Take big bets on a vague long game
Life's not chess. Do risky stuff with lots of potential if you want a more interesting life.
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I’m a big fan of long-term thinking and short-term action. I like to hold a big, aspirational future in one hand, and make decisive, daily choices with the other. But I’m no good at games like chess, that require the ability to predict actions and consequences in a sequence.
What’s that about?
One of the biggest misconceptions about strategy is that you know what all of your next steps are. You plot a path from A to B, with each action described in detail. This is a terrible match for my skills. I think and act fast, and I like to think the hit rate on those choices is about 50/50 though I expect it’s probably worse. Some work extremely well, others fail miserably. I waste lots of time and money on things that go nowhere.
Knowing how every step will work out is not a strategy… it’s a plan. Memorising steps and potential consequences might work for chess, but I reckon it’s a lot harder for life. For our careers, businesses and personal development journeys, there are too many externalities at play. It’s much more useful to have a big, curly, vague goal off in the distance, and focus on the steps we can take in the meantime that point in that direction.
Things that worked
When I started posted regularly on LinkedIn a few years ago, I had 150 connections and no clue where it would go. But my vague logic was: if I built a following there, that would be a positive thing. Five years, over a thousand posts and 31,000+ followers later, and my instincts proved correct. My business has operated exclusively on inbound leads for years and I have an enthusiastic audience who’ve followed me to all sorts of places - courses, podcasts, books, and here, to Substack!
I couldn’t have predicted these outcomes, because I had no idea where my business and career was going. I could easily have bombed and not be talking about it today (survivorship bias, much?), but it felt like one of those options that had a big potential upside, and minimal downside. Plus, the practice of regular, short-form, written audience engagement has had all kinds of other benefits along the way, improving my writing, communication and marketing nous.
I’m taking a similar approach to other writing. First: this newsletter, Wednesday Wisdom. Weekly posts for five years have catapulted this audience from 28 people to many thousands. Now: my Substack. I know I want to be doing more, and different types of, writing as a part of my long-game. I know I’m a writer. I’ve got a few ideas about what shape that might take - a novel, a memoir, and some brewing thinking around experimenting with serialised fiction - but the truth is: I don’t really know. There’s every chance that I will pour thousands of hours into this, and it won’t go anywhere.
But I reckon that’s OK. My thinking is: if there are people willing to pay for my writing, and follow along, that can only be a good thing. Learning how to do that well, and what it takes to grow and nurture a paid audience, will not be time wasted. It’s been a first domino that's required me to invest more time, on a weekly basis, to writing in all forms, which has cascaded into other thing too, like taking writing classes and learning new skills.
The key here is in making choices that will bring emergent benefits and open new doors, even if we can’t directly attribute each step to a specific result. When we see opportunities for foundational choices, that could bring dozens of potential benefits, we really want to consider taking the leap.
Where you’ve done this
We make choices like this all the time, more commonly in our earlier years. Education is a great example. Most 18 year olds have no idea what they want from their career - how could they, they haven’t had one! But they (correctly) surmise that having a degree - and in fact, doing a degree - will open doors to useful future options, even if they don’t know what they will be.
It’s easy to see this stuff in hindsight, but harder for the present and the future. When you’re time poor and battling to cope on the daily, taking a punt on something new, big and uncertain is unlikely to look attractive. But it’s those long-game moves that have the most potential to change your life.
Barbell theory
In Fooled by Randomness (which I also talk about here in relation to career development) Nicholas Taleb espouses his ‘barbell’ theory of investing. Most people, he argues, try to balance risk in their portfolio by choosing moderate risk investments. Balanced funds, and blue-chip companies. This strategy limits downside - but it also limits your upside. Average performers give you average returns - and if all of your money is invested here, you’re overexposed to big market shifts.
Instead, Taleb advocates, you should avoid the mediocre middle and play with extremes. Occupy hyper-conservative (90%) and hyper-aggressive (10%) market positions simultaneously, to limit your potential downside, while blowing open your potential upside.
“If you put 90 percent of your funds in boring cash (assuming you are protected from inflation) or something called a “numeraire repository of value,” and 10 percent in very risky, maximally risky, securities, you cannot possibly lose more than 10 percent, while you are exposed to massive upside. Someone with 100 percent in so-called “medium” risk securities has a risk of total ruin from the miscomputation of risks.”
I’m no financial advisor, but I love this theory as it relates to life in general. So many people live their lives in the middle, taking the foregone path, sticking their necks out a little here and there, but staying decidedly average. They make average choices and, as a consequence, settle for an average life.
But what if you took just a bit of that energy, and stuck it on the roulette wheel? What if you made some long-term punts that have bugger all downside, but huge (and totally unknown) potential upside?
What would that kind of life look like? What would those gambles look like for you?
Til next week,
A
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Love the theory of risk / reward and a financial portfolio that combines super-safe with ultimate high risk / high reward strategy. In life, I often use the philosophy of creating and pursuing my Greatest Imaginable Challenge(s) based on my passions in life/business, what I do best, and where I can add maximum value to myself or others. My wife was super good at this and used intentions to make her reality come true, no matter how big her Greatest Imaginable Challenge was.