An image of a child as an example to show that we can still feel like we're not good enough, just like when we were kids.


Not Good Enough? Me Neither. Now What?

Craig Dockery

9 mins

That’s right. You. Totally insecure.

How do I know? Because I’M insecure. Behind the appearance of a real grownup with a job and a family and a respectably-sized television, deep down I’m still a 7-year-old kid who’s worried that people won’t like him. Who still feels like the weirdo in the room. Who remembers the time he tried to be friends with that one Asian kid, and that Asian kid was totally an a-hole to him. Who now wonders if he’s insecure AND racist.

Thanks to my lifetime of experience as an expert in insecurity, I can help you. Heads up: part of the answer involves God and stuff, but don’t let that scare you away. Seriously, this insecurity business ends in a really positive place. So keep reading, you pathetic loser. (Kidding! Hopefully.)

We’re all insecure.

Turns out most of us secretly worry that one day soon, we’ll be outed as frauds. Total phonies. Fakes. Even those of us with long track records of being successful, likeable, or whatever it is we’re seeking. So we compensate. Here are the four masks we use to cover up our insecurities. See if one of them sounds familiar):

  1. The Pleaser.
    You’re here to help. You’re the guy who’s always there in a pinch. The one who will let anybody borrow his motorcycle. Who helps acquaintances move. When recipients of your generosity tell you how much of a help you are, you shrug it off like it’s nothing. But it’s EVERYTHING. You secretly need constant validation to prove to yourself that you’re doing okay in life. Don’t worry. You’re not alone. I’ve been there. I was there like two days ago.

  2. The Achiever.
    You’re similar to the Pleaser, because you’re still hell-bent on proving that you’re doing okay in life. The difference is, you do this by winning instead of helping. Same thing. If you’ve become exceptional at something, whether painting or spreadsheets, this is probably you. Or if you’ve ever bought something just to impress somebody, you might be this guy. Once again, I know you. You’re my people.

  3. The Hider.
    You opt out of the whole situation. Your game plan is to never be noticed, and therefore never found out. It’s a good plan, and sadly it usually works. I’ve spent more than a few days as a Hider.

  4. The Rebel.
    You worry that people don’t think you’re not good enough, so you’ve come up with a brilliant strategy: you reject THEM, before they can reject YOU. You build up a thick skin, so that nothing can penetrate your heart. You don’t give a shit. Words can’t hurt you. I haven’t had much chance to play The Rebel, but some of my best friends have been Rebel experts. I love those guys.

I totally made all four of those up. If you think of better ones, let me know. MY POINT IS THIS: we make up for insecurities in all kinds of different, even conflicting ways. But we’re all insecure for more or less the same reason.

We are insecure because we’re afraid that we are not good enough. We are frightened that somebody will discover our shortcomings and call them out, in front of everybody. That would be the worst.

Now here’s the deal.

You are not good enough.

No, I’m serious. THAT’S THE THING. None of us are good enough. We’ll all totally drop the ball at one point or another. We’ll miss the game-winning shot, or lose the big account, or disappoint our whole family on national television (wouldn’t that suck?). But that’s the beauty of it. Nothing pile-drives Insecurity like owning up to our failures and our shortcomings. It’s so freeing and beautiful and unexpected. Admitting our weakness only makes us stronger, like some kind of judo move for our souls.

These are the top three benefits, that I also just made up, of admitting your own weaknesses.*

*a note on admitting weakness I mean, don’t do it ALL the time. Think of this skill like salt in the recipe of life—a little bit goes a long way. Nobody wants to eat straight salt. Likewise, nobody wants to be around Debbie Downer every single day. Take it easy on yourself, alright? Admitting weakness shouldn’t be a pity party. You are not a victim.

Admitting your weaknesses makes you more relatable. Everybody wants a friend who can sit with them and say, “I’ve messed up too.” That’s the nice way of saying, nobody wants a friend who slings advice left and right. The ability to point out your own insecurities and flaws makes you more approachable to friends, to co-workers, and—this may be the hardest one—to family. It shows that you’re self-aware, and that you don’t take yourself too seriously. The simple version: when you can admit your weakness from time to time, you’re way easier to be around.

Admitting your weaknesses makes you more trustworthy. If you’re in any sort of leadership or position of influence, it’s a huge deal to be able to admit weakness in the right circumstance. You’re called upon to cast vision and to take your people to a new place, but there are moments where you simply need to be human. And if you can admit a misstep or a failure in the appropriate place, your authenticity can bolster trust in a huge way among the people who follow you. Your people know that you’ll be straight with them no matter what. And trust might very well be the most important thing a leader can possess. Besides year-end bonuses.

Admitting your weakness frees you up to make a difference. Covering up your insecurities takes a lot of energy. It’s draining, holding up that “I know everything” mask all day long. Why not drop that ugly thing on the ground, and spend your effort doing something meaningful? I used to be scared to ask questions in meetings, because I didn’t want to look stupid. All that did was delay the inevitable. If I never got an answer, of course I was going to look stupid eventually. Just admit when you don’t have it all figured out. Chances are, you’ll get the answers you need. And It’ll feel like you just took a 5-Hour Energy. FOR YOUR MIND.

Weakness makes you stronger.

None of this is my idea. I got it right out of the Bible. You may have heard of Paul, also known as the Apostle Paul. This guy who lived right around the time of Jesus, and he spread Christianity through much of the Roman Empire. Paul wrote a bunch of the Bible. No matter what you believe about faith, it’s pretty obvious that this guy was a beast. He’s way up there, in terms of the most influential people of all time.

Yet Paul talked a lot about his own weakness. In one letter to a church he started in the town of Corinth, Paul said, “remember when I first showed up? How weak I was? And how my words were all fumbly? That’s proof of God’s power, not mine.” In another letter to the same folks, he gave us the line to remember. Paul mentioned a big struggle in his life, and how he prayed for God to take it away. And Paul writes that God said this: “my grace is sufficient for you, for my power is made perfect in weakness.” What! You’re saying the power of God is connected to our weakness? Strong. And Paul’s reaction? “Then I’m going to brag about my shortcomings! Because when I’m weak, then I’m strong.” (That’s my paraphrase; here’s the actual passage.)

Let’s assume the Bible is true for a minute here. And we know Paul is one of the most influential people in the ENTIRE HISTORY of the Christian faith. So he probably knows what he’s talking about. And he says that the best way to be strong is to admit, and even embrace, our weakness? Not only that, Paul says that all we need is God’s grace, and God’s power covers up all our shortcomings? Well shoot. It’s probably worth trying.

Just try it.

Okay, Mr. Insecure. I bet it still sounds scary to admit your weaknesses or insecurities out loud. But what do you have to lose? An awkward conversation? Big friggin deal.

Here’s your assignment. (Do this in the next seven days.)

Find a friend you trust, somebody who will listen. Buy that friend a beverage as a “thanks in advance.” Share something that you’re insecure about, and see what happens. And give that friend a chance to share his own insecurities if he wants. (There’s a good chance he’ll have worried that you called this meeting to finally out him as a fraud.) In my circle of friends, we call this “The Final 5%.” That is, the last little bit that you hold back, that you’re scared to admit out loud. Go for it. Share the Final 5%. I’ll bet you experience a taste of the same thing that Paul experienced — unlocking the actual grace and power of God himself.

If none of this works for you, I don’t know what to tell you. Maybe try imagining everyone wearing banana costumes. Sometimes that helps.

Craig Dockery
Meet the author

Craig Dockery

Human. Average height. Pants wearer.

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