I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Saturday Reflections, I take time out to reflect.
After yesterday’s semi-freewrite about freewriting and fiction (semi- because I did edit it while and after writing), I started to think about how this concept could be applied to investing.
During 2025, I started using market timing rules, with some success, to decide when to get in and out of the various ETFs I hold in my non-retirement portfolio. This allowed me to get myself back into the market after Liberation Day and exit Bitcoin when it faltered in october. The rules had me adding more and more to my position in gold and my following of gold’s chart even convinced me to ask my asset manager to add more gold to my retirement portfolio.
But market timing rules alone do not a portfolio plan make. In addition to knowing when to get in and out of particular positions, you also have to decide at a meta level which positions to track, and what size positions to hold, and whether to scale in and out of positions based on market timing rules or go all in and out when rules are triggered.
I’m thinking about what freewrite investing might look like. And also thinking of possibly a better term for that: Reckless Investing? Freestyle Investing?
In The freewriting way of life, the article that inspired yesterday’s post, Oliver Burkeman offers that freewriting is not just for writing:
Hopefully by now it’s clear why this has relevance beyond writing. You might speak, for example, about the “freewriting approach” to personal change: not trying to devise a detailed plan for guaranteed success before diving in, but diving in now, then course-correcting based on your experiences. (“Acting is a form of planning,” as Dan Pink puts it.) Or the freewriting approach to difficult conversations: setting the intention to be honest and authentic, but then just going for it – as opposed to, say, getting ChatGPT to prepare talking points in advance, so you can steer things the way you’d prefer.
Why does this approach work? Burkeman says:
In the end, I suppose that this unclenched approach to life works because it reflects how things actually are. We all are freewriting our lives, inevitably, whether we like it or not. Even the most hidebound plan-maker and routine-follower is still choosing, again and again, to keep following those plans and routines, in each new moment that arises. And even the most anxious worrier, forever trying to rule out future uncertainties, remains subject to the fundamental truth that anything could happen at any moment.
Unclenching into life demands that we relax in the midst of the uncertainty and insecurity, because “in the midst of the uncertainty and insecurity” is where we always are. The reward is the aliveness, agency and sense of purchase on life that comes from no longer pretending otherwise.
The reason I started to use market timing rules was because combining my emotional temperament with the uncertainty of market outcomes was leaving me (1) constantly freaked out and (2) without good performance in my portfolio. I needed something other than buy-and-hold investing.
At the same time, I really love following market news and analysis, studying up on contrarian strategies (like replacing bonds with precious metals and alts — not really contrarian anymore!), and making ETF buys and sells in my portfolio.
A freewrite approach to investing allows me to unclench with respect to my investments. It allows me to “relax in the midst of uncertainty and insecurity” and lean into “aliveness, agency, and sense of purchase on life.”
What would a freewrite approach to investing look like? I’m in the midst of developing it, but something like this:
- Start with the ETFs you already have
- Establish trend-following rules for buying and selling (and how you scale into and out of positions)
- Look at close prices for each ETF on a monthly basis, and review charts to see if any buy/sell rules have been triggered
- Don’t plan for a specific allocation across asset classes, let it emerge from your buys and sells over time
- As you come across new ideas (like a precious metals fund, check out GLTR) consider these for addition based on their current trend
- Use stop-loss orders for new positions (or mental stop-losses) to immediately get out of situations where a particular position is deteriorating
- Add intuition and conviction filters on your buys and sells – this can override your rules
Rules alone won’t tell you what to add amd what to ignore, what to lean into, and what to let lie fallow. That’s why you use your beliefs and convictions to select the “characters” (positions) in your portfolio. You treat your portfolio as a developing and evolving, almost a living thing. You quickly prune losers and add to winning positions. You know that course correction is ongoing and doesn’t mean you made a mistake. It means you are surfing the waves of investing uncertainty all the time. You radically accept the results and constantly improve your process.
Here’s a chart Gemini made for me.
| Feature | Standard “Reckful” Investing | “Reckless” Investing |
| Starting Point | A rigid 5-year plan | A small, experimental position |
| Error Handling | Ego-driven “holding for recovery” | Quick exit (the “Mistake Tax”) |
| Growth | Rebalancing (selling winners) | Compounding (adding to winners) |
| Decision Making | Spreadsheets and forecasts | Intuition + Simple Timing Triggers |
I’m not sure I would call a quick exit the “mistake tax” because a position going down after you chose it doesn’t mean you made a mistake (you were following your rules, right?) I would think of it more as the “uncertainty tax” or “uncertainty toll.”
I’m largely following this plan already, but need to enforce a bit more discipline on my monthly buy/sell days. I’ll be working on figuring out my approach today.