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