#16 Reflections and Resolutions

New Year's resolutions. Plus: everything I've learned in 2020 about writing, tweeting, working, thinking, and managing my psychology. And an awful poem about eggs.

Welcome readers old and new. This is one of Thomas Hollands’ notes in his search for ideas which are surprisingly general, or generally surprising. You can find all past issues here.

Another one

Happy New Year. At the risk of becoming a shill for semi-sovereign island communities, here’s another picture from Madeira:

Ensconced in our separate digital echo-chambers, Westerners share few rituals these days. But New Year’s resolutions are a unifying force: most people, regardless of political preference, sexual orientation, or economic class, still make them. To kick off the new year of this newsletter, I’m sharing mine with you.

I’m also sharing a brain dump of things I’ve learned about writing, tweeting, working, thinking, and managing my psychology. If you like, you can think of it as a late Christmas gift.

Everything that follows is one big, bulleted, note to myself. None of it is advice. But you might find some of it interesting or useful anyway.


Last year I only had one resolution: to make more stuff. I succeeded in doing this.

This year, I’m being more ambitious. I’ve got five resolutions:

  1. Listen to the entire Story of Civilisation

    For a while I've thought it would be beneficial to tune out the news for a whole year, replacing all doomscrolling with reading history. Then, when you come back to the news, you have a grab bag of historical analogies to contextualise the daily outrage, instead of getting sucked into it.

    I've finally decided to take my own advice, via the the wonderful medium of the history audiobook. I've chosen audiobooks for two reasons: I often give up on nonfiction books halfway through, whereas with an audiobook I can just listen to the boring bit while I do chores. And by keeping to one medium, I'm hoping this will be an easier habit to stick to.

    I will miss podcasts. I'm hoping that when I resume listening to them next year, there will be a plethora of aural pleasure waiting for me, and my ears will be refreshed and wiser from their break.

    I've started with The Story of Civilisation, by Will and Ariel Durant. It's an eleven volume epic that puts Proust to shame. Volume 1 alone is 50 hours of listening. I'm about 7 hours in, and so far, so great.

    I've already noticed one difference to podcasts: audiobooks are harder to start. With podcasts I'm happy zoning in and out, but I want to give audiobooks the direct attention they deserve. We'll see how this evolves over the coming months.

  2. I'm only going to read books I really want to read

    I would like to improve both the precision and fluidity of my writing, which means I need to read writing that is both precise and fluid. Most writing is neither.

    To achieve this, I'm going to stop reading more books. Growing up, I was rewarded for being precocious and relatively well-read, and I've been a completist about finishing books ever since. Now I want to reward myself not for how many books I've read, but for how long I spend contemplating what I've read. Quality over quantity.

  3. Learn how to drive

    I've had the good fortune to live in walkable cities for most of my adult life. This is about to change. I thought I might be a member of the first generation to not have to learn how to parallel park, but unfortunately, level-5 autonomy hasn’t arrived soon enough. To stop my girlfriend from chauffeuring me around, and to persuade her parents I'm a Real Man, I'll finally get a driver's license.

  4. Have written at least 50 newsletter issues by 2022

    I'm not going to force myself to publish a newsletter issue every week. But I will try and force myself to write down my thinking every day. Hopefully, the seeds of these thoughts will bear dozens more fruit by this time next year.

  5. Be more ambitious

    When I was in school, the most common complaint I received was that I was too arrogant. At the time, I arrogantly thought this was because everyone was threatened by how much smarter I was than them. But really it was because they were annoyed by how much I rubbed their noses in their own mistakes; by how I tried to do battle on every hill, no matter how tiny.

    My arrogance stemmed from insecurity. I didn't think I was particularly capable, but was validated when other people thought I was. So I took every opportunity to prove myself to others.

    Over time, I have noticed this insecurity wanes when I focus on goals much larger than myself. Instead of arguing over small differences, I put them aside to move forward.

    Over-ambition is often called arrogance. But I think the main source of my arrogance was that I wasn't ambitious enough. Perhaps being very ambitious requires delusion about your abilities in one specific domain, but I hope it will help me to become more humble in every other domain.

    I'm not yet sure how this ambition will manifest. But I'm pretty confident it'll have something to do with writing. So watch this space.

If you’ve made New Year’s resolutions I would love to hear them.

Leave a comment


These are all, without exception, from my own personal experience. Please take at least a few pinches of salt before reading.

The most important thing I learned this year:

I can do the things.

Until this year, it felt like I spent my entire life building up a store of potential, with more and more pressure to live up to it. But by simply starting to make things I like, I've managed to mostly release this pressure. I've learned a lot about what I'm really like, and what I really like, in the process. It's made me happier. And the inside of my head is now a much more pleasant place to live.


  • It's much better to have 100 interesting, interested people following you than 1000 NPCs or bots.

  • You cannot predict when or how you will go viral .

  • The best tweets are shot off fast, or iterated over 100 times. If you find yourself rewriting a tweet you're about to send, its probably not very good.

  • But that doesn't mean you shouldn't send it. you learn to tweet by tweeting.

  • Twitter is a resume for your daydreams and free-associations. And it works. It got me at least one job.

  • Most people do not think much about what they tweet. You should think of other people's tweets as idle chatter, not ordained gospel.

  • The Twittersphere is incomprehensibly large. And the kind and generous people will find you before the haters.

  • You get the audience you deserve.

  • Twitter is a global decentralised neural network and we're all training each other with likes and RTs.

  • Most tweeters are hyperoptimised for their audience, and probably didnt mean exactly what you think they mean.

  • It is easier to write a 280 character tweet than a 140 character tweet.

  • Its much easier to write notes to self and then tweet the best ones than to tweet into the void.

  • Having writers block when you open twitter is just like having stage-fright.


  • Write fast, bad, and wrong. Edit later.

  • There are three stages to writing: starting, writing the first draft, and rewriting. 40% of the difficulty is in starting. 55% of it is in rewriting. Actually writing the first draft is easy.

  • No idea is truly original. But many are almost-original.

  • You have many more almost-original ideas than you think.

  • All your almost-original ideas are at least partly based in your direct experience.

  • It is easier to write a 1000 word blog post than a 500 word blog post.

  • Most 1000 word blog posts should be 500 word blog posts.

  • The more you publish, the easier it becomes. But pretty much everything you publish you're fed up with at the time of publishing.

  • Copywriting has more in common with poetry than prose.

  • In prose the argument matters more than the audience. In copywriting the audience matters more than the argument.

  • You can probably write a piece of shit first draft in 10 minutes if you start right now. That piece of shit will contain several corn kernels of a good essay.

  • Write for one person at a time.

  • If you think attentively about your writing you probably have better taste than 90% of your readers. Even (especially!) if you think your writing is crap.

  • Readers don't know what you are trying to say. They only know what you say. And if what you say is good, then they'll think its good! Even if it's not as good as what you were trying to say.

  • The writing process is a random-forest algorithm: drafting is generating new trees, editing is pruning them.

  • It's easier to write when you're hungry than when you’re full.


  • Twitter is a phenomenal way to find mentors.

  • “When the student is ready the teacher will appear” is true.

  • You have to demonstrate your readiness by showing serious interest in the teacher, and having done something of value .

    In my case, I did this with a cold email to Vaughn Tan, backed up by my 'weird' twitter (his words), and a curiosity conversation with Paul Millerd, backed up by his generosity and willingness to take a chance on me.

  • Being “ready” is chiefly a mindset thing. You have to deprogram yourself of credentialism. You have to actually want to learn.

  • Good mentors are people who you are personally interested in for reasons that most people are not.

  • Mentors are useful because they're exist on a higher plane to you. You can imitate and emulate them, but unlike peers you're competitive with, they'll feel flattered or amused by it instead of threatened by it.

  • They're also useful because they've made similar mistakes to you in the past, and can help you internalise your learnings faster.

  • Like a ski guide taking you off-piste, good mentors push you before you think you're ready. They're better at evaluating your readiness than you are.

  • Having relatable mentors who have Done The Hard Thing makes it so much easier for you to Do The Hard Thing.


  • Working in an organisation where people expect less than you expect of yourself is a well-trodden path to mediocrity and unhappiness.

  • Since most organisations are optimised for their median hire, most organisations will expect less of you than you expect of yourself.

  • Unless you have a good mentor, no one can push you harder than you can push yourself.

  • Every time you force yourself to do something you hate, you become a person who is more tolerant of things they hate.

  • I now know over a dozen people who only spend an hour or two per day on their 'demanding' full-time job. I used to be one of them.

  • Big companies are like the Hotel California. You can check out any time you like, but you can never leave. (because you're too terrified of losing your status and paycheck).

  • Many (most?) hiring managers treat job interviews as an afterthought. Their full-time job takes up all their brainspace. They probably haven’t thought much about your CV or cover letter. They might not have even read it.

  • If your goal is to “get a real job” for a few years then work out “what you really want to do”, you can also just… work out what you really want to do straight away.

  • Instead of working in consulting for two years then leaving for a startup, you can just... leave for a startup.

  • You should only work with people who are 1) smart and 2) good.

    • in some circumstances you may employ people who are good but not smart

    • but under no circumstances work with people who are smart but not good

  • It is hard to underestimate the value of writing online. It's a portfolio of your interests and skills, a lead generation mechanism for future work, and can create friendships for life.

  • Cold emails are superpowers. With a direct, specific request in a few lines of text, you can get the attention of anyone with an internet connection.

  • Definite optimism created everything around me. Every company, every sports team, every work of literature, every cultural institution, was created by someone who thought the future could be better in some tangible, specific, way.

  • If you're indefinitely optimistic (I used to be), becoming definitely optimistic seems kinda impossible. But it’s like any skill. You can start small.


  • On Zoom, everyone is in an equally long-distance relationship.

  • It is very very hard to catch up with people if you don't have an activity around which to coalesce your chatter.

  • Going from chatting with someone on zoom to chatting with someone face to face is like going from black and white to 4K HD colour TV.

  • When I react badly to something it's always about me, and never about the thing.

  • When someone you haven't seen in a while expresses surprise about “how much you've changed”, they're probably thinking about themselves.

  • If you've changed, but you think your friends don't know or haven't noticed, it is psychologically very hard to arrange to catch up with them.

  • Journalling about your relationships is much more effective if you write down the good times as well as the bad. It is hard to write down the good times because you're too busy enjoying them to pause and reflect.

My Brain

  • The most important determinant of your happiness and your long term success (however you define those) is your psychology.

  • The biggest determinant of your psychology is your environment: your physical and digital locations and the people you surround yourself with.

  • If you unfollow everyone on instagram and then follow a bunch of fitness influencers you will work out more often with 100% certainty.

  • Intentionally designing your environment can lead you to do things you didn't even think were possible.

  • Gratitude journalling actually works.

  • Reading about other people's lives and having mentors is useful. But you will learn more useful things by reflecting on your own life than studying the lives of others.

What did you learn in 2020?

Leave a comment

End of newsletter. Do not read past this line.

SIL #4: Ode to the ovular ovum

Warning: terrible, terrible poetry follows. Do not read.


Full of life

Rounder than the Earth

More versatile than iPhones,

The proteinous pal for every palate,

A rich, mellow flavour to truly savour,

Makes more textures than your wildest conjectures,

Fertile source of emulsifier for each sauce you might require.

Smash them open: crunch. At breakfast or at lunch

Cadmium and white, even cads delight

In its richness, like melted butter.

Ovoids make my heart flutter:

None more than the small,

But mighty