The imperfect man's guide to perfectionism

Breaking the loop of starting and abandoning a gazillion projects

The perfectionist has two problems: The first is starting and the second is stopping.

Perfectionism has nothing to do with being perfect. Wikipedia defines perfectionism as “a broad personality trait characterized by a person's concern with striving for flawlessness and perfection.” The striving is the operative word here because it describes what it feels like to be a perfectionist. Their idea of perfection is defined by standards that are impossible to achieve and they spend most of their time being as critical of others as they do of their own work. Nothing is good enough, it’s always possible to do just a little better, and time is always running out.

If you had to imagine a perfectionist character, it would be Fletcher, the demanding music teacher from Whiplash or Neiman, his self-critical drummer protege. Or maybe it’s Carmen Berzatto from The Bear for whom every dish stops at “almost perfect.”

Inside you there are two wolves

A real-life perfectionist was director Stanley Kubrick, who forced Shelley Duvall to do 127 takes of a single scene in The Shining, an experience that she characterized as “almost unbearable.” He also threw a camera from the top of a building – six times – to get the perfect shot of a falling man’s POV (the camera survived).

I keep talking about it in the third person, but I’m really talking about me. As someone who has struggled with perfectionism, most projects I picked up went through a predictable cycle of procrastination, obsession, and abandonment. I don’t want to remain stuck in this loop. So I want to take a closer look at it.

---

The perfectionist cycle

Any project I committed to led to two problems. The first problem was figuring out the perfect launch.

• What project should I commit to?

• What process should I follow? What is the optimal way to structure this project so that I can stick with it for a long time?

• How will this look three years down the line? Five years down the line?

• What if I get stuck in something I don't really want to continue?

• Do I want this to be my legacy?

• What if I build a large audience and then change my mind? And so on.

The bar was so high for starting any project that the burden of an uncertain future was compressed and carried by the present moment. It’s impossible to chart what a venture will become five years from now! Thinking through things in this manner was just a sophisticated form of procrastination, fueled by the illusion that I could solve all the problems of the future before they actually arise.

The second problem was in forgetting to apply the brakes. The projects that I started despite the unrealistic expectations I imposed on the act of starting had something in common – I had a clear task I could act on right away, a small doable chunk of work that was not a brick in a larger edifice but merely work for its own sake. Essays, short stories, and poems composed with levity in the lightness of the moment, failed a large majority of the time. But once in a while it led to something great.

Then instead of taking a pause and soaking in the moment, the inevitable next question was: "How can I do more of this? How can I sustain this?" Continuing the momentum and making the most of that perishable inspiration became an all-consuming priority and I start constructing a process around what was a spontaneous and enjoyable task. Schedules were planned, discipline became important, optimizing the process was now a concern, and what was once a creative endeavor became an industrial activity. The overhead associated with the task started to grind against the relentless pace of the work, and at some point, I snapped, going “I was never meant to do this in the first place. This is an unsustainable disaster.”

Psychotherapist Carl Jung popularized an idea called Enantiodroma – that every phenomenon contains the seed of its opposite, and with the passage of time, the unconscious opposite will emerge. For example, an increasingly conservative society could breed frustration against its stifled environment and lead to a liberal backlash. The periodic booms and busts in the stock market are also enantiodromic. Around 1999, the dot-com mania led to hype around Internet stocks. Thousands of people piled in, buying into any company that had a dot-com in its name, inflating prices and leading to a stock market bubble. Predictably, most of these companies were duds, and the bubble burst – which led to a loss of interest in the stock market again.

My oscillation between constant procrastination and reckless overworking feel like a case of enantiodrama too. Every time I delayed starting a project, I felt the pressure to "make it work" when I eventually did. I attempted to do this by overworking, which led to exhaustion and burnout, and then I hesitated committing to the next project.

---

The Five Slices Experiment

Recently, I started a newsletter called Five Slices which curates five interesting stories in every issue. I send out three emails a week and there's no pressure to stick to any particular niche or topic – it's an exercise to curate and share the things that I find interesting. While it's too early to tell, I feel that Five Slices is a much more relaxing and sustainable undertaking compared to my earlier projects. I couldn’t resist reverse-engineering what it was about Five Slices that made it a more fun activity compared to my usual "serious" writing. Could I understand what was happening here and make better decisions about the projects I committed to?

Five Slices wasn't started with the intent of succeeding at anything. The bar was very low but more importantly, there was no pressure on the outcome. The idea was to focus on what I found interesting. When I found myself deviating from this and trying to second-guess what my audience would find interesting, I dialed back and intentionally took more risks, sharing content that might not work. Surprisingly, people seemed to enjoy this content even more.

But another purpose of Five Slices was to act as a distribution channel for a more refined, technical newsletter that I would start later – the topic for this newsletter is not decided. I was deciding between business storytelling, indepth analysis of technical topics like AI, and a bunch of other options. I wrote a few sample articles as well. The more I thought about it, the more anxious I got about this "main project" that I was procrastinating on. Part of me wanted to just pick a niche and roll with it, but I could sense that this balancing act between Five Slices and a longform newsletter I wasn't seriously invested in would drain my energy.

---

Three principles to commit intentionally

While having tea with my friend Noble, he asked me a throwaway question that got me thinking.

“If you had to talk for an hour about any topic without preparation, what would you pick?”

I thought about it for a minute or two and said “Harry Potter.” I later thought that Quentin Tarantino would be a better choice – I've watched all of his movies at least once, and read through his interviews. Even with 10 minutes for a brief biography and 5 minutes on each of his movies, I could breeze through an hour easily.

Trivia for cinephiles: Which 3 movies would Tarantino bring to a deserted island?

Yet I had never considered starting a newsletter discussing the merits of Harry Potter or Quentin Tarantino – for good reason. I was far from an expert on these subjects and was afraid of coming across as a hack (writing about writing is something I'm wary of because it's the sort of self-indulgent exercise that easily morphs into an addictive outlet) but these topics also seemed too “trivial.” Who would be as obsessed about Tarantino as I was? Did I have content to write a 100 issues on the topic? Could I do this for another five years without getting bored? How would I monetize this down the line? How would I resist the urge to monetize this? Should I resist it? Within minutes, my pet obsession had transformed into a project proposal that was outcome-driven, and without a five-year plan, even a five minute throwaway post felt like a trivial pursuit.

But my friend's question connected with something I came across earlier – “Good writing is energy transfer, not information transfer.” When you write about something that you really care about, you want to transmit what you are feeling about the subject instead of trying to look smart. I could spend a week researching the most hype-driven topic in the news like "Deepseek is a threat to America's AI dominance" and write a good piece explaining what it’s all about. While the post could attract eyeballs because of the novelty of the topic, I doubt it'll breed as much loyalty as a passionate rant on a topic that I really care about. The authenticity in writing shows when the writing is unforced.

Principle 1: The good writer’s commodity is confidence, not content. Write about what you really care about.

There’s a concept called "The Lindy Effect" that emphasizes the staying power of long-lived items. If something has been around for a long time, the chances that it’ll stay for longer are higher. Shakespeare and Aristotle have been around for centuries, and they'll probably remain classics for a long time as opposed to the bestseller that was doing the rounds on BookTok the last week. This isn't about the relative merit of these works. Ideas, works, and companies that survive a long time have competitive moats that might help them survive even longer.

My hypothesis is that the Lindy Effect doesn't apply just to ideas or companies but also to people's interests. One strategy to set a personal direction is to think about what interested you in your childhood. If you've been interested in cars since you were 8 and in AI only for the last 8 months, you'll probably be interested in cars for a much longer time. If your interest in design emerged from your interest in drawing, your interest in art is a more stable foundation for other interests compared to design.

This ties in with the previous principle to write what you know about. If you have journals, photographs, letters, childhood collections, or even friends who have known you for a very long time, spend some time figuring out what you have always been naturally interested in.

Principle 2: If you've been interested in something for a long time, the chances that you'll continue to be interested in it are high. If you want to sustain a writing habit, writing about this interest is a good idea.

Five Slices has also been sustainable (so far) because it's based on a system instead of a topic. This works great for a certain kind of mind. I find it very hard to retain focus on any one particular niche and frequently wander into rabbitholes on the internet. When I stumble across topics that I find interesting, I’m not really thinking about whether they can be content fodder or belong to a niche that is monetizable five years from now – but it seems like such a shame to let all of that fascinating stuff go to waste. Some of the best conversations that I’ve had with my friends were about the most random topics, so I started Five Slices as a bid to share such things with a wider audience. The schedule of five stories in a post, three times a week, gave my randomness some structure without imposing a rigid restriction on what had to go into those stories.

The important thing with any project for me is to maintain momentum and keep it sustainable. Let momentum drop too much and it stops. Increase it too much and I burn out, criticizing myself for attempting something so irrational in the first place. If I can create a sustainable structure for long-form articles in the same way I created one for Five Slices, I think that I can keep it going without burning out. If I can keep it going just long enough until I start to see emergent patterns, I can figure out a sweet spot – the intersection between what I like to write and what people would look forward to reading. Then I can double down on that.

The risk is in waiting until I figure out this “perfect structure.” Hence:

Principle 3: Systems incentivize behavior. Create the system that lets you take the minimum action necessary to build momentum. Trust that you can change the system if you need to and give yourself permission to do so.

This is something I am writing for myself, to come back to when I have trouble remembering the habits that work for me. I am a creature of my environment after all, and designing one that works for me is my goal at the moment. These principles might not work for a different kind of personality, say, one who creates content incessantly without reflecting on branding and category creation, or somebody who never worries about long-term plans and lives in the moment. But for a procrastinating-perfectionist type, I think these might be of some use.

---

If you read till the end, consider subscribing (for free) to read my future articles.

If you prefer something lighter, I write Five Slices where I curate five interesting stories and ideas three times a week. You can check it out here and subscribe.