Venkatesh Rao on Tips for Advanced Writers

A common piece of writing advice is show, don’t tell. As a writer looking to take the next step, I’ll often read pieces that show me that next level. But when it comes to improving, I almost rather be told how to get there.

A user on Quora asked about advice for advanced writers and Venkatesh Rao wrote a sharp answer brimming with gems. The answer in its entirety is worth reading. Here are a few notes:

September 24, 2022

Crazy Good Turns

Crazy Good Turns is a non-profit organization dedicated to generosity and gratitude. One of their initiatives is the $50 thank you award. Where you can send a thank you letter to anyone and they’ll give a 50$ gift card on your behalf with no cost to you.

I’ve written previously on showing our gratitude more often. It’s little effort on our end and it can mean everything to the person on the receiving end.

September 23, 2022

Game of Life

I was rummaging through my roommates card game when a handwritten note from the game designer fell out.

We’re Not Really Strangers Card GameWe’re Not Really Strangers Card Game

Profound instructions for both this card game and the game of life.

September 22, 2022

Everyone’s Interesting

When I talk with aspiring writers I’ll often hear them say, I’m not interesting” or I don’t have anything novel to say.”

Straight up, that’s not true.

Everyone’s interesting.

When you’re in your bubble, around people in the same circles and subcultures, then it may seem like you’re not interesting relative to those people.

But to an outsider that doesn’t understand that subculture you’re incredibly interesting. What’s obvious to you is not obvious to them.

As an extreme case, take the Hasidic Jewish population in New York. They have their own closed community with their own schools, hospital, police, etc. Even the signs in their neighbourhoods are written in Yiddish. To someone in that community, where they are surrounded by people that look and talk alike, I’m sure they think they aren’t interesting. But as an outsider, you can probably have a viral tiktok account documenting their everyday life.

Whether you’re into tech, art, or canned fish, whatever subculture you belong to, you are infinitetly interesting to any outsider. And that’s worth writing about.

September 21, 2022

Dark and Light Motivation

For most of my life, I thrived on dark motivation - motivation generated from insecurity, rejection, envy, hate, doubt, and other negative emotions. Accomplishments became my form of therapy. Where I would channel this negative energy in whatever goal I was pursuing. There’s a saying that chips on shoulders put chips in pockets and that was certainly true for me through high school and early university.

In other words, I transformed my pain and suffering into motivation. This served me well early on but has toxic side effects. I thought that I couldn’t be motivated unless I had bad shit happening to me. So then I would actively seek it out. If used too much, dark motivation can be all encompassing and lead to misery and depression.

But as I progressed along my personal journey, I started becoming more confident and comfortable in my own skin. My primary source of motivation came from a sense of purpose and self actualization rather than insecurity and rejection.

Despite learning to harness light motivation, I use both whenever necessary. At the gym for example, I’m intrinsically motivated to go to improve myself. But if I’m benchpressing a heavy weight and I need that extra motivation to get me through the set, I’ll dig deep and use dark motivation.

September 20, 2022

Credit Cards

I have a few friends that are deep in the credit card game. They talk about how they rarely pay for flights, book stays at luxury hotels, and skip the line at the TSA all through their credit card. I was skeptical at first, it sounded too good to be true.

Last week, I signed up for my first US credit card. I received a $250 bonus. On top of that, I get cash back on all purchases which can be redeemed for flights, hotels, experiences, etc. Additionally, I get trip cancellation insurance, purchase protection, car rental damage waiver, and so much more.

I remember being appalled when my friend told me about his $550 annual fee credit card. But then I read about the numerous benefits including a $900 sign up bonus, $300 yearly travel credits, lounge access, no foreign transaction fees, and even higher cashback on multiple categories. For someone like me that’s planning to travel a lot, the card pays for itself.

And understanding the basics of the credit card game wasn’t difficult. Spend an evening watching Daniel Braun’s YouTube channel (if you’re based in the US) and you can learn all you need to know about credit cards. Of course, you can dive deeper into the rabbithole, but one evening is all you need and it can mean the difference in saving plenty of money down the road.

September 19, 2022

Things I Enjoyed Recently (9.18.2022)

September 18, 2022

Creative Marketing

You’re a producer that makes beats, how do you go about promoting them? Maybe you’ll upload them to Soundcloud and Spotify, tell a few friends, and announce it on Instagram.

This is what most producers would do. But a young, up-and-coming producer named Mai is different. Mai went around Los Angeles asking random people to freestyle on his beats. The result? A fun, entertaining video that went viral with millions of views. It’s an ingenious way to promote himself.

Many artists are creative when making their art yet that creativity stops when it comes to marketing and promoting themselves. I’m guilty of this too. Derek Sivers has this idea that art doesn’t end at the edge of the canvas. That the creative process doesn’t stop when your piece is finished, but the act of communicating your art to world is an extension of your art. Mai is a great example of this.

September 17, 2022

Ask Why Three Times

Here’s a simple framework for clear thinking: ask why three times.

Whether it be a goal, a product decision, or a personal decision, I find this framework useful for getting to root causes or surfacing underlying motivations.

For example, one of my recent goals this summer is to learn interior design and apply that to my apartment.

Why? I want to live in a space that’s functional, beautiful, and inspiring.

Why? Sleeping combined with working from home means I’ll be spending nearly 2/3 of my time in New York in my apartment. Thus, it’s important for me to have a place that I want to be in and serves its purpose.

Why? Having a well designed apartment will improve my productivity, happiness, and well being.

September 16, 2022

Simmering Thoughts

A few weeks ago, I read Rohan Rajiv’s daily blog about My Shot” from Hamilton. I thought his analysis on the immigrant spirit of Alexander Hamilton as evident in the song was insightful. I never watched Hamilton but I’ve heard its iconic soundtrack before. But over time, this blog, and the song, simmered in my mind.

Sometimes I’ll read a piece and I won’t think much of it.

But over time the idea from that piece returns. It’ll come back again and again. Eventually I’ll write that idea down in the form of my own blog post.

I learned that ideas may not resonate instantly but they can resonate in the long run.

September 15, 2022

Macro Patient, Micro Speed

Before, I labeled long term thinking as good and short term thinking as bad. But this isn’t the case. Neither is inherently bad or good. It’s just that we have a natural tendency to think short term rather than long term. Short term thinking is common but long term thinking is rare.

Thus, be patient on a macro level. Then execute fast on the micro level.

For example, if one of my goals is to become a writer, that will take persistence and patience. In the interim, I can start to build an audience. Sticking to something long term produces compounding returns in the long run. Optimizing for speed gives results, encouragement, and validation, which is important when starting out.

September 14, 2022

Macro Focus, Micro Explore

Previously, I’ve thought of focus and exploration as opposite sides of the spectrum. I’m either focusing on a goal such as getting a full time job or I’m exploring a new hobby like writing or solo travelling.

However, I learned the two aren’t mutually exclusive. Over the years I’ve used an approach I call Macro Focus, Micro Explore. I’ll focus on a goal then I’ll explore within that goal. For example, recently one of my goals was to get a full time job. I focused completetly on this goal. I did what I knew worked such as applying to jobs and preparing for interviews. But I also experimented and tried out different approaches such as using different cold reachout strategies and using the briefcase technique.

That’s the spirit of Macro Focus, Micro Explore. Focus on a goal, and explore the bounds of that goal.

September 13, 2022

Why New York

Many people have asked me why I moved to New York? I jokingly answer, It’s New York.” Is there any other explanation needed? But on a more serious note, I had the freedom to move to any city in North America as a remote worker. Choosing which city to live in is one of the most important decisions of our lives. Hence, I put much thought into this decision.

It came down to Toronto, San Francisco, and New York. And I eventually chose the latter. Here’s why:

  1. Location. New York’s a short one hour and a half flight to Toronto. It’s also in the same timezone. I plan on traveling home often so NYs close proximity to Toronto was huge for me.
  2. A few close friends planned on moving to New York. This would make the transition much easier.
  3. Common advice is to live in the epicenter of the industry you’re in and New York’s the epicenter of many industries I care about such as technology, writing, and web3.
  4. I wrote about this extensively in a previous blog post but New Yorkers have exceptional taste. You can see this through the way people dress, the music shops and cafes play, and the books people read on the subway and in parks.
  5. There’s tonnes of media that advocate for New York. Whether it’s Frank Sinatra’s New York New York, Jay Z’s Empire State of Mind, or my personal favourite, E. B. White’s Here is New York. I couldn’t pass up on the chance to live in what’s arguably known as the center of the world.
September 12, 2022

Come From Away

This is my first time being in New York for 9/11 memorial day. I can’t imagine the chaos and the trauma the city went through on that fateful day. But even in that dark moment, a light shone brightly in a small town in Newfoundland on September 21st, 2001.

Recently, a friend and I watched our first Broadway musical called Come From Away. The play portrays the events at Gander, Newfoundland, a small town with a population of 9000 and home to previously one of the largest airports in the world, Gander International Airport [1]. During the attacks,the United States closed its airspace. Thousands of planes were diverted to alternate airports. Gander Internation Airport received the second most planes in Canada outside Halifax International Airport.

Overnight the population of the town doubled. Despite the lack of resources and accomodations, the people of Gander banded together, many of them opening their own homes to the stranded airline passengers.

The play itself, first workshopped in Toronto’s Sheridan College, did a beautiful job of portaying the heroes of Gander that welcomed strangers with open arms in a time of uncertaintly and fear.


[1] Gander Intertional Airport is the easternmost airport in North America. Because of its location, it served as a refueling stop for translatlantic flights back when planes had limited range.

September 11, 2022

Sending Recommendations

I have a few friends that will share videos, writing and music recommendations and I’ll consume all of it. These friends have good taste and are thoughtful in what they share. So I have high trust in their recommendations.

I sparingly share content with friends but when I do, I try to be just as thoughtful. Sending recommendations is like adding your stamp of approval to that content. Everything I share either builds that trust or hurts it. I like to think of myself as a curator of ideas, and so I take this reputation seriously. Here are a few tips I have for sharing with friends:

  1. Make them want to click the article or video. For example, I’ll quote a passage that resonated from the article as a preview.
  2. If I’m sharing resources or giving song recommendations. I’ll share at most the best three resources or songs.
September 10, 2022

What We Want

Many of us want to live a comfortable life.

Yet, a comfortable life void of purpose and belonging is empty.

And to live a life of purpose and belonging requires discomfort.

September 9, 2022

Lens in Which You View the World

It’s fascinating how people’s craft forms the lens in which they view the world. For my job, I’m learning about the construction industry. I didn’t know much about it beforehand. But as I’m learning more, I create analogies between general contractors and software companies.

Whenever I learn something new, I approach it from an engineering perspective because that’s my background.

I’ll talk with my writing friends or entrepreneur friends, and they also have a very different way of viewing things.

September 8, 2022

Bad Product Decisions

Many bad product decisions are made because someone kept quiet instead of speaking up.

Maybe the problem doesn’t make sense or maybe you have a different opinion.

It’s easy to put your head down and follow the group.

But speaking up now can potentially save lots of time, effort, and headaches down the road.

September 7, 2022

Stuff I Enjoyed Recently (9.6.2022)

September 6, 2022

Gentrification Revisited

Part of what I love about writing frequently is continually evolving my thoughts on previous subjects. A few months ago, I wrote about gentrification. These past few weeks I moved to Williamsburg, Brooklyn, the current poster boy for gentrification in New York. Here are a few updated thoughts on the subject:

September 5, 2022

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