Engineering Exponential Moments: How To Recognize & Capitalize On Opportunities To Create A New & Different Future

Remember, you only get ~8 trips to the plate in your career.

Dear Friend, Subscriber, and Category Pirate,

In a previous two-part “mini-book,” How To Have A Legendary Career, we wrote about how you only get ~8 trips to the plate. 

If your career starts at 25, and the average retirement age is 65, and each role (each “swing”) is roughly a 5-year journey, that’s 8 trips to the plate and then you’re done. Whatever you accomplish for yourself in those 8 trips—whether it be playing a meaningful role in a company, building your own, mentoring others, making a meaningful contribution to society, achieving your own definition of financial freedom, etc.—defines the totality of your career. For some people, it’s one swing: the job they got out of college became their job for life (either they got comfortable, fulfilled a dream, or were afraid of the next transition,). For others, it’s 16 trips to the plate or more: new opportunities present themselves and are jumped on with ferocity, and roles are changed every 2.5 years. 

But one aspect of career progression that doesn’t get talked enough about is the importance of both recognizing and capitalizing on exponential, serendipitous moments.

For example, how did Category Pirates start?

  • Pirate Christopher was working on a book called Play Bigger, and through lots of Googling and reading, discovered Pirate Eddie’s work in Harvard Business Review. That’s serendipity.

  • Then, Christopher wanted to start doing some content marketing for his podcast and reached out to a friend (a legendary writer on Quora, Dushka Zapata) for a business writer recommendation. Dushka was friends with Pirate Cole from writing on Quora and made the connection. That’s serendipity.

  • Then, Pirate Christopher saw some other wanna-be publishing a book on category design (filled with inane stupidities), and called up Pirate Eddie to see if he wanted to go to war on a book together—fellow pirates, defending the category. That’s serendipity.

  • Then the two of them asked Pirate Cole if he wanted to join in the fun and be the writer for the project. Pirate Cole said yes, would love to. That’s serendipity.

  • The three of us worked together on the book for almost two years before realizing we weren’t writing one book—we were writing dozens of “mini-books” that each needed their own time in the spotlight. So we pivoted, and at the start of 2021 stopped writing one giant book and started writing weekly “mini-books” as a paid newsletter on Substack. That’s serendipity.

Each of these moments happened by “accident.” 

None of this was planned out from the very beginning. 

There was no big strategy meeting, no grand treasure map we finalized before setting out to sea. We just sailed along, looking for opportunities to continue doing what made each of us happy. And since the three of us had shared values (e.g., radical generosity, abundance vs. scarcity mindset, and a good sense of humor), time, space, and energy in our lives to spare, there was room for serendipity.

And yet, this is not how many of the “Here’s How We Made It Big” books, movies, and podcasts tell their stories. Instead, the narrative arc sounds more like a logical progression. No serendipity, no “happy accidents,” no doubling-down on an idea that, at the time, had more going against it than for it. Instead, it’s “I hustled!” and “I manifested!” and “I grinded!” Success is an outcome of blind hard work more than an unreasonable trust, faith, and belief in the journey. The story you hear far less often is, “I just got lucky”

“Those who have succeeded at anything and don't mention luck are kidding themselves.” —Larry King

Obviously, success in life is some immeasurable combination of hard work and luck. The question is, can we be smart enough to know the difference between the two, and recognize when we hit the lottery (and should probably sell the stock) versus when the universe is conspiring in our favor and it’s time to double down. (For example, recently a crypto investor made headlines for turning an $8,000 investment into the Shiba Inu meme coin into $5.7 billion. Hard work or luck? We’ll let you decide that one.)

If you go back through your own career, you can probably pinpoint a handful of “happy accidents” that, if removed or changed, would completely alter your trajectory as a human being: someone you met randomly one night at a bar, someone who made an introduction to someone else that led to a massive opportunity, etc. 

Here’s a happy accident: one of Pirate Cole’s friends made an unprompted, blind introduction, and that introduction sparked an incredible business partnership and friendship—and three months later started a new business

These “happy accidents” are really serendipitous, exponential moments—and they are always happening, all around us.

The question is, are you looking for them? Are you considering them? What lens are you looking through, and what story about your life are you telling yourself? Are you saying, “Those opportunities aren’t for people like me?” Are you refusing to explore new territories because you’re “too busy,” head down, working away? Are you refusing to consider what life might be like if you were to transition out of where you are and into something new? Or can you see the possible within the improbable, and imagine a world where this small, seemingly insignificant introduction, opportunity, or new piece of information might just be the lever with the power to change your life.

Sara Blakely, the legendary founder of Spanx, talks about this often. 

She credits her idea for Spanx and her massive business success by consciously walking through life constantly asking, “Are you my idea? Are you my idea?”

“When I first thought of the idea... Well, actually let me back up for one second. I actually manifested the idea. Everyone’s always like, ‘How did you take an idea and then start a business?’ Well, it’s, ’How did you even come up with the idea?’ I was in search of my idea. And at the time my life was not great. I was selling fax machines door to door. I was living with my mom. I was like 25 years old. And I remember after a whole entire day of being kicked out of office complexes again all day, sometimes having my business card ripped up in my face, I pulled off the side of the road one day and I was like, ‘I’m in the wrong movie. What just happened? Call the director. Call the producer. This is not my life. This is not my movie. And I went home that night and I wrote down my strengths, and what I thought I was good at. And the only thing in the ‘good’ column was sales. And I thought, OK well, I know I’m good at selling. What is it I like about selling? And I realized I like offering something to someone that they need, or didn’t know that they needed that can improve their life, or help them. And so in that moment I wrote down in my journal, ‘I want to invent a product that I can sell to millions of people that will make them feel good.’” —Sara Blakely, Goldman Sachs Fireside Chat

To be clear: we are not talking about “pseudo-manifesting” where you sit in your bedroom, drink beer, and wish you were Elon Musk while rewatching all five seasons of Rick & Morty for the fourteenth time. 

Manifesting means viewing your career as a science experiment.

Some opportunities, we discover. Others, we create. And some are a mix of both discovery and creation. However you get there is fine, so long as you open the aperture of your mind and think like a scientist or artist (such a fine line!) trying to learn new things, hoping each failure leads to a new learning, and enough failures and new learnings lead to a breakthrough. 

So, in this “mini-book,” we are going to dig into both aspects of career serendipity:

1. Recognizing serendipity: How to spot exponential moments

2. And engineering serendipity: How to spark exponential moments more often.

The first obstacle most people face in their careers and their lives is even being able to recognize or acknowledge serendipity in the first place. These people are surrounded by serendipitous moments with exponential potential but fail to recognize them. They might be cynical. They might view life through a pessimistic lens, and refuse to believe the universe could ever (EVER!) conspire in their favor. Any gifts they receive—be it an introduction to the right person at the right time or stumbling across a new and valuable piece of information—are discredited as dumb luck and quickly forgotten. But as the adage goes, “Pessimists are usually right, and optimists are usually wrong but all the great changes have been accomplished by optimists.”

Or, said differently: 

Pessimists live in the past. 

Optimists live in the possible.

The second obstacle people face in their lives, if they are open and willing, is figuring out how to engineer serendipitous moments with exponential potential more often. They’ve seen the power, now it becomes a question of a) how to spot and act on more and more of these moments earlier and earlier (sort of like insider trading but within your life), and b) how to form habits, friendships, and put yourself in situations where these exponential moments are most likely to happen—the same way dry brush, hot temperatures, and strong winds increase the likelihood of a forest fire.

Both recognizing and engineering serendipity in your career, business, and life are crucial to living with purpose, but also to making the most of your time here on earth. 

After all, it’s “happy accidents” that tend to unlock the most emotional, spiritual, and financial upside. 

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