How I Write

When I started writing 11 years ago, I did so the same way most people do: by opening a blank document and typing my thoughts on the page. But each year since then I've subtly refined and evolved my process in an attempt to improve the quality of my writing and its impact. Now with 150+ essays published with over 1.5 million views, I wanted to share every detail of my writing process for fellow or aspiring writers who might benefit from it.

What I write about
In order to write about life first you must live it.
- Ernest Hemingway
When it comes to what I write about, I subscribe to Ernest Hemingway's perspective that our best writing comes from the experiences of our lives. It's no wonder then that 85% of my writing stems directly from my career as a product manager and entrepreneur. I have the most perspectives and insights to share in these domains because I live and struggle with them each and every workday. Writing itself brings clarity, so focusing on these topics has been a self-reinforcing loop, helping me generate even more perspectives on these subjects.

Having such focus has also enabled me to create a unique positioning within the minds of my readers. I'm known as that product guy, so it makes it easier for people to easily recommend me to others or seek me out when they are looking for product-specific content. I'm often given the feedback that many of my essays apply equally well in roles outside of product management and I certainly think that's true. But in a world of information abundance, keeping a tight focus helps me to narrow my target audience and thereby improve my chances of actually reaching them.

All that being said, I do have interests beyond product and entrepreneurship and I have taken the opportunity to dabble in those interests purely out of enjoyment. The remaining 15% of my essays cover everything from career optimization to life hacks to engineering.

One month ago, my wife and I introduced our baby girl, Zoe, to the world. In doing so, I decided to take on a brand new writing project, entitled, where I share all the life lessons I hope to pass on to Zoe on living a happy and meaningful life.

Types of essays
Each essay I write falls into one of these six types. I'll explain each type and share a few exemplary essays.

Personal perspectives
The bulk of my writing stems from me sharing a personal perspective or opinion I have on a specific topic. I wouldn't necessarily call them unique perspectives because I'm certainly not the only one with a particular point of view, but at the same time, they rarely fall into broadly accepted conventional wisdom.

The Art of Being Compelling as a Product Manager
The Hierarchy of User Friction

I also write about the fundamentals of a given topic. My goal with these is to both introduce a beginner to a topic as well as to provide structure to folks who may already be familiar with it.

How to Prioritize a Product Roadmap
Modern Project Management for Product Managers

Deep dives
I also love doing deep dives on topics that I've become intimately familiar with. This usually happens because I'm actively working on a project at work that has resulted in me spending a lot of time on a given topic, making it great fodder for an essay.

A Leader's Guide to Implementing OKRs
A Practitioner's Guide to Net Promoter Score (NPS)

Book reviews
I love reading and sharing my biggest takeaways from my favorite books. With these, I try to bring a personal perspective to the book review as opposed to simply summarizing it. I might share why the book is particularly relevant for product managers or entrepreneurs, for example.

Atomic Habits for Product Managers
What Silicon Valley Can Learn From Bill Walsh's The Score Takes Care of Itself

Some of my most successful essays are actually simply roundups of other people's incredible writing that I've been particularly fond of. In this world of information abundance, the curators who help find the signal in the noise create value.

Top 75+ Resources for Product Managers

Authentic stories
With, I wanted to stretch beyond my conventional writing style and challenge myself to take on a new form of writing. My goal is to teach Zoe dozens of life's important lessons by sharing authentic, vulnerable stories about experiences in my own life. This is the hardest writing I've done to date, but I'm absolutely loving the new challenge.

Embrace your new reality
If you want love

Where my ideas come from
At times I've sat down and done brainstorming exercises to come up with essay ideas for both and My goal during each brainstorming session was to come up with at least 52 potential essay titles so I'd have no excuse not to have content if I wanted to write weekly (though I've never kept up that pace for long).

The reality though is that my best essay ideas have rarely come from these brainstorming sessions. The best ideas have come directly from projects I'm currently tackling at work. They emerge as ideas as I consider the best approach to solving a problem, or the best process for handling a particular part of the product development cycle, or simply from learning something brand new in the course of my work. With every project I take on, I think about what I need to learn to be successful at it as well as once the project is done, what did I learn, either positive or negative, from the experience. All of this makes for great essay ideas.

I've also come up with essay ideas during my dedicated thinking time. For me, that's in the shower and during my runs. It's a perfect time to think deeply about the challenges or victories of the day. In these reflections, insights certainly surface, some of which will make it to my list of candidate essay ideas.

Every morning I spend about an hour reading industry insights. I'm a big believer in deep reading, so I try to critique every piece of content I read, decide where I agree or disagree with the article, and formulate my own opinion from it. During this process, I often come up with insights that I add to my list of essay ideas.

I also get ideas from the conversations I'm having on Twitter and LinkedIn amongst professional colleagues and others in the industry. I'm often responding to questions that are being posed and realizing that they would make for great essays. Or at other times I'll tweet out an insight that becomes the basis for an essay idea.

Finally, as my audience grew, some of the best ideas have come from questions that my readers have directly posed to me. They might specifically ask for me to write an essay on a topic, or more often, simply ask for my input on a particular challenge they are struggling with and those are always great opportunities for essay ideas.

I collect all of these ideas into a single note called Essays Ideas. Most of the ideas initially take the form of a title or headline. Sometimes I flesh them out to include a couple of sub-bullets covering the principle arguments of the essay if I had them at the time.

Now whenever I'm looking to write, I have a rich, constantly growing repository of essay ideas to draw from.

When I write
My favorite time to write is Saturday mornings. I've never been one to sleep in, so the quiet weekend morning with a warm cup of coffee is the perfect setting for getting my thoughts down. During the week I might have earmarked a particular topic that I planned on diving into on Saturday. Or other times I begin Saturday morning with a blank slate and scan my essay ideas note for inspiration.

I used to write all my essays this way. But then I noticed something peculiar. Randomly in the middle of the week I'd be inspired to write an essay and I'd earmark it for Saturday. But by the time Saturday rolled around, I just couldn't find the inspiration to flesh that idea out into an interesting essay. So I started experimenting with immediately writing right when an insight hit me with gusto. What I found was that when I was able to immediately translate that fit of inspiration into a full essay, it not only solved my occasional writer's block but also the words often flew right out of me right onto the page, versus many Saturday mornings where each word felt like a struggle.

Elizabeth Gilbert, famed author of Eat, Pray, Love, describes this feeling as your elusive creative genius. She talks about how the Romans believed that a sort of disembodied creative spirit, which they called a genius, occasionally came to you with such inspiration. Or how American poet Ruth Stone used to be out working in the fields when she would feel and hear a poem coming barreling down at her from out in the landscape and that she felt like she needed to run like hell to get a pencil and paper to capture it as it thundered through her out of fear of losing it.

I've since embraced these fits of inspiration and I'd say about 50% of my essays are written outside of my ideal Saturday morning writing time and instead captured as close to the moment of the initial inspiration. What's been interesting to observe is that these essays now account for far more than 50% of my best writing.

How long I write
I'm often asked how long it takes me to write each of my essays as folks are always curious how I fit in writing as just a hobby when I have always had a full-time job as either a product exec or startup founder.

I unfortunately don't have any sort of super power or shortcut that lets me bang out these essays quickly. I'd say my average essay takes about 4 hours to go through the entire process described here. But the range is even bigger than that: my essays have taken anywhere from 2 hours - 8 hours to write.

What I'll say is that the reason I've been able to write as much as I have is simply because I really enjoy writing. It truly is my hobby and one of my favorite pastimes.

Brainstorming titles
When I sit down to actually write an essay, my first step is to brainstorm and finalize the essay's title. I'm usually starting with a title already since it either came from my essay ideas list or because I had one in mind when a flash of inspiration came to me. But I find its helpful right from the get-go to brainstorm alternative titles. I usually come up with 3-5 alternatives and then pick amongst them.

My first goal with a title is to solidify the point of view the essay is going to take. I think about which of the six types of writing I want this specific piece to take on. If it's a personal perspective, then I ideally want to mention that perspective in the title. Or if it's a fundamentals essay, I want a simple title that defines the topic area. At this point, I may even change the focus of the essay based on a stronger direction I come up with as part of title brainstorming.

My second goal with a title is to make it attractive to my target audience in order to maximize distribution. I initially used to optimize titles just for social media distribution. But what I learned over time is that the vast majority of my readers come from search and therefore I instead think about what titles would maximize my organic search distribution. This involves ensuring I have the right keywords in the title that potential readers are likely to search for.

After finishing the essay I might briefly revisit the title to ensure it still fits, but most of the time the work here has already been done up-front.

Crafting the substance
After I've finalized the title, I then move on to coming up with the content of my essay. But I don't move into writing prose just yet. Instead I'm a big believer in the McKinsey dot-dash storyline method. The most important deliverables at McKinsey are slide presentations sharing progress and findings with each client. What they realized in preparing these decks was that they would waste a lot of time finalizing slides only to have the presentation dramatically altered after reviewing it with the partner on the project. To reduce the cost of this iteration, they moved to initially focusing on coming up with an overall storyline and outline of the main arguments they planned on making and reviewing that with the team before moving into the more expensive step of finalizing slides. This outline took the form of a two-level bulleted list. It gets its name dot-dash because Powerpoint by default makes the highest level bullet a dot and then the indented bullet a dash. This bulleted list covers each slide and the primary arguments or stats they plan on showing on each slide.

This is exactly the same way I put together an essay. I start by putting together a dot-dash outline covering my primary arguments, facts I plan on citing, quotes I plan on including, examples I plan on sharing, and even specific sentences that come to me. I then start editing this until it flows well: moving arguments up and down, adding details, cutting out entire sections, etc. I'll do all of this just in the form of bullet points. It's far cheaper for me to iterate on the substance and the structure of my writing in bullet form than it is to do so in prose. This ensures that once I move into prose, I'm rarely moving sentences or paragraphs around or re-writing major parts of the essay because all of that has been largely resolved in the initial detailed outline.

I also find this practice helpful in separating concerns. In this phase of writing, I'm entirely focused on the substance of my essays. What are my primary arguments? What are the supporting ideas? Do I have enough examples to illustrate my point? Is it credible? All of these are great questions independent of actually crafting prose which I save until the next phase.

Crafting the style
I then move on to actually turning my dot-dash outline into actual prose. At this phase, I'm largely focused on the style of how I want to express the substance that I outlined previously. I spend a lot of time working through word choice, transitions, tone, flow, and more.

Strunk & White's handbook entitled The Elements of Style has been my biggest inspiration for writing prose well. While the grammar rules for English are pretty straightforward, they leave you with an incredible amount of flexibility on how to craft your words. Strunk & White's handbook shares specific writing rules to live by to help drive clarity and conciseness in your writing. While I don't follow every rule in the book, rules like active writing, consistent subject across sentence phrases, and positive writing amongst many others are all incredibly helpful to ensure each word adds real value in my writing.

Editing for clarity
Equally important as the initial writing is the subsequent 2-3 editing passes I take over the essay. Most of my editing involves shortening sentences, removing unnecessary words, simplifying language, and ensuring consistent language and tone. I find it most helpful if I can get at least a few hours break between writing the initial essay and the last editing pass. Taking a breather and then coming back to it helps me read the essay with fresh eyes and I often find issues I initially overlooked.

Adding links and graphics
I then go through the essay to find opportunities to add links to relevant content. These are either other essays I've written that I mention in the essay or links to external resources to help further explain concepts I only lightly touch on. I also hand-select 3 of my own essays to include at the bottom of the piece in a related essays section to help draw readers to other relevant essays they might enjoy.

In the world of social media, I've found it helpful to have an image associated with every article I write. I try to come up with a relevant visual I can construct that helps illustrate the essay. That's often hard to do, but well worth it when such an idea comes to me. When I can't, I'll look for an appropriate stock image or create a simple graphic with the article's name and an interesting background image.

Scheduling for optimal readership
When I started writing I used to simply publish an essay as soon as I had finished it. But over time I experimented with various publishing times to try to come up with the optimal time for maximizing readers. That time has changed over the years but currently I'm finding Sunday evening to get me the most consistent results. I also don't publish more than one essay a week. But sometimes, due to fits of inspiration, I might actually author two essays in the same week. Because of this, I maintain a simple content calendar that tracks essays I've published for the year, upcoming essays that have been written, as well as essays I plan on writing.

Sharing on social media
As part of the essay writing process, I also author the post I plan on sharing on Twitter, LinkedIn, and Facebook. Since this is my chance to entice potential followers to read the essay, I express far more than just the essay title in the post. I try to get at what's interesting about the essay, share some of the primary arguments, or acknowledge the inspiration for the essay.

Building an audience
Ever since I started writing, I knew I wanted to build an audience of interested readers to accelerate the impact of my writing. I initially did this by encouraging readers to join my email newsletter so that new essays were automatically delivered to them. Over time I also began to encourage readers to follow me on both Twitter and LinkedIn. Now after publishing a new essay, I always share it across all three channels to ensure readers can find it on their preferred channel. Having a built-in audience eager to read my next essay has certainly been a key contributor in my motivation to keep on writing over the years.

Engaging in the conversation
Part of what I love most about writing is hearing different perspectives on my writing from readers. I originally did this directly on my website via Disqus comments. But I ultimately abandoned it because of the dual problems of too much friction for folks to add a comment as well as the spam that often resulted. Fred Wilson recently abandoned Disqus on his own blog as well, now encouraging readers to engage in the conversation on Twitter. Since then most of the conversation around my essays happen on Twitter, Facebook, and LinkedIn. While it's frustrating for the conversation to be bifurcated away from the essay, the depth of conversations I have on each essay are super fun and insightful on all three networks. I've also updated essays based on the great feedback I've gotten from readers to make it even more compelling.

My email newsletter has also been a fantastic way to engage with readers as they can simply reply to the email with any thoughts they want to share with me. I've started so many interesting conversations with folks through this process and actually met many of my readers in person because of it.

Measuring success
When measuring the success of each essay, I look at it both quantitatively as well as qualitatively.

From a quantitative perspective, I first look at reach in terms of views of the essay. It's important to look at this metric both from a short-term perspective (first 24 hours) as well as long-term perspective (rest of year). The short-term captures the initial traction on social media and the long-term captures the traction from organic search. I also look at the number of new email newsletter subscribers I generate from the essay to get a sense for how well the essay resonated with new readers.

More important to me than the quantitative feedback is the qualitative feedback I receive directly from readers. These are the social media comments and emails that readers send me with feedback on each essay. The messages I love are when readers tell me I really made them think, changed the way they thought, or even better, inspired them. Receiving these kinds of messages illustrate the power of great writing and are what fuels me to keep on writing.

My writing stack
I've experimented with a variety of software & services over the years to facilitate authoring, publishing, sharing, and analyzing my essays. Here is look at my current writing stack:
  • Notejoy - I write all of my essays in Notejoy. It's also where I keep every essay idea I've ever had as well as my content calendar of upcoming essays. There are a lot of features we've built into Notejoy that make it ideally suited for writing: focus view to hide all distractions, keyboard shortcuts & markdown to keep you especially productive, and a real emphasis on speed, to name a few.
  • Grammarly - I find that Grammarly goes well beyond a traditional spell-checker to find common issues in my writing. I always appreciate doing a final run through with Grammarly before publishing to find anything I might have overlooked.
  • Homebrew CMS - I built as a custom CMS. It's been a fun side-project to keep my coding skills sharp over the years. For others, Wordpress and Ghost are great off-the-shelf options. While I've published to Medium and LinkedIn in the past, I've stopped doing so as I think it's so important to own your audience and author on your own platform. And I can still get the benefit of my LinkedIn audience just by sharing my essays on there.
  • Sumo - I use Sumo to allow readers to easily subscribe to my essays via a pop-up form on my website.
  • SendFox - I use SendFox to automatically email out each essay to my email subscribers after I hit publish.
  • Buffer - I use Buffer to schedule my Twitter and LinkedIn posts after I publish each new essay.
  • Pablo - I occasionally use Pablo to generate an image for my essays when I haven't come up with my own unique image to illustrate the essay.
  • Google Analytics - I use Google Analytics to provide analytics for my website, leveraging it for both user acquisition and engagement stats.
  • Tweetdeck - I monitor any Twitter mentions of my website using Tweetdeck so I can like and respond to those mentions and participate in the conversation around my essays.

So that's a wrap on the detailed look at my writing process. Keep in mind, there is no right way to write and this is just what has worked for me. But if any of these techniques resonated with you, feel free to steal them and make them your own.
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