How I Write: A Conversation With Myself




I’ve been listening to David Perell’s awesome podcast literally called “How I Write” and it’s made me realize I have a lot of things to say about writing. One of the most interesting things about the podcast is that there are not a lot of common “recipes” across the writers. Everyone has a different approach.  One person might write every single day at a set time while another doesn’t plan anything. One person might spend a lot more time thinking about maximizing attention while another obsesses mostly on the craft of writing.

This makes sense. If you do enough writing you realize that “writing advice” is not useful. You can get ideas from others on what blind spots you may have or a certain tactic you might want to copy but ultimately only one thing matters: what keeps you writing.

Which is what make’s David’s podcast so interesting. I listen to some things and think “ooh I want to try that” and others where I think “this person is insane!”

But it doesn’t matter what other people say about writing. The only thing that matters to me is that I am able to cultivate the conditions to stay interested in writing.

Here are a few reflections on my own writing journey and what has worked for me. Of course, don’t try this at home. Remix, experiment, and pay attention in your own way. Find your own unique relationship with writing. 

Writing Was Never Obvious

I loved writing but I was never paying attention

In high school I wrote this article for our yearbook about the “trend”  of driving a minivan while being a guy in high school. I found out that most of our mothers had discovered the much cooler crossover SUVs that were coming onto the market and foisted their far less cool minivans on us. I wrote about how this was a massive movement and about how a new generation of young people were making the minivan cool again. We had a picture of six of us standing in front of our vans, angled in the parking lot, standing with confidence. It delighted me.

In college, I wrote this satirical essay about my friend Martha and her participation in the safety patrol in high school. The whole thing cracked me up and I had the time of my life writing the article. 

After college I started a blog on tumblr and remembered a few pieces I spent a bit more time on, including  a movie review of one of the Twilight movies. It made me laugh and made a bunch of friends laugh. I loved that.

A couple years before I quit my job, I started doing more creative experiments, sharing things publicly, posting on Quora and then LinkedIn and Medium.

While I slowly became  more aware that writing was something I enjoyed, it never occurred to me that it was something that could be central to my work and life. 

It’s only obvious looking back.

Thus, writing has always been a positive thing for me

Writing saved me. It taught me that I could do something active in the world that felt good, sustainable and helped connect me to something deeper.. It helped me make sense of the world after I blew up my life at 32 years old. It has helped me make friends that support and encourage me and has helped me make money in ways that feel good. 

I’m forever grateful and don’t resonate with people that complain about writing as a struggle or people that constantly wonder how they can figure out how to write more. For years, writing has not been something I “should” do, it is something that must happen and does happen. It is something I get to do.

I could give half a damn about being called a “writer” or “author”

Other people have called me that. I don’t feel anything when I hear it. I did love the feeling of going to MIT and being able to tell people that in my twenties but as I’ve gotten older I really don’t care about labels or identities. 

Writing is fun and easy for me and I don’t take that for granted. For some reason I’m able to just sit at a keyboard and type and create magic in my life. It’s really that simple. I don’t need to test the gods by trying to make it my identity.

How It Happens: My Life Is Designed to Ensure Writing Emerges Naturally

I write, most days

I have had a mantra since 2018: “write, most days.” Back then I realized I liked writing and it was a reminder to do it. But it was also a reminder to not stress if I didn’t write for a couple days or even a couple weeks.

Now, I don’t need the reminder. Writing happens. I have a good relationship with writing and get excited to do it. Sometimes I get cranky and I realize that I just haven’t had enough focused time to sit, think, and write.

Most of the time, writing finds its way into the cracks of my life. I kept up my weekly newsletter while having a newborn and it never felt like I had to force the writing. When she would go down for a nap, I would find myself opening my laptop and writing. I had to get the ideas and thoughts out of my head. No matter how busy I was, I was able to produce something that felt good enough to share in my newsletter.

I am not a disciplined writer

Nor do I care about impressing anyone with my discipline. I don’t care about streaks or blocking off time each day to write. For almost seven years, I’ve written when I felt like it. Since I like writing and I’ve designed my life with a lot of slack, this has been easy. I would guess that for the last 6-7 years I’ve written about 5-10 hours a week on average with some weeks being about 30-40 hours (during peak book inspiration) and 0 other weeks.

I wrote most of my book in Taiwan in 2021. I didn’t do much else besides an intensive 3-month Chinese language course and a couple very small projects. This was me at the beginning, off to a rather slow start

In my first couple of years after quitting my job I spent a lot of time not working and simply wandering, reading, talking to people, and traveling. I was money poor but time rich and this meant that I was flooded with inspiration and things to write about. I had to write to process all the ideas floating in my head.

As I’ve gotten a little busier over the years and especially since having a kid, I’ve had to be more intentional with blocking off time for not writing and spending time wandering, taking long walks and bike rides, and having conversations with curious friends. When I have time to think I eventually get so excited that I have to write. 

While writing my book I would reach parts where I felt stuck and knew it was time to stop writing. Sometimes I stopped for a few days and sometimes a couple weeks. After a few days and some long walks or bike rides, the path forward for the book always appeared. I have done this so many times that I have a deep trust that I can almost always deliver on something, as long as I have the time and space to pay attention and let it emerge.

Shipping is better than not shipping

I’m not a perfectionist. I am comfortable with hitting send or publish without everything being perfect. This has probably frustrated some of the detail oriented accountants and lawyers that read my stuff and certainly pissed off former managers in my past life, but has helped me keep going and has been a superpower for sharing ideas on the internet, where every piece of writing is an invitation to others to come along for the ride.

Not seeing myself as a fancy writer or author person really helps with this.  Writing is just something I like to do. I am very good at sitting down and opening up a document and writing. And the more stuff I put into the world, the  easier it gets because it expands the conversation I’m having. 

Which gets to my philosophy of writing, that it is a beautiful conversation

Inspired by David Whyte’s idea of the “conversational nature of reality” I see all my writing as a three tiered conversation. It is a:

  1. Conversation with myself, exploring my edges;
  2. A conversation with the world, a way to transcend the surface-level sameness of modernity, and finally;
  3. A conversation with others, seeing what feels useful and interesting;

I write to make sense of the world but also to transcend it

My life is weird and my writing helps me feel grounded. This works well because my sensemaking is something other people are looking for too. The feedback I get sharpens my thinking and inspires more writing. It’s a beautiful virtuous cycle.

Writing has helped me to feel connected to myself and the world. It is an activity in which I can feel completely lost and completely grounded at the same time.

I take a rational assessment of my life sometimes and think “what the hell am I doing?!” Then I write and it starts to make sense.

I still don’t know what’s next for me and that’s exciting.

Because I can write my way through it.

Conversations with others is one of the biggest fuel sources for my writing and I stumbled into it by accident

A lot of my early writing would have been impossible without the hundreds of curiosity conversations I had with strangers from around the world. From 2017 to 2021 I had approximately 400 curiosity conversations with anyone who wanted to book a call on my calendar each Wednesday.

I originally set it up in defiance of the hustle wisdom of “monetizing your time” and not letting people access your calendar. It was an anti-strategy that became a strategy because I quickly realized how much I liked “finding the others” thinking about similar ideas. I would talk to people that would tell me things that were surprising (e.g. “I haven’t told my spouse any of this”) or that encouraged me to share my obvious-to-me thoughts with a bigger audience (“holy crap, I’ve never thought about that, you should write about that!”).

Over the years, I packaged these ideas into my writing, a course called Reinvent, my podcasts, and then ultimately, the appropriate vehicle for these ideas, a book. The book seemed obvious at the end of 2020 when I spent almost a year in a flurry of pandemic-related conversations about work with over 100 people who booked calls with me. That year was magical for me and it felt like I was in a deep connected flow with my own curiosity and the zeitgeist of how people were thinking about work.

When I finished the book it felt selfish not to share it and I excitedly published it as soon as possible. This might seem crazy to some people but was the same approach I have had with everything else along the way.

I wanted to keep the conversation going.

Mass market success bores me. I have a specific kind of reader in mind with my writing and I write for them. That is enough.

If you want to understand what I am doing with my writing you have to believe that mass market success, prestige, or financial success are not primary goals with my work.

I write mostly for myself as a way to make sense of the world. But I also write to be useful to others and for that to work, I have to honor what I’m really thinking. Phillip Lopate, writing on the art of the personal essay, argues that, “so often the plot of a personal essay, its drama, its suspense, consists in watching how far the essayist can drop past his or her psychic defenses toward deeper levels of honesty.”

The writing that inspires me is writing that pushes this threshold and it’s the kind of writing I like to do too.

I have tremendous care for my audience and I don’t want to bullshit them. I know my readers well because they are people like me and I have talked to hundreds of them. They are deeply curious about the world, don’t quite feel like they fit in the mainstream life path, and want to poke around the edges to see what other possibilities may exist. They don’t want surface level information. They want to go deep. I want to take them there.

This is a small but sizable number of people globally. It is enough. This also means that I am not writing for most people on the planet.

This confuses people. They’ll say, “well, what about group X? Don’t you think you are being insensitive to this group?” Or “You know, you could really reach a bigger audience if you talked about Y”

I don’t know what to say to these people. I love the people that read my stuff. I’m writing for them. It’s enough.

People don’t realize that if you are writing for a mass audience you are also hanging out with a mass audience.

That doesn’t sound fun.

I write for the hyper-curious weirdos.

Those are the people I like hanging out with.

Haters will hate but they (mostly) don’t care about me

I’ve received some criticism over the years but it’s still a 100:1 ratio favoring the people who have been pleasant and supportive. 

But haters do suck and they do make you feel terrible.

Eventually, most writers realize that haters don’t care about them. Haters won’t try to help you become a better writer or a better person. They’re usually projecting their own insecurities onto you, mind reading something you actually don’t believe or trying to fight you because you’ve awakened insecurities they’d rather not feel. 

I’ve received some useful criticism from 2-3 people over the years who also praised my writing and supported me directly prior to the criticism. These pieces of feedback were direct, clear and meant to help me. And they did! When you get these pieces of information from people that care, it’s a gift. But most people don’t care about your writing or your desire to get better. That’s a personal thing. 

Process: Turning Words Into Stuff Worth Reading

I like to dive into the deep end without knowing where I’ll end up

In my first week of training in consulting, I was put in a fake project team where we had to compile a bunch of information and develop a short presentation summarizing our findings. As we started looking over the materials we were given, there were two people on the team that were incredibly anxious. They kept saying that we should come up with an outline and map out the entire slide deck before we started diving into it. This seemed silly to me. We need to do a lot of analysis before we figure out what we have, right? 

I slowly gained more awareness that these people were top-down thinkers, people that need to know the destination before they head out. I’m the opposite, a bottom-up thinker, and I actually enjoy not knowing how things are going to end up before I start something.

Robert Caro, writing about his top-down approach in Working, said “I can’t start writing a book until I’ve thought it through and can see it whole in my mind. So before I start writing, I boil the book down to three paragraphs, or two, or one—that’s when it comes into view.”

This sounds terrible to me!

I like to write, write, and write some more, and then notice what I have. Brandon Sanderson calls this “discovery writing.” I had no idea how The Pathless Path would be structured. But every couple of months of writing I would pause and spend an hour reorganizing the chapters. That would feel good enough and the final finished product became about 10% less blurry. That was good enough.

It wasn’t until the final weeks that it occurred to me to split the entire book into two parts, the pathless path, and the default path. As soon as I came up with that, I could smell the finish line. It was exciting. But I couldn’t have come up with that if I had been tied to a strict structure.

Some people hate this approach but I find for me it leads to better writing. I am able to stay looser and more open to inspiration as I write. 

I typically write and edit at the same time. Most of my writing is re-writing.

Some people separate writing and editing. I tend to write and rewrite at the same time. I just rewrote this sentence a few times but have a bunch of things lower on the page I plan on writing for the first time. Sometimes I get sucked down rabbit holes and do a bunch of research and that’s all I’ll do for a day. Other days I spend the whole day rewriting one paragraph before I give up. Other times I just write and it flows out of me and I’ll come back to it the next day to rewrite. Very rarely, I write something I’m happy with the first time.

Most of my book writing was re-writing things I had written before but far, far better than the original. This Quora post from Venkatesh Rao nails it in terms of the value of rewriting:

The HUGE difference between everyday writing that everybody does and serious writing is the proportion that is re-writing. I’d estimate that for non-writers, rewriting accounts for maybe 10-20% of their writing.

For serious writers, it accounts for anywhere between 50-90% depending on how critical the particular piece is. This Quora answer is not very critical for me, so I’d say it’ll hit 50% by the time I am done. There are single paragraphs in my book though that took 5 minutes to write down initially, and then cost me hours to whip into shape, so that’s like 99% rewriting.

My sense is that the value of rewriting compounds over time. Now, I know if I have a solid idea and am excited about it, I am fairly confident that if I keep tweaking and rewriting over a number of days, I’lll get to something worth sharing. My biggest “trick” is to sleep on something. It’s funny how the next day you are always embarrassed by what you wrote the day before.

I read my writing out loud to myself, mumbling, while editing

I am obsessed with how things flow. I tend to read mumble the words out loud to myself while I’m typing them. I’m literally doing it right now. Before I finished my book I downloaded several versions to kindle and would read the words out loud to myself while reading on my bed. My wife had to close the door because it was quite annoying. I did this 5-7 times in a row over a number of days, highlighting passages I wanted to rewrite. If I find that things don’t flow easily out of my mouth or are hard to say, I change it. I like things to be simple and clear. I’m not writing for PhDs, I’m writing for people like me. I want things to sound as if they were having a conversation with me.

When I read my audiobook, I was surprised at how smooth it was to read. There were only 5-10 parts where I had to change up how I said things while recording.

I think this has helped my work resonate with a bigger audience. People like simple and clear. And like they are talking to a friend.

I am a very very independent writer. Potentially a blind spot?

I don’t really ask for any feedback. I rarely send my stuff to other people before I post it. I have asked for thoughts on less than five blog posts and newsletters in the last seven years. I get a lot more out of people’s questions. That’s my biggest source of inspiration. Sometimes I’ll post outlines of essays I’m working on and ask on Twitter, “what else should I write about?”

For my book, I got far less feedback than most people do. I worked with two editors and got five people’s opinions on the final version before shipping the book. I think asking for too much feedback is often a mistake. As a writer you need to trust your own taste.

I am also probably a bit overconfident with my writing. But I’ve done a lot of it and I know the kind of stuff I want to share.

When I thought about selling my book to Penguin I couldn’t imagine working with a team of editors pushing me to change things I didn’t want to change. 

It’s not worth it. Writing is a pathway to a beautiful life for me and it’s already working. Sacrificing this thing for a larger audience, more money, prestige, or anything like that doesn’t compute in my brain.

I could probably use more help too. I’d love to find a great editor that could work closely with me over a number of years. It sounds cool.

For now, I have fun going it alone.

How I Keep Going: Taste & Other Motivators

Coming up with things to write about is not hard (anymore)

I generate five new ideas of things to write about each day. Maybe more. I think about writing and do so much writing that I see ideas everywhere. I got the idea of this essay while listening to David’s podcast. I thought, I love these questions, what if I just interviewed myself.

I build my life around curious people and interesting ideas. I read books other people don’t pay attention to. I follow writers that aren’t well known. I filter my X feed aggressively, muting and blocking people that want to fight, take people out of context or share outrage. I rarely watch TV. In the flow of my life I talk to inspiring, optimistic and curious people.

I’ve always been trying to create the conditions to be around curious people and in the flow of a bigger conversation of ideas. For several years in my twenties, I ran a facebook group called Media Feast where 60-80 people shared their favorite longform essays. It was great but it was mostly digital. Most of my time was still spent around people that put their career and work above ideas and being creative.

After quitting I started slowly shifting my life in a new direction and my creative output dramatically increased. The real magic of writing about ideas is that the more things you write about, the more things you want to write about. Now, the conditions are ideal. 

My entire journey has really been about getting the conditions right. For me, it’s the whole game.

I like helping other people. It makes me feel useful

Twitter was a big unlock for me. It helped me to turn a lot of half baked thoughts in my head into something slightly more polished. I could then see what other people thought. If something got a lot of interest from other curious people, I knew I was onto something. If people asked follow-up questions even better.

It is a way to have rapid-fire conversations with the most curious people from around the world.

The thing that makes this a generative and positive use of time is that I actually like being useful. When people have questions, I get excited by trying to answer it and helping them. Other people get frustrated by social media because they rather build a business and make money. I actually just love being in the flow of ideas and sometimes being useful.

Throughout my writing journey I’ve written a lot of stuff that details how I do various things or how I approach my life generally. When people say it helps them it makes me happy. That’s enough for me to want to keep going.

Praise and attention is cool but for me, helping one other person with something is a far bigger motivator.

And if I can build a following and find people that might enjoy my work along the way? Even better.

I am competitive and writing is a great way to compete because you can do it in solitude

I read a book last year. It is a best seller and from a very famous person who has several books. The book was tangentially about themes that I write about.

I thought it sucked. It felt lazy, lacked personal perspectives, and was full of stories of random people and research studies that felt like they were dropped in by ChatGPT2  at the last minute. It’s the worst of what traditional publishers do to books. To me, anyway.

I like to sit with that frustration and see how I can use it. How can I do better? Write with more curiosity and vulnerability? Not bullshit my readers? Write the books and words that I want to see in the world?

It’s fun to compete in this way because you can compete secretly and anonymously. This person will never know I exist. But we’re in a fight and in my mind, they are losing.

I channel frustration through my writing

While I find writing fun and am generally writing around a positive and optimistic vision I have for work and life, sometimes my writing is driven by frustration. I see a piece of writing, or people praising a piece of writing that I think is objectively bad and I want to scream.

How could people think this is a good idea!?

Many people have feelings like this and I wish they knew what I knew: that this is simply an invitation to explore your own curiosity and try to do better.

Often, I find that I can’t actually debunk the things that frustrate me or come up with a better idea. It’s often humbling.

But sometimes, it does lead me somewhere.

I was sick and tired of reading career pages that lie to people, telling them, “You can do the most meaningful work of your life here.” It’s bullshit and everyone knows it.

It led me to go deeper and spend years thinking through what we really want from work.

That led to The Pathless Path. People seem to like my take and that’s pretty cool.

Writing Is Great And More People Should Do It…Yes, Even You

In sixth grade I was bored as hell in math class and would finish the work in a few minutes. After a couple months they pulled me out of class and let me work on anything I wanted. I decided I would do a report on the NBA’s 50th anniversary. I already had a massive book on the history of the NBA and funny enough when I think about the eight years I spent in that school, this is the one thing that stands out.

We live in a crazy time. We have the most educated global citizens in the history of the world and the vast majority of people hate writing or don’t think they can do it.

Schools are set up to turn people into people that hate writing. They teach you that you don’t get to pick the topics, that you have to follow the rules, and that most of writing is about arguing two sides of an issue. It’s insane.

Maybe this was just a way to control people. To make sure that people didn’t think they would ever be part of a special part of society that got to share ideas in  newspapers or books? I’m not sure.

But it doesn’t matter.

The internet has lowered the marginal cost of sharing ideas to zero.

I am biased. Writing on the internet has changed my life. But even in the early days when I had no followers, it was just as magical. 

Forcing myself to sit down with my thoughts and try to untangle them has helped me understand what I wanted out of life and slowly, take action towards achieving it. 

I am so glad I found writing and I hope you give it a chance too.

This was how I write.