Breaking the Insecurity Cycle: How to Build Self-Esteem That Lasts

If you had seen pictures of me as a young girl, you would have noticed a shy, insecure kid standing slightly apart from the others. A kid that was literally the odd one out. Whose interests and accent placed her squarely outside the group.

That girl grew into a young woman who second-guessed every decision, who felt perpetually out of place, and who built her identity around what others thought of her. My self-esteem didn’t come naturally—it was something I had to deliberately cultivate through years of trial, error, and ultimately, radical honesty.

In this episode of No More Shoulds, our new Odder Being Podcast, I’m sharing my story and ways you can actually build a self-esteem that’s rooted in knowledge and a firm sense of self. Give it a listen above! Or, keep reading for a sneak peek into today’s conversation.

What’s at the root of poor self-esteem?

When we’re kids, we build how we feel about ourselves mostly from what others say about us. In my case, I got picked on for playing chess in high school and for my accent since I wasn’t born here. After hearing enough times that you’re “different” or “not enough,” you start believing it. We look at magazines, social media, or just listen to what people around us say, and think “that’s how I should be.” But here’s the tricky part—poor self-esteem isn’t just about thinking you’re bad at things. It actually makes your whole self-image blurry. You can’t clearly see what you’re good at or what you struggle with. Sometimes you might even swing the other way and think you’re amazing at things you’re not, just to protect yourself. Then when reality hits—like when you don’t get that job or someone doesn’t treat you the way you expected—it feels extra painful. You might even start thinking the world is against you, which just keeps you stuck instead of helping you grow.

Why self-esteem advice often fails

You’ve probably seen those self-help books that tell you to stand in front of a mirror every morning saying stuff like “I’m beautiful” or “I can achieve anything.” Sounds nice (and easy!) The problem is, this only works if you actually believe what you’re saying. But if there’s a voice in the back of your head questioning every affirmation you tell yourself, it’ll only make you more insecure.

That’s the big issue with most traditional self-esteem advice. It asks you to paper over your doubts with positive statements instead of addressing why those doubts exist in the first place. It’s like putting a fancy rug over a creaky floorboard—it might look better for a while, but you’ll still hear that creak every time you step on it.

When you try to convince yourself of something you don’t believe, you actually end up feeling worse. That inner voice gets louder, not quieter. “She’s lying to herself again,” it whispers, and now on top of your original insecurities, you feel like a fraud too.

What these quick-fix approaches miss is that real confidence can’t be faked into existence. Your mind is pretty smart—it knows when you’re trying to trick it. That’s why repeating “I’m confident” when you don’t feel confident at all just creates this weird internal argument where part of you is trying to believe something while another part is rolling its eyes.

So what then, should we just roll over and give in to our crippling feelings of self-doubt? Well, no. But listening to this voice and honestly facing yourself, flaws and all, might just be what you need.

Facing yourself head on

… on the podcast, we’ll talk about the way facing your deepest fears about who you are might actually set you free. As in the last episode, the second part is about doing some homework and applying what you’ve learned. Ready to listen? Hit play above or listen to the episode on Spotify or YouTube!

Ready to get honest about who you are?

Not to brag, but we did create card decks to do just that: help you get clear on where you stand so you can decide where to go from here. Order yours in our shop!