On Writing Regrets

All writers from time to time will look back — or think back — to something they’ve written and feel some regret. Whether writing for many years as a hobby or professionally, there will likely be a progression in how one writes — there will be a maturing of outlook and opinions, changes in style, and improvements in skill. Reading back something you wrote many years ago can bring into focus these changes, which, on the one hand, can satisfactorily signal progress, but on the other hand, past written material can remind you of old aspects of yourself that you’d rather file away in a locked memory cabinet.

Writing regrets can be especially challenging to deal with when you don’t have control over whether your work remains published online. I’ve often struggled with this issue. I’ve been blogging for around eight years now and when I read some of the early stuff I wrote, I find myself cringing, and wishing I could explain myself to any readers coming across this work today.

It’s not that I regret having old content online because I think it showcases an ineptitude at writing (much of my older work seems fairly well-written). I’m not cringing at an amateurish way of writing, but more feeling a tinge of embarrassment about what I wrote and how I expressed myself. When I look back at some of my writing many years ago, I can’t help but notice how overly opinionated and confident I was (and about subjects I was quite ignorant about — and this ignorance revealed itself). I notice, too, that I would sometimes write in a way that was naïve, myopic, and careless. I can see clearly a lack of experience and empathy in certain opinions I was expressing, which is not to say I was necessarily being nasty — it’s more that I was leaving out necessary perspectives.

So how is it best to deal with writing regrets and the fact that some of your content — which you may now disagree with or want to alter — cannot be changed or deleted? Do you just have to live with the fact that readers may form judgements about you based on old beliefs and qualities that you have since questioned, revised, and improved upon? To address the latter question, there is no other option than to move past this concern. You do have to learn to accept that people you don’t know somewhere may construct an image of you that misaligns with the kind of thinker and writer that you are today.

In terms of the former issue, I think an attitude of acceptance applies as well. The desire to appear right, wise, informed, and measured can lead to writing regrets, which can nag at you, and which you can ignite every time you reflect back on something you wrote in the past. However, the intrusion of writing regret — and its persistence — usually comes from a lack of acceptance about one’s fallibility, blind spots, and missteps, all of which are human, normal, and understandable. Mistakes in writing, whether minor or large, are forgivable. They’re not a permanent stain on your reputation or character, even if others think that way.

Writing often expresses a particular slice of time in your, reflecting your general state of thinking and emotional intelligence. It can also reflect more specific states of mind like a particular mood, a creative block, or an outpouring of creativity and originality that seemingly came out of nowhere. The words that you write during these slices of time may be indelible, but whether this fosters regret or inspiration is a matter of choice. Past opinions and ways of communicating can lead to self-deprecation but they can equally provide motivation to improve. Moreover, I find the sloppier aspects of my past written work valuable because it adds to the overall picture of how I — in tandem with my writing — have changed course over the years. This retrospection should (hopefully) reveal a maturing of sorts.

Past writing is like a personal artefact, worth revisiting and examining, from time to time, as these artefacts add to the overall narrative of a life. Not all writing reflects something personal, but a lot of the time, it is evidence of what your mind was like at the time. This then can add a further detail into the story of how you, as a person, have developed. This would include any changes to your opinions, values, degree of nuance and thoughtfulness, and self-awareness (including awareness of your biases).

Feelings of regret are easier to stave off when writing is viewed in terms of a process, rather than a solid identity. What has been written belongs to a process, a person in flux, and not to snapshots of former selves, which are to be judged in isolation, or harshly compared to your current self. Humility is a healthy response to this process. Self-judgement, however, is misplaced.

With the broader perspective of writing over time, there is something meaningful about going from blunders to corrections — from many blunders to fewer — that is missing when you only write or publish what you consider to be flawless and free from criticism. Perfectionism can, on the one hand, sharpen one’s writing abilities — yet, on the other hand, it can stifle the creative process, which depends on trial and error, experimentation and novelty. In line with the view of writing as a process and not an identity, I try to think of each act of writing and each completed piece of writing as an active attempt of figuring something out, which happens both in the act of writing and then later in the act of reflecting on what I wrote.

Writing becomes a medium in which to solve a problem in my head, a way of divergently exploring questions like, What are my most authentic thoughts about this subject? How can I explore this subject in a way that is balanced and considerate? Am I being clear and helpful? Am I being careful enough and aware of my ignorance? Part of the meaning of writing, for me, comes from the pruning of thoughts and ideas that happens through the writing process. This endless pruning takes place in different contexts — in the moment-to-moment act of writing, after completion (which then involves further introspection), and through publication, which can lead to constructive feedback and fruitful discussions with others (in the best-case scenarios, of course).

So long as I try to write with this view of writing in mind, I am less attached to whether or not I am inarguably right and more interested in whether I have been able to coherently and fully articulate a personal struggle with an idea. This isn’t to say I don’t express strong opinions or don’t ever care about being right, but I would like to also see those shortcomings as part of a personal struggle, which I am trying to resolve, partly, through writing. I have fewer regrets about what I write or the way I write when I adopt this overarching attitude. This helps me avoid the mistaken sense that all creative output has to be immaculate in order to be valuable.

Originally published at https://www.samwoolfe.com on January 20, 2021.

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Sam Woolfe

I'm a freelance writer interested in philosophy, ethics, psychology, and mental health. Website: www.samwoolfe.com