How to relate with (and help) an insecure person

…without driving yourself nuts

Everyone knows and has to relate with an insecure person. Maybe it’s your boss, or a colleague, or a friend, or a spouse. This article is for the scenario where the insecure person is someone you care about — which probably rules out boss and colleague, but who knows? (Not that I couldn’t write one to help you with the ones you don’t care about, but you don’t care about them anyway, right?)

To begin, let’s talk about…

The question of insecurity

Here’s a way to think about it: Insecurities are the questions that trouble people on quiet nights when they’re alone.

“Am I good enough?”
“Am I loveable?”
“Am I worthy of acceptance?”
“Is there anyone I can trust?”

These are fundamental questions, and nothing short of personal identity is at stake for anyone asking them. And they may have been raised in childhood, by life experiences, traumas or just the way one’s personality is wired. Whatever the case, they’re there. There are times when they’re quiet, but one day—or more likely, one night—they resurface. They always resurface.

“Am I good enough?”

And even when (as is most often the case) the person is unaware of these insecurities, the questions they raise continue to drive their fears, rollercoaster their emotions, deflate their happy moments, and jeopardise their closest relationships.

Especially that last one, which is what this post is about.

“Does anyone really like me?”

Hauling around these unanswered questions like so much baggage, people stumble into relationships and demand that you person answer them. But often, them themselves can barely articulate the questions they insist you answer. (Confession: I was well into adulthood before I could even name one of my deepest.) I’ve seen elderly people who don’t seem to have ever actually given words to theirs.

The problem with insecurities, though, is they’re not questions you can answer for anyone.

“Am I worthy of acceptance?”

Not that you can’t try. It’s just, no answer can possibly be good enough. And none is certainly final enough. You can’t prove to anyone that you love them enough to make them stop wondering if they can be loved. No achievement will make them feel successful enough. No degree of commitment is enough to permanently silence their inner voice of distrust.

“Is there anyone I can trust?”

Trying to answer these questions for anyone is an exercise in futility. The harder you try, the harder you’ll fail. And sometimes, when people have done all they can, they give up and walk away—or stay, deeply resentful.

But you probably know about that already, right?

So how can you help?

First, two things you just shouldn’t do. Don’t attack the question. (Like, “What kind of question is that?”) And don’t answer it glibly (Like, “Of course you’re acceptable!”) The first one shuts down the question, the second downplays its importance to the person. Don’t do either. And don’t try to answer the question for them, either. (I know, I said this already, but it bears repeating.) Instead…

Empathise. You have, after all, asked similar questions (although you must never imagine them to be exactly identical). And even if their questions are significantly different, you at least are familiar with what it’s like to question yourself. (At least I hope you are.) So empathise: enter into their questioning and be right there with them. You’ll be amazed how far that goes. (You may even be the one to help them actually voice out the questions!) And if you’re wondering how best to emphathise: my best advice to you would be (warning: you might not like this)…

Channel your own insecurity. If you’re like most people, your likely answer would be, “I’m not insecure.” But think about it for a minute: have the insecure people you’ve known generally considered themselves insecure? Insecurity is the kind of thing that’s far easier to see in another person than in our own selves — a blindspot. And yet, again and again, I’ve found the most secure people to be those who are well aware of their insecurities, and it’s those who don’t acknowledge theirs, or who push them off to others, who tend to be most insecure. If you have faced your own insecurity, then you already have the tools to help someone else with theirs.

If you aren’t aware of any insecurity, though, then you’re either a true saint…

Or very insecure indeed.


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