Advice I would give to my 20-year-old self

Muir Woods trails

The following is an article I wrote in 2017. I'm reposting it here because others have told me that they found it inspiring, and so I wanted to share it with new readers.


As a professional in education, I’m often asked to give advice or mentorship to students who are about to apply for graduate school, or to young professionals at the start of their careers.

I guess the logic is that I should know what I’m doing, since I’ve already lived through my 20’s and come out relatively unscathed. But to tell the truth, I’ve made my share of mistakes in my 20’s. And so, this article will be one of reflection. I’ll share some things I’ve learned over the years, presented in the form of advice I’d give to my 20-year-old self. Perhaps readers who happen to be in their early 20’s could derive from some value from this.

Quit early; quit often

This radical sounding piece of advice, borrowed from a speech given by Professor Deepak Malhotra to the graduating MBA class of 2012 at Harvard Business School, really encapsulates the essence of how you should approach your early adult years.

One of the secrets of life is that no one really knows what they’re doing. Your friends, your parents, Harvard MBAs – everyone is living life for the first time. We’re all winging it.

What does this mean? It means that it’s okay to make mistakes. That’s how we learn. It’s okay to make a wrong decision, but it’s not okay to realize this and not take any action. When you discover that something is not right for you, quit earlier rather than later.

When I first entered university, I chose to major in electrical engineering for two major reasons; it’s one of the most difficult majors to get into, and it practically guaranteed you a job upon graduation. I hated it. And yet, I stuck with it for over two years before eventually transferring to a different university and starting over. I then majored in something completely different – English literature. It was fine, and I graduated without changing my major again, but I felt it still wasn’t completely right. Only years after graduation, after some relevant experiences and an MBA, did I realize that I should have majored in economics as an undergraduate.

Ironically, my roommate during my second year was an economics major – but while it may have been right for me, it probably wasn’t right for him. He ended up going to law school and becoming a corporate lawyer in New York. My best friend from college, who stuck it out and graduated with a bachelor’s in electrical engineering, never worked as an engineer. Instead, he became a CPA and now works in corporate finance.

Your 20s should be full of exploration. But don’t be afraid to change if you don’t like the direction you’re currently moving in, even if all your peers seem to be stampeding that way. Quit early; quit often if necessary. Until you find what’s right for you.

There’s no need to hurry

Gaining maturity and experience takes time. For evidence of this, just dig out and read anything personal you wrote from 5-10 years ago (diary entries are best). Chances are, you’d smile or shake your head at how simple your problems were back then, and how you wish you could be faced with just these problems today.

There are really no convincing arguments for getting a so-called “head-start” on life. People who start school early, enter the workforce early, or start a family early are no more likely to be happier or more successful; in fact, the opposite may be true.

Enjoy your 20’s – especially the first half. This is the period in your life when your time is most likely to be your own, when it’s the least valuable from a financial perspective, and when pursuing your dreams and other potentially risky endeavors carry the lowest cost of failure.

Before I turned 30, I’ve been a public-school English teacher (both in Canada and in Japan), an insurance and mutual funds salesman, a standardized test-prep instructor, a professional poker player, and an MBA applications consultant. I’ve held part-time jobs ranging from door-to-door paint salesman to Japanese restaurant cook. Each of these experiences forms part of who I am professionally, and some combination of them led me to my current role at the largest education company in China, doing a job that didn’t even exist before I joined the company.

Relocate more

Many people list traveling as one of their interests. Personally, I’ve come to dislike the conventional form of traveling – booking flights and hotels in advance for a weeklong whirlwind tour of a popular destination, frantically moving from one attraction to the next while fighting the effects of jet lag. How is this a fun or authentic experience?

However, I’m a huge fan of relocating to foreign locales for prolonged periods, long enough to have accumulated most local knowledge but not so long that the years blur together. In my experience, the ideal length is between three months and one year in any place that you do not foresee becoming a permanent home.

The reason, I’ve found, is that my memories are associated with the places they are created in. To give an analogy, it’s like my life is a book that is divided into chapters identified by location, and having multiple chapters has enriched my life immeasurably. The best way I can explain it is that they’re almost like entirely different stories based in different settings. Instead of having one decade-long story, I now have a collection of stories, with the same protagonist but in different situations, recollections of which evoke different emotions and unique twinges of nostalgia.

In my 20’s and early 30’s, I’ve lived extensively in four different countries – about ten years in Canada, one year in Japan, one year in the UK, and nearly three years in China. In an ideal life, I would trade most of those years in Canada for prolonged stays in another dozen countries.

As an older relative once told me, such experiences bring more colors to the palette that is life.

Be authentic

I remember a time when, as a schoolkid, I cared about the color of my lunchbox or the brand of my sneakers. It’s normal to care, because we are socially conditioned to place significant value on how others view us.

In direct opposition to this, here’s a critically important lesson that I’ve gradually internalized: consciously caring less about what others think of you, and instead caring more about what’s really important to you, is a huge step towards happiness.

In the past, I’ve altered aspects of myself in attempts to fit in socially or perhaps appear more attractive to the opposite sex. We’ve all been there. I’ve dressed differently, frequented places I had no interest in, hidden my interest in “geeky” things like video games and science fiction, pretended to enjoy certain genres of music, and basically done a host of other similar things just to gain acceptance from others. Please don’t do this.

Religion and fringe scientific theories notwithstanding, you only get one shot at life. Don’t spend it living out others’ expectations. Be proud of who you are and what you really want from the short time that you have.

We are often surrounded by people with preconceived notions of success and propriety. And so, as a counter to that, I’ll conclude with another piece of advice, this one given by Steve Jobs at a Stanford commencement speech in 2005:

“Don’t be trapped by dogma – which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.”