The First Step to Doing Great Work
'How to Do Great Work' Pt. 1
This newsletter project began 43 essays ago - in the summer of 2023 - because I had a hunch that people weren’t doing so well. We had just emerged (or seemingly emerged) out of the confusion and hostility of the COVID19 pandemic, and something felt wrong - we just couldn’t say what, exactly. Many believed - as I’m certain I do now - that the pandemic was not so much a diversion of the course of the times, but an accelerator.
What had been bubbling below the surface in our part of the world, like a cultural simmering pot, was unease, tech addiction, loneliness, poor sleep, bad nutrition, and a disconnection from people, place, and work that was hard to describe, but ever present.
The great and powerful Paul Kingsnorth recently had a crack at summarizing this cultural malaise with his new book Against the Machine1. Paul argues that the machine is something that can’t be stopped, partly because we can hardly articulate what it is, and partly because it is comprised of us, and there is no stopping us.
We make things - as many things as we can make - and once we’re on the make-stuff train it’s damn near impossible to get off. Perhaps this is perfectly human. Perhaps it’s something different now and we’re on a rather slippery slope2.
Every November I study military history - and this year it’s Barbara Tuchman’s The Guns of August. It’s largely about the first days of August that led to WWI, and it’s message is something to the effect of what Kingsnorth thinks of the Machine. Once we’re on that train, we’re on it forever pal. We’re on it until it’s logical conclusion is concluded, and we may not like that conclusion one bit. Human cultures become path-dependent and we can’t stop ourselves.
For Paul - what us moderns are missing is the Four Ps:
People
Place
Prayer
The Past
I’ve spent the balance of this newsletter dealing with the first two, and I believe in our human need for them both so much that the bloody thing is named after them - People & Place.
We need people because we’re pack animals and being alone is no good for us. It might even be the worst thing that can happen to us and we’re paying the piper on that front right now.
We need place because we quite literally come from it and we remember that somehow. When someone cries Vive la France! or hears a bagpipe march, what stirs in us is love of…what exactly? The land. It’s what the Americans feel about the vastness of the West, what the Greeks feel of their islands, what the East Africans feel about the rolling hills and red soil, and what the Australians feel about the Great Barrier Reef and the Outback. Although ours pails in comparison to the connection that the ancients had with the land, we remember it in our bones, if not in our brains.
I’ve even dealt with Paul’s third and fourth on the list - prayer as a metaphor for believing in something larger than ourselves (which we clearly don’t3) and our connection to a past that allows us to say “I am this, and it is good to be this” (which we also clearly don’t have).
The one I would add as my third, which Paul may have left out because it breaks the satisfying pull of alliteration, is work - something that I believe is a critical missing piece of the puzzle here. Not work as in your job - that you may or may not find completely meaningless (which is a problem in and of itself), but work as in the very human thing you ought to be doing and you know you ought to be doing but you don’t know how you know or how to do it.
The closest I’ve come to understanding this process fully is a combination of the macro-framework that Robert Greene gave us in Mastery, the micro-framework of Kevin Kelly’s 1,000 True Fans, and Paul Graham’s essay - How to Do Great Work. I’d like to deal with the latter this week. As you can probably tell from the title, Paul is rather good at getting to the point.
Let’s revisit How to Do Great Work in the hopes that you do your best work ever in 2026. Not the work you think you should do for social gain or more treasure, but because it’s your work.
This will be Pt. 1 of a series that goes as long as it goes. Please enjoy, and thank you for reading.
“Know your truth, stick to the process, and be free of the outcome.” - Boyd Varty
Your Gifts x Your Interests
I started this Substack as an attempt to get really good at writing. Specifically the essay format - in the hopes that a collection of good essays would eventually turn in to a good book. I didn’t start with the reader in mind, which may be a traffic and attention mistake, but with the simple acknowledgement that you are what you repeatedly do and if what I am is a writer, then I best get writing.
I didn’t worry - and still don’t worry - about what comes back because what comes back isn’t the point. The point, so far, is to get really good at writing. At writing essays. My essays. Not the essays that people expect or that might do well, or might check the to-do-list boxes of virality, but the essays that I am supposed to write and that I alone can write.
Essays that would please my younger self, as he awkwardly and rather emotionally made his way through the world - enthralled by lists, books, maps, and artefacts of all kinds. It’s in this past - the history of you - that Robert Greene, Kevin Kelly, and Paul Graham begin their quest in helping you do your life’s work.
“The first step is to decide what to work on.” - Paul Graham
This might seem obvious in principle, but it isn’t in practice. In fact it’s rather hard because you have to shed the world’s expectations of you, and those can be a great weight indeed.
“The work you choose to do needs to have three qualities: it has to be something you have a natural aptitude for, that you have a deep interest in, and that offers scope to do great work.”
I think the first two are actually far more important than the third because we all have a limited number of gifts. Those who are seemingly good at everything do exist, but they are exceedingly rare. For most of us - Nature or God, or whatever you recognize as more powerful than yourself, gave us one, maybe two, sacred gifts. The things that chose you and make you tremble with terror because you know they are your gifts, and you have no choice in the matter, and you ought to use them. The things that if you don’t use make us unwell somehow.
For me it’s writing and connecting with people at the individual level. Two gifts. That’s exit. That’s all I was given and it’s within that simple framework that I find my life’s task.
Until I learned how to harness my gifts productively, these manifested as far too much thinking, and an empathy problem that I couldn’t handle. Not knowing what to do with your gifts is part of the process, and this doesn’t make you weird or behind. It’s perfectly natural and it is up to you to find out how to deploy them in your life. The framework I’ve learned is Learn Life - Yes Life - No Life - Teach Life.
The next job to be done is combine your gifts with something you’re deeply curious about. This is the only way to do great work because if you don’t really care about doing it you won’t do it to it’s fullest extent. You just won’t. As soon as it gets hard you will quit.
This is also very hard to do because you will inevitably find yourself pulled in many directions, fulfilling other peoples to-do-lists, not your own. This is even more tempting when money becomes involved. You must ignore this (temporarily), and if you’re already on that path, find the nearest reasonable exit that maintains the relationships you’ve made and points you back toward True North. Money is a by-product of great work, so maximizing for learning, relationships, and ability is far more important when you’re young.
The third piece of advice here is find something that offers you the opportunity to do something great. It’s good advice but it might be redundant in the modern world. There are 8 billion of us now, someone is interested in everything, the 1,000 True Fans model is readily available and works (although it isn’t easy) and if you combine the natural abilities that Nature gave you, with something you’re deeply curious about, then you can’t help but make it great. It’s essentially a fait-accomplit if you do the first two correctly.
“If you’re not sure what to work on, guess. But pick something and get going.”
This is probably the most underrated advice of all, and it’s on the first page of the essay. Starting is the difference between doing something great and doing nothing at all. As long as you’ve got air in your lungs and sunrise brings another day above ground, you’ve got a shot at doing your work.
Start right now. Stack that work over time - meaning that you should at least be rowing in the same general direction at all times. That way the work has a chance at compounding and compounding is somehow miraculous. You will discover this quickly. Not over night, but it will come if you stay on the bus.
Push to the Frontier (velocity > speed)
I work with young companies - startup companies - and in these good people there is a bent towards speed. Startups do have a speed advantage - and if you’re going to capture a new and exciting opportunity you need to move fast, but speed is not as important as velocity. As Ryan Petersen recently told Harry Stebbings - velocity has a vector - what matters most is speed in the right direction.
Once you’ve started doing your work, you need velocity.
“…the next step is to learn enough about it to get you to one of the frontiers of knowledge.”
There is an infinite amount of interesting things to be done, on this particularly interesting planet. We start with principles - some foundational knowledge set, and then we push through the jungle, like the back and forth of a mental machete, to find something compelling and to discover a sense of mastery that only comes through years on the path.
More often than not this starts in the form of a question - then several questions - until the onion has been properly peeled. Time is a central component4. Most moderns see time as something to overcome or something to get through. This is naive and misses that time is a central ingredient to doing anything good. It’s literally part of the recipe, and steps are not to be skipped5.
“It may not be possible to prove that you have to work hard to do great things, but the empirical evidence is on the scale of the evidence of mortality.”
If you don’t skip steps you notice important things that others missed. These often become obvious in hindsight, but they only get revealed by the persistent few who are willing to descend layer upon layer. You can’t know what work is supposed to be done without doing it, and so reps become critical. It’s the choosing bit that is the hard part.
How to Know You Know
It occurred to me in recent years - in the way that some of us are prone to epiphany, that maybe the most important part of this whole deal is the choosing of the thing. Ironically, we moderns are so out of touch with our own selves that we somehow don’t know that we know we know what to do.
On some level we know what we’re supposed to do, we just can’t seem to bring ourselves to ignore the noise and do it. It is critical that we regain this sensory ability to feel what is right, outside of rational logic because the feeling brain is much more powerful than the thinking brain.
The thinking brain is especially insidious for ‘smart’ people - or people who are perceived as smart - because the thinking brain takes over and you talk yourself into silly things. Those who are more in touch with the human principles of the feeling brain - refined for hundreds-of-thousands-of-years of evolution - are able to achieve a level of common sense that the former cannot. What Taleb calls IYIs - intellectuals, yet idiots.
Getting in touch with the feeling brain is critical because only you can know what to work on, and only you can choose it.
“…when it comes to figuring out what to work on, you’re on your own.”
The good news is this might be the time in human history where the term work means the most things. In the 1,000 True Fans era, someone is interested in everything, and there are so many of us on earth that if 1 person is interested, there are likely 999 more that are too. Work - if you’re not out there doing the admirable work of tangible things like building roads or maintaining power lines, simply means the exchange of goods and services between people who have those things and people who want them.
Instinct is key to knowing how we know. Acting on an instinct - even the smallest instinct - is a really good place to start because as Graham tells us ‘…you need to make yourself a big target for luck, and the way to do that is to be curious. Try lots of things, meet lots of people, read ots of books, ask lots of questions.’
As doubt and imposter syndrome creep in, control for curiosity and interestingness. Follow the thing that lights you up like a Christmas tree, regardless of how much it pays or doesn’t pay. Why this is true is simply because it’s obvious. Our need for facts and data is useless in this arena. There are things we know we know, and that’s just the fact of the matter.
The ski patrol making $22/hour on the mountain is in a far better position than the desk jocky whose life force is being sucked minute by minute for $34/hour. Do the math! The push is $12/hour more and the sense of stability that comes from a do-nothing function at a large company. The pull is low energy, low libido, being uninteresting, sitting all day under neon lights, and the slow decline into becoming a hunched over screen-demon. I’m sorry for being harsh here but this the reality and our physical, emotional, and spiritual health crisis are clear for all to see. It’s written in our blood-shot eyeballs and our online rage.
We’re not fulfilled because we’re not doing our life’s work. We’re making what other people think we ought to make and at some level this makes everything worse.
“Instead of making what they want, they try to make what some imaginary, more sophisticated audience wants. And once you go down that route, you’re lost…if you stick to what you find genuinely interesting, you’ll be proof against all of them. If you’re interested, you’re not astray.”
In a sick culture, curiosity and the appetite for work is some kind of life-arbitrage that makes you increasingly unique. If we can’t tap into our physical senses, and if we lose touch with our physical bodies, we can’t decide what to work on, and we don’t have the stomach to pursue it.
Pursuing it means that you have the discipline to work on it every day, regardless of your state of motivation. For writers, this means writing 1,000 words per day, every day, instead of writing 10,000 words whenever you feel inspired to do so. On a long enough time horizon the former ends up with books and the latter ends up with half-baked ideas that never get published.
If you’re lucky, the discipline of doing a small amount of great work every day compounds into something no-less than a miracle with enough time.
Discipline is some sort of divine freedom - that’s part 2.
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All we need is a point of view, a set of tools, and a lot of time.
See you on the road.
The subtitle of the book is On the Unmaking of Humanity and that struck me as a rather good title. https://www.goodreads.com/book/show/222925312-against-the-machine
And as Naval reminds us - the slippery slope fallacy isn’t a fallacy, we just haven’t thought it through.
Still the most read thing I’ve ever written. That’s a cultural clue to how we’re really feeling about our times.
I wrote a 3-part series on this - inspire by my late maternal grandmother. Start here.
Interestingly - the Chinese know this and that cultural ethic leads to extremely capable people.