I Realized I Was Writing in Iterations

And why I’m shifting toward raw reflections

Last night, a friend surprised me at happy hour with some good, candid feedback. While she reads every one of my Substack posts, she admitted that a lot of them just don’t resonate with her. She gave me a few examples with good explanations, and I realized that her comments aligned with why I wanted to explore a different format in year 2.

In software development, the Agile mindset is built around iterations, or short, focused sprints that deliver usable pieces in discrete intervals. Instead of trying to build a perfect product all at once, software developers ship what’s ready, learn from it, and build on it. In hindsight, I realized that’s how I’ve approached my Substack posts, with each one being a sprint, focused on a small scope of features, shipped regularly.

Photo by cottonbro studio

But behind every post, there are often a set of “stories behind the story” that haven’t yet soaked long enough to be told fully. My friend’s feedback was simply that in trying to stay focused on a topic, some of my posts haven’t been telling enough of the human elements that lie underneath the topic at hand.

Airline rewards

When I wrote about optimizing airline rewards in retirement, I didn’t include the story of the recent memorial service that prompted me to cash in the miles. The trip was for the memorial service of a very close college friend’s mother. I think about this friend often, even though we don’t talk much these days. We’ve lived on opposite coasts, our kids are different ages, and life has taken us in different directions. Yet I still have a photo of us from college with her mom, taken 38 years ago. Back then, I thought of her mom as “old,” but she was actually younger than we are now. Funny how time reframes everything.

That post wasn’t about the memorial, the friendship, or the passage of time. It was about airline rewards. But the “stories behind the story” are still with me, waiting for their own moment.

My Oracle product in the 1990s

When I wrote about Oracle Data Browser, I didn’t include the story of actually making the demo disk that I featured in the post. The demo disk was my first “work from home” project in 1992. With my boss’s blessing, I took the opportunity to work remotely, not from my apartment in Menlo Park, but from Seattle, where my then-girlfriend (now wife) Marsha lived. We were in a long-distance relationship at the time, and that project gave us a rare chance to spend time together. It’s a story that resonates even more now, as I watched my younger daughter’s partner do something similar last year, working from London while she was studying there.

Another follow-on story is that the same Oracle post also sparked plans for a reunion of “Team Browser.” Some of us are having a small get-together in October, and we’re talking about a larger get-together in 2026. So even though I didn’t tell the whole set of human stories, getting something out there served a purpose. It started a conversation.

My second startup

When I wrote about my second startup, I highlighted data-enabled voice conferencing. What I didn’t describe were the friendships that shaped that journey. In separate posts, I’ve mentioned these friends when writing about guy’s trips and navigating the friendship recession. After all, these friends remain important parts of my life. But I haven’t yet told the story of how the company itself created the conditions for those friendships to flourish. That’s a story I have been encouraging one of these friends to write about on his Substack, as he has been gathering many of the artifacts for such a story in the thirty years since we started working together there.

Going forward

These “stories behind the story” weren’t edited out because they didn’t matter. They were deferred, or perhaps held back with intention. Some stories have had years to soak, like my reflections on my dad’s dementia or the decision to retire. For others, the stories (or at least my understanding of them) are maturing. Time helps to provide context, and I want to give some of these stories more time before I write about them in an essay format.

That’s why I’m planning to shift gears with this Substack. In just a few more posts, I’ll move away from standalone essays focused on single topics and begin exploring ideas that span multiple dimensions. I believe starting with audio will engage my mind differently. Verbal conversation tends to be more free-flowing than the structured nature of writing. To share these thoughts in real time, I’ll be using Substack’s podcast feature. I’ll also be experimenting with an AI notetaker to help organize these reflections and send out email summaries. More structured, topical essays like the ones I’ve written so far may return later, but for now, I’m excited to try a more fluid, conversational approach.

This isn’t just a change in format. It’s a change in rhythm. I’m excited to start sharing stories with you in new ways. Let’s see where this goes!

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This is my 102nd post on this Substack. I’m nearing my one-year anniversary of doing these (about) twice a week. I’ll do two more posts in this format to wrap up the year. For my second year, I’m going to change things up in four ways:

• Change from semi-weekly to weekly format. I understand your inboxes get full!

• Add a podcast format (Apple Podcasts, Spotify, YouTube) for more raw thoughts and for more passive absorption. I have heard the feedback that people don’t really read anymore but like scanning emails.

• Use AI to produce scannable emails. I’ll use an AI notetaker to create show notes of these podcasts to distribute as an email newsletter. The intention is to make the emails more scannable than the current essay format.

• Cover multiple smaller topics, rather than one central topic (like this and this). I found that the experimental posts I did with multiple smaller topics resulted in more engagement during conversations with friends throughout the week.

I’m looking forward to changing things up! Let me know how this goes!

In the meantime, please make sure that retiredpdx+b-sides@substack.com is in your Contacts list so my podcast emails don’t go in your Junk E-Mail folders. The emails for the podcast will be coming from that address. I will follow up with the Apple Podcasts, Spotify, and YouTube URLs once I post my first episode.