Before the pandemic, I was at dinner with a couple of girlfriends who also happen to be business owners. We were chatting through a particularly difficult decision one of us had to make in regard to a new venture. Over plates littered with shrimp cocktail tails, we slung personal stories across the table, about times when we’d doubted ourselves and were ready to call it quits; about why it was ok to let some businesses go; about what kept us hanging on.

Forty-five minutes later, we found ourselves circling back to one friend’s problem in particular. It ultimately came down to a question of confidence: Did she believe in the idea? Did she believe she was the best one to lead it? And would she believe in her idea, even when the people closest to her did not?

Think about a time when you had to make a similar choice. How confident were you in yourself? In fact, I want you to rank your confidence on a 1-10 scale (10 being the *most* confident). This was what one of my friends asked the group to do that night over drinks. 

“Four.” I blurted out. A measly four. I kinda, sorta, maybe, probably didn’t think Wit & Delight would ever be anything when it started. What was interesting to me was that most of the women in the group rated their confidence levels around an eight. When they started their businesses, they had a pretty good belief in themselves and their ideas. What made me rank my own confidence, so instinctively, at such a meager level?

I think about self-confidence a lot. How to find more of it…but not too much. Like it’s an elusive magic pill that will somehow make all my troubles evaporate into dust. 

We acquire self-confidence through a series of choices that are infused with the belief that we’re valuable and deserving of being treated well. We build confidence one habit, decision, boundary, or self-care act at a time. 

Yet what I notice, more and more, is that self-confidence isn’t something you can buy; it’s not something you can life coach your way toward. We acquire self-confidence through a series of choices that are infused with the belief that we’re valuable and deserving of being treated well. We build confidence one habit, decision, boundary, or self-care act at a time. 

It’s a gift only we can give to ourselves.

And yet we aren’t supposed to be self-centered, and we better not be putting ourselves before others. We’re told confident women are difficult, full of themselves. We’re told that the most “attractive” women are the ones who “don’t know it.” (What a pile of hot garbage that is.)

This month on Wit & Delight, we’ll be exploring the many ways self-confidence plays a role in the choices we make and the company we keep. Where does self-confidence come from? How do we foster it? Why do we lose it? And what can we do when we’re feeling unconfident?

In the month ahead, our contributors will be making a case for less apologizing, and diving into the meaning behind body neutrality. They’ll be exploring the correlation between creativity and confidence, and what they learned about confidence while dealing with a chronic acne breakout. I’ll be sharing lessons I’ve learned from ten years in therapy, questions to ask yourself before redecorating your space, and more. We can’t wait to share all that we’ve got on the docket with you in the coming weeks.

As we move through October, we’ll be approaching the topic of self-confidence through the lens of how it relates to our careers, our relationships, our senses of style, and more. We’ll be exploring how a belief in ourselves and a conviction in our ideas can propel us toward a more meaningful way of living.

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Kate Arends

Kate is the founder of Wit & Delight. She is currently learning how to play tennis and is forever testing the boundaries of her creative muscle. Follow her on Instagram at @witanddelight_.