The Surprising Upside of Insecurity
Magazine / The Surprising Upside of Insecurity

The Surprising Upside of Insecurity

The Surprising Upside of Insecurity

One time I failed at something I’d worked at for a long time. I felt terrible and spent a week moping around, complaining about it. My friends tried to cheer me up, saying, “It’s okay, don’t worry about it. You didn’t need that.”

But that’s not what it felt like to me. I viewed that kind of thinking as rationalization—the thing you do when your application to your preferred university is rejected, and you tell yourself “I didn’t really want to go there anyway.”

Of course you did! That’s why you paid whatever application fee was requested, no matter how ridiculous it seemed. That’s why you hassled teachers from long ago and anyone else you could think of to write nice letters on your behalf, and that’s why you slaved away for hours on the essay that hopefully someone on the application committee at least glanced at before putting in the “no” pile.

The answer isn’t to accept your failures; the answer is to get back up and find a way to succeed.

Sure, you can challenge or change the rules to suit your own purposes. You can define success however you see fit. But you shouldn’t accept less than your best. If your best doesn’t allow for failure, it’s not over.

Why “Safe and Comfortable” Can Lead You Astray

Do you worry about what people think of you? Do you worry you’re not doing your best? I do. I think about it all the time.

Of course, you don’t have to live your life the way others expect—that’s been the core message of The Art of Non-Conformity from day one. It’s the universal truth that everything else is built on.

But once you stop worrying about what others expect, is the answer to no longer seek approval of any kind? I’m not sure it’s that simple, at least not for all of us.

There’s a whole industry designed around helping people feel safe and comfortable, even when they’re stuck in bad patterns and aren’t achieving their potential. Love yourself! Accept who you are!

If your life sucks, that’s not what you need to hear. You shouldn’t set a goal of accepting mediocrity. Where are the people saying, “No, it’s not okay to be like that! Step it up!”

That’s what I want someone to say to me: Don’t settle, Chris. You can do better.

Maybe instead of not caring, coming to terms with your insecurity can become a driving force. Maybe it can get you out of bed when you feel like sleeping in.

Maybe it can help you put in the extra 2% of effort that transforms acceptable work into excellent work. No one has to lose for you to win—but you might have to struggle a little. It’ll be worth it.

I believe I’ll win in the end, and I believe you will too. Three cheers for insecurity! Now get back to work, whatever it is.


This post originally appeared on where Chris writes about work, travel, and the lessons he learns along the way.  

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