Dear reader: cringe as a signal of taste

The first of a series answering curiosities that readers send in

“I think I write okay. I know I really enjoy it. And I couldn't agree more with your views on writing with conviction. But I really struggle with overcoming this fear of sounding inauthentic, pretentious, or worst of all...cringey. Did you also feel this way when you first started writing? What helped you break past this? How do you deliberately build ‘authority’?”

Dear reader,

When I first started this newsletter, every email I sent made me want to curl up into a ball. I wrote them warmly, and made sure I did my research, and wrote them to feel less like emails and more like the beginnings of a conversation. It didn’t matter — every 'whoosh' of my email outbox was the sound of my dignity leaving my body. I was embarrassed by the nakedness of my effort, of coming across as a try-hard. It’s also evident in the topics I chose haphazardly, in the way I fluttered between writing styles to, ironically, maximise authenticity and minimise cringe. So yes, I’ve been there. I think no one will shoot me if I say every half-decent writer has should.

I say should, because I think a lot of the times, cringe is a signal of taste. It’s a visceral reaction, an instinctive oof that tells us there’s a gap between where we want to be and what we’re currently projecting. Some amount of cringe also comes from a subconscious desire to be liked, to be seen. The process of being seen is being vulnerable, and that feels uncomfortable.

Unfortunately or fortunately, the only way out is through. “Being a well-meaning phony,” Joshua Rothman suggested, “is key to our self-transformations”. The route from aspiration to reality is paved with stumbling, cringey efforts. It’s embarrassing to be in the process of being someone. You’re trying to be someone you’re not, which makes you a tryhard, but there’s no other way to start other than by trying hard.

The beginnings of writing—and of anything that lets you strengthen yourself—will always feel as though you are play-acting. I honestly think that’s okay, and it’s okay to be okay with others possibly thinking you’re cringe. Cringe is subjective: what resonates with you will resonate with some and not with others. Like Bob Dylan said,

I'd either drive people away or they'd come in closer to see what it was all about. There was no in between.

These groups are always in flux; as you keep writing and grow comfortable with your boundaries and how you want to push them, the people that make up the two groups will shift, switch parties, even leave. So it might not be worth optimising for, anyway.

For those same reasons, neither is authority. Fortunately or unfortunately, you can’t control if you’re perceived as an authority or not. Many people you’d consider aspirational “authority” figures today probably stumbled into it quite by accident while fiddling around with things they love. But I feel that to actively pursue authority is to open yourself up to sirens tempting you to play a very different game than one you set out to play. Or to get locked up in a little psychic prison, left to stare longingly at the intoxicatingly free meadows that stretch beyond the bars. So instead of focusing on anything that will eventually be tracings in the sand, it might be more fruitful to aim for “to the best of my ability” with every single piece of writing you produce. All else that should follow, will follow.

And then there’s the matter of authenticity. There’s a million things I can think of that could be driving your fear of sounding inauthentic. You may be worrying that your work doesn't accurately represent who you really are, or worse, that it reveals a self you don't recognise or like. You may be feeling the weight of societal expectations to be "original" and find a niche or brand for yourself. You might be questioning whether you have the right to speak about certain topics, or be pursuing the idea of perfect authenticity. Since I don’t know the root cause of your fear, I don’t want to make any off-the-mark suggestions.

But of this, I’m reasonably sure: authenticity is nebulous. Most people today are perceiving you through a screen, and will only ever see the one dimension you choose to project towards them. On top of that, sometimes we don't know what we think or feel until we see it manifested in something we've made. So as long as we’re not forcing a fit into a form we don’t want to be in, I think we’ll be okay.

The most interesting writing often comes from that uncomfortable place where we're not quite sure if we're brilliant or ridiculous. So leap into that pool of cringe and splash around a bit. You might be surprised at what you make over time.

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Dear Reader is a new section of Kindred Spirits that thinks through questions submitted by readers about living agentic and meaningful lives. More than an advice column (because who can claim to be an expert in living life?), think of it as a conversation prompted by a curiosity. If you have questions for Dear Reader, you can ask them here :)