SMALL BETS, SMALL WINS

April 21st, 2022

Why is it so important to edge outside of the comfort zone? And why is it called the comfort zone if we’re supposed to get out of it? Perhaps it would be better names the stagnation zone? What exactly occurs in this stagnating comfort zone? We do what is entirely predictable. We stick to the script, ensuring the reliable outcome. There’s no risk in this place, and because there’s no risk, there’s no possibility of any kind of reward outside of what comes with the usual routine. The comfort zone is a holding pattern, and the farther outside this holding pattern we venture, two things happen: our risk of messing up increases, but the size of potential reward also increases.

This is why small bets are so important. Staying inside the comfort zone is like placing a bet in a rigged game: the odds aren’t just high, they are pretty much guaranteed. But so is the pay off of that non-risk, which isn’t anything new or better or interesting compared to what we’ve always been doing. In short, there’s no real risk, and so - no reward. But venture out of the norm, and suddenly there’s a degree of risk. Try your hand at a new skill, test the waters with a business idea, ask that cutie out on a date. All of these suddenly introduce uncertainty, which is synonymous with risk. By mixing our own skills with the randomness out in the world, we engage that uncertainty, take that risk, but also discover and learn, no matter how badly we lose. Getting rejected by the cutie can have the unexpected effect of creating resilience in the face of rejection. A failed business project is almost always replete with lessons about what it means to enter the market, and finding out we have no innate talent for some new skill can create a strange and refreshing sense of being a beginner, like a child working through the first steps of learning.

All of these are relatively small bets. Pouring one’s life savings into a first business project would be a big bet - and an unwise bet. A better version would be to take perhaps 10% of those savings and create the minimum viable version of that business idea and see if it can garner any kind of success - any kind of small win.

Small wins lead to more small wins, and introspect, a course of exploration can look like one giant inevitable win. But like the montages in movies, that’s not what it is. Success begets success. Small wins beget more small wins.

The impulse may be to increase the size of the bet. A small bet worked, why not go for a medium bet this time, and if that works, why not a big bet after that? Surely this is a good direction!

But there in lies the error. The direction of that first small win might not be the overall direction. It might just be the entrance. In the same way that the front door to a house doesn’t indicate the direction to the bedroom. There’s navigation to be done. Which is why its best to creep toward success with a series of small bets and small wins. At any juncture, it might be wiser to cast two or three small bets to see which direction is best instead of one big bet in the wrong direction. 

It’s a bit like playing Marco Polo. Each call out of “Marco” gives an idea of where you should head. But a bunch of small bets versus one big bet is the difference between saying “Marco” a bunch of times to zero in on your opponent, and saying “Marco” once and heading off in that direction which is nearly guaranteed to be immediately outdated. 

Success is a moving target, and each small bet is an experiment to see which direction success might lie. 

A LUCILIUS PARABLE: SMALL WINS

April 17th, 2022

Lucilius was tinkering with a giant robotic contraption in his garage. It was a massive complication which - to his perpetual chagrin - wasn’t working. The robot was supposed to become a general laborer to help Lucilius with his other projects but nothing was coming together the way it was supposed to. He was sitting there, trying to run through all the thousands of variables in his mind which a kid walked into the garage and said:

“Hi.”

Lucilius started, startled and turned to see the kid.

“Hello there.”

“Can you teach me to shoot bow and arrow?”

Lucilius raised an eyebrow, now confronted with the refreshing straightforwardness that children can often display.

“Uh, are you from around here?” Lucilius asked, spotting the kid’s bicycle laying on the driveway.

“I live a couple blocks away.”

“And do your parents know where you are?”

“No.”

Lucilius considered the situation for a moment. 

“Do they know you ride your bike around and talk to strangers?”

“Yea.”

“Huh,” Lucilius sounded, “Well, that’s rather … old fashioned of them, I guess. Certainly isn’t progressive,” Lucilius remarked, more for himself.

“So what makes you think I can teach you how to shoot a bow?”

The kid pointed to a corner of the garage, and Lucilius looked, seeing an old compound bow peeking out from a high shelf.

“Well there you go…” Lucilius laughed.

“I saw it while riding by.”

Lucilius looked back at his robotic mess. It would be nice to take a break, he realized. He couldn’t figure out what was wrong anyway.

“Yea sure,” Lucilius said. 

He got down the bow, and a quiver and handed the two to the boy. Then he took some cardboard boxes from the recycling, cut them to create long rectangles, stacked them, and then rolled them all into a tight cylinder which he bound round with duck tape. He grabbed some rope, a fat marker and with the cylinder in hand he motioned for the kid to walk with him. There was a tree on the side of the house that would do nicely, Lucilius figured, thinking about stray arrows flying further into the back yard. He bound the cylinder of cardboard to the tree with rope, parallel to the ground, making one of its ends face the boy. Then he uncapped the marker and scribbled in a bull’s eye.

“How far back should I stand?” The boy asked when all seemed ready.

“That’s a good question,” Lucilius said. “How far back do you think?”

The kid shrugged. “Maybe here?”

“Do you think you can hit the bull’s eye from there?”

“I dunno.”

“Let’s go with a different strategy then. Come over here.”

Lucilius took an arrow from the quiver and helped the boy set it up with the bow directly in front of the target.

“But this is silly.” The boy stated.

Lucilius looked back and forth between the kid and the target right in front of him.

“Why’s it silly?”

“Because the target is right there!”

“But you’ll get a bull’s eye on your first shot, isn’t that cool?”

“Yea but it’s not like a real shot.”

“Well, think of it this way,” Lucilius said. “You could spend all day shooting at this thing from back over there, and eventually at some point, you’ll hit the target. And eventually after that, you’ll probably hit the bull’s eyes. But it’ll take a long time, and it won’t feel good every time you miss. But if we start right here, you’ll have a small win in the bag right at the start.”

“It’s still not a real shot.”

“Ah, but that’s because I’m not thinking about your first shot, I’m think about how to best get you from here, to over there,” Lucilius said, pointing back where the boy had stood previously.

“Go ahead, just for me, take a shot from right here.”

The kid frowned but leveled the bow, concentrated for a moment, and the let the arrow fly, and indeed, it sliced into the wobbly dot Lucilius had scrawled onto the cardboard.

“Nice,” Lucilius said. “Ok, now take a step back.”

The boy did as Lucilius pulled the arrow from the target. “Now try again from there.”

Lucilius repeated this with the boy until he was half a dozen steps away from the target and the arrow’s landing was starting to veer away from the bull’s eye. But with each shot that landed, the boy was getting more and more excited about the process, eager to take the next step back.

On the eighth step back, the arrow hit the edge of the target.

“Ok,” Lucilius said. “Now we have an answer to that question.”

“Which question?” The kid asked.

“How far back should you stand? We found the answer. This is where you should start to practice. When you can hit the bull’s eye from here, you’ll be ready to take another step back.”

The boy pondered the thought, and then he leveled the bow again, concentrated harder and let the arrow fly. This time it landed closer to the center.

“Look at that. Your first nine shots hit the target and a few of them were bull’s eyes. Imagine how you’d be feeling if you missed all of those shots by standing too far away? Do you think you’d be having as much fun as you are now?”

The boy shook his head.

“Small wins, that’s how you start learning anything.”

And as Lucilius watched the boy take his next shot, his own words echoed in his mind. Small wins. He thought back to the monstrosity that was in his garage, and a pained smile grew on his face. He realized that with the entire project, he hadn’t followed his own advice, the simple strategy where success begets more success.

ATTENTIONAL COIN

April 15th, 2022

It’s a casual marvel that we can drive a car and have a conversation simultaneously. No doubt many will remember that this wasn’t always possible. That first time driving was likely high stress, and laser focus. Don’t distract me! But as time goes on and we learn, we learn exactly what needs attention, and what doesn’t. We start off paying attention to everything on the road, and eventually realize that it’s really only necessary to pay attention to potential dangers, freeing up a lot of cognitive energy that we can then put into a conversation with someone in the passenger seat, or on the speaker phone.

It’s fascinating how this split of attention can fluctuate. Hold on a second, while I get through this crazy intersection. 

Now imagine the partner in conversation is a driving instructor, and the task is to talk about your driving as you drive. You need to describe what you are paying attention to, and why. I’m watching the curb because I don’t want to hit it. I’m watching the lights up ahead. I see kids playing close to the street.

Attention is still split, but it’s been folded back on itself, like one side of a coin that can see the other side. This exercise maps on directly to the meditating mind, but instead of driving, it’s your thoughts and the sensations that arrive via your body, be it sound, vision, touch and all the like. 

Can you report on the flux of your thoughts in real time?

It may at first seem like a paradox. Wouldn’t a report on a thought constitute as a thought? Yes, certainly, but there’s a crucial event that takes place. 

Ordinarily we are on a kind of autopilot, as when we effortlessly drive a car. That mental autopilot is dominated by thoughts about the past and the future at the expense of only paying the slightest fraction of attention to the present. When we take a moment to recognize what sort of thought we are currently engaged in, we are switching from the past or future to the present. It’s merely a question about what is happening right now, as opposed to yesterday or tomorrow. This interrupts the train of thought. 

To bring it back to the driving circumstance, it’s possible to get so involved in a conversation with someone on the phone that we lose track of where we are actually trying to go while driving. Where am I going? I missed my turn! This happens all the time, even without a conversation. We can simply be lost in our own thoughts while driving. But imagine this: would it be just as easy to miss your turn if you were constantly talking about your driving experience? No, you’d be doubly focused on what you were doing.

A moment of mindfulness when we realize that we’ve been lost in thought is a lot like realizing you’ve missed your turn. And people who are just beginning to learn how to meditate often see this experience as a failure. Uh! I suck at this! I was having a thought again! But this instance is actually the hallmark of practice. If a person can have enough of these kinds of moments, then they can begin to expand. The time between realizing what thought we were just having and the next stretch of time we are lost in thought grows, and in this space we have the freedom to recognize what’s going on in the moment - how vibrant the visual field is, that tension in the shoulders we’ve been holding and can finally release, the feel and flow of breath.

Strangely, recognizing failure is the first sign of success in meditation. It’s akin to realizing you missed your turn while driving, sooner rather than later. The sooner the mistake is caught, the less distance we need to backtrack, and the more time we save.

For the novice of meditation it’s akin to thinking: wow, imagine if I’d been lost in thought for another decade or two without ever really being present? Could there be any greater success than taking a moment to disconnect from the mind’s incessant jabber to simply be in the present and take some time to appreciate it?

A NEW TYPE OF WATER

April 14th, 2022

It’s not a coincidence that cities pop up near the water, either on the coast or on rivers. Water provided humanity its first truly asymmetric leverage in terms of raw power. We need only consider the task of moving a 1 ton block of stone. Moving it over land is no easy feat, but get it on a boat and suddenly it’s thousands of times easier to move around.

This leverage of movement extends to our own selves. Before the invention of flying, it was often far faster to sail to the other side of a continent than to make the trek on land. And then beyond this leverage of water a la moving things, the movement of water itself can be used to generate enormous power, be it with hydroelectricity or even with a simple water wheel hooked up to a mill or a factory.

Recently, a new type of water has entered the arena of human leverage: it’s the digital realm. And the best way to see the similarity is to think about the visibility of a message. Before we harnessed electricity, messages had to physically move across land by the means of some kind of messenger. Then the telegraph was invented and the age of digital water began to drip into human society. And today we are awash in a flood of this asymmetric realm. Now a single person - with the right knowledge and know how - can build something from scratch this digital ocean, with very few resources, and if conditions are right, the creation can be leveraged to enormous benefit to the creator, and to others.

The modern tech companies are akin to the Dutch East India trading company of several centuries ago. But whereas enormous investment was required to create state-of-the-art sailing ships, that cost of leverage is comparatively minimal.

Framing the comparison yields a particularly delicious metaphor: How do you interact with this new type of water? In the digital age, do you sink? Or can you swim? Or better yet, have you begun building your own ship? Because unlike the watery realm of earth, the new digital water is infinite, and there’s no telling where one might be able to go.

HYPOTHETICAL DESTINATION

April 13th, 2022

Most goals are possible. But whether they are probable or not, is an entirely different question. Probable boils down to a negotiation with reality. Hard work is convincing, but even then probable and possible remain unknown until the imagined happens.

There’s that old eye roll of a koan: if a tree falls in the forest and no one is around to hear it, does it make a sound?

In this context, it might read this way: If a goal is possible, but no one tries to make it happen, does that mean it’s impossible?

If all is said and done and something that was possible in theory never actually comes to light, does this mean that by the laws of cause and effect in a deterministic universe that such things actually aren’t possible, even if all the ingredients for their being seem quaintly at hand.

The colloquial version of this is reminiscent of something Wayne Gretzky apparently said: you miss 100% of the shots you don’t take.

Is a shot not taken an impossible shot?

Well yes. We have no way of rolling back time to make an attempt. 

Hypothetical destinations, be they goals, aspirations, or even real places never yet visited all remain more in the realm of fantasy and imagination, unless direct and persistent and relentless action is taken towards such things.