Why you should always be the underdog — and how it helps you win beyond anyone’s expectations

Do you like it when people underestimate you?

I do. As an underdog my whole life, from a scrawny disadvantaged kid to a new entrant to industries, I’ve put myself in situations where it’s not clear I’ll make it. As a result of my experiences, I’m truly passionate about staying the underdog, and stanning other underdogs.

Here’s my ode to the underdogs, and how it’s going to help us make it (to the next meaningful underdog gig!).

#1: You stretch yourself more than ever

It means you are putting yourself in unfamiliar territory, and showing up with courage.

Being an underdog in any circumstance means you’re taking risks, and growing fast. You’re open to learning; you’re adapting to change.

#2: You challenge others where they’ve grown numb

You play like a challenger as an underdog — you spot the opportunities where people have grown blind to them.

You have fresh eyes, and you take the time to reinvent (since you never knew the status quo to begin with!). You look in unexpected places, and create differently.

#3: You delight by underpromising, and overdelivering

Most people didn’t think you could do it anyway.

You can surprise and delight (mostly for your own sake) by turning up with exceptional, groundbreaking work.

#4: You temper yourself for the long haul

You’re in it to make a difference, and being the underdog breeds humility.

In Chinese (I’m Singaporean, so I know some), there’s a saying: 深藏不露 (shēn cáng bú lù). Positively interpreted, it means that even if you have knowledge and talent, you should temper yourself and learn humility, and not be flashy or overbearing with others.

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As you become ever more successful, will you keep putting yourself in the position of an underdog? By continuing to run over demanding situations and growing upwards, every underdog will have their way!