If You're Going To Doubt Yourself, You Might As Well Make It Amusing

On launching—and laughing—in the face of failure.

I can’t count the number of times over the past six months that I’ve opened up this website and stared at a blank screen, willing myself to write something—anything—that feels worthy of blasting out into the world. My computer desktop is littered with half-written essays that have yet to turn into anything, and there are dozens of text messages to me, from me, with barely-formed ideas (most of which I came up with while stoned) like, “We’re not babies anymore!!!” and, “Should I write a children’s book about my anxious poodle?”

When I left my job, my number one priority was taking the space to foster my creativity and start building a platform where I could write for myself (and maybe even make money doing it!). Six months later, I haven’t really done either of those things. And recently, I’ve started to question why the hell it’s been so hard.

What I’ve come up with is two-fold: 1) I’m paralyzed by imposter syndrome; and 2) I’m scared to death of failure.

Obviously, neither of these fears is unique to me—nearly everyone I know feels like they’re cosplaying as an adult, and you’d be hard-pressed to find anyone who enjoys shitting the bed on something they’ve worked hard for. But realizing just how deeply they run—and how significantly they’re standing in the way of me achieving my literal dreams—has made me want to put on my big girl pants and do something about it.

First up, the “I don’t feel like I’m good enough” of it all. Imposter syndrome is, apparently, so pertinent that it’s landed a spot in the literal dictionary, which defines it as, “The persistent inability to believe that one's success is deserved or has been legitimately achieved as a result of one's own efforts or skills.” Anyone relate? Because I sure as hell do.

My résumé's got an Ivy League journalism degree, five years as an editor, and bylines from dozens of major media outlets. I’ve won awards, led panels, starred in a YouTube series, and hosted a Podcast. But even still, when I sit down to write anything that hasn’t gotten another professional editor’s stamp of approval, all I can think is “Who the hell would ever want to hear what I have to say?” (followed immediately by, “And why would they ever want to pay me for it?”)

This mentality has played on loop for as long as I can remember, providing a real mindfuck of a soundtrack to everything I’ve ever done. No matter how many people tell me I’m worthy of betting on my talent (thanks, mom!), I’ve never quite been able to believe it for myself.

Then, last month, I found myself in a writing workshop with the brilliant Alyssa Shelasky, and asked her the exact question that’s been on my mind these past few month: How do you know when something you write is good enough to share with the world?

Her answer went a little something like this: “You don’t. But once you start thinking of yourself as a writer—and calling yourself that out loud, when people ask you what you do—you’ll be surprised how much more easily it comes.”

I’ve spent years trying to figure out a way to talk about what I do—and what I’m passionate about—in a way that feels legit. Calling myself a writer has always felt ridiculous (see: imposter syndrome), so I’ve defaulted to some form of “I’m a freelance women’s lifestyle journalist” or “I’m a beauty editor with a focus on wellness” or some other word salad lest anyone think I was foolish enough to consider my “art” (another term that feels ridiculous) an actual career.

But… I am a writer. If I wasn’t, I sure as hell wouldn’t be spending my Tuesday night pouring my heart and soul out to the Internet, and would likely have a whole lot more money in my bank account. In the few weeks since Shelasky handed down her advice, I’ve made it a point to repeat that so-simple-it-feels-stupid statement to myself—and anyone who cares to ask—as much as humanly possible. And believe it or not, it’s working, because here I am actually writing.

As it turns out, the trick to getting over all this self-doubt might just be… believing in yourself? Someone tell Dr. Suess he was right.

Next on the list of “things I’m working on in therapy” is my debilitating fear of failure. No one likes to fail, but my situation feels... different than that. My anxious, type-A brain can take any single thing that goes wrong in my life—from the biggest and most important to the smallest and most meaningless—and trace it back to some sort of shortcoming. We're talking about bursting into tears when my partner tells me I "failed" to load the dishwasher correctly, beating myself up when I “fail” to get the dog to sleep on my side of the bed, and regularly thinking about the 2-star rating an Uber driver gave me six years ago because I “failed” to impress him with my sparkling personality (though I did succeed in puking out his window at 2 a.m., so that one may be irrelevant).

In practice, this has meant sticking with things I know I’m good at and avoiding anything that might turn out as anything less than perfect. For most of my life, it’s worked out just fine (and motivated me to find any and every way to get out of playing high school sports, which was a definite bonus). But now that I have the freelance freedom to do whatever I want, I’ve come to the conclusion that it’s a pretty shitty way to live.

Plenty of qualified people have beaten the benefits of failure into our brains (“Only those who dare to fail greatly can ever achieve greatly,” says JFK; "Failure is another stepping stone to greatness,” says Oprah; “Never let the fear of striking out keep you from playing the game,” says, depending on who you ask, Babe Ruth or Hilary Duff in A Cinderella Story), but that doesn’t make the process any less scary.

What has helped me power through it, though, is the answer I got during a late-night anxiety spiral when I asked Google, “How can I stop being so fucking afraid of failure?”

My favorite 3 a.m. virtual therapist had a lot of advice to offer—like “recognize the cost of not trying” and “give yourself permission to be a beginner”—but there was one piece in particular that I’ve taken to heart: Do it scared.

I’ve gone to sleep every night for six months wishing to wake up and be magically cleansed of all of these mental blocks. But it doesn’t work that way. So here we are, during our waking hours, doing the damn thing scared. And if it doesn’t work out? The good news is that the worst failures tend to make for the best stories.

All of this was an extremely long-winded way of announcing the relaunch of this newsletter with a new vibe and a new name, inspired by my high school yearbook quote: “Life’s short. Might as well make it amusing.” At the time, I thought the words came straight from Queen Coco Chanel herself, but I now know it’s a Millennial-ified (read: bastardized) version of what she actually said, which feels so, so right. Because 15 years later, my failure to fact-check—and my confidence in taking some ridiculous, albeit accidental, creative liberties—will hopefully result in something you’re excited to see in your inbox.

The idea here is pretty simple: As I’ve discovered since high school, life is not only short, but it’s also really hard to fucking navigate. With this newsletter, I hope to make every part of that process as amusing as possible. Most posts won’t be quite as self-indulgent (or obnoxiously longgg and unfunny) as this one, but my hope is for this to feel like a regular update from your best friend—about beauty, wellness, mental health, love, work, family, and anything else the girlies are talking about—from someone who’s trying to figure out it all out in exactly the same way you are.

a·mus·ing (adjective)

/əˈmyo͞oziNG/

1. causing laughter and providing entertainment.

For now, the posts will be free, but come June (after I’ve hopefully given you enough reason to want to keep reading and proven that I can get my shit together to send out a newsletter every week) I’ll be switching to a paid subscription model in the hopes that I can spend more time doing this and less time writing SEO commerce stories.

Thanks for reading, and cheers to laughing in the face of self-doubt, failure, and whatever else life throws at you this week.

For your amusement: Laughing in the face of failure

From now on, each newsletter will end with a few things that amused me over the previous week—which is a succinct way of saying “a list of random shit that made me laugh, brought me joy, entertained me, relates to what we’re talking about, or just feels worth sharing”—and will hopefully do the same for you.

This week, it’s lol-worthy #epicfails. You’re welcome.

1. The time I cut my own bangs

@zoeweinerrr @zoeweinerrr ♬ Gorgeous - Taylor Swift

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Honestly they’re still not back to norma, and I still very much have regrets.

2. This girl’s “bearfoot” tattoo

@christifritzI made a HUGE mistake 😭

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I stumbled upon what I can only describe as “the darkest possible corner of the Internet” in the form of this couple, who have committed themselves to being barefoot at all times (like, they cut the soles out of $20,000 worth of shoes). One half of the couple was so excited about this chapter that she decided to commemorate it with a tattoo… except she spelled it wrong.

3. The woman falling off the stripper pole at the Super Bowl

@nikkimariedaliaAnyone else notice the dancer fall off the pole during Ushers Half time show during the SuperBowl 😟😳👀 #ohno #ohnonononoo #halftimeshow #superbowl #superbowlsunday #superbowl2024 #fyp #foryoupage #foryou #superbowl #usher #halftimeshow2024

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To be clear, she is still a WHOLE HELL OF A LOT BETTER at this than I was the one time I tried it:

zoeweinerrr

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