My Semi-Embarrassing (But Effective) Tactic For Dealing With Low Self-Confidence

I’ve made it no secret that I often feel like I’ve struggled with my self-confidence. I don’t see the point in hiding it. I think struggling with low self-esteem and insecurity is super common — especially among women, as I’ve gathered from many talks with and observations about friends over the years. For me, it results in sometimes being less friendly with other people than I’d like to be, occasionally second-guessing my own decisions, feeling anxious about asking for what I want, and often feeling like I’m doing something wrong.

For example, I have a quick phone call with my accountant later to go over my quarterly tax payment. (Yes, I have to send it by this weekend and I’m a procrastinator.) I’ve had many accountant meetings over the past year or so, because I earn my income from multiple sources and my taxes aren’t as straightforward as they’d be if I had a more “traditional” salaried job. I should be used to them by now, but somehow they always make me nervous and stressed — like I’m going to find out I’ve done something completely wrong, despite the fact that I always pay my taxes and know I have plenty of savings stashed away to cover them. Not to mention that I’m the one paying for this service.

Without pinning all the blame on Society, I’m not sure where this comes from. My mom is one of the most comfortably confident people I know. She’s worked for the same company for 25 years, climbing the ranks to the point where she’s super well-respected by everyone there, at least from my vantage point. She always dresses professionally, but also like herself — she’s never shied away from an outfit because someone might think it’s too feminine or colorful or bold. She’s always upfront about what she wants from situations (while still being considerate of others), and she’s goal-oriented and open with others when she decides she wants to make a change in her own life. Growing up, she always, always taught me to be my own advocate.

And while I like to think I’ve inherited some of this (especially the eschewal of a more “traditional” neutral wardrobe), I know I have a lot of work to do. My lack of confidence has landed me in different situations that I’m less than thrilled about, from small things like being anxious about speaking to my accountant to big things like the time I worked without pay (when I was supposed to be paid) for two months because I couldn’t face the fact that I had other options.

And I hate to admit it, but one of the things I often feel insecure about is my money situation. I 100% know that a person’s worth isn’t and shouldn’t be defined by their earning potential, and for the most part, I don’t think of myself in those terms. But there are moments when the ground feels shakier than it actually is. I’ll be so excited to see that I’ve had the best month of my life so far income-wise, then hear about how a friend negotiated his already-six-figure salary up 15% more. I’ll walk around in an adorable neighborhood and look up the rent prices for a building just for kicks, only to see that I’d never be able to afford a studio in it, probably ever. I’ll be so excited searching for a cute, affordable Airbnb for an upcoming trip, then see my friend from high school is on literally their third international trip this year to Mexico or Tel Aviv. It’s sometimes hard to not feel like I’m behind or less successful than everyone else my age, even though that’s far from true.

There are plenty of things I do to make myself feel more confident on a day-to-day basis. I take care of my skin, blow-dry my hair, go to yoga classes, wear eye makeup, spend time out in public alone, make sure I keep up with the news. But there is one thing that helps with my self-esteem more than anything else: going through a list of things about my life that would look incredible to my 16-year-old self. It’s honestly very silly, but if I’m feeling insecure about anything, I’ll even go so far as to write them down, in a way that makes it feel like I’m telling that 16-year-old girl about someone else. Some examples:

She lives in a cute apartment — in Manhattan!

She lives with her boyfriend, who she’s been dating for two years. (Meaning she’s BEEN on DATES.)

She can pick up a bottle of wine on the way home and she’s old enough that it’s not even remotely a big deal.

She has cool friends who do things like invite her to their comedy shows and travel to Europe with her.

She has a cat! (You haven’t figured this out yet, but cats are great.)

 She’s literally a published writer. 

These aren’t necessarily things that look good “on paper.” While some things about my life look great on paper (has been published, has retirement savings account), others aren’t exactly impressive (net worth is, uh, getting there), the things that make me the happiest and most self-assured are the ones that reflect the kind of life I always wanted to build for myself. Some of them are things I’ve worked hard for, some were born from luck, and some were inevitable. The point is, it’s easy for me to feel like I’m behind or unsuccessful when I compare myself to other people, and it’s impossible not to do so. But I have to remind myself that I have plenty to be proud of, and it’s easier for me to feel self-assured when I realize how impressed I would have been with myself when I was younger. I know I’m not “done” — life isn’t something that just happens to you one day, and I’m still building the life I want.

Maybe the life you dreamed of when you were 16 looks nothing like the life you actually want for yourself today, and that’s okay. But maybe there’s something to treating yourself like a stranger you’re hearing about for the first time. It gives you a new, more objective vantage point to appreciate everything you’ve got — even just the fact that you have things that make you happy at all. There are probably at least a few things you’d be impressed with. For me, confidence comes from focusing on the positives, and recognizing how lucky I am to live the life I’m living — even if it means I have to complete this silly little exercise to do so.

Holly is the Managing Editor of The Financial Diet. Follow her on Twitter here, or send her your ideas at!

Image via Pexels

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