Roguelike - by Sebastian Marshall

In my opinion, this single shift -- towards "Hardcore Mode" where everything counts, no re-do's, death is permanent -- is what took my video-game playing habit from a mostly useless entertainment indulgence into something that actually starts to produce useful life lessons. Life, after all, life itself is run in "Hardcore Mode" -- there's no reload button if you screw up a job interview, or get mugged in a dangerous foreign country, or whatever other thing might happen in your adventures. By playing in Hardcore Mode, games became about thinking, strategy, preparation, balancing the tradeoffs between safety and resource usage (should I use the potion now to guarantee I win this one? will I need it later?); it requires creativity and patience. An additional underrated bonus is you'll usually do something stupid and get yourself killed when you're tired, so for savvy players, it de facto sets a "it's better to turn the game off now..." time.

This Isn't "Quake" -- On Keeping One's Composure

You get no points for playing fast. Actually, you're likely to die if you play fast. Playing fast means making bad decisions. You've maybe invested hours getting where you're at. You might even "like" your character or feel excited about the prospect of winning with them. And then, all hell breaks loose. Your natural inclination, if you're like most people, is to speed up, play faster, start making a compounding series of mistakes and errors, and wind up with your guy dead. Over many repetitions of this fundamental error, you learn to stop doing that. You learn to force yourself to slow down, breathe, think when things are tough.

No Heroism

Due to human nature, we tend to spend more time on the wars and conflicts that are epic in scope and disastrous for one side. We spend much less time focusing on where ugly things could have happened, but were prevented. Sun Tzu can wrap this up: "What the ancients called a clever fighter is one who not only wins, but excels in winning with ease."

The Mechanics Know No Morality

We're often more interested in editorializing or providing commentary than we are in engaging with reality well. Take the all-too-often-heard complaint that people who politick well tend to get more authority, promotions, and resources than people who just put their heads down and work. Here is my contention: you would do better by yourself if you looked to understand the mechanics, rather than editorializing or providing moral commentary.

Deserve's Got Nothin' To Do With It

In almost all media, protagonists win by virtue of being protagonists. It doesn't matter how stupidly they act. In fact, if they act stupidly out of a sincere genuine goodness, they become more likely to win. Protagonists win by virtue of being good people; not by virtue of preparation, training, planning, careful thinking, and excellent execution. This, I contend, is one of the most valuable things you can beat out of yourself. Mark this down: Deserve's got nothing to do with it. Being a good person isn't enough. The mechanics determine the outcome. Han shot first.

Paying the Inexperience Toll

As the old expression goes, "The worst thing that can happen when you go to Vegas is that you win." It's natural to overrate oneself for long stretches of time; most people do this, not just smart and analytical people. It's too easy to assume that having generally good intelligence, learning, and mental models will transfer rapidly even though you don't have knowledge of the specific domain you're going into. On the one hand, it's true: mathematics applies everywhere. Humans are human everywhere, with all the good and bad that entails. There's broad commonalities between all sorts of unrelated disciplines. What that means is, as you get smarter and wiser, you become able to pick up new fields faster. But I think part of that wisdom has to include that you're going to be dumb and inexperienced when you first enter a new foray -- call it "paying the inexperience toll." In any complex multi-variable domain, especially one with heavy variance or randomness, inexperience gets in the way of doing well.

In real life, if you're getting into a new domain, it's highly recommended you do "Key Decision Analysis" -- meaning, you write down your reasoning and predictions for what you're doing. It forces you to clarify your thoughts.

Unacceptability of Blunders; Excellence Not Required

Roguelikes are hard. One bad blunder can negate hours of perfect play. Bam, you're dead, there's the Grim Reaper; do you want to play again? The challenge to winning a roguelike isn't the challenge of being great; it's the challenge of being fundamentally sound, and then not making any fatal mistakes. Life often works in the same ways. There are plenty of areas of life where the best possible performance does not excel very much over merely solid performance, but where bad performance is disastrous.

Greater heights of excellence won't save you if you make a fatal blunder. Thus, we need to remove the chances of such a blunder.

Setting policies during peacetime if how you keep your head during wartime. In the heat of battle, you can get tied up and forget to keep a margin of safety. You can get obsessed on beating a particular enemy, instead of staying alive and avoiding fatal blunders. If you "leave it to judging in the moment," it's very easy to overreach.

Defensive Policies

When things are going poorly or going excellently, one's judgment tends to get compromised and it becomes harder to think clearly. You need to have already thought. Your basic policies should emphasize whatever is most important to success: -- For the writer: write every day. -- For the salesperson: generate new referrals/prospects each day. -- For the PhD candidate: work on the thesis every day. -- For the bodybuilder: follow the fitness plan every day. Etc.

A defensive policy to keep one sane during a bad time, and with explicit caveats for how exceptions are made -- these can be very valuable. These policies are set by looking at common failure cases, and putting down rules for how to stabilize or remedy those situations.

Example Writing Policy

  1. At the end of each day, when I plan the day ahead, my planning will include pre-scoping a piece of writing to do.

  2. When the time comes, I don't have to do that piece of writing if I'm highly inspired about something else that's worth exploring.

  3. If not heavily inspired, I will attempt to do "writing-related" stuff which means usually clarifying the outline of the piece I want to write. If it's called for, re-reading recent writing or doing some editing might be appropriate in this time. (Usually not, but sometimes is okay.)

  4. If none of the above is clicking, I will sit there and just suffer for at least an hour, doing nothing else. Suffering and doing nothing else is fine. Procrastinating or doing something that's not writing-related, under normal circumstances, is not fine. But sitting there just suffering is perfectly fine.

  5. I will schedule this writing to be the first full thing I do of the day. I will put it on the calendar and hold it as sacred as any appointment with a client, advisor, or very important contact.

  6. I will add a line to my Daily Tracking Template to tick off at the end of the day.

  7. I will add a "Writing Policy Adhered" line to my Lights Spreadsheet.

Specifying the intent (daily writing), the clear measurable duration (one hour), focusing on the process (time) instead of the result (word count, etc), tracking it (spreadsheet), planning each piece of writing the day before, doing it first thing in the day… these are all useful, but not as useful as what to do when things are going wrong. I have a very high adherence to this policy, and unsurprisingly, when you just sit and stare at a blank page without doing anything else for long enough, eventually something clicks. Policies that emphasize that mistakes will never happen are unrealistic. Policies that don't take into account unusual situations are ineffective.


Policies are designed to make your life easier. In the span and scope of infinite decisionmaking, narrowing it down to precisely what you're going to do before getting into the heat of battle is useful.

Here's a question -- when you're playing a game, would you rather have a range of a dozen different powerful abilities that are each nuanced effects and between all of them you've got every situation covered perfectly… or have one very powerful combo that's always correct to run, but never as strong as any of those dozen abilities? The answer is that, once you've gotten enough experience, you'd probably prefer to have the stronger overall character with a dozen different abilities. But when you're starting out, you're much better off with a clear way to play well. Unless you've established that you're always calm and level-headed in new endeavors across the board, you should be skeptical of your ability to be calm and cool under fire in something new. As such, life is a lot easier when there's a clear hierarchy of the best abilities to use and the order to use them in, with almost no exceptions to the best order of doing things. When you're new to something, you want less required skill and judgment.

When you're brand new, all else being equal, you want the simpler path of advancement, prioritization, and easier choices to make -- it's hard enough to pilot your character and navigate new ground when the choices are straightforward enough and you just need to execute… you don't need the added complexity. In real life, this translates to doing simpler, more straightforward, and less-prone-to-fail things rather than more complex, less straightforward, and riskier things.


Real life doesn't have specific points where you level up, with explicit points to be distributed between your stats and abilities. As such, it helps a lot to make some mental models of what you want to achieve in the world, to ensure you're progressing at a rate that's pleasing to you. The first and most obvious constraint is that there are exactly 168 hours every week. You can almost always do something worthwhile in a week. A week is a rather long time. If you got at least a minor gain each week, that's 52 gains each year. That's pretty good. But, in order to get gains, you might actually have to sit down with a piece of paper and figure out what's required to get the stat, trait, or skill boost that you want.

Buy What You're Missing

In the standard fantasy roguelike game, there's broadly two ways to get new abilities: 1. Train them as part of who your character is, permanently. 2. Buy them in the form of equipment. The following rule has some many small and medium-sized exceptions to it, but it stands as generally correct: If there's something you're terrible at, buy it temporarily; avoid training it permanently. You simply can't be good at everything -- we have limited resources. If your work is demanding and you don't love something that's "off-build" for you, you're far better off finding a way to avoid that entirely (get a condo that requires less maintenance than a house) or pay the money to get it taken care of, instead of putting in the time to develop skills that could instead lead to game-breaking life gains.

One Point Wonder Caveat

On the TOME discussion forums, players discuss strategy and builds. Sometimes an ability like Waters of Life is called "a one point wonder," meaning that a small investment in it permanently gets outsized large gains. Even if your build handles those threats other ways, it's really worth a single skill point in it, because it's like an instant "off switch" for two headaches. It's really good. In real life, a basic understanding of nutrition and of sleep hygiene are "one point wonders" -- a couple weeks of serious study can lead to permanent life enhancing benefits. Negotiation is a one-point wonder unless you're in a really rare role like a tenured research professor with no material needs who largely works solo. The very basics of negotiation -- knowing your BATNA (Best Alternative To Negotiated Agreement; your "next best option" if the negotiation doesn't go through), understanding the concept of a person's "negotiating range," knowing how to do basic research and get comps, and understanding the basic idea behind making offers and concessions and asking for offers and concessions graciously -- a single focused burst of training in this pays off incredibly well, even if your "life build" doesn't include much people/verbal skills. Basic awareness of your emotions and impulses is worth investing some training in -- mindfulness meditation is the most common way to train that awareness up.

Threshold Caveat

If you can cross a key threshold, even if it's off-build, it might be worth doing. For instance, high-income professions that require high hours generally don't combo well with learning advanced investing skills. Governance changes and the tax code changes, but putting a few points into commercial real estate investing and a few points into understanding taxes likely makes sense for a high-earning high-labor-hours professional.