Lone gentoo penguin

A few weeks ago, I was invited to return to my alma mater to give a talk at their Career Day for graduating students. I realized after the Q&A session that Asian education systems still preach the mantra that if you do well in school, you would get a great job and earn lots of money, and the reverse is true as well…End of story. But in this new digital, post-industrial economy that we live in now, the reality is so far from that. The education system hasn’t kept up. This type of mentality that the system decides your worth based on its rules and standards, regardless of individual quirks and talents, does not equip the new generation to compete effectively in the new economy.

You are the CEO of your life. By being the CEO of your life, I don’t mean that you should just do whatever you want, or act antisocially, with wanton disregard for the impact of your actions on others. I mean that it is a long term winning strategy to have an entrepreneurial mindset about your life and career. That entrepreneurial mindset includes finding your strengths and focusing on them, investing in long-term value, taking the unbeaten path, and having a healthier relationship with failure and disapproval. When you become CEO of your life, you will start to think harder about what you can do and the decisions you can make to take you on the path you want, instead of bemoaning external circumstances, rejection and failure. It’s very liberating and empowering at the same time.

1. Find your strengths and focus on them.

Take the time to understand yourself, and you will find your strengths. Invest in yourself and in those strengths. Then, find a way to express yourself in a way that’s uniquely you. I wrote about how Ellen Degeneres and Taylor Swift have built their careers through capitalizing their biggest strengths, humor and singing/songwriting, in a previous post. This is the YouTube and self-publishing generation. You can publish music, books, photography, art, and frankly any other skills under the sun, even those previously deemed economically useless to know, like makeup or gaming, as long as you are good at it. These “side” pursuits that people around you dismiss as useless, can sometimes lead you to amazing opportunities in your career and life, doing exactly what you love to do most, or what no one else but you are best at doing.

The one rule is this: be you. For me, this website is the medium that I’ve chosen to express myself through. Oh, and my Youtube channel of course (Please subscribe!). And there are so many benefits to starting this website, both personal and professional, that helps me to become the CEO of my life, baby step by baby step, every single day.

2. Invest in long-term value and you will see the opportunities that others don’t. Don’t be afraid to take the unbeaten path if it feels right.

My story: When I was a sophomore in college, I made the inspired decision to major in the liberal arts (which turned out to be history) instead, and transferred out of business school, where I was studying finance and accounting. At that point in time, I recall people in school, friends, and even friends’ parents, giving me one of two responses: 1) Those who cared advised me against it because it wasn’t wise or “practical”, to study something that would certainly lead to career doom and gloom, or 2) Those who didn’t care stopped hanging around me, since I’d been written off as someone no longer of value to furthering their future networks. A lot of people thought I was being weird. The only reason why my parents didn’t object was because they didn’t know what either the liberal arts or finance meant, and relied on my better judgment to decide what to study! It was daunting to face disapproving words and looks. But, two years later, when I graduated into the GFC of 2008, I joined Goldman Sachs as the only new analyst hire (i.e. not a returning intern) out of the US.

Moral of the story: No, it most certainly is not that I’ve succeeded because I landed in Goldman Sachs. This is a trap in thinking about success, and if you thought that, it should indicate to you that you now need to read on to hear what I have to say about being the CEO of your life. The moral of the story is that I grabbed what I personally saw as a once-in-a-lifetime opportunity to invest in my long-term value. I saw that, in my personal educational upbringing, I didn’t have much critical thinking and communication skills. I had a curious mind and I wanted to cultivate it by reading the liberal arts. I figured this would be most useful to me personally in the long term, compared to what I was then learning in business school. This ended up having the unintended effect of me building a different set of combined competencies to my competition. When you choose to take the unbeaten path instead of the well-trodden, “practical” path, you stand out:

Stand out from the crowd

Regardless of where I go and what I do for life and work, those foundation critical thinking and communication skills continue to manifest in the different life and career decisions I have made, and take me to amazing places. I love the journey. To become CEO of your life, start thinking about long-term value and you will start to see the opportunities that others don’t. Seize these opportunities and take the unbeaten path.

Oh and, all that glitters is not gold. After almost 4 years at Goldman, I decided that it really wasn’t what I wanted to do. I left before I found another job – again against all wise and practical counsel(!) – and it led me to discover the world of technology and startups, which I now know is where I want to be, and where I want to make a far bigger difference.

3. Build a healthy relationship with imperfection, failure, rejection and disapproval.

This is the hardest one for people to accept, particularly in Asian culture. We are all brought up (and I think especially so in Asia’s infamously intense exams culture) to associate failure with bad social and economic consequences. And because of this educational upbringing, when people fail, they don’t think that they just failed the test or got rejected by the school they wanted to go to or company they wanted to work for – they are largely made to feel like they have in fact failed at life. And if they fail, woe betide them…Or does it?

Failing and getting rejected may not be bad things. More importantly, failure and rejection happen everyday, to almost everyone. It’s definitely more common and prevalent than everyone else on Facebook and LinkedIn has us think. I can think of so many instances where I’ve felt like a failure, only to realize later on what a blessing in disguise it was, or what a huge learning lesson it was that made me so much better at doing something else.

Writing this blog is a big step towards getting used to failure and rejection. There will undoubtedly be haters, and people who don’t think much of this and won’t read it. But there will also be people who will read this, love this, and benefit from this. I write for these people. This is my Minimum Viable Product, which I plan to keep building!

Being afraid of and quick to judge failure and rejection, prevents good risk-taking and crushes innovation and entrepreneurship. The point is not to fear failure and avoid anything that could result in failure. The key is to harness lessons from failure and rejection, keep bettering your game, and practise what the famous venture capitalist Ben Horowitz in The Hard Thing About Hard Things calls, “the ability to focus and make the best move when there are no good moves…It’s the moments where you feel most like hiding or dying that you can make the biggest difference as a CEO”.

You are the CEO of your life. Don’t forget that!

Do you have suggestions on other ways to become CEO of your life? If so, leave a comment! I’d love to hear from you.

6 thoughts on “How to Become CEO of Your Life

  • July 28, 2014 at 01:44

    So insightful! Love it 🙂

  • July 29, 2014 at 09:35

    Amazing posts =) keep it coming song!

  • July 29, 2014 at 10:27

    You should consider a career in this!

  • February 26, 2017 at 07:43

    excellent and honest story that i stumbled on. I look forward to following your website

    thx kevin

    • March 1, 2017 at 22:13

      Thanks Kevin! I’m glad you enjoyed the read. 🙂 I’d also love to hear if there’s anything in particular you’re interested in reading about on this blog!


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