Charlie Munger's mental models: inversion.

To invert means to do the opposite of something. Often, we don't know what's good for us; instead, we're more familiar with things that are bad for us. Therefore, we invert. To illustrate the concept, Mr. Munger once made the joke: "All I want to know is where I'm going to die, so I'll never go there."

What do the inversions of the top five regrets look like? I'll share my own perspective.

Follow or find your dream

Some people know what they truly want to do in life. Most people don't. But there's an easy way to tell - simply ask yourself, "Is what I'm doing now what I truly want to do in life, or at least is something that will move me closer?" When faced with this question, I think most people can produce an answer.

If your answer is no, the best advice I've heard to remedy this is from Deepak Malhotra, a Harvard professor who encouraged a graduating class of MBAs at Harvard Business School to "quit early, quit often".

Keep quitting until you find what you're looking for. Your heart will tell you when you've found it. The key inversion here is to ignore others' expectations because you'll hear all sorts of discouraging feedback. People will say you're crazy to quit, or crazy to try something so unconventional.

To borrow from Nike: "Calling a dream crazy is not an insult - it's a compliment."

Don't let your work define all of you

Some people are nothing without their jobs. I think that's a pretty bad place to be. Take 2-3 weeks of unpaid leave in between major projects at work. Take 2-3 months to do whatever you like (or do nothing at all) before on-boarding at your next job. Offer to take a pay cut so that you can work remotely.

One rule of thumb I have is to learn and earn in an equal ratio. In other words, I spend as much time learning as I do working. Whatever else is going on in my life, I've always been curious and always enjoyed learning new things. Everyone is different. Find the things you enjoy, and do more of them.

When in doubt, be honest

I think most people lie too often. They lie to potential employers, to potential marriage partners, to friends, and perhaps most critically - to themselves.

This is something that I've worked on a lot over the years, so I can share that most people have reacted positively to my directness. I've found that there are just two rules to follow when being honest: only say things about others that you feel comfortable saying to them directly; and always give feedback from a place of wanting the recipient to improve.

Make time for meeting friends

I wrote a post recently about this. Catch up with your closest friends at least once a month. For anyone whom you want to remain in contact with, do your best to meet them at least once per quarter.

Consciously pursue happiness

Happiness doesn't come automatically. There's no internal switch we can turn on manually that will instantly make us happy for the rest of our lives. Long-term happiness also isn't waiting to come to us in the future. And it most certainly won't come just because we buy a new car or a new house, or make a lot of money.

Long-term happiness is difficult to achieve because it requires our minds to think about life in a certain way. As a start, we can design our lives to maximize our chances of waking up with excitement for what we're about to do that day.

While (excessive) money is not correlated with happiness, some other indicators are. More freedom universally increases happiness. Financial security as well. A strong support network of family and good friends. A healthy body and mind. To be happy, be well.