Everyone has a different level of risk tolerance. While I think there are extremes in either direction that are probably unhealthy, I’m sure there’s no exact correct level. What works for you doesn’t work for me, and that’s fine.

But what I notice is that people are often either extremely inflexible with their level of risk tolerance (leading to only even contemplating a very narrow range of behaviors) or they fail to adjust their behaviors when facing risk outside of their normal tolerance range.

Sometimes both!

Let me give you an example. Bob has a nice job at a mid-sized company making a reasonable salary. He’s good at his job and has a good relationship with his peers, so he isn’t especially worried about sudden job loss. As a result, he saves at a nominal rate.

Bob gets the opportunity to work for a much larger company at a much higher salary, doing largely the same job. He takes it because the raise is nice!

But here’s the thing: at the larger company, his job is less secure. He’s paid more, but larger companies make big decisions regarding their employee population based on many factors. Bob might be great at his job and beloved by his manager, but the company might have to eliminate 10,000 people as a business need and Bob might be one of them. The person making that decision doesn’t even know who Bob is. Any way you slice it, Bob’s job is less stable, even though he makes more money.

That, by itself, might be a fine trade-off! Like I said, everyone’s risk tolerance is different. But you want to know what I’m pretty sure Bob didn’t do? If Bob made 40% more money working for that larger company, I’d bet that Bob didn’t take that extra 40%, drop it immediately into his savings & investment account, and continue to live on the same take-home pay.

Nope. Bob took the higher salary, increased his lifestyle accordingly, and didn’t adjust his risk mitigation strategy at all. Now he’s in a risker position and he has more to lose.

That’s what most people do! They settle into a particular balance of risk/reward, and then if they see an opportunity for a higher reward, they don’t pay attention to the increased risk – especially if that’s the order. People are good at spotting “if I increase my risk, I might increase my reward” scenarios. They’re bad at spotting “my reward is increasing, which likely means increased risk in some way” scenarios.

The lesson here is not to avoid ever going for more reward. It’s that you can go for more reward even with the same level of internal risk tolerance as long as you adjust your risk mitigation strategy accordingly. You don’t have to constrain yourself to one narrow set of behaviors because you have multiple levers you can pull to keep the total risk level constant. You just have to adjust accordingly.

Why is it that my obsession with the perfection of a task is inversely proportional to the importance of that task?

I think perfection is highly overrated. Most of the time, since perfection is so subjective to begin with, you shouldn’t agonize over getting things exactly right, because the marginal benefit to the increased time and effort is almost never worth it. Most other people can’t tell the difference between your 90% and your 100% and even if they could, they’d often prefer the 90% version in a quarter of the time or for a quarter of the cost. I want my heart surgeon to aim for perfection, but few others.

Of course, maybe that’s the answer to my question! When I get truly obsessed over perfecting something, it’s invariably something only I will ever know about. The exact right way to organize my tools, perhaps. Or the perfect little fix to some minor irk that I’ve encountered. Since no one else will no – but I will, every day – the “perfection perception” gap disappears.

You can do things any way you like, but the order matters. Vent before you try to make progress. Stretch before you run. Sharpen your axe before you cut.

If you’re feeling stuck, nine times out of ten, that’s the solution – you’re doing things in the wrong order.

Here’s an interesting little challenge for you: say the phrase “Coca-Cola” three times without your lips touching. Make sure not to let them touch at all!

Did you do it?

Did it sound kind of absurd?

Did you make a silly face while you were doing it?

Okay, now do this: say the phrase “Coca-Cola” normally.

Hahahahahaha

Okay, I wasn’t just playing a prank on you (although it would be pretty hilarious if I just used this platform to troll you every once in a while, I suppose). I also wanted to illustrate a point: sometimes we make things harder because we expect them to be hard.

Nothing in my initial instruction explicitly said that the task was going to be difficult, but the context and phrasing certainly implied that I was asking you to do something that would have a surprising challenge buried within. And so you automatically prepared yourself for that challenge, which included doing things inefficiently!

Some things, occasionally, will be easy – for you. They might be very difficult for other people and so the context of the task assumes difficulty. But be confident in your own abilities. Know what you can do well. And when you’re asked to do such a thing, just do it – don’t make it weird.

The best way to improve at something is to make sure that in small, incremental, and consistent ways you are punished for your mistakes.

You don’t want to be in a situation where you lose a hand for every mistake. You probably won’t lose a hand; instead, you’ll probably be so safe you never learn anything. But you also don’t want to be in a situation where there are no repercussions for your actions at all; in such an environment, no rigor equals no vigor.

But if you get a small amount of negative feedback very regularly whenever you make a tactical error, that will hone the relevant talent or skill to a razor’s edge.

This is what I’ve always loved about the sales profession and the people who take it seriously. If you’re in sales, you’re getting that feedback multiple times per day. Make some minor tweaks to your technique and you’ll get hard data back almost immediately. This enables you to refine and iterate so incrementally that it becomes one continuous process.

With that method, risk becomes virtually non-existent. You don’t have enough to lose from any one decision to be afraid of it, so you have tremendous operational freedom. If you embrace the feedback and dedicate yourself to absorbing the lessons, you can try almost anything and find the very best version.

You can – and should! – look for ways to add feedback loops like this to anything you’re serious about. Taking measurements more frequently, soliciting customer feedback more often, or finding ways to place small bets on sub-tasks with short time horizons are all good ideas. But there’s a secondary lesson here as well: don’t let yourself get put in a position where these things are difficult or even impossible.

A sure way to have your skills atrophy or your intellectual rigor deteriorate is to let yourself fall into an environment where there is infrequent or even no feedback. If you’re in a job that allows you to work for a year before anything you do is evaluated that can sound like a dream… at first. But it turns into a nightmare when you discover that your work’s been terrible for a year and you have no idea why or how to fix it.

And maybe one more lesson – before you trust or believe anything someone says, do a quick check of their environment. Do they get any feedback when they’re wrong? Are they punished? Do they lose bets? If the answer is no, then a massive grain of salt applies!

Sometimes, you will find yourself in a miserable situation. It happens. Some of those times, there will be other people in the same situation who are genuinely good folks, and who are suffering right alongside you. While it’s nice to have some commiseration, there’s a dangerous element at play here.

Namely: hopefully you will escape that situation. Ideally, you’ll assert your personal agency very quickly and work to extract yourself. Some miserable situations are sticky, but most are far less sticky than people realize. But when people do realize that their chains are largely imaginary, they don’t always do so at the same speed.

So you may be the first to realize that you can just quit that terrible job, but then you may feel as though somehow you’re doing something bad to the people who haven’t yet realized the same. You’re leaving them behind, escaping when they “can’t.” It can feel like you’re practically stepping over their body to climb out of the pit, even though you’re doing no such thing. The person might lament – and truly believe – that you’re actually doing something to make their situation worse by leaving. After all, they’re losing a friend on the inside while you’re off to greener pastures!

First, remember: you aren’t.

They are as free to leave as you are, and your example may be exactly what they need. Whether it’s inspiration or just proof that it can be done, they need to see you leave as much as you need to leave yourself. And if you cave to the guilt, you’ve built the trap yourself.

If you have to, push them out in front of you or drag them along behind. If you care about them enough to chain yourself to them, make sure you’re dragging them up and not the other way around.

Be free together or be free alone, but don’t choose misery when you don’t have to. For anyone.

Here’s a productivity hack for you:

When you get a new project or assignment or whatever, immediately create all the relevant files. For instance, let’s say you’ve got a school project coming up where you have to write a five-thousand-word essay on the Industrial Revolution, complete with a reference page of at least five cited sources. This project is due in six weeks.

Today, the very instant you get this assignment, do the following: create a file folder labeled “Industrial Revolution Term Paper 2023.” Within that folder, create a doc labeled “IR Paper Rough Draft,” one labeled “IR Paper Notes,” one labeled “IR Paper Finished Copy,” and one labeled “IR Paper Reference Page.”

That’s it. You’re now, in all seriousness, like 25% of the way to the end. You have a place to drop ideas. A physical manifestation of “having more than absolutely nothing done.” You have a folder to drop links and reference files into. You have a little icon on your desktop or in your notes app that reminds you to think about that project. Instead of being a looming obelisk that you have to tackle, it’s now a thing that you’ve already started.

This will do wonders for how you view that project and thus create a sense of psychological safety around thinking about it. It will be easier – even fun! – to engage with. You can do this with any project in the world. Even if the project is “build a new bookshelf,” you can first just label a big box with “Bookshelf Stuff” and put some tools in there. Then when you get some wood, put it in there. But the box gives you a space – both physically and conceptually – to corral the project. To make it both real and controlled.

If you do this the second you get each project, you’ll also maintain a better sense of how many projects you have going on at the same time, and thus have better control over your bandwidth.

Try it. Watch the projects fly.

This past weekend, I took an extended backpacking trip that I’ve been planning for some time. I made all the arrangements, carefully planned my route, even pre-scheduled a few posts here on The Opportunity Machine (gasp, I know). I planned everything down to the last, most minute detail.

Hahahahahahaha.

A few things to remember about me. Even though I take these trips often and don’t consider myself a novice, I’m still what my father would call a “city-slicker.” I’m self-taught in the ways of the woods, I don’t have any formal training or even real skill. I’ve read a lot of books, watched a lot of videos, and gotten a lot of real-world practice – but that leaves plenty of room to mess up.

In particular, this time I was headed to a totally new area that I’d never camped in before. Knowing in advance that cell service was likely to be non-existent, I bought a genuine paper map and marked out my route in advance. At this point it’s important to note that reading a paper map isn’t like, an automatic thing that everyone can do without any practice or prior experience. But hey, how hard could it be, right?

Hahahahahahahaha.

So anyway, up I go! This is terrain that’s very different from the relatively easy foothills of central Pennsylvania where I typically go, This was in Virginia, where some very real mountains (by east-of-the-Mississippi standards, anyway) exist. And I was going to climb one. Then, from that point, I had a whole route planned through the rest of the backcountry and on to my destination.

The climb was hard. Really hard. It wasn’t just an “uphill hike.” At various points I was genuinely climbing, which I hadn’t really expected but was very excited about. The trek was arduous and difficult, but deeply satisfying. It started to rain – but it rains in PA too, and I was prepared for that. Higher and higher I went, until at long last I reached the top. With a great shout of triumph I dropped my gear and settled in to eat something and check my bearings for the next leg.

It was completely overcast due to the rain, and the trek was hardly a straight line, so I had to reorient myself a bit at the top. And at first, I couldn’t make sense of my location – something wasn’t quite lining up on the map, shouldn’t there be a path headed this way? And why was my compass saying that I’d just come from north, instead of south? And then, with dawning horror, I realized that I

had climbed

the wrong

damned

mountain.

Hahahahahahahaha.

As is my way, I laughed for probably thirty minutes straight. What else is there to do, at the peak of the wrong mountain?

So, I ate my lunch, packed up my gear, and picked a new route. From there, I saw beautiful waterfalls, wonderful wildlife, and incredible sights of all kinds. Over the next day and a half the weather brightened and I found myself exploring all manner of gorgeous trails. If it had been the trip I’d planned, it would have been a flawless trip.

Which means, of course, that it was a flawless trip. Sure, I learned that I’m rubbish at reading maps. But so what? This was the purest example of “it’s not the destination, it’s the journey.” There wasn’t anywhere specific I was really trying to be, just a walkabout that I really wanted to take. I feel absolutely fantastic, like a new man. I got everything I wanted from the experience: challenge, adventure, distance, spiritual solace, and emotional cleansing.

It turns out, you can’t really climb the wrong mountain, because there is no wrong mountain. There is only the climb, and the view from the top.

Neither energy nor matter can be destroyed; only changed.

Spirit, too.

You may feel beaten, pushed, defeated. But that is the winding of a great spring. Each moment you feel this way is water being pumped into a great tower, ready to flood down again. It may be transferred – for some, the great spring winds but their time on this Earth ends before it can spring forth anew. But that story will ignite a spark in some witness – perhaps immediately, perhaps a hundred years hence – and the energy will rush forth in that new vessel.

The human spirit cannot be destroyed. Only changed.

Today, I am in the forest. I’m doing something I almost never do, which is pre-schedule this post. But I’ve arranged a trip into the woods and will not be anywhere near anything I could post this from. Does it still count as my daily engagement?

Well, I make the rules, so I say it does. My brain will be elsewhere, carried by weary legs, charging a weary soul. As energy flows from my bones to my spirit, may you find yourself weary in all the right ways yourself.