Lightly, my darling

When you don’t try to make things happen, they just happen.

This is how my world has worked this past week.

I can’t decide if it’s a psychological trick or actually, you know, karma.

So when I sat down to write the newsletter this week, I wandered down an internet rabbit hole in search of answers and found, well… serendipity, somewhat serendipitously.

I’ve touched on serendipity before, but this is a deep dive. If you’ve ever felt the phenomenon of stumbling onto something valuable you weren’t looking for, then buckle up.

It all began last week. Focusing on a passion project as an alumni mentor for Write of Passage, the online writing school run by David Perell, I’ve drawn incredible energy from the community of amazing students. My attention is on the course and I’m having a blast. But I’ve had no time for outbound sales and marketing for Curious Lion.

Only this week, we’ve been swamped with five inbound requests! This does not happen every week. This would be a good month. With outbound driving it.

So while thinking about nothing other than how to make this cohort the best possible experience for the ~30 odd students who have chosen me as their mentor, we’re busier than we’ve been all year with scoping out new work.

So what is serendipity?

Serendipity is one of my students posting in our weekly writing group this quote, before I started thinking deeply about this:

“It is those who are least motivated to pursue extrinsic rewards who eventually receive them.” – Daniel Pink, Drive.

The word “serendipity” was coined by Horace Walpole in 1754. He was intrigued by a Persian fairytale called The Three Princes of Serendip in which three princes of what is now Sri Lanka traveled the world, “making discoveries, by accidents and sagacity, of things they were not in quest of…”

It really caught on in the world of scientific discovery. Perhaps the most famous example is the accidental discovery of penicillin by Scotsman Dr. Alexander Fleming.

Joseph Henry, the physicist and first director of The Smithsonian Institution talked about how “the seeds of great discoveries are constantly floating around us, but they only take root in minds well prepared to receive them.”

Louis Pasteur commented how “chance favors the prepared mind.”

Aren’t we talking about luck here?

Luck and serendipity are certainly similar, but serendipity is a narrower, more precise idea: finding pleasing things you weren’t looking for.

Luck can mean this too, but it can also be used to refer to success in general (as in, you make your own luck). Luck can be bad too, while the same cannot be said for our dear friend serendipity.

Can you influence serendipity?

Strictly speaking, no. It’s in the definition that you’re not looking for it in the first place.

But what Henry and Pasteur were getting at is the part of it that really interests me: the prepared mind.

Two students from Write of Passage echoed similar sentiments on Twitter this week.

Too much of anything kills your crop of luck. I love that.

We can sense when someone wants something from us versus when they are showing up fully in service or as themselves.

The generosity of spirit and authenticity that Kyle is referring to, and not overdoing it, as Dan suggests, are both key elements in preparing your mind for serendipity.

You may not be able to create serendipity, but you can sure be there for it when it arrives.

“It’s dark because you are trying too hard. Lightly child, lightly. Learn to do everything lightly. Yes, feel lightly even though you’re feeling deeply. Just lightly let things happen… so throw away your baggage and go forward. There are quicksands all about you, sucking at your feet, trying to suck you down into fear and self-pity and despair. That’s why you must walk so lightly. Lightly my darling.” – Aldous Huxley

Until next time, my darling.


P.S. I thought the growth was crazy two weeks ago. We’ve now grown from 513 to 594 subscribers! Welcome to this community of curious humans. My goal of 1,000 subscribers by the end of Sep is in sight ?. A massive thank you to everyone who shared. ?

For all new subscribers, this is not your average company newsletter. In fact, it’s not really a company newsletter. It’s a personal newsletter with a focus on what I’m most most curious about.

I hope you enjoy and reply often. I respond to every email I get.


Another tie two weeks ago, with the most clicks split between people jonesing for a 4-day workweek and those interested in things simple to understand, but incredibly hard to do (introducing my concept of the Learning Flywheel which I updated last edition).


?‍♂️Sprinting Without an End in Mind Will Only Exhaust You

As a growth advisor for a company that helps other companies optimize their expenses, I was chatting with the owners this week and one of them said they have a target of 50 clients. They are equipped to handle many more, so I asked why 50?

What he said to me was so revealing about how he does business: “if you just keep sprinting without knowing where you’re going to stop, you’ll exhaust yourself.”

He said, between us, the goal of 50 is artificial. They can handle more, but 50 is when they will stop to take a breath. At that point they have plenty of options:

  1. Set a new goal for more clients.
  2. Optimize the mix of clients, dropping those that are more hassle than it’s worth.
  3. Hold steady, build MRR and start discussing exit plans.

James Clear wrote about how Southwest Airlines adopted a similar upper bound limit for their growth that set them up to be the only airline that made a profit for nearly 30 consecutive years since the 1970s.

We are all good at setting lower limits for our goals (‘I will make at least 10 sales calls a week…’), but not really upper limits. Upper limits make it “easier for you to sustain your progress. And the power of sustaining your progress is that you end up blowing away everyone who chased success as quickly as possible.”

?33 Things I’ve Stolen

Ryan Holiday is one of my favorite writers, and he recently published this reflection on 33 ideas he’s stolen from others for his 33rd birthday. Here are a few of my favorites:

  • Love is best spelled T-I-M-E. I don’t think I’ve heard anything truer or more important in my role as a husband or father.
  • When someone tells you something is wrong, they’re almost always right. When someone tells you how to fix it, they’re almost always wrong.
  • Whenever you feel like criticizing anyone, just remember that all the people in this world haven’t had the advantages that you’ve had.
  • Amateurs focus on outcomes more than process. The more professional you become, the less you care about results.
  • Go to what will teach you the most, not what will pay the most.

Check out the full list of 33 ideas.


We published two since I last wrote to you:

  1. 13 Online Learning Lessons from Skillshare – notes from a fascinating discussion between David Perell and the CEO of Skillshare, Matt Cooper.
  2. Am I a Writer? – my reflections on what it means to be a writer, “in conversation with” Brian Koppelman. ?


“Serendipity is jumping into a haystack to search for a needle, and coming up with the farmer’s daughter.” – Julius Comroe


This email newsletter was originally shared with subscribers on July 12th, 2020. To receive the latest newsletters twice a month, sign up below!

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