A Skill Called Luck by Jakob Greenfeld

My Thoughts

This was a great and short read. I really enjoyed it.

There is nothing revolutionary about the content, but it is very nicely structured and reminds you of the important things in a very structured maner.

This one is good for re-reading from time to time.

In fact, I’ll go as far as to say that this is what many books should be.

Straight to the point. Direct, no fluff. Nicely structured.

When I end up writing a book, it will hopefully look like this.

Summary

A Skill Called Luck argues that “luck” is not something you wait for. It is something you can deliberately cultivate by increasing your luck surface area and making yourself the kind of person who notices, attracts, and capitalizes on opportunities.

You can’t control outcomes, but you can stack the odds by putting yourself in environments where chance encounters happen, by signaling what you’re working on, and by making it easy for others to help you.

Jakob’s framework is built around four levers:

Hustle

• ship work publicly
• tell people what you’re doing
• proactively expand/nurture your network—reach out to strangers consistently

Setup

• optimize visibility, openness, and likeability through environment and presentation
• access—work from places where people are
• keep DMs/email open
• share daily progress

Creativity

• protect attention by cutting “intellectual junk food,”
• use prompts to generate better ideas

Capacity

• build the mindset, skills, and freedom to seize opportunities—abundance mindset, positive energy, self-image, and practical skills like building, selling, and copywriting.

The throughline: serendipity can be engineered when your output is visible, your door is open, and your capabilities let you say “yes” when luck appears.

Learnings

• Luck is a skill: you can’t guarantee outcomes, but you can systematically increase the probability of good breaks.
• Increase your luck surface area by making your work visible—unfinished/private projects can’t create opportunities.
• Hustle ≠ grinding in silence; it means doing the work and telling people about it.
• Your network is the biggest compounding “luck engine”; expand it deliberately and keep it warm.
• Use a simple habit: reach out to one new person per day (reply to a newsletter, send a thoughtful DM, say thanks).
• “Engineer serendipity” by stating what you want publicly. Audiences often turn wishes into introductions and solutions.
• Optimize your setup around three traits: visibility, openness, and likeability (online and offline).
• Physical environment matters: spend some low-focus work time in places where chance encounters are possible (cafes, coworking).
• Geography is leverage: living in a high-density opportunity city can multiply serendipity.
• Work in public: share small daily snapshots (screenshots, notes, diagrams, observations) to invite advice and collaboration.
• Remove friction for inbound: show your email clearly, keep DMs open, and explicitly invite people to reach out.
• Be aware of “anti-luck signals” (e.g., headphones) that reduce approachability in the real world.
• Presentation affects opportunity capture: self-image and how you show up (dress, environment, headshots, website) change what you say yes to.
• Maintain a ready-to-share origin story (post/podcast/video) that explains who you are and what you’re building—good stories attract help.
• Protect creativity by cutting “intellectual junk food”; high-volume low-quality inputs crowd out original thought.
• Run periodic input audits (feeds, newsletters, shows, apps) and keep only what aligns with who you want to become.
• Give your mind space: fewer inputs → more digestion → better ideas (the “garden” metaphor).
• Use prompts to generate opportunities and product ideas; better questions produce better luck.
• Build “capacity to seize luck”: mindset + skills + freedom determine whether opportunities turn into results.
• Adopt an abundance mindset: be generous, helpful, and positive without keeping score—this increases invitations and introductions.
• Enter rooms intentionally: decide to have a good time and be engaged; energy is a practical advantage.
• Learn durable leverage skills—build + sell is a powerful combo; add copywriting to create opportunities via clear communication.

‘How to Read a Book’ Analysis

Key Sentences

1. “You can wait passively and hope that the world will eventually recognize your genius. Or you can develop and execute a plan to actively increase your luck surface.”

   • Why it’s crucial: Frames the book’s central claim: luck is not just randomness; it’s something you can influence through deliberate behavior.
   • Proposition: Treat luck like a skill—design systems and habits that increase the frequency of opportunities.

2. “It’s always possible to stack the odds in your favor. You can actively create optimal conditions for lucky things to happen to you.”

   • Why it’s crucial: Establishes the practical, probabilistic mindset: no guarantees, but controllable inputs.
   • Proposition: Focus on controllables (exposure, environment, relationships, skills) that raise expected value.

3. “Hustle is about proactively bringing more luck into your life… it’s always about people.”

   • Why it’s crucial: Redefines hustle away from isolated grinding and toward social distribution and connection.
   • Proposition: Convert output into opportunity by routing it through people (sharing, networking, asking, collaborating).

4. “Doing a ton of work without ever telling anyone about it won’t open any new doors for you.”

   • Why it’s crucial: Names the most common failure mode: hidden work has near-zero surface area.
   • Proposition: Publish and share by default; distribution is part of the work.

Unity of the Book

Luck isn’t a mysterious force reserved for a few. It’s an outcome you can systematically increase by making yourself more discoverable, approachable, and capable, so that chance events happen more often and you’re able to seize them when they do.

Prompt / Agent Ideas

1. Daily Luck Surface Agent (Visibility + Outreach) Goal: Make “one small public output + one new connection” automatic.

• Inputs: What you worked on today (bullets), links/screenshots, who you follow, current goals.
• Outputs:
  • 1 “work-in-public” post draft (X/LinkedIn/Threads)
  • 1 short newsletter snippet (2–4 sentences)
  • 3 candidate people to reach out to + a tailored message for each
• Prompt skeleton:

  You are my Luck Surface Agent. Turn today’s work notes into (1) a short public progress post, (2) a slightly longer reflection for my newsletter, and (3) three outreach messages to relevant people. Constraints: be specific, non-cringy, and include a clear “hook” (problem/insight/lesson). Outreach messages must include a genuine reason, one concrete compliment, and a low-friction question.

2. Serendipity Ask Agent (Make Wishes Known) Goal: Regularly broadcast what you want (help, intros, feedback).

• Inputs: Current project + bottleneck + ask type (intro, feedback, customer, job, collab).
• Outputs: A “serendipity request” post + 3 variations + a DM version.
• Prompt skeleton:

  Draft a public ask that signals what I’m building, what I’m stuck on, and how someone can help in <30 seconds. Provide 3 tones: (a) casual, (b) direct, (c) story-based. End with a simple CTA.

3. Network Warmer Agent (Nurture Relationships) Goal: Keep your network warm with minimal effort.

• Inputs: A list of 30–200 people + last interaction + context notes.
• Outputs: Each week: 5 “reach-out” suggestions + message drafts.
• Prompt skeleton:

  You are my Relationship Nurturer. Pick 5 people I should reconnect with this week based on time since last contact and relevance to my goals. Draft a short message that references our shared context and includes either a useful link, an offer to help, or a thoughtful question.

4. Coworking/Cafe Scheduler Agent (Offline Luck Surface) Goal: Nudge you into higher-serendipity environments without wrecking deep work.

• Inputs: Calendar, tasks list tagged as Deep vs Shallow, preferred venues.
• Outputs: A weekly plan: 2–4 “public” work sessions for shallow tasks + 1 event suggestion.
• Prompt skeleton:

  Plan my week to maximize serendipity without harming deep work: schedule shallow-work blocks in public places, protect deep-work blocks at home/library, and suggest one event/meetup aligned with my interests.

5. Openness/Friction Audit Agent (Inbound Setup) Goal: Make it easy for people to reach you.

• Inputs: Website/about page text, social bios, contact settings, Calendly link, “about me” doc.
• Outputs: A checklist of friction points + rewritten bio/contact copy.
• Prompt skeleton:

  Audit my online presence for openness. Identify where a stranger would fail to contact me or understand what I do. Rewrite my bio, add a clear CTA, draft a “Contact” page, and suggest DM/email settings + anti-spam formatting.

6. Origin Story / Luck Magnet Agent Goal: Create a compelling “why me, why now” asset you can point people to.

• Inputs: Your background timeline + current mission + proof points.
• Outputs:
  • 1 long-form origin story post (800–1500 words)
  • 1 short version (200 words)
  • 1 podcast-style intro (60 seconds)
• Prompt skeleton:

  Write my origin story to maximize clarity, credibility, and approachability. Include: turning points, what I believe, what I’m building, and how people can collaborate with me. Avoid hype; favor specifics.

7. Input Diet Agent (Creativity + Attention) Goal: Reduce “intellectual junk food” and improve idea quality.

• Inputs: Subscriptions/follow list, screen time/app list, newsletters, YouTube channels.
• Outputs: Monthly: keep/cut recommendations + replacements aligned with “the person I want to be”.
• Prompt skeleton:

  Review this list of inputs. For each, classify as: Nourishing / Neutral / Junk. Recommend what to unfollow/unsubscribe, what to limit, and what to replace it with given my goals. Provide a 30-day input diet plan.

8. Idea Prompt Generator Agent (Creativity Prompts) Goal: Turn the book’s prompt list into a recurring idea pipeline.

• Inputs: Industry, interests, annoyances, things you “shouldn’t have to do”.
• Outputs: 10 prompts/week + 3 “best bets” expanded into mini-briefs.
• Prompt skeleton:

  Generate 10 prompts tailored to me using the Greenfeld-style questions. Then pick the 3 most promising and expand each into: problem, audience, why now, simple MVP, and distribution angle.

9. Skills-to-Luck Roadmap Agent (Capacity) Goal: Build “seize-the-opportunity” capacity (sell/build/write).

• Inputs: Current skills, goals, time budget, projects.
• Outputs: A 6-week roadmap with weekly projects that produce visible artifacts.
• Prompt skeleton:

  Design a 6-week plan to increase my opportunity-seizing capacity. Focus on (a) selling, (b) building, (c) copywriting. Each week must produce one public artifact and one outreach action.

10. Pre-Room Energy Agent (Mindset + Likeability) Goal: Ritualize “choose to have a good time / be open” before social situations.

• Inputs: Event type, people attending, your goal (meet 2 founders, reconnect, etc.).
• Outputs: A 2-minute pre-event script + 3 conversation openers + follow-up plan.
• Prompt skeleton:

  I’m about to enter [event]. Give me a 2-minute mindset reset to be warm, curious, and high-energy, plus 3 openers and 5 questions. Then produce a follow-up checklist and 2 follow-up message templates.

Highlights

Introduction

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

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 following chapters, I’m going to show you how.

Hustle

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 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.

The chances that the software you coded will become 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.

Entire careers have been built on a few pieces of content that went viral.

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 engineering serendipity.

If you have an audience, you can often manifest 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.

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.

I’m currently using a daily reminder to reach out to at least one stranger every day. I simply write a 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.

Of course, not everyone publishes content or updates regularly. In that case, I usually just ask what they’ve been up to lately.

Setup

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.

If you’re working from home, the odds of interesting chance encounters is zero, whereas in a coworking space or local cafe they’re definitely higher than that.

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.

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.

Even more important than your choice of coworking 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 serious about increasing your luck surface area, this is arguably the most powerful lever to pull.

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.

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.

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 messages from strangers. If you’re afraid of spammers, write your email address like this: YourName [at] gmail.com or use an image.

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.

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, especially online, where you can effortlessly share real glimpses behind the scenes. People will start reaching 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.

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 compelling 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.

4 Creativity

Intellectual junk food like most TikTok videos, Tweets, or YouTube videos has a similarly devastating 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?”.

Note: Questions to ask yourselves to make you a better person.

I do a monthly audit where I go through the list of people I follow 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.

The garden metaphor ones again comes in handy. Just imagine what happens when you throw thousands 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, none of your seeds will ever turn into a beautiful flower.

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 brainstorming sessions in productive directions.

Here’s are some of my favorite prompts.

• What inefficiencies can be solved by borrowing new technology and applying it to an older space?

• 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 immediately 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?

• 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?

Note: Prompts for thinking

Capacity

“Serendipity is not a chance event alone. It is a process in which a chance event is seized upon by a creative person who chooses to pay attention to the event, unravel its mystery and find a proper application for it.” - Morton A. Meyers

There are four core factors that determine the number of opportunities you’re able to seize: your mindset, skills, and freedom.

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 yourself, and your environment has a direct effect on your self-image

And if your self-image is that you’re just a random dude sitting in his parents’ basement, you will most likely sabotage yourself.

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 happen. 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.

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 existence the kind of world I want to live in.”

So being a positive, energetic person goes a long way if you want to increase your odds of being invited to cool events and being introduced to interesting people.

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 driver’s licence renewed.

As Naval Ravikant put it succinctly: “Learn to sell, learn to build, if you can do both, you will be unstoppable.”

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.