The Myth of the 100-Hour Work Week

“Startup founders work 100-hour weeks.” I forget when I first heard this, but I believe it was around the same time I heard about technology startups.

At the time, I was very impressed with the tremendous passion and work ethic of these founders, who could spend 6+ days out of every week doing nothing but eating, sleeping, and working. And that really was exactly what I thought they were doing: getting 100 full hours, every week, of laser-focused productive work time, without taking breaks to chat about non-work things, or stare into space letting their minds drift, or take walks, or exercise, or anything.

Recently (for some complicated reasons I’ll post later), I’ve decided to impose on myself a work week containing as many productive hours as possible. In making my schedule, I took into account all the psychology of learning that I had researched over years of interest in such things: efficient thinking happens on 8 hours of sleep, taking frequent short breaks helps brains remember things by dint of primacy and recency effects, human circadian rhythms are diurnal and therefore napping in the “afternoon slump” is more effective than trying to work through that time, etc. When I was done filling up all my time with little blue boxes in Google Calendar, I tallied up all my productive working time and found that I had only 52 hours.

Now, to be clear, my schedule did not contain quite as much work as it theoretically could have. I had allotted myself an hour to make lunch, and two hours to exercise in the morning, and an hour and a half to socialize in the evenings. The purpose was to make the plan sustainable, so that executing against it wouldn’t burn me out.

But even if I didn’t care about that, I didn’t see how I could have gotten that productive-hours-per-week number up to 100. It just seemed inefficient, based on everything I had read about human brains, for someone to work nose-to-the-grindstone at a task for that many hours. Taking breaks to exercise and eat healthy food and sleep eight hours a night would make their thinking more efficient than just working longer hours.

I had a hypothesis, that people might say they worked for a hundred hours a week, but perhaps, they only spent 60-80 actually being productive. When I’ve worked full-time at an office, having to look productive regardless of whether I actually was, plus inefficient use of work-time doing stuff like chatting with coworkers, and the corporate busywork that comes with a salaried job like that, all took up significant time. This is a very common situation: statistically, the average number of productive hours an office worker has in an 8-hour day is 2 hours and 53 minutes.

But I wasn’t sure about this, and not having worked in a technology startup myself, I wanted to ask someone who had. So, I asked my mom. This was what she told me.

People who say they work 100-hour weeks may be at the office for a hundred hours, but they are actually productive for around 60. The remaining 40 hours is spent taking breaks of various sorts. But the reason they stay at the office for that time is so that they can take breaks in the same space as a bunch of other smart people working on the same set of projects they are. That way, discussions about not-work meld into discussions about work, and produce more productive time for the group in general over time.

This is the optimal workflow for any group of people working on a project for as much time as possible, as it turns out. And it’s used not only by technology startups but in every other area where such a thing may be needed. For example, before she got into tech, my mom worked as a researcher for NASA. They used the same system: people would work for several hours, then take a break and play foosball and talk about something unrelated, then get talking about their work at the foosball table, and then somebody would have an idea and run off to the office to go work on it.

Learning this, I was even more impressed than I had initially been. Apparently, every group of highly-productive people for a very long time had reinvented this same style of working. And now I get to use it, too.

Rationality is Generalizable

In order to make some extra money during this pandemic, I’ve been doing a bit of work fixing up one of my mom’s rental houses. All the work is within my preexisting skillset, and it’s pretty nice to have a physical job to give me a break from my mental work.

When fixing up a house between tenants, the first item on the to-do list is to create the to-do list, called a “punch list”. In order to create it, I walked through the house and noted down the problems: this railing is loose, this stair tread is broken, these tiles are cracked, etc. Once I was finished, I’d made a list that would probably take me about a week to complete.

And then I tripled that time, and sent it to my mom as my time estimate.

The reason I did this was in order to combat something known as the planning fallacy, one of many endemic flaws in the human brain.

When humans make plans, they envision a scenario where nothing goes unexpectedly. But reality doesn’t work the way human-brains-making-plans do. Fixing those cracked tiles ends up requiring ripping out eight layers of rotted wood underneath filling in the resulting two-inch-deep gap with concrete, then leveling it out with plywood before laying the new tiles. Repairing the crack in the living room wall ends up requiring replacing the whole gutter system, which was causing water to run through the bricks on the outside and into the drywall. When we just see some cracked tiles or some chipping paint, we don’t imagine the root problem that might need to be fixed: we just consider replacing a few tiles or repairing a bit of cracked wall.

This generalizes far beyond fixing houses. When a group of students were asked for estimates for when they thought they would complete their personal academic projects,

  • 13% of subjects finished their project by the time they had assigned a 50% probability level;
  • 19% finished by the time assigned a 75% probability level;
  • and only 45% finished by the time of their 99% probability level.

As Buehler et al. wrote, “The results for the 99% probability level are especially striking: Even when asked to make a highly conservative forecast, a prediction that they felt virtually certain that they would fulfill, students’ confidence in their time estimates far exceeded their accomplishments.”

Humans planning things envision everything going according to their plan, with no unforeseen delays: exactly the same as if you ask them for a best-case estimate, in fact. In real life, what happens is somewhat worse than the worst-case estimate.

There are some useful debiasing techniques for combating the planning fallacy. The most useful of these is to utilize the outside view instead of the inside view: to consider how similar projects have gone in the past, instead of considering all the specific details of this particular project. (Considering specific details drives up inaccuracy.)

I’ve used this technique often, but in this particular circumstance, I couldn’t. While I’d done every individual thing that would need to be done to finish this house before, I had never done all of them in sequence.

Considering this problem, you might advise me to ask someone who had done whole houses before. I have easy access to such a person, in fact. The issue with this solution is that this person always makes overly optimistic estimates for how long it’s going to take to complete projects.

You would think her experience would make it easier for her to take the outside view, to consider this house in the context of all the other houses she had fixed. This doesn’t happen, so what gives?

Roy et al. propose a reason: “People base predictions of future duration on their memories of how long past events have taken, but these memories are systematic underestimates of past duration. People appear to underestimate future event duration because they underestimate past event duration.”

In light of all this, my best course of action, whenever I cannot take an outside view myself, is to take my normal (= optimistic) estimate and triple it.

I made that three-week time estimate around the first of June. Today is the 16th, and I’m finishing the last of the work today.

This whole situation, like the planning fallacy in particular, is generalizable. Learning about cognitive psychology, and the persistent flaws in all human brains, is oftentimes more useful for coming up with correct answers than experience.

You might not think that the tactics for “how to not be stupid” would be as generalizable to every field as they are. Each field has its own tips and tricks, its own separate toolbox, carpentry is not like neurosurgery is not like musical composition… But we are all human brains, us carpenters and neurosurgeons and composers, and we are all using the same flawed circuitry generated by the same optimization process. Here, as in planning, the special reasons why each field is different detract from an accurate conclusion.

Knowing about one cognitive bias produced a better time estimate than thirty years of experience in the field. Rationality does not always produce such a large improvement, but it does prevent humans from making the types of stupid mistakes we are prone to. In my personal opinion, if a decision is worth making, it is worth making rationally.

What Is the “Wage Gap”, Anyway?

“For every dollar a man makes, a woman makes 77¢.” You’ve probably heard this statistic thrown around before. But what, really, does it mean? For a statistic we use to benchmark the “wage gap”, it’s a shockingly broad statement. Well, as it turns out, this statistic is legitimate, and it does demonstrate a significant problem with sexism in the modern world – but it doesn’t mean what you think it does.

Growing up, I always knew I wanted to do something big with my life. From fairly early, I was clear on what, though I wasn’t always clear on how (my idea of how to accomplish my goal at age 6 was to take over the country of Australia – how I thought this would help, I no longer remember). Over time, as I grew up, my ideas crystallized into an actual goal: I would become a successful technology startup founder.

Even so, there was always this discontent looming in my head. Being assigned female at birth, I had heard all the horror stories about the ways the patriarchy made womens’ lives hell, in and out of the workplace. And as a person who wanted in particular to make a ton of money, that “77¢ on the dollar” statistic haunted me. If only I’d been born male, I thought, I would be able to make almost 30% more money! For several months in my teens, I seriously considered making a medical transition in order to up my earning potential.

Except, no. Because that isn’t actually how it works.

According to my previous model of the world, the 77¢ thing applied across the board: a woman working any job would make 23% less than a man working the same job, always, in every industry. So a female teacher would make less than a male one, and a female software engineer would also make less than a male one.

But in actuality, the reason that women make on average 23% less than men is that women take jobs that pay on average 23% less. A female software engineer doesn’t get paid less than a male one – in fact, although women do make up a statistical minority of the programming/technology world, those who are a part of that space tend to make more than men, since women tend toward leadership roles. However, most women are not software engineers; most women are teachers, nurses, secretaries, cashiers, and retail workers. And these jobs pay much less than male-dominated jobs.

So, the source of the gender wage gap is not endemic sexism? Well, not quite. There is a reason that women on average choose jobs that pay less.

When my grandmother was young, there was a common saying in her college, that the women were only there to get their “Mrs. degree”. After she graduated, employers refused to take her on because she “was just going to get married and leave the workforce”.

When my mother was young, many of the other girls in her Catholic school made excuses for their lack of willingness to attempt difficult intellectual pursuits because they were “just girls”. (Her father never let her make these excuses, which is a decent part of what made my mother how she is.)

When I was young, I attended a series of all-girls STEM bootcamps that were designed to encourage girls to go into technical fields. I never much understood the point, because it had never occurred to me that gender had any relation at all to career choices.

Historically, women have been told that their being female limited their career options, or that certain careers were “less feminine”. Women who were told this type of thing comprise a significant portion of the women alive today. And hence, the 27% wage gap.

If you account for differences in college majors, occupations, working hours, and parental leave, the difference between women and men across the board is more like 3-6%.

But hang on, 3-6% is still significant. Where does that come from?

That small (but present) difference likely arises from a large variety of factors, including some amount of (real!) sex discrimination in the workplace. Still, my best guess on the biggest reason for the remaining gap is this:

Women are not systematically taught career skills.

I know a lot of men who were taught how to do business by their fathers, who own businesses. I can attest to the usefulness of learning business at a young age: I worked in my mom’s businesses most of my youth. It is possible to learn how to negotiate a salary, or interview effectively, or manage a team, without the ready-made mentor of a business-savvy parent, but it’s much more difficult. Most of the women in the workforce today don’t have that advantage.

Just working for a while doesn’t magically bestow upon you the skills you need to get paid what you’re worth. You aren’t going to learn how to interview well just by doing it a whole bunch – at a minimum, to understand the whole process you’ll need to come at it from both ends. And you aren’t going to learn how to be an effective manager without getting advice from someone who is.

The easiest way to learn these things is, obviously, to have a parent who will teach it to you. In absence of such, many women are left without critical career skills, and make less money as a result.

This means a number of things. First, we as a society need to stop gendering careers. That girls-only STEM program I went to should be abolished, because it should not be a novel concept to anyone that girls can be technicians (though the general concept of allowing young people to shadow technical professionals was a great thing to have; my brother should just have been allowed to attend).

Second, any individual women who are busy making excuses for their poor work ethic and poor salaries, blaming their gender, should get ahold of their bootstraps and start pulling themselves up.

Third, if any parent cannot provide their children with a satisfactory training in business, that is a critical failure, and they should do their best to outsource that training which they cannot provide themselves (ie, they should send their children to a program which can provide such training).

And fourth, most obviously, sexism in general should be eradicated.

Lastly, we all need accurate information on what the wage gaps endemic to our workplaces are, and what causes them. If we have an inaccurate picture of the reason for such statistics as “for every dollar a man makes, a woman makes 77¢”, we are doomed to waste our efforts on ineffective solutions. And given how bloody slowly change happens in modern politics, inefficiency is not an available option.

Things I Would Do With Immortality

I’ve previously discussed that I didn’t like reading fiction growing up, because I knew that if I thought about it too hard, it would break down. In real life, you can do experiments to answer your questions, instead of needing to rely on authority or source material, but in a story, this isn’t true. The real universe is modeled by quarks; stories are modeled by plots.

The fact that real life is based on universally consistent laws is a nearly endless source of intrigue, entertainment, and general fun, at least for me. Whenever I ask a question about reality, I know that it has an answer, somewhere. If I don’t know it, I can learn about it from someone who does, and if nobody knows it, I can find the answer myself. The existence of a consistent reality that I can do experiments on means that I am not limited in my ability to learn stuff by anything besides my willingness to do so.

The primary reason that I haven’t gone on a quest to rediscover every single insight ever made by the human race – which seems to approximate the Maximum Fun Plan – is because doing so would take orders of magnitude more years than I am presently expected to live, barring major advances in medical science. So, I’ve got to solve the pesky mortality problem first. But once I do… I certainly plan to spend a lot of time rediscovering things.

It might seem a bit odd, that I would want to spend decades and centuries rediscovering things that other people already know. A waste of effort, isn’t it? It would be more efficient to ask somebody who knows about the thing already.

More efficient it may be, indeed – which is why I don’t do it right now – but more fun it is not. I’m certain that Isaac Newton had way more fun inventing calculus than I had learning about it in school, and that isn’t just because our modern school system is a train-wreck. The joy of discovering something for myself is substantially greater than that of hearing the solution from somewhere else before I’ve even tried my hand at the problem. (I do prefer that the solution be printed somewhere, especially if the experiments to confirm my solution are difficult to create. It would be nice to hear somebody else’s solution to the AI-box problem, for example.)

Not only is the joy of the knowledge-acquisition inherently less, but the quality of the knowledge itself is also lower. When you discover something for yourself, you don’t have the problem of storing as “knowledge” what is actually just a referentless pointer (ie. a physicist tells you that “light is waves”, and you store the phrase “light is waves”, but you don’t have the background knowledge to really know what it means, and you couldn’t regenerate the “knowledge” if it were deleted from your brain). You also won’t have the potential pitfall of taking the solution for granted. People often don’t properly contextualize beliefs that they themselves didn’t generate: it feels to them like things which are now understood by Science, like rocks and stars and brains, have always been that way, instead of having been a mystery to the human species for the many millennia until they suddenly weren’t anymore.

There is a more abstract objection to the idea of reinventing old discoveries, coming from a less efficiency-focused mental place. The idea seems to be that, if somebody already knows, the problem is for some reason no longer interesting. It’s the position taken by everyone who is enraptured by the breaking new scientific controversies, but is not the slightest bit interested in the proved-correct equations of General Relativity.

But in my book, it doesn’t much matter what somebody knows, if I don’t. When I was young, I wanted to know how my body worked. Why did my hands move when I willed them to, but a glass of water wouldn’t slide across the table to me with a similar mental effort? Why did eating a whole bunch of candy make me feel ill, but eating a whole bunch of salad didn’t? I didn’t know, and I wanted to know; if you had told young-me that somebody knew, I would have replied “okay, can they tell me, please?”.

So far as I was, and am, concerned, if somebody else happens to know the answer to a question, that doesn’t cheapen the discovery for me. In fact, it wouldn’t make any sense for me to have a term in my utility function for being the first person in the universe to make a discovery, because for all I know, super-advanced aliens on the other side of the galaxy have already discovered everything I could possibly want to learn. If my choices are between never taking joy in a discovery, because somewhere else, someone else might already know the answer, and having fun, I’ll pick the fun.

It might be impossible for me to do anything about this until I (or somebody else) create a feasible solution to the imminent mortality problem, but once it happens, you can bet you’ll find me in a remote field, trying to find the optimal way to rub two sticks together.

Thoughts from the Pandemic

I’m not benefiting anyone – especially myself – by pretending I’m okay. The truth is, I’m not.

It isn’t for the reasons you might think. By prudent accident, I left San Francisco just before the pandemic began, and I was able to fly back to Pittsburgh with no trouble. I’m able to socially isolate, I don’t need to pay rent, I don’t need to work, and neither does my partner. We’re staying with my family, none of who are front-line workers. They are also in no financial trouble, because my mom is still employed and getting plenty of work.

None of us are at high risk of complications from the virus, either, if we did manage to get it. Nobody in my house is outside the age range of least risk, nobody is immunocompromised or has any history of lung problems. The likelihood of anyone in my family, including me, dying if they got this virus is around one percent: around the same as any of us dying in a car crash. Definitely within the realm of acceptable risks that we take every day.

So I don’t have to worry about my health or safety, and neither does anyone I know very well, for the foreseeable future. Then what’s wrong with me? Why can’t I be productive? It’s not as though I was planning to do anything with the next year besides sit at home and work on accomplishing my personal goals. Being forced to stay home shouldn’t be a hindrance. Why can’t I focus?

I’ve asked myself that question a hundred times, and come up with a hundred answers. Without a professor or boss or client to force me to do it, I’m having a trouble working on my own goals on my own time. I’m having trouble focusing on my work because I benefit from working in a different environment from the one I recreate in, and isolating at home makes it hard to separate the two. I’m used to having a schedule which is exactly the same every day, and now that nobody’s forcing me into doing that, I’m falling into a less healthy, less consistent rhythm.

But none of the solutions I tried, responding to those problems, worked. Because none of those were the real problem.

Oftentimes over the past few months, I’ve been watching a lecture in one of my online classes – that was why I came back here in the first place, so I wouldn’t have to pay SF rent while trying to learn a whole bunch of new skills – and it’s been genuinely interesting. But then, without being able to help it, I’ll think about the rest of the world. And I’ll imagine, because I know they exist – though I’ve listened to as little of the news as possible – the patients who need eight transfusions in a day, not because of any internal or external bleeding, but because the coronavirus is eating their blood faster than their bone marrow can produce it. And I’ll imagine the patients who are breathing their last labored breaths, alone, in tremendous pain, with no friends or family around, no one to hold their hand, because the nurses and doctors must enforce social distancing procedures. And I won’t be able to force myself to focus on my lecture, because how the hell could I, when that’s happening to millions of people around the world?

It doesn’t matter that I don’t know anyone in this situation. Somebody does. Somebody’s loved ones are living like this, dying like this, and there is nothing I can do about it. If I were in a position of power right now, of the sort I hope to attain at some point in the future, I would be providing masks for doctors, buying ventilators for hospitals, paying peoples’ medical bills… or at the very least, not making the horrible decisions that so many people in state and federal offices, and at the heads of major corporations, are making right now.

But I can’t do any of that. And so I sit with my head in my hands, and I sob.

Obviously, that isn’t useful. I can’t get any work done that way. And so, instead, for the past two months, I’ve been shutting down my empathy as hard as I possibly can. But there’s a problem with doing that too. I decided a long time ago I was going to do a very hard thing with my life, and I decided to do it because I care about people. But caring requires empathy, and in absence of that… there’s no longer any reason to do the hard thing. In fact, there’s no reason to do anything; it’s not like I have anything else worthwhile to do with my time. I might as well just not get out of bed.

I’ve been accustomed to having an endless well of motivation, somewhere in me, that I could call upon. If I had trouble forcing myself to do something difficult, I would simply think about how I wanted to stop people from dying, and that would fix it. That’s gone now, and I don’t know how to get it back.

It’s gone because I can’t think about death at all right now without thinking about how it’s happening. That train of thought used to be a motivator, not a paralytic, because my mental image of “death” in general, while bad, was not so horrible as to cause fits of grief-stricken sobbing. But the majority of people who die, don’t die the way people are right now.

It’s not even mostly about the way the coronavirus itself destroys people from the inside out. It’s the fact that everyone who is dying right now, regardless of how, is dying alone. My grandmother died a month ago, of Alzheimer’s, and my grandfather (who had been visiting her every single day for the years she’d been hospitalized) wasn’t even able to be there, on his wife’s final day, to say goodbye. We still haven’t had the funeral. It would be a social gathering.

I can’t think about any of this, but I can’t not think about it. It’s a catch-22, a self-perpetuating system that I haven’t found any way to get out of.

I’ve tried a lot of things, attempting to motivate myself to keep working on my goals without opening the floodgates of my empathy too wide and drowning. I’ve been re-watching the shows that inspired me, re-reading the books that crystallized my heretofore-unwavering faith in humanity, re-listening to the songs that have always brought happy tears to my eyes. But it doesn’t work. Because what I’m feeling can’t be fixed by avoiding it.

People, in general, grieve a lot of different things. Ordinarily we think of grief as coming from losing someone you love; but people can also grieve relationships, connections, places, theoretical futures, ideas. Perhaps it should have been obvioius, the patterns of thought, but I didn’t realize until yesterday that I was grieving. Probably because most people don’t grieve on behalf of the entire human race.

Still, it shouldn’t have surprised me that I would. My circle of concern has always contained every sentient being in the universe. And of course I understand, as everyone in every society does, that when a member of a person’s circle of concern dies, that person will grieve, somehow. It’s just unusual, I suppose, for a person to really be so invested in the entire world to grieve over a global pandemic that none of their loved ones have been personally affected by.

As a result, I’m working on letting myself feel whatever I feel, and not bottling it up trying to be productive at the expense of my own mental health. The advice I’ve heard on how to deal with grief in general is helpful, even in a situation it’s not ordinarily applied to. I’m hoping that with the knowledge of what’s actually going on in my skull, I can gradually return to my normal life.

I’ve stopped pretending, to myself and everyone else, that I’m okay. I hope that by telling the truth, I can move past it.

The Problem With Statements of the Form “X is Y”

Cats are mammals.

Gravity is the curvature of spacetime.

Both of these sentences are true. And they both use conjugations of the verb “to be”. But the usage of that verb is very different.

The first sentence is true in the sense that we as humans have defined a category called “mammals”, members of which have certain characteristics, and cats have the required characteristics to put them into that category.

The second sentence is true in the sense that “the curvature of spacetime” describes a thing that exists in the universe, to which we have given the name “gravity”. It’s a literal definition, not a taxonomical categorization.

The problem with these two different uses of “to be” is that people mistake the one for the other. They think that when scientists reclassified Pluto as a dwarf planet, it was because they’d learned something new about Pluto, as opposed to having simply revised the definition of a “planet”. But this is incorrect. A planet is whatever humans say a planet is, because the entire purpose of the category is to allow us to talk about “planets” without having to say “celestial bodies that have assumed a roughly spherical shape, orbit a star, and have cleared the space around their orbits” every time.

This isn’t to say that categories are meaningless, or can be defined in any way we please. Because a category is a convenient way of referring to a set of traits, those traits have to be common enough as a complete set to be worth referring to. We shouldn’t define a category to mean “a person with black hair and green eyes”, because those two traits aren’t any more likely to occur together than any other hair/eye color combination, and that set of traits doesn’t imply anything else useful about the person.

It is to say, however, that a category is not a fact about the universe, and that a category can and should be changed to better suit our purposes. Take, for example, the categories “male” and “female”. Most of us are accustomed to using these categories to imply a common combination of gender presentation, chromosomes, and sex characteristics. However, a lot of people have recently been changing these categories. In doing so, they aren’t violating any universal law that says “all masculine-presenting humans must have XY chromosomes”, because there is no such universal law. They are redefining a category that was defined in the first place by English-speaking humans and can be redefined by those same humans.

(Another recent change to categories: birds are reptiles.)

This same problem occurs the other way around: people mistake observations about the universe for human-made categories. I learned to say the phrase “gravity is the curvature of spacetime” when I was 9. It successfully impressed a lot of grownups, but the image in my head was a stretched-out tarp with a ball in the middle. It took nearly a decade for me to actually understand enough physics and math to grasp its real meaning. And when I did, my thought was basically “oh shit, gravity literally is the curvature of spacetime”.

When we talk about facts we understand, we’re not saying riddles or passwords. If somebody who doesn’t have the relevant background knowledge to understand us overhears, they might not realize that what we say is a literal observable fact, which they too can observe if they know where to look, but that doesn’t change it. The unfortunate reality is simply that the conversion from thought to language is not lossless. And until we invent telepathy, it probably never will be. Still, simply knowing the distinction between these two definitions of “X is Y” type sentences was helpful to me, and so I’m passing it on.

My Advice for My Younger Self

…or for other people sufficiently like me and in a life phase before mine such that it might be applicable.


I want to start off by saying that I myself am still, by many peoples’ definitions, a young person. I don’t think this should inhibit my ability to give advice, either to my hypothetical younger self or to others. Chronological age is a mediocre indicator of life phase, anyway.

My current life phase is that of someone who has completed a college degree, taken an internship that became a well-paid (above the median income of adults in America, where I live) full-time job, and subsequently decided to move back to my hometown in order to complete additional schooling and certifications. My goal in life is to cure mortality; as an intermediary step I intend to become extremely wealthy, and for that I have a plan to make a six-figure salary within the next five years.

A younger me, or a young person similar to me, has ambitions to fix at least one of the world’s problems, but perhaps doesn’t know of the best way to go about doing so. That’s the type of person that I’d like to provide advice to, because that’s the type of advice I wish I could have gotten from someone just a little further along the path than I was, back then.

Advice #1: Find your purpose. Right now.

By really no virtue of my own, I found my purpose very early on. (I didn’t know how to achieve it, but that’s a different post.) If you don’t know what yours is yet, I recommend finding it as soon as possible.

Not having an end-goal makes it extremely difficult to make decisions – especially the big ones, but since those propagate downward, the small ones too. It doesn’t matter if your end-goal changes over time, just make sure that you have something you’re moving towards.

Think about it as a physical destination. You pick a place to go, and based on that you choose a route, and based on that you choose how to prepare for your trip. If your destination changes partway through your journey, you probably figured out a better place you’d prefer to be than where you were initially headed. That might come with a little bit of regret (at having not chosen the better path first), but it doesn’t feel hopeless or aimless. By contrast, just walking out your front door with no preparation and no plan is liable to end you up stranded fifty miles from your house with no idea where you are or how to get somewhere better.

When choosing a goal, make sure it is specific, but it doesn’t have to be easy, simple, or even possible. That being said, choose something that would genuinely make you very, very happy to actually achieve. The harder the goal, the more critical it is that it would actually make you happy. You, not your parents or your friends or society. If you don’t know what would make you happy, consider what state of the world would make you content with your life and then think about the first, clearest, or most time-sensitive step that you could take in the direction of creating that ideal world. Further, if the goal might be impossible, make sure that an approximation of it, or significant movement in the correct direction, or a discovery of why it’s impossible, would also make you happy.

Advice #2: Use your advantages.

All other things being equal, the younger you are, the easier it is to change direction, and the more time you’ll have to pursue that new direction once you choose it. Both of these things are the reasons I was urgent with my first piece of advice; your life goal determines your path, which determines how you use what advantages you have.

You have several specific advantages by virtue of being younger. Besides the obvious, here are a few advantages you have as a young person trying to make a change to the world.

If you’ve not yet graduated from high school, you have:

  • AP tests. If your path requires a college degree (ie, involves becoming a doctor, lawyer, financier, accountant, technology consultant, or something else where not having a degree would severely hinder you), AP tests are an extremely cheap way to get college credits. They cost $25, compared with CLEP tests that cost $85 and college courses that cost thousands.
  • Free education. This is, admittedly, a bit of a double-edged sword, because it’s also mandatory and frequently pointless, but the fact remains that you don’t have to pay for your education now. If you spend some time poking around, you’ll likely find that the school system is remarkably malleable if you know how to mold it. So, if you do your research and know your life goal you can make the most of this, the last time in your life when your only job is learning. Having a trustworthy non-minor can help you out here, so it’s worth trying to persuade your parents or school advisors to help, but they aren’t necessary. As a starting point, I recommend looking into some combination of dual enrollment (if your path involves college) and internships (regardless).

And if you’re currently in college, you have:

  • The ability to choose your major. If you’ve decided a college degree is indeed critical, what you major in has a significant impact on your career going forward. It determines what projects and certifications you get while in school as well as employers’ impressions of you immediately after you graduate. Because the decision of a major is so critical to your path, however, make sure not to listen to people who tell you to major in whatever you like. Your major should be determined exclusively by your choice of future career.
  • Projects and internships. You will need to actively pursue these – they won’t likely be thrown into your lap – but most colleges have some way to support students working on personal projects or looking for internships. Plus, if you have a full-ride scholarship, you don’t need to worry about whether the internships are paid, only that they give you relevant experience in the field you’d like to begin your career in.

And if you’re a recent graduate, or otherwise early in your career:

  • Employers will expect you not to know what you want to do yet. If you take a job in sales, and then one in marketing, and then look for one in accounting, that won’t seem strange to employers. By contrast, it can be more difficult to change careers if you’ve been doing something for a while: if you’re a senior marketing manager, employers will wonder why you waited so long to make the switch over to accounting. Further, you may have a tough time taking the inevitable pay cut to move to a more junior role. Therefore, doing some experimentation to figure out what you want to build your career in early on is not only easier, but expected.

All of that being said, if you feel like you’ve messed something up, it’s not the end of the world. If you didn’t take any APs in high school, or you have debt from an unnecessary (or unnecessarily expensive) college degree, that doesn’t prevent you from being able to achieve your goals. Fix these problems however you can (drop out of college immediately if you decide you don’t need a degree, get out of debt as quickly as you can, etc), but don’t get upset with yourself for making mistakes or doing things that were suboptimal. Apply whatever lessons you can to your actions going forward, then stop thinking about it.

Advice #3: Soft skills matter. Build them on purpose.

When considering your career path, it can be easy to focus disproportionately on the hard skills. “I need to learn financial accounting, business law, and economics,” you might think, if you want to become an accountant. And that might be true. But you also need a strong work ethic, good social skills, and self-management. The latter three are equally, if not more, important than the former.

Building soft skills is a three-step process:

  1. Figure out what skill you need. Don’t just give a name to the skill, but define specifically what being good at that skill looks like, and decide how good you need to be at it.
  2. Figure out what you need to do to get better at the skill, and start doing that. For most soft skills, it’s a mindset shift combined with an action shift.
  3. Continue doing what you decided to do in step 2 for at least 30 days or until it becomes a habit. Iterate until you’ve fulfilled the requirements from step 1.

As you meet new people and move further down your career path, you’ll find out that you need soft skills you didn’t previously know about. Continuously moving through the above process for every new skill you decide you need is going to be a major part of your early career, and likely also your entire life.

In order to help you find soft skills you might need, make a regular habit of looking at advice given by people further along your chosen path than you are. They don’t need to be on precisely the same path: for example, if your goal is to start a successful technology startup, look at advice given by senior developers, project managers, CEOs, CTOs, CIOs, and COOs, as well as startup founders. There’s a lot of soft skill overlap between these, and erring on the side of gaining too many skills is always better than not having enough.

Advice #4: Fail faster.

There’s a software testing process called “shift-right testing”. The mentality is that, since it’s impossible to have zero bugs, your software should fail as fast as possible, with as little user impact as possible. This will make it possible to find and fix errors quickly.

If you tend to be a stubborn person (as I am), applying this mentality to your life will prevent you from beating your head against too many walls. Essentially, if a step on your path is very difficult, check if it’s a difficulty that you should try to overcome or a difficulty indicative of a flaw in your plan. If it’s a flaw in the plan, fail fast, and stop working on the thing.

It may enrage you to hear me say, essentially, “give up.” But giving up because you decided it’s a suboptimal path is not the same thing as giving up because you can’t handle the work required for the optimal path.

Here’s an example. Prior to my current role, I worked a sales job for around a year. I took that job in the first place to improve my social skills, which is an area I’m naturally poor at. After a year there, I had learned a lot, but I felt I could still learn more. Unfortunately, the person who had mentored me for that time quit, and no one else was as good. Further, because I had at that point been commuting to a job over an hour’s drive away, working 10-12 hour days, and being in college full-time, on top of being naturally poor at the central skillset required for the job, I was feeling very burnt-out.

Even despite this, I didn’t want to quit. I wasn’t nearly as good at sales as I wanted to be yet. I still got nervous doing cold calls. I still had a hard time matching the energy levels of my prospects. But after a long and tear-filled conversation with my mom, I realized it was silly to keep beating my head against this: I’d learned plenty already, if I needed to know more I’d have plenty of opportunities to learn, and I was at the end of my mental rope. It made more sense to take some time away from working to finish my degree, then look for a better job. So I resigned.

If you can remember to fail fast, it will also help you to avoid sunk-cost fallacy. Deciding you have to continue doing something, purely because you’ve already spent a lot of time or energy on it, just means you’ll waste even more of your time. But if you can fail fast, and let it go, you’ll be able to spend your future doing something more effective than what consumed your past.

You Are an Incomplete Story

Growing up, I never much liked fiction. It was probably because I knew on some level that, if I thought about it a little too hard, it would break down.

In the real universe, you can ask a question like “why is the sky blue?” and find out the answer yourself. You can speculate from the existence of sunsets and rainbows and prisms the concept of white light refracting when it bounces off of things, and do experiments to confirm your hypotheses. If you keep on asking questions, you’ll find out about the – consistent and universal – laws of reality. And if you ask a question that no human knows the answer to, that doesn’t mean you can’t find out the truth.

In a story, this isn’t true, because at a fundamental level, stories are created by taking human-level understandings of reality and modifying them in a way that makes no sense when considering the underlying universal laws. The real universe is modeled by quarks. Stories are modeled by plots.

I’ve grown to appreciate stories more over time. Although they cannot produce the sense of wonder that I get from reality, they still have valuable training data. The best, most helpful advice I’ve ever had the privilege to give comes dually from two sources: my study of rationality, and my reading of good stories.

But stories still have a major pitfall that’s applicable even to those who don’t derive your sense of wonder from the perfectly unified laws of physics.

A story, by its nature, has to be completed at a satisfying end-point. Once its plot has been resolved and its tension released, the book comes to a close. Sometimes this comes at the end of the main character’s life – and so maps conveniently to a human life’s natural close – but this is almost always not the case. The main character, and the other characters as well, typically have futures that are assumed to continue after the last page. We just don’t read about them.

And we wouldn’t want to. As much as we love to see happily-ever-afters, reading chapter after chapter of our main character’s boring daily life after all the plot has been resolved would be dull. Even fluffy fan-fictions have an end. They don’t depict the complete, uninterrupted stream of a character’s life.

Let’s contrast this with real life. There is no-one chronicling every aspect of our existence, even for a short period when it’s most interesting. Six months of training can’t be skipped over with some motivational music and a montage: you have to literally get up and study or go to the gym every single bloody day for six actual months. And our stories don’t end, not unless we die.

If someone ever writes a book about us, they’re going to have to cut out some pieces and skip over others to fit it into a compelling narrative. And despite this, it’ll still be difficult, because real human lives are messy in a way that good story plots never are. Human lives are chock-full of Chekov’s guns that never fire, plot threads that are never resolved, and a constant stream of experiences that only properly ends at death.

It’s natural to think about your current self as at end of your story. After all, it’s the end of your experiences thus far, and if your life is a story, you are at the end of it, right now and always. But you have a future that you haven’t experienced yet, where events you haven’t predicted will happen and plot threads you haven’t imagined will start. Most of the things you’ve experienced so far will be completely irrelevant, maybe totally forgotten, in twenty years. That would make no sense in a story, but it happens all the time in real life.

So this is your reminder that you’re not defined by anything you’ve done so far, and that anything you don’t like about who you are right now can be changed. Your character has so much more room to develop.

This is also your reminder that your life is not comprised of the highlights that will be picked out in your possible future biography. It’s comprised of your day, whatever your day is – get up, go to work, come home, go to sleep – over and over forever. If you don’t like your day, that might sound terrible, but the only way to make it better is to improve the little things you do every day, and be a little happier in every moment, instead of waiting for some massive plot twist or new character introduction to fix everything.

I suppose I could say that your life is an incomplete story, and it always will be. You can think about it that way, if you like. It’s mostly correct if you think about a story that never ends. Still, it’s more accurate to say that your life is not a story at all. Comparing the two is, somewhat literally, comparing the output of a human brain to the contents of the universe. Your life is a life, which can be molded into a story only if you cut a lot of it out.

Ditch Pros and Cons: Use a Utility Function

If you’ve ever met me in person, you know I talk a lot about utility. My close friends are used to answering questions like “does this have net positive utility to you?” and “is that a strongly weighted component of your utility function?”. Every time I make a decision – what to do with my evening, or what to do with my life – I think about it in terms of utility.

I didn’t always do this, but I’ve adopted this way of thinking because it forces me to clarify everything that’s going on in my head and weight all my thoughts appropriately before making a decision. When I decide things this way, I genuinely feel like I’ve made the best possible choice I could, given everything I knew at the time.

What on earth is utility?

Utility is just a fancy word for “value”. If you enjoy chocolate ice cream, then eating chocolate ice cream has positive utility. If you don’t enjoy vanilla ice cream, then eating vanilla ice cream has negative utility.

One action can have multiple kinds of utility. You can add together all the utility types to get the action’s net utility. For example, if I assign positive utility to eating ice cream but a negative utility to gaining weight, there will be a certain optimal point where I eat as much ice cream as I can without gaining weight. Maybe, if I assign eating ice cream +5 utility, not gaining weight +5 utility, and exercising -5 utility, then it would make sense for me to hit the gym more often so that I can eat more ice cream without gaining weight.

Having numbers that are consistent is helpful sometimes, but isn’t strictly necessary. When I need to make quick, relatively straightforward decisions, I typically just make up some utility numbers. This is still useful, though, because utility calculations in a small isolated system are basically matters of ratios. It doesn’t matter exactly how much utility I assign to something, but if X has 5 more utility points than Y, X is preferable.

Forcing yourself to make up numbers and compare them to each other reveals what you care about. If you initially thought you didn’t care much about something, but then realize that if you calculated net utility with a low number assigned to that thing, you’d be unsatisfied with the result, then you care more than you thought you did.

It might be somewhat unclear, with my super-simple examples so far, what you can assign utility to. So, here are some examples of things that I assign positive utility to:

  • Reading good books
  • Doing new things
  • Increasing utility according to the utility functions of people I care about
  • Building neat software
  • Drawing with markers
  • Writing stories and blog posts
  • Improving/maintaining my mental and physical health
  • Having interesting conversations
  • Improving the quality of life of all sentient beings
  • Running
  • Riding my bike
  • Taking walks with my fiance
  • Figure skating
  • Eating ice cream

If you enjoy doing it, if you think you should do it, if it makes you happy, if it’s a goal you have for some reason, or anything else like that, you assign it some amount of positive utility. You can even assign positive utility to things you don’t end up doing. That’s because the net utility, after accounting for circumstances or mutually exclusive alternate actions. Knowing that you would do something, barring XYZ condition, is a useful thing to know in order to dissect your own thoughts, feelings, goals, and motivations. The converse is true, too: you can assign negative utility to things you end up doing anyway, because the net utility is (perhaps barely) positive.

So if that’s utility, what’s a utility function?

A utility function is a comprehensive set of everything that you assign any utility to – aka, that you care about in any way. The inputs are quantities of certain events, each of which are multiplied by their respectively-assigned utility value and then added together to get the total expected utility of a given course of action.

Say I’m with my sister and we’re going to get food. I personally assign a strong net positive to getting burgers and a weak net negative for anything else. I also assign a positive utility to making my sister happy, regardless of where we go for food. If she has a strong net negative for getting burgers, and a weak net positive for sushi, I can evaluate that situation in my utility function and decide that my desire to make her happy overpowers the weak negative I have for anything besides burgers, so we go get sushi.

When evaluating more complex situations (such as moving to a job across the country, where positives include career advancement and increased income, and negatives include having to leave your home and make new friends), modeling your own utility function is an excellent way to parse out all the feelings that come from a choice like that. It’s better than a simple list of pros and cons because you have (numeric, if you like) weights for all the relevant actions.

How to use your utility function

I don’t keep my entire utility function in my head at one time. I’ve never even written it down. But I make sure I understand large swaths of it, compartmentalized to situations I often find myself in. However, if you decide to actually write down your utility values, make them all consistent, and actually calculate utility when you make decisions, there’s nothing stopping you.

In terms of the optimal way to think about utility calculations, I have one piece of advice. If you come out of a utility calculation thinking “gotcha, I can do this”, “alright, this seems reasonable”, or even “ugh, okay, I don’t like it but this is the best option”, then that’s good. That’s the utility function doing its job. But, if you come out of one thinking “hmmm… I guess, but what about XYZ contingency? I really don’t want to do ABC…”, or otherwise lingering on the point of decision, then you’ve forgotten something.

Go back and ask “what’s wrong with the ‘optimal’ outcome?”. It might be something you don’t want to admit to yourself, but you don’t gain anything by having an inaccurate perception of your own utility function. Remember that “I don’t wanna” is a perfectly valid justification for assigning negative utility to an action. In order for this process to work, you need to parse out your desires/feelings/goals from your actions, without beating yourself up for it. Your utility function already is what it is, owning up to it doesn’t make it worse.

Once you have a pretty good handle on your own utility function, you can go ahead and mentally model other peoples’. Humans are calculating utility all the time in the form of preferences and vague intuitions, so even if other people don’t know their utility functions, you can learn them by a combination of watching their actions and listening to their words. (The discrepancy between those two, by the way, is indicative of the person choosing an action with suboptimal utility. You can point out this discrepancy politely, and perhaps help them to make a better decision.)
You might be surprised at how much easier it is to make group decisions once you know how everybody’s utility calculations will go.