Secret Backroads

Continuing the theme of not knowing / unknowing from yesterday . . .

My favorite part of late July has been a shift that I’ve noticed in my son, who is just starting out his journey as a teenager.

Lately, he’s been asking me lots of questions. An easy 300% more than usual and none of them having to do with screen time or his next meal.

As we weave up the switchbacks on our way from Lloyd Road to the Highlawn Pavillion on our way to West Orange . . .

How do you know your way around all these secret backroads? How did you learn about them?

As we ease onto and off 280 West or East . . .

“How did these roads get these names, and why are so many of the names numbers?

As we pass an ice pack back and forth on the couch, from my foot (running) to his leg (soccer), and he clicks the TV from the Democratic debates to WWE Smackdown . . .

Why are these the people who are running for President? Is this real? Do you think that hurts?

As we wait for yesterday’s pizza to heat up in the oven . . .

Why is milk a sponsor of the Olympics?

Though I can’t answer most of these questions, I love them so much. They wake me up to the life around me, show me a young man starting to crawl out of himself and into the world, and remind me that we often know each other best when we wrap our arms around what we don’t know, solvable or not, sayable or not. We have no clue. And that’s just fine.

Just make a left, there, at that fence near the pine . . .

The Word Cloud of Unknowing

I suppose one way to judge a week, and one’s inquiries during that week, is to make a list of the words or phrases that you had to look up or, as my kids would say, search up. So far this week, here’s my word cloud of unknowing:

Phase transition

Infill site

UTM code

I’m not going to define these terms for you because, depending on the kind of week you’re having, searching them up could be just what you need.

Actor or Agent?

When planning and dealing with all the problems and possibilities inherent in any given week, ask yourself:

Am I the agent or the actor?

Being the agent requires you to ensure the conditions for someone else’s performance. You need to market the show, check the lighting and sound before the show, coach the actors where necessary and in the right ways, manage the audience, and deal with all the unexpected things that happen up to and through showtime.

Being the actor requires you to bring your full self / energy / attention to a situation. You need to ensure that you are well trained, well rested (or as a runner would say, appropriately tapered), fueled, and clear headed.

Look at your big events or meetings for the week and apply the Agent or Actor lens. See if that makes a difference in how you approach your work and the way things unfold.

Make Yourself Clear: The Owen Jennings Edition

Thus far, I’ve expressed Make Yourself Clear gratitude to Jason Wingard, Dean of the School of Professional Studies at Columbia University, and Keri Potts, Senior Director of Communications for ESPN. Today, I’m turning my attention to Owen Jennings, Product Lead at Cash App, a mobile payment service developed by Square.

I met Owen when he was a high school student who would ask me questions that routinely exposed the limits of my knowledge. For example, he once walked into my office and said, “I’ve been comparing a few respective citation system, and I have some questions about inconsistencies I have found.” And then he walked through them, item by item, my curiosity rising along with his as I said, “I don’t know . . . let’s find out . . . you’ve stumped me . . . that’s interesting.”

I followed his career as he moved from studying philosophy and researching health care in college to working for Ray Dalio at Bridgewater to ultimately falling in with the finance arm — Square — of Jack Dorsey’s business interests. When people heard about those transitions, they frequently scratched their heads, but they all made sense to me. Owen Jennings is one of the most indiscriminately intelligent people I have ever met.

What I mean by that is simpler than it sounds. Regardless of the topic or problem, he rises to it with vigor and questions. Could be Sartre; could be scooter-sharing systems in San Francisco. He likes to take things apart so that he can understand them. He likes to know how the world works, and he knows that you can get there, to deeper understanding of the world, through a variety of pathways. Citation systems, philosophy, health care, economics — there’s really no need to compartmentalize. All puzzles strengthen the enigmatologist; and all solved puzzles improve all unsolved puzzles. Or at least that’s what Jennings continues to teach me as he continues to introduce me to things that make me say, “I don’t know . . . let’s find out . . . you’ve stumped me . . . that’s interesting.”

When Reshan and I spoke to him while writing our book, he seized most quickly and directly on the concept of Immediacy, which we define as “what happens when a transaction occurs at a time when it is most meaningful and helpful for all parties.” In fact, Jennings said that Immediacy was “top of mind” when his company was building one of its most innovative products, Boost.

Boost allows customers to receive instant discounts from debit card purchases. In our book, Jennings offers a deep look (or, rather, as deep as our editor would ultimately allow him to go!) at what are called “rewards programs” associated with credit and debit cards. In so doing, he explains the way in which Boost is using Immediacy to improve transactions, by improving rewards, between paying customers and brands. To simplify greatly, when a customer earns a Boost on a product like, say, Chipotle, he or she receives an instant discount, eliminating the usual game of accruing points and ultimately trading them in. The brand, in this case, Chipotle, also benefits in terms of customer acquisition and retention.

Jennings helped us to understand how Immediacy is serving as an operating principle for some of the most innovative products and services currently available. As is his way, though, he also helped us to understand a completely different aspect of our work — Authenticity — when he went off on a tangent about how customer service is changing in many industries due to excessive automation. We included that excerpt in the Authenticity section of the book because it was simply too good to leave out of the final manuscript. Which is a good way to think of Owen Jennings more broadly, and across the variety of fields he inhabits.


Below is some of the art that has appeared on the Cash App Twitter page on Fridays. I’m including it because I’ve mentioned the first two sections of our book and not the third. The third section is about Delight. Here’s some:

Readers, United

As people have read and reacted to Make Yourself Clear, we have been building out a page on the book’s website to show a chapter-by-chapter progression. Here’s a quick invitation if you’re up for it.

  1. Read what readers of MYC have been saying.
  2. Send us your own reaction to a chapter (or to what has already been said about a chapter). We’d love to include more voices on the page, which if you haven’t clicked on it yet, looks like this:

The Extra Two Minutes

Reshan and I recently interviewed an incredibly productive professor. He has written a dozen books, many of them the leading textbooks in his field, is often voted the “best” professor at the business school where he teaches, serves as an advisor to businesses and entrepreneurs, and produces a blog and Youtube channel — both offering pure substance and no fluff –that routinely reach over a hundred thousand people. Though I’ll publish this interview before the summer’s end, here’s a piece of advice that won’t make the final cut. It’s one of the moves that make him so productive.

When you’re done with something, you just want to move on. I say, look, take the extra two or five minutes to make it usable on another front.

For example, when I write an email which is a long email that answers a question that I’ve been asked before, I copy and paste it into a document, which then helps me create something that I can put on my website as a “frequently asked question.”

It takes an extra two minutes, and I don’t want to do it. I’d rather move on, because I have other things to do, but that extra two minutes saves me god only knows how many questions I’ll get in the future on that particular issue.

So the next time you complete a task that produces a product, even a very small one, ask yourself a simple question: can I make this usable on another front? If the answer is yes, and it won’t take long, give it a shot. See if your output changes. See if your audience responds.

Off the Track and Onto the Trails

I recently listened to a good conversation between podcaster and athlete Rich Roll and Matthew Futterman, Deputy Sports Editor for the New York Times.

Futterman’s new book is about Bob Larsen, a legendary running coach and the driving force behind some of the most lasting innovations in the sport’s history.

At one point, Roll and Futterman talk about the way Larsen helped his athletes to move away from the daily grind of training that was the dominant ideology at the time. In short, he moved his athletes “off the track and onto the trails.” He taught them to run based on feel and to perform what, today, would be called “tempo” runs.

Surely, at the time, Larsen’s methods must have been questioned by both onlookers and perhaps his own athletes. He was cutting against the received wisdom of the day. (I’m looking forward to learning more once my copy of the book arrives.) When Futterman looks back, though, with the gift of hindsight and an inquiring mind, he is able to unpack exactly what made Larsen’s methods so useful for his runners.

The track and the pool are really, really good for one person. And that’s the coach. Because the coach can stand in the middle of the track, or can stand on the pool deck, and can have the watch and can monitor everything. But he or she is not the one going around in circles like a hamster all afternoon or going back and forth in the water all afternoon, slowly going mad. But when you get off the track or you get out of the pool it’s just, for obvious reasons, liberating. You feel free.

Source: Rich Roll Podcast

Of course this makes me think about the classroom . . . about teaching . . . about teachers.

If you’re a teacher, have you thought through your teaching methods or are you simply doing what you’ve always done? Are you simply teaching the way you, yourself, were taught or according to some form of received wisdom? Is the received wisdom even right?

One level deeper: Is what you’re doing in your classroom serving the needs — and instincts and intuitions — of the students in your care, or is it simply giving you a feeling of control. Is your practice serving you (or your administrators) or is it serving your students?

And, most important: is your teaching making your students feel more liberated, more free?

The classroom, it occurs to me, is often really, really good for one person. And that’s the teacher. Because the teacher can watch and monitor everything. But he or she is not the one going around in circles . . .

I can’t wait to read Futterman’s book because I know it will not only teach me about a sport that I love, but also broaden my perspective about teaching and learning. More on all of that later!