Advice on Upskilling

– Working Draft –

Note: If you are reading this as a PDF,

consider switching to the Google Doc
which may contain new updates.

Authored by Justin Skycak

Updated 10 February 2025
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Authored by Justin Skycak

Copyright © 2025 Justin Skycak
First edition (working draft), updated 5 February 2025.

All rights reserved. No part of this publication may be

reproduced, distributed, or transmitted in any form or by any
means, including photocopying, recording, or other electronic
or mechanical methods, without the prior written permission
of the author, except in the case of brief quotations embodied
in critical reviews and certain other noncommercial uses
permitted by copyright law. For permission requests, contact
the author through the website below.

www.justinmath.com/contact
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Contents​

Preface................................................................................9
Chapter 1. Consistency................................................... 11
You’re Not Lazy, You Just Lack a Habit........................................... 11
Don’t Have a Passion? Go Create One..............................................12
Make the Habit Easily Repeatable.....................................................13
The Hardest Part is Just Getting Started..........................................14
Don’t Overreact to Bad Days..............................................................15
Aim for Virtuous Cycles..................................................................... 16

Chapter 2. Skills.............................................................. 17
The Importance of Hardcore Skills................................................... 17
The “Alien-Level Skills” Hack........................................................... 18
The Importance of Having Your Prerequisites In Place................ 20
Fortify Your F*cking Fundamentals..................................................21
Actively Doing is the Key to Alpha................................................... 22

Chapter 3. Discipline...................................................... 25
The Magic You’re Looking For is in the Full-Assed Effort You’re
Avoiding................................................................................................ 25
At Some Point Doing the Hard Thing Becomes Easier Than
Making the Hard Thing Easier.......................................................... 26
How to Cultivate Discipline...............................................................27
Keep Your Hands On The Boulder....................................................28
Just Do The F*cking Work..................................................................29

Chapter 4. The Grind...................................................... 31

The Most Superior Form of Training................................................31
Outsized Success Requires Outsized Work......................................33
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Transformation Is Discomforting..................................................... 34
Enjoyment is a Second-Order Optimization................................... 35
Ability is Built, Not Unlocked............................................................36
What Max-Efficiency Training Feels Like....................................... 37
The Necessity of Grinding Through Concrete Examples Before
Jumping Up a Level of Abstraction...................................................38
Be Willing to Do Tedious Work.........................................................39
Don’t Undervalue Turning Up the Dial on Your Grind, but Don’t
Overvalue the Last Turn..................................................................... 39
Failure Is NOT the Key to Success.................................................... 41
Focus Less on Feelings and More on Measurable Progress.......... 41
The Problem with Overly Difficult Problems..................................43

Chapter 5. The Journey...................................................45

The 3 Stages of Talent Development.................................................45
There Are No Shortcuts in Talent Development............................ 47
If You’re Making Silly Mistakes Then You Need More Practice.. 47
No Train, No Gain............................................................................... 48
You Are a Car....................................................................................... 49
What to Do When You Hit a Ceiling................................................ 49
Get Yourself In A Position Where You Can Eat Risk.....................51
How to Allocate Your Bandwidth While Searching for Your
Mission.................................................................................................. 51

Chapter 6. The Team...................................................... 53

If You’re Asking Someone to Be Your Mentor then You’re Doing
it Wrong.................................................................................................53
Put Pressure on Your Boss to Come Up with More Work For You..
54
Get On the Right Team....................................................................... 55
Competition as a Means of Collaboration....................................... 56
Your Goal is NOT to Prove You're Smart, it's to Make Problems
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Go Away................................................................................................ 57

Chapter 7. The Mission.................................................. 59

Selecting a Good Problem to Work On............................................ 59
The “Progress Equals Pressure” Formula........................................ 62
Love What You Do...............................................................................63
Be a Builder, Not Just a Fighter......................................................... 64

Chapter 8. Motivation.....................................................65
Why Extrinsic Motivation Matters................................................... 65
How to Become a Super-Producer.................................................... 66
How to Mitigate Intellectual Body Dysmorphia............................. 67

Chapter 9. Learning........................................................ 69
The Greatest Educational Life Hack: Learning Ahead of Time... 69
When Does the Learning Happen?................................................... 73
There is No Such Thing as Low-Effort Learning............................73
The Greatest Breakthrough in the Science of Learning Over the
Last Century......................................................................................... 75
“Following Along” Versus Learning................................................. 77
The Vicious Cycle of Forgetting........................................................81
The Vicious Cycle of Context Overload........................................... 84
Prereq Yo’ Self Before You Wreck Yo’ Self.......................................85
The Efficient Learning Loop..............................................................86
Schooling Versus Talent Development.............................................87
A Sanity Check for Effective Study Techniques..............................90
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Preface

Since summer 2024 I've written a ton of scattered pieces on

upskilling. I recently cleaned them up and pulled them all
together into this little booklet.

It’s still somewhat of a work in progress and I'll be continually

extending and refining it in the future, but I feel like it does a
decent job of bringing together a lot of previously scattered
writing into some sort of more cohesive whole.
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Chapter 1. Consistency

You’re Not Lazy, You Just Lack a Habit

If you’re struggling to stick with demanding forms of practice,

then temporarily forget about efficiency and just build a habit
with some less effective but more enjoyable form of practice.
Although the ultimate goal is to train efficiently and get the
largest possible performance gain out of your limited training
time, that's going to feel taxing, and you might not want to
work that hard at first – not because you're inherently lazy, but
because you haven’t built a habit. You eventually want to get to
the point where performance improvement is your primary
focus and fun is a second-order optimization, but it’s okay to
optimize for fun at the beginning to help you build a habit.

Consider strength training, for example. If you’re just starting

out, but you’re not looking forward to lifting heavy-ass weights,
then that’s okay! You don’t have to lift them yet. Your #1 focus
should be just getting your ass into the gym and doing some
kind of activity that loosely qualifies as exercise. After a week
of, say, shooting hoops, you might be motivated to try some
bodyweight exercises – and then the following week maybe
some light weightlifting, and maybe the week after that you’ll
be ready to challenge yourself by putting some serious weight
on the bar.
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It’s the same way with anything else – for instance, learning
math. If you don’t feel motivated to solve a high volume of
problems that are challenging enough to make you mentally
sweat, that’s okay. You can start off watching math
edutainment videos and exploring Wikipedia. The next week,
maybe try to solve some “math meme” problems each day (and
look at the comments to check if you got it right), and the
following week, maybe work out some easy arithmetic or
algebra problems each day (stuff that you still remember fairly
well but haven’t done in a while). By that point you’ve gotten
yourself into the metaphorical weight room, doing some light
lifting, and you’re ready to put some serious weight on the bar.
And that’s when you start working through a structured
curriculum that engages you in taxing practice to pack the
maximum possible learning into your practice time.

Once you get to that point, you’ve built a habit, and you need to
do everything in your power to maintain it. If you want to take
a day off, just do a quick 10 minutes – something that feels
negligible but keeps the habit going. The habit is a
psychological force field that protects you from all sorts of
negative feelings that try to dissuade you from training.

In summary: You're not lazy, you just lack a habit. So start

simple, whatever gets the ball rolling. (But if you know this and
you’re still unwilling to build a habit… then yeah, you’re lazy.)

Don’t Have a Passion? Go Create One.

Be disciplined, set up a habit, compound compound compound.

Develop a relationship with it, put in extra time when you’re
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bored, come to it when you need an emotional outlet. Trust that

it will grow on you and seep into your identity as you spend a
lot of time practicing and developing serious expertise.

It’s just like developing a close human relationship. You might

not have a strong bond with the person initially, but you get
along “enough” at the beginning, and over time you get to
know each other so well, you go through so much shit together,
that you are inseparable.

And don't worry about the long-term too much. The person
who became your best friend, you probably didn't know it the
day you met them. You probably got to know them better and
better, week by week, month by month, until at some point you
realized you couldn't imagine life without them. It's the same
way with creating a passion. If you keep on making short-term
progress then the long-term will sort itself out.

Make the Habit Easily Repeatable

Don’t make it such a “big thing” that you do it one day and
dread doing it the next day. You know what happens to people
who start their New Year’s weight loss resolution off with 3
hours at the gym every day? They come for one day and then
don’t come back! So don’t do that. Instead, start out with a
volume of work that’s small enough that you don’t dread doing
it again the next day.

It doesn’t matter if the volume of daily work is too small to

achieve your long-term goals in the timeframe you want.
Eventually, as you build up a habit and your mind and body
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adapt to whatever it is you’re doing, it will feel easier to ramp

up the volume of work until you’re moving at a pace that puts
you on track to accomplish your long-term goals.

So don’t worry about total volume of work at the beginning.

Just focus on consistency. As the habit sets in and you adapt,
you’ll find it easier to increase your volume of work. And as the
habit settles into your identity, you’ll actually want to increase
that volume of work.

The Hardest Part is Just Getting Started

Most skills can be trained. But serious training usually isn’t

pleasant, so most people don’t do it. That doesn't mean there's
little benefit to training them. It just means lots of people
aren't willing to put in the work to capitalize on said benefit.

But the thing is, the hardest part is always just getting started.
If you suck at writing, then just sit down and write for 15
minutes each day. It might be unpleasant fishing for cohesive
thoughts in your brain stew, pulling them out, and translating
them into text. But that doesn’t mean it will always feel that
way.

As you practice again and again, it will feel easier over time.
And as it feels easier you’ll free up more and more mental
bandwidth to notice areas for improvement. And you’ll get
better. Will you become a world-class writer? Who knows.
Probably not. But will you open up opportunities that were
previously closed to you? Probably.
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And who's to say the training will actually be unpleasant?

When you're not looking forward to it, you might think that
negative feeling is going to intensify during your (physical or
intellectual) workout, but often it just dissipates and you feel
great 5 minutes in. Procrastinating builds up the dread but just
getting started often makes it dissipate.

Don’t Overreact to Bad Days

Even if you’re making the right decisions, you can still have bad
days. So it’s important to stay consistent and not let a single
bad outcome derail you.

Yes, that can be difficult psychologically. We tend to be

risk-averse and overreact to negative outcomes. But it can help
to zoom out and look at your progress on a longer timescale.

At the same time, though, you can’t use that as an excuse to

avoid measuring progress and thinking critically about it. Every
time there’s a bad outcome, you have to ask whether there’s
anything you can learn from it to carry into the future.

Sometimes there’s a flaw in reasoning. Other times there’s a

flaw in assumptions. Perhaps you didn’t have all the key
information to begin with and you should have done better due
diligence. Or perhaps some information revealed itself or
changed after you made the decision but you were too slow to
react.

It’s not worth beating yourself up over mistakes, unless they’re

mistakes you’re repeating over again. One-and-done mistakes
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won’t keep you from making progress in the long-term, but

repeated mistakes will.

Aim for Virtuous Cycles

It’s a fact of life that things compound. You improve one aspect
of your life, it’s going to have carryover effects, and that other
aspect is going to have carryover effects, and so on.

It’s important to take advantage of these feedback loops and

orient them in a positive direction. Because if they’re not
moving you in a positive direction, they’re moving you in a
negative direction. There is no stable equilibrium.

You’re going to get pulled into self-perpetuating cycles whether

you like it or not. So it’s important to do all you can to get
yourself pulled into virtuous cycles, not vicious cycles.
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Chapter 2. Skills

The Importance of Hardcore Skills

Hardcore skills are the biggest bottleneck to improving one’s

life and society in general. It doesn’t matter which of those
things (yourself versus society in general) you’re more focused
on – hardcore skills are always the answer.

So many people want to have high impact and improve the

world (and their own lives) in a big way. But desire is not
enough. You typically can’t do anything big unless you have big
skills. I say “typically” because sure, some people get really
lucky being born into the right family in the right place at the
right time and enjoy an outsized impact despite not having
built up their skills as much – but even for those people, the
difference between a relatively large impact (relative to other
people) versus an absolutely large impact (“put a dent in the
universe”) still comes down to skill-building.

Hardcore skill development is also one of the greatest social

mobility hacks. Even if your family is not well-connected, you
can make up for it by developing real skills. Sure, you have to
develop more skills than well-connected people to reach the
same level of opportunity, and you’re going to have less
guidance developing those skills and finding your way to the
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arena – but once you’re in the arena, those extra skills pay big
dividends.

The “Alien-Level Skills” Hack

Having strong technical chops can be a gigantic power-up that

sets you apart. You get to provide value that nobody else can,
and you get recognized for it. That’s what happens when you
equip yourself with alien-level skills and solve problems for
Earthlings.

But one of the things that keeps people from capitalizing on

this hack is they don’t invest in building broad technical
foundations. For instance, a common argument against
building broad mathematical foundations is “why not just wait
to learn math until you have a job in a math-adjacent field, and
then backfill all the useful math as you encounter specific
problems on the job?”. On the surface, that might sound like a
way to reduce the amount of work that it takes to develop
alien-level math skills that set you apart and boost your career.
However, in practice, this “wait to backfill” approach greatly
REDUCES your chance of being able to capitalize on the
alien-level skills hack. Here’s why.

If you work in a math-adjacent field and don’t have much math

background, then:

1) You’ll underestimate how often mathy tasks come up. Even

when one does, without plenty of math background, you
probably won’t realize how mathy it is.
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2) Even if you do come across a task you know is mathy, you

likely won’t have enough math background to even realize what
mathy approach you need to take to complete the task (i.e.,
what specific math do you have to apply or spin up on).

3) Even if you do know what mathy approach you need to take,

the task might be handed off to someone else who already has
more math background (because it will take them much less
time to spin up and solve the problem).

4) Even if there is nobody else to steal the task, if there is time

pressure, then you might not have any time to actually carry out
that mathy approach. This can happen in a couple different
ways:

●​ Defaulting to cumbersome methods: "We don't have

time for you to spin up on math for an ideal solution, we
need to ship NOW. Just do the best you can in a week using
what you currently know, even if it's not great, and we'll
figure out a way to patch over whatever issues come up
afterwards, even if the patches are complicated."​

●​ Passing up the problem: "This would have been a great

opportunity if we had someone who could solve this problem
reasonably quickly, but we can't spend tons of time on it, so
we're unfortunately just going to have to pass it up and focus
on things that are closer to what we're able to do at the
moment."

I’ll end with one caveat: depending on the field you’re going
into, you typically CAN do a reasonable amount of scoping
down. For instance, if you want to work on ML/AI then you
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probably don’t need to learn Abstract Algebra. But at the same

time, there is still a mountain of math you’d benefit from
knowing. Many topics in calculus, linear algebra, and
probability & statistics tend to come up.

There’s a balance to be had; there is an appropriate level of

scoping. On one hand, you CAN skip out on math that is
largely irrelevant for your math-adjacent field – BUT, whatever
math tends to show up in your field in general, if you don’t have
broad knowledge of it, you’re going to struggle to pull off the
alien-level skills hack. You CAN scope down and discard math
that doesn’t come up in your field, BUT if you want to pull off
the alien-level skills hack, you should NOT scope down further
and discard math that doesn’t seem to appear in a specific
problem.

The Importance of Having Your

Prerequisites In Place

Having your prerequisites in place is the difference between

something seeming confusing and inaccessible versus “wait…
that’s all it is?”. It’s easy to think you lack learning ability when
really you just lack prerequisite knowledge. Differences in
learning ability do exist, but they’re often conflated with
presence or absence of prerequisite knowledge. (Beware: it’s
also easy to think you’re wicked fast when really you’ve just
mastered more prerequisites than your peers.)

More generally, the way to “unlock” things that feel

inaccessible to you is to shore up your prerequisite abilities.
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This applies not just to learning tasks, but also to

opportunities. Everybody knows that luck is where preparation
meets opportunity, but fewer people understand that if you
don't have the prerequisite abilities in place that prepare you to
capitalize on an opportunity, you probably won’t see it in the
first place. Imagine how many opportunities you’re blind to
because you don’t have the prerequisite knowledge to even see
them whiz by.

Fortify Your F*cking Fundamentals

To have enough mental bandwidth to think deeply about what's

going on in any complex field, you need to be very comfortable
with the fundamentals. And that's not going to happen if the
fundamentals you need are close to the edge of your ability.
Sure, you can execute at the edge of your ability… but not
*comfortably*, and that makes all the difference. Your
high-level train of thought is going to get continually derailed
by the low-level details you have to manage. You're going to
have a hard time seeing the forest for the trees.

To hammer in your fundamental skills to the point of

comfortable execution, it helps to not only get plenty of
practice with those skills, but also layer plenty of more
advanced skills on top.

For instance, consider figure skating. Yes, figure skaters get

really good at skating in part because they skate a lot, but it's
not just that. It's also that they continually layer more advanced
jumps and spins. Skating around the rink will get you to a
decent level of comfort in your basic skating skills, but being
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able to land jumps and spins will force a whole new level of
robustness and fault-tolerance in those underlying skills. It's
like those robot testing demonstrations where all the engineers
stand in a circle shoving the robot around. It's not enough to
just test that the robot can follow a predetermined path. You
gotta bang it around a bit to make sure it's resilient.

It all comes down to forcing structural integrity of underlying

skills. When you build advanced features on top of a system,
they sometimes fail in ways that reveal previously-unknown
foundational weaknesses in the underlying structure. This
forces you to fortify the underlying structure so that the system
can accommodate new elements without compromising its
integrity. And when you fortify the system to execute advanced
tasks successfully, it becomes capable of executing simpler
tasks *comfortably*. What's more, fortifying the underlying
structure often requires improving its organization and
elegance, which, in the context of knowledge, is what produces
deep understanding and insight.

Actively Doing is the Key to Alpha

Actively doing (as opposed to passively consuming) is not just

the key to effective learning. It’s also the key to alpha, i.e.,
developing an edge.

Lots of people consume. Fewer people actively do. Even fewer

people attempt challenging things. And even fewer people than
that build up the foundational skills needed to succeed in doing
those challenging things.
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And what’s more: alpha compounds. When you succeed in

doing a hard thing, the learning and resources you acquire
position you to succeed in doing even harder things and
acquiring even more alpha. In other words, your edge gets
sharper – not duller – with use.
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Chapter 3. Discipline

The Magic You’re Looking For is in the

Full-Assed Effort You’re Avoiding

30 minutes of fully focused deliberate practice 4 days per week

can have you making serious progress towards most learning or
fitness goals. But it has to be fully focused – a “full-assed”
effort – and you have to be continually upping the level of
challenge as your capabilities increase. You have to work
intensely enough that you come out of each session seriously
winded. Meaning that either your brain feels like mush or your
body feels like jell-o.

When someone fails to make decent progress towards their

learning or fitness goals and cites lack of time as the issue,
they’re often wrong. It’s often not lack of time but rather lack
of willingness to put forth a full-assed effort under a
continually increasing level of challenge.

If you put in a half-assed effort then you get a quarter of the

results at most. That’s what causes the purported lack of time.
To get the equivalent of 30 min full-assed, you have to put in at
least 2h half-assed, which you quite reasonably might not have
time for. Or you put in 30 min half-assed and get the equivalent
of 7.5 min full-assed, which doesn’t move the needle fast
enough on your progress for you to reach your goal in a
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reasonable timeframe. The magic you’re looking for is in the

full-assed effort you’re avoiding.

At Some Point Doing the Hard Thing

Becomes Easier Than Making the Hard
Thing Easier

The condition for getting yourself to do something is simple:

it’s just internal willpower ≥ external friction. If that condition
is false then the way you make it true is by decreasing friction
and/or increasing willpower.

It’s helpful to think of this like balancing a budget: willpower is

like your income and friction is like your spending. If your
budget isn’t balancing then the first thing to do is cut out any
dumb costs. Is there anything dumb about your environment
that’s causing needless friction? Cut it out. Your life is like a
big codebase – if you’re struggling to implement a new
behavior in some area, then refactor that area to make it easier
to build on.

But at the same time, you can only take cost-cutting so far.
There are always going to be some basic expenses you have to
cover. And there’s a limit to how easy you can make it to add a
new feature to the codebase. You can refactor all you want but
there’s always going to be some amount of complexity inherent
to the new feature.

The trick is to be honest with yourself about when you start

asymptoting off in your attempts to reduce environmental
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friction. At some point doing the hard thing becomes easier

than making the hard thing easier. And that’s when you have to
muster up the willpower to overcome whatever friction is left
over. That’s when you have to say “enough refactoring, time to
lock in and implement this sucker.” That’s when you have to
change your focus from cost-cutting to producing extra
income.

In any journey, you can chart an easier, more efficient course,

but there’s always going to be some serious trekking involved.

How to Cultivate Discipline

When there’s something that you know you should do, but you
can’t get yourself to do, it means some habit is pulling you away
from doing it. So what you need to do is tear down the
unproductive habit and build up a counter-habit whose gravity
eventually becomes strong enough to completely overtake the
original habit. You try to disrupt your momentum on your
negative habit and create momentum towards a positive habit.
And while you might not be able to do this all in one fell
swoop, what you can do is iterate on it and gradually ease into a
transition one little step at a time.

Here’s a concrete example which may or may not apply to you

but hopefully it will illustrate the main idea. Let’s say you’re
having trouble cultivating discipline with exercising every day.
The first question is: what’s keeping you from exercising?
Maybe you plan to exercise after work but then things come up
and you always find an excuse. Okay, so do it first thing in the
morning. Why aren’t you already doing it first thing in the
28 | Advice on Upskilling – Working Draft

morning? Let’s say it’s because you have a habit of waking up

15 minutes before you have to leave for work and there’s not
enough time for exercise.

That habit is pulling you away from your goal of daily exercise.
So you need to gradually replace it with a more productive
habit. Maybe instead of waking up 15 minutes before work, you
wake up 20 minutes before and spend 5 minutes doing jumping
jacks as soon as you get out of bed. (Or if 5 minutes is too
daunting then maybe you start with just 1 or 2 minutes and
gradually build up to 5 minutes.) After enough days of waking
up 5 minutes earlier for 5 minutes of jumping jacks, you’ll have
created a “new normal” morning routine, and you’ll find it
within yourself to wake up another 5 minutes earlier and
replace your 5 minutes of jumping jacks with a 10-minute run.

You keep going this direction, gradually tearing down your

habit of waking up just before you have to leave, and building
up a habit of waking up earlier and earlier and doing more and
more exercise with that extra time. Eventually you reach your
desired fitness routine goal and then you just maintain that
habit into the future.

Keep Your Hands On The Boulder

People will do unbelievable mental gymnastics to convince

themselves that doing an easy, enjoyable thing that is unrelated
to their supposed goal somehow moves the needle more than
doing a hard, unpleasant thing that is directly related to said
goal.
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If you want to move the needle on a goal, you have to

concentrate your efforts directly on that goal. You can exhaust
yourself doing other things, fulfilling other responsibilities
and/or moving the needle on other goals – but at the end of the
day, each goal has its own needle, and the general feeling of
exhaustion doesn't imply you've successfully moved any needle
in particular.

This can be a hard truth, especially for people who have taxing
responsibilities that are separate from their aspirational goals.
But the only way to achieve those aspirational goals is to
somehow find it in oneself to directly move the needle on them.
There is no other way.

Just Do The F*cking Work

If you want to develop serious skills, you have to engage in

intense, taxing workouts. Amateurs sometimes make up all
sorts of excuses for why this rule doesn't apply to them, but real
pros don’t try to weasel their way out of the hard work.

You think you’re too good for the grunt work? Too smart to
listen to your coach’s feedback? Then what are you waiting for
— go on, succeed all by yourself in your current state. Either
prove your inherent greatness, or fail and get your ass handed
to you enough times to knock some humility into your head.

At the end of the day you can either waste time debating your
coach on the training regimen, or you can use that time to just
put your head down and do some f*cking work. One of those
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actions will turn you into a pro; the other will keep you
tethered to amateur level for the rest of your life. It’s your
choice.

You want outsized results? Then you’re going to have to put in

an outsized amount of work. Achievement, expertise, greatness,
whatever the hell you want to call it — it doesn’t happen
naturally. It’s about transforming yourself from normal to
abnormal in ways that confer a competitive advantage. There’s
nothing natural about it.
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Chapter 4. The Grind

The Most Superior Form of Training

In the field of talent development, there is absolutely no debate

about the most superior form of training. It’s “deliberate
practice”: mindful repetition on performance tasks just beyond
the edge of one’s capabilities. Deliberate practice is about
making performance-improving adjustments on every single
repetition. Any individual adjustment is small and yields a
small improvement in performance – but when you compound
these small changes over a massive number of
action-feedback-adjustment cycles, you end up with massive
changes and massive gains in performance.

Deliberate practice is superior to all other forms of training.

That is a “solved problem” in the academic field of talent
development. It might as well be a law of physics. There is a
mountain of research supporting the conclusion that the
volume of accumulated deliberate practice is the single biggest
factor responsible for individual differences in performance
among elite performers across a wide variety of talent domains.
(The next biggest factor is genetics, and the relative
contributions of deliberate practice versus genetics can vary
significantly across talent domains.)
32 | Advice on Upskilling – Working Draft

Why, then, does anyone seeking to attain a high level of skill

engage in forms of practice other than deliberate practice? The
answer might be the most hard-hitting 2 sentences in all of
talent development research: "...[D]eliberate practice requires
effort and is not inherently enjoyable. Individuals are motivated to
practice because practice improves performance" (from Ericsson,
Krampe, & Tesch-Romer, 1993, in The Role of Deliberate Practice
in the Acquisition of Expert Performance). In other words,
maximal performance does not happen naturally as a result of
maximizing other things like enjoyment, comfort, convenience,
and ease of practice. In fact, maximal performance is at odds
with some of these things. Sacrifices must be made.

Lots of people are unwilling to make sacrifices to engage in

deliberate practice – and that’s fine. That’s a personal value
judgment. But the problem is that many of these people still
claim that they are doing their best to develop their talent.
Typically, they will cut corners on one of the two requirements
of deliberate practice – “mindful” and “repetition” – and then
resist any form of objective, quantifiable measurement of their
performance that would expose the ineffectiveness of their
practice.

Deliberate practice is not mindless repetition. If you’re doing

the same thing over and over again, then you’re doing
deliberate practice wrong. Deliberate practice is about making
performance-improving adjustments on every single repetition.
Any individual adjustment is small and yields a small
improvement in performance, but when you compound these
small changes over a massive number of cycles, you end up
with massive changes and massive gains in performance. None
 Advice on Upskilling – Working Draft | 33

of this happens if you’re mindlessly doing the same thing over

and over again without making adjustments.

Likewise, even if you’re mindful during practice, you can’t

skimp on repetition and still call it “deliberate practice.”
Deliberate practice necessitates a high volume of
action-feedback-adjustment cycles in every single training
session. Otherwise, the compounding doesn’t happen. Any
activity that throttles the number of these cycles cannot be
described as deliberate practice.

Many heated debates in education stem from these

misinterpretations of deliberate practice. Mindless repetition,
doing the same thing over and over again without making
performance-improving adjustments, is not deliberate practice.
Likewise, any activity that throttles the volume of
action-feedback-adjustment cycles (e.g., excessively challenging
problems, or think-pair-share type of stuff) is not deliberate
practice.

Outsized Success Requires Outsized Work

You want to do something that sets you apart? You’re going to

have to work harder than most. There is no way around it. If
you think you can achieve outsized success without putting in
an outsized amount of work, then you will never achieve your
goals because you will never transform yourself into a person
who is capable of achieving them.

And guess what? It’s not enough to simply work hard. To

achieve outsized success, it’s critical to not only put in enough
34 | Advice on Upskilling – Working Draft

time and effort, but also to work productively. You have to

work hard AND work smart. And furthermore, work in a
direction where you have some competitive advantage (or, at
least, you’re not at a disadvantage). Part of this work involves
engaging in activities that maximize the likelihood of you
getting some lucky breaks. You have to work to maximize your
luck surface area.

Transformation Is Discomforting

If you don’t push yourself to perform beyond your level of

comfort, you don’t improve your performance. Simple as that.
Why? Because performance improvements come from your
body adapting to additional strain. No strain, no gain.

Strain can be unpleasant. It’s taxing and it leaves you fatigued.

You may feel weak, untalented, even dumb if you’re training an
intellectual skill such as math. But it’s completely necessary. To
avoid the feeling of strain is to avoid the process of adaptation,
and thus, to avoid performance improvement.

What you want is a continual cycle of strain and adaptation.

That’s true in athletics, and it’s just as true outside of athletics.
You feel weak while exercising but you come back stronger.
You feel dumb while studying but you come back smarter. The
thing to remember when studying is that you are physically
changing your brain to execute more complicated cognitive
tasks. At a fundamental level it is just like lifting weights or
practicing gymnastics. The keys to effective training are the
same, and so is the feeling of effective training.
 Advice on Upskilling – Working Draft | 35

Transformation is discomforting. But keep in mind that while

discomfort is necessary for performance improvement,
discomfort alone does not always indicate that you’re engaging
in performance-improving activities. You also need to be able
to overcome the challenge that’s inducing the discomfort.
Think of it this way: dropping a 500lb-loaded barbell onto the
shoulders of a novice lifter would be neither comforting nor
productive. They’s get crushed, develop no strength, and the
only thing they’d learn from the experience is that they hate
strength training. The same is true for too-difficult math
problems, too-difficult pieces of music… you get the idea.

Enjoyment is a Second-Order Optimization

If you are seeking to maximize your “bang for buck” in terms of

learning per unit practice time, then enjoyment is a
second-order optimization that is often at odds with the
first-order optimization, namely, deliberate practice. A key
feature of deliberate practice is that it requires continually
practicing beyond one's area of comfort, and this tends to be
more effortful and less enjoyable (as one would expect of
something that is by definition uncomfortable).

If you want to maximize your learning efficiency: 1) engage in

deliberate practice, and 2) make the deliberate practice as
enjoyable as possible (or, equivalently, as least unpleasant as
possible). Ranked by efficiency, here’s the whole spectrum:
enjoyable deliberate practice > unpleasant deliberate practice ⋙
other enjoyable forms of training > other unpleasant forms of
training.
36 | Advice on Upskilling – Working Draft

Now, this is not to say that enjoyment is unimportant. If

deliberate practice is not enjoyable for someone, then other
enjoyable activities can sometimes be useful for increasing
motivation and softening the discomfort associated with
deliberate practice. But it’s important to realize that fun is a
supplement, not a substitute, for deliberate practice.

Additionally, while deliberate practice is inherently

uncomfortable, you can normalize yourself to it via repeated
exposure – and once you begin to see your tiny improvements
compounding into massive long-term gains, it can feel
satisfying. As the saying goes, “nothing succeeds like success.”

Ability is Built, Not Unlocked

One of the most harmful myths in education is that ability is

something to be “unlocked” by curiosity and interest (which
seems easy), not something “built” by deliberate practice
(which seems hard). It’s so funny when you imagine what this
would sound like coming from an athletic trainer: “You want to
get really good at basketball? Forget about practice drills – you
were born to ball; all you need to do to unlock your inner baller
is come in with the right attitude and play some pick-up ball at
the park.”

This is not to say that curiosity and interest don't matter. Just
that these things do not themself build ability. They don't move
the needle directly. They motivate people to engage in
deliberate practice, which is what directly builds ability.
Curiosity and interest “grease the wheels,” so to speak, but they
don't actually move the wheels.
 Advice on Upskilling – Working Draft | 37

What Max-Efficiency Training Feels Like

There is sometimes a disconnect between what people think

max-efficiency training should feel like, and what it actually
feels like. It’s common to think that max-efficiency learning
should feel maximally scaffolded, perfectly smooth and easy the
whole way through.

While this is more true than not, it misses an important

nuance: max-efficiency training should feel just-enough
scaffolded that the learning tasks are challenging yet still
achievable in a reasonably quick timeframe. When you’re
developing skills at peak efficiency, you are maximizing the
difficulty of your training tasks subject to the constraint that
you end up successfully overcoming those difficulties in a
timely manner.

A noteworthy corollary is that you are also minimizing your

confidence in your ability to complete the training tasks (again
subject to the constraint that you end up successfully
completing them in a timely manner).

In this way, confidence becomes more of a “hindsight” thing

than an “in-the-moment” thing. If you feel confident while
engaging in max-efficiency training, it’s not because the task in
front of you seems easy relative to your abilities, but because
you’ve been in situations before where tasks felt challenging
relative to your abilities but you’ve always managed to come out
successful.
38 | Advice on Upskilling – Working Draft

The Necessity of Grinding Through

Concrete Examples Before Jumping Up a
Level of Abstraction

What a lot of learners fail to understand is that grinding

through concrete examples imbues you with intuition that you
will not get if you jump directly to studying the most abstract
ideas.

If you go directly to the most abstract ideas then you’re

basically like a kid who reads a book of famous quotes about
life and thinks they understand everything about life by way of
those quotes. The way you come to understand life is not by
just reading quotes. You have to actually accumulate lots of life
experiences. And you might think you understand the quotes
when you’re young, but after you accumulate more life
experience, you realize that you really had only the most naive,
surface-level understanding of the quotes back then, and you
really had no idea what the hell you were talking about.

It’s the same way in any subject – even math, where

information can be packaged into clean theorems that are
provably correct. In general, the purpose and power of an
abstract idea is that it compresses a zoo of concrete examples.
But if you haven’t built up that zoo of concrete examples then
you miss out on that power. If you study the theorems but shy
away from grinding messy concrete problems, then you will
never truly gain the deep intuition to know what the hell you’re
talking about.
 Advice on Upskilling – Working Draft | 39

Be Willing to Do Tedious Work

In order to get a good sense of what really matters, you have to

get your arms around the problem, which typically requires
getting your hands dirty and doing enough manual grunt work
to develop intuitions and strong gut feelings.

Many people justify avoiding the grunt work on the grounds

that it’s tedious and they already have it all figured out in their
head, not realizing that the contour of the problem space in
their head doesn’t match up with reality.

Their reasoning tends to be sound, but it’s the assumptions

that get them. There’s some parts of the real-life problem that
they haven’t loaded up in their head. Sometimes there are
important things they think are negligible, sometimes
negligible things they think are important.

Don’t Undervalue Turning Up the Dial on

Your Grind, but Don’t Overvalue the Last
Turn

Regret minimization is often used to justify leaving a

comfortable situation to grind towards an life-changing
transition is uncertain and difficult in the short term. This
might seem like flipping a switch towards 100% grind,
constantly pushing the boulder, but it’s important to keep in
mind that regret minimization cuts both ways. Yes, grind grind
40 | Advice on Upskilling – Working Draft

grind, but also don’t forget to take breaks to spend time with
people you care about, especially around big events or when
you’re not going to see them again for a while.

If you’re anything like me and have a nagging feeling that you

should be making progress on “the thing” 100% of the time,
what might help justify taking breaks is to think about relative
speed increases: if you’re pushing on the needle X% of the time,
what kind of speed multiplier are you leaving on the table?

●​ If you’re pushing 25% of the time, then there would be

a 4x multiplier by pushing 100% of the time. 4x
speedup is the difference between a decade of work vs
a couple years.
●​ If you’re pushing 50% of the time, then the multiplier
drops to 2x. For me, at least, that’s still leaving a lot on
the table.
●​ If you’re pushing 80% of the time, then the multiplier
drops to 1.25x. You’re getting fairly close to max
capitalization.
●​ If you’re pushing 90% of the time, then the multiplier is
down to 1.1x. It’s basically max capitalization with a
slight rounding error.

Sure, if there is a make-or-break moment in your grind, then it

might be worth temporarily turning the dial up to 100% to try
to capitalize on it. But in the long run, outside of those
situations, that last turn of the dial from 90% to 100% is not
going to change the overall outcome – all it will do is create
regret in other areas of your life. And that regret does not stay
external. Even if you try to compartmentalize it, it will find a
 Advice on Upskilling – Working Draft | 41

way to seep into your whole, detracting from your motivation &
productivity, eventually conspiring to derail you early.

Failure Is NOT the Key to Success

Failure gets over-emphasized as being the key to success.

LEARNING is the key to success. Failure only moves you
towards success to the extent that you learn from it.

You should never fail twice for the same reason. Correcting a
mistake will move you closer to success, but making the same
mistake over and over again will lock you into losing.

Focus Less on Feelings and More on

Measurable Progress

Anyone who knows about deliberate practice knows how

important it is to spend your time practicing at the edge of
your abilities. But how do you really know when you’re at the
edge? Most people can tell when their practice is too easy –
you’re able to complete tasks effortlessly while thinking about
other things. But what about when your tasks are too hard?
That’s often less obvious. Practice is supposed to challenge you,
but how hard is too hard?

Here’s my rule of thumb: Focus less on feelings, and more on

measurable progress. When your practice is too difficult, you’re
going to be running in place and not making much measurable
progress.
42 | Advice on Upskilling – Working Draft

Think about what happens if you try to work out with a weight
that’s too heavy for you to lift. Yes, you might be able to tell
that it feels excessively strenuous, but what really gives it away
is that despite trying your hardest, you’re not able to lift the
weight. And not only are you unable to lift the weight, but
you’re not getting any closer to doing so.

The same thing happens if you work on a math problem or

coding project that’s too hard. Your brain goes into overdrive,
and you work on it for a long time, but you just don’t really get
anywhere with it. You don’t solve the problem, you can’t point
to any concrete skills you acquired during the process.

So, if you want to practice effectively, here are some things you
absolutely must do: 1) have some concrete way of measuring
your progress, 2) make sure that whatever you’re doing is
actually increasing that progress, and 3) make sure that the
progress is increasing fast enough that you’ll reach your goal in
a reasonable (but realistic) amount of time.

By the way, if your goal is really lofty, then a reasonable amount

of time might still be a long time – so long that it’s hard to tell
whether you’re progressing fast enough. So if you have a lofty
long-term goal, I would also recommend to decompose it into a
series of shorter-term goals where it’s totally obvious whether
you’re making fast enough progress to reach the next
short-term goal in a timely manner.
 Advice on Upskilling – Working Draft | 43

The Problem with Overly Difficult Problems

It’s tempting to think that to train up your skills, you should be

focusing on the hardest training problems. But here’s the thing
about “think really hard, struggle for a long time, solve it once
in a while but usually look up the solution” problems: they can
be fun (for a certain type of person), but they’re not an efficient
way to learn.

Approaching challenging problems without having the

subskills down pat is like jumping into a game of basketball
without having developed dribbling and shooting skills. It
might feel fun but you’re just going to be whiffing every shot
and getting the ball stolen from you. You might make one layup
the entire game and feel good about it, but that’s barely any
training volume.

It’s like going to the gym to lift weights but only eeking out a
single rep over the entire course of your workout. You need to
be banging out more reps if you want to get stronger, and the
only way you can bang out those reps is by working with a level
of weight that’s appropriate for you.
44 | Advice on Upskilling – Working Draft
 Advice on Upskilling – Working Draft | 45

Chapter 5. The Journey

The 3 Stages of Talent Development

Across various talent domains, the journey to developing a high

level of talent occurs through a similar general process and can
be roughly divided into three stages. That's what Benjamin
Bloom discovered in the 1980s while studying the training
backgrounds of 120 world-class talented individuals across 6
talent domains (piano, sculpting, swimming, tennis, math, and
neurology). Below are summaries of the stages:

●​ Stage I: Fun and exciting playtime. Students are just

starting to develop awareness and interest in the talent
domain. The teacher provides copious positive
feedback and approval and encourages students to
explore whatever aspects of the talent domain they find
most exciting. Students are rewarded for effort rather
than for achievement and criticism is rare.

●​ Stage II: Intense and strenuous skill development. Students

are fully committed to increasing their performance.
The teacher becomes or is replaced by a coach, who
focuses on training exercises where the sole purpose is
to improve performance. These exercises are
demanding, and the coach provides constructive
criticism to help the student perform the exercises
46 | Advice on Upskilling – Working Draft

properly. Positive feedback is provided in response to

achievement; effort is assumed.

●​ Stage III: Developing one’s individual style while pushing

the boundaries of the field. Students are proficient in all
the foundational skills in the talent domain. They are
so committed that they center their entire lives around
the talent domain, no matter the sacrifice, and typically
work with a world-class expert in the talent domain.
The expert helps the student identify and lean into
their individual strengths so that they can excel beyond
perceived human capabilities.

However, there are several failure modes that one can run into
when attempting to make the journey through these stages:

●​ Failure Mode 1: The Permastudent. The permastudent

perpetually avoids the leap into creative production,
opting instead to “expand sideways” and acquire skills
that are not foundational for their talent domain.​

●​ Failure Mode 2: The Wannabe. The wannabe jumps the

gun on creative production before their foundational
skills are in place. They build a portfolio of work that
lacks substance and is made trivial by foundational
knowledge. Not only is it cringe, but it also has high
opportunity cost because all this time could be put to
better use actually acquiring said foundational
knowledge.​

●​ Failure Mode 3: The Dilettante. The dilettante cuts their

journey even shorter than the permastudent – they
 Advice on Upskilling – Working Draft | 47

never even make it past playtime, they never commit to

serious foundational skill development in anything.
The dilettante spends all their time in the land of
diminishing returns, engaging in perpetual playtime
across a large number of talent domains.

There Are No Shortcuts in Talent

Development

When it looks like someone progressed so fast they “must”

have taken a shortcut, what really happened is they speed-ran
the foundations. Either that or you’re overestimating their
actual ability (likely because they’re exploiting signaling to
trick you).

How can people speed-run the foundations? By way of a more

efficient training environment, advantageous individual
differences leading to more rapid skill acquisition, or by
allocating way more of their time into training than is typical.
Elite performers typically emerge from a combination of all
three of those things.

If You’re Making Silly Mistakes Then You

Need More Practice

Climbing a skill hierarchy like math is not just about

conceptual understanding, it’s also about reliable execution. If
48 | Advice on Upskilling – Working Draft

you’re making “silly mistakes,” then you need more practice,

simple as that.

If you don’t clean up your silly mistakes on low-level skills,

then you eventually hit a wall where no matter how hard you
try, you’re unable to reliably perform advanced skills due to the
compounding probability of silly mistakes in the component
skills.

Think about gymnastics: if you’re “almost” able to land a

backflip, then that’s great – but at the same time, you’re NOT
ready to try any combo moves of which a backflip is a
component. Even if it’s a silly mistake keeping you from
landing the backflip, you still have to rectify it.

And even that’s the most optimistic scenario. Other times, silly
mistakes indicate a deeper conceptual misunderstanding that
you don’t even know you have until you are held accountable
for rectifying those mistakes.

No Train, No Gain

If you’re not measuring performance and taking actions to

improve it then you’re not seriously training, you’re just playing
around.

Which is totally fine at the beginning to get a sense of what you

like and dislike, what you’re willing to commit yourself to
training… but sometime you gotta grow up, ya know?
 Advice on Upskilling – Working Draft | 49

The world rewards those who train. No train, no gain. If you

don’t want to gain anything then sure, just play around forever,
but don’t get mad when nothing comes your way.

You Are a Car

You are a car. You go fast on paved roads and get stuck in mud.

Upgrade your engine to be as fast/powerful as possible, try to

stay on the roads and avoid the muddy zones. (Train your
strengths into superpowers and tailor your environment &
goals to them.)

But at the same time, don’t let a little mud (weakness) derail
your journey. Look for the least muddy zones, try to cross there,
and if you still can’t, then upgrade your tires. (Shore up your
weaknesses so they don’t get in the way of your strengths.)

What to Do When You Hit a Ceiling

In many talent domains, upskilling becomes hard and

unintuitive for everyone at some point, and that point is
different for everyone. In math, for instance – some people start
to experience major cognitive friction in algebra, for other
people it’s calculus, for others it’s real analysis, for others it’s
algebraic topology, for others it’s research-level math, and
there’s even this same gradation even within research-level
math problems. The friction doesn’t create a hard ceiling, a
level at which one is suddenly incapable of further progress,
50 | Advice on Upskilling – Working Draft

but rather a soft ceiling, a point at which the amount of time

and effort required to make further progress begins to
skyrocket until upskilling in that direction is effectively no
longer a productive use of one’s time.

Sometimes people hit a ceiling early due to ineffective or

inconsistent practice techniques. But even if you practice
effectively and consistently, a ceiling still exists. It’s just like
sports: few people practice effectively and consistently enough
to reach their athletic potential, but it’s just a fact of life that
most people could not become professional basketball players
even with 100% effective and consistent practice. You can’t
detect ceilings with 100% certainty, but if you’re practicing
effectively and consistently, and you get stuck in a plateau, and
one-on-one training with a coach or tutor doesn’t break you
out of that plateau, then it’s pretty likely.

The natural question is: what do you do when you hit a ceiling?
In general, when you feel yourself running up against a ceiling
in life, the solution is typically to pivot and into a direction
where the ceiling is higher. For instance, the story of many a
quantitative software engineer goes like this: 1) loved math
growing up and wanted to be a mathematician, 2) realized
during undergrad or grad school that they had lost their "edge"
compared to other aspiring mathematicians, 3) also realized
that they have a knack for coding and interest in some applied
domain, and that the problems that need to be solved there boil
down to interesting math that most people in software don't
have the math chops for, and 4) pivoted in that direction where
their ceiling is higher.
 Advice on Upskilling – Working Draft | 51

Get Yourself In A Position Where You Can

Eat Risk

An underrated component of finding career fit is building

enough savings to pursue opportunities where reward is
uncertain.

Everybody knows that learning / upskilling is a huge

component of career success, but so is the ability to eat risk.

And it’s also a huge competitive advantage. It doesn’t matter

how smart or skilled you are if you can’t eat the risk.

How to Allocate Your Bandwidth While

Searching for Your Mission

If you haven’t found a single mission that you want to focus

your all your bandwidth on, and you’re wondering how to to
distribute your bandwidth so as to pursue multiple interests
while avoiding spreading yourself too thin, then here’s the
allocation I would recommend:

●​ one main focus (workload equivalent to a full-time job),

●​ one semi-focus (workload equivalent to a part-time job),
and
●​ everything else a hobby with whatever time you have left
over. (Your remaining bandwidth is about the equivalent of
another part-time job, so depending on how many things
there are in that "everything else," you might have a small
52 | Advice on Upskilling – Working Draft

number of serious hobbies or a large number of light

hobbies.)

The rationale:

●​ You don't want to spread yourself too thin. You need to be

moving at a competitive speed in at least one direction, i.e.,
your focus.
●​ The semi-focus is like a staging area for something that
you want to eventually merge into your main focus. In
order to successfully complete the merge you're going to
have to develop a serious degree of expertise in it, so it has
to be more than just a light hobby.
●​ Hobbies are mainly things that you just do for fun, but they
can also serve as candidates to replace your semi-focus
once you merge your existing semi-focus into your main
focus.
 Advice on Upskilling – Working Draft | 53

Chapter 6. The Team

If You’re Asking Someone to Be Your Mentor

then You’re Doing it Wrong

The #1 way to increase your productive output is to have it

pulled out of you by an older experienced person who is
unreasonably demanding, incredibly supportive, and has your
deepest respect. Even if you think you’re working hard already,
a person like that can accelerate your output by multiple orders
of magnitude by pointing you in the maximally productive
direction and motivating you to sprint even faster and longer
than you previously believed yourself capable.

But here’s the catch: in order to find that person, be worth their
time, and have that extra productive output pulled out of you,
you typically have to be an incredibly hard and talented worker
in the first place, already producing a solid level of productive
output. You are not going to run into this person if you’re just
coasting. You have to turn the dial up from 1 to 10 yourself, and
hold it there for a while, before you meet the person who gets
you turning the dial up to 100.

If you’re asking someone to be your mentor then you’re doing it

wrong. It should look less like them helping you and more like
you helping them. It starts with you bringing something to the
table. You’re a missing piece in a puzzle that they’re trying to
54 | Advice on Upskilling – Working Draft

solve. Except, you’re not a perfect fit initially. You kind of, sort
of fill some gap initially, and you show signs of being able to
grow to cover the remaining area. And they recognize that, so
they invest their time into helping you grow into that perfect
fit.

As you grow, you also expand into other gaps in the puzzle,
maybe even some that you didn’t anticipate, maybe even some
that your mentor didn’t anticipate. And you grow to fill those
gaps in the puzzle as well. Eventually you cover enough of the
puzzle that you yourself become a puzzle-master looking for
puzzle pieces. And that’s how the cycle continues.

A key takeaway is that when reaching out to someone you hope

to work under, make sure you very clearly communicate the
following: 1) show that you understand what puzzle they're
solving, 2) state what missing piece of that puzzle you think you
can fill, and 3) state what evidence there is that you can fill that
piece.

Put Pressure on Your Boss to Come Up with

More Work For You

One of the best career hacks – especially for a junior – is to

knock out your work so quickly and so well that you put
pressure on your boss to come up with more work for you. It
causes your projects to grow in scale, complexity, and
responsibility.
 Advice on Upskilling – Working Draft | 55

When you’re moving super quickly, your boss can’t spend all
their time communicating hyper-detailed specs to you, so they
have to gradually pull back and offload more of the “scoping
out” work to you. You get more responsibility to carry out the
project with less scaffolding and supervision, and you build
your boss’s trust in your ability to execute.

And as you keep executing and forcing your boss to come up

with more stuff for you to work on, your boss eventually gets to
the point of thinking “I don’t have time to scope out more work
for them because I need to get X, Y, and Z done… huh, you
know, things X and Y are kind of advanced but I bet they could
do thing Z for me with a little bit of coaching.”

Basically, you put so much pressure on your boss to come up

with work for you to do, that your boss starts giving you work
that they themself need to do soon, which is really the exact
kind of work that’s going to move your career forward.

(Note: There's an assumption here that your boss and

organization are well suited for rapid career growth. If that
assumption is false, then the very first step is to get yourself
into a position where that assumption becomes true.)

Get On the Right Team

When you’re on the right team, your working hard inspires

your teammates to step up their game. When you’re on the
wrong team, your working hard causes your teammates to lean
back, do less, and let you make up the difference.
56 | Advice on Upskilling – Working Draft

If you want to create serious change then you need to get on

the right team. You can be the most committed and capable
workhorse on the planet, but if you’re on the wrong team, the
only thing you’ll change is your team’s allocation of work (i.e.,
now you do more work and other people do less).

You need to get on a team where increasing your effort

produces an outsized gain in your team’s collective effort. Why
“outsized”? Because when you’re on the right team, stepping
up your game will inspire your teammates to step up their
game as well.

Competition as a Means of Collaboration

Competition and collaboration might sound like opposites,

when there’s actually a way in which competition can be
reasonably viewed as a means of collaboration. It’s when you’re
engaged in friendly competition with people that you’re
connected to and care about, where the point is to motivate
each other and make each other better.

It's kind of like what you would expect on a serious sports

team. During practice, teammates will be competing against
each other, trying to create a high-intensity practice
environment where they can make each other better. They
might even do some light, joking trash-talk to get each other
riled up and motivated to put their best foot forward -- not
anything mean, of course, but just enough to get the other
person to react like "damn, let me show you what I got!"
 Advice on Upskilling – Working Draft | 57

But the thing is, it’s not even about winning the competition.
It’s about growing and improving, and the competition is just a
way to enter a psychological state where you’re motivated to
work hard and maximize your effort.

In this type of competition, it actually feels good to see the

other person take the lead and raise the bar. The whole idea is
that you want the other person to raise the bar on competition
and pass you up, so that you’re motivated to come right back
and do the same to them. It’s like you’re creating a video game:
each time one person passes another person up, a new level and
challenge is created. Everyone has fun playing the game and
wants to get to really high levels.

You could even call it teamwork: as a team, you try to maximize

your total absolute level by having everyone compete on their
individual relative levels.

Your Goal is NOT to Prove You're Smart, it's

to Make Problems Go Away

When you're working on a team, your primary goal is not to

prove you're smart. It's to make problems go away.

Yes, the more knowledgeable you are, the better you're

equipped to solve problems, but if your primary focus is
peacocking your intellect then you're going to create problems
instead of make them go away.
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You don't get points for creating an unnecessary problem on

which to demonstrate your smarts. You don't get points for
creating an overcomplicated solution to a simple problem. You
lose points for these things.

What you get points for is taking a problem and making it go

*poof,* completely solved and easy to maintain and nobody has
to think about it anymore.
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Chapter 7. The Mission

Selecting a Good Problem to Work On

What problem should you work on? At first, it doesn’t matter.

Just work on any toy problem that interests you so that you can
build technical skills and gain domain knowledge. It doesn’t
matter if you solve it or not, whether it’s been solved before, or
how impactful it is. But once you start getting into problems
that require many years of full-time work, selecting a good
problem becomes very important. This is the land of startups
and research labs, many of whose inhabitants regret that all the
time and effort they invested did not yield a commensurate
reward.

Personally, most of the toy problems I worked on were bad

problems. That’s okay because I learned a lot and gained a lot
of skills – which is the whole point of a toy problem – but it
made me painfully aware of two failure modes that can make a
problem bad.

Failure Mode 1: You don't have an implementable vision of what

the solution is. In particular, some of the resources you need
(e.g. data, algorithms, compute power) do not actually exist yet
and you don't have a good plan for obtaining them.
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This means the problem is too hard and you probably won’t be
able to solve it. In my experience, many complex systems
modeling problems lie here, e.g. creating useful predictive
models of the human brain or macroeconomy. For instance,
there was a time when I was interested in modeling the human
brain. I framed it as a regression problem on a time-series data
set containing the activities and connection weights of all the
individual neurons in brain. It took me a while to realize that
the data set I wanted did not exist, and creating it would
require multiple lifetimes and revolutionary breakthroughs in
wet-lab neuroscience (and I was not interested in wet-lab work).

It’s worth noting that sometimes, Failure Mode 1 is an

indication that you’re not actually interested in the thing that
you think you’re interested in. In my case, I thought I was
interested in neuroscience, but it turned out that I was
interested in a lot of stuff that just happened to show up in
neuroscience: multiscale modeling, connectionism, human
learning/intelligence, etc. The most obvious thing that
encapsulates all of those interests is building a model of the
biological brain, but it’s not the only thing. What I’m doing
now encapsulates all of those interests I listed and does not
require any wet-lab work. I did still have to get my hands dirty
with lots of teaching and content writing, but those were things
that I enjoyed.

Failure Mode 2: People don't care about the problem. They are
not willing to pay for a solution with whatever currency you're
interested in (money, citations, their time/attention, etc).

This means that you’re not going to experience any reward for
solving the problem. In my experience, theoretical modeling
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problems can fall victim to this when the problem framing

abstracts away details that make the problem intractable but
are important for application to real life.

It’s possible to argue that Failure Mode 2 doesn’t apply to you if

you’re ahead of your time. However, there are two issues with
that. First, you're probably not ahead of your time. Being ahead
of one's time is rare, unverifiable, and tempting to believe. Talk
about a recipe for flawed judgement! Second, even if it's true
that you are ahead of your time, if you are too ahead of your
time, then the reward will come too late in your life to feel
worth the sacrifice. You might not even live to experience it.

(That said, I have met some people who seemed entirely

satisfied by exploring their intellectual curiosity without the
prospect of receiving an external reward or making an external
impact in their lifetime, if at all. These people might be
legitimate exceptions to Failure Mode 2. But for the vast
majority of people, exploring intellectual curiosity is not
enough.)

How do you find a problem that avoids both failure modes? You
need to find (or create) an intersection between your own
interests/talents, the realm of what’s feasible, and the desires of
the external world. Unfortunately, it’s rarely obvious where the
intersection is. All the cards are stacked against its existence:
you can't choose what you're interested in or what you're
talented in, you can't choose what the rest of the world cares
about, and if you're interested/talented in some area to the
point that you want to solve problems in it, then your reasons
for being interested in it are probably not shared by the rest of
the world.
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So how do you find (or create) the intersection? What’s worked

for me is to live two parallel lives – one in which you do solve
problems that interest you, and another in which you solve
problems that interest the rest of the world. You continually try
to push the parallel lives closer and closer together, and
eventually, you figure out how to unify them.

The “Progress Equals Pressure” Formula

Most people know you have to build hardcore skills to do

hardcore things. But what a lot of people with hardcore skills
still don’t know is that you also have to shield yourself from
nerd-sniping (xkcd.com/356).

When you build hardcore skills, you increase the surface area of
things you can do – but many of these things are just
fascinating distractions. And if you allow these side-quests to
steal your attention, they dilute the power of your skills.

Making progress is all about putting pressure on a problem:

applying the force of your skills to a specific problem area
(pressure = force / area). Leveling up your skills will increase
your force, but if you want that to carry over to an increase in
pressure, you have to stay laser focused on the problem area
that you’re trying to cut into.
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Love What You Do

If you want to succeed wildly and consider it a life well lived,

you have to love what you do. There’s no way around it. If you
want wild success, and not just on a lottery ticket, then you
have to put in such a high volume of work that it is
life-consuming. And if your life is consumed by something you
don’t love, then it’s a life thrown away.

This is not to say you must love an activity to get better at it.
Effective practice will make you better at anything even if you
don’t love the thing. But if you don’t love it, you’ll never be able
to keep up with the same volume of effective practice as
someone who does have that love. You’ll never outwork them.

Love is perpetual hardcore effort. Not as a descriptor, but as a

definition. Love is being consistently hardcore. To say that a
parent loves their kid is to say that the parent is consistently
hardcore about raising their kid. That their kid is always on
their mind and they are always putting max effort into raising
their kid. You don’t love something if you’re not consistently
hardcore about it, and you won’t be consistently hardcore about
it if you don’t love it. It’s a biconditional, a definition.

Consistently hardcore people achieve extraordinary outcomes

through extraordinary actions; these actions go beyond the
ordinary and are often seen as crazy. Framed as love, this is
familiar: everyone knows that love makes people do crazy
things.
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Be a Builder, Not Just a Fighter

Once you acquire hardcore skills and new career opportunities

open up, try to avoid those that pit you against other
hardcore-skilled people playing zero-sum games.

What you want to do is create new value, not just fight over
existing value. And the way to do that is to build infrastructure
that solves people’s yet-unsolved problems. Be a builder, not
just a fighter.
 Advice on Upskilling – Working Draft | 65

Chapter 8. Motivation

Why Extrinsic Motivation Matters

It’s common to think that “learning for the sake of learning” is

better than “learning for the sake of achieving an extrinsic
goal,” but I’m not convinced that’s true. People whose
motivation is entirely intrinsic sometimes prioritize
“fascinating distractions” over other things that would be more
productive to their long-term happiness, in a sense “nerd
sniping” themselves.

I think optimal motivation requires a balance of both intrinsic

and extrinsic factors. Intrinsic motivation gets you working on
interesting things with a unique perspective. Extrinsic
motivation keeps you on the rails with your long-term goals
and keeps you from falling victim to fascinating distractions.

Furthermore, intrinsic vs extrinsic is a false dichotomy. It’s not

like you have a limited amount of motivation to split between
intrinsic and extrinsic factors. A percentage tradeoff is the
wrong way to look at it. It’s the other way around: there’s no
limit to how many motivational factors you can accumulate in
each category, and in turn, there’s no limit to how motivated
you can get.
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So regarding intrinsic versus extrinsic motivation, here are two

rules of thumb: 1) a balance across both sources is better than
the same amount concentrated on just one source, and 2) more
overall is better than less overall.

How to Become a Super-Producer

The #1 trick to super-productivity is interleaving a wide variety

of productive work that you enjoy. You get tired, bored, and
unproductive if you’re moving along one dimension for too
long.

The solution is to get yourself in a situation where your

production function has multidimensional input and all those
inputs have large partial derivatives on the same order of
magnitude. You follow the gradient in that space by cycling
between these component activities. The activities are
orthogonal, so whenever you start getting tired, bored, and
unproductive from moving along one dimension for too long,
you just switch to a different activity, moving along a different
dimension.

That said, it’s important to remember that “interleaving a

variety of productive work” is different from running away
from your problems. If you’ve hit a rut on some activity, and
you’re switching tasks just to avoid dealing with that problem,
and it’s been this way for a handful of cycles, then you’re past
the limit of “taking a break to freshen up” and what you really
need to do is bunker down and bust through the plateau.
 Advice on Upskilling – Working Draft | 67

How to Mitigate Intellectual Body

Dysmorphia

Compare the capabilities of your present self to your past self.

That should make the growth obvious. There should be things
you used to be really confused about (or maybe even confidently
wrong about) that are way more clear now. Or things that used
to take a lot of effort to accomplish, that would be way easier
now.

Also – maybe this is less wholesome – but once you reach a

high enough level of skill you can periodically compare yourself
to other people who are clearly less skilled. Not saying things
to make them feel bad, or even thinking poorly of them, just
noticing evidence that your percentile has changed on the bell
curve.

But of course you can’t spend too long in this state. You dip in
to get your confidence up again, and then you snap out and get
back to lifting those metaphorical weights that are heavy
enough to make you feel weak again.
68 | Advice on Upskilling – Working Draft
 Advice on Upskilling – Working Draft | 69

Chapter 9. Learning

The Greatest Educational Life Hack:

Learning Ahead of Time

Why learn ahead of time? Because it guards you against

numerous academic risks, opens all kinds of doors to career
opportunities, and allows you to enter those doors earlier in life
(which in turn allows you to accomplish more over the course
of your career).

You know how, when you take a language class, there’s often a
couple kids who speak the language at home and think the
class is super easy? You can do that with any other subject.
When you pre-learn the material in a course before taking it at
school or college, you’re basically guaranteed an A in the class.

You guard yourself against all sorts of risks such as the course
moving too quickly, brushing over concepts, explaining things
poorly, assuming knowledge of important but frequently
missing prerequisite material, not offering enough practice
opportunities… There are a hundred different ways to teach a
class poorly, and most classes suffer in at least a handful of
those aspects. This is especially helpful at university, when
lectures are often unsuitable for a first introduction to a topic.
But if you pre-learn the material, you’re not depending on the
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teacher to teach it to you, which means you’re immune to even

the worst teaching.

Of course, the natural objection is “won’t you be bored in

class?” – but if you do super well in advanced classes, especially
at university, then that opens all kinds of doors to
recommendations for internships, research projects with
professors, etc. It doesn’t matter whether you’re doing super
well because you’re learning in real-time or because you
pre-learned the material.

When you blow a course out of the water while also interacting
with the professor, that sets you up for a great recommendation
letter – which is vital not just for high schoolers applying to
college, but also for college students applying to summer
research programs and graduate schools. Plus, it can open the
door to working on a research project with the professor, or
having them connect you to jobs, internships, and other
opportunities with people in their network.

Basically, you can use pre-learning to kick off a virtuous cycle.

Even if you aren’t a genius, you appear to be one in everyone
else’s eyes, and consequently you get a ticket to those
opportunities reserved for top students. Students who receive
and capitalize on these opportunities can launch themselves
into some of the most interesting, meaningful, and lucrative
careers that are notoriously difficult to break into.

And why stop at pre-learning one year ahead? It’s worth it to

keep going, keep accelerating. The road always stretches
farther than what you can see in front of you, and you maximize
your reward by traveling as far as you can.
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Let’s consider math, for example. Many people think calculus

is the “end of the road” for math, and that it doesn’t matter if
you get there many years ahead of schedule. But that’s far from
the truth! There are even more university-level math courses
above calculus than there are high school courses below
calculus.

After a single-variable calculus course (like AP Calculus BC),

most serious students who study quantitative majors like math,
physics, engineering, and economics have to take core
“engineering math” courses including Linear Algebra,
Multivariable Calculus, Differential Equations, and Probability
& Statistics (the advanced calculus-based version, not the
simpler algebra-based version like AP Statistics). Beyond those
core “engineering math” courses, different majors include
plenty of specialized courses that branch off in various ways.

There are so many courses that a student could not fit them all
into a standard 4-year undergraduate course load even if they
overloaded their schedule every year – however, the more of
these courses a student is able to take, the more academic
opportunities and career doors are open to them in the future.
(And while it’s true that students don’t need to know much
beyond algebra to get a basic job a field like computer science,
medicine, etc. – the people in such fields who do also know
advanced math are extra valuable and in demand because they
can work on projects that combine domain expertise and math.)

When a student learns a lot of advanced math ahead of time,

they unlock the opportunity to dig into a wide variety of
specialized fields that are usually reserved for graduates with
72 | Advice on Upskilling – Working Draft

strong mathematical foundations. This fast-tracks them

towards discovering their passions, developing valuable skills
in those domains, and making professional contributions early
in their career, which ultimately leads to higher levels of career
accomplishment.

I’m not exaggerating here – this is actually backed up by

research. On average, the faster you accelerate your learning,
the sooner you get your career started, and the more you
accomplish over the course of your career. For instance, in a
40-year longitudinal study of thousands of mathematically
precocious students, researchers Park, Lubinski, & Benbow
(2013) concluded the following:

"The relationship between age at career onset and adult productivity,

particularly in science, technology, engineering, and mathematics
(STEM) fields, has been the focus of several researchers throughout
the last century (Dennis, 1956; Lehman, 1946, 1953; Simonton, 1988,
1997; Zuckerman, 1977), and a consistent finding is that earlier
career onset is related to greater productivity and accomplishments
over the course of a career. All other things being equal, an earlier
career start from [academic] acceleration will allow an individual to
devote more time in early adulthood to creative production, and this
will result in an increased level of accomplishment over the course of
one's career.
...
[In this study] Mathematically precocious students who grade skipped
were more likely to pursue advanced degrees and secure STEM
accomplishments, reached these outcomes earlier, and accrued more
citations and highly cited publications in STEM fields than their
matched and retained intellectual peers."
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When Does the Learning Happen?

Learning is the incremental gain in your ability to perform a

tangible, reproducible skill. If you’re not getting those gains,
you’re not learning.

Imagine signing up for tennis lessons with a personal coach.

When does the learning happen? It’s not when you pay the
coach the money. It’s not when you watch the coach
demonstrate a move. It’s when you actually start doing things
that you weren’t able to do before. It’s when you attempt a
move, the coach corrects your form, and you attempt the move
again with better results.

It’s the same anywhere else. The keys to effective training in

athletics, music, etc., are the same as the keys to effective
training in any other skill-based domain (e.g., mathematics).
Simply consuming information doesn’t cut it. You have to
actively practice the skills that you’re hoping to acquire.

There is No Such Thing as Low-Effort

Learning

Talent development takes work – not just a little work, but a lot
of work. There is absolutely no confusion about this in the
talent development community. Can you imagine asking an
athletic coach to help you become a star player using training
methods that don’t tire you out and make you sweat? No matter
what skill is being trained, improving performance is always an
effortful process.
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A common theme in the science of learning is that effective

learning feels like a workout with a personal trainer. It should
center around deliberate practice, a type of active learning in
which individualized training activities are specially chosen to
improve specific aspects of performance through repetition
and successive refinement. These practice activities are done
entirely for the purpose of pushing one’s limits and improving
performance; consequently, they tend to be more effortful and
less enjoyable.

Unfortunately, another common theme in the science of

learning is that the perception of learning is often at odds with
actual measurable learning. When using effective learning
strategies, students perform better on assessments but may feel
they’ve learned less. Why? Because effective strategies increase
cognitive activation, enhancing learning despite students
feeling it’s harder. It’s like weightlifting – the strongest people
lift weights heavy enough to make them feel weak.

Many types of training methods are ineffective, but require

little effort, and can therefore seem attractive to even the most
well-intentioned, hardworking students because they create an
illusion of comprehension. Examples include looking at notes,
rereading course materials, and highlighting.

It is useful to familiarize oneself with instructional material

before engaging in effortful practice, and it is also useful to
revisit that material if one runs into issues while attempting to
carry out the effortful practice – but it is not until effortful
practice that true learning actually occurs. Familiarizing
oneself with instructional material is similar to warming up
 Advice on Upskilling – Working Draft | 75

before a workout: the warmup does not actually lead to

improvements in strength or endurance, but it does help
maximize performance and avoid injury during the workout.

The Greatest Breakthrough in the Science of

Learning Over the Last Century

The greatest breakthrough in the science of learning over the

last century was characterizing the mechanics of learning in
the brain. Learning is all about the interplay between working
memory (WM) and long-term memory (LTM). If you understand
that, then you can actually derive – from first principles – the
methods of effective learning.

The goal of learning is to increase the quantity, depth,

retrievability, and generalizability of concepts and skills in your
long-term memory (LTM). At a physical level, that amounts to
creating strategic connections between neurons so that the
brain can more easily, quickly, accurately, and reliably activate
more intricate patterns of neurons. This process is known as
consolidation.

Now, here’s the catch: before information can be consolidated

into LTM, it has to pass through working memory (WM), which
has severely limited capacity. The brain’s working memory
capacity (WMC) represents the amount of effort that it can
devote to activating neural patterns and persistently
maintaining their simultaneous activation, a process known as
rehearsal.
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Most people can only hold about 4 chunks of coherently

grouped items simultaneously in WM, and only for about 20
seconds. And that assumes they aren’t needing to perform any
mental manipulation of those items – if they do, then fewer
items can be held due to competition for limited processing
resources.

Limited capacity makes WMC a bottleneck in the transfer of

information into LTM. When the cognitive load of a learning
task exceeds your WMC, you experience cognitive overload and
are not able to complete the task. Even if you do not experience
full overload, a heavy load will decrease your performance and
slow down your learning in a way that is NOT a desirable
difficulty.

However, once you learn a task to a sufficient level of

performance, the impact of WMC on task performance is
diminished because the information processing that’s required
to perform the task has been transferred into long-term
memory, where it can be recalled by WM without increasing
the actual load placed on WM.

So, for each concept or skill you want to learn:​

1.​ it needs to be introduced after the prerequisites have been

learned (so that the prerequisite knowledge can be pulled
from long-term memory without taxing WM),​

2.​ it needs to be broken down into bite-sized pieces small

enough that no piece overloads your WM, and​
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3.​ you need to get enough practice to achieve mastery on each

piece (and that amount of practice may vary depending on
the particular learning task).

But also, even if you do all the above perfectly, you still have to
deal with forgetting. The representations in LTM gradually,
over time, decay and become harder to retrieve if they are not
used, resulting in forgetting.

The solution to forgetting is review – and not just passively

re-ingesting information, but actively retrieving it, unassisted,
from LTM. Each time you successfully actively retrieve fuzzy
information from LTM, you physically refresh and deepen the
corresponding neural representation in your brain. But that
doesn’t happen if you just passively re-ingest the information
through your senses instead of actively retrieving it from LTM.

“Following Along” Versus Learning

People often think “following along” is the same as learning –

like, if you can follow along with a video, book, lecture,
whatever, without feeling confused, then you’re learning. I
know it “feels” like learning when you’re following along, but
that feeling is completely artificial.

Comfortable fluency in consuming information is not a proxy

for actual learning. Learning is a positive change in long-term
memory, and you haven’t learned unless you’re able to
consistently reproduce the information you consumed and use
it to solve problems. This doesn’t happen when you just “follow
along,” even if you understand perfectly. That comfortable
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fluency you feel while following along is arising from the fact
that the surrounding context is already on your mind – you’re
not made to pull it from long-term memory.

When you feel like you’re absorbing information while

passively following along, what you perceive is information
sitting in your working memory, not your long-term memory. If
you want to test whether information is in your long-term
memory (i.e., whether you've actually retained it), you have to
actively attempt to retrieve it when it's not already at the front
of your mind. You have to put yourself in the position where
it's not already in your working memory, and the only way to
pull it out of your brain is from long-term memory.

If you don’t practice retrieving information from memory, it

dissipates quickly and almost entirely. Have you ever had the
experience of being unable to remember something despite
repeated exposures, because you keep automatically looking it
up from a reference instead of trying to retrieve it from
memory? That’s happened to me an embarrassing number of
times with addresses, phone numbers, directions, etc. And any
books you read, movies you watch – the only ones you
remember in proper detail are the ones you periodically think
about and replay in your head. If you just consume and don’t
reproduce then you forget almost entirely. I can’t tell you how
many times I’ve watched a movie and didn’t even realize I’d
seen it before until I got 20 minutes in and something felt
familiar. And even then I could barely remember anything
about the rest of the movie, just that it felt a bit familiar.

Retrieval is the act of pulling information from long-term

memory into working memory. Practicing retrieval under
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challenging but achievable conditions (e.g., when your memory

has gotten fuzzy or there is less priming) is what increases your
ability to remember and use information. Each time you
successfully recall a fuzzy memory, it stays intact longer before
getting fuzzy again. Each time you successfully recall a memory
with less priming, its recall becomes less dependent on priming
in the future.

But if you don’t practice retrieval, then this doesn’t happen.

The information quickly dissipates. It stays with you only
briefly – just long enough to trick you into thinking it’ll stick
with you, when it’s really on the way out the door. But, of
course, you don’t notice that it’s gone if you’re not actually
testing whether it’s there.

Consuming information without practicing reproducing it can

produce an artificial feeling of fluency while the information is
held and manipulated in working memory, but since retrieval
practice is not occurring to extend the information’s retention,
the information dissipates quickly. The fact that it’s in working
memory can trick you into thinking it’s going to stay there, but
it doesn’t.

Once it’s gone, the only way you can bring it back without
reloading it from an external reference is if you’re able to
retrieve the information from long-term memory. But if you
don’t practice retrieval, you won’t be able to successfully
retrieve. When all you do is consume information, you put
yourself in a situation where the only way to load it back into
your working memory is to re-consume it. This is why learning
really amounts to increasing your ability to recall information
from long-term memory unassisted, an action that can be
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trained by repeatedly performing said action in gradually more

challenging contexts, just like strength training.

Additionally, learners typically do not process all the key

information as they consume, but they are unaware of this until
they attempt to answer a question or solve a problem that
requires them to retrieve some key information from memory.
At that point, they realize that they never fully processed that
piece of information to begin with, and they have to go back to
find and properly process it. The same applies to
generalization: learners typically do not fully generalize what
they’ve consumed, but they are unaware until they attempt to
answer questions or solve problems that require them to
generalize their understanding.

The way to avoid this problem and maximize your learning is to

switch over to active problem-solving immediately after
consuming a minimum effective dose of information. I know
that might feel a bit jarring, like it’s slowing you down, but it
isn’t actually slowing down your learning – it’s only exposing
the fact that your perception of learning does not accurately
reflect actual learning. Really, it’s speeding up your actual
learning, and the only thing it’s slowing down is your
perception of learning.

Now, you might say “but I had learned so much, and I had it
down pat, and then I forgot it all when I focused my effort on
solving a problem.” But the thing is, if you can’t retrieve that
information from memory at the snap of a finger, after thinking
about other stuff or zooming in to focus on a specific problem,
it means you didn’t really have it down pat.
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The Vicious Cycle of Forgetting

Forgetting is frustrating. After putting forth the effort to learn

something, who wants to waste time re-learning it later? To
mitigate the effects of forgetting, it might feel helpful to solve
problems alongside reference material.

But there’s an issue: when you continually look back at a

reference, the information doesn’t stay in your brain. You hold
the information in short-term memory, but only temporarily –
it dissipates after your focus redirects elsewhere. The reference
material becomes a crutch, and you’re lost without it. You
might think you need to spend more time reviewing the
reference, but really you just need to review properly, pulling
information from memory.

Even people who are serious about their learning sometimes

fall into this vicious cycle of forgetting. They might take great
notes and then refer back to those notes all the time instead of
trying to pull the information from memory.

The thing is, if you try to keep the information close by taking
great notes that you can reference all the time, that just
PREVENTS you from truly retaining it. That might seem
counterintuitive, but it’s actually pretty obvious. What’s the
thing that transfers information to long-term memory?
Retrieving from memory. When you take great notes and
constantly refer back to them, you know what you’re NOT
doing? Retrieving from memory.

Retrieval is not just any loading of information into your brain.

Retrieval is the specific action of “pulling” information from
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one part of your brain (long-term memory) to another part of

your brain (working memory). It’s like your brain is lifting a
weight off the ground of long-term memory and raising it up
into working memory. The fuzzier the memory, the heavier the
weight – but just like weightlifting, as you practice lifting heavy
weights, you get stronger, i.e., your brain becomes more easily
able to activate the pattern of neurons that represent the
information stored in long-term memory.

If you load information into working memory by looking at

reference material instead of pulling from long-term memory,
then you’re not strengthening your retention. It’s like you’re
going to the gym to lift weights, but you’re just going through
the motions and letting your spotter lift the weight for you. No
strength is being developed. You end up throwing yourself into
a vicious cycle of forgetting:

●​ You keep looking back at a reference because you can't

remember things.
●​ You can't remember things because you're not transferring
them to long-term memory.
●​ You're not transferring them to memory because you're not
practicing retrieving them from memory.
●​ You're not retrieving them from memory because you're
always looking back at the damn reference!

As you spiral into this vicious cycle of forgetting, your whole

learning process completely falls apart. You learn slower, forget
faster, and miss out on making connections that would deepen
your understanding.
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The only way to break this vicious cycle of forgetting is to

engage in retrieval practice. Initially, that may seem like a
paradox: “how can I engage in retrieval practice if I’m unable to
retrieve?” But it’s not a paradox at all. Back to weightlifting –
you just need to treat the reference material like a spotter. You
try your hardest to lift the weight, and if you can’t, the spotter
intervenes as a last resort, giving you just enough assistance to
get you over the edge of lifting the weight. The spotter should
be doing as little as possible while ensuring that you manage to
eek out a successful rep.

In the same way, whenever you're about to look up information

that you've seen before, that you would like to stick in your
brain – always, always, always try your best to recall it from
memory. DO NOT default to looking it up. If you cannot
manage to retrieve it despite trying your best, then it’s okay to
peek back at your reference material, but only as a last resort.

Peek once – just a little bit, just the tiniest bit of priming, just
that specific piece of info that you were trying to remember,
nothing else – and then close the reference, re-pull the
information from memory, and try to recall the rest and
proceed forward as far as possible without peeking back at the
reference again. Never, ever transcribe from the reference. Your
brain is lifting a weight and the reference material is your
spotter – it’s there as a last resort to help you get the weight up,
only when you absolutely can’t get it up yourself, and the
amount of help should be kept to the bare minimum.

The goal is to wean yourself off of reference material, using it

as sparsely as possible, until you don’t need it at all. This may
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be very challenging if you’ve been relying on reference material

as a crutch, but it’s the only way out of the vicious cycle.

And you know what helps you wean yourself off of a crutch?
Not having easy access to it. As long as you have a reasonable
way to look up a piece of information if you forget it, then it’s
not worth optimizing for convenience. You WANT it to feel
annoying to look stuff up, so that you're incentivized not to
have to do that. And if you're engaging in proper retrieval
practice, you won't have to spend much time looking stuff up
anyway.

The Vicious Cycle of Context Overload

One of the least efficient ways to learn is to attack the most

challenging “authentic” or real-world problem context right
from the get-go. It creates a vicious cycle where you

1.​ struggle with the problem due to the additional complexity,

2.​ take so long to solve it that there’s time pressure to move
on to new material,
3.​ struggle even more with the new material because you
didn’t get enough reps in to master the previous skill,
4.​ and then the cycle repeats again starting from (1).

It’s a lot more efficient to strip skills down to the simplest

possible context, get some reps in, and gradually increase the
complexity of the context. When you get that scaffolding right,
you can complete each rep reasonably quickly because the
challenge is matched to your skill level, and you end up
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climbing the skill tree even faster while building a solid

foundation.

Prereq Yo’ Self Before You Wreck Yo’ Self

Being out of your depth in skill training is a huge problem

because your learning progress grinds to a halt. It’s not like
you’re on a train that left late from the station. It’s like you’re
on a train that’s not even moving. The train might even start
moving backwards: if you’re so far out of your depth that you’re
just flailing around on new skills, then you’re likely not
absorbing much implicit review on the component skills you’ve
previously learned, and as a result you’re forgetting them.

The only way to get the train moving forwards again is to drop
down and work at a level that’s appropriate for you. You need
to get yourself in a situation where you’re successfully
accomplishing new challenges. If you don’t, the situation
compounds into a vicious cycle, getting worse and worse. You
continually come into new skills less and less prepared, getting
more and more out of your depth.

When you skip prerequisites or otherwise don’t master them,

you don’t have those skills available for automatic execution, so
when you’re attempting to execute a new skill that depends on
them, you exhaust all your focus and effort attempting to carry
out the prerequisites. You might have the bandwidth to focus
on a single prerequisite if you put all your focus and effort
behind it, but not to execute multiple prerequisites in parallel,
much less monitor and control the entire complex operation at
a high level.
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The only solution is to hammer in your prerequisite skills until

they’re rock-solid and easy to execute. That way, no individual
prerequisite takes up much focus or effort, and you can execute
multiple prerequisites in parallel while seeing the forest for the
trees and strategizing at a high level.

The Efficient Learning Loop

All the information you consume while learning, every problem

you work out, it comes with the cost of using up more of your
time. It has to be worth it.

If you’re looking to maximize your learning efficiency, then

what want is

●​ streamlined instruction ("no BS, just give it to me straight"

explanations),
●​ most of the time focused on active problem-solving, and
●​ continually switching back and forth between instruction
and problem-solving quickly enough that your attention
span doesn’t run out.

It’s a continual cycle of minimum effective doses:

●​ minimum effective dose of streamlined "no BS, just give it

to me straight" instruction,
●​ followed by minimum effective dose of problem-solving,
●​ then back to minimum effective dose of instruction to
prepare you for slightly more challenging problems,
●​ followed by minimum effective dose on said problems,
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and so on.

Schooling Versus Talent Development

The fundamental principles of effective training are similar

across domains. But you only see this if you're actually
optimizing for performance. That's what's done in the field of
talent development: an individual’s performance is to be
maximized, so the methods used during practice are those that
most efficiently convert effort into performance improvements.
But elsewhere in education, the norm seems to be optimizing
for fun and entertainment while, as a secondary concern,
meeting some low bar for shallowly learning some surface-level
basic skills.

Schooling and talent development are completely different

things. In schooling, students are grouped primarily by age,
rather than ability, and each group progresses through the
curriculum in lockstep. Each member of the group engages in
the same tasks at the same time, and it is expected that
different students will learn skills to different levels.

In talent development, students progress through skills at

different rates, but learn skills to the same threshold of
performance. Their progress is measured not by their level of
learning in courses that they have taken, but rather by how
advanced the skills are that they can execute to a sufficient
threshold of performance. This is accomplished through
completely individualized instruction. Learning tasks are
chosen based on the specific needs of individual students, each
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student must learn each skill to a sufficient level of mastery

before moving on to more advanced skills.

This contrast between schooling and talent development is not

new. Researchers have known about it for many decades. For
instance:

●​ “Schools do not seem to have a great tolerance for students

who are out of phase with other students in their learning
process.” –Benjamin Bloom, 1985​

●​ “In general, school learning emphasizes group learning and

the subject or skills to be learned. Talent development
typically emphasizes the individual and his or her progress
in a particular activity.” –Bloom & Sosniak, 1981

At the heart of it all, here’s the core difference: Outside talent

development, lots of people in education disagree with the
premise of maximizing learning. Whereas in talent
development, an individual’s performance is to be maximized,
so the methods used during practice are those that most
efficiently convert effort into performance improvements.

Here’s a concrete example. On one hand, “testing” and

“repetition” have become dirty words in education. However,
practice testing and distributed practice (also known as spaced
repetition) are widely understood by researchers to be two of
the most effective practice techniques. Moreover, deliberate
practice – which has been shown to be one of the most
prominent underlying factors responsible for individual
differences in performance, even among highly talented elite
performers – is centered around using repetitious training
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activities to refine whatever skills move the needle most on a

student’s overall performance.

So what gives? Why are there debates about scientifically

proven learning techniques like testing and repetition? Because
lots of people in education disagree with the premise of
maximizing learning. The debates aren’t about whether testing
and repetition are effective learning techniques – the debates
are about whether education should seek to maximize students’
learning.

Outside of talent development, the typical approach to

education involves maximizing other things like fun and
entertainment while, as a secondary concern, meeting some
low bar for shallowly learning some surface-level basic skills.
I’ll admit that de-prioritizing talent development ends up
working out okay when students aren’t expected to achieve a
high level of success. For instance, if every student in gym class
were expected to be able to do a backflip by the end of the year,
things would have to change – but the expectations are so low
that meeting them does not require talent development.

But serious skill development is different. Take math class, for

example. Students are typically expected to achieve a relatively
high level of success in math: many years of courses increasing
in difficulty, culminating in at least algebra, typically
pre-calculus, often calculus, and sometimes even higher than
that. As a result, in math, de-prioritizing talent development
leads to major issues. When students do the mathematical
equivalent of playing kickball during class, and then are
expected to do the mathematical equivalent of a backflip at the
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end of the year, it’s easy to see how struggle and general
negative feelings can arise.

A Sanity Check for Effective Study

Techniques

Every time you study, imagine the Grim Reaper is going to

show up at the end of your session to quiz you on what you
covered, and if there’s any question you can’t answer correctly,
you die. Whatever study techniques you’d use in that situation,
you better be using them already.

(I should emphasize that getting stuff wrong occasionally is

totally okay and expected. The thought experiment here is
more about the actions than the results: truly optimal study
strategies would be conserved even in the theoretical
highest-stakes scenario. When a high-accountability situation
induces change in learning techniques, it exposes that the
emperor was originally wearing no clothes.)