This Might Not Work

"When was the last time you did something for the first time?"

This quote by Seth Godin in one of his books, ​Poke The Box​ stood out to me.

And in an interview with Tim Ferriss, he says:

If I'm not saying to myself, 'This might not work, '… then I haven't pushed myself hard enough.

That line has stuck with me for years. Not because it’s motivational fluff, but because it’s brutally honest. Anything that matters carries a real chance of failure.

Think about it:

• Launching a new business.
• Writing online when no one’s reading.
• Saying yes to a role you’re not fully “qualified” for.

Each of these comes with the whisper: this might not work.

My Track Record of “Might Not Work”

Looking back, almost everything meaningful I’ve done started this way:

Selling $5 logo design gigs on Fiverr as a college kid in Malaysia. It might not work… but it was my first USD income. Starting a specialty coffee blog. It might not work… but I learned content marketing from scratch.

Writing WordPress themes for ThemeForest. It might not work… but I built skills I still use today. Publishing answers on Quora. It might not work… but I became a Top Writer and built an audience.

Cold emailing Noah Kagan. It might not work… but it led to seven years at AppSumo.

And more recently:

• Launching Wolo Yoga in 2021. Competing with established US brands? It might not work… but today we’ve sold thousands of mats—only in Malaysia alone.
• Restarting this very newsletter after nearly two years away. It might not work… but it feels right to start again.
• Posting a reel a day on Instagram and TikTok. It might not work... but it helps me focus my energy on producing rather than consuming.

Why This Matters

Most people treat “this might not work” as a warning sign. A reason to stop. But the truth is the opposite: it’s a compass.

When you hear it, it means:

• You’re playing at the edge of your abilities.
• You’re choosing growth over comfort.
• You’re doing something that actually matters to you.

It doesn’t guarantee success, but it guarantees meaning.

The Flip Side Isn't Failure

Of course, plenty of things I’ve tried didn’t work. Projects fizzled. Ideas died quietly. That’s the cost of playing the game.

But here’s the key: the opposite of “this might not work” is not “this will definitely fail.”

The opposite is: It might just work.

And if you keep putting yourself in that zone—again and again—you give yourself more chances for breakthroughs that change your life.