on not disappointing myself

notes on how I'm evolving my writing from unconfident to agentic

My approach to writing has significantly evolved in the past six-ish months. I began this newsletter as a way to collect “old alchemy for a young century”. I saw myself as an amateur archaeologist, digging for nuggets of wisdom collected across time and space. Over time, though, the process of building on other’s thoughts started to feel disingenuous. It felt as though I was creating an illusion of understanding something.

I think it boiled down to confidence. Every sentence in an essay has gravity. The more sentences you dedicate to someone else’s thoughts, the more they pull readers away from the orbit of your own writing. I was willingly letting that happen because I lacked confidence in what I was saying and how I was saying it. I felt as though my thoughts and experiences weren’t important enough, interesting enough, to strangers on the internet. Ironically, feedback from readers was the opposite: all of them said they’d like to see more personal stories woven in.

I wrote in my essay about conviction that “self-doubt and a lack of conviction make more people abandon a vision than competition ever will”. This was doubly true in the case of writing here. I wasn’t entirely convinced that what I was writing was true to myself, and yet I was scared to be more vulnerable because I was seeing myself from outside in. I was writing for a nameless, faceless audience, and letting that dictate what I should and shouldn’t write.

However, intuition has a way of making itself known. I think high-performing people generally fall into this trap: we obsess about the external world while neglecting our internal world. I used to think I had to be rational and logical about how I approached most things. But in the past six months, I’ve come to acknowledge that my emotional and bodily reactions had far more truth in them than rational thought ever did. That said, once a systems thinker, always a systems thinker — I wanted to see if I really could write something that resonated both with myself and with my readers. So I went back to my archive and identified all the essays that

1. did really well (in terms of likes and comments as well as replies and questions from readers)

2. felt authentic to me (in the sense that it accurately reflected my thoughts and feelings and wasn’t hiding behind someone else’s ideas)

In the Venn diagram that emerged, I noticed there were essays that ticked both those boxes. Each of them felt like the truest story I could write. That authenticity coloured readers, too, and many of you wrote back telling me how you felt seen or wanted to understand more. That was good enough incentive to stop disappointing myself and act on my conviction.

Good writing is downstream of self-knowledge. I once wrote that writing “is the act of externalising thoughts and feelings that might otherwise remain tangled and hidden within the depths of my psyche.” The only way to get this right was to engage better with what was going on inside my head.

I began taking more time to explore each idea I had. To poke and prod and hold it up to the light to see if it was worth pursuing. I pushed myself to examine every sentence and choice of word, because ambiguity in writing is where weak thinking lies. Like any act of self-expression and love, writing is embarrassing. You have to grab hold of a floating thought and shape it until it makes sense. You have to admit your failings as a human being navigating the world for the first time. That reveals ignorance and vulnerability in thinking as nothing else can. This process sounds harsh, but the voice doing the questioning inside my head is always lovingly patient. Less jailer questioning prisoner, and more parent helping a curious child understand. In doing this, I found a well of thoughts and connections I previously hadn’t tapped into for my writing.

It’s still cripplingly hard to weave personal narratives into my essays. No one wants to admit their fears and failings, least of all someone who has been a poster child for academic excellence. But I do feel a lot freer now that I write what I feel like writing about, rather than should. It’s a much longer process, because now I first write to think and then write to publish. I continue to pay attention to the craft and quality of writing — no hiding, whether behind someone else’s ideas or strings of metaphors that read pretty but hold no water.

I still love watching my subscriber count tick upwards, slow as it may be, but what I put out there is no longer coloured by it. Kindred Spirits feels more like a channel for selfhood now, something to look back on in a few years to see how my perception and thinking evolved over time. I think that’s why now, when someone tells me to keep writing, it feels like a command to keep living.

Some recommendations

• Why I Write, Greil Marcus via The Yale Review [essay]

• The B Lane Swimmer, Holly Witteman [essay]

• Babel, R.F. Kuang [novel]

• Personal Renewal, John Gardner [speech transcript]

P.S. Kindred Spirits now has a new URL: readkindredspirits.com. I like to see this decision as a sign of my commitment to writing on here. It’s also easier to share, so please consider sprinkling it in all your conversations with friends and strangers 🩵