The Serendipity Playbook: How to Get Luckier on Purpose
By Joel Comm | A Trusted Voice in a Noisy Tech World
# The Serendipity Playbook: How to Get Luckier on Purpose
I used to think luck was random. You either had it or you didn’t. Some people were born under a lucky star, and the rest of us just had to work harder.
Then I started paying attention to the “lucky” people in my life. The entrepreneurs who stumbled into million-dollar ideas. The authors who met their agents at coffee shops. The investors who got into hot deals through random introductions.
Here’s what I discovered: These people weren’t actually luckier. They were creating conditions for luck to happen.
I call this serendipity. It’s one of the three dimensions of my Fun Formula, and it might be the most misunderstood success factor in business and life.
The Myth of Random Luck
Most people treat serendipity like winning the lottery. They think it’s completely outside their control. But after studying this for years, and experiencing it firsthand, I know that’s wrong.
Serendipity isn’t random. It’s the result of specific behaviors and decisions that increase your surface area for good things to happen.
Think about it mathematically. If you stay in your office, talk to the same five people every day, and follow the same routine, how many opportunities for surprise connections exist? Almost zero.
But if you say yes to invitations, start conversations with strangers, and put yourself in new environments, you’ve exponentially increased the chances that something unexpected and beneficial will occur.
I learned this lesson the hard way early in my career, and it changed everything.
My Serendipity Stories
In 2003, I almost skipped a breakout session at a marketing conference in Chicago. I was tired, the session topic seemed irrelevant to my business, and I wanted to grab coffee instead.
But something made me walk into that room. Maybe it was boredom. Maybe it was the free donuts.
The speaker was talking about email marketing strategies I’d never heard of. During the break, I introduced myself to the guy sitting next to me. Turns out he was building a software company that perfectly complemented what I was doing.
That random conversation became a business partnership that generated seven figures in revenue over the next three years. All because I didn’t skip a session I almost avoided.
Here’s another one. In 2015, I was invited to be a guest on a podcast I’d never heard of. The topic was artificial intelligence, which wasn’t really my area of expertise. My instinct was to decline.
But I said yes anyway. During that conversation, the host mentioned he was looking for advisors for a new venture. That casual comment led to my early investment in what became one of the hottest AI companies of the decade.
These weren’t lucky breaks. They were the predictable result of putting myself in situations where serendipity could happen.
The Strategy of Saying Yes
I have a rule now: I say yes to invitations that have no obvious payoff at least once a week. This goes against every productivity expert’s advice about protecting your time and focus.
But here’s what those experts miss. The most valuable opportunities often come disguised as wastes of time.
That random industry meetup. The conference outside your field. The coffee with someone who does something completely different from what you do. These look inefficient on your calendar, but they’re actually investments in serendipity.
I’m not talking about saying yes to everything. That’s a recipe for burnout. I’m talking about being strategic about which “wastes of time” you choose.
The key is looking for environments where interesting people gather to discuss ideas outside your normal sphere.
Where Serendipity Lives (And Dies)
Serendipity happens in specific environments. It thrives in places where people from different worlds collide. Mixed conferences. Cross-industry events. Informal gatherings where the agenda is loose.
It dies in homogeneous environments where everyone thinks the same way and talks about the same things.
This is why I’m worried about what remote work and heads-down culture are doing to serendipity. When everyone works from home and only connects through scheduled Zoom calls, we lose those random hallway conversations that used to spark innovation.
We’re optimizing for efficiency and killing serendipity in the process.
I’m not against remote work. I’ve been doing it since before it was cool. But I am concerned about creating sterile environments where unexpected connections can’t happen.
The companies and individuals who figure out how to recreate serendipity in a remote world will have a massive advantage.
My Five Serendipity Practices
After years of studying and experiencing serendipity, I’ve developed five specific practices that consistently increase my luck surface area.
1. The One Uncomfortable Yes Per Week Rule
Every week, I say yes to something that makes me slightly uncomfortable or seems like it might be a waste of time. A conference outside my industry. A dinner with people I don’t know well. A conversation about a topic I know nothing about.
This forces me out of my comfort zone and into situations where serendipity can happen.
2. Going to Events Outside My Industry
I attend at least one event per quarter that has nothing to do with my primary business. Art exhibitions. Science conferences. Local meetups for hobbies I’m curious about.
The best insights often come from connecting ideas across different fields. Plus, you meet people who can introduce you to entirely new worlds.
3. Starting Conversations with People Unlike Me
At events, I actively seek out people who are obviously different from me. Different industries, different backgrounds, different perspectives.
These conversations are often awkward at first, but they’re also where the most interesting ideas emerge. Homogeneous conversations rarely produce surprises.
4. Sharing Work in Progress Publicly
I regularly share ideas, projects, and thoughts before they’re fully formed. This feels vulnerable, but it creates opportunities for people to connect with me about possibilities I hadn’t considered.
Some of my best collaborations started with someone reaching out after seeing something I posted that was rough around the edges.
5. Following Curiosity Threads Without Obvious Destinations
When something sparks my curiosity, I follow it even when I can’t see how it connects to my goals. I read articles about random topics. I reach out to people doing interesting work in fields I don’t understand.
These curiosity threads often weave together in unexpected ways months or years later.
The Remote Work Problem
Here’s what worries me about the direction we’re heading. The productivity culture says we should eliminate distractions, batch similar tasks, and optimize every moment for efficiency.
But serendipity is inherently inefficient. It requires slack time, random encounters, and conversations that don’t have obvious business purposes.
Remote work makes this worse. When all our interactions are scheduled and purposeful, we lose the serendipity that used to happen in office hallways, coffee shops, and random encounters.
The companies that figure out how to recreate these conditions remotely will win. The ones that don’t will slowly become less innovative and more insular.
Why Serendipity Will Define the Next Decade
I believe the best career opportunities of the next decade will come from serendipity, not strategy. Here’s why.
The world is changing so fast that five-year plans are almost meaningless. The industries that will matter most in 2030 barely exist today. The skills that will be most valuable are still being invented.
In this environment, rigid career strategies become liabilities. The people who thrive will be those who stay open to unexpected opportunities and can adapt quickly when serendipity strikes.
This is especially true in technology and entrepreneurship, where breakthrough innovations often come from connecting ideas across different domains.
The AI revolution didn’t come from AI researchers alone. It came from the intersection of computer science, neuroscience, mathematics, and philosophy. The people who were positioned at those intersections were the ones who seized the biggest opportunities.
Connecting to The Fun Formula
Serendipity is one of three dimensions in my Fun Formula framework, alongside Curiosity and Risk-Taking. These three elements work together to create a life and career that’s both successful and enjoyable.
Curiosity drives you to explore new ideas and meet new people. Risk-Taking gives you the courage to act on opportunities when they appear. Serendipity is what happens when you combine curiosity and risk-taking with openness to unexpected possibilities.
Without curiosity, you won’t expose yourself to new ideas that could spark serendipitous connections. Without risk-taking, you won’t have the courage to pursue opportunities that seem uncertain. Without serendipity, you’ll miss the breakthrough moments that define great careers.
Most people focus on working harder within their existing framework. But the biggest opportunities come from stepping outside that framework entirely and letting serendipity guide you toward possibilities you never imagined.
Your Serendipity Challenge
Here’s my challenge for you. This week, say yes to one invitation that seems like it might be a waste of time. Go to that random meetup. Accept that coffee invitation from someone you barely know. Attend that conference session outside your expertise.
Pay attention to what happens. Not just the immediate outcomes, but the second and third-order effects that might unfold over the coming months.
Start building your serendipity muscle. The more you exercise it, the stronger it gets. And the stronger it gets, the luckier you’ll become.
The opportunities of the next decade won’t come from following the conventional playbook. They’ll come from being in the right place at the right time, with the right mindset to recognize and seize unexpected possibilities.
That’s not luck. That’s serendipity by design.
Ready to discover where you stand on all three dimensions of The Fun Formula? Take the Fun Formula Audit at /fun-formula-speaker/ and get your personalized roadmap for creating more curiosity, risk-taking, and serendipity in your life and career.
Ready to Bring The Fun Formula to Your Stage?
Your audience will leave with a personal score, specific actions, and a framework they can use immediately.
Book Joel for Your Event →AI Made Simple for Your Organization. Six plain-language principles every leader needs right now. No tech lingo. No hype. Just what actually works.
