Feedback Loops

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!

Misery’s Company

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.

Label the Box

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.

The Wrong Mountain

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.


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?


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




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.

The Law of Conservation of Spirit

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.

Make Weary My Bones

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.


What’s the difference between conviction and desperation?

What are the things you can do when your back is to the wall and you have no choice? You may have a deep well of untapped energy in those moments, but the deployment of it will be hard to guide. Stress and fear will bend your vision. Sure, adrenaline can make you strong, but it can’t make you smart.

Conviction is the deep wellspring of the spirit. The things you can do not because you have no choice due to outside circumstances, but the things you can do because you have no choice due to what your soul will not abide.

If you are in touch with your conviction, desperation becomes far less likely. Conviction can be cultivated and summoned, and belongs only to those who have something to believe in. Honor in your heart and nobility of purpose will give you that well; the ignoble and the dishonorable can only ever be desperate.

Three of a Kind

There’s a lot of power in triangulation. Getting three examples of anything starts to show the actual topography of the category to which they belong.

Pick a style of music you’ve never listened to before. If you listen to one song of that genre, you still don’t know much about the genre. You have no way of knowing whether the song you listened to was representative of the whole category or not. Listen to a second song, and maybe it’s wildly different from the first. Maybe you love one and hate the other. How do you know if you like the genre or not?

You listen to a third. Now you start to see patterns and similarities. You start to see how it more closely resembles one of the first two more than the other. You start to get a little triangulation going and can safely start to form your initial hypothesis.

It’s not perfect, but it’s leagues better than zero, one, or two examples as far as extrapolation goes.

When you want to work on a project, start with three data points. Three examples, three bits of research. Heck, take three bites of something before you decide if you like it, just like the kids have to. Fail at something three times before you try to guess why you failed. Read three job descriptions from different companies before deciding if that kind of role is worth exploring.

There is a lot of information in the spaces between your set of three – often more information than is contained in the examples themselves.

In Vulnerability

In my work, I get a version of this question very frequently:

“How do I ask for the thing I want without it seeming like that’s what I’m doing?”

In other words, people often want to be very cagey. They want to hide their motivations and shield their true intentions. And I must emphasize that they want to do this with intentions that are actually very pure and even noble. I don’t coach like, drug dealers or whatever.

I understand, of course. People don’t want to be vulnerable, and they equate “vulnerability” with other people knowing too much about them. But in that particular kind of “vulnerability,” there’s a ton of strength, value, and success.

There’s also toughness. You’re not really vulnerable at all just because you’re honest with someone about the fact that (for example) you want to start a non-profit to help teens find writing mentors or whatever and you don’t have any idea how to begin. It feels vulnerable to say that because in our modern lives, we’ve come to equate “awkward” with “vulnerable” and equate “unfamiliar” with “awkward.”

It’s only unfamiliar. And that’s most of life. All the things you want are unfamiliar. Of course they are; you don’t have them yet.

You aren’t vulnerable in the unfamiliar. You’re unassailable in your purpose. Honesty is your armor, ambition is your shield. Nothing can harm you for wearing more of it.

The Familiar Fridge

Do you know why you open the fridge when you’re hungry, see that there’s nothing there, and then open the door again five minutes later?

If you look statistically at all the times you’ve been hungry in the last few years, the majority of the solutions were found inside that fridge. So that’s your default. It’s familiar. Opening the door again doesn’t solve the problem this time, but it feels good. It feels right. So you keep doing it.

When we’re scared, stressed, or uncertain we default to the familiar. We do the things we’ve always done. We solve the problems we know how to solve, even if that isn’t the problem we currently have. But solving any kind of problem feels good in the same way opening the refrigerator door feels good.

When you want to solve a problem, you have to get uncomfortable. You have to do things that, at first, might not feel good – because they’re unfamiliar. As you navigate them, they’ll become easier, and problems will get solved. But the solutions aren’t where you were to begin with, or you wouldn’t have had the problems.

You’re hungry because that fridge is empty. Now you have to go somewhere else.