I Need Another Term That's Like Stop Loss But For Steering
It's useful for VUCA
Happy Saturday! Today’s newsletter count: 1,056 words and ~ 5 min.
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1 Big Thing: All VUCA Pursuits Need a Stop Loss
In day trading, there’s this term called stop loss. It works like this:
You set a limit of how much loss you can stomach on a particular stock.
Once the price drops to your stop loss limit or lower, your broker automatically sells it at the market price. Thereby, “stop” you from “losing” more.
I’m thinking about stop-loss because I need an equivalent of this term. For when we are trying to accomplish goals despite a lot of volatility, uncertainty, complexity, and ambiguity (VUCA). VUCA is common in many areas, including entrepreneurship and engineering.
Why This Matters
Let’s say you’re trying a small bet on the side in order to move out of full-time employment eventually.
You’re faced with two competing forces. If you don’t persevere enough, you may not see the fruits of your labors. On the other hand, you also don’t want to throw more resources at a venture that’s a lost cause.
Very similar to whether you should hold or sell a stock in day trading.
But, unlike day-trading where the stock price is a clear and unambiguous signal, there’s nothing this clear and universal across a wide range of entrepreneurial pursuits in different industries, be it a VC-funded startup, or a lifestyle business.
I have committed similar mistakes in both directions. My experience is that setting a 6 month limit and do a check-in is the best general stop-loss I can think of. Anything more precise or effective than that may have to be situation-specific.
Until someone comes up with a better term, I’m just going to keep using stop-loss as a stop-gap.
📖 Recent Read: Playing to Play, or Playing to Win
I re-read Are You Playing to Play, or Playing to Win? - Commoncog recently and it talked about the difference of playing to play and playing to win. An example is Roger Federer who wins while playing a harder game.
Federer uses a one-handed backhand — a notoriously more difficult technique than the two-handed version. He also happens to make it look easy. We don’t love him for that, of course — we love him because he does it while absolutely dominating the highest levels of tennis — at least for the good part of two decades.
The problem of playing to play is it makes winning harder. If you’re so hung up about playing to play that you self-sabotaged your chances of success, you’re being a scrub. The article quoted David Sirlin who first came up with the term.
A scrub is not just a bad player. Everyone needs time to learn a game and get to a point where they know what they're doing. The scrub mentality is to be so shackled by self-imposed handicaps as to never have any hope of being truly good at a game. You can practice forever, but if you can't get over these common hangups, in a sense you've lost before you even started. You've lost before you even picked which game to play. You aren't playing to win (emphasis added).
This inspired this week’s newsletter about strategic stop-loss. I initially thought of the following pseudocode:
If you’re playing to play, and still win, continue.
If you’re playing to play, but cannot win, stop and play to win instead.
The crux is, of course, knowing when to stop playing to play and switch, if you’re not currently winning.
💡Accidental Discovery: Co-working Space in Batam
I recently went Batam island for 4 days to get some writing done. A last minute customer request prompted me to research Batam’s native co-working space ecosystem because the hotel wifi couldn’t cut it.
I came across this Batamon.Asia by accident, and will be checking them out again. I seem to have caught them at a good timing as they are in prelaunch mode.
They also help to provide content and software people at entry level offering rates lower than university graduates in Singapore. It does make me wonder if it’s something I can leverage in the next 6 months after my negotiations with my pillar customer.
Trying Something New: 2 Week Ships
In the meantime, I’m trying to diversify my revenue with my SaaS attempts via microconf’s mastermind setup.
Sadly, I have a serious problem with shipping when it comes to my own initiatives without any external deadlines.
But, this phrase (SINGLE FEATURE APP) I stumbled upon in Alex Hillman and Amy Hoy’s launchftw pdf, made things click for me.
I’m still not doing things in the order the roadmap is currently advising, but at least I’m trying something new. Here are two ways I’m doing things differently.
I found a forum discussion where there’s documented pain by other people. So, I found evidence of an actual problem. As opposed to thinking up about possible problems in my head, which was my typical pattern.
I told my mastermind I will solve it as a single feature app within a 2 week sprint. Which I did, and talked about it with 4 loom videos in the same discussion thread. As opposed to over-engineering, which was my typical pattern.
Un-learning old habits is hard. I got some feedback about doing better in terms of marketing it from my mastermind group. If you have any, I’ll be happy to hear. Email me direct, or comment.
I’m keeping the “ship something every 2 weeks” tactic in the foreseeable future. Given my propensity to over-engineer, I will choose a 2:1 ratio where I will execute at least two fortnight marketing sprints for every one fortnight engineering sprint.
To end this newsletter issue back on the theme of stop-loss, I suppose I will run this "ship every two weeks" for at least 6 months before I re-evaluate. 😊
As always, I wish you and your family good health and good fortune.
I see scrubs and "playing to win" as just different levels of a metagame. The losers are those who are really playing for fun but think they're playing to win. Knowing what level you actually want to be on is key.
Here's a great essay on this. He posits that when you're at the right level, you're in flow.
https://www.nextsmallthings.com/p/if-stuck-then-zoom-in-or-out
as for a new term, "Gut check time"?
In a 10-50-90 forecast for the range of outcomes from a probe, activity, or investment, if you were to cross the 10th percentile ("at least this much 90% of the time"), you would execute a graceful exit from the project. I think there are three parameters:
"10" is a lower limit, nominally 10th percentile, that, if crossed, means that you need to exit / withdraw immediately and go through a re-plan
"90" is an upper limit, nominally 90th percentile; if crossed means that you should consider increasing your investment - or at least go through a re-plan
"time horizon" is a schedule re-evaluation point ("a leash or an exploration budget to trigger an analysis of what you have learned") to see where you are relative to the 50% percentile (midpoint of the expected range of outcomes). If you want, you can also pick three limits: the soonest or earliest you can expect to see an impact, the average time you would expect an effect or response, and the "it's not happening" date where if you have not seen an impact by then it's probably (90% of the time) not going to happen.
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I found the Cedric Chin essay profoundly disappointing. He celebrates John Malone as someone who made a lot of money but did as little as possible to improve his customers' lives. I think if I were watching "It's a Wonderful Life" with Cedric, he would get jazzed during the "Pottersville" sequence when George gets his wish and is never born, and you realize what Potters' selfish unbridled greed can do to a community. In Clayton Christensen's "How Will You Measure Your Life," he is clear on the risks of focusing on easily quantifiable and fast-changing metrics (like how much money you made last week or last month) and not paying attention to meaningful relationships that are resilient but will degrade if not adequately nurtured over time. (See https://www.skmurphy.com/blog/2020/02/16/clayton-christensen-on-how-will-you-measure-your-life/ for my summary and analysis). I had dinner with some older men I had worked with in semiconductors. I was surprised at how bitter they were; they were estranged from their wives and children and were surprised that focusing solely on making money for 20 years had destroyed vital relationships in their lives.