Luck, By Design

Build surface area, read weak signals, and move before consensus

I. The Luck Lie: Why Effort ≠ Opportunity

There’s a certain kind of person who believes they can earn luck. They wake up early, block their calendar, hit their OKRs, cross off every task on their Notion board, and deep down, they believe that if they just keep doing everything “right,” things will click.

And sometimes, they’re right. But often, they’re not.

Because in real life, effort doesn’t always translate to opportunity. Some of the most competent, committed people I’ve met are still waiting to be “discovered.” Still waiting for the right person to notice. Still waiting for all their preparation to convert into momentum.

And then there’s someone else, maybe not as polished, maybe newer to the space, who stumbles into the right room at the right time. Or posts something on a whim that lands perfectly. Or meets someone on a random Thursday who opens a door that changes everything.

It looks like luck. And it is.
But not the kind you sit around waiting for.

The mistake we make is thinking luck is the opposite of hard work. It’s not. The real tension is between two models of success:

• The hustle model, where you grind your way to the top, and

• The genius model, where you’re such a prodigy that people can’t ignore you.

Both are deeply flattering. They let us believe that if we’re either relentless or brilliant enough, the world will reward us. But both leave out the third, far more common reality: most opportunities emerge in the middle. In the gaps, the overlaps, the odd little moments that don’t fit on a vision board.

If hustle is doing, and genius is being, then luck is noticing.

Noticing is amorphous. It’s not easily measurable. It doesn’t feel like progress in the traditional sense. But it’s the skill that turns “I was just talking to someone about this!” into a funded company. Or “I saw this weird thing three times this week” into a product pivot.

What we call “luck” is often just pattern fluency: the ability to pick up on something before it calcifies into consensus.

And if you believe this assertion, you’ll believe what I’ll say next: That kind of luck can be trained.

If you want more opportunities, the answer isn’t just to work harder. It’s to increase what I call your serendipity surface area: the total number of places, people, and ideas you’re exposed to, plus your readiness to act when something sparks.

Think of it like building a giant radar dish. Every time you meet someone new, ask a better question, try something slightly outside your comfort zone, you’re increasing the likelihood that something interesting finds you. But more than that, you’re increasing the likelihood that you’ll actually recognize it when it does.

Luck, I have come to realise, isn’t passive. It’s interactive. You don’t just “get lucky.” You notice a half-formed opportunity, you’re brave enough to follow it, and you have enough proof under your belt to act without needing permission.

That’s trained serendipity. It’s not random. It’s just not linear.

I’ve seen it happen over and over again with founders, operators, even investors. The people who seem to catch every wave aren’t magically gifted. They’ve just built better habits of exposure and recognition. They’re not waiting for perfect conditions. They’re tuned to anomalies. They’ve learned that most big breaks don’t feel like big breaks at the time. They are likelier to feel like a passing comment, or a weird pattern, or a moment of curiosity that pulls you off-course.

And instead of dismissing that moment, they pursue it.

This piece is about that pursuit.

It’s not about manifesting. It’s not about productivity hacks. And it’s definitely not about sitting at your laptop 12 hours a day waiting for the universe to reward your effort.

It’s about shifting how you think about attention, experimentation, and intuition so that when the world gets a little weird (and it always does), you’re the one who spots the crack in the surface. You’re the one who follows the thread.

Because if you want to play long games, luck will be part of the equation whether you like it or not. But it doesn’t have to be out of your hands.

You can train your mind to see faster. You can design your days to invite more intersections. You can take the pressure off one big bet and give yourself dozens of small ways for something unexpected to click.

This is the game you’ve been added to as Player Number 2. You can choose to be angry about it, or you can learn how to get good at it. The earlier you learn to play it, the less burned out and the more dangerous you become.

So no, this isn’t going to be one of those “how to optimize your career in 10 easy steps” pieces. You’re too smart for that. But it is going to walk you through how luck actually works (neurologically, behaviorally, creatively), and how you can shift your attention in ways that change your entire trajectory.

If you’ve ever looked at someone else’s career and thought, “Why not me?” then this is for you.

Because “lucky” people aren’t chosen. They’re ready.

And by the time you finish this piece, you will be too.

II. How Your Brain Sees Patterns (and Misses Them)

Let’s talk about attention. Not in the productivity sense, but in the “why did I miss that huge opportunity when it was right in front of me” sense.

Because your brain doesn’t show you the world. It shows you what you’re looking for.

There’s a cognitive concept called attentional set, which is just a fancy way of saying your brain filters for what it thinks matters. It’s like walking around with invisible post-its on your forehead that say “show me people who seem useful,” or “alert me if someone mentions a job opening,” or “I’m terrified of looking dumb, so let’s avoid risk.”

Most of us don’t choose those filters consciously. They’re shaped by anxiety, bias, old goals we forgot to delete from our operating syste,. Which means we’re often missing stuff, the good stuff, because our mind literally isn’t wired to notice it.

And when you’re building a career, or a company, or just trying to not feel stuck, that filter matters a lot.

You can be in the same room, on the same call, scrolling the same feed as someone else, and they’ll catch the glimmer of something- a pattern, a phrasing, a gap- that you completely miss. Not because they’re smarter, but just because their attention is tuned to a different frequency.

That’s what luck actually looks like in action. It’s not a lightning bolt. It’s a “Huh, wait a second” moment that your brain flags before it disappears.

The good news? You can train for that.

Let’s break it down.

Your Brain Is a Pattern-Making Machine (But It’s Lazy)

One of the brain’s core functions is to detect patterns. That’s how you recognize faces, navigate cities, finish each other’s sentences. But the thing about pattern recognition is it’s inherently conservative. Your brain wants to predict what comes next based on what it’s seen before. It rewards efficiency, not accuracy.

That’s useful when you’re parallel parking. It’s not so useful when you’re trying to build something new.

Because when your brain gets too comfortable, it stops scanning for difference. You stop noticing outliers. You start projecting patterns where they don’t exist (that’s called pattern projection, and it’s how people end up chasing trends that aren’t real).

The trick is to stay in a cognitive zone that allows for surprise. That’s where novelty comes in.

Novelty Is Fuel (But Only If You Know How to Use It)

You’ve probably heard that novelty activates the brain’s dopamine system. That’s true. But what matters more is what novelty does. It opens a window. It says, “Hey, this might matter! Pay attention!” That’s why you feel a jolt of interest when someone tells a story that doesn’t follow the script. Or when a product pitch breaks the usual rhythm. Your brain leans in, looking for new meaning.

But (and this is where most people sabotage themselves) we’re often taught to tune novelty out. Especially in ambitious environments. We’re told to stay focused, ignore distractions, specialize early, streamline everything. So we become hyper-efficient at processing what we already know, and borderline useless at engaging with what we don’t.

And in that process, we lose our sensitivity to weak signals. The very signals that often lead to original ideas, unexpected partnerships, or serendipitous insight.

If you want to train luck, you need to intentionally reintroduce novelty into your mental diet. Follow people who think differently. Read things outside your field. Watch someone work through a problem you don’t understand, not because you want to master it, but because it teaches your brain to stay curious.

Ambiguity Tolerance

There’s another psychological muscle that gets overlooked in all this, and it’s a big one: Tolerance for ambiguity.

Put simply, some people panic when they don’t know the answer. Others get curious.

The latter group tends to stumble into interesting territory more often, not because they’re braver, but because they can sit with confusion without rushing to shut it down.

And this matters because almost every lucky break starts as an ambiguous input. A weird email. A half-baked question. A signal you’ve seen three times but don’t know what to make of yet.

If your instinct is to resolve it quickly or ignore it, you miss the moment. But if you can hold it gently, cup it in your palms, give it space to evolve, you give luck a longer runway.

Ambiguity tolerance is trainable too. One simple way? Practice asking better questions. Not “what is this?” but “what else could this be?” Not “how do I solve this?” but “what am I not seeing yet?” Questions like that keep your mental aperture open, and keep you from locking into obvious patterns too early.

Attention Is a Political Act

One more thing, especially if you’re someone who’s been socialized to stay in line, or not take up too much space:

Your attention is power.

What you notice, and what you choose to validate, shapes the opportunities you pursue, and also the ones you give others. It shapes which risks feel reasonable. Which insights feel “professional.” Which patterns you trust.

And that means reclaiming your attention. Not just from your phone, but from everyone else’s expectations.

You don’t need to become a different person to get luckier. You just need to get better at noticing.

So the next time you feel like someone else is “always catching a break,” ask yourself: What were they paying attention to, that you weren’t?

And then go train your eye.

III. Luck Loves Motion: The Behavioral Science of Serendipity

There’s a moment that happens after every panel, pitch, or podcast Q&A. Someone raises their hand and says, “But how do I get noticed?”

They don’t mean it in a desperate way. They’re not asking for a shortcut. They’re asking something more fundamental: how do you position yourself so that good things start happening to you, not just because of you?

Because the truth is, luck shows up most often for people who are already in motion. Not frantically grinding. Not performing productivity on LinkedIn. Just... moving. Across ideas, conversations, formats, fields. Moving enough that something unexpected can find them.

We treat luck like weather. Maybe you get caught in a downpour, maybe you don’t. But that’s not how it works. Motion increases your surface area. And surface area increases your odds.

What Lucky People Actually Do

Psychologist Richard Wiseman spent years studying self-described “lucky” people. His findings were surprisingly simple: lucky people aren’t more gifted, or more extroverted, or more strategic. They’re just open. They talk to more strangers. They try more things. They’re more comfortable with detours, and more responsive to little changes in their environment.

The lucky ones aren’t manifesting. They’re noticing. And the reason they’re noticing is because they put themselves in more situations to notice things in the first place.

That’s what most self-help advice tends to gloss over. It treats opportunity like a vending machine: do the work, follow the steps, and eventually the thing you want will drop. But opportunity rarely follows that script. It’s a side door. A misdirect. A “this is probably nothing, but…” conversation that turns into something big.

If you want more of those moments, you need more collisions. That means putting yourself in spaces where something weird, useful, or slightly out-of-place can happen.

Why Your Closest Friends Probably Won’t Change Your Life

Your closest friends are not the ones who’ll introduce you to the opportunity that changes everything.

Your closest people know the same people, read the same things, apply to the same jobs, follow the same paths as you do. They’re not going to show you a new map because they’re already on yours.

The people who change your trajectory tend to be weak ties: the coworker from two jobs ago, the person you met once at a conference, the mutual who replied to your story with something sharp. A 2022 study of millions of LinkedIn connections proved this. People who had access to more weak ties were significantly more likely to get new roles, better referrals, and faster promotions.

Weak ties act like bridges. They connect you to new information, different priorities, other problems worth solving. That’s why luck often comes through them. Not because they know you well, but because they know something you don’t. Because they are on a map different than yours.

So if you’re serious about increasing your exposure to opportunity, your job isn’t to network harder. It’s to spend more time in slightly strange rooms. To make small talk, and lots of it. To be easy to spend time with. It’s to connect, without an agenda, to people who aren’t already swimming in your feed.

Doing * Telling: The Luck Equation That Actually Works

Founder Jason Roberts coined a formula I think about constantly: Luck Surface Area = Doing * Telling.

It’s a simplified, stupidly obvious equation that breaks down the concept of Return on Luck by Jim Collins, the author of Good to Great.

Most people either bury their work in silence or over-explain something they haven’t actually done. Neither works. Real momentum happens when you do something interesting and let people see it.

This doesn’t mean shouting into the void. It means putting small signals out into the world: a screenshot, a reflection, a question, a short write-up, a DM. When you tell the world what you’re paying attention to, the world gets a chance to answer back.

Visibility is not vanity. It’s the doors you open to let serendipity in.

Motion Is Intellectual, Social, and Creative

When I say luck loves motion, I don’t mean you need to attend every mixer or start a podcast. I mean your thinking needs to be in motion. Your conversations. Your creative risks. Your capacity to try a different format, talk to a new collaborator, explore a thread that doesn’t “fit” the plan.

You don’t get more interesting by becoming a specialist in your bubble. You get more interesting by collecting references from other contexts. By reading things you don’t fully understand. By talking to people who see your industry from a strange angle. From people who might be skeptics of your belief. Those inputs don’t dilute your focus. They give your brain more raw material to work with when something new tries to take root.

Motion, in this context, means not being so optimized that you can’t see the sidetrack. It means leaving slack in your calendar, ambiguity in your thinking, and air in the system so that something unplanned can breathe.

Companies Get Lucky the Same Way People Do

Pixar didn’t become Pixar because it was Pixar. It became Pixar because Steve Jobs insisted on designing their office around collisions. Everyone had to pass through a central atrium. He even tried to centralize the bathrooms. Why? Because he knew that spontaneous hallway conversations, especially between departments that didn’t usually talk, were more valuable than another calendar block.

Slack was born from a failed game. Flickr was a side feature. PayPal only took off when they noticed unexpected traction on eBay. These weren’t random acts of brilliance. They were teams paying attention while in motion. As they built what they had planned, they were open, and consciously so, to the weird little signal that something else might work better.

Motion doesn’t just increase momentum. It increases optionality. It gives you more shots. And more importantly, it teaches you how to recognize the good ones.

If you’re not sure how to get luckier, don’t overthink it. Don’t obsess over outcomes. Start by moving. Talk to someone new. Try a different input. Ship a half-done idea. Share something you’re unsure about.

You don’t need a five-year plan to get discovered. You need surface area.
And that only comes from motion.

IV. From Accidents to Algorithms: How Founders Train Luck

There’s a persistent myth in startup culture that the biggest ideas arrive fully formed. That some brilliant founder had a eureka moment, pitched it perfectly, and the rest was history.

That version of the story is convenient. It makes investors feel clairvoyant and founders feel heroic. But it’s rarely true.

Most breakout products, the ones we now describe as obvious, inevitable, category-defining, didn’t start that way. They started as something else. Something slightly wrong. Or slightly early. Or slightly misdirected. And what made them work wasn’t the original idea. It was the way the team responded to what they noticed.

Luck, in these cases, wasn’t an external blessing. It was internal calibration.

Instagram Didn’t Win Because It Was New. It Won Because It Was Paying Attention.

Instagram began as a clunky app called Burbn, a check-in tool overloaded with features: locations, plans, points, badges, photo sharing. It had loyal users, but engagement was scattered.

So the team did something most founders don’t. They paid attention to what users were actually doing. And what they were doing was posting filtered photos.

That feature, a secondary afterthought, was delivering disproportionate joy. People loved seeing their lives through a curated lens.

So they stripped everything else.
The check-ins. The gamification. The noise. All gone.

And then launched a single-function app focused on filtered photo sharing.

The pivot wasn’t divine inspiration. It was data + instinct + courage to let go of the original vision. They didn’t fall in love with the problem. They fell in love with the pattern.

Slack Wasn’t a Brilliant Idea. It Was a Failing One That Redirected.

Stewart Butterfield’s team wasn’t building a messaging platform. They were trying, once again, to launch a game. It wasn’t working.

But they’d built an internal chat tool to coordinate as they worked. And everyone loved it. So much so that when the game flopped, the team still wanted to keep using the chat.

That tiny clue (internal delight, frictionless adoption) was enough for Butterfield to shift the whole business.

Slack became Slack not because they solved a problem they set out to tackle. But because they were alert enough to repurpose something they built for themselves.

Most people wouldn’t have noticed. Or they would have been too proud to admit that the “real” product had failed. But again, trained serendipity isn’t about ego. It’s about adjusting your eyes fast enough to see what’s working before the rest of the world does.

Post-it Notes Were a “Failed” Invention Until the Pattern Changed

At 3M, a scientist named Spencer Silver created an adhesive that didn’t quite stick. It wasn’t strong enough. By traditional R&D standards, it was a dud.

But years later, another 3M engineer, Art Fry, was frustrated that his paper bookmarks kept falling out of his hymnal during choir practice. He remembered the weak adhesive and thought: what if “not sticky enough” was actually the point?

He used the glue to hold his bookmarks in place. They stayed put. And could be removed cleanly.

From that simple reframe came one of the most successful office products in history.

The magic wasn’t in the product. It was in the noticing. In being curious about the “failed” thing, and seeing it in a new context.

Pattern Recognition Is Discipline.

In each of these stories, what looks like luck is actually a repeated discipline:

• The discipline to observe real behavior instead of clinging to the plan.

• The discipline to validate early signals, even when they come from unexpected places.

• The discipline to act decisively, especially when it means killing your darling.

None of these founders won because they were right from the beginning. They won because they were faster at recognizing what was actually happening under the bluster.

And that’s the real skill here. It’s not clairvoyance. It’s trained flexibility.
You don’t need to have the best original idea. You need to be the best at adapting your idea in response to what’s emerging.

Your First Idea Isn’t Precious. It’s a Probe.

The faster you treat your early ideas as probes, or things designed to surface signals, not win on the first try, the easier it becomes to spot patterns in the chaos.

A good founder doesn’t force the market to match their vision. They use their vision to listen differently. To interpret what’s resonating.

And when they see a spike in behavior, in adoption, or in emotion, they know that’s not a fluke. That’s a thread to pull.

That’s what separates the founders who build one thing and burn out, from the ones who build things that last.

V. Enter the Flâneur: A Philosophy of Wandering With Intent

Before we had frameworks and funnels, we had wanderers.

In 19th-century Paris, a literary figure emerged: the flâneur. He wasn’t a worker, or a planner, or even a participant. He was an observer. A curious, drifting presence on the streets. The flâneur walked through the city not to get anywhere, but to see. To notice what others ignored. To pick up on the rhythms of a place, the subtle shifts in mood, the moments that escaped more purposeful people.

It was indulgent. It was aimless. It was, exactly because of that, strategic.

The flâneur didn’t believe insight came from effort. He believed it came from attention. And not the kind of attention that scans for confirmation. The kind that opens itself to contradiction. To detours. To the idea that what’s worth noticing might be off to the side, or even behind you.

There’s something radical about that. Especially now.

Because today, the dominant logic of ambition is focus. Pick a niche. Block distractions. Move in straight lines. Any deviation from your plan is framed as a weakness, as a lack of discipline. But the truth is, most original ideas don’t arrive through focus. They arrive through a collision. You walk into a thought you didn’t expect. You overhear a comment. You follow a hyperlink you can’t explain. And suddenly, something clicks.

That’s flânerie. And it’s not random. It’s designed openness.

Wandering as Method

This kind of deliberate wandering isn’t laziness. It’s a canvas for insight. It gives your brain raw material. It creates space for novelty. It’s the difference between digging a deeper hole in the same spot and scanning the landscape for a better place to dig.

During what researchers call “mind-wandering”, often triggered by walking, ambient activity, or gentle boredom, the brain activates its default mode network. This network isn’t idle. It’s deeply creative. It connects ideas across domains. It sorts fragments. It generates new associations.

Which explains why ideas tend to show up in the shower, on walks, in line at the grocery store. When you stop forcing progress, your mind starts making connections.

That’s what flâneurie cultivates. It’s not about escape. It’s about composition.

The Flâneuse Had to Fight for Her Place

Of course, the flâneur was historically a man. He could move through public space without question. He had the privilege of lingering. Of looking. Of not being looked at.

Women didn’t have that. In 19th-century Paris, a woman walking alone was often treated as an object, a threat, or a curiosity. The idea that she could simply observe without being observed was almost impossible. That’s why, for years, critics insisted that the flâneuse didn’t exist.

But she did. She just had to be stealthier.

Writers like Virginia Woolf, artists like Sophie Calle, and more recently, thinkers like Lauren Elkin have reclaimed the flâneuse as a serious cultural force: not just a wanderer, but a challenger of constraints. For them, flânerie isn’t just a method of noticing. It’s a refusal to be confined to expected spaces and narratives. Closer home, a book incredibly close to my heart is Why Loiter by Sameera Khan, Shilpa Phadke and Shilpa Ranade, a study of how access to public spaces leads to equitable citizenship. I’d argue that the same conversation can be extended to luck. Access to the ability to explore, both temporal and physical spaces, leads to equitable access to luck.

Because choosing to explore, to walk a different route, to ask the strange question, to follow a lead without immediate ROI, is still coded as indulgent. Or unserious. Or naïve. And yet, those are often the exact moves that surface the best ideas.

Flânerie, then, becomes a way to resist over-scheduling, over-performing, over-defining your life before it’s had time to unfold.

Structured Wandering for Startups and Careers

You don’t need to live in Paris to wander well. You need to design for mental and environmental drift that can live even inside a packed calendar. You need what I’d call structured wandering: time carved out to engage with the unfamiliar.

For a founder, this might mean sitting in on a support call once a week, even when it’s not “efficient.” For a product designer, it might be watching users interact with an unrelated tool. For a strategist, it might be reading outside their domain (fiction, food history, digital subcultures), not to steal ideas, but to increase dimensionality of thought.

Because when you wander, you collect references. And those references give you leverage.

They help you draw analogies others miss. They give you language that resonates outside your own echo chamber. They let you adapt faster, market smarter, and build in ways that don’t rely on stale templates.

You must be able to sway. Osccilate between intent and openness. Between making progress and making sense.

You don’t need a map for everything. But you do need to keep moving through new territory.

In Praise of Leaving the Plan

Flânerie is a fundamentally human activity. It acknowledges that we don’t always know what matters in the moment, and that meaning often reveals itself in hindsight. I’d argue that meaning-making is, unto itself, a process of retrospective narrative. Leaning into this reality makes you open your eyes and ears to things you’d process away otherwise.

That offhand comment in a meeting. That TikTok that won’t leave your brain. That quote you saved six months ago and now suddenly understand. Flânerie is what makes those things stick. It’s the mental habit of saying: “That’s odd. Let me hold onto it.”

In a culture obsessed with strategy and precision, the willingness to follow a hunch feels scary. But in practice, it’s the fastest route to original insight. It’s how you end up ahead of the curve, because you reshaped your curve.

So yes, there’s a time for execution. For rigor. For ship-it energy.

But there’s also a time to walk slowly. To pause on something weird. To let your inputs get a little messier before you try to make them clean again.

That’s not wandering off course. That’s how you expand the course itself.

VI. Feminist Serendipity: Why Leisure and Curiosity Are Power

If you’re a woman trying to build something, you’ve probably absorbed the same narrative I did: That in order to be taken seriously, you have to be serious. All the time.

Head down. Deliver. Don’t ask dumb questions. Don’t take up too much space. Be the most prepared person in the room. Stay polite, stay sharp, stay busy.

And if you work hard enough, if you prove yourself enough, if you keep showing up, then eventually, maybe, someone will give you permission to slow down.

This is the lie.

You miss signals, because your attention is too tightly managed.
You miss serendipity, because your schedule is too optimized.
You miss depth, because you’re too focused on speed.
And eventually, you miss yourself and the part of you that used to follow threads just because they were interesting.

This section is about refusing that trap.

Because curiosity isn’t a distraction. Leisure isn’t indulgent. And to wander is to disocver.

Hustle Culture Wasn’t Built For Us

Hustle culture is patriarchal. Not just because it rewards brute force and burnout, but because it defines value in strictly extractive terms: How much did you produce? How fast? How visibly? For whose approval?

This mindset turns exploration into waste. It treats rest as weakness. It flattens creativity into content and intuition into “soft skills.”

And it’s particularly punishing for women. Because we’re not just expected to perform at that level, we’re expected to perform it gratefully. As if the privilege of hustling alone should be enough.

So we work harder. Sharper. Longer. We train ourselves out of leisure, because we’re scared we haven’t earned it yet. We train ourselves out of curiosity, because we’re scared of being seen as unserious. We even train ourselves out of reflection, because what if we fall behind?

The result is a generation of ambitious women who are accomplished but exhausted. Focused but disconnected. Competent but creatively malnourished.

Leisure Is Legitimacy

Protecting your right to unstructured time is a radical act of self-authorship.

Because for most of history, leisure was a privilege reserved for people who didn’t have to prove anything. Think about it. Who was allowed to stroll aimlessly? To write poetry in cafés? To attend lectures with no clear purpose? It wasn’t women. And it definitely wasn’t working-class women.

So when you, as an ambitious woman today, claim time for wandering. Time that isn’t optimized or monetized or pre-justified. You’re reclaiming a kind of intellectual and emotional freedom that was historically denied to you.

You’re saying: I don’t have to earn the right to reflect. I don’t have to disguise my interests as productivity. I don’t have to apologize for using my time in ways that stretch beyond the immediate task at hand.

Leisure doesn’t mean doing nothing. It means creating space for nonlinear growth.

The Emotional Labor of Staying Curious

Let’s also acknowledge that it’s harder for some people to stay curious than others.

When your career is precarious, when you’re the only woman in the room, when your background isn’t the default, you have to fight to protect the bandwidth that curiosity requires.

Because curiosity means asking questions that might not land. Reading things that don’t obviously matter. Saying, “I don’t know yet.” And those acts, innocuous as they seem, can feel risky when you’re used to having to prove yourself.

We need to stop treating curiosity as a luxury, and start treating it as a non-negotiable. Not just for creativity, but for equity. Because when more women, especially women from underrepresented backgrounds, have the freedom to follow ideas that aren’t pre-approved by the status quo, we all get smarter. And we all get luckier.

Your Job Is Not to Look Busy

You don’t need to blow up your calendar to reclaim curiosity. But you do need to make space. For questions that don’t have answers yet. For experiments that might flop. For signals that don’t fit the brief.

You need to follow the thread that feels slightly off-topic because that’s often where the real insight lives. You need to let your mind wander without guilt because that’s where new connections form. You need to defend your weirdness, not as a branding gimmick, but as an engine of differentiation.

You don’t win by being the most efficient. You win by being the most perceptive. And you can’t be perceptive if you never give yourself time to perceive.

So take the walk. Read the novel. Write the draft. Book the hour that’s just for thinking. Not because it looks good, but because it works.

In a system that wants you optimized and obedient, choosing curiosity is resistance. Choosing leisure is rebellion. Choosing to see is what makes you impossible to ignore.

VII. Train It: Your Serendipity Practice

This is not a morning routine. This isn’t a 10-step checklist or a template to become a better internet person. You’re not optimizing for output. No immediate results to look forward to.

You’re building the conditions for luck to land.

Because the people who look “naturally lucky” are often just better at exposing themselves to the right kinds of motion, the right variety of signals, and the right small experiments that compound over time.

You don’t have to change who you are. You just have to move differently. Here’s how.

Daily: Two New Inputs

Start small. Every day, introduce two new inputs into your world. One intellectual, one relational.

The intellectual one could be anything: an article from a field you don’t work in. A podcast with someone outside your bubble. A weird data point, a design you don’t fully understand, a long-read you skim instead of doomscrolling. It’s about texture. (If you want help with this, check out my Things I Read This Week series on Instagram and Substack!)

The relational one: DM someone. Comment with intention. Compliment a stranger’s thinking. No angle. No pitch. Just a genuine nudge that says, “I’m paying attention.”

You never know who replies. You never know which article plants a seed. But after 30 days, you’ll have sixty new reference points, and that’s when momentum builds and things start clicking.

Weekly: Pattern Pages

Luck loves pattern recognition. And pattern recognition requires retention. So start writing things down.

I have a document I’ve been running almost 10 years now, where I add any wayward idea I have. It’s huge, half of it is nonsense, and all of it is precious to me. I firmly believe that you should never delete any idea, because there are no bad ideas. Just bad timing and wrong person.

Start yours today. Google Doc, Notion page, your personal WhatsApp chat, doesn’t matter.

Every week, add 3 bullet points. No pressure to explain them. Just jot the signals you’re noticing:

• Everyone’s asking for the same feature, but calling it something different

• This price point keeps showing up in completely unrelated industries

• Three founders in a row mentioned the same book/tool/frustration

If something shows up three times, you test it. That’s the rule.

You don’t need to chase every one. But when something repeats, your job is to ask why, and to question whether it’s a coincidence or a crack opening.

Over time, this becomes your personal database of hunches. And hunches, tracked well, become theses.

Biweekly: Serendipity Hours

Every two weeks, block 60–90 minutes for structured wandering. No laptops, no emails, no immediate outcomes.

You might attend a niche meetup. Walk a neighborhood you don’t live in. Visit a shop that’s clearly not “for you.” Eavesdrop with permission. Sit with another team. Explore a Slack group that’s outside your role.

Your only deliverable is to come back with one “I didn’t know that.”

That’s it.

You’re not producing insight. You’re increasing surface area. You’re giving your brain room to make lateral connections. Most people never schedule that. And most people never stumble into the opportunity that changes everything.

Monthly: Small Bet Sprint

Once a month, run a three-day sprint of tiny experiments. These aren’t full launches. These are low-stakes probes to surface signal:

• Test a new copy angle

• Run an alternate onboarding

• Reach out with an absurdly specific ask

• Create a tiny landing page and send it to five people

• Co-work with someone in an unrelated industry

The point is to make movement visible. Not to scale. Not to succeed. To see what wants to move. To create moments for luck to intervene.

Each experiment should take under four hours. If it fails, great. If it sparks, you know where to look next.

Quarterly: Pull a Thread

Once every quarter, go deep on one weak signal. This is your mini-research sprint.

Pick something from your Pattern Pages that’s been calling to you. Doesn’t need to be trending. Just persistent.

Now pull.

Interview five people. Read the last twenty articles on it. Talk to someone working adjacent. Build a sketch. Test a prototype. Map the ecosystem.

You’re not looking to validate. You’re looking to expand your map. To understand how this signal fits into a broader pattern, and what opportunities it might hold if you’re early enough to act.

This is how good bets start. Not from decks. From threads that didn’t let go.

Bonus: The Three-Signal Rule

A simple heuristic for attention: when something appears three times from different sources in one cycle (a week, a month, a quarter), it’s worth slowing down for.

Doesn’t matter if it feels random. If the pattern shows up again and again, your job isn’t to dismiss it. Your job is to get curious.

It might lead nowhere. But it also might be your next pivot. Your next hire. Your next story worth telling.

And your ability to spot that moment faster than most? That’s what turns chance into advantage.

Do Not Use This As A Checklist

You don’t have to be perfect with any of this. You don’t have to do it all the time. But the more regularly you make space for new inputs, for lateral motion, for curiosity without shame, the more your life becomes structured around serendipity.

When that becomes your norm, luck stops feeling random.

You stop waiting to be discovered. You stop clinging to the big break. You start noticing how many small doors were cracked open already, and how you just needed to walk through them.

Training your luck doesn’t make the world fairer. But it does make you braver. Sharper. Faster at reading signal. More willing to act when something flickers.

That’s how you build a career and a life that doesn’t rely on being chosen.

VIII. You Don’t Chase Luck. You Build a Life It Can Enter

By now, you’ve probably guessed the truth: luck isn’t something you wait for. It’s something you steadily prepare for in how you think, what you notice, who you talk to, and how you move through the world.

And when you look closely at the people who seem to always be in the right place at the right time, you’ll see the pattern: they’ve built more doors. More surface area. More practices that expose them to the unexpected, and sharpen their ability to recognize it when it shows up.

They’re not chasing luck. They’re building a life it can enter.

This is what we’ve talked through:

• That attention is a skill, and you can train it.

• That motion matters, not just forward, but across.

• That curiosity isn’t indulgent.

• That weak signals, small bets, and strange collisions are where the best ideas hide.

• That flânerie isn’t wasting time. It’s how you stay ready.

• And that for women especially, reclaiming time to explore is an act of deep political reverence.

None of this guarantees success. But it does change your relationship to uncertainty.

You start seeing rejection not as a verdict, but as information.
You start following detours not with panic, but with intent.
You stop trying to be everywhere, and instead, focus on being deeply present in the few places where your instincts pull you.

And over time, those instincts sharpen.
You notice faster. You respond quicker. You pivot earlier.
You stop waiting to be chosen and start choosing what to pursue, what to drop, and what to make room for.

That’s what trained serendipity really gives you: not a guarantee, but a growing sense that you know how to move when the next strange little opportunity shows up.

And it will. Because they always do.
You just have to be someone who sees it.

So no, don’t ask how to get lucky. Ask how to get ready.

Build your attention. Expand your map. Stay in motion. Make your bets.

And when the moment arrives (and it will) you won’t be surprised. You’ll be prepared.