8: Ask Simple Questions

7/2/17

In my last letter to you, I tried to persuade you and share my honest reflections about reading and how to really read. And I stand by that. Books are a wonderful way to develop, and satiate for that matter, curiosity, which is the fist pillar of choosing goodness.

But there is so much more out there to explore than just the things you find in books, like other people. People and their meditations about their experiences are also rich sources of the stuff that cultivates curiosity. A lot of wonderful thoughts, stories, and ideas never make it into books. These thoughts remain exactly that - thoughts - until they are discussed in open air. This, to me, is what’s special about human conversation, it unless potent thoughts from other people’s minds and allows those thoughts, through conversation, to turn into wisdom that can be shared with others.

But this reveals a quandary - how does one unleash the important but frozen wisdom that resides in the minds of others? The answer is simple: ask questions. However simple that may seem, there are many topics to consider about questions: how to ask them, what should you ask about, how do you actually listen? Let’s discuss questions, explore why questions are critical to cultivating curiosity, and how to actually ask them well.

First and foremost, ask lots of questions. Quantity drives quality. The more sincere questions you ask, the better you will become at asking them. The worst kind of question is one never asked.

When you are first learning something new, your questions will be novice and unsophisticated, you will know this very acutely and you may feel shy about asking a question you have. But all that doesn’t matter. If you sincerely want to know, ask the question. Ask it. And iN promos, as you ask more questions, the easier it gets and the more fruitful they are. Like most things, asking questions takes practice. The best way to get better is to just ask more questions. At the beginning of learning something new, just start.

(12/31/19: When I first drafted this letter to you in 2017, this is what I wrote: “Once you start, however, you might ask good questions if you’re going through the trouble to ask them in the first place. The best advice I can probably give you is to ask, “why?”. There are may interrogative words, of course: who, what, where, when, how. But “why is the question you really need to get to if you want to dig into an idea.”.

But in retrospect, even though asking “why” is really important, I don’t think it’s the best advice I can give you. I’m going to revise what I wrote from this point and let you know when I resume drafting from the original text.)

If you’re going through the trouble to ask questions in the first place, however, you might as well ask good ones. The best advice I can probably give you is three-fold: be simple, sincere, and follow-up.

I took a great class in business school, in 2015 during my last semester, with Bob Quinn. The course, called Transformational Leadership, changed my life. The basis for the class were two of Professor Quinn’s books - Lift and Deep Change.

(The framework in Lift is brilliant and I think of it all the time. Any time you're doing something, in particular something new, ask yourself the four Lift questions. The first, and most important, is “what result are we trying to create?”. When asking that question and the three others, you become focused, centered, grounded, and motivated. It’s incredibly powerful. You must read it.)

In the class, we had to put the concepts of Lift into practice. I asked myself the four Lift questions about how I use facebook. I came up with an idea to ask a sincere, reflective question every day on facebook. I no longer ask a question every day, but I do it several times a week, still.

Asking these questions has helped me to learn greatly about the hopes, dreams, and beliefs, of others - and myself. It would not be a stretch to say that I better understand the human condition, now. Beyond that however, I probably have nearly 1,000 reps asking questions. That’s rich data that’s helped me to understand how to ask a good question.

Simply put, the best questions are simple. That means they are clear, written in plain english, and succinct. Every word has a purpose. There is no fluff. A good rule of thumb is to be able to ask a question in one breath in one short sentence. Ask questions in this way makes them easier to answer. Other people appreciate simple questions and in my experience answer them with greater energy, detail, and honesty.

(My college friend, Ms. Lainie, received some good advice from her Mom, which I always thought was smart and charming. She shared it with me once. If you really want (someone) to understand what they are supposed to do, you have to be able to write your direction on one side of one post-it note. If not, it’s too complicated. I always thought that was fantastic advice. She shared it in the context of a wife giving her husband a task to do, but I think it applies to questions too.)

And, if you hold yourself to the standard of asking a simple question, and practice doing so, you start to get really choosy about words and about framing. If a question is short, every individual word matters more and is more likely to reframe the word’s meaning. Choosing words carefully makes your question more specific, which again, makes the answers you receive on them richer and more relevant.

Moral of the story: the simpler the question the better.

In asking these hundreds and thousands of question on facebook, I’ve also realized that that I get better, clearer, and more interesting responses when I ask a question sincerely. By that I mean, when I ask questions that I really want to know the answer to. Or, a question that I don’t already know the answer to, and that I’m genuinely curious about.

I don’t have data and studies to back this up, but other people don’t trust you when they think you don’t really care about the answer to a question or if you’re trying to brag or if you’re trying to trap them with their answers. And they can tell. It’s hard to fake sincerity over the long run. People just have a feel for it, I think.

It sounds silly, but lots of people ask questions that they either already know, or don’t really want to know the answers to. For us then, the advice is simple. If you really want to know the answer to a question, ask it. If you don’t, don’t.

This also sounds silly, but another way to really ask a good question is to follow it up with another question. And another question. And maybe a few more questions. Certainly, asking bogus questions is worthless, but I’ve found that treasure is normally not buried six inches below the surface. To really learn something from someone, you have to dig deep. Which again is aided and better guided when your questions are simple and are asked with sincere curiosity.

In my experience, a well crafted question sincerely asked begets learning. And learning begets curiosity, which begets even more well crafted, sincerely asked questions. The punchline is this: If you ask good questions, it starts a virtuous cycle for learning and curiosity.

So to summarize briefly, be simple, be sincere, follow-up. If you do these, you’ll probably be asking questions which help you grow your curiosity and your wisdom.

(This is where I am resuming to the drafted text of my original letter from 2017. But before I do that, let me share a few other simple questions that I find are useful in many situations. There’s “what result are we trying to create?” and “why?” which I mentioned before, but merit repeating. Also: “what’s that?”, “how does that work?”, “why do we do it this way?”, “who is this for?”, “what do you think?”, and “what happened, exactly?", “how do you feel about this?”, and “why does this matter to you?”. There are certainly more questions simple questions you can add to repertoire, but these are a few of mine that are tried and true.)

Thus far, we’ve covered a few ideas: ask lots of questions, and, if you’re going through the trouble of asking questions you might as well ask good ones. Do do that, try to be simple, sincere, and follow-up. But these suggestions give the incomplete and inaccurate impression that questions should predominately asked about others and the world external to your own mind. That’s precisely the opposite of what I have found to be true about questions, especially as it relates to the enterprise of goodness.

If you are committed to the path of choosing goodness, and conducting your life in a way that reflects goodness, you must evaluate whether your thoughts and actions are good. In addition to asking questions of others, it is essential that you ask questions of yourself. In other words you must reflect.

Questioning yourself is not a trivial activity. Even if you have managed to muster the humility to acknowledge the fallibility of your of your own character and question it, you must then do something even harder - be honest answering your own questions. (We will get to discussion of humility and honesty soon, and throughout. They are running themes throughout this inquiry of hours because they are a true test of whether you are motivated to endure the lifelong struggle of developing your character strongly enough to choose goodness.)

But questions of yourself, when sincerely asked, are extremely good tools to determine what goodness is and whether it is reflecting in you. Asking these questions of yourself will help you understand what a life committed to consistently choosing goodness looks like. (This sounds lofty and abstract, but in practice it’s not. Two simple questions you can start with are, “what does a good person think and do?”, and, “am I a good person?”. I originally had a whole sections about the dark side of questions, but it didn’t fit with the broader argument I was making here. It was extraneous to this letter, but still relevant. Questions, when wielded irresponsibly can be an instrument of power and control. Leading questions help you to hear the answer you want to hear, instead of the truth. Questions can be asked in a way that raises false hearsay or with the intent to shame and bully others instead of pursuing the truth. Questions are a powerful construct, it is up to you to use them to advance goodness instead of power and control.)

Doing this takes effort and practice. Along th way, I’ve learned to reflect and am much better now for it. For me, it started because of a lucky break in school. I was always part of student council and student groups, and because of my involved I was afforded the opportunity attend conferences and camps that were designed to “develop leadership” in youth. Student Council Camp probably changed the course of my life because the adults there made reflection a foundational part of the curriculum. We would have deeply compelling activities, but the real learning occurred during the debriefs that occurred after the activity.

The adult counselors would push us to articulate our thoughts and feelings by asking deeply introspective questions about things like identity, integrity, justice, and conflict. They would dig and dig and then ask why again. I learned to reflect at summer camp, and that’s one of the luckiest breaks I’ve ever had.

I have tremendous gratitude for the student council advisers and camp counselors I had in high school because they taught me to reflect on my actions and thoughts, and challenged me to be honest with myself about whether I was a good person with true character. It is now my responsibility to help you. (Ask your mother about Kairos, i think you’ll find that it’s an experience that affected her in a similar way).

No matter what, when it comes to reflection, you just have to start somewhere. I have always liked to reflect through writing. When I was about 12 or 13, I bought a notebook and called it the “Question Book". I filled up the first two pages with questions I wanted to think about and started to answer them one by one.

Throughout the years I’ve kept writing (obviously), which may or may not be suitable for you, but it has been a wonderful reflection mechanism for me.

Later in life, your mom and I started to talk and reflect together once we started dating, very early in our relationship. We’d take time to do a “temperature check” every week on Sundays, taking turns answering the same five questions: appreciations, issues, requests for change, what we’re thinking about outside of our relationship, and family logistics. (Your mother and I continue this to this day, and we have missed less than 4-5 weeks in our whole time together - which is over 6 years at the time I’m writing this. Here’s more detail on our weekly “temperature check.”)

I am not trying to prescribe a reflection mechanism for you, I merely offer you suggestions to help you find something that works well for you. But what I would urge you to understand, however, is that you will never reflect if you do not create time and space for it. You have to create protected time, with a clear mind, to slow down and step away from the challenges of day to day life. You might even need a dedicated, regular physical space for reflection, too, whether it’s a notebook, a place in the house, or a hideaway around the City or in nature.

But perhaps the most difficult space to come by is the space in your heart. Your whole life, and certainly when you first open your heart, humbly, to reflect, it will be uncomfortable. It will be uncomfortable to ask yourself tough questions, because you may not like what you see after you start asking yourself those questions. (I was having drinks with Uncle B and his friend Zack over Thanksgiving this past year. Zack made this point more eloquently than me, here’s a post summarizing what happened.)

We, because we are mortal men, do not have a perfect ability to choose goodness over power. Some of what we are feels ugly, because, to be honest, some of what we are is ugly. You have to work hard to create the space in your heart to accept the truth, forgive yourself for what’s ugly, and choose to slowly evolve into something different and good. Without this space in your heart, it will be very difficult to reflect on difficult but exceedingly important questions.

The toughest questions you can ask yourself, like: why am I here, what matters to me, what is good, am I good, why have I been put on this Earth, and others - are the most critical to ask if you want to discover what goodness is and cultivate a capability within yourself to choose it. All these questions are ones that you’ll want to avoid talking about, even with people you love, trust, and respect. You’ll probably think that those questions are too big, and too much of a burden to ask others.

But you must. You must not shy away from these questions simply because they are hard.

I’ve found in my short time on Earth that others loved to be asked tough questions when they are asked sincerely and simply. If you don’t, you may go damn near your whole life without asking them, and have decades of regret.

Your Dada and I had a conversation about what he liked, wanted, and cared about. I remember exactly where we were standing in the kitchen, around the island at Dado’s house. It was in the evening, because it was dark. Your Dada was in his early sixties, I think.

He seemed to have a powerful revelation, even though I was just talking with him asking him sincere, simple questions. He told me that nobody had ever asked him questions like that before and that he feared it was too late for him to change anything about his life, his health, and his habits. Part of me, even though I know his death wasn’t my fault, wonders if he would still be here if I, or anyone else, asked him those questions of heart earlier in his life. Would he be more at peace? Would he be less stressed? Would he have taken better care of his health?

I will never know, and despite my guilt I am relieved that I was able to talk about such things with my father and that he was able to open his heart, even if for a moment, to his son.

I hope, my son, that you are able to open your heart - with and without my help - so that we may reflect on questions of the heart together, someday, too. It will be difficult, but I have no doubt in my mind or my heart that you find it to be well worth the challenge.

Love,
Your Papa

7: Really Read

5/28/17

Let me be forthcoming because I have a very strong bias when it comes to reading.

I love reading and so does your mother.

When we first moved into this house, during the first week we asked each other what our favorite room was. We both, very quickly, said the library. You’re being born into a family of bookworms.

There are so many reasons to love reading. First, it’s so captivating; there are so many great stories that take you all across the world, universe, and fantasy worlds. They take you into the most joyous moments of a character’s life, or, let you feel the terrible feelings safely, before you live them yourself. Books are an enchanted place.

Reading is fun, an emotional release, and a vacation, or a spaceship, or a time machine. The best books are masterpieces of art. Reading a good book, and I mean a good book, across any genre, is a joy.

And to top off all of that, I have so many wonderful memories because of books and reading. Your Dada and Dadi read with me and would take me to the library, all the time, wherever we lived. They would read to me and we would read together. There are cassette tapes (ancient technology, I know) of us reading together, which I cherish. I’ve received so many books as gifts, which were shared with so much love, likes once from your mom, aunts, and uncles.

And the best discussions I’ve had come from reading books. In college, high school, adulthood. Books have made my life so much richer.

Beyond these wonderful, beautiful things about books, there are many practical benefits, especially as it relates to becoming curious and becoming good. But before I go into nuances, be sure that the joy or reading itself would be enough to justify spending time with a good book. Reading is necessary and beneficial for other reasons, but reading needs no practical purpose to justify it. More than anything, read because it is beautiful.

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Reading - and by that I mean not just casually reading, but really reading - is absolutely essential for developing curiosity and in turn goodness. It is a potent way to do two extremely important things: answering unresolved questions and wonderings that you have, and, nurturing the inspiration for new questions that lead you to explore and discover. Reading a good book or essay is to digest a potent and concentrated morsel of insight, precisely because someone had to write it. Writing is a process that takes ideas and strips them of their excess. A well written book has nothing but truth left on the page.

Writing is much like making a sauce in that sense. The sauce has many delicious ingredients - water, wine, cream, parsley, garlic, or others, depending on the sauce. But in the process of making a sauce, the chef must take great care to cook it so that the excess liquid is evaporated away and the sauce thickens. What remains is more concentrated, flavorful, and with a better texture.

Writing does the same for ideas and stories, at least when the writing is done well. A good writer, evaporates all the unnecessary “water” leaving only the parts of an idea that are aromatic, flavorful, and potent for the mind. Consequently, reading good writing is an extremely efficient medium for cultivating curiosity - the process of writing leaves a good book with only the most valuable, nutritious, and delicious parts of an idea.

Writing then, is a great labor in service to you, the reader, because it evaporates away all the unnecessary elements. But as a reader, you still have a tremendous labor of your own.

Reading, when done well, is hard work. There’s a difference between reading and really reading. Here’s more of what I mean by that.

The first litmus test between reading and really reading is that of purpose - are you reading for comprehension, reading for the pages, or reading to learn?

Reading for comprehension isn’t a terrible reason to read. Comprehension implies that you are simply reading to understand and remember what the author is saying You’re reading to understand the basic who, what where, when, and why. When you read this way, you’re not reading for deeper thought or a nuanced understanding of the idea or story. In these circumstances, reading for comprehension, you just want to put some information into your head and be able to recall it coherently.

Reading for the pages, on the other hand, is something to avoid. It’s not worth your time, and if you’re reading for the pages it probably means you are cutting corners, or worse, reading to feign intelligence (which at it’s root, is a power-seeking behavior).

What I mean by “reading for the pages” is that you are reading to finish the book or essay as fast as possible and “get it done.” The goal of reading for the pages, rather than learning or even comprehension - at least for me, when I’ve done it - is less about gaining something from the text, but being able to signal to other people that I’ve read it.

But what is the point of doing that? If I were to steal someone’s respect or recognition, why do that by reading for the pages? Reading, even if done for the pages, still takes lots of time. Why not just read a summary of the book if I were to do that? Why not just feign the appearance of reading a book? (The best reason I can think of (for reading a summary or feigning appearance of reading a book) is because the feigner knows reading a book and sort of reading a book aren’t the same thing. They are socially, and perhaps morally, different enterprises. Conflating the two feels deceitful not only to others, but to yourself. Which, to me, is the most dangerous kind of deceit.)

Reading to learn, however, is an entirely different enterprise. The intended outcome when you read to learn, is not just literally understanding what the author is saying. Rather, the intended outcome is changing your self in some way, whether that is deepening your understanding of an idea, seeing the world in a new way, or changing your mind about something. If something about you, however is small, is not changed, you have not learned.

In that way, reading to learn is absolutely exhausting. Reading to learn (the type of reading I mean when I say really reading) takes tremendous focus. You must be listening to the author and providing them your undivided attention. That means eliminating all distractions, and ignoring the concerns of your day-to-day life for awhile. When you are really reading, the book must be your only concern because we mortal men tend not to be good at multitasking. The world is a distracting place, so creating the focus required to really read is really hard.

When reading to learn, it is also best, in my experience, to read slowly (your mother is good at this, if you watch her read something you can tell by the way she moves her eyes that she is methodical and absolutely incisive of what she’s reading). Reading slowly allows you to not only absorb and comprehend what the author is saying, but question it and even explore it through a daydream. When reading slowly, you create the opportunity to reflect on what you are reading and ask questions like:

• Why?

• Does that seem believable?

• Why would the author mention that?

• What is the author not saying?

• How does this relate to the overall thesis of the book?

• Why did the author use this particular word?

• How is the author biased?

• What works has the author built upon?

• How could I build on this idea?

• How does this idea play out in real life?

• How does what the author is saying affect my life?

You cannot even ask these important questions (they are important questions because these will not only help you to understand but to change) let alone reflect on them if you do not go slow.

(Which means you should slow down reading this. Not to imply that this is a good book! You’re the judge of that).

Moreover, really good books that are deep with emotion or rich with ideas and provocative arguments aren’t always easy to read. They take time. It’s not only okay but probably should be expected that you have to read passages over and over again (or the whole book, there are only a few titles that I’ve re-read - Profiles in Courage, the Baghavad Gita, and maybe East of Eden are the only three I can think of). Sometimes, I’ll read a challenging section two or three times, and if I’m using that time to go deep with it, it’s well worth the trouble.

This perhaps isn’t obvious, but what you read matters a lot. Like, a whole damn lot. As I’ve learned working on technology and data projects, “garbage in, garbage out.” What you put into your mind will affect what comes out of it. But I’m not suggesting that you only read dense, esoteric, nerdy books that are from a limited amount of “appropriate” subjects. On the contrary, I think you should read whatever you like (and I highly suggest you mix fiction and non-fiction. I spent many years of my life avoiding fiction, and it’s wonderful and transformative to read both) and mix subjects and genres between ones that you are already interested in and ones that expand your horizons. There are plenty of wonderful and thoughtful books that are on seemingly impractical topics.

As an example, I’m currently pawing through a collection of short stories gifted to me by Miss Emily, a friend of mine from high school. She gave it to me years ago. It’s been sitting on my shelf for years and I finally picked it up. Despite being Russian literature from the 1800s, it has been a remarkably illuminating and relevant read, with prose that in some moments simply leaves me arrested and feeling whimsical at the same time

The point is, there are amazing books on many different topics and from many different genres, and from the authors that you wouldn’t expect.

But there are also terrible books. And by terrible I mean books that it’s plain to see that the author did not do the hard work of developing an original, valuable, thought. Or terrible meaning the author hasn’t put in the work to produce clear, deliberate, enchanting prose.

To me, terrible is less about topic and more about quality and honesty. Going back to the example of making a sauce, I’m talking about a careless cook, not a recipe with ingredients I don’t happen to fancy. (That said, there are books that are well written but are intellectually dishonest, biased, or tell what you what you already believe solely for commercial purposes. These are terrible and also dangerous, because they help you to learn something that is untrue or immoral).

For many years, I made the mistake of reading narrowly selected topics. This was in two ways. I would read books about the same topics, usually about business or government. Or, I might read books I was more interested in telling people I was reading, rather than what I was actually interested in reading (these were usually about business and government, too). To me this is just another form of reading for the pages, because the books I chose in both of these scenarios is driven by the expectations of others, rather than my own desires.

This seems bizarre to say, but I mean it sincerely: do not fear reading widely about a wide set of topics. If you read a quality book, something about it will stay with you and enrich your life and the lives of others around you, regardless of the topic. More often than not, reading across disciplines will give you a mental model that helps you make sense of a difficult idea in your primary area of interest. (I’ve mentioned a lot about intellectual diversity, there’s no better person to share why diversity matters than Scott Page, one of the professors I was really lucky to have during my undergraduate studies. We have a few of the books he’s written on our bookshelves at home.)

For example, your Aunt Alyssa gave me a book last Christmas which uses computer science concepts to inform how humans make decisions. It was brilliant and what I’ve read has helped me make sense of how we organize the cookware in our kitchen and how to conduct a search to fill a job at work. (The idea of a cache, was the concept helpful in the kitchen - stuff we don’t use often should go in the cupboard instead of on the counter. There’s also an algorithm for optimal stopping that’s useful to keep in mind when filling a position. The book, Algorithms to Live By is on our bookshelf, too).

You’ll probably notice that I’ve almost exclusively told you about reading books, as opposed to reading blogs, newspapers, magazines, or anything else. I’ve actually started to shy away from those except for blogs, local newspapers, and the Economist.(I think blogs are great because they occupy niches and go deep on a topic rather than appeal to a mass audience. I have cycled through many authors and subjects over the years, like interstellar travel, data visualization, marketing, strategy, personal memories grief, and others. I like the Economist because it has a very unique perspective - it’s globally-focused, comes out weekly so it’s not chasing stories frivolously, and it’s hilariously cheeky. Most daily publications I’ve found, mix in a lot of fluff stories to get clicks and have bombastic headlines to get attention. The Economist avoids this). There’s a simple reason for this emphasis on books, I’ve found that the quality of a piece of writing is inversely proportional to how hard it is to write and how long it takes to write. In that way, daily publications are usually rather low-quality - if the publication is covering yesterday’s news, the writer quite literally can only put a few hours work into writing.

There are certainly exceptions with some excellent blogs, newspapers, and podcasts, but I’ve come to generally prefer books. When you finish a really rich, challenging book, it feels like you’ve done something special, too.

But let me return to the central question, as we must always do. What does this all have to do with curiosity and choosing goodness?

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When I was growing up, personal computing was emerging, as was the internet. The world, even now, is continuing to go digital. One of the antecedents of this idea became to think of the mind as a computer and to describe the functions of the brain as functions of a computer’s component parts.

But, in my time, I’ve come to see the brain as much more than just a biological information processing machine. (The scientific consensus seems to be that we know very little about the brain, consciousness, and the mind. Which will probably change a lot during your lifetime. That’s very exciting). The mind, the abstract thing that creates new ideas and is susceptible to inspiration and wonder, is something that is not fixed or static. It evolves itself. The mind is not a machine, it grows.

Curiosity is that voracious appetite for a mind to grow and evolve itself. Curiosity can and must be nurtured, lest it stop. Without curiosity, the mind becomes more and more like a machine - fixed and non evolving. In that way, curiosity is something foundational to keeping us human - it inoculates the mind from becoming stiff and like a machine.

Really reading is a terrific way to nourish curiosity because of how adventurous an activity it is. When you take a good book and really read it, it forces you to pay attention and consider new possibilities. Really reading forces your mind to work in ways that it hasn’t before and stay flexible. Really reading does such more than simply adding information to your memory bank, it keeps your mind from becoming a memory bank.

Really reading is also terrific for cultivating curiosity because of how much ground you can cover in a book - books transcend time, space, and even reality in a relatively short amount of time. Books don’t replace real-life experiences (and we’ll get to why later, real-life experiences are foundational to courage) but in books you can try something out. Reading a book can be like an experiment or an adventure. By reading, you can expose yourself to different circumstances and ideas, which allows your mind to consider many different questions and perspectives.

That negotiation of ideas, emotions, information, and perspectives seemingly magically cultivates a voracious appetite for you and your mind to grow. Reading a book book leaves you wanting more, which leads to more reading, which leads to more learning, which leads to wanting more, and so on.

Perhaps this is a pessimistic view of the world, but in your day to day life, nobody will make you reflect about goodness or how to choose it consistently. The world, and in particular the country, you are being born into has a sophisticated structure of laws, institutions, and incentives - none of which specifically prioritize or reward goodness or good character. I don’t even suggest that this is always intentional or even undesirable - our institutions depend on being able to measure things for them to be managed, which is hard to do with goodness.

As I’ve told you before, it can take a lifetime to begin to grasp goodness and how to choose it consistently - if goodness is hard to even define, how can it be measured, managed, codified, prioritized, and incentivized? This again, is why I want to share these letters with you - and try to share in them some of the traits and tools I’ve found helpful, in hopes that they are helpful to you to figure out how to consistently choose goodness, over the course of your lifetime. But again, for good reason or not, despite being an unbelievably important topic, no person will compel you to reflect on goodness.

But books, my son, they will. Good books that you really read, are a wise, honest friend that pushes you to consider the most difficult questions that can be asked of human beings in this universe. Books can be fearless in ways that we mere mortals cannot, because they do not die, which allows their most important elements - their truths - to be timeless and immortal.

Plato, Steinbeck, Lahiri, Orwell, Aristotle, Drucker, Kennedy - these are men and women I’ve never met, that have pushed me to think about the world, about goodness, justice, courage, and my own identity and existence in profound ways. They are people, through their writing that have - with the greatest care and love - compelled me to endure interrogation of gravely important questions in a way that only compares to the people who love me most in the world.

In this way - because of their ability to make those who read them, and I mean really read them, consider the topics and questions that humans struggle to raise with each other - books are superhuman.

I’m sure I will tell you many times as you, and the rest of your siblings we pray we get to bring into this world, that some of the happiest memories of my life are times reading with your Dada & Dada. These memories, some of my earliest, are ones that I have thought of often when your Dada went ahead last year. I’ve been trying to hold onto them as long as I can.

So, I promise you my son, that I will try my hardest to help you love reading, just as your Dada and Dada did for me and your Mimi and Granddad did for your mother. I can’t wait to read with you. I feel like I’ve been waiting my whole life to do it.

But I want you to know that loving to really read is so much bigger than just you and me. Reading is more than getting good grades in school or entertainment. Once you really read a good book, it gives you another ally on your journey to choose goodness. And that’s what matters most of all.

Love,
Your Papa

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If you’re interested in reading more of the Choosing Goodness project, I’d love to send you a quick e-letter when I share additions. Please leave me your contact information and I’ll be sure to keep you posted.

To see all the posts in this series, click here.

6: Slow Down

May 27, 2017

The most important class I took in business school was not a traditional MBA course. The course was a practicum and had three components: trying to launch a business using the lean startup method, working with an executive coach, and working with Dr. Melissa Peet on exercises related to a field she’s pioneering called Generative Knowledge. All were really life-changing, but let me tell you a bit more about what Dr. Peet taught us.

To start off the class, we did a very simple exercise, which turned out to be incredibly insightful, despite its modesty. The exercise is in three parts, and all it requires is a large room. If you want, you can try it as we go.

First, walk around the room like you do when you’re in “problem solving mode.” Act as if you’re trying to fix something, or like when you’re working on a big, serous, urgent group project at school. Spend about a minute walking around in the problem solving mindset.

Now that you’ve done it, think about what it felt like. What did you notice about the room? How did your body feel? What were you thinking about?

Next, walk around the room for another minute or two and pretend you’re in “social mode”, as if you were relaxing, hanging out with friends, or just taking a walk for fun. Ask yourself the same questions - how did it feel?

Finally, for the last round, walk around the room like someone who is radically curious, like the most curious person you can be. And kiddo, really push yourself to be radically curious. After you’re done, ask yourself those same questions. What did you notice about the room, how did your body feel, what were you thinking about? But this time, add one more question: what was different about each round of the exercise.

You probably felt very differently at each stage of the exercise, both mentally and physically. One of the biggest changes you probably noticed between the three rounds was speed - of your walking, of your heart rate, and of your mind. When you walk around in problem solving mode, everything is fast. It’s the pace of “getting stuff done.” Which, by the way, is an expression I loathe, but that’s a story for another time.

When you’re in social mode, it’s not as fast. But it’s certainly fast compared to the mode of radical curiosity. When your headspace is not just curious, but radically curious, everything slows down. Radical curiously is incredibly intense, but slow.

The lesson is an obvious one, but still difficult to practice: to be curious we have to slow down. To learn, your mind, body, and heart need to be open and absorbent, and that requires slowing down. In the world you are being born into, son, slowing down is hard. It’s something you are never taught. In the world today, you will be trained, cajoled, and incentivized to do the opposite - the world will do everything it can to get you to go fast. But you don’t have to always acquiesce.

So many people I have met, that will have children in your peer group, are obsessed with “getting things done”, doing more with less, hustling, and the like. It’s practically a national obsession right now to want to maximize time & effort, doing more with less, or squeezing in as many bucket-list items, and experiences as you can.

Have caution my son, because it is a trap.

Don’t fall into this trap, and I will try to help show you how to avoid it. It was a trap I was in, after all, for probably the first 28 years of my life. If you do fall into this trap of busyness it will be difficult for you to develop radical curiosity, which will make it difficult - in turn - for you to be able to choose a life of goodness rather than power, for reasons that we discussed earlier.

I encourage you to do the opposite of be busy - practice slowing down. I’ve tried to do this a lot in my life and so has your mother. It’s hard, especially because we are both problem solvers (read: we are crazy people) and rather social. And I’m definitely not saying to leave problems unsolved or be antisocial, it is important to be in those modes during your day-to-day life. There is a time and a place to move fast.

The mistake I see a lot of people making, and that I’ve made a lot (and still do) in my own life is that they never stop or even slow down. As a result, because you will inherit at least some of our genes and habits from me, you will probably have a hard time slowing down too.

These are some of the techniques that I have tried, which I hope work for you. Remember son, slowing down is learned behavior. This is frustrating because it has to be learned and isn’t exactly natural. It is a blessing, however, that it can be learned.

Get Outside
The easiest way I know to slow down is to get outside. In the sun, in the rain, in the hot or cold - it doesn’t matter (but dress appropriately). Nature isn’t constrained by petty human concerns. Nature moves at its own pace. Take a walk outside for no reason other than to walk. Being in nature is incredible restorative, and fortunately incredibly slow.

I didn’t realize this in my adult life until the first camping trip with Uncle Jeff and Uncle Ellis a few months after I graduated college. We were in the high peaks region of the Adirondack Mountains, and I had no idea what I was doing. They were my guides.

There’s a moment I distinctly remember during that adventure, it was probably about 20-30 minutes into our hike and something happened that I had never experienced before - I couldn’t hear any cars. Until I was over 20 years old, I had never been far away from civilization to not hear cars or the traces of other people!

Even now, as I write this letter to you, sitting on the couch in the family room of our home, in one of the quietest negihrboods in the city, before 9am on the Saturday of a holiday weekend - your mom and Riley are both sleeping. But I still hear noises. The occasional car passing by, or the dull hum of the refrigerator or electtronics equipment that is always on. Almost anywhere you go on a day-to-day basis will have some noise produced by humans, especially when you’re inside. All those noises make it hard for me to break from being in problem solving mode or social mode.

Getting outside, whether it’s deep into the backcountry of a place relatively untouched by humans or a park in the middle of a city - like Belle Isle or Central Park in New York, or even just the sideway of our neighborhood on a sleepy Saturday morning - getting outside is one way you can slow down and reopen yourself to a mindset of curiosity.

Schedule Unscheduled Time
Before your mother and I were married, one of the challenges we had to overcome was that we burned ourselves out by over scheduling our lives. We rarely felt relaxed because we were always on the move. All our time was scheduled as “fast time” - where we were doing some sort of activity - dinner, socializing, volunteering, working, or something cut from that busy sort of cloth. Our lives were filled with time for which we couldn’t set the pace. What we tried first was saying we needed to schedule fewer things. And so we left our calendar open more.

That approach quickly failed because last minute plans come up, a lot, especially when you’re young. And when those plans sound fun, and you like who proposed them, and your calendar isn’t full, it’s easy to say yes. I’m that way, especially. Last minute plans are like potato chips to me - I can’t turn them down, even though I know they’ll make me feel sluggish the next day. Like potato chips, when a plan to socialize is in front of me, I can’t say no.

Seeing as how our “keep the calendar free” idea wasn’t really working, we tried the opposite. We started actively scheduling “slow time” instead of keeping the calendar free. Around the time we were engaged, we started calling this practice “Black-out Day.”

The idea was simple. We picked one night a week where scheduled time to have no other plans. We called it black-out day because we blacked out our calendar. Doing this made us much more likely to have slow time. It’s not a perfect solution, but it helped.

What’s important to remember about slow time, is that it’s not a time to “catch-up.” Don’t use it to catch up on work or catch up on e-mails, or “be productive.” Use it to rest and decompress - the time isn’t really worth it if you don’t actually slow down.

If you need to, do something that requires you to create something or express yourself. Write something. Bake a pie. Talk to your mother and me. Sing. All these things are great and force a slow tempo.

Take Real Vacations
If you read this while you’re still in middle or high school, you may think this is obvious, but it’s not. Taking a real vacation is not easy. Work and ambition get in the way.

When I was a management consultant, I had a surprising amount of vacation days, about 25 days in a year, I think. But I often wouldn’t use it. That’s step one. You have to prioritize vacation enough to actually take it.

When you are working a job, there will be times you think you can’t take a vacation. This probably means, however, that you’re caught in the trap of thinking your work is more important than your health, your life, and your family. Or, it means you haven’t prepared your team well enough to function without you.

When you are actually on vacation, you actually have to be there. As in, actually on vacation and actually not working. Leave your computer at home if you can. Don’t check your messages and communication tools. That is one of the reasons why I like to vacation in nature, in the middle of a National Park, it’s often impossible to be reached because there aren’t telecommunications signals available (at least not in the 2010s). And as I said previously, nature goes at its own pace, no matter what you do.

The most important aspect of taking a real vacation is freeing your mind from thinking about work. When your job is stressful (and all are in their own ways if you let them be, I suppose) you actually have to observe your own thoughts and let those thoughts leave your consciousness, so you can clear your mind for vacation. Remember, those vacation days are part of your employment contract, so use them. You’re giving money away if you don't.

In recent years, I’ve tried to apply this thinking to any day off, including weekends. Weekends, in a way, are two-day vacations that you get every week. It’s nice to treat them that way as much as you can.

When your mom and I look back at our childhoods, what we reminisce about and remember fondly are the vacations we took with our families. For your mom, it was trips like those she took to Myrtle Beach or Up North. For me it was going to India, Orlando, or New York. We both remember trips to Disney, which we will take you to, soon.

Those trips were the uninterrupted times we had with our families. Those are the times where relationships and bonds were formed - not the surface level ones, but the deep ones. And these memories, whether it’s 14-day vacations or 2-day ones that we get once a week are the ones that your mom and I can’t wait to have with you and the rest of our family and friends.

Love,
Your Papa

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If you’re interested in reading more of the Choosing Goodness project, I’d love to send you a quick e-letter when I share additions. Please leave me your contact information and I’ll be sure to keep you posted.

To see all the posts in this series, click here.

5: Curiosity

May 7, 2017

This is my third attempt trying to share with you why I think curiousity matters so much for goodness (hopefully I’ll be persuasive and you’ll agree - and you’ll have more ideas to bring to the matter than your old pops does). But now that I’ve noticed the difficulty, it makes sense that I would have a hard time explaining why curiousity matters - I can’t remember a time when I wasn’t curious. It’s hard to explain curiosity because it is water to me.

When I learn something new, or an explore an idea by reading, or by asking someone some more expert than me a question, I get such a satisfying feeling. It even makes my skin tingle sometimes. In a way it’s a relief, like the feeling of icy cold water, the second it hits a summer’s parched tongue. It’s exciting like finding a secret passageway for the first time. It’s like finding a distant cairn on a difficult trail, signaling that we are one step closer at knowing the truth. It’s a feeling of connection to many millions of people, both alive and gone ahead, that learned what you learned and explored the idea you just explored.

But most of all, these days, learning something new makes me feel echoes of your Dada. Learning, to him, was such a delight. He insisted upon it. And he brought tremendous intensity to learning. In retrospect, learning is when he was freest, and most himself. He loved it.

That exhilaration for learning is something he passed to me, and I to you. Writing this letter to you about curiosity unexpectedly reminds me of his sincerity, warmth, and honesty. I miss him, and I hope sharing these thoughts on curiosity are something he would be proud of.

Learning is a special craft for your Granddad, too. When your mother and her siblings were growing up, he would always say , “learn something new, do something special” before school every day. But I’ll let your mother tell you more about that. It’s a very special memory of hers.

But let’s focus and turn to curiosity and it’s relationship to choosing goodness. We lay our scene in the kitchen.

Let’s say you want to become a great cook. Not a professional chef, but a great cook nonetheless. So you figure, you’ll cook something. You know what you’ve eaten before and you’ve seen your mother and I make meals in our kitchen at home, so you know at least something about cooking - some of the smells, that burnt food tastes bad, food flavor combinations you like. You know things like this.

Since you don’t have much experience in the kitchen, you decide to make something simple - macaroni and cheese. But if you only know what you know about macaroni and cheese based on what you’ve eaten before, where do you begin? Where do you get ingredients? You’d have to know about grocery stores. And you’d have to know something about cheeses and pasta, generally, to be able to choose what you want when you get there.

Once you bought ingredients, you’d have to know whether to use a stove or a microwave and how to operate each one. You’d have to know what pots and pans to use. On top of all that, youd have to know how much macaroni and how much cheese to combine. And all that for such a simple dish!

And lets say you figured that you could hardly consider yourself a great cook as the dish is not that complicated, nor is it nutritious. To be a better cook, you’d have to learn more dishes, fundamental skills, and practice a lot. You’d have to learn about the stove, oven, knives, and other tools. You’d have to learn to use your senses. After that, you’d be a decent cook.

But a great cook? That would still take you another level of learning. Great cooks know about more than just cooking. They know about chemistry, and why different substances interact the way they do at different temperatures. They understand the physics behind heating, cooling, pressure, and the properties of solids, liquids, and gases. They understand nutrition and how food affects health. They understand history, culture, and customs related to how people eat. They even understand something about art and design and are particular in how food is presented. Great cooks probably know a thing or two about planning and operations, too.

To be a great cook, there is so much to learn, and not just related to the most obvious elements of cooking, but across many diciplines and traditions. It takes time and is hard work. It certainly doesn’t happen overnight.

The reason why I bring up trying to be a great cook is that trying to choose goodness functions in the same way. You have to learn so many truths from peripheral disciplines, same as cooking. You have to practice, just like cooking. You have to start with the basics, just like cooking. It takes years to get there, just like cooking. It’s really hard, just like cooking. You won’t be paid or compensated for your efforts, just like cooking.

So why would anyone want to learn how to be a great cook? Afterall, it’s really quite a commitment. Being a great cook, especially because we’re not considering professional chefs who are paid for their work, requires a willingness and motivation to learn.

That raises a very interesting, essential, and fundamental question: what motivates someone to learn? If we can answer this question, we will learn something about what may motivate someone to learn to choose goodness over power, too.

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There is a theory from the social sciences that is helpful here - intrinsic and extrinsic motivation. The idea is, there are two basic types of motivations. Intrinsic motivation is motivation that comes from the happiness, joy, or meaning you get from the task itself. Extrinsic motivation, on the other hand, is the motivation that comes from earning a reward or benefit that comes from the external world.

With learning and discovering what it means to choose goodness, just like in our example with cooking, there is no extrinsic reward coming. There is no pot of money for learning to be a good person. being a good person. There is no prize or daily recognition that comes with learning to be a good person. being a good person. There is no certificate nor medal for learning to do the right thing. When it comes to learning to choose goodness, there is no extrinsic reward that exists that I can of or have ever seen. I find it even slightly uncomfortable to think about rewarding someone for learning what it means to choose goodness - it feels ideologically inconsistent.

The saying “good things happen to good people” is probably true. But that’s hardly an extrinsic motivator, realistically speaking, because the time between when you learn and when you receive the benefit of the good thing happening to you is so far away, its not really present in your mind when you’re learning.

So when it comes to learning how to cook, learning to choose goodness, or learning just about anything on your own you have to be intrinsically  motivated, because that’s the only type of motivation that you actually have the option of tapping into. Put another way, you have to find pleasure or interest in the act of learning itself, because you will receive no external reward for engaging in that learning.

This is where curiosity comes in. I told you earlier about how much I enjoy and find pleasure in discovering something new. I hadn’t thought of it quite like this until just now, but that pleasure comes because my curiosity is satiated by learning. Curiosity almost creates this very exciting gentle tension, which is resolved satisfyingly by learning.

In a way, learning isn’t as pleasurable unless you have that curiosity putting just a little bit of tension and anticipation into the mix. Because without the curiosity, you can’t get the pleasure of satisfying your curiosity after engaging in learning. Just like a joke can’t have a funny punchline without a setup, learning can’t have the intrinsic satisfaction without curiosity. Just like the Temptation and the Hawaiian War Chant, you can’t have one without the other (you’ll get that joke later in life, it’s a University of Michigan Marching Band reference).

That is why curiosity is the first capability of choosing goodness, without curiosity there is no foundation for the intrinsic motivation needed to learn on your own, and in turn discover goodness over the course of your lifetime.

If you decide that choosing goodness over power matters to you, and that you want to learn to choose it, you must know what it is. You have to understand goodness to choose it.

But as I’ve mentioned already, goodness and an understanding of it doesn’t grow on trees. You’re not born with that knowledge at birth, you have to go figure it out, you have to earn it and learn it. And therefore, you must want to learn it.

That willingingness and desire to learn is what you need to discover goodness for yourself. And that willingness have to be strong and enduring, because the path of goodness is hard more often than it’s easy - as I’ve told you - it can get messy and complicated.

Genuine curiousity is the strongest creator of motivation to learn that I’ve ever come across, and it’s the only motivation to learn I’ve ever seen that actually lasts. That’s why I think curiosity is so important and crucial to discovering goodness - staying the course toward goodness takes an abnormal amount of motivation because it is very hard to learn, takes really long, and comes without any extrinsic rewards. Curiosity is my best answer on where that abnormal amount of motivation comes from.

Certainly, I hope you are curious the world and the real causes and effects you see in how it works. And I hope you are curious about God, too. I hope you are curious about history, science, music, politics, physchology, management, mathaematics, and so many other things. I hope you are able to explore people, places, planets, and philosophies beyond your own. I wish for you a life of voracious learning and discovery.

But if you’re only curious about the world around you, you’ll be missing something important - yourself. You need to be curious about whether YOU are a good person, because you won’t always be. To choose goodness, you need to want to know the truth not just about the world around you, but also the truth about yourself. This act of self-examination is crucially important, and we’ll get to that more later.

By now, I hope the question you’re asking, is, “well Papa, how do I become curious?” And that’s what we’ll turn to now, all the best ideas, stories, and learnings I’ve had about how to cultivate and nurture the curiosity within us.

I’m so excited to share this with you and talk about it with you someday. Let’s begin.

Love,
Your Papa

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If you’re interested in reading more of the Choosing Goodness project, I’d love to send you a quick e-letter when I share additions. Please leave me your contact information and I’ll be sure to keep you posted.

To see all the posts in this series, click here.