A while ago, I was having dinner with a friend. She jokingly mentioned that my biography should be titled “Beating the System” or something along those lines, because of all the stuff I’ve managed to get away with.

And in retrospect, she could be right. I’ve gotten away with a lot of things. Given the stuff I’ve done, I should have got into way more trouble than I have, and I should have been far from where I am now. But I’m not. Why? Partly, I think it’s because I’m capable of bullshitting my way out of most situations.

But that’s not what I want to focus on now, because I don’t think it’s the most important thing. I think the most important things is this: I’m willing to try and push the system. I’m willing to go against the system, to test the limits, and to take the leap and see what happens.

And I think that’s the first, and arguably most important step in beating the system. Having that willingness to take the risk, to stand by what you want, and go for it. Too many people, especially here in Singapore, worry about getting into trouble. They worry that if they test the rules, or the authority, that they will get completely screwed over and things will be horrible. But more often than not, that’s not true.

Of course, you don’t just break the rules for the sake of it. But if you see a rule that you think is pointless, if there’s a part of the system you don’t agree with, have the courage to go against it. Once you get rid of that fear (of getting into trouble, of being outcast, etc), you’re halfway there.

Taking the leap is half the battle won.

What’s stopping you from going against the system, and living life on your own terms?