When I was a kid, I played this game where you had to defeat a series of monsters. In the final level, the boss wasn’t a dragon or a demon..
It was you.
You had to fight against yourself, with the same armour and weapons.
Dorky, I know.
But actually, I think the game devs (and my 11 year-old self) had stumbled upon one of life’s greatest truths:
The biggest barrier to your success isn’t a boss or co-worker…
It’s you.
And when you shift the focus from fixing the world to fixing yourself (by facing your insecurities & weaknesses) most of the time, the world changes to suit.
So today, I wanted to riff about an insecurity I struggled with, which gave huge ROI in conquering it:
Shyness.
🤥 The big lie of shy
I used to think shyness was something we’re born with.
You’re either shy, or you aren’t.
But the way I see it now, it’s just a fear to overcome - a fear of negative judgement, awkwardness & social discomfort.
And just like Bruce Wayne could only become Batman by conquering his fear of bats, imo, we can only become the best versions of ourselves if we beat shyness.
Because when you think about it…
💵 Shyness is expensive
How many times have we stayed silent in meetings…or not put ourselves out there, because we rejected ourselves out of fear first?
Really…
Shyness is a silent tax on your potential.
You’ll never know the opportunities you could’ve had, the connections you could’ve made, the ideas you could’ve shared, or the raises you could've asked for…
Because like MJ said:
You miss 100% of the shots you don’t take.
🥸 Shyness’s many disguises
In Good Will Hunting, Will’s therapist asks Will– a mathematics genius - why he lays bricks and mops floors for a living.
His reply?
Will gets defensive, and says that moving bricks is an honourable profession.
His therapist shoots back:
(paraphrasing)
“Honour. Yeah, that’s why you sneak about at night-time solving math equations at the most prestigious university in the country.”
What’s going on?
Will’s using a good reason (honour) to disguise his real reason for not pursuing a more challenging career:
He didn’t want to put himself out there, in case he failed.
As for me?
I did similar mental gymnastics to disguise my reasons for being shy:
😶🌫 1) “I’m just introverted.”
Introversion has nothing to do with shyness. You can be an introvert, and still put yourself out there. Being quietly confident IS a thing.
🤓 2) “I’m being respectful!”
Suuuuure. “Respect” was why we don’t contribute to meetings, or ask someone for help. But being respectful doesn’t mean self-erasure.
👺 3) “I’m humble!”
Confident, extroverted people can still be humble.
Why’s it crucial to call out your BS?
Because it’s only by doing so that you can…
🥷 Turn shyness into courage
Here’s the reframe:
Shyness isn’t good. It’s just a bad habit, the antidote to which is exercising your courage.
How d’you do this “exercising”?
Here are some tactics that actually work:
🏷️ 1. Recognize the self-assigned label
Most of us don't realize how much power our self-identity has over our actions. The moment you labeled yourself as "shy," you created a framework that justified and reinforced avoidance behaviors.
The first step isn't a grand declaration or correcting others - it's simply noticing when you're using this label as an excuse. "I can't do that because I'm shy" becomes "I'm choosing not to do that because I'm uncomfortable."
This subtle shift acknowledges that your behavior is a choice, not an immutable characteristic.
🤔 2. What's the worst that could happen?
Let's say you're afraid of speaking up in a meeting. Instead of trying to downplay the fear, magnify it to the worst-case scenario.
E.g: You speak up → someone clarifies your question → everyone forgets → you feel terrible for two weeks anyway (that’s normal).
Why does this work?
One of our biggest fears is fear of the unknown.
Although it might seem like we're amplifying fear, we're actually putting a hard limit on it, making it easier to deal with.
🧩 3. Start with low-stakes situations
Build confidence in environments where the consequences of social "failure" are minimal:
- When ordering coffee, ask the barista how their day is going instead of just stating your order
- Make a brief comment to someone in the elevator instead of staring at your phone
- Practice articulating your thoughts with trusted colleagues before speaking up in larger forums
These tiny interactions cost you nothing if they go poorly (which they rarely do), but consistently build your social muscles without the pressure of high-stakes situations.
💪 4. Leverage your strengths
Sometimes the most effective way to overcome shyness isn't by forcing extroversion, but by leveraging your natural strengths:
- If you're better in writing, establish yourself through thoughtful emails or documents before speaking up in meetings
- If you're more comfortable one-on-one, build relationships in that context before navigating group settings
- If you're knowledge-driven, use thorough preparation as a confidence booster
Confidence isn't built by pretending to be someone else, but by finding ways to authentically engage that play to your advantages.
📋 5. Use preparation as a confidence tool
Often, shyness feels worst when we're caught off-guard. Strategic preparation can create a foundation for confidence:
- Before meetings, write down at least one point you could contribute
- If you know you'll be meeting someone new, learn a bit about their background first
The goal’s to have enough structure to lean on when nervousness hits.
🌿 Courage compounds
Each small act of bravery makes the next one easier. The colleague you finally approached might introduce you to your next client. The question you asked in a meeting might lead to a project that showcases your talents.
Unlike most things in life, the return on investment for overcoming shyness is exponential, not linear.
The tax you pay for shyness compounds too. Each opportunity missed leads to other missed opportunities down the line.
So ask yourself: What's one small thing you could do today to start building your courage muscle?
Start there!