Asking Better Questions: How Instead of What

When talking to a person I admire, I love to ask what they do each day. What do they do at the gym? What do they eat for breakfast? What is their evening routine? What do they wear? I’ve always thought, if I do what the person I admire does, then I can be just like them.

When I learned that Mr. Rogers swam one mile every day, I eagerly jumped in the pool and started counting laps. When I learned that John Steinbeck wrote East of Eden with Blackwing pencils, I started writing with Blackwing pencils. It was as if I could become who I admired by simply mimicking what they did.

This doesn’t feel true to me now. Instead, I think we learn from others by studying how they process the world and make decisions based on that processing.  

The better questions are about the how, not the what. How do they think through approaching exercise and how did they end up choosing the routine they did? How do they think about what and when to eat? How do they relate to sleep, if at all?

You cannot become Lebron James by purchasing a hoodie he wore, even though I did exactly that a few weeks ago. In fact, you cannot become anyone else at all. That person is already taken.

No one has the same approach and view of the world as you do. And embracing that difference while refining you own process is the key to becoming a person you would admire. What you can learn from others is how they have related to their own processing. Asking “how” questions helps you better understand your own operating system.

The “how” of what you do is where the good stuff is. The “what” of what you do is just the by-product.

The Pause

Anyone who knows me knows that I like to talk. And I’ll admit it: I often talk too much. I may understand the adage two ears, one mouth, but there is a reason why I still need the reminder. Over time, I’ve seen how my tendency to jump in has affected others, and it’s not always great.

Which is why I love the Pause.

The Pause is a five-second inhale and exhale you take after the other person finishes talking. Simple concept, wonderful results. Three quick benefits:

1) The Pause gives the other person an opportunity to get at the deeper thoughts they have in their mind. In the normal ping-pong of a conversation, the deeper stuff can’t always find a way to jump in. The Pause gives the other person a chance to dig at the richness of thought that lies below niceties and surface-level conversation. The next comment or question they ask will be more thoughtful.

2) The Pause helps you reset before you start talking. It’s the “ready, set” before the “go” of your next statement. The precious breath gives oxygen to the lungs and time for your unconscious to process what they just said.

3) The Pause helps you connect with the other person. If music is the space between the notes, connection is the space between the words. People respect when you take in what they say. While five seconds may feel like an eternity while you’re doing it, there’s no awkwardness in receiving the Pause. It’s natural and will be appreciated.

My Five Favorite Movies I Saw In 2020

Mulholland Drive (2001): An aspiring actress experiences the hope and despair of Hollywood in a haunting fever dream that could only come from David Lynch.

This nightmare puzzle box dazzles and lingers in elliptical scenes that are perfectly sensory and non-sensical. The movie imprints a feeling of unease that only an unshakeable night terror can. A motion picture in the purest sense, the images of the movie are the paintings in a museum you may never return to but will never forget. Diners will never be the same.

First Reformed (2017): A reverend haunted by the loss of his son and the dissolution of his marriage talks with a climate activist, who sets him on a journey of inner reckoning. Will God forgive us for what we have done to this world?

This stunning thriller is about the rage and faith within us all. Filmed with simple sets and austere scenery, the inner stakes are raised to ceiling-shattering levels as questions of purpose, spirituality, and sacrifice envelop each frame. What if everything we thought was true was wrong? What if we were the only ones to know? Am I the crazed or the crazy?

45 Years (2015): A husband discovers that his former lover’s body has finally been found. And 45 years of marriage may crumble because of it.

This movie explores the horrifying questions that linger in any relationship: What if the person I love is a person I never knew? What if my love was built on a story that I told myself? Each scene builds as the quiet terror of a world crashing builds to a surprising fever pitch. The last scene is my favorite ending to any movie I have ever seen.

A Coal Miner’s Daughter (1980): Loretta Lynn leaves home at age 15 with nothing but her voice and a domineering husband, Doolittle. She’ll always be a coal miner’s daughter, but will she ever grow to be more?

The movie rises above the central limitation with biopics: that the movie cannot live up to the larger-than-life people they attempt to honor. This movie is the rare example of the facsimile being not only as good as the original but a distinct and unique piece of art itself. A biopic worthy of a biopic.

A River Runs Through It (1992): A man reflects on his upbringing in Montana and his relationships with family.

The “what” of the movie is straightforward and beside the point. What shines instead is the hypnotic scenery of Montana, the assured acting of the leads, and the stunning shots of fly fishing in action. While hard to describe, the movie is viscerally memorable, describing the distance and proximity between us and those we love the most. As the father reflects upon in his last sermon, we may not understand the people we love, but we love them still.  

The Tao of Star Wars

I’m a few decades late, but I finally finished watching the original Star Wars trilogy. I’ve also been reading a translation of the Tao Te Ching and couldn’t help but notice how the films illuminate a subtle concept from the philosophy: weakness over strength.

I’m fascinated by the strength of weak things, how weakness that flows can be stronger than strength that is rigid. The palm tree sways with the wind and stays standing as the tough oak tree falls. The water nourishes the roots in soil that a shovel could never penetrate. Passivity is not passive. Weakness is not weak. Strength is not strong.

The supreme good is like water
Which nourishes all things without trying to.
It is content with the low places that people disdain.
Thus it is like the Tao.

Chapter 8, Tao Te Ching. Translation by Stephen Mitchell

At the end of Star Wars: Return of the Jedi, Luke defeats the Empire not through his lightsaber and X-Wing, but through weakness. Only when he tosses his weapon aside and lets Emperor Palpatine repeatedly electrocute him without reaction does he awaken the humanity inside his father, Darth Vader. Vader’s humanity had remained hidden for the entire trilogy, as Luke attacked, reacted, and fought back repeatedly. Luke won by allowing the evil of the Empire to be as clear and reflective through their actions as possible. He held up a mirror to his father, and Darth Vader saw the evil for himself. Luke did not give up or get cynical or give into nihilism either. His non-action was active. “I’ll never turn to the dark side.” It was a conscious choice that telegraphed to his father: look at what you condone, look at who you are. That wasn’t reactive, cowardly, or resentful. That was true power.

Practice not-doing,
And everything will fall into place.

Chapter 3, Tao Te Ching. Translation by Stephen Mitchell

Often, restraining our strength is powerful. Force of will may not reflect the will of the Force. Listen, don’t talk. Flow, don’t react.

On Helping Loved Ones

I think most of us have experienced the ease of advising a work colleague or acquaintance and the difficulty of helping a close friend or family member. What a strange paradox. Parents: “I tell my child to do something, and they choose to do the exact opposite. I don’t get it.” Close friends: “I tell X that she should break up with Y, but she just won’t listen. It’s like talking to a wall.” These conversations can feel defeating to us, an indictment on our worthiness as a friend and confidant. And the truth that we cannot control what others do eludes us when it comes to those that we love the most. Easy it is to accept the poor choices of a work colleague, but difficult to accept a sibling with different beliefs from your own. With those we don’t love deeply, influence appears easy. Advice can be honest, accepted, acted upon. Truth may be effective.

With loved ones, there’s more going on. Your loved ones and you are engaged in a relationship that supersedes individual actions and choices if that bond is unconditional.

So, the game we must play is not about being right but about being effective. And being effective requires embodying exactly where they are without judgment, and presenting the thing they need in the moment. This does not guarantee the results we want by any means. This just means that the outcome we hope for is slightly more likely to happen. And from there, we live with the results.

Your advice to a friend that exercise will help their mental state may be correct. You may have science, psychology, and personal experience on your side. But depending on where they are, it may not be effective, or worse, may make matters worse in the long run. If they are unprepared, try, and fail, they may never try it again and feel worse for disappointing you. Influence is a flowing act. We may agree upon universal tenants, like “be kind, respect yourself, treat them how you’d like to be treated,” but the packaging needs to be tailor made.

I listened to an interview with actor and singer Jaime Foxx recently, where you talked about his foundational relationship with his grandmother. He talked about how she saw her role as the bow, and him as the arrow. Influence of loved ones is an elegant dance of aiming without control. We can aim our loved ones in a certain direction, but try too hard, and we miss the mark completely or become disappointed with the inevitable difference of where they land. All you can do is pull back, let go, and hope they are closer to the target than where they started.

Yesterday, I saw the expansive, epochal film, “The River Runs Through It,” about a professor who reflects upon his upbringing in Montana with his preacher father, devoted mother, and larger-than-life brother. At the end of the movie, his father closes with a moving sermon on an approach to loved ones. The paradoxical bind we feel of being so close, yet so far.

“Each one of here today will at one time in our lives look upon a loved one who is in need and ask the same question: We are willing help, Lord, but what, if anything, is needed? For it is true we can seldom help those closest to us. Either we don’t know what part of ourselves to give or, more often than not, the part we have to give is not wanted. And so it those we live with and should know who elude us. But we can still love them – we can love completely without complete understanding.”

Reverend John Norman Maclean, “The River Runs Through It”

Be with your loved ones. Absorb their point of view. And when you speak, pull back, let go, and stay with them lovingly.

Habits: The What Matters Less Than The Practice

There’s no reason to intellectualize a good habit. Keep it simple.

With so much information at my fingertips, I often feel conflicted about what habits to cultivate, what skills to develop. Whether it’s deciding what to eat or what exercise regimen to adopt, I have a tendency to read all the literature, watch all the reviews, and think about the optimal solution. But after the joy of these deep-dives passes, decision fatigue and paradox of choice set in. I’ve avoided the real work. The what matters less than the practice.

For about a decade, I read about meditation. I felt the dopamine hit of having the conceptual understanding of why it was good for me. I had something to talk about with friends. I had a certified-fresh piece of advice I could bestow upon others. But I avoided the simpler, more important thing: sitting down, closing my eyes, and actually meditating. The shift to practicing has provided far more for my soul than talking about and researching it ever did. Reading, watching, consuming content about habits feels good. But that feeling is like a knock-off two-dimensional screengrab of how you feel when you do the thing. Knowledge is conceptual and fleeting. Wisdom is experiential and eternal.

But my brain likes the intellectual rumination, It’s safer. No failure, no struggle, no judgment. But also, no risk and less reward. When I avoid the work, I miss the high highs (and low lows) that come with the practice. The simple act of practicing a habit is plenty difficult in itself. And it stimulates the soul in a far deeper way.

Learning about habits is like seeing an amazing magic trick and learning how to do it. The act of learning a magic trick is difficult. It requires research, repeated viewings, and careful analysis. For example, a 10-year-old would have a hard time replicating a David Blaine slight of hand. And afterwards, there’s a certain satisfaction in knowing what the magician is doing, seeing the misdirection while it’s happening. You may even be able to replicate the trick to a friend after some time. But the practice of doing a magic trick once you know how is simple. There’s a certain emptiness that sets in once you’ve figured it out. The challenge is over. Time to move on to the next knowledge domain.

Doing a habit is more like learning to play chess. The rules around how to do it can be explained in a minute. But the mastery of the craft will take years, even though each game starts out identical to the last. The act of playing chess is simple. A 10-year-old can learn. The practice of doing it is difficult. But the practice is the whole point. There’s a feeling that is hard to talk and write about. You can improve through a better conceptual understanding, but the wisdom only comes through doing it.

The elegance of a habit is in its simplicity. So don’t intellectualize whatever you choose to do or stop, whether journaling or avoiding junk food. Treat your brain like you would a child. Keep it simple, have rules, create boundaries. It’s easy to criticize the person who says, “oh I don’t eat pizza.” The arbitrary line-drawing, the flawed reasoning. But while the statement appears absurd, if I stopped eating pizza, I’d be a much healthier person. So for me, what’s more important that the habit itself, is the act of doing it. The consistent practice. Pick something, anything. What’s far more important is the experience. Deciding where to go matters less than the steps, miles, and calories you spend getting there. Give your mind a break, and keep it simple.

Five Tips On Leaving A Great Voicemail (The Case Against “Hey, Call Me Back.”)

  1. Include the who, what, and how. Who are you? Don’t assume the person remembers who you are, especially in service industries where the receiver may get 100 calls a day. Starting the call with your name is critical for giving the listener a starting point to orient themselves to the situation. What are you calling about? Only saying, “hey, call me back” is frustrating for the person trying to help because they don’t have context. If there was a prior conversation, remind them what was discussed. And ask a question or say exactly what you want done. This gives the operator, service provider, or friend a chance to prepare for the next interaction. How do you want them to call back? Leaving a call back number or email address is important because there’s no guarantee that they know how to reach you. If the other person has 10 missed calls and 17 voicemails, it can be hard to sort out the phone number, or at least creates additional work.
  2. Pause after sentences, names, and numbers. Taking down notes from voicemails is hard to do. People often talk fast. Collapsing sentences with critical information makes it hard for person on the other line to write it all down. So many times I’ve transcribed voicemails but missed critical details like the name and number because the person rushed to the next sentence. “Call me back at 1234567890mynameisjimgivemeacallokthanksbye” makes the name and phone number so hard to remember. So…
  3. Say numbers in groups of 2 or 3. The dashes in phone numbers are useful not just for reading, but for talking and listening too. Saying the phone number in small bunches like 123-456-78-90 makes the other person’s job so much easier. Success is having the other person not have to replay your message.
  4. Spell your first and last name. In service industries, logs are often kept for call histories. Having an exact match for your name is helpful not just for facilitating whatever you need help with but also ensuring that future communication goes smoothly.
  5. If there’s something wrong in the person’s voicemail greeting, tell them. The person who makes the voicemail greeting will never hear it again, unless they call themselves, which I’ve never done. This means that an old out-of-office vacation greeting message may remain for months or years afterwards. No one wants that. Let them know. It wasn’t left on purpose.

On the Ending of The Sopranos

I finally did it. I finished The Sopranos.

Over nine months and eighty-six episodes, I watched The Sopranos awestruck and horrified. And this weekend, I watched with curiosity at how I would react to the infamous last scene. The diner. Don’t Stop Believin’. The cut to black. The big question: does Tony Soprano live?

Having finished, what I feel certain of is this: the question misses the entire point entirely. It doesn’t matter whether he lives or dies in the diner. The ambiguity is the purpose. Life happens to us. It seems random, complicated, and occasionally cruel. The meaning of it does not stem from the resume of events A through Z. The meaning is from our examination of our internal purpose and our sense of how to live a good life.

What I loved the most about the show is that it’s not spoilable. To be precise, I mean that knowing what happens does not affect the enjoyment of what you see on screen. What happens is besides the point. For example, great things can happen. Tony can survive a bullet wound, Carmela can feel artistically moved in Paris. Christopher can get his movie produced. But without an inner compass, these fleeting moments inevitably pass and resentment at the monotonous milieu sets in. Life gets boring again. Buying, gambling, conquering, killing, controlling feel needed to mask the untamed internal chaos and guilt. Whether through repeated plot points, dream sequences, and elliptical therapy sessions, the creators tell us over and over again: look at the spiritual flame of these characters and see how it dims.

Whether Tony Soprano dies is besides the point because he and the characters of The Sopranos have already experienced a spiritual death and choose to remain there. They’ve resigned themselves to a false steady state where the center, as Keats said, cannot hold. While Tony has bested everyone at the table, but he knows he cannot cash in his chips.

Our reaction to the ending says nothing about what happens to Tony and everything about our relationship to the events in our own lives. When the show cuts to black, it’s us we see on that blank screen. The story of the Sopranos has ended. We’ve seen how not to live a life.

Now, what will we do?

The Problem is the Solution

There’s nothing more natural than being quick to judge others, especially when they make a mistake or do something we don’t approve of. How could you do this?! What were you thinking!? This is all your fault!

But behind every frustrating act is an opportunity to learn.

If you’re a deli owner, and you see a crowd of people bunched up at the check-out area, it’s easy to judge them for not forming a straight line. Or you can see this as evidence that your store was unclear about where to stand. The customers are pointing out what you need to improve, whether it’s marking the floor or changing the checkout location.

If you’re a lawyer and a client isn’t listening to you, you can yell at them for being irrational and foolish. But the client is really telling you to speak more clearly. Behavior that causes anger and frustration is not evidence of something wrong, it’s pointing to something right — a solution hiding in plain sight.

The truth is this: everyone does things for a reason. We can either judge them for that or take it as an opportunity to learn and empathize.

Actions that offend us are often solutions to deeper problems.

Take drugs or alcohol. For many, drugs are not the problem. Using is a solution to a deeper problem for which a temporary high may appear to be the only answer. The solution is no doubt imperfect, but simply criticizing the behavior masks vital lessons for addressing the root cause problems, like depression or joblessness.

Take sleepy teenagers. Teenagers who miss the school bus because they slept through their alarms are easy to paint as lazy. But they’re not. Their bodies are properly responding to something they need more than anything: sleep. Sleep is critical and their craving for more is healthy to functioning well intellectually. Many teenagers snooze their alarms, sleep during first period, and nod off in math class. Calling them lazy feels natural, but it doesn’t help. This “problem” holds solutions to the real root issues, like changing the school day or norms around napping.

It’s easier to get mad than to get curious. But I’m learning to hold my tongue and think, how interesting, the world is telling me something.