Baby and dog on a carpet with the baby mirroring the dog's posture and looking at the dog as if in conversation

What I Learned from Over 100 One-on-Ones with Other Writers

An overview of having over 100 one-on-ones with other writers that concludes with a tour of some of their publication tech stack choices.

Jerry Seinfeld describes the path he took to becoming a comedian in the opening section of his memoir Is This Anything? It is really an extraordinary book, but I will admit that I had a tough time getting past the first twelve pages. My problem? I couldn’t stop rereading them. 

For the rest of the year, I am going to rate books on how many pages I get through before I surrender and go back to read the opening of Seinfeld’s book. Maybe I’ll call it the ITA score. Ironically, my ITA score for the ITA? book itself is currently at 8, and I’m barely a quarter of the way through. Let’s ratchet that score to 9 by sharing some excerpts:

I love hearing a laugh that’s never existed in the world before. 

Because every laugh is slightly different. Unique even. 

So these pages are the map of the forty-five-year-long road I’ve been on to become this odd, unusual thing that is the only thing I ever really wanted to be.

Before you rush out to buy his book, consider whether or not you really want to read a 480 page map. That’s not me trying to be funny—you kinda let go of that impulse in the presence of a master. Rather, it’s an admittedly uneven book, which is only natural given that it represents four-plus decades of raw materials. 

Still, these six sentences early on completely rocked my world:

I got better at story structure as the years went on but still find that kind of work a bit dreary. 

But at twenty years old, when I walked into the Manhattan comedy clubs for the first time, every neuron in my little brain just lit up. 

I felt like I had finally found my home on planet Earth. 

And it wasn’t just that I could now immerse myself in the art of comedy, it was also the world of comedians I was suddenly in. 

I have many great friends who are actors, writers and artists of various kinds. 

But when I’m in the company of other stand-up comedians I feel like I’m rolling around in a litter of puppies.

There’s a lot to unpack there. This week’s essay is very much about writing, and I’m a bit self-conscious about diving in and giving hints of the magic and interconnections that good writing reveals to me. Especially when it takes me by surprise, which it did there as Seinfeld builds through acknowledging his limitations  (years, dreary, twenty years old, little brain) and then the transformation (lit up, home, planet, immerse) which is completed by the unification (art, world, suddenly, great and various) that singularizes in the present—because when can you be more in the moment than when rolling around in a litter of puppies

The real power in that passage for me is the glimpse of the powerful combination happening when an expertise, individuals, community, and environment all come together. I’m going to be writing about one-on-one’s, but these weren’t isolated interviews—these conversations happened while immersed deeply in a shared community doing some intense work.

Ever since I fell in love with writing, I’ve frequently reverse engineered why certain passages move me so much. But I typically hold off until after I’ve read the passage a dozen or more times, and immersed myself in its magic. Even at that point, I prefer to not apply the scalpel of parsing, diagramming, and mapping how the writing itself snuck up and captured me. Those six Seinfeld sentences are magic to me and now that I’ve shown how the setup and payoff progressed, hopefully that doesn’t diminish their resonance if they were powerful to you also.

Let’s reset by returning to the imagery of people and puppies. Let’s just keep rolling around for a while.

Photo by Picsea on Unsplash

Creating and Sharing

I recently decided that I wanted to change how I communicated with the world, and had many precedents in mind for what might work best. However, this anecdotal based sampling still left me uncertain. So I decided to join a writers fellowship. I figured that within that assembly there might be at least a dozen or so people trying to answer the same questions I was puzzling through, and we could become sounding boards for each other.

Part of the problem I've been trying to address is how to reconcile two different sets of insights. The first set represents Creating, which centers on how one approaches writing and what might drive the real creativity that leads to something worth sharing. The other aspect can best be described as Sharing. It includes the technical choices regarding the form factors and publication stack, but it also deals with the bigger questions of how creatives find their audience, and readers find their writers.

Looking at creating separately from sharing, it is obvious that in the end they need to come together, as Seinfeld describes:

The real problem of stand-up, of course, is that you must constantly justify why you are the only one talking while a room full of people sit quietly.

One Hundred One on One’s Later

After 100+ one-on-one’s, the last thing I want to do is give a long-winded version of my writer’s journey. Especially after that Seinfeld quote. I wrote about 700 words and didn’t have the heart to share it here. I put it in the community channel as a comment for this issue. Read it later if you are having trouble falling asleep.

One of the great things about joining a community of writers is that you don’t have to constantly probe for willingness to talk about writing. You don’t have to throw away 700 words. Likewise for any other intentional community. After a dozen or so one-on-one’s, I realized that I was coming out of these exchanges very energized and enlightened. When I described that, a friend made the comparison to exercise: “It’s like when you work out for an hour, and you gain two hours back in productivity.” Oh to be young again. 

Now that I have had over one-hundred one-on-one discussions, let me skip right to the heart of what I learned. Let’s begin with the initial conditions. I wondered about the persistence of the writing fellowship. What could I do to extend its value for several years beyond its eight week time frame?

  1. The first choice would be establishing personal relationships that might continue to grow in the years ahead. The limitation there being that most people’s lives are already fairly full and committed. What would this look like if it worked?
  2. The other obvious choice would be to utilize the program as an accelerant for a writing project that would continue its benefits far into the future. The fellowship period could act as a forcing function to meet deadlines and expectations for output.

It felt like the right mixture could create a tremendous amount of momentum. With that in mind, I chose a topic that I thought might prove valuable to the our writing community. Solving the tech stack for putting together a newsletter, various forms of content, projects, products, and how to include readers via some form of commenting and community was turning into a tangled and daunting research project. What if I helped solve for that and wrote about it?

Final Exit

I’ll do one last probe for willingness here—most of the rest of the way is about writing and publishing. Feel free to check out now if this isn’t your thing. My only request is that you take note of my new way of ending every newsletter. I want to always provide at least one reward to the patient and kind, so I started it last week with My Old School being the closing words and a link to the Steely Dan classic. This week is going to be a hard one to top. It introduces the newest and youngest member of The Doobie Brothers:

Just Get Started 

If you are looking to launch a newsletter, honestly, just get started. And the simplest way to do that is to use Substack. If you previously thought that you had to get a domain, set up a website, figure out how to secure it, but didn’t want to deal with the hassle, then Substack might be for you. Likewise, if you heard of Wordpress, knew your favorite bloggers used it, but got intimidated as soon as people started discussing Wordpress Themes, then Substack might be for you.

Honestly, that pretty much describes my thinking twenty weeks ago.

Substack does provide additional help beyond ease-of-use. They provide many guides and resources, and they even have a program that provides legal defense for writers. They have also added the ability to add a custom domain. Substack is looking like a winner in the space, so their features and capabilities should continue to grow. 

Besides, you can always change later. 

Just get started.

Wanting More Control

There are many writers who have a big picture in mind for what their content needs from a publication platform. They are guided by the basic philosophy of wanting to retain control of all their content and have the most direct relationship possible with their audience.

After 100+ conversations with other other writers, it’s clear to me that many of them have worked out some key aspects of the problem and are in the process of addressing that into their workflow and tech stack decisions. Allow me to share just a few of those discussions. The insights range from the very creative to the workaday.

My favorite session during the fellowship was a co-hosted discussion by Salman Ansari and Nate Kadlac, demonstrating how they used the powerful digital illustration app Procreate. It immediately got me thinking about how illustrations, photos, and design elements could add a personal and defining touch to my own writing. Nate is also an amazing photographer:

Photo by Nate Kadlac on Unsplash

Salman is one of the most creative people I’ve met and is a rare person who can honestly describe themselves as Founder | Engineer | Writer | Artist. Salman’s design intuition and the way he prioritizes getting all of his traffic back to his website is worth a close look. His site also includes explanatory videos about those design choices and you can see how he integrates his Substack newsletter and Instagram pages. 

How to integrate a newsletter with a personal and professional site was one of the first questions I had for Tom White. Tom has given a lot of thought about the need to have a professional website presence beyond one’s newsletter publication. He sends out a weekly newsletter via Substack and then reformats his writing on his website for discoverability and navigability. is an effective distribution platform for someone who wants to occasionally publish but not be tied to the expectations that come from publishing a newsletter. Also, the design elements are terrific. Everyone in our writing workshop was knocked out by the formatting and design choices our friend Simone Keelah utilized in “6 Surprising Things I Learned About Quitting the Corporate World,” a piece that absolutely sizzles. 

Our fellowship not only had great writers figuring out their own tech stacks, it also boasts Parthi Loganathan, who is a YC founder who has created his own solution: Letterdrop also has its own Slack community, public discussions about tech stacks, and a fast growing clientele. 

When I spoke with Parthi, I got the sense Letterdrop was trying to keep the simplicity of Substack but incorporate all the power tools behind the scene. For those techy enough to know what this means, he is also starting to open up Letterdrop more so that it can also do things such as acting as a headless newsletter CMS with integration into Webflow and Wordpress. That will be for writers who want more versatility to better embody their brand than some of the platform solutions offer. After several communications with Parthi, I’d suggest that if there is something you want but he hasn’t built it in yet, let him know and he will work with you to add it.  

For many of us, having a newsletter is simply a complimentary vector in our professional lives. Steve Morin was telling me how he has enlisted the help of some talented part-time digital designers and creators to assist with the workflow of his newsletter. He likes the ability to work with a talented team while benefiting from making sure that his newsletter doesn’t become overly reliant on any one team member. For the many of us who see our publication’s mission as a way of paying it forward, what I like about Steve’s approach is that it adds another dimension to opening up opportunities for other creatives. 

Racha Ghamlouch faces unique tech stack challenges writing for the Middle East and North Africa (MENA) markets. It is professionally expected in her region to have a well designed which limits the ability to use less customizable publishing platforms. In addition, it is vital to be able to provide enough analytics for advertisers given that the paid subscription model faces low receptivity in MENA. The limitations of support for Arabic has her using a combination of mailchimp, feedly, ifttt for automation, airtable google sheets. Racha has spent the last decade at the forefront of the MENA tech world and is loaded with insights as to how innovators have adapted to this unique market.

Additional Innovative Publication Stacks

Sharing solutions to the tech stack challenge for publishing content and building community is a compelling topic for many writers. During the several dozen hours I spent wading into the weeds, I kept my eyes open for signposts of what others had done. Given my own vision, I was particularly interested in the approaches of those who are combining publication with community—such as this from the founder of Ness Labs:

Put all of these approaches together and we have a powerful start in helping each other reverse engineer the maze.

One of the reasons I never wrote that essay on building a tech stack is because I found a better one to share. Rob Hardy wrote “Building the Perfect Membership Publication Tech Stack”. 

In the end, Rob built two tech stacks, one simple and one complex. Interestingly, although Rob later abandoned the complex version, I found that with just a few modifications it completely fit my needs. It also had the advantage of leading me towards Webflow, and so much of what I am doing with other projects are also being built in Webflow. I discuss my tech stack in more detail in the community channel.

Digital Gardens

Let’s return for a moment to Seinfeld’s puppies. So many of those one-on-one conversations were magical. This will probably embarrass him because we only had a few conversations, but Salman had a lasting influence on me. Our conversation was my first introduction to the concept of a digital garden and how this approach Opens the door to a ton of new possibilities of how to write notes and let readers navigate them. 

Salman also wrote a viral essay about embracing his inner polymath. I think that is why his approach resonated so deeply with me. It was refreshing to see how someone could embrace multiple pursuits. There were elements and choices in his publication stack that pointed the way to how I might likewise embrace my many interests.

By the way, when you go read Salman’s polymath essay, I’d just like to add one more point about the term “Jack of all trades.” In 1592, it was applied to dismissively refer to an actor-turned-playwright. That was the first published mention of William Shakespeare.   

Technically speaking, the AlwaysInvert publication stack is a form of digital garden. My only issue with that description is that I’m really not into gardening. Earth is not my element. It is too anchored. I want to keep moving. I prefer water. Not just the element water, anything to do with water. 

Photo by Jon Flobrant on Unsplash

One of my favorite pieces of wisdom is Heraclitus’s insistence on ever-present change: 

No man ever steps in the same river twice, for it’s not the same river and he’s not the same man.

I consider much of what I’m doing as a bit like being on a raft on that river. Not an impressive vessel, but rather a rickety, thrown together with the scraps around me, sure-hope-it-works assembly of talent and time. With no guarantees it will stay intact through normal days and nights, let alone a storm. But no place I’d rather be.

Depending on your element, AlwaysInvert can be a garden or a raft. To me, it’s a bit of both. I’m planting seeds and will be back to cultivate and harvest later. It will be fun to regularly check in, but in the meantime, I’m restless, and as the song goes, the water is calling my name, and the raft, well, she’s ready for floatin’.

Join the Community

Join this conversation in the dedicated channel over at

Articles we think you will like

The Art of Communication

Technology is enabling new possibilities for communication, and we are eager to explore and experiment.

© 2022 Always Invert. All rights reserved.