Background Ops #2: Keystone


“… unless the rate at which social antibodies evolve can increase to match the accelerating rate at which technological progress throws off new addictions, we’ll be increasingly unable to rely on customs to protect us. Unless we want to be canaries in the coal mine of each new addiction — the people whose sad example becomes a lesson to future generations — we’ll have to figure out for ourselves what to avoid and how. It will actually become a reasonable strategy (or a more reasonable strategy) to suspect everything new.

In fact, even that won’t be enough. We’ll have to worry not just about new things, but also about existing things becoming more addictive. That’s what bit me. I’ve avoided most addictions, but the Internet got me because it became addictive while I was using it.”

— Paul Graham, The Acceleration of Addictiveness, 2010



“In my messenger days the old Pittsburgh Theater was in its glory under the charge of Mr. Foster. His telegraphic business was done free, and the telegraph operators were given free admission to the theater in return. This privilege extended in some degree also to the messengers, who, I fear, sometimes withheld telegrams that arrived for him in the late afternoon until they could be presented at the door of the theater in the evening, with the timid request that the messenger might be allowed to slip upstairs to the second tier — a request which was always granted. The boys exchanged duties to give each the coveted entrance in turn.

In this way I became acquainted with the world that lay behind the green curtain. The plays, generally, were of the spectacular order; without much literary merit, but well calculated to dazzle the eye of a youth of fifteen. Not only had I never seen anything so grand, but I had never seen anything of the kind. I had never been in a theater, or even a concert room, or seen any form of public amusement. It was much the same with “Davy” McCargo, “Harry” Oliver, and “Bob” Pitcairn. We all fell under the fascination of the footlights, and every opportunity to attend the theater was eagerly embraced.”

— Andrew Carnegie, The Autobiography of Andrew Carnegie, 1920



This is the second issue of our series on Background Operations. In Background Ops #1: Strict Limit, we meditated some on an observation of Sir Alfred North Whitehead –

“Civilization advances by extending the number of important operations which we can perform without thinking about them.”

In this issue, I’ll propose something that might sound a little dramatic, but I’ll walk you through all my reasoning first and foremost — and you can see if you agree.

My premise is this –

People who have both a complex life and who don’t have an “ops keystone” are going to regularly and reliably suffer unnecessary stress, misery, backsliding, problems, lack of reliable growth, and suppressed thriving.

Well, that sounds ugly, eh?

We’ll get deeper into what an Ops Keystone is — the short version is that it’s anything, no matter how simple, that you look at regularly to ensure you’re on track with everything that matters in your life.

But before we get into the medicine, we need to diagnose the problem.

The problem is this –

Outside of people who are naturally hyper-organized, or who join an organization that sets up one’s environment for them to ensure they’re on top of things such as the military, it’s very common for people to find a terrific behavior that leads to health, well-being, productivity, thriving, and a better life… and then to simply stop doing it.

For no particularly good reason.

You must have seen this dozens if not hundreds of times across your life — perhaps in yourself, and if not, certainly in others. I think it — no exaggeration — one of the largest problems plaguing people in complex modern lives.

So let’s analyze the root cause of that, and then look at what tools and processes we can use to overcome it — so all the smart, healthy, productive, life-affirming behaviors we want in our lives actually stick.



Andrew Carnegie’s life is certainly worthy of study — but not just for the obvious reasons.

Obviously, his life has attracted a lot of attention for his prowess in business — he became the wealthiest man in the world in 1901 — and for his work in philanthropy, building libraries, and for advocacy in working towards modern international law and world peace.

These are, of course, good reasons to learn from his life — but there’s another arc that’s particularly relevant to those of us living in the 2010’s.

Carnegie’s lifespan saw arguably the biggest transformation of the world of all-time. He describes being born in the attic of a small one-story house, “of poor but honest parents, of good kith and kin” — in a small crafts town going through an economic downturn.

This story is familiar enough — but through most of human history, chance would largely govern the final outcome. Prosperity would rise and fall across generations, as a mix of small discoveries and random forces raised some tides and lowered others.

But it went differently for Carnegie — his mother was able to borrow money to allow the young family to immigrate to the United States in 1848 when Carnegie was 13 years old, and he grew up in an age where the advances of technology led to ever more technology, more wealth, and more prosperity.

Carnegie described his birth –

“To begin, then, I was born in Dunfermline, in the attic of the small one-story house, corner of Moodie Street and Priory Lane, on the 25th of November, 1835, and, as the saying is, “of poor but honest parents, of good kith and kin.” Dunfermline had long been noted as the center of the damask trade in Scotland.”

And immigrating –

“With the introduction and improvement of steam machinery, trade grew worse and worse in Dunfermline for the small manufacturers, and at last a letter was written to my mother’s two sisters in Pittsburgh stating that the idea of our going to them was seriously entertained — not, as I remember hearing my parents say, to benefit their own condition, but for the sake of their two young sons. Satisfactory letters were received in reply. The decision was taken to sell the looms and furniture by auction. And my father’s sweet voice sang often to mother, brother, and me:

“To the West, to the West, to the land of the free,
Where the mighty Missouri rolls down to the sea;
Where a man is a man even though he must toil
And the poorest may gather the fruits of the soil.”

The proceeds of the sale were most disappointing. The looms brought hardly anything, and the result was that twenty pounds more were needed to enable the family to pay passage to America.”

They had to borrow the rest of the money to immigrate.

Already the story is interesting and illustrative of a unique time in history. 
 But what was really striking to me, reading Carnegie’s Autobiography, was just how new everything was at the time. The ability to send notes via electric telegraph was only commercialized at scale in the 1840’s, and one year after arriving in the New World, the 14-year-old Carnegie started working for the Ohio Telegraph Company in 1849.

This lead us to a most striking quote about Carnegie’s younger life –

“In my messenger days the old Pittsburgh Theater was in its glory under the charge of Mr. Foster. His telegraphic business was done free, and the telegraph operators were given free admission to the theater in return. […] In this way I became acquainted with the world that lay behind the green curtain. The plays, generally, were of the spectacular order; without much literary merit, but well calculated to dazzle the eye of a youth of fifteen. Not only had I never seen anything so grand, but I had never seen anything of the kind. I had never been in a theater, or even a concert room, or seen any form of public amusement.



This is where I would like you to stop — to pause a brief moment — and to think about the bearing on your own life.

Andrew Carnegie, at 14 years old, had never seen any form of public amusement.

Television, of course, had not been invented.

Movies had not been invented.

Radio had not been invented.

The Internet, obviously, had not been invented.

Carnegie came across popular entertainment for the first time in his at age 14.

Is this not striking? Is this not strange? Is this not incredibly alien to us in 2017?

I have said that Carnegie’s life is worth studying because he lived through one of the most momentous periods of all-time. During his life, slavery was abolished around the world, the shape of modern employment emerged, large mass industrial production was invented, and the world became stitched together through steam power, oil and gasoline, the telegraph, railroads, and water travel.

But additionally — his was the first era where entertainment and amusement started to become commonly available.

For all of human history, this had not been so — outside of the rare few people who lived in one of the great capitals like Rome, Tenochtitlan, Vienna, Istanbul, London.

I believe we’re living in an era much like Carnegie’s — with all its perhaps-infinite opportunities for personal growth and development, and all the commensurate downsides that come with the onrush of so much infinite newness.



Paul Graham is no doubt one of the finest essayists of our age — I imagine you’re already well-familiar with his writings; if not, you ought to read just about everything he’s written.

He penned The Acceleration of Addictiveness 7 years ago, in 2010. It was short and to the point — and the point stuck with me ever since –

“As far as I know there’s no word for something we like too much. The closest is the colloquial sense of “addictive.” That usage has become increasingly common during my lifetime. And it’s clear why: there are an increasing number of things we need it for. At the extreme end of the spectrum are crack and meth. Food has been transformed by a combination of factory farming and innovations in food processing into something with way more immediate bang for the buck, and you can see the results in any town in America. Checkers and solitaire have been replaced by World of Warcraft and FarmVille. TV has become much more engaging, and even so it can’t compete with Facebook.

The world is more addictive than it was 40 years ago. And unless the forms of technological progress that produced these things are subject to different laws than technological progress in general, the world will get more addictive in the next 40 years than it did in the last 40.”



Carnegie –

“A messenger boy in those days had many pleasures. There were wholesale fruit stores, where a pocketful of apples was sometimes to be had for the prompt delivery of a message; bakers’ and confectioners’ shops, where sweet cakes were sometimes given to him. He met with very kind men, to whom he looked up with respect; they spoke a pleasant word and complimented him on his promptness, perhaps asked him to deliver a message on the way back to the office. I do not know a situation in which a boy is more apt to attract attention, which is all a really clever boy requires in order to rise. Wise men are always looking out for clever boys.

One great excitement of this life was the extra charge of ten cents which we were permitted to collect for messages delivered beyond a certain limit. These “dime messages,” as might be expected, were anxiously watched, and quarrels arose among us as to the right of delivery. In some cases it was alleged boys had now and then taken a dime message out of turn. This was the only cause of serious trouble among us. By way of settlement I proposed that we should “pool” these messages and divide the cash equally at the end of each week. I was appointed treasurer. Peace and good-humor reigned ever afterwards. This pooling of extra earnings not being intended to create artificial prices was really cooperation. It was my first essay in financial organization.

The boys considered that they had a perfect right to spend these dividends, and the adjoining confectioner’s shop had running accounts with most of them. The accounts were sometimes greatly overdrawn. The treasurer had accordingly to notify the confectioner, which he did in due form, that he would not be responsible for any debts contracted by the too hungry and greedy boys. Robert Pitcairn was the worst offender of all, apparently having not only one sweet tooth, but all his teeth of that character. He explained to me confidentially one day, when I scolded him, that he had live things in his stomach that gnawed his insides until fed upon sweets.”

Don’t those lines seem perfectly quaint now, looking backwards?

A messenger boy in those days had many pleasures. There were wholesale fruit stores…

Many pleasures — wholesale fruit stores! What a different world from our own!

But the young Carnegie didn’t indulge in sweets and fruit as much as the other boys, and he was ostracized a little for it –

“I was also taxed with being penurious in my habits — mean, as the boys had it. I did not spend my extra dimes, but they knew not the reason. Every penny that I could save I knew was needed at home. My parents were wise and nothing was withheld from me. I knew every week the receipts of each of the three who were working — my father, my mother, and myself. I also knew all the expenditures. We consulted upon the additions that could be made to our scanty stock of furniture and clothing and every new small article obtained was a source of joy. There never was a family more united.

Day by day, as mother could spare a silver half-dollar, it was carefully placed in a stocking and hid until two hundred were gathered, when I obtained a draft to repay the twenty pounds so generously lent [to immigrate to America] to us by her friend Mrs. Henderson. That was a day we celebrated. The Carnegie family was free from debt. Oh, the happiness of that day! The debt was, indeed, discharged, but the debt of gratitude remains that never can be paid.”

Right there — right there, those single dimes — became the foundation of Carnegie’s wealth. He looked to save everything. He had his sights on larger and more intellectual pleasures than sweet cakes.

At first, he was saving so that his family could pay off the generous loan given to them to immigrate to America — but afterwards, he kept saving. Before he was 20 years old, Carnegie and his family had already started to buy both stocks and property.

This applies, of course, not just to money management — but to time, attention, effort, and exertion. Any rapid expansion of technological progress creates infinitely many new and varied ways to pour one’s efforts into immediate pleasure and enjoyment — or alternatively, to defer those pleasures and make investments to rise in the world.



One last point of reference before we get into Operations.

The internet community Reddit is a fascinating place — I’ve personally watched it go from one of the most intellectual places on the internet in its earliest days, to (in my opinion) a decline into silly entertainment and frivolity for a number of years, but later with many sub-communities emerging that are profoundly supportive of each other in exploring important ideas and bettering one’s life.

The most interesting communities on Reddit, to me, are the ones that work to help their members quit and get over behavior that’s not serving them well. That’s what Reddit’s /r/stopgaming community aims to do, for people who feel like they’ve become addicted to video games and for whom playing games has become a negative force in their life.

There was a comment I read on there that resonated. I couldn’t find the exact comment when I looked for it to cite it, but it was something like,

“You don’t get any points, awards, or achievements for doing your chores. You don’t level up. You can’t ‘grind it’ and feel like you’re making progress.”



Here is our problem, then –

(1) Technology is growing immensely.

(2) This is creating immensely many opportunities to engage in new and different behaviors that ever existed.

(3) Some of these behaviors are incredibly addicting.

(4) Many healthy, smart, sane classical behaviors — basic health, well-being, cleanliness, sharpening one’s mind, learning, saving money, developing good habits, getting better at creating things — are less addictive and have a worse feedback loop than easier and faster consumption of entertainment and pleasures.

(5) If we don’t build processes, rules, tools, and systems to manage this, it’s easy for many of us to get swamped by these simple addicting pleasures — and neglect what would lead to a very thriving life.

Do you agree?



We are exploring Background Operations. It’s certainly possible to get any habit or good practice to stick by focusing paramountly on it and making it the primary goal for some time in one’s life.

But life is getting more complex all the time, and the more complex your life is, the less you can rely on keeping good habits and best practices in the forefront of your mind.

How does one stay on-track, then, with everything?

I have, I think, the general answer to this — you need a keystone for your operations.



It’s hard to sketch this concept in the appropriate gravity — to not make it any more or less of a “big deal” than it is.

One the one hand, it’s a really big deal. I assess it as one of the most common general root causes of failure in the modern world.

On the other hand, it’s fairly simple and straightforward.

Let’s just write it down plainly, then.

If your life is complex enough, then you need a single thing you can look at every day that points to everything else that matters to you.

I call that an “Ops Keystone.”

A single place you can reference to ensure all the operations (ongoing actions, processes, plans, projects, duties, obligations, goals, health, well-being, etc, etc) can be referenced simply and easily.

Some people do this in a high-tech way — and computers can help — but it doesn’t have to be technical at all.

A common keystone I see among old-school executives is a simple notebook where they write down on one side everything they need to do in a day, which they cross out things as they do them, and write down anything new that comes up that day at the bottom. Then they’ll re-write and re-prioritize on a new page of the notebook at the end of the day to run tomorrow.

This works very well for many people. There’s downsides to having it on paper instead of a computer — it’s harder to reference later and slightly harder to analyze — but that’s besides the point.

Any keystone can be sufficient. And having any keystone at all is so far superior to not having one that the form factor is, relatively, not very important.

The main point is that (1) you look at it daily, and (2) it points at everything else that matters. Paper is completely sufficient, again, if you look at it every day and it accurately points at everything you want to be paying attention to.

Some people use their calendars this way — scheduling every activity onto there that they want to do, including “appointments with themselves” to do fitness, learn something, or spend leisure time. This has never worked well for me personally — I like to only schedule external appointments on the calendar and let the rest of the time float — but I know many successful people using their calendar this way. If you can (1) look at the calendar daily, and (2) your calendar points at everything else that matters, then that would be a solid keystone. That form factor works well for some people and less well for others.

On a slightly more technical note, I see people setting up productivity apps like Omnifocus as a keystone. If you haven’t used it, Omnifocus is elegant software where you can write create projects and tasks, and have it generate to-do lists for you. The people that I see getting the most out of Omnifocus also use one of its power features where it can automatically generate new tasks in the future. You can set up Omnifocus to have a new “reconcile weekly expenses” task automatically be created every Friday and set “take the dog to the vet for a check-up” to auto-create every six months. If you then (1) looked at Omnifocus daily, and (2) ensured you wrote down all the things that mattered to you in there, it would work as a keystone.



For my part, I use a Lights Spreadsheet as my keystone — I’ve been using it basically nonstop since April 2013. That’s 186 weeks, and I used it basically every single week since then. (I missed a few weeks after surgery.)

In April 2013, I had just having completed a month on a whirlwind tour of speaking at around 15 top universities and tech spaces across different cities in the U.S. and Canada.

At the end of that intense run, my habits were a mess — I was eating whatever was around, not hitting the gym, my sleep and wake times were inconsistent, I wasn’t reliably working on what was important to me, I was writing only erratically… heck, some days I neither did important work nor took good leisure.

It had been a great run that previous month, but it was a bad state of affairs afterwards. Not maximal thriving, by any means.

I sat down at a hotel in Toronto and took out a sheet of paper and tried to figure out what I should be doing every day. After thinking for a couple hours, I had a list of around a dozen items — things like plan the next day in the evening, do a morning routine in the morning, spend significant time offline, take a walk, work on my most important project — and after thinking some more, I decided I’d try to do each of these activities every day.

I put them into a spreadsheet, and then I’d mark them with a green “Yes” if I did them, and a red “No” if I didn’t do them. Eventually I figured out some best practices around it, the biggest one that I’ll recommend to you being aiming for a 70% success rate weekly.

70% seems just about perfect. We know that failure is typically more demoralizing than success is encouraging for people, and 70% means more than two successes for every failure. But on the flipside, people who aim for 100% often get demoralized and go on binges or give up after one failure. Additionally, people who aim for 100% often set their goals and targets too low — by always aiming for 70%, I knew I’d constantly be at the edge of what’s possible for me and growing.

At the end of every week, if I succeeded much more than 70%, I increased the difficulty or added new things to do. So I might increase “Meditate 5 minutes per day” to 10 minutes, or add a new item I wanted to work on. That way, whenever I was succeeding and getting comfortable, I’d keep pushing myself.

On the flipside — and this can be hard for achiever-type people, we’re often stubbornly persistent — if I succeeded much less than 70%, I’d make things easier for next week. I’d turn “run 5 miles” into “lace up my running shoes and go outside” or I’d remove items from the list. I wouldn’t necessarily make adjustments after one bad week, but two weeks in a row below 70%, I’d always then make things easier to rebuild strength and momentum. It became a wonderful self-calibrating system to keep me always more succeeding than not, and always at the edge of my capabilities.

Lights became my ops keystone, my control center — whenever I had something new I wanted to make progress on, I’d create a Light for it. These could be related to mental and physical health — meditate, explicitly take downtime to recharge, nap, go for a run, bodyweight exercises, mobility exercises, meal planning and eating clean — or it could be work-related, like make a sales call, advance a particular project, work on an operations document. Whatever was relevant at the moment.

The important thing was, (1) I looked at it every day, and (2) it pointed at everything else that mattered to me.



There’s probably dozens if not hundreds of form factors you could use for a keystone. It doesn’t really matter which one you choose to use, so long as you actually use it and (1) you look at it daily, and (2) it points at everything else that matters.

And again, some people don’t need one — if your life is low in complexity and you’re broadly thriving and getting what you want, or if you’re in a profession like the military where the external environment naturally tilts towards you doing what’s important, then you might not need one.

But for the rest of us with complex lives where the environment doesn’t naturally manage our lives for us, I see this as one of the most important predictors of success — and the lack of one, a very reliable predictor of failure.

This leads to one last very important point, though — you actually have to install the thing and take it very seriously until it’s installed.

Use whatever form factor you like. Try a few different ones. Different things suit different people.

But once you pick one that you like, it might take a very serious and concentrated effort for a number of weeks until it becomes easy and automatic and habitual.

I’ve seen a lot of people start by looking to schedule their entire week onto the calendar, and then… just stop doing it. Start setting up Omnifocus, then… stop using it. Start organizing their life around Trello, and then… stop doing it.

For some people, building out and using a keystone is the most natural thing in the world — I’ve seen a lot of engineers and programmers, in particular, take to something like Lights or Omnifocus, install it once, and use it forever — and get all the gains. It tends to come very naturally to people with an engineering mindset.

For people without that mindset naturally — I’m one of them, actually — it’s even more beneficial, yet perhaps harder to install. This is the part that I can’t help with much — I don’t know how to make people do things that are good for them. If you install a keystone of any sort and look at it daily, it’ll help you manage and thrive across your whole life — but you have to actually take it very seriously and do it.



To summarize, our lives have become more complex with all the glories of the modern world and modern technology — and all the commensurate downsides that come along with it. Whereas Andrew Carnegie merely needed to resist buying sweet cakes for a dime to start building capital, we need to navigate a nearly-infinite and infinitely-varied set of addictive activities to focus on the types of things that’ll really lead to a maximally thriving life.

I believe the answer is you need an Ops Keystone. That’s something that, once installed, reduces all the complexity to simply looking at your keystone to ensure things are on-track.

I very much like, personally use, and highly recommend using a Lights Spreadsheet — thousands of people have gotten on it since I wrote about the concept a couple years ago, and I regularly get thank-you notes saying it was life-changing.

It’s particularly nice because checking a box green, as stupid as this might sound, is actually highly motivating and encouraging. It fights against that Reddit gamer’s observation,

You don’t get any points, awards, or achievements for doing your chores. You don’t level up. You can’t ‘grind it’ and feel like you’re making progress.”

On Lights, it’s wonderful to see green lights every day and being able to see how your consistency and successes are growing gradually week-over-week. It also helps with making adjustments if your current program is too easy or too difficult, by aiming for that 70% target rate.

But it doesn’t have to be Lights. I think it has to be something, for most people. As a last point of guidance, though, please keep it as simple as possible. It should take no more than 5–10 minutes per day to do the meta-work of updating your Lights or Omnifocus or calendar. If it gets substantially higher than that, it becomes like undesirable paperwork — it needs to be lightweight and simple enough that it’s not a chore to do.

It also needs to be simple enough to survive your worst week.

Bear those in mind.

If you want to get on Lights, Kai and I created a template version and a set of best practices, you’re welcome and invited to try it out.

But again, I don’t care if you get on Lights. It’s a great tool for me and helps me slot all the details of everyday life into a lightweight structure that’s motivating and builds consistency, while granting some good data to make adjustments every week — but a lot of people have success with paper, a calendar, Omnifocus, or whatever other software or method.

Just get on something. Take it very seriously when you do until it’s fully installed. I say, with no exaggeration, that having one tool of this type running successfully seems to be one the most critical differences between people who are thriving and on top of their lives — and those who aren’t.

A last Paul Graham quote –

““ … unless the rate at which social antibodies evolve can increase to match the accelerating rate at which technological progress throws off new addictions, we’ll be increasingly unable to rely on customs to protect us.”

Have the social antibodies evolved fast enough? No? Then you must protect yourself. Get on a keystone, any keystone, and — thrive.

We’ll continue with Background Ops next week. My best regards, always,

Sebastian Marshall


This is the second issue of Background Ops, the first series of The Strategic Review on Medium; if you like it, please hit the ‘Clap’ button or comment to let us know — and do you have any friends that would benefit from this concept? By all means, share this article with them.

Want to try out a Lights Spreadsheet? A template-generator and best practices guide is here:


Image credit: Dave Thomas