Creating Serendipity: How to Make Luck Work for You
Frank Choy
Outsourced CFO | Mgt Consultant | Business Adviser @ Capstone Consulting | Manufacturing Process Improvement
Introduction
Some moments change everything. A chance conversation sparks a career shift. A random encounter leads to a lifelong relationship. A simple idea, thrown into the right discussion, turns into a business opportunity.
We often look at these moments and call them luck - as if they’re completely out of our hands. But are they?
Serendipity isn’t just about being in the right place at the right time. It’s about being the kind of person who turns chance into opportunity. It’s about how we think, how we engage with the world, and how we respond to the unexpected.
Some people seem to attract opportunities effortlessly, while others feel stuck, waiting for a “big break.” The difference? Serendipity is a skill, not a coincidence.
This article explores:
?? Why some people seem luckier than others.
?? The psychology behind spotting and acting on opportunities.
?? How small actions increase the chances of life-changing moments.
If you want more unexpected wins, meaningful connections, and game-changing insights, serendipity is something you can cultivate on purpose. Here’s how.
The Science of Serendipity: Is It Really Random?
We often think of luck as something entirely out of our hands - some people just happen to be in the right place at the right time. But if that were true, how do we explain the fact that some individuals seem to consistently encounter great opportunities while others don’t?
The truth is, serendipity isn’t random - it’s shaped by how we perceive, process, and act on the world around us.
Science suggests that what we call “luck” is actually a set of cognitive habits and behavioural patterns that either invite or block unexpected opportunities.
Let’s break it down.
1?? How Our Brains Shape Serendipity
Serendipity doesn’t just happen - it’s recognised by the brain. If we’re not primed to notice it, we’ll walk past a million opportunities without ever realizing they were there.
Selective Attention & the “Invisible Gorilla” Experiment
Psychologists Christopher Chabris and Daniel Simons conducted a now-famous experiment where participants watched a video of people passing a basketball and were asked to count the passes.
Halfway through the video, a person in a gorilla suit walked into the scene, paused, beat their chest, and walked off.
Amazingly, over 50% of participants didn’t notice the gorilla.
What does this tell us? Our brains only notice what they’re conditioned to look for.
?? Implication for Serendipity:
Try this: Next time you're at an event, deliberately widen your focus. Instead of looking only for what you expect (e.g., networking for clients), observe the environment, people, and side conversations. Serendipity often comes from unexpected connections.
2?? The Role of Pattern Recognition
The brain is constantly scanning the world, looking for patterns - connections between what we already know and new information we receive.
David Bowie & the Unexpected Genius of Mashups
David Bowie’s unique sound wasn’t just raw talent - it came from his ability to connect disparate influences. He merged jazz, classical, rock, and even electronic music, creating something entirely new.
Neuroscientists call this “conceptual blending” - the ability to take unrelated ideas and merge them into something novel.
?? Implication for Serendipity:
Try this: Make a habit of cross-pollination - read outside your field, attend industry events unrelated to your work, or learn a skill completely different from your expertise. These “unrelated” experiences expand your brain’s ability to see connections others miss.
3?? Action Bias: Why Some People Act on Serendipity & Others Don’t
Serendipity is not just about seeing opportunities - it’s about acting on them.
Many people experience lucky breaks but fail to act, either due to hesitation, fear of looking foolish, or overanalysing.
Jeff Bezos & the Regret-Minimization Framework
When Jeff Bezos was debating whether to leave his Wall Street job to start Amazon, he asked himself:
“When I’m 80, will I regret having tried and failed? Or will I regret not trying at all?”
This simple shift in perspective allowed him to act decisively on an uncertain but promising opportunity.
?? Implication for Serendipity:
Try this: Next time an opportunity presents itself, take action before you feel ready. Even a small step - sending an email, starting a conversation, or sketching an idea - can transform a potential moment into something real.
Key Takeaways from the Science of Serendipity
1?? Train your brain to notice opportunities – Widen your attention to unexpected connections.
2?? Expand your experiences – More diverse inputs = more “dots” your brain can connect.
3?? Act before you feel ready – Serendipity favours those who move, not just those who think.
The Mindset Shift: From Linear Success to Circular Growth
We’re conditioned to believe that success follows a straight line:
? Set a goal. ? Make a plan. ? Execute.
The traditional model assumes that if we just follow the steps, we’ll get to the outcome. But life rarely works that way. A very simple example - boiling different eggs is likely to produce different results - due to variability in eggs, water temperature, etc.
Serendipity thrives in uncertainty, adaptability, and non-linearity. The most successful people don’t just chase goals - they position themselves for unexpected opportunities.
Let’s explore why shifting from linear thinking to circular growth is key to making luck work for you.
1?? The Illusion of Predictability: Why Fixed Goals Can Limit You
Traditional goal-setting assumes we can predict the future. But most of the biggest breakthroughs happen by accident—not by rigid planning.
The Post-it Note: A Failed Experiment Turned Success In 1968, Spencer Silver, a scientist at 3M, was trying to develop a strong adhesive. Instead, he accidentally created a weak, reusable adhesive that barely stuck to surfaces.
For years, it was considered useless - until one of his colleagues realised it could be used for temporary notes that could be repositioned.
?? Takeaway: If Silver had only focused on his original goal (a strong adhesive), he might have dismissed his discovery entirely. Instead, he remained open to reinterpretation, which led to one of the most successful office products ever created.
Serendipity Happens When You Leave Room for New Possibilities
Many people lock themselves into rigid career paths, business strategies, or life plans. When something unexpected happens, they reject it rather than explore it.
But serendipity often looks like failure before it looks like success.
Try this: Instead of asking, "How can I achieve this exact goal?" ask:
? "What is emerging in my life that I hadn’t planned for?"
? "What opportunities am I dismissing because they don’t fit my plan?"
2?? Circular Growth: How Great Thinkers Use Feedback Loops
Linear thinkers assume success is about executing a plan. Circular thinkers understand that success is about continuous adaptation.
Steve Jobs: The Intersection of Calligraphy & Computing
After dropping out of college, Steve Jobs randomly took a calligraphy class. At the time, it had no career relevance.
Years later, when designing the Macintosh, he remembered what he learned and insisted on beautiful typography for computers.
?? Takeaway:
How Circular Growth Works
1?? Expose yourself to diverse experiences.
2?? Reflect on how they might connect in unexpected ways.
3?? Act on emerging patterns, even when they don’t fit a pre-planned outcome.
Try this:
? Take a class or explore a skill unrelated to your main work.
? Read outside your field.
? Join conversations outside your usual industry.
The more inputs you have, the more serendipitous connections your brain can make.
3?? The Pivot Mindset: Why Agility Beats Certainty
Netflix: A DVD Company That Became a Streaming Giant Netflix started as a DVD rental-by-mail business. If they had stuck to their original vision, they would have gone extinct with Blockbuster.
Instead, they saw emerging digital trends, pivoted into streaming, and later original content.
?? Takeaway:
Try this: Instead of asking, "Am I on the right path?" ask:
? "What is my environment telling me?"
? "Where is unexpected momentum already forming?"
Key Takeaways from The Mindset Shift
1?? Rigid goals can blind you to better opportunities.
2?? Circular growth beats linear planning - expose yourself to more inputs.
3?? The most successful people pivot when serendipity presents new paths.
Experimentation: Tiny Steps, Big Breakthroughs
Serendipity doesn’t happen when you sit and wait - it happens when you step into the world, try things, and see what unfolds.
Many people think that luck is about waiting for the perfect opportunity, but in reality, it’s about increasing your surface area for lucky breaks by taking action.
This is where tiny experiments come in. Small, low-risk actions can lead to unexpected opportunities, new relationships, and game-changing insights.
1?? Why Experimentation is the Engine of Serendipity
?? Anne-Laure Le Cunff (Tiny Experiments) argues that small experiments help us break free from rigid thinking:
"When we experiment, we let go of needing to be ‘right’ and instead focus on discovery."
Unlike big, high-stakes decisions, tiny experiments remove fear and hesitation. They allow you to:
?Test new ideas without risk
? Explore different social and professional spaces
? Discover unexpected passions and skills
2?? “Giving to the Universe” – The Role of In-Person Events & Networking
Serendipity isn’t just about what you get - it’s also about what you give.
One of the best ways to create unexpected opportunities is by actively engaging with people and offering value without expecting anything in return.
A Personal Example:
Years ago, I joined a social group that met for Friday drinks, theatre nights, and weekends away. I had no specific agenda - just a desire to enjoy interesting company at a time I was very busy with my career.
One night, I went to the theatre with friends to see a play. And that’s where I met my future wife. Had I been searching for a relationship, I might have approached the group differently, perhaps putting pressure on interactions. But instead, I was just participating fully, giving my presence to the group, and allowing things to unfold.
?? The Lesson:
Try This:
? Attend an in-person event without an agenda - just engage and be present. It's great practising social skills.
? Give without expectation - offer help, ideas, or encouragement freely.
? Follow your curiosity - let conversations lead you somewhere unexpected. Be interested.
3?? Australian Examples of Experimentation
Canva: A Startup Born from an Unexpected Teaching Gig
Melanie Perkins, the co-founder of Canva, never set out to build a multi-billion-dollar company.
She was a university student in Perth, tutoring classmates on how to use graphic design software. She noticed that many people struggled with existing tools, which sparked an idea:
"What if graphic design could be made simpler?"
That small teaching experiment planted the seed for Canva. Years later, after multiple tiny iterations and pivots, Canva became a global success story.
?? The Takeaway:
Try This:
? Share your skills in a low-stakes setting - volunteer, tutor, or offer free workshops.
? Test an idea in a small way - before committing to a full-scale business.
4?? The Power of Showing Up: Why Serendipity Needs Action
Many people stay in their comfort zones, waiting for the “right moment” to try something new. But serendipity only happens when you engage with the world.
?? The “Barbecue Effect” – How Unexpected Social Interactions Lead to Luck
In Australia, we often hear stories about people landing jobs, finding investors, or meeting future business partners over a barbecue.
Unlike formal networking, where everyone has an agenda, casual settings create space for natural, unforced conversations.
Many life-changing opportunities have started with:
? A chat at a community event
? A casual introduction by a mutual friend
? A random conversation at a conference
?? The Takeaway:
Try This:
? Attend one live event per month, just to see what happens.
? Go to a different kind of gathering than usual (a tech event, an art show, a volunteer meet-up). Do follow up coffees with new connections.
? Strike up a random conversation with someone new - you never know where it might lead.
?? Key Takeaways from Experimentation & Serendipity
1?? Tiny actions create unexpected connections and opportunities.
2?? Giving to the universe - without expectation - brings serendipitous rewards.
3?? Live, in-person engagement beats passive waiting for opportunities.
4?? The more you step into the world, the more luck you create.
Overcoming Hurdles to Serendipity
Serendipity isn’t just about creating or spotting opportunities - it’s about being able to act on them.
Even if you have the right mindset, fear, hesitation, and self-doubt can hold you back. And even if you’re ready to take action, your environment, industry, or network may limit your exposure to the right opportunities.
To fully cultivate serendipity, you need to overcome both internal and external hurdles.
1?? Internal Hurdles: Fear, Self-Doubt & Perfectionism
Even in the most opportunity-rich environments, many people block their own luck due to psychological barriers:
?? Fear of failure – Worrying about looking foolish or making mistakes.
?? Imposter syndrome – Feeling like you’re not “ready” or don’t belong.
?? Perfectionism – Waiting for the perfect conditions before acting.
?? Overthinking – Analysing instead of doing.
Fear of Failure: The Paralysis That Stops Serendipity
Dr. Carol Dweck (Mindset) found that:
"People with a fixed mindset avoid challenges, while those with a growth mindset see failure as learning."
?? How to Overcome It:
? Reframe failure – Every mistake is data. If you fail, you’ve learned something valuable.
? Detach self-worth from outcomes – What you try isn’t who you are.
? Use the “L-Plates” mindset – Like a learner driver, you’re supposed to be imperfect.
Try This:
Imposter Syndrome: Feeling Like You Don’t Deserve the Opportunity
Dr. Valerie Young (The Secret Thoughts of Successful Women) found that even high-achievers doubt themselves.
Many people hold back because they think:
? “I’m not qualified to be in this room.”
? “I don’t know enough yet.”
? “What if people realise I don’t belong?”
?? How to Overcome It:
? Shift the focus – Instead of "Am I good enough?" ask "How can I contribute?"
? Use the 70% Rule – If you’re 70% ready, take the opportunity.
Try This:
Perfectionism: The Enemy of Action
Reid Hoffman (LinkedIn founder) said:
“If you’re not embarrassed by the first version of your product, you’ve launched too late.”
?? How to Overcome It:
? Launch before you’re ready – Progress is better than perfection.
? Break things into tiny experiments – Start small and iterate.
Try This:
2?? External Hurdles: Positioning Yourself for Serendipity
Even if you’re mentally prepared, your environment affects your ability to create luck.
Some people work in industries or social circles that limit serendipity:
?? Risk-averse workplaces – Where failure is punished, not rewarded.
?? Closed networks – Where opportunity is based on “who you know.”
?? Geographic limitations – If you’re not in an innovation hub, luck may be harder to come by.
The Power of Changing Your Environment
Personal Example: Moving from NZ to Australia After my marriage breakup, I felt stuck in a rut in New Zealand. I needed a fresh start, so I moved to Australia, where my siblings lived.
?? What Happened?
Lesson: Sometimes, a physical move or a change in routine is needed to break free from stagnation.
Try This:
Expanding Your Network & Finding the Right People
Sociologist Mark Granovetter’s study on The Strength of Weak Ties found that:
“Life-changing opportunities are more likely to come from acquaintances than close friends.”
Close friends tend to move in the same circles, but weak ties introduce us to fresh opportunities.
?? How to Use This to Your Advantage:
? Attend industry events and networking sessions.
? Say yes to unexpected invites.
? Engage in communities beyond your immediate industry. A great place is a voluntary group.
Try This:
Final Thoughts: The Balance Between Internal & External Factors
1?? Overcome internal hurdles – Fear, perfectionism, and imposter syndrome block action.
2?? Place yourself in high-opportunity environments – More exposure = more chance encounters.
3?? Expand your network beyond close friends – Weak ties open doors you didn’t know existed.
Building a Serendipity Framework: A Step-by-Step Approach
Serendipity might feel like something that just “happens”, but in reality, it can be designed and cultivated.
By being intentional about how you position yourself, the actions you take, and the mindset you adopt, you can increase your chances of experiencing unexpected opportunities.
This section provides a structured framework for making serendipity a habit, rather than just a lucky accident.
1?? The Three Pillars of Serendipity
To cultivate more serendipity in your life, you need to optimise three key areas:
1. Mindset – Thinking in a Way That Attracts Serendipity
?? Mindset Shift: Instead of asking "What’s the safest way to get from A to B?" ask:
? “Where might this unexpected situation lead me?”
? “What patterns or themes keep emerging in my life?”
?? 2. Behaviour – Taking Actions That Invite Chance Encounters
?? Try This:
? Go to an event without an agenda - simply to engage and observe.
? Strike up a conversation with someone outside your usual circle.
?? 3. Systems – Structuring Your Life for More Serendipitous Moments
Serendipity doesn’t happen in chaos - it happens when you consistently create conditions for it to emerge.
?? How to Build a Serendipity System:
? Set serendipity rituals - regularly expose yourself to new people, ideas, and places.
? Keep an ideas journal - write down patterns, insights, and recurring themes.
? Follow up on weak connections - send a message, suggest a coffee, reconnect.
Try This:
2?? The “Serendipity Ladder” – A Practical Framework
?? Think of serendipity as a ladder - each step increases your surface area for lucky moments. It's about a journey of many roads taken.
Step 1: Expand Your Inputs (Expose Yourself to More “Dots”)
? Read outside your field.
? Follow curiosity, not just goals.
? Surround yourself with people from diverse backgrounds.
Step 2: Improve Your Pattern Recognition (Notice the Dots)
? Keep a serendipity journal - write down recurring themes in conversations, ideas, and events.
? Ask yourself, “Where have I seen this before?”
Step 3: Increase Your Action Bias (Connect the Dots)
? Share your ideas publicly - even if they’re unfinished.
? Take micro-actions before you feel ready.
? Follow up on gut instincts - email that person, explore that idea.
Step 4: Place Yourself in High-Luck Environments (Step Into the Right Rooms)
? Attend live events and social gatherings where random conversations can happen. AA great place is WEA Sydney - a great place for night classes for all sorts of subjects.
? Say yes to unexpected invitations.
3?? Making Serendipity a Lifestyle, Not an Accident
Serendipity isn’t something you can force, but it is something you can cultivate.
? The more exposure you have, the more dots you collect.
? The more patterns you notice, the more insights emerge.
? The more actions you take, the more doors open.
?? Final Challenge:
Conclusion: Serendipity is a Skill - Not Just Luck
Serendipity is often mistaken for luck - something that just happens to certain people. But as we’ve explored, it’s not random. It’s a skill, a mindset, and a habit.
The people who experience the most serendipitous moments are not simply lucky. They are: ? Curious enough to explore beyond their comfort zone.
? Open enough to notice patterns and unexpected connections.
? Bold enough to act before they feel completely ready.
Serendipity isn’t about forcing things to happen - it’s about positioning yourself so that lucky breaks become more likely.
?? The Serendipity Challenge: What Will You Do Next?
Creating more luck in your life doesn’t require a massive leap - just small, consistent steps.
Ask yourself:
? What’s one tiny experiment I can try this week?
? Where can I place myself in a new environment this month?
? Who can I connect with, just to see what happens?
Final Thought:
Most of the best things in life - career breakthroughs, lifelong friendships, unexpected opportunities - don’t come from following a rigid plan. They come from staying open, taking small actions, and trusting the process.
Serendipity is always waiting. The question is: Will you step into it?
All the best!
Frank Choy
16 March 2025
Recommended reading
1?? The Serendipity Mindset – Dr. Christian Busch How to increase lucky breaks by shifting your perspective and taking small actions that lead to big opportunities.
2?? The Luck Factor – Dr. Richard Wiseman Psychological research on why some people are “luckier” than others - and how you can develop the same traits.
3?? Tiny Experiments – Anne-Laure Le Cunff The power of small, low-risk actions in creating breakthroughs, new opportunities, and unexpected insights.
4?? What I Wish I Knew When I Was 20 – Dr. Tina Seelig How to take unconventional paths, break free from linear thinking, and embrace serendipity in career and life decisions.
5?? Mindset – Dr. Carol Dweck Why a growth mindset leads to more serendipitous moments - and how to train your brain to embrace challenges instead of fearing failure.
?? Bonus Read: The Strength of Weak Ties – Mark Granovetter (Research Paper) - A fascinating study on how unexpected connections (weak ties) open more doors than close-knit circles.
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