I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Sunday Planning, I plan for the week ahead.
I came across a post on Reddit yesterday about Substack (the newsletter platform I use) as a growth platform. And it’s true that it is:
There are recommendations, Notes, rankings, paid conversion, welcome emails, subscriber dashboards, growth loops, social proof, audience portability, cross-promotions, network effects. It is not fully algo-optimized in the TikTok or YouTube or Instagram sense, and that’s part of the appeal, but it is absolutely a growth-oriented platform.
The mechanics are there, and they work. Intimacy converts, trust retains, taste differentiates, and voice compounds. A direct relationship with readers is beautiful, and it is also a business model. Substack is not currently an ad-driven feed in the way the giant social platforms are, and that’s part of its moral and aesthetic appeal. But if the platform is not primarily monetizing by shoving ads between posts, then the money has to come from somewhere, and that somewhere is paid subscriptions.
My immediate response was, “Wow I’m not using it well enough to drive growth!” This is the achievement society — the burnout society — in action. Proposing that everything I do must be about making money, building an audience, optimizing my self and my actions for more and more external validation.
I like writing on Substack because it’s a setting where I take a bit more time to formulate an argument and refine my ideas than what I do here. What I don’t like is how it puts subscriber and view numbers right in my face when I go to do that.
I get that a little bit here with WordPress.com. When I go to the dashboard, the view stats chart is the central item that’s displayed. I get ten to twenty views on each post and occasionally multiples of that. Sometimes those stats draw my eye, and I click through and check out what people are viewing, as the time that one post got 1000 views.
My purpose here is to journal my experiences as I figure out who I am becoming at midlife (kind of becoming late midlife now isn’t it? at 58 years old). I do it publicly because it forces some level of attention to formulating worthwhile ideas. This is not Julia Cameron’s morning pages, where you write three pages long-hand as a kind of mental dump. No, I want individual articles to actually say something, first to myself and then to anyone who might stumble across them.
At any rate, I might write a newsletter article this week — I said last week I might write one but didn’t — maybe I’ll start that today. But I don’t have any goal around growing my newsletter right now, even though Substack is indeed a growth platform.
The vision quest continues
I saw the retinal specialist last week and I’ll be getting surgery on my left eye for macular pucker on June 25th. Despite my very flexible schedule I couldn’t take the first available appointment in early June because I didn’t want anything to interfere with celebrating my younger daughter’s graduation from a master’s program. I’m so proud of her and happy for her.
The surgeon was nonchalant about the procedure and the recovery which made me feel a little less worried about it. I’m fortunate that I have a good friend who has had many many vision procedures in his life and talking with him about this has calmed me as well.
options trading continues as well
Last week I tried a few credit spreads to complement the options wheel that I’ve been trading. The options wheel so far seems to suit me better, giving, as it does, a way to conservatively generate ongoing income with an approach that almost never results in recognizing an actual loss.
I currently have short put positions in $BA, $GS, $KO, $MU, $MSFT, $SHEL, and $TSM as well as in $GDX, $QQQ, $XLE, and $XOP. I also have one remaining credit spread in $MCD which isn’t doing well.
Many options traders sneer at the wheel as being mechanical and only for newbies. However, it is not mechanical because you must choose which tickers to wheel, decide on your parameters for entry and exit, size positions to optimize reward versus risk, determine how much of your portfolio to deploy at a given time, and so forth. Having a solid grounding in conventional investment approaches like I do definitely helps with all of that. It’s similar to trading long stock positions but with a little extra probability juice.
I’m enjoying the practice and craft of options trading immensely, so I’m hoping I can succeed well enough at it that it makes sense to continue making it my primary non-writing activity.
What about painting?
I came across two calls for entry last week via the Women’s Caucus for Art – Colorado Chapter (WCACO), of which I am a member. But I’m ambivalent as to whether to submit pieces. I have been painting a bit more and I have a few recent artworks that I feel are worth submitting.
But I didn’t really enjoy participating in shows in 2025 and haven’t submitted artworks to any shows so far in 2026. Also each show would require an artwork dropoff shortly after my eye surgery.
In Essentialism: The Disciplined Pursuit of Less, Greg McKeown writes:
[Only] once you give yourself permission to stop trying to do it all, to stop saying yes to everyone, can you make your highest contribution towards the things that really matter.
In this case, I wouldn’t be saying yes to a person — I would be saying yes to opportunities that have come my way.
It’s hard to let go of a dream, but I’m not sure exhibiting my art in juried group shows was ever a dream of mine. My dream was always to paint giant abstracts, and I have done that. I’m please with the skill I developed and pleased with many of the paintings I’ve produced.
My vita negativa would say “go ahead and say no to this! create more space for what you really want to do!”
What I really want to do is focus my days on options trading. I want to make it the one thing I focus on, letting go of other activities that have so far defined this 1000-day project including dating, contemplating starting a podcast, showing my art, skiing, and surgery (how about no more surgery this year!)
I do also plan to keep writing, here and possibly for more external consumption, on Greensborough Drive (my Substack newsletter).
In her podcast episode Constraint, life coach Brooke Castillo says, “if I have too many things going on and it’s thinking about too many different thing, I create a lot of half-assed things.”
By making decisions about what I won’t do, including traveling and submitting my art to calls for entry, I’m freeing up energy for what really matters to me right now. It allows me to bring the full power of my creativity and thoughtfulness to that one thing.
What if it’s weird?
And that one thing, right now, is options trading. It feels weird. It feels a little wrong, compared to other things I’ve considered and tried.
In Do the weirdest thing that feels right, Charlie Becker suggests that it’s totally ok to do something weird, but it has to feel right.
Adding the “feels right” filter though is likely to keep you away from things that might actually, eventually, be right but that feel wrong right now. Things often feel wrong not because they’re wrong for you, but because they’re going against some societal script that you’ve internalized.
Examples of things that might feel a little weird and a little wrong too:
- Deciding to live permanently single
- Skipping out on high paying corporate work when you get laid off and not going back
- Admitting you are gay, to yourself or other people, and letting go of the demand to pretend heterosexuality
- Replacing your grass with microclover
- Getting divorced, even when your children haven’t gone to college yet
- Becoming a plumber at midlife after working as a professor
- Shopping for clothes at Goodwill even though you have plenty of money to buy clothes from Nordstrom
- Refusing to travel even though the world thinks that travel is such a wonderful thing
- Calling people out on poor behavior, even if they then call you a Karen
- Retiring on less than $10 million
Psychologists including Dabrowski and Loevinger have proposed that continuing to mature as an adult often requires that you do weird things that also feel wrong, because that’s the only way you can define your own path versus the one that your culture would prefer you followed.
The week ahead
So that’s what’s coming up this week ahead: doing what feels weird and what feels a little wrong too. Continuing to blog every day here. Maybe writing and publishing a newsletter article. Walking the dogs. Getting my house ready for my daughter’s move-in by cleaning the carpet. And the main thing: learning options trading, studying technical analysis, developing my custom spreadsheets for tracking positions and P&L. I’m excited for the week. I get to spend my time doing things I really enjoy. How lucky!