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.
Do you want to be a writer or a thinker? This reminds me of a concept David Perell wrote about comparing the New York vs San Francisco style. New York writers create prose, they write beautifully, think New Yorker style pieces. San Francisco writers on the other hand focus on insightful, contrarian ideas, simply explained. Think Paul Graham. My strength as a writer is definitely the latter.
I’m a thinking-first, non-fiction writer. Many writers I admire such as Derek Sivers and Seth Godin fall under the thinking-first, non-fiction category.
What matters is not how much you write, but how much you rewrite. The difference between the amateur writer and a serious writer is the amount of time spent rewriting.
Shakespeare is a rare example of a strong writer and a strong thinker. If you don’t understand how incredible he is at both, then you’re a beginner writer. One of VGR’s litmus tests for whether one has advanced writing skills is, “write an interesting and original and personal essay discussing why you like 4-5 of your favorite Shakespeare verses.”
There are two types of rewrites. Rewriting about the idea (including/excluding, clarifying, compressing) and then some about language (word choices, sentence structure). The first kind is thinker-rewrites and the second kind is writer-rewrites.
To become a better writer you need to know what type of writer you are. Not just write a lot, but rewrite a lot. And sensitize yourself to good writing by reading the great works.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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:
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 NY’s close proximity to Toronto was huge for me.
A few close friends planned on moving to New York. This would make the transition much easier.
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.
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.
Notes
[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.
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:
Make them want to click the article or video. For example, I’ll quote a passage that resonated from the article as a preview.
If I’m sharing resources or giving song recommendations. I’ll share at most the best three resources or songs.
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.
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:
In my original blog post, I wrote that gentrification is not inherently bad. In retrospect, that’s an ignorant statement to make especially since I’m the gentrifier. I’m not the one experiencing the negative effects of it.
In short, here’s the gentrification timeline:
Undesirable areas are populated with the city’s working class and marginalized people. They bring their own businesses, energy, and character to the neighbourhood.
Attracted by cheap rents, artists begin to move in and transform the area through businesses of their own, murals, installations, fashion, etc. The neighbourhood is becoming “hip”.
Young, upwardly mobile, professionals in high-paying industries like finance and tech are attracted to the area. They have high incomes and can pay premiums for their apartments. Rents increase. As rents increase, the original residents and the artists are priced out. The original businesses are replaced by chains and multinational corporations. The area begins to lose the character that made it attractive to begin with.
Back when I lived in San Francisco, if I was asked about my job with someone not in the tech industry such as a barber, gym trainer, or tour guide, I’d almost shamefully tell them I work in tech. I felt like it was a subtle way of saying, “Yeah I’m the reason you’re getting priced out.”
Gentrification negatively affects the city’s most vulnerable population. As they get pushed out, they get uprooted and lose the communities they spent generations building. They also have to commute farther and farther to get to work.
Demographics begin to shift. Many that get priced out are minority groups such as African Americans or Latin Americans. The gentrifiers usually from upper class, predominately white groups. The diversity within a neighbourhood decreases.
