Planned serendipity

I always thought that the more successful you got in business, the more rational, logical, and measured you would be. Instead, I've had a journey into chaos.

Hi,

I always thought that the more successful you became in business, the more rational, logical, and measured you would be, but I’ve had a different journey. I started in business very “business-minded”.

I put quotes around business-minded because while there is a perception of what being business-minded means, my journey has been a descent into chaos. Traditionally, being business-minded entails possessing a mindset focused on business-related activities, including entrepreneurship, management, finance, and strategic planning. Individuals with this mindset demonstrate strategic thinking, analyzing situations to identify opportunities and developing plans to achieve business goals while also being willing to take calculated risks.

That’s not to say my successful friends don’t have all those qualities. They do. It just paints a picture of a stodgy old man who sits around a computer studying spreadsheets.

Basically, it brings to mind President Business. Meanwhile, most of my successful friends are closer to Princess Unikitty.

Let me be clear: Princess Unikitty is a killer business being. They somehow keep Cloud Cuckoo Land running even though it is pure chaos, and they do it all with an upbeat smile and a heavy dose of magic. On top of that, Cloud Cuckoo Land works effectively-ish, so much so that many master-builders choose to live there. In the chaos, they thrive.

When I first started in business, I thought it was Lawful Evil, like President Business, but I have found business is more Chaotic Good, like Princess Unikitty. Can you explain why Cloud Cuckoo Land works? No, but it certainly does work…until order is imposed on it.

To succeed, it’s usually better for both your company and your mental health to focus chaos productively than to impose order onto it.

After that article, people asked me what they could even do if the world were pure chaos energy. I’ve been thinking about this a lot recently and I think my business started growing when I embraced that chaos and found ways to embrace it in more productive ways.

Mostly, I have fully embraced a concept I’ve been talking about called “planned serendipity”.

It’s not new. There are articles about it dating back over a decade.

Planned serendipity involves creating environments and processes that encourage unexpected discoveries and insights. Here are some main concepts it offers for putting planned serendipity to work in a business:

• Diverse environments—Encourage diverse perspectives and experiences within your team. This diversity can lead to different ways of thinking and increase the likelihood of serendipitous connections.

• Cross-functional collaboration—Foster collaboration across different departments or teams. This can help break down silos and encourage the exchange of ideas that may lead to unexpected insights.

• Flexible workspaces—Create flexible workspaces that allow for chance encounters and spontaneous interactions. This could include open office layouts, casual meeting spaces, or even virtual collaboration tools.

• Encouraging curiosity—Encourage a culture of curiosity where employees are encouraged to explore new ideas and interests. This can lead to unexpected discoveries and insights.

• Serendipity triggers—Identify and create “serendipity triggers” within your organization. These could be events, activities, or tools that are designed to spark unexpected connections or ideas.

• Embracing failure—Create a culture that embraces failure as a learning opportunity. This can help reduce the fear of taking risks and encourage experimentation, which can lead to serendipitous discoveries.

• Learning from serendipity—Encourage employees to reflect on and learn from serendipitous moments. This can help identify patterns or strategies that can be used to foster more serendipity in the future.

By incorporating these concepts into your business practices, you can create an environment that is conducive to serendipity and increase the likelihood of discovering new ideas and opportunities.

The main thing I take away from this is that while you can’t force serendipity, you can bottle it. The more I embrace this business, the faster my success grows. My businesses are mostly about bringing the smartest people I know together, giving them space to exist as their best selves, and understanding that good things happen, even if I don’t know what those things might be, effectively trying to bottle that chaotic good energy to work for everyone at scale.

The more I work building events, the more I believe events fail when they stop being able to bottle that energy for their attendees.

There is an idea in both publishing and movies where if you release enough books, then 1 in 10 books will pay for the other nine. Nobody can tell you which one will succeed, but they know if they release enough projects, then the Bell Curve will stabilize, and they can predict things.

That’s a big, long way to explain that nobody knows what will work, but if we do enough of the right things, it will probably all work out. We all want more certainty than that, but I don’t think it exists. The best we can do is try to bottle chaos without imposing too much order on it.

When I looked into it more, I found that this is true with almost any industry. It’s how venture capital firms work. It’s how mutual funds work. It’s how innovation cycles work.

Basically, our entire economy runs on bottling chaos and planning for serendipity.

We as humans want to believe some people know what they are doing, but the “smartest” people are mostly just really good at bottling chaos and using it to get lucky. After all, luck happens when opportunity meets preparation.

You won’t get your big break before your time. This is an unfortunate truth of being a creative. It doesn’t matter who you know—until you are good enough to create mind-blowing content, nobody is going to hire you.

So many creatives believe that meeting Stan Lee or Steven Spielberg will change their lives. The thing is that it just might. It might change your life, but not until you are ready for it. If you meet Steven Spielberg and hand him your piece of garbage short film, he’s not going to care.

If you meet Steven Spielberg with your earth-shattering movie, he might take notice. He might not, but he might if you catch him on the right day. But that meeting is luck. You have no control over luck. What you have control over is your preparation.

If you prepare properly, opportunities will present themselves. If you put yourself in the right situations, opportunities will happen. If you are prepared, you can make the most of those opportunities. The right opportunities can take years to cultivate, like pulling on a rubber band. As you pull back, the tension grows and grows. The harder you pull on the band, the more force it has when you finally release it.

The trick is to find these opportunities before you are prepared to utilize them and cultivate contacts until they will happily help to advance your career. This is possible even if you are at the beginning of your career and haven’t created anything of import yet.

So, how do we do that?

There’s an old saying among creatives: “Good, nice, and on time. You need two to succeed.” Being good means you have the talent required to do the job. Being nice means people think you are generally pleasant and affable. Being on time means you deliver on or before a deadline.

As the saying goes, you need two to succeed. If you are nice and on time, you don’t have to be that good. If you are good and nice, you don’t have to be on time. If you are good and on time, you don’t have to be that nice. It follows that if you want to find opportunities, you have to master two of those qualities.

At the beginning of your career, you aren’t very good—at least not compared to where you will be in the future (with hard work and dedication, and finished projects). The only two things you have control over are being nice and on time. If you can master those two, opportunities will present themselves if you put yourself in the right situations.

If you can be nice and on time at first, even if you suck at your chosen profession, people will want to be around you. Over the years, you will build a massive Rolodex of influential people who want to work with you. Eventually, with enough practice, you will learn to be really good at your job, too.

Possessing all three of these skills is what I call the holy trinity of success, and it’s critical to build your career. I’ve found it over and over in the top performers of every creative field. If you can start being on time and nice, people will want to help you. If you keep working at your craft, you will eventually get good. If you can be good, nice, and on time, there will be no stopping you.

It’s important to note that when you get your opportunities by being nice and on time, these will be lower-end opportunities. They won’t be hiring you for your dream career; they will be using you for grunt work.

If you can do that work with a smile, you will build up enough trust with people that they will assuredly want to help you at the opportune moment—but don’t ask for that help until you are ready. When you can create great content, it will be a no-brainer for them to work with you.

It’s easy for me to connect the dots of my career in retrospect, but most of it started with getting into the right rooms with the right people.

I recently wrote a comic ​with a very successful author​, but that road started by reconnecting with her in 2022 at 20Books, and it really began in 2015, when we were both running similar companies. My relationship with our publisher goes back years as well, and we’ve both grown our careers in parallel but on dimilar (different but similar) tracks.

My partnership with Monica started in 2020, but it really started years before when I had her on my podcast.

I have maintained this idea for years that if I could know and hang out with enough smart people who were all on dimilar journeys, good things would happen. It wasn’t until I merged it with intention and planned serendipity that it all started to come together.

The planning is the events and the spaces I either join or build with intention. The serendipity is what happens when you get there and let life unfold.

The more I focus on growing the right audience and curating the right events, the more my business grows, and the more I feel like I’m on a solid path.

I don’t know what will happen from just about anything I do. I know that if I put certain projects out into the world, good things will come from them. It might sound terrifying, but it’s one of the most freeing things I’ve ever found.