A Skill Called

Luck
How to bring more and better
opportunities into your life.

Jakob Greenfeld
Contents

Introduction 1
Bird’s Eye Overview . . . . . . . . . . 7

Hustle 10
Shipping . . . . . . . . . . . . . . . . 11
Building an Audience . . . . . . . . . 15
Networking . . . . . . . . . . . . . . 18

Setup 22
Visibility . . . . . . . . . . . . . . . . 24
Openness . . . . . . . . . . . . . . . 29
Likeability . . . . . . . . . . . . . . . 31

Creativity 35
Input . . . . . . . . . . . . . . . . . 36
Digestion . . . . . . . . . . . . . . . 39
Processing . . . . . . . . . . . . . . . 43
Skill . . . . . . . . . . . . . . . . . . 44

ii
Capacity 51
Mindset . . . . . . . . . . . . . . . . 53
Skills and Money . . . . . . . . . . . 57
Freedom . . . . . . . . . . . . . . . . 60

The Next Step: Where to Go From Here 63

Chapter 1
INTRODUCTION

Imagine two equally talented 21 year-olds, John

and Sam, who have decided to become writers.
Both of their parents work blue collar jobs and nei-
ther of them has any connections in the publish-
ing industry.

Their situation and goals are exactly the same. But

their strategies couldn’t be any more different.

John decides to focus on reading as many books

as possible about the craft of writing. At the same
time, he wants to avoid any other kind of books or
articles as much as possible. This will make sure he
doesn’t just copy other people’s stuff but will actu-
ally come up with truly original thoughts. In fact,
he already started writing his first book and esti-

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 Jakob Greenfeld

mates that he’ll finish it in around two years. Since

he can read and write anywhere, it makes sense for
him to keep living at parents house. Once his book
is perfect, he’ll start sending it to book publishers.
Surely one of them will recognize his genius.

Sam’s plan on the hand, is to start a newsletter and

to become active on Twitter. He commits to pub-
lishing two newsletter issues every week and two
tweets every day no matter how bad they might be
in the beginning. To make sure he never runs out
of ideas, he dedicates one hour every day to read-
ing and notetaking. There’s no strict curriculum.
He will read and write down whatever sparks his
interest. He plans to attract readers by republish-
ing his newsletter issues in as many places as possi-
ble. He also wants to focus on building connec-
tions with fellow writers and people he admires.
So he commits to sending at least one cold email
and replying to one newsletter he’s subscribed to
every day. For the same reason, he decides to move
to Austin. He heard on some podcast that this is
the place to be in right now.

Now who would you say has better chances of be-

coming a successful writer?

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 A Skill Called Luck

I’d definitely bet on Sam.

The chances that luck finds John are basically zero

until he starts sending out his manuscript. And
even then, they remain slim as publishers get thou-
sands of manuscripts send their way every year and
John’s book will most likely be pretty boring.

In contrast, Sam does a lot to actively increase his

luck surface area. He puts himself out there from
day one, works hard to drive eyeballs to his words,
and builds relationships. Once he built a solid
email list and his name starts to spread, publishers
will most likely start reaching out to him.

And by moving to Austin, he dramatically in-

creases the odds for chance encounters with guys
like David Perrell or Tim Ferriss who potentially
could help his career tremendously. He also dra-
matically increases his odds of having good ideas
through his daily, curiosity-driven reading and
notetaking session.

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 Jakob Greenfeld

Now you’re most likely not 21 and don’t aspire to

become a writer. But you always have a choice to
act more like John or like Sam, no matter your age
and goals.

You can wait passively and hope that the world will
eventually recognize your genius. Or you can de-
velop and execute a plan to actively increase your
luck surface.

To be clear, luck is still randomly occurring. John

might observe something in the local supermarket
that leads to a Eureka moment that leads to a fan-

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 A Skill Called Luck

tastic book that will get picked up by a publisher

and become a bestseller. And Sam might not find
any success with his newsletter and networking ef-
forts.

There are always things outside of your control

and no guarantees.

But it’s always possible to stack the odds in your

favor. You can actively create optimal conditions
for lucky things to happen to you. And in the fol-
lowing chapters, I’m going to show you how.

But first, let me emphasize that this is not just

about newsletter or building some kind of online
presence.

For example, let’s say you’ve decided to get into

shape and do more sports. What are your options?

You could for example, start going to the gym or

build a home gym.

While other factors definitely also play a role, it’s

important to realize that these options have very
different serendipity potential.

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 Jakob Greenfeld

• The odds of having a chance encounter

with an interesting stranger who might end
up helping your career at your home gym is
zero.
• At a proper gym the odds are definitely bet-
ter and you can increase them further by
joining the most expensive gym in town
and leaving your headphones at home. For
example, Sahil Bloom ran into Tim Cook,
the CEO of Apple, at the local gym. They
were both working out at 5am when the
gym was mostly empty and started talking.
Sahil followed up via email and Tim Cook
became his mentor.

In a similar way you can asses different alterna-

tives like joining group fitness classes, start run-
ning alone, and joining a sports club (where the
choice of sports plays a major role for its serendip-
ity potential).

Okay so now let’s get a bit more systematic. What

are the exact levers you can pull to increase your
luck surface area?

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 A Skill Called Luck

Bird’s Eye Overview

There are three four areas you can focus on, if you
want to bring more luck into your life that can be
divided along two axis:

The most obvious thing you can do is hustle.

The more you put out there, the more emails
your send, the more events you attend, the luck-
ier you’ll get.

But you can also improve your setup by, for exam-
ple, moving to a location with better odds of meet-
ing people that can help you achieve your goals,
dressing well, not wearing headphones thorough

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 Jakob Greenfeld

the day, having a great personal website , and pick-

ing the right kind of third place to hang out at.

Hustle means that you go out there and hunt for

opportunities, while your setup influences how
many opportunities find you. That’s the distinc-
tion between active and passive in the diagram
above.

There are really just two core insights when it

comes to hustle and your setup.

The first one is this: people route opportunities

towards 1.) people they like and 2.) whoever is top
of mind right now. Once you’ve internalized this,
coming up with strategies to increase your luck
surface area is straightforward. You just have to be-
come more visible and more likeable. That’s really
it. We’ll talk concrete strategies in a moment.

The second core insight is that quantity is king

when it comes to luck. The more you do, the luck-
ier you get. Everything you do (and actually put
out there) increases your odds of winning big. Just
think about it: who’s more likely to win the lot-
tery? The guy with just one ticket or the guy with
10,000 tickets?

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 A Skill Called Luck

A second distinction in the diagram above is be-

tween what happens in the world out there and
what’s going on in your mind.
You need great ideas to level up in any area of your
life and having them requires luck. But you can
dramatically increase the number of Eureka mo-
ments you have using proactive strategies like a
healthy information diet, a notetaking system that
facilitates serendipity, and training your idea mus-
cle.
And this leaves us with the final and most impor-
tant quadrant in the diagram: Capacity.
Capacity is your ability to seize opportunities that
present themselves to you. It includes factors
like your skills, mindset, money in the bank, and
how much freedom you have over your time and
choices.
Let’s talk about these four pillars your luck surface
area consists of one by one.

9
Chapter 2
HUSTLE

“I have never heard of anyone stumbling on some-

thing sitting down.” - Charles Kettering

Hustle is about proactively bringing more luck

into your life. And the most important thing to
keep in mind is that no matter what your goals

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 A Skill Called Luck

are, it’s always about people. Doing a ton of work

without ever telling anyone about it won’t open
any new doors for you.

Shipping

To get lucky, you have to take a ton of swings.

Real-life games have far too many degrees of free-

dom to allow for high-accuracy predictions. In
other words, no one knows for sure what’s going
to work. Even huge companies like Google who
have access to almost unlimited funds and talent,
launched far more failures that successes.

But the good news is that unlike in sports, real-

life games like business have an extremely long-
tailed distribution of returns. In baseball, no mat-
ter how well you connect with the ball, the most
runs you can get is four. In real-life, however, ev-
ery once in a while, you can score 1,000 runs. Win-
ners can pay for a large number of experiments.

So to get lucky, you have to keep swinging and

trust the process.

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 Jakob Greenfeld

But here’s something most people overlook.

You have to carry full swings, not stop half-way

through. Otherwise, you’ll never get lucky and hit
a homerun.

Most people lose their momentum near the end of

the swing. It’s when the resistance sets in.

“What will people say about this thing I created?”

“It’s just not good enough. But surely my next try will
be!”

Rinse and repeat ad infinitum. And so they never

actually ship that project, never publish that essay.

The chances that the software you coded will be-

come the next unicorn is zero as long as it only
lives on your harddrive. An unpublished novel
can never become a bestseller.

Every unfinished draft and project is a lottery

ticket you put into the bin before ever checking
the numbers on it.

Another overlooked feature of real-life games is

that you have a lot of control over the number of
lottery tickets you have in your pocket. It’s not as

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 A Skill Called Luck

if everyone gets handed a fixed number tickets per

year. Instead, you can create them out of thin air.

So how can you increase the number of lottery

tickets in your pocket?

One strategy that makes a lot of sense is to ship

many small projects instead of a huge one. This
allows you to take ten or even hundred swings
in the same time you’d otherwise take just one.
Your one big bet might have somewhat better suc-
cess chances than each individual small bet, but all
small bets taken together are far more likely to be
successful.

It’s why the idea of building minimum-viable

products has become so popular in startup cir-
cles. But you can do the same no matter what area
you’re operating in.

For example, instead of writing a book you can

write an essay. The odds that your book will be-
come a bestseller are slim. It’s one huge bet and if
it fails, you’re pretty much screwed.

You can also put the same time and energy into
writing a series of essays that you put out there of-

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 Jakob Greenfeld

ten and early. For each of them, there is a chance

that it will resonate with people. If this happens,
you can double down and produce more work
along similar lines. This way each subsequent bet
will have better and better odds.

You could go even further and write tweets instead

of essays which might be the purest form to test if
individual ideas resonate with people.

These are the main ingredients when it comes

to getting lucky through hustle: take a ton of
swings, keep swinging, do full swings instead of
half swings.

Now that we’ve established the importance of de-

liverable (aka shipping stuff), let’s talk about a spe-
cific kind of deliverable: content.

Building an Audience

What’s awesome about content is that anyone can

create it quite easily nowadays. There are tons of
great tools and guides, not matter which medium
you choose.

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 A Skill Called Luck

Tweets, YouTube videos, blog posts, Insagram

posts are all incredibly cheap lottery tickets. But at
the same time, they can led to spectacular returns.

Entire careers have been built on a few pieces of

content that went viral.

Most people think it’s cringy to start a personal

blog, newsletter, podcast, or having an active Twit-
ter, Youtube, and Instagram account.

But what these people don’t realize is that putting

yourself out there online is not about becoming
the next Logan Paul. Instead, it’s about engineer-
ing serendipity.

Each piece of content you publish is a bat signal.

Once you stop hiding and put your brain out into
the world, amazing things start to happen. All of
the sudden, the right kind of people and opportu-
nities magically start appearing at your doorstep.

When you have an engaged audience, the odds of

each bet you put out there significantly improve
since the chances that the right kind of people take
note of what you created will be a lot higher.

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 Jakob Greenfeld

If you have an audience, you can often mani-

fest opportunities simply by making your wishes
known. Every time I write about the problems
I’m struggling with in my personal newsletter, my
inbox fills with amazing people offering help and
advice.

You’ll also get feedback a lot faster and strangers

will start trusting you more quickly.

After all, a better term for audience building

would be “earning trust at scale.”

And you definitely don’t need to do crazy stunts,

post cringeworthy content or turn your personal
brand into a full-time job to see these kinds of ef-
fects.

The specifics of how to build an audience effec-

tively is a topic that requires at least another book
in itself.

But simply publishing something on a regular ba-

sis will already put you far ahead. Even if you your
post doesn’t go viral, it helps to keep your name
top of mind. This is important since people usu-

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 A Skill Called Luck

ally send opportunities to whoever is top of mind

right now.

Also always keep in mind that you don’t need mil-

lions of followers to reap the rewards anyways.

Here’s a useful thought experiment.

Let’s say you have 2000 followers that you got by

posting feel-good platitudes, whereas I only have
two followers called Elon Musk and Paul Graham.
Would you swap accounts?

So think about what kind of people and oppor-

tunities you’d like to have in your life. Then put
yourself out there in ways that attracts them (or at
least doesn’t repel them).

Putting things out there is by far the most effective

networking strategy.

If you do interesting things and share them pub-

licly, you’ll become a magnet. Like-minded peo-
ple will come to you.

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 Jakob Greenfeld

But it definitely also pays off to be proactive about

reaching out to people yourself. So let’s talk about
this next.

Networking

For most people, their personal network is the

main source of luck in their life.
So expanding your network by reaching out to
strangers and nurturing your network by staying
in touch with people are one of those asymmetric
habits that require little effort, time and resources
but have unlimited upside. They are the easiest
and most effective ways to make your life more
serendipitous.
Unfortunately, for most people (me included) this
isn’t something that happens naturally.
So unless you have a solid system, chances are high
that you won’t reach out to people regularly and
miss out on a ton of fun and opportunities.
I’m currently using a daily reminder to reach out
to at least one stranger every day. I simply write a

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 A Skill Called Luck

short comment to their newsletter or send a DM

on Twitter. Often I just say thanks for something
they created. Sometimes I don’t get a reply and
other times an interesting conversation emerges.
If this happens, I invite them to grab a virtual cup
of coffee.

There’s no agenda. Just a natural curiosity to meet

people doing interesting things.

Now meeting new people like this is a great start-

ing put. But as everyone knows, all the magic is in
the follow up.

Derek Sivers has a cool system for staying in touch

with people. He divides all people he wants to stay
in touch with into four categories: A, B, C, D:

• people on the A list are contacted every

three weeks,
• people on the B list every two months,
• people on the C list every six,
• and people on the D list once a year.

Here’s what I do.

I typically spend a few minutes researching what

they’ve been up to recently.

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 Jakob Greenfeld

I check their social profiles, personal websites, and

read or watch any content they published that I
missed.

Then I share a few thoughts or questions.

Most importantly, I always send the kind of mes-

sages I’d like to receive. They’re short, genuine,
and (ideally) helpful. I never try to sell anything
and there’s no agenda other than to keep in touch.

Sometimes I just share a related article or book I

think they might find interesting and sometimes I
offer specific help or advice with a problem they’re
facing right now.

Of course, not everyone publishes content or up-

dates regularly. In that case, I usually just ask what
they’ve been up to lately.

You’d be surprised how many people are really

happy to get these kinds of messages and they of-
ten spark all kinds of deeper conversations.

I wrote about how I implemented Derek Siever’s

system in Airtable a while ago in case you want to
check it out.

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 A Skill Called Luck

(As an aside: The post went viral and Derek, one

of my heroes, actually reached out to me and we
started chatting about our different approaches.
So this is a cool example of how publishing con-
tent can bring more luck into your life.)

21
Chapter 3
SETUP

“The setup is strategy, the act of stacking the odds in

your favor. Life is a game. Like any game, you must
have a good strategy to win. The implementation of
that strategy is called the setup, and it paves the road
to success.” - Dan Bilzerian

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 A Skill Called Luck

You have to let the universe (okay really just other

people) know that you’re receptive for opportuni-
ties and the kind of person that deserves to receive
them.

Most people aren’t receptive. Their email ad-

dresses are hard to find, their direct message in-
boxes closed, they hide their work, and never
talk about their problems, their dreams and what
they’re looking for publicly.

Hence even the tiniest of bat signals you put up

will mag a huge difference and you’ll be surprised
how many opportunities suddenly find their way
to you in the most unexpected ways.

Your setup is simply the sum of all bat signals you

put out there.

The three key factors when it comes to your setup

are visibility, openness, and likeability and you
can work on all three of them in the offline and
online world.

Here’s how.

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 Jakob Greenfeld

Visibility

If you’re working from home, the odds of in-

teresting chance encounters is zero, whereas in
a coworking space or local cafe they’re definitely
higher than that.

And you can increases the odds even further by

choosing a great spot to work in public in. Local
libraries are usually great for focused work sessions
but don’t encourage interactions between people.
Coworking spaces and cafes are usually better but
there are often huge differences between different
places. So it makes sense to create a list of all local
places that cater to laptop workers and then test
them for a day or two until you find one with the
right kind of people and interactions.

Now I’m definitely not saying you should spend

all your time in a noisy cafe or coworking space.
Deep work is important and I spent a lot of time
working at home or at the public library.

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 A Skill Called Luck

But when it comes to types of work that require a

lower level of concentration like writing emails, I
like to do them in a local cafe or rooftop bar.

An hour here or there will definitely increase your

luck surface area.

And it’s not just where you work but also, for ex-
ample, you work out. The serendipity potential in
your home gym is zero, in a regular gym it’s a bit
higher, and in a high-priced gym it’s a lot higher.

Or here’s another example. The odds of a

serendipitous encounter are zero if you’re reading
at home but non-zero if you read a physical book
in a public spot like the local library or cafe.

Many factors will influence decisions like your

choice of a coworking space, gym, or reading spot,
but at the very least make their serendipity poten-
tial one of them.

Even more important than your choice of cowork-

ing space is the city you live in. If you’re in Miami,
San Francisco, New York, or Austin, the chances
that you randomly meet interesting entrepreneurs
are 10x higher than elsewhere. If you’re really seri-

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 Jakob Greenfeld

ous about increasing your luck surface area, this is

arguably the most powerful lever to pull.

To summarize, it’s important not just to be visible

but be visible in the right places.

And exactly the same is true when it comes to the

online world.

Here’s an example of how a proper online setup

can bring opportunities into your life.

Danny Postma is very visible online and shares the

ups- and downs of his entrepreneurial journey on
Twitter daily.

So when the OpenAI team recently launched their

newest API DALL•E they reached out to him and
gave him access.

It’s not hard to understand why. There are thou-

sands of people on their list they know nothing
about, and then there are people like Danny who
work in public. The OpenAI team knows exactly
what they stand for and know that giving them ac-
cess will lead to more exposure for the project.

And yes, getting access early is a huge advantage.

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 A Skill Called Luck

For example, when then OpenAI team launched

GPT-3, people who first got access were able to
build huge businesses like Copy.ai. All they did
was create a user-friendly wrapper around GPT-3
and simply being the first was enough to build a
business that generates millions in revenue.

So chances are high that something similar will

happen with DALL•E and guys like Danny who
thanks to their setup got a headstart clearly have a
huge advantage.

So the idea is exactly the same as in the offline

world. You will dramatically increase your visibil-
ity by working in public. There are in fact virtual
coworking spaces.

Focusmate is cool. I also like the Ultraworking

Work Gym and the WIP.chat.

But there are also far more effective things you can
do that than using one of these skeuomorphic so-
lutions.

One option is to livestream your work on a plat-

form like Twitch or YouTube. But admittedly

27
 Jakob Greenfeld

that’s very stressful as you always have to make

sure you’re not sharing any secrets publicly.

So a better solution is share curated highlights on

Twitter or on your personal site. It’s not only
much less stressful but also will attract more eye-
balls as the signal-to-noise ratio is much higher.

There’s really no reason to overthink it. Remem-

ber we’re not hustling here.

Just share a little snapshot of what you worked on

each day. It could be a screenshot, a diagram, a
random observation, a problem you encountered.

It doesn’t matter if anyone cares or how much

likes you get. The simple act of building in pub-
lic will make people aware of your existence and
keep your name top of mind. And this will lead
to interesting chance encounters and prompt peo-
ple to send opportunities your way.

Working with the garage door up and learning in

public are super cheap options to maximise your
surface area for serendipity to strike.

And of course if you want to put the dial on the vis-

ibility knob to 12, you can get serious about build-

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 A Skill Called Luck

ing an audience. But this requires significant ef-

fort which is why I talked about it in the context
of hustling.

Openness

Openness is all about communicating as clearly as

possible that the bat signals you put up there is an
invitation.

Even in the best gym or coworking space you

will have zero interesting chance encounters un-
less you start signaling that you’re open to having
conversations.

Or rather, the most important thing is to avoid sig-

naling the opposite. Unfortunately, this is what
almost everyone does nowadays by wearing head-
phones.

Headphones are a universal signal: don’t talk to

me. This is of course great if you want to work
uninterrupted but you should be aware that it
shrinks your luck surface area a lot.

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 Jakob Greenfeld

The same is true online if you hide your email ad-

dress and close your direct message inboxes.

To increase your luck surface area, make it as easy

as possible for people to reach you. Your email
address should be displayed prominently on your
website and your DMs should be open for mes-
sages from strangers. If you’re afraid of spammers,
write your email address like this: YourName [at]
gmail.com or use an image.

You can go one step further by explicitly encour-

aging people to reach out to you.

You can do this by putting something like “DMs

welcome” in your bio on social platforms like
Twitter, and adding a corresponding invitation to
your personal website.

I guess you could do something similar offline, for

example, by wearing a t-shirt that says something
like “Talk to me!”.

I personally encourage people on my site to send

me emails. My friend Paul Millerd has a page with
his Calendly link where he invites strangers to no-
agenda Zoom calls. And Nick Gray actually posts

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 A Skill Called Luck

his mobile number and invites people to just call

him.

There are different levels and you’ll have to exper-

iment to find out what works for you.

Likeability

If you see someone on the side of the road holding

their thumb out, trying to get a ride because their
car broke down, you’re not likely to stop. But if
you see someone on the side of the road pushing
their car, you will get out and help push.

People like people who do stuff. The more you

do, the more people will be rooting for you, and
the more great opportunities will come your way.

This is why working in public is so powerful, espe-

cially online, where you can effortlessly share real
glimpses behind the scenes. People will start reach-
ing out to you with advice and suggestions. This
will make them feel invested in your success and
they will motivate them to help you in all kinds of
different ways as well.

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 Jakob Greenfeld

Another factor the car story nicely illustrates is

that the way you present yourself matters a lot.
The odds of getting help will be a lot higher if
you’re dressed well. And this is true offline just as
much as online.

Offline a good rule of thumb is to stick to the

“Hotel Bathroom” dress code. Always dress well
enough to walk into a bathroom at a hotel you’re
not staying at and get away with it. This way you’ll
also always look sharp enough to capitalize on any
serendipitous encounter.

Similarly, online professional headshots and a well-

designed personal website are great starting points.
Another smart thing to invest in is having a com-
pelling origin story readily available. This could
be a podcast, video, or blog post that explains your
background and why you’re doing what you do.

The best origin stories are luck magnets.

Think about it: every superhero comic starts with

his or her origin story. Why? Because it establishes
a connection between the reader and the protago-
nist.

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 A Skill Called Luck

A great origin story is the fastest way to turn a

stranger into someone who cares about what you
do. And people are far more likely to help people
they care about than some random stranger.

One you’ve crafted your origin story in whatever

format, make sure to link to it prominently on
your site and in your social profiles.

A related thing worth thinking about is how

you’re going to make yourself more easily summa-
rizable. The chances that your name comes up in a
conversation is so much higher if you’re “the writ-
ing guy” like David Perell or “the marketing guy”
like Harry Dry or “the guy who founded Nike”.

If you’re not quite sure what your thing is, you

can come up with a narrative aircover. This can be
any kind of project, website, initiative that makes
it easy to explain what you do (while you figure
out what you do).

I did this with my Bootstrap MBA experiment.

It was a catchy name for a personal learning ex-
periment I came up with and my plan was sim-
ply to learn everything I could about bootstrap en-
trepreneurship.

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 Jakob Greenfeld

But it was a perfect narrative aircover. It gave me

an excuse to reach out to people and to this day
people refer to me as the “Bootstrap MBA guy”.
In general thinking about how to became the kind
of person people want to invite to cool stuff is a
very useful exercise.

34
Chapter 4
CREATIVITY

Every great idea you have is a serendipitous event.

But unlike everything else we just talked about,
this kind of luck manifests purely in your mind.

And the good news is that there’s a lot you can do

to increase your inner luck surface area. And yes,

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 Jakob Greenfeld

“increasing your inner luck surface area” is just a

complicated way of saying “becoming more cre-
ative”

When it comes to creativity, there are three key fac-

tors: Input, digestion, processing, and skill.

Input, skill and processing require active doing.

Digestion requires active non-doing.

So let’s talk about how you can use your influence

over each of these factors to increase the number
and quality of ideas you have.

Input

Living in a completely white room without any

form of external stimulation definitely wouldn’t
be healthy. We need external inputs to stay cre-
ative and productive.

However, not all external inputs are equally valu-

able. The quality of your thoughts largely de-
pends on what you choose to focus on.

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Intellectual junk food like most TikTok videos,

Tweets, or YouTube videos has a similarly devas-
tating effect as regular junk food.

So small actions like regularly “marie kondoing”

(aka asking: ”does it spark joy?”) your inputs
go a long way in improving the quality of your
thoughts and ideas.

Another powerful question is “Does the person I

want to be consume this kind of content?”.

I do a monthly audit where I go through the list of

people you following on Twitter, the newsletters I
subscribe to, the shows and movies I watch on TV
and Netflix, the apps I fire up automatically, the
websites I routinely visit.

Unfortunately, it was never harder to keep your

mind tidy and beautiful. We’re constantly bom-
barded with junk from all sides and it was never
more important to be ruthless in defending your
attention.

Think of your mind as a garden. Every piece of

content you consume is a seed you plant. Just in

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a real garden, focus on planting beautiful flowers

and crops by consuming high quality content.

The best ideas and insights, however, usually

emerge in the most unexpected way. It’s an idea
or observation from a completely unrelated field
or a combination of seemingly unrelated ideas that
leads to a breakthrough.

To stick to our gardening analogy, if you want to

see flowers grow that no one else has seen growing
before, you have to be willing to stir things up a
bit and allow for some randomness.

So it definitely can make a lot of sense to leverage

tools like Twitter or TikTok that have serendipity
built in as a feature to some extent. Done right
(by curating the people you follow carefully), so-
cial media can actually be a very cheap option for
increasing serendipitous opportunities.

Now the most obvious problem with intellectual

junk food is, well, that it’s junk. But there’s an-
other reason why it’s problematic. Just like regu-
lar junk food, it leads to overeating. And nothing
affects your ability to come up with great ideas like
intellectual overeating.

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So let’s talk about this next.

Digestion

Like everyone else nowadays I used to immedi-

ately put on my headphones when I left the house
and started listening to some podcast or audio-
book. I used the 30 seconds I was waiting for the
elevator to check my emails. And of course, I al-
ways browsed Twitter or Reddit when I went to
the toilet.

My mind craves distractions and I used to give it

what it wants.

Only recently I realized just how harmful these

seemingly innocent habits are.

Slowly but steadily my thoughts became muddier.

I started experiencing brain fog. For the first time
in my life I wasn’t sure what to do next.

And all of these symptoms went away once I

started taking better care of my attentional space.

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Attentional space is a term used to describe the

scratch pad in our brain that we use to temporarily
store information as it’s being processed.

If you give in to your impulses, you will constantly

fill your attentional space to the brim.

The garden metaphor ones again comes in handy.

Just imagine what happens when you throw thou-
sands of seeds at every square meter every single
day. Nothing could ever grow.

The same is true for your mind. You need to give it

space and time to digest all the inputs. Otherwise,

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 A Skill Called Luck

none of your seeds will ever turn into a beautiful

flower.

Back in the days computers came with a software

called Disk Defragmenter. It was recommended
that you run the program regularly to make sure
the computer doesn’t become too slow.

What the software did behind the scenes is duti-

fully rearrange the discontiguous blocks of files so
they would be physically closer on the drive. This
made the computer faster since when the files are
properly organised on the drive, it takes less time
to open them.

Something similar happens when you leave

enough room in your attentional space. After
some boot-up time, you mind will start dutifully
rearranging the discontiguous blocks it has stored.
In other words, we defragment our thoughts
when we carve out space between tasks.

A lot of it happens beyond the surface but you can

glimpses of what’s going on by noting how seem-
ingly random thoughts start popping into and out
of your awareness.

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 Jakob Greenfeld

If you leave enough room in your attentional

space so that this process runs regularly, your
thinking will improve significantly.

And as if this wasn’t already cool enough, there’s

lots of other good stuff going on.

A byproduct of the defragmentation process is

that your mind tries all kinds of combinations
how different thoughts fit together. If there’s
enough room left in our attentional space, we nat-
urally begin to connect the scattered dots we’ve
collected.

This is where novel insights and ideas come from.

There’s a reason why Bed, Bath, and Bus are called

the Three B’s of Creativity. These used to be
the only places where people’s attentional space re-
mained empty enough. (Nowadays, waterproof
smartphones that we keep using while we lay in
bed kind of ruined these places.)

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Processing

“Your mind is for having ideas, not holding them.”

– David Allen

There’s an incredibly powerful way to how ac-

tively support your minds defragmentation pro-
cess: notetaking.

It allows you to get ideas and thoughts out of your

system to make room for new ones. The more
stuff we get out of our heads, the more clearly we
think.

Lots of ideas are hiding in the shadows and only

come to light once your fingers hit the keyboard.
And once you’re able to see them in bright day-
light, your relationship to them changes instanta-
neously once.

For many people notetaking has turned into some

kind of religion. But honestly, I don’t think de-
tails matter much here. Simply by taking notes,
you get 90% of the benefits. And only if you want

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 Jakob Greenfeld

to squeeze out the remaining 10% you should start

looking into

I personally like to use Roam as its bi-directional

linking features facilitate serendipitous rediscover-
ies of old notes.

Another method to actively defragment your

mind is, you probably guessed it, meditation.

Meditation is simply the process of actively leav-

ing as much room as possible in your attentional
space. Then you observer your thoughts pop into
and out of your mind like an indifferent third-
person observer.

As with notetaking, the details don’t matter much.

The most important factor is that you do it and do
it regularly.

Skill

Ideation isn’t something you can learn by reading

about it. It’s a skill that you learn by doing. You
have to practice to become better.

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 A Skill Called Luck

I really like the analogy of “training your idea mus-

cle” that is just perfect. You can do this by, for
example, writing down 10 ideas every day. This
could be any kind of ideas.

Ideas for books, movies, parties, recipes, experi-

ments, businesses, whatever.

While writing down 10 ideas may sound simple, I

personally always found it extremely hard and was
never able to do it consistently.

The mistake I made was that I tried to come up

with ideas while staring at a blank piece of paper,
waiting for inspiration to strike.

It’s far more effective to have at least some input.

This is why I started collecting useful prompts.

These prompts not only make it so much easier to
come up with ideas, but also help to direct brain-
storming sessions in productive directions.

Here’s are some of my favorite prompts.

• What inefficiencies can be solved by bor-

rowing new technology and applying it to
an older space?

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 Jakob Greenfeld

• What is something where you find yourself

repeatedly saying “I should not have to do
x”?
• What is something that everyone does that
you think is crazy?
• What is something that most people do not
see as being valuable? What is the potential
for it to be valuable?
• What is something every household needs
but doesn’t have?
• What is something that is underrated and
undervalued?
• What is something that’s not broken but
could be improved?
• What is something everyone knows exists
but few people actually do?
• What would be a movie plot that immedi-
ately would make you want to watch it?
• What kind of social event would you love to
attend? What would make it so fun?
• What is something that makes you smile?
Why?
• What is an idea you have that, if made real,
would change the world?

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 A Skill Called Luck

• What would be an amazing new product?

• What is something that you want to learn
more about?
• What is something that you dislike? How
could it be improved?
• What is something that is impossible?
What would be a way to make it possible?
• What is something that you wish everyone
had?
• What is something that you wish everyone
knew?
• What is something that everyone should
do?
• What is something that everyone should
stop doing?
• What could be the next big thing for your
industry?
• What is one thing that would make you
smile every day?
• What do you believe in so strongly that you
would fight for it?
• What is one important thing you want to
make sure happens before you die?

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 Jakob Greenfeld

Now just to be clear, even with the best prompts

most of your ideas will be bad.

That’s simply how it works.

Before you can hope to find any high-quality ideas,

you have to come up with tons of crappy ones.
You need to get them out of your system.

It’s useful to visualize your creativity as a backed-

up pipe of water. The first mile of piping is packed
with wastewater. This wastewater must be emp-
tied before the clear water arrives.

There’s no shortcut other than first emptying the

wastewater.

And since our brains are hardwired for narrative,

here’s a story that illustrates the same idea nicely:

“A ceramics teacher announced on opening day that

he was dividing the class into two groups. All those
on the left side of the studio, he said, would be
graded solely on the quantity of work they produced,
all those on the right solely on its quality. His proce-
dure was simple: on the final day of class he would
bring in his bathroom scales and weigh the work
of the “quantity” group: fifty pound of pots rated

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 A Skill Called Luck

an “A”, forty pounds a “B”, and so on. Those be-

ing graded on “quality”, however, needed to pro-
duce only one pot — albeit a perfect one — to get
an “A”. Well, came grading time and a curious fact
emerged: the works of highest quality were all pro-
duced by the group being graded for quantity. It
seems that while the “quantity” group was busily
churning out piles of work – and learning from
their mistakes — the “quality” group had sat the-
orizing about perfection, and in the end had little
more to show for their efforts than grandiose theories
and a pile of dead clay.”

So if you want to improve your ability to come up

with great ideas, you should take the daily brain-
storming exercise seriously.

Write down at least 10 ideas every day.

The quality of the ideas doesn’t matter. What mat-

ters is that you actually write these ideas down
somewhere and do it daily.

I personally use Notion to collect my ideas but any

notetaking tool or an old-school notebook will do.

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 Jakob Greenfeld

Trust the process. Once the bad ideas are out of

your system, stronger and stronger ideas will begin
to arrive.

Now it’s time to talk about the fourth and final

part of the luck equation.

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Chapter 5
CAPACITY

“Serendipity is not a chance event alone. It is a pro-

cess in which a chance event is seized upon by a cre-
ative person who chooses to pay attention to the event,
unravel its mystery and find a proper application
for it.” - Morton A. Meyers

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 Jakob Greenfeld

It’s not enough to have amazing opportunities

coming your way. You also have to seize them.

While hustle, creativity, and your setup all influ-

ence the number of opportunities that come your
way, your capacity determines the number and
quality of opportunities you’re able to take advan-
tage of.

For example, imagine that someone offers you

to join his extremely promising startup as a
cofounder. But most startups don’t generate
enough profit to pay for their founders’ living ex-
penses for quite a while. So unless you have some
savings, you won’t be able to say yes no matter how
great the opportunity might be. And of course,
the situation is even worse if you have to, for ex-
ample, a mortgage to pay off.

There are five core factors that determine the num-

ber of opportunities you’re able to seize: your
mindset, skills, and freedom.

Out of these, I’d rank mindset as the number most

important factor.

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 A Skill Called Luck

Mindset

“Whether you think you can, or you think you can’t

– you’re right.” - Henry Ford

With a poor self-image, you will most likely sabo-

tage yourself. When someone presents you with
an amazing offer, you’ll say no since you feel like
you don’t deserve it. When a great opportunity
presents itself to you, you will either ignore it or
wait too long since you feel like you’re not ready
yet.

There is an extremely interesting interplay be-

tween your self-image and your setup.

It’s much harder to seize great opportunities if

you’re wearing cheap clothes and work in your
parents’ basement. The way you dress, treat your-
self, and your environment has a direct effect on
your self-image

And if your self-image is that you’re just a ran-

dom dude sitting in his parents’ basement, you
will most likely sabotage yourself.

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 Jakob Greenfeld

But when the same thing happens while you’re

looking sharp and sitting in a nice office, it just
seems completely normal that good things hap-
pen. So you say yes more often and pursue better
opportunities.

Your mindset also has an influence on the number

of opportunities that come your way.

Abundance

Most people feel very quid pro quo about things.

They expect to get back right away, and will often
remind whoever they did a favor for that they did
a favor. And they will definitely never do anything
for others unless it’s obvious how they’re benefit-
ing from it.

There’s no worse mindset if you want to bring

more luck into your life.

It’s a much smarter to simply do nice things for

others without expecting anything in return. Peo-
ple with the a large luck surface area freely spread
the good around since they know it’ll catch up
with them sooner or later.

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 A Skill Called Luck

Of course, most people forget about it when you

do nice things and are ungrateful. But like almost
anything in life, this is a numbers game.

Even if only 1 out of 100 people changes your life in

an amazing way as a result of you paying it forward,
it’s totally worth it.

But the crux is that you never know in advance

who this person will be. Moreover, a quid pro quo
mindset will turn off the most successful and inter-
esting people.

So if you care about serendipity, it really pays off

to have an abundance mindset.

Be friendly, giving, and helpful and don’t expect

anything in return. You’re not looking to get paid
back when you do something nice for someone.
Rather it’s like, do a lot of nice things, and good
karma will catch up with you sooner or later.

Here’s a useful mantra I keep at the top of my daily

todo list: “I’m doing it because it brings into exis-
tence the kind of world I want to live in.”

Positivity, energy, and a bias for action

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 Jakob Greenfeld

No one likes being around negative people.

So being a positive, energetic person goes a long

way if you want to increase your odds of being in-
vited to cool events and being introduced to inter-
esting people.

And yes, this is a choice. With a bit of training

you can direct your emotions in healthy directions
rather than being directed by them.

Before you enter a room or store, you can make

a conscious decision to have a good time, to have
this experience in its fullest, even if it’s something
mundane like getting your traffic licence renewed.

Your can always force the good time out of the av-
erage.

And there are also far too many people that talk
about doing stuff but never follow through. Most
are, rightfully, hesitant to help these kinds of peo-
ple. Hence developing a bias for action and being
a high agency person are key traits if you want to
bring more luck into your life.

And you can develop these traits simply by choos-

ing to do so. Never leave the scene of a decision

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 A Skill Called Luck

without taking some action. Instead of just creat-

ing a long list of contacts, send the first email right
away. Don’t waste time to create fancy business
plan. Set up a simple landing page and start talk-
ing to potential customers. The more you do this,
the easier it gets and the more opportunities will
find their way to you.

Always remember: People like people who do

stuff. The more you do, the more people will be
rooting for you, and the more great opportunities
will come your way.

Skills and Money

“Luck is what happens when preparation meets op-

portunity.” - Seneca

Your skills directly determine the number of op-

portunities you’re able to take advantage of.

For example, if you’re able to code, design, and

launch micro projects in a single weekend, you’ll
be able to capitalize on all kinds of short-term
trends.

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 Jakob Greenfeld

Here’s one of my favorite examples.

In September 2020 Apple announced that it’s

now possible for users to customise their home
screens with custom app icons.

Traf, a designer with strong tech skills who had

started to build a personal brand, noticed that
many people were sharing screenshots of their cus-
tomised screens on Twitter. He already had expe-
rience designing iOS icons, so he decided to put
together a pack for himself. Traf posted his screen-
shot on Twitter and his tweet went viral.

People wanted to know where they could get

Traf’s icon pack. So he decided to capitalize on
the opportunity by selling a pack of 60 icons and
made $100,000 in jus 6 days.

Lots of people noticed this opportunity after Ap-

ple announced the changes but only Traf was able
to take full advantage of it thanks to his design
skills and his ability to set up a sales page in just
a few hours.

The lesson to take away here is that it makes sense

to invest in learning skills that open new doors.

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 A Skill Called Luck

As Traf’s example illustrates being able to quickly

launch and get attention for projects entirely on
your own is an extremely high leverage skill since it
allows you to move much faster than anyone else.

As Naval Ravikant put it succinctly: “Learn to sell,

learn to build, if you can do both, you will be unstop-
pable.”

And you definitely don’t have to become an expert

programmer to 10x the number of opportunities
you’re able to pounce on. Basic skills are enough
to validate most project ideas and there are now
also amazing no-code tools like Bubble you can
use.

Writing (that is copywriting not the stuff you learn

in universities) is another extremely valuable skill
to learn. Being able to craft great cold emails or
write blog posts that go viral is a superpower and
will bring tons of luck into your life.

Another interesting factor besides your skills is

money. Money definitely also allows you to take
advantage of bigger and better opportunities. If
you’re lacking the necessary skills or time, you can
simply hire someone.

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 Jakob Greenfeld

So having more money definitely also increases

your luck surface area even though you probably
didn’t need yet another reasons to care about it.

Freedom

“The secret to doing good research is always to be a

little underemployed. You waste years by not being
able to waste hours.” - Amos Tversky
If you’re calendar is always fully booked and
you’re working a job that requires 100% of your
time and energy, you won’t be able to explore and
seize any new opportunities. Most likely, you sim-
ply won’t recognize opportunities no matter how
opportunities since you’re so busy.
So if you want to bring more luck into your life,
it’s key to allow for some slack.
One of my favorite metaphors is that creative,
ambitious people should work like lions not like
cows.
Lions will sit and they’ll wait. They observe the
surroundings. They wait until they see their prey

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 A Skill Called Luck

appear. And they won’t just run around the aim-

lessly, you know, fake hunting. They wait until
there’s actually prey. Then they sprint and they
sprint until they catch their prey and they hunt it
down. Then they eat and enjoy the fruits of their
labor. Afterward they go back to resting and wait-
ing again.

But it’s not what most people do. What they do

instead is working like a cow. They just stand out
there in the field with their neck down and they
graze on grass all day, eight hours a day, just slowly
chomping up the grass and they don’t really make
much progress.

Now in an ideal world, you’d be able to explore

whatever sparks your interest and go immediately
all-in when you spot a high-value opportunity.
This in turn, would increase your luck surface area
even further, since people will happily tell about
further opportunities since you’re the kind of guy
who’s actually able to do something with it.

For most people this is of course not a realistic op-

tion and the main reason why is money.

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 Jakob Greenfeld

Money equals freedom, at least to some extent. If

you have savings you can afford, for example, to
take off a year to explore new opportunities or to
take a risky bet like joining your friend’s startup.
But there are really two factors at play here: how
much money you have saved and how much you
spend. If you live frugally, even moderate savings
can go a long way.
Now neverthleless how much money you cur-
rently have in your account, it’s worth thinking
about how to bring a bit more slack into your life
and. Already an hour here and there with zero
plans and obligations is a great starting point.

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Chapter 6

THE NEXT STEP: WHERE TO

GO FROM HERE

If you enjoyed this guide, then you’ll probably

love my weekly newsletter. It’s totally free and I
share proven frameworks and strategies for living
a better life.

You can sign up here:

https://jakobgreenfeld.com/newsletter

I don’t have it all figured out, but I’m doing my

best to walk the slow march toward greatness with
you.

Jakob Greenfeld

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 Jakob Greenfeld

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