How I Write.

A detailed look at the process behind these posts.

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Over the weekend, I passed 10,000 active subscribers (and 11,200 all-time subscribers, adios to those who unsubscribed), which is, to me at least, a pretty cool milestone.

Today, I want to write about writing itself. I've had several people reach out asking about my writing process (especially you, Charlie Davidmann). Since I crossed the 10,000 mark, it seemed like a good occasion to share my process.

Keep in mind, this is how I write. This doesn't have to be, and probably shouldn't be, how you write. My method has been largely molded by the environment I was living in when I began taking writing seriously, meaning that some of my habits, while normal to me, might seem very abnormal to you.


For context, I started this finance blog in July of last year. Before that, I had published 10 or so articles on Seeking Alpha, and a dozen short-form satire pieces on Hard Money.

One month after starting Young Money, I bought a one-way ticket to Barcelona and spent the next four months backpacking around Europe. My average length of time in each city lasted four days, and I spent 90% of my nights sharing hostel dorm rooms with strangers.

At the onset of this trip, I had yet to figure out my voice, build any momentum whatsoever on any of my content, grow a social media audience, or do literally anything that would validate me as a writer. I had published 10 articles on this blog and written one travel blog piece that explained how a quarter-life crisis had driven me to live out of a backpack in foreign countries for months.

I had 900 Twitter followers, 400 email subscribers, a plane ticket to Barcelona, and no routine whatsoever.

These were the worst possible conditions in which one could begin their writing career.

Now that you have some context, let's answer a few questions.

Where and When Do I Write?

Many writers, probably most writers, recommend having a set time and place where you write every single day to help establish a routine.

In On Writing, for example, Stephen King talks about how he aims to spend four hours every morning writing at his desk, situated in the corner of his office.

Thankfully, I didn't read On Writing until a month ago, because at the onset of my writing journey, this structured schedule wasn't possible.

I couldn't carve out specific time slots to write each morning, because some mornings I would be on trains or planes. Sometimes I was out til 5 AM and didn't wake up til noon. Sometimes the wifi at my hostel would suck, and I'd need to find a cafe. I quite literally never knew what country, or even city, I would be in seven days in the future.

Luckily for me, I was too naive to realize how stupid these writing conditions were. I just wrote anywhere and at any time.

I wrote on trains. I always wrote on trains. I wrote in hostel lobbies while the receptionists quietly wondered why I was sitting at my computer for hours on end. I spent plenty of time writing from Starbucks cafes, because they always had strong wifi. three weeks ago, I returned from a bar in Santorini, Greece at 3:00 AM and hopped right on my computer, because I had a really good idea and I didn't want to lose it overnight.

I never stopped to think, "Wow. This really isn't a productive work environment." I just figured that I could churn out two decent pieces on Young Money per week, and I wanted to update a travel blog every five days.

Ironically, the one place that I hate writing from is a stationary desk in my room. When I'm in the States I always go to coffee shops to write. I like the atmosphere. The background noise. The movement, the hustle and bustle, the people.

In 1949, on the heels of his novel The Town and the City being accepted by a publisher, novelist Jack Kerouac began working on On the Road in earnest. After years of traveling to every corner of the country, Kerouac was "itching" to settle down, establish a family home in Denver, and write his next book.

After a few weeks, he came to a realization. He couldn't write this new book with his feet planted in Denver. He couldn't write unless he was moving. As Kerouac put it, "Writing is my work, so I've got to move."

Stephen King wrote about the importance of routine, and I agree that routine is important. But I don't think routine has to be stationary, rigid, and isolated. Chaos, movement, and novelty can be a routine too. I write my best content when the places, times, and environments are dynamic, not static.

I guess I have more in common with Kerouac than King.

Where do I write? Wherever I am.

When do I write? Whenever I can.

Now this doesn't mean that I just write whenever it's convenient. I often write when it's inconvenient. My schedule might be flexible, but my deadlines are quite rigid. I'm going to publish one of these blog posts every Tuesday and Thursday.

More than once, I have written an entire piece just to delete it at 1:00 AM Monday night and start a new one from scratch.

But I'll publish that new one at 7:30 AM Tuesday morning.

You don't have to have a set time and place to write, but you do have to have a system. Chaotic schedules with firm deadlines are systems too, even if they don't seem like it.

How Do I Think of Ideas?

There's no divine inspiration. I don't just sit down and conjure an idea from the air around me.

Inspiration most often hits when I'm not writing. Sometimes it hits while I'm at the gym, mid-front squat. Sometimes it hits when I'm out with friends on a Friday night. It hits while I'm driving around with the top down on my jeep, and it hits in the middle of the night as I'm about to fall asleep.

The key is to capture this inspiration when it hits.

The second that I have an idea, literally any idea, I pull out my phone and text myself the idea. That night, I'll add that short brain blast, plus a few details, to my notes. I currently have a backlog of 87 ideas, if you were curious.

The next question, of course, is what creates the ideas?

Good ideas can't be forced. They appear unexpectedly, of their own accord. But these ideas are heavily influenced by your inputs.

Stronger inputs yield more frequent and more creative ideas. These ideas, if acted upon, created stronger outputs.

The two most important inputs for any writer are the things you read (especially books, but interviews and articles are useful too) and the experiences you have.

So how do I continue to generate new ideas? By reading and doing a lot of different things. Every single piece that I have ever written has been influenced or inspired by something that I've read or an experience that I've had.

Go back and read some of my older stuff.

  • This piece was inspired by this Nick Maggiulli piece

  • This piece was inspired by hyperinflation that I saw in Argentina

  • This piece was inspired by my college football experience

  • This piece was inspired by a Nassim Taleb interview

  • This piece was inspired by a combination of a Tim Urban blog and some personal realizations within my own life

My travel blog has a touch of Kerouac, and Young Money reads like a mix of Tim Urban and Morgan Housel.

I can't emphasize this enough: every single thing that I have written has been inspired by a life experience or a piece of content that I have read.

If I didn't read regularly, my content would suck. If I didn't actively get out and try new things, my content would suck. When it comes to writing, the stuff that I do while not writing is just as important as the writing itself.

I don't look for inspiration in the things that I do and read. The inspiration is a byproduct that hits days, weeks, or months later. All of these inputs float around in the back of my mind, bouncing off of each other. When I least expect it, two of these ideas merge to create foundation of a new article.

More inputs = better outputs.

How Do I Write?

We know where and when I write. We know how I come up with ideas. Now the important question: What does the writing process itself look like? Instead of explaining this in the abstract, I am going to give you a real play-by-play of this recent piece:

In May, I grabbed coffee with a guy named Aris (also, what's up Aris). Aris is my age and working in investment banking. He reached out over social media wanting to chat, as he had read some of my stuff and we both lived in Atlanta. He told me that some of my posts had given him the final nudge that he needed to quit a job he didn't like. Later this summer, he's going to travel Europe for a couple of months before moving to NYC for a new job (now who would do that?)

So we're chatting at a coffee shop in Atlanta, and one thing Aris kept coming back to was not wanting to waste his career doing things that he didn't enjoy. Not wanting to regret his career. He had studied the more senior employees in his company, and he saw that none of them looked happy. Aris realized that if none of his superiors were happy, he probably wouldn't be happy either if he stuck around.

Boom an idea hits: Not regretting your career in 10 years. Use your older coworkers as a proxy for job satisfaction.

There's an article in there somewhere.

Now fast forward a couple of weeks, and I'm sitting down to begin a new piece. What do I write about? *checks notes* Oh this "not regretting your career" idea could do well! How do we turn a single phrase into an article? Let's map it out.

Okay, first, how do you end up working in a career that you hate in the first place? By putting success on a pedestal, by treating your career as a game that you are supposed to win. I've written about that before. This is a good start. Okay, so how do we open this piece up? We just thought of the "game" analogy. What's a game that you can't win?


Okay that's good. We open with Tetris. No matter how good you are at Tetris, you can't win. The game gets faster and faster, more and more difficult. But you can't beat this game. The real-life comparison is that when you get the promotion, or the raise, or the anything, you simply advance to a newer, higher level. There are analogies all over the place with this. Tetris is locked in.

Okay, now how do we predict if we'll be miserable if we continue to play this game? That conversation with Aris about older coworkers. That's perfect.

We're still on this game theme. The goal now isn't to win the game, because you can't win this game. The goal is to find a game worth playing. How do we find that game? Maybe we should avoid the games that aren't worth playing.

There's some Charlie Munger quote out there about inverting...

*Googles Charlie Munger invert*


Invert, always invert: Turn a situation or problem upside down. Look at it backward. What happens if all our plans go wrong? Where don’t we want to go, and how do you get there? Instead of looking for success, make a list of how to fail instead. Tell me where I’m going to die, that is, so I don’t go there.

Charlie Munger

That's good. To find the right game, we need to actively avoid the wrong ones. Inverting helps us avoid the "no's," but how do we find the "yes's?"


*Looks up "Derek Sivers Hell Yeah No"*

*Spends three hours in a Derek Sivers rabbit hole*

We are going to say yes to the "Hell yeahs!" and make everything else a no. This is good. This is good.

But we need an effective way to find the "Hell yeahs!"

Come on, how do we find them? Is there something that you've read? Something that you've done.


So how exactly did this work in my own life? Well I started writing to make some extra side money, and I realized that I was a decent writer, and I liked writing. The next step was searching out people who were making good money by writing. Who are some examples?

  • Packy McCormick and Mario Gabriele turned their personal newsletters/blogs into high-cash flow businesses.

  • Morning Brew and The Hustle sold for millions to Insider and HubSpot.

  • Litquidity's Exec Sum newsletter was bringing in great money through ad revenue and merchandise sales.

  • Morgan Housel was hired by Collaborative Fund to write full-time for them.

Anddd all of this led to me doubling down on writing as a viable career path.

*Takes an hour break, comes back to look at the piece*

Then I spend another hour or so organizing the piece, deleting anything and everything that isn't absolutely necessary (usually means cutting ~600 words), proofreading, then reading it over again.

Once it's done, I think of a picture that relates to the theme of the article. In this case, a crystal ball was fitting. I draw that picture on my computer, save it as a thumbnail, and schedule to publish.

That was how I wrote The Future of You.

If I hadn't read Derek Sivers's stuff, if I hadn't listened to that Munger interview, if I hadn't met with Aris, if I hadn't been introspective about my own writing journey, I wouldn't have been able to write that piece. My inputs were responsible for that output.

This chaotic game of idea leapfrog that I played? That is the process for every single article that I write. The biggest misconception about writing is that you simply take ideas in your head and put them on paper, but this couldn't be further from the truth.

Writing is a journey. Writing, quite literally, is thinking. Writing isn't the transcription of ideas from your consciousness to a physical page. Writing is the creative process that transforms fragmented thoughts into cohesive stories.

- Jack

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Jack's Picks

  • In the wake of the current crypto meltdown, Ritholtz Wealth Management's CEO Josh Brown wrote a great piece discussing regulations, investor behavior, echo chambers, and potential opportunities. Check out his latest here.

  • Consumer sentiment is at an all-time low, but economic data shows that we are doing just fine. Is a recession a self-fulfilling prophecy? Kyla Scanlon broke down "The Vibecession" in her latest post.

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