52+ Lessons from Writing for 52 Weeks Straight
Why hitting Hacker News front page won’t make you happy… and other musings on content creation
Today marks a major milestone in my creative journey. Every week for the past year, I’ve written and published a newsletter. At first, it was read by just 5 people (family and friends that I pestered to sign up), but today my newsletter, Avthar’s Weekly Wisdom, is read by hundreds of people from all over the world every week.
I’m a big believer in the power of reflection. So I looked back at all the writing, publishing and promotion I did over the past 52 weeks and set out to extract 52 lessons I learned from the experience. The result of my reflection is this essay, which contains 86 lessons I learned from writing and publishing weekly over the past year (34 more than planned!). They range from lessons about writing and being a creator, to things that my undertaking has taught me about myself and about life.
Treat this essay as a buffet: Skip around, read what you’re interested in and come back for seconds (and thirds!).
The lessons are grouped into the following categories:
Why Write?
On What to Write About
On Writing Well
On Creating Consistently
On Audience Building and Sharing Your Work
On What Writing Taught Me About Myself
On What Writing Taught Me About Life
Here are 7 some of my favorites to whet your appetite:
#11: Write for your children (and grandchildren) (From Why Write?)
#16: Write what you would like to read. (From On What to Write About)
#29: Deadlines inspire decisiveness. (From On Writing Well)
#41: Your brain is for having ideas, not holding them. (From On Creating Consistently)
#49: There’s a difference between why you write and why your audience will read. (From On Audience Building and Sharing Your Work)
#73: You do your best work when you don’t compete. (From On What Writing Taught Me About Myself)
#84: Criticism and praise are the same demon in different disguises. Pay no attention to either one. (From On What Writing Taught Me About Life)
I hope these 86 lessons about writing, creating and life help you live better, or at least, teach you something small.
PS: You can join me for the next 52 weeks of my journey to create and serve by subscribing to my weekly newsletter about self-mastery, entrepreneurship, health and happiness, where you’ll discover one thing that helps you change your life every week.
Why Write?
Writing is worthwhile for its own sake.
Like all of life’s finest pleasures, writing is an end in itself. The challenge of finding the right structure, sequencing and phrasing in order to translate feelings and thoughts into words on the page is extremely satisfying in its own right.
Writing is also immensely enjoyable. I had the most fun when I was writing stuff I was genuinely interested in.
Writing is an outlet for self-expression.
Writing consistently ensures that the pipes of expression remain unclogged and smooth-flowing.
Writing is a great way to make new friends (and reconnect with old ones).
I’ve been fortunate to meet many sincere folks during the past year. I want to thank my friends Vishnu, Rohun, Adam, Lev, Zakk, Jen, Jenny, Dokita, Charlie, Route2FI, Praveen, Salman, Joseph, Juan David, Danny, Dickie, and Shamay for all their help, feedback and encouragement. And shoutout to everyone else I met through Write of Passage!
Writing improves your thinking.
Writhing has helped me clarify what I think (e.g Everything is a Skill, The Bruce Lee Method of Learning).
Writing weekly helped me compress, crystalize and package lessons I’ve learned during my life (e.g The Internal Scorecard, The Founder Mentality).
The most rewarding writing was about topics (I thought) I already knew about (e.g Why you have your best ideas in the shower). After condensing all my mental frameworks in one place and connecting previously disparate ideas, I left with a deeper understanding of the topic than when I started.
Writing is cathartic.
Writing helped me reflect on my past, work through difficult times, and deal with difficult topics. (e.g Self Worth, Black Lives Matter, Purpose and Vision)
Writing helps avoid the illusion of knowing.
The illusion of knowing happens when you think you know a topic well, but when you sit down to explain it, you realise that you actually have gaps in understanding. Writing helps you spot these gaps in your logic and deepens your understanding.
Writing is the new resume.
Publish to democratize access to your learnings.
My writing journey started when I compiled my advice and tools for success for new students at my alma mater, United World College Costa Rica (the doc lives on at How to Succeed at Learning at UWC)
Writing helps scale your impact.
I wrote several articles about things I had individually explained to people I mentored or students who came to me for advice (e.g How to Network, Content is the New Resume, How to find Strengths, How to find your Dream Job).
Now they are resources that can help anyone in the world, even if I’ve never met them. And I think that’s amazing.
Write for your grandparents.
The thing I’m most proud of after a year of writing is getting a message from my grandmother back in South Africa telling me that she reads my articles every week and that she’s proud of me. (This was during the height of the COVID pandemic here in New York.) It made me realize that writing is truly worthwhile, even as a means sharing our thoughts with those close to us.
I’m grateful for the support and encouragement from my family, especially my parents, grandparents and uncles.
Write for your children (and grandchildren).
What would you want them to know about you, your life and how to live well?
Write for your past self.
This is both the easiest and most difficult sort of writing, It’s easy to think of ideas, it’s much more difficult to be honest and sincere (e.g What to read before starting a startup, which talks about resources I wish I read before starting my first startup, which failed.)
Write to reflect.
Write to help.
Write because you cannot help but write.
My answer to the question of “Why write?” is best summed up by an Alan Watts quote about why he gives public talks:
“So you might say, then, why do I talk?
You might ask the sky, Why are you blue?
The clouds, Why do you float around?
Birds, Why do you sing?”
On What to Write About
Write what you would like to read.
This is the easiest way to be consistent, find your voice, develop your brand and find content-audience-author fit.
In the words of Paul Graham: “How to make something people want? Make something you want”
The act of writing helps you find your voice.
Write the most helpful thing you can right now.
Write the most truthful thing you can right now.
Hemingway, whenever he was stuck in his writing, would tell himself to write one true thing. A true sentence. Then, he would write another. And another. (h/t “Live Your Truth” by Kamal Ravikant).
What are the things you can’t not write? Write that.
Write what you feel absolutely compelled to write about, not what you think you should.
You don’t have to have all the answers.
It’s easier to write what you truly believe than it is to masquerade that you have all the answers.
Your exploration of the complexity of a problem is worthwhile enough. Your perspective is enough. That’s better than creating prescriptions that wriggle to fit all life situations and contexts.
Share things you like.
Writing isn’t always about conveying ideas. You can share books you’ve liked (e.g My 2021 Essential Reads), people you admire (e.g Josh Waitzkin, Bruce Lee), articles you’ve found useful (e.g startup advice)
Everyone values trusted recommendations.
Write so that even if no one reads it, it would have been worthwhile.
The best example of this is “Meditations” by Marcus Aurelius, which was Aurelius’ thoughts to himself, which he never intended for anyone else to read.
What feels obvious to you is often most insightful to others.
Of course you have worthwhile things to say. Just look at your life!
I struggled with having “writing-worthy” ideas. I overcame it by realizing that I’ve written and said things worth sharing in the past. (e.g talks, presentations, podcast appearances, work projects, conversations). All I needed to do was re-package these into writing form.
Conversations are a great source of inspiration for writing, and vice versa.
On Writing Well
Embrace empty space.
Start writing early, write what you can and then step back. Let your ideas swirl in your subconscious. Then come back to the page with renewed clarity and insight.
The more sleeps in a writing cycle, the better the final draft.
Deadlines inspire decisiveness.
I set weekly deadlines to publish on Sunday and hold myself to them
Looming deadlines help you decide what to cut and what to include. Time pressure forces you to take action and make decisions that you’d otherwise put off.
Make it easy for your reader to convince themselves to keep reading.
Make your writing easy to read. Even better, make it easy to skim. Make your most important points stand out. Make it easy to find what’s interesting, fast. Set scroll-stopping hooks. Don’t bury the lede.
I make generous use of space, images and typography differences to try to achieve this.
Write for a specific person first, then generalize if absolutely necessary.
It was easy for me to compile my advice to students at UWC. I had attended that international school and was familiar with the learning environment. I’m glad I didn’t try to write “How to Succeed in High School”, because there’s too many situational corner cases to get bogged down in.
Ironically, writing for a specific person generates principles which can translate to a wider audience. For instance, my essays on internal scorecard, growth mindset and learning tools all came out of that document aimed at high school students.
Reading writers you like helps you write better.
I went back and created a list of my favorite books to re-read so that I can absorb the good writing style, explanatory methods and vocabulary subconsciously just by being exposed to it.
Clear writing is clear thinking.
Difficult doesn’t mean good. Easy doesn’t mean bad.
Sometimes the topic which requires the least research and synthesis leads to the best writing.
Trouble usually comes from trying to do too much in one piece.
Trying to do too much in a single essay is the easiest way to never publish.
It’s okay to break things up and leave things for next week (I first learned this with my series on How to Find Your Strengths)
Sometimes the email length limit tells you this, other times it’s your girlfriend/editor.
Structure and constraints foster creativity.
I do my best writing when it's highly structured with headings, sub-headings and other sign-posts. This helps readers navigate the piece and find interesting things quickly.
I changed the structure of my newsletter after 29 weeks to be more constrained, which has helped me both publish consistently and deliver value to readers every week. I went from writing full essays on a single topic, to sharing something helpful about 4 constant topics: Self-mastery, Entrepreneurship, Health and Happiness. This new format gives readers a consistent brand promise about what they’ll get when they open the newsletter every week, but also helps me feature my longer essays under one of the topic headings.
Keep a cutting room floor.
At the end of my drafts, I keep a collection of good ideas which didn’t quite fit or make the cut for that essay. I return to this cutting room floor to find inspiration for future writing and newsletter editions.
On Creating Consistently
It shouldn’t feel like a chore.
If it’s not fun, you’re doing it wrong
You can always save things for next week.
You don’t have to write all you can every week. You don’t have to publish all you’ve written every week.
Strike while the iron is hot.
While you have inspiration to write on a topic, do it immediately. Otherwise, when inspiration leaves, you’ll never get to it. There’s at least a dozen unfinished essays sitting in my drafts that taught me this lesson.
Your brain is for having ideas, not holding them.
When you have an idea for something worth writing about, write it down immediately.
Capturing ideas and jotting down your thoughts (in a journal or note-taking app) helps you create a backlog of topics and kernels for interesting pieces. This helps you write from abundance, rather than scarcity (aka a blank page).
The key to consistency is to write about things you’re actually curious about and interested in.
If no one knew I was writing about this, what would I write?
Focus on consistency not intensity.
My goal is simple: Publish something every week.
It’s made writing and publishing like brushing my teeth.
Quality emerges from volume.
Some of my best essays were spur of the moment things when I was taken by inspiration.
My commitment to consistency and volume created the conditions for quality to emerge.
Accountability is the key to building a writing habit.
I feel accountable to my audience to publish something every week in my newsletter.
I also benefited from peer-based accountability groups, where a group of writers would work on our pieces at the same time or give feedback on each other's work. There was an expectation to show up and that helped me be consistent, especially early on in my journey.
Resistance is inevitable. You must fight to overcome it.
The book that helped me grapple with resistance was “The War of Art” by Steven Pressfield and one of his other books, “Nobody Wants to Read Your Sh*t”.
Imposter syndrome is part of the creative process.
“The big reason is that we're all impostors. You're not imagining that you're an impostor, it's likely that you are one. Everyone who is doing important work is working on something that might not work.” - Seth Godin
I highly recommend Seth Godin’s wonderful blog on “Imposter Syndrome” and his book “The Practice” by Seth Godin for more authentic advice for creators.
Talk to your readers. They will reinvigorate you to keep going.
On Audience Building and Sharing Your Work
There’s a difference between why you write and why your audience will read.
Understanding why you write helps you be consistent and authentic. Understanding why they read helps you earn their attention and present an opportunity to help.
Promotion doesn’t have to be sleazy. You can promote in an authentic way.
It’s just something you wrote. Not who you are.
Save your praise to combat negativity bias.
The dopamine hit from a positive review will always be short lived. It helps to collate your positive feedback so you can look back and see some of the impact your work has made.
Your brand will emerge from what you write, not the other way around.
Writing to gain subscribers might work in the short term, but after awhile you’ll get bored of being inauthentic and give up.
It’s not that writing to gain subs is wrong, it’s just ineffective for long term consistency.
Writing is half the battle, the other 90% is getting discovered.
Promotion becomes easier when you don’t expect every post to go viral.
Promotion becomes easier when you truly believe in what you’re selling.
“Writing mode” is different from “Promoting mode”.
Automating promotion and batch writing posts that promote your work reduces the friction between moving between the modes of writing and promoting.
I personally use Buffer and Hypefury to automate promotion on Twitter and LinkedIn.
Don’t be afraid to promote your old work.
I learned this from Tim Ferriss. You don’t always have to be a stream of new thoughts and ideas.
Being brave enough to say the same thing over and over again is how you become known for it.
Own your relationship with your readers
My email newsletter is a direct channel to my readers. I don’t have to rely on third party platforms and their algorithms.
Promote on public platforms. Publish on self-owned platforms.
I publish on my website and newsletter. I promote on Twitter, LinkedIn and TikTok.
Measure success outside the dashboard.
I learned this from readers who would tell me how much they enjoyed the newsletter when we spoke, but seldom liked, shared or commented on the letter.
It’s the impact that is meaningful to me, not the audience size, engagement rate or anything like that
On What Writing Taught Me About Myself
Hitting the front page of Hacker News won’t make you happy
PS. This was the article that hit #11 on HN: Why I don’t care what Elon Musk thinks anymore.
Hitting your subscriber count goal won’t make you happy
“If I get that, then I’ll be happy” is a lie
Basing your happiness on metrics (or other forms of external validation) leads to suffering.
In the beginning I cared way too much about going viral, gaining more subscribers, gaining more followers. I thought these measures would validate me as a smart person, a good writer or a successful person. The mental suffering caused by doing this made me change my mind. And thank God I did.
Creating causes you to grapple with existential questions.
Questions like “What’s my voice?” “What’s my niche?”, “Why do I write?”, “What’s the point of all this?”.
If you can overcome the fear and self-doubt behind these questions, you will find authenticity.
Publishing forces you to step into the arena.
You show up and say “I made this. It’s not for everyone, but it is for someone.”
After all it is the person in the arena that counts, not the arm-chair professors or critics on the sidelines.
“The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly”- Theodore Rooseveldt
Sharing your work forces you to confront insecurities.
Being in the arena revealed my insecurities. In order to keep publishing every week, I was forced to wrestle with questions like “Am I good enough?” and “Will anyone read this?” which led to important internal shifts and breakthroughs.
Being in the arena teaches you about the nature of the mind
You are most at peace when you don’t compare.
You do your best work when you don’t compete.
Your desires are shaped by your environment.
I realized that my desires are fickle and are controlled by my inputs.
If my friends on Twitter were building digital books for Gumroad or selling courses, I then took on those desires subconsciously.
The Five Chimps Theory is right. If you surround yourself with four people doing X, then soon you’ll be the fifth.
This can work in your favor when X aligns with the goal you’re trying to achieve, but in my case it was a distraction and led to me almost running other people’s races rather than pursuing my own path.
I saw things like this all the time at Princeton, where pre-med students would suddenly become enamoured with investment banking, or budding changemakers deciding to pursue management consulting, all because the people around them desired those things. I never thought I would fall for it, until I did.
Writing is another avenue to pursue mastery.
I’m grateful to have found another medium to express myself and develop mastery in. For most of my life, I was a STEM-focused student, but I had a secret love affair with writing based classes (History, English, Philosophy). I’m so grateful I took the leap to make writing a habit and cultivate it over the past year.
The paradox of creating as play and as service
There’s an inherent tension between writing for yourself and writing for others.
One one hand, writing is something I do for its own sake. If people benefit from my writing, that’s great, but that’s not why I’m doing it. On the other hand, my writing is a vehicle to serve humanity selflessly. It’s a means of creating leverage and helping people at scale.
I learned to accept these two truths simultaneously, despite them being logically contradictory.
On What Writing Taught Me About Life
Every week is a chance to serve, help and explore.
If you know your WHY, you’ll be less likely to fall into the trap of comparison.
You are not your f******g khakis.
You’re not your subscriber count, you’re not your follower count, you’re not your bank account balance, you’re not your portfolio returns...all that sh*t doesn't define you.
Doing challenging things develops your character.
Life is a series of explore-exploit cycles.
In writing, you cycle between exploring phases, where you go wide and diverse and exploiting phases, where you go narrow and specific.
The same cycle is a good description for your career, your relationships and your life at large.
Self-expression and selfless service are the most authentic modes of being.
Human attention has a negativity bias.
Unsubscribes hurt more than new subscribers feel good. Criticism hurts more than praise invigorates.
Criticism and praise are the same demon in different disguises. Pay no attention to either one.
Internal motives matter.
I felt more aligned when I stopped viewing my work as “building an audience/ brand” and started looking at it as a medium to give and serve, as well as improve my own thinking.
Compounding is magical
A lot can change in one year. I committed to publishing something every week and after a year I went from having zero online presence to having 52 newsletter editions, 34 blog posts, 39 podcast episodes, 21 youtube videos and hundreds of posts on Twitter, LinkedIn and Tiktok.
I’m grateful for finding these different mediums to express myself, help people and, most importantly, have fun.
To 52 more weeks of writing
I hope you enjoyed reading these 86 lessons about writing, creating and life as much as I enjoyed writing them.
Join me for the next 52 weeks of my journey to create and serve:
Subscribe to Avthar’s Weekly Wisdom, my weekly newsletter about self-mastery, entrepreneurship, health and happiness. You’ll discover one thing that helps you change your life every week.
I also host Learn with Avthar, the podcast that helps you become a learning machine. You can listen on your favorite podcast app or on Youtube.
For more of my work, see my Best of 2020 - it contains 20 of my best creations, like my most popular essays, the most clicked links in my newsletter, and most downloaded podcast episodes.
Lastly, per lesson 26 above, I’m interested to hear which lessons resonated with you, which you found insightful and even the ones you disagree with. You can connect with me on Twitter (@avthars), or leave a comment below.
