How to Maximize Serendipity

“The real enemy is the man who tries to mold the human spirit so that it will not dare to spread its wings.” – Abraham Flexner

The best opportunities are the ones you never expected.

They’re serendipitous. 

Serendipity is a state of mind. Serendipity births unexpected opportunities which fuel progress and push us in fruitful directions. By maximizing serendipity, you’ll accelerate your progress. 

Serendipity is a skill, which means it can be learned

Build a Serendipity Vehicle

Writing is the best kind of networking. 

By making it easy for people to find you online, you’ll create a vehicle for serendipity. Call on your vehicle when you want to manufacture serendipity, and you need some activation energy. 

My vehicle is the North Star Podcast. 

Less than three months after starting the North Star Podcast, I was introduced to Neil deGrasse Tyson, arguably the most famous scientist in the world. All I did was ask for a previous podcast guest to introduce me to one of his friends. Turns out, Neil deGrasse Tyson is one of his best friends. 

If you publish content (blogs, podcasts, videos, etc.) regularly, people will discover you and initiate unexpected opportunities. They’ll open doors you didn’t even know existed. 

Maintain a website so people can find your bio, share your work, and describe you in a favorable light. Once your website is live, publish content to encourage people to visit your website, advertise your skills and hype you up.

Relationships built on trust, joy and mutual respect are the foundation of serendipity. 

Be a Connector

I rarely go to conferences or traditional networking events. Doing so feels like a waste of energy, like trying to stand on your tiptoes at a parade. 

In my experience, the best networking happens indirectly. Meet people on the basketball court, in the gym, or at a meal instead of going to a networking event. 

Host intimate events. I host a group in New York called Things We’ve Never Done Before. It’s a collection of passionate, hyper-curious individuals. Every now and then, we meet up for a day of fun, exercise and adventure.¹ 

Open doors for people. 

When you connect other people, tons of value will eventually flow back to you. Introduce your friends to each other. Opportunities are everywhere: Say yes to pick-up basketball, a spontaneous afternoon run, or a trip to the museum.

The healthier you are, the more activities you can attend. 

Prioritize Your Health

People want to be with healthy people. 

Eat healthy food, get enough sleep, and break a sweat every day. It’ll boost your mood and fuel your curiosity. 

People are drawn to people who are energetic and engaged. Healthy people are much more likely to cultivate these traits and enjoy a diverse lifestyle. 

People who sweat together stay together. 

Working out with a friend is social and productive. Turns out, it’s also one of the best ways to spark, maintain, and nurture a relationship. 

Zig and Zag

Do opposites. 

Work on many things at the same time. Surround yourself with eclectic people. Skip the standard destinations and travel to obscure places instead. 

Cross-pollinate ideas from different industries, disciplines, and places. Surround yourself with a diversity of people and develop a variety of skills. The space between ideas will give you a fresh perspective that you can use to problem solve and come up with new ideas. 

Because of your unique set of skills, lucrative deals will flow through you and other people will open doors for you. They’ll sell your abilities and hype you up, leading to serendipitous encounters. 

Avoid Boring People

This advice comes from Jim Watson, who’s famous for co-discovering DNA.

Watson says: “Avoid Boring People.”

On the North Star Podcast, Josh Wolfe said this was the best advice he’s ever received. 

“Avoid Boring People.” Three words, two meanings. The trope is a reminder to (1) stay away from people who aren’t interesting and (2) to be interesting and avoid boring people when you’re speaking with them.

Build conversational momentum by asking questions, staying engaged, and talking about the other person’s interests.²

Whether you’re sitting on an airplane, relaxing in a coffee shop, or walking through a hotel, you’ll be able to speak with anybody, anywhere.

The Hotel Bathroom Principle

Whenever I’m in a city and I need to use the bathroom, I walk into a fancy hotel. 

Fancy hotels always have nice bathrooms. And if you’re dressed well and walk confidently, you won’t be hassled for using the bathroom. 

The world is becoming more casual. But if you dress too casually, it looks sloppy and careless. 

When you want to cultivate serendipity, 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. 

If you remember the “Hotel Bathroom Principle” you’ll always look sharp enough to capitalize on a serendipitous encounter.

Find the Fast Flow

Lucky people move with life, not against it. 

They swim with the current in a wide, ever-expanding river. By doing so, they maximize their surface area of serendipity. 

Lucky people bathe in the reverie of adventure. They surround themselves with people who motivate and inspire them. People who maximize serendipity balance the humility of not knowing where their next big break will come from with the arrogance of knowing that it will come from somewhere.³ 

Move to a city. Pursue dynamic environments.⁴ Talk to people. Speak with passion and enthusiasm. Write online. Be curious. Ask about the other person, and when you do, listen intently.

Ambient Relationships

Ambient music is gentle and repetitive. It’s soothing and generates a sense of calmness. It plays in the background, and when you want to listen to it, all you need to do is shift your attention.

Relationships are like ambient music. Staying in touch with people isn’t about being loud and aggressive. It’s about subtle, regular connection.

Stay top of mind with the people who matter most to you. 

This is why I started a weekly email newsletter. Every Monday, I send out an email with nuggets about what I’m doing, learning, and thinking about. I want to make it easy for people to know how they can help me

Call people on their birthday. When you think of a funny memory with a friend, text your friend about it. If you watch a video they’ll like, forward it to them. 

Reach out to people you haven’t spoken to recently. When you do, try to have a reason for doing so. It’ll make the conversation much more fun. 

Twitter DM is a Superpower

If Facebook connects you with people from your past, Twitter connects you with people in your future. 

Get on Twitter.

It’s an interest-based social network, where geography barely matters. On Twitter, you can meet people you’d never be able to meet in real-life.

Tweet about what interests you. Watch what people engage with and tweet more of it, as long as it helps you earn credibility.

Follow like-minded people. Send generous, thoughtful replies. Tweet so the people you admire most will follow you. 

Once they do, send them a direct message. 

Twitter DMs are a secret superpower. 

Go First

Sometimes, it helps to have a little nudge — some activation energy. 

I’m inspired by a simple mantra: “Go First.”

Talk to your crush. Send that email. Dish a compliment. The upside is limitless; the downside is just a sprinkle of embarrassment. 

For example, I’m ruthless about following up with people.⁵ I set strict reminders for myself and I always follow-through.

Ask for Help

Tell the world what you want. Advertise your goals by painting a picture of your ideal future. 

Every now and then, I send out an update to my entire network. In it, I share highlights, goals, and open up about my challenges. Here’s my most recent personal update.

People love to help other people when the framing is right. 

Paradoxically, big goals are sometimes easier to achieve than small ones. Big goals energize everybody — they’ll energize you and everybody around you. By communicating clear, ambitious goals, you’ll galvanize support and attention.⁶

When you ask for favors, follow these three guidelines: (1) be specific and precise, (2) tell the other person why you’re asking for their help, and (3) after they’ve helped you, follow up with them thank them or provide an update. 

Asking for help is an art, not a science.⁷ 

If you remember one thing, remember this: Make it easy for people to help you. 

Tips and Tricks

Networking events are over-rated: As a general rule, the people you want to meet don’t go to networking events. Instead, I recommend small invite-only gatherings, parties adjacent to prestigious conferences, and casual events like pick-up basketball. 

Don’t “Pick Somebody’s Brain”: Help them instead. Whenever I want to meet somebody, I ask to interview them. Doing so makes the time much more productive for the other person. I did this in as an intern in college and I do it now. 

Note: If you’d like to receive future posts by email, subscribe to my “Monday Musings” newsletter. 


Thanks to Andy McCune, Arjun Balaji, Alex Hardy, Nick Maggiulli, and Conor Witt for conversations that fueled these ideas. 

¹ Here are some ideas for you: host a brunch, invite people over for board games and drinks, or start an interview series. 

² Know enough about enough so you can talk to anybody, from artists to scientists to athletes. This will help you spark up engaging conversations with people you’ve never met before.

³ While writing this post, I ran into a friend at lunch, and now, we’re recording a podcast together. 

⁴ Eugene Wei, a previous North Star podcast guest, has had a hugely successful career. When I asked him what he looks for, he said he looks for a giant wave. Then the gets on it, and trusts that the wave will spit him out somewhere in the right direction. 

⁵ Three quick stories: 

  1. I’ve been writing on Twitter for years. In college, something I wrote was discovered by Jason Stein, the founder of Cycle Media. After reading my tweets, he sent me a direct message and asked me to work for him. That’s how I ended up in New York.

  2. In December 2016, I attended a live recording of the Tim Ferriss Podcast. There, I was blown away by the intelligence and creativity of Adam Robinson, who was being interviewed. I sent him an email, asked him to come on the podcast, and now, he’s a mentor to me.

  3. At a mentor’s birthday party a couple months ago, I spoke briefly with one of his colleagues. I didn’t know it at the time, but he co-founded the world’s largest YouTube Channel and worked with some of the biggest names in the music industry. Even though we only spoke for 5 minutes at the party, I asked for his phone number and scheduled a time for dinner. We ended up spending 10 hours together. I’m lucky to call him a friend now.

⁶ Your request should be broad, but not too broad. Narrow, but not too narrow.

Too broad and somebody won’t know how to help you. Too narrow and you might miss an unexpected opportunity. 

⁷ Every industry has different ways of cultivating serendipity. In fashion, people cultivate serendipity by posting Instagrams in trendy garments. In cryptocurrencies, serendipity emerges through Telegrams and dinner events. This is why serendipity is a mindset. The optimal strategy varies from person to person, depending on their specific circumstances.