August 2025 Recap

I write these monthly recaps to slow down, digest my thoughts, and make ideas more permanent. It’s a way to invite collaboration by sharing where I’ve been and where I might be going.

Writing

From Audio to Insights: My Experiments with Podcast Research

Maine Outsider: Invites 96, 97, 98, 99

Small Wins

First newsletter advertiser

I opened up a sponsorship slot in the Maine Outsider. After running it at a loss for two years, it felt like time to reward myself a bit. The first sponsor was referred by a reader.. He builds and manages Hipcamp locations (small private campsites) around the state in remote settings.. He also does recreational land consulting, which is something I’ve been interested in for a while (mentioned in my ideas vault post). We’re meeting next week, which is a fun unintended benefit.

Am I a runner?

I ran the fastest mile of my life this week. At the start of last week, I set a goal to get up and run at least one mile each morning—not as a fitness goal, but as an achievable way to get myself outdoors and moving. Yesterday I timed myself on Strava: a 6-minute mile pace. To most runners, this won't be impressive, but to someone who hasn't thought of themselves as an athlete lately, it was surprising and oddly exciting. I didn't know my body could do that.

The Challenge of Legibility

The first month of being on a sabbatical was light, energetic, and unexpectedly productive. I followed my curiosity without the pressure of pitching or making money. I wrote more than I ever have, created more than ever before, and made more local connections. I felt free to be myself and lean into my personal quirks.

The last few months have been different. I have bills and expenses. I need income. That’s a fact of life.

I’ve struggled to find a balance between things that make me feel alive and things that generate income. I’m a free-range person who tends to boundaries between disciplines as fairly arbitrary.. The pattern of my career is…get a foot in the door, see what’s most needed or most interesting, and do it. I’ve held roles as founder, marketer, designer, product manager, developer, and manager. I follow my nose and get shit done.

That sounds fine until you put yourself into the job market, which values specificity and legibility. Companies often place bets on people they understand. They look for proxies of credibility (education, career trajectory, employer name recognition, etc.) — stories that make sense. My marketing story got muddied when I switched to design, as it was what the startup needed. I compromised my product manager story when I switched to freelance web development to fund a year and a half abroad.

Sometimes I feel a sense of doubt and low-grade shame for choosing to switch lanes so often. I wonder why I struggle so much to package myself in ways that are easy to explain.

I found a mirror for my feelings in two places this month. First, a hybrid profile/personal essay titled Flounder Mode about polymath Kevin Kelly by Brie Wolfson.

I started to reflect on my own trajectory with fear that it didn’t mirror my ambition, work ethic, or deep care about the role of work in a life. Had I pointed my ambition in the wrong direction? What did I have to show for all my effort? Had I made some irreversible, unforced error with my career? How much money had I left on the table? Would the people I respected respect me back for much longer? Despite working my butt off for a decade, I had no expertise and no line of sight into where I was going. I felt immature for placing such a high value on “fun” and “bouncing around,” and full of regret about not picking a lane (or even better, a ladder). It had become hard to explain what I was good at—most importantly to myself.

Second, a short clip from a Jacob Collier concert where he explains his wiggle theory.

To borrow the language of Jacob Collier, I’m still trying to figure out if I can be “wiggly” in a professional way. Or if I need to straighten myself out for money and wiggle on the side.

Metabolizing Curiosity

One thing that’s obvious to me is that curiosity, by itself, is not rewarded. The difference between distractibility and productivity is whether I have an outlet for my curiosity — a way to turn my natural explorations into something of value. The phrase that’s been stuck in my head is “selling your sawdust”, which comes from the idea of selling byproducts.

What that means to me is finding ways to be myself and capture the “byproducts” of my learning with others. I successfully did that with the Maine Outsider. I took a personal habit/obsession of planning outdoor trips in the state and formalized it into a shareable asset for others. To some extent, writing has been an outlet as well. At present, I’m figuring out a way to turn my love for podcast learning into a product others can use.

Podcasts themselves are a perfect example of this concept. Podcast hosts convert personal curiosity into valued public assets by pressing record on their calls and hitting publish.

I have to remind myself that curiosity is largely a consumptive habit. Those who cultivate the habits, practices, and disciplines to process their experiences into creations are rewarded.

Captures

Bookmarks

I bookmarked 46 things this month that sparked curiosity or made me pause. Here are a few that stood out:

ChatGPT Pastor ThreadIn early August, someone discovered that publicly shared ChatGPT threads had been indexed by Google. I couldn't resist digging through them to see how people actually use AI in their daily lives. The variety is fascinating—from a pastor preparing a sermon to someone using it as a dream journal.

Builder as Marketer RoleA case for why building beats talking: actual tools and prototypes communicate your capabilities better than most marketing materials.

Midjourney TVRegardless of how you feel about AI art, Midjourney TV's continuous stream of user creations is enthralling. I recommend hovering over usernames to see the bizarre prompts behind each video.

Caasie - Outdoor Ad PlatformCassie lets you book digital billboards worldwide, from highways to bathroom stalls. My principled side cringes at the ad overload, while my schemer side immediately starts plotting ridiculous campaigns.

Five-Year Plan of China
China releases a detailed five-year economic plan every five years. This was news to me until a podcast mentioned it. It seems worth tracking what the world's second-largest economy says it plans to do next.

Bunkie CabinsThese tiny Lincoln-log style, DIY cabins light up a part of my little-boy brain that’s almost irresistible. I have to remind myself that it’s probably not the best idea to buy a piece of remote land and assemble a tiny off-grid cabin right now.

Hip Camp Fall Foliage MapBack to the topic of “building as marketing”. I noticed that Hipcamp recently launched a fall foliage map, which allows you to visualize fall foliage colors over time and show you campsites in those areas. So simple, so smart.

Threat Intelligence: How Anthropic stops AI CybercrimeIt’s truly a strange time to be alive. This panel, featuring Anthropic’s threat intelligence team, discusses the various ways bad actors are abusing AI, including North Korean employment scams, romance scams, and espionage, among other tactics.