Letters to my sons
A collection of thoughts and lessons I've learned along the way for my little men, and anyone else that's interested.
Posts tagged with #Introspection
My sons,
It has been said that the most important thing one can do in one’s life is to communicate. We are a social species, a communal people. We were made for community and for communion. From the moment of birth we reach for connection with those around us. From our first breath we spend an inordinate amount of energy learning to relate, to connect, to be understood, and to understand.
If that’s true, why is it that so many of us communicate poorly? Why do we go through life feeling unheard and misunderstood? And why, oh why, do our best attempts at expressing ourselves often have disastrous results? Whether personal or professional, with friends or with colleagues, communicating about our personal hopes or our career goals, we often fail to convey our thoughts and feelings in a way that produces more understanding and connection.
Why is that?
It turns out that communicating is a skill. Not only that, but it is a difficult skill to master! It, like every other skill, requires practice, instruction, correction, dedication, and effort. And like every other learned skill, it can come with failures that are often painful, personal, and potentially very public.
But it is a skill that, with the right attention and instruction, can be mastered like every other.
I’ve been a snowboarder much of my adult life, but recently I’ve decided to try my hand at skiing. Call it a mid-life crisis desire to connect more with my children (skiing feels more multi-generational), call it a desire to be lazier (skiing also feels less effortful), or even call it vanity (skiing seems to be on the rise again, and snowboarding seems to have petered out after the Shawn White years); whatever the reason, I’ve taken up skiing. And man does it hurt. It feels like three steps forward, one major yard sale backwards.
But I know I’m learning. I know I’m making forward progress. Painful as it is, I can tangibly feel the improvement after each outing. My muscles are a little less sore, my instincts a little less fried, my attention span a little less taxed. These are all signs that my body is building a new skillset and incorporating and assimilating it into its ethos. I am a skier. Or dammit, at least I will be a skier. Someday.
The same is true of communicating. Many of us tell ourselves that we’re not that good at communicating, that we’re private people, that we leave the flu-flu stuff to the artsy types. But deep down, we long to be understood. Deep down, in places where we’re not ready to admit even to ourselves, we yearn for connection, to know, and to be known, to love, and to be loved as we are.
So how do we get better at communicating? How can we develop these skills so that we too can find our identities as communicators?
We’ll talk about this in three parts: 1. knowing yourself, 2. knowing who you’re communicating with, and 3. building and practicing your personal communication style.
Know thyself
First and foremost, we need to know ourselves. We need to know our proclivities, our preferences, and our blind spots. Communication is a two-way street, and if we want to successfully navigate those streets, we’ve got to understand the role that we play in the communication process. This begins with knowing our values, our triggers, and our style.
There’s a lovely quote I read once that speaks volumes here:
”We do not see things as they are; we see things as we are” - Anais Nin
In order to understand ourselves, our biases, and our points of view as we communicate, we need to be aware of the fact that the world is not as we see it! We see things through our own perspectives, through our experiences, through how we respond to those experiences. It therefore behooves us to understand how these perspectives are formed!
Some of this is work for the therapist’s office, and I won’t pretend to know enough to walk through that. But let me share a few things that have helped me along the way.
1. Understand how our experiences shape us
We all see the world with our own unique perspectives. These perspectives are influenced by two major factors: our mood, and our experiences.
The preeminent filter is our mood - when we are not in a calm and collected mood, every input that we receive gets strongly tainted with it. When we are sad, every input is dampened. When we are excited, every input is amplified.
Recently, my little guy has been using the phrase “me no happy” a bunch - partly as a cutesy way to express himself, but also partly as a way to communicate something that he’s unhappy about. Our bedtime routine has us each sharing three things that we’re thankful for that day, but his unhappy mood made each thing he said tainted with sadness. He had nothing to be thankful for that day, and declared that he didn’t enjoy any of it. After a good night’s sleep (of ~10 hours), he completely changed his tune and happily proclaimed that yesterday was an awesome day because of the 15 things that we had done together as a family.
This is the impact of our mood - it is the lens by which we interpret our inputs from the world. While not entirely controllable, our mood is certainly steerable. The factors immediately in our control are things such as the length and quality of our sleep, our diet and nutrition, and the amount and regularity of our physical exercise. Do we get the requisite 8 hours a night of sleep? Are we eating healthy and with moderation? Are we regularly engaging in physical activity that raises our heart rate and releases endorphins?
Then there are the factors that, while still in our control, aren’t as immediate. Things like the amount of stress we have in our lives, the environments that we place ourselves in, and the quality and security of our social connections are all factors that strongly influence our mood.
Next, our experiences. In his essay “Texts and Pretexts”, Aldous Huxley wrote that
“Experience is not what happens to you, but rather what you do with what happens to you”.
Each event that happens to us is a neutral event in and of itself, but take that event, filter it through our mood, and add a response to it and you’ve got an experience. This is why two people can be present for the same event and experience it so differently! One person may be in a pensive mood and, combined with their predisposition may choose to respond positively to an event while another may have a very different response. These responses create an experience that our minds store up and accumulate. Over time, these experiences shape our perspective and become a critical part of our decision making process, and by extension our communication process.
2. Know what we gravitate towards
We all have biases. Some of these are natural, evolutionary biases engrained in our species over centuries. Some of these are cultural biases reinforced by our experiences and our environment. Some of these are personal biases shaped by the inputs and our responses to those inputs over the years that have elevated to the realm of character.
All of these strongly influence the things that we gravitate towards; the subjects we find interesting, the ideals we are inspired by, the values we desire to emanate, and the style of communication that we prefer.
It is a fool’s errand to attempt to eliminate our biases. Rather, we should accept them, analyze them, and be acutely aware of how they influence us so that when we communicate with others we can be sensitive to their impact. A helpful exercise here is to regularly reflect on our experiences and to note (or take note of) biases and trends in our responses so that we can form a holistic picture of our biases.
3. Learn how to detect our blind spots
Lastly, we all have blind spots. Whether these are technical (ie things we don’t have the knowledge about), emotional (ie feelings we haven’t fully developed yet), mental (ie ideas we haven’t fully fleshed out, learned about, and considered), or spiritual (ie pertaining to the metaphysical, spiritual, and mystical realms), we all have many blind spots and gaps.
These blind spots end up impacting our communication in a generally negative fashion. At best they can create an awkward moment; at worst they can greatly impact our credibility and hence our ability to communicate effectively in the future.
A couple quick notes on how to detect these:
- Be careful about strong opinions. When you find yourself expressing a strong opinion, check yourself. Strong opinions tend to be emotionally based, instead of being rational and knowledge based, and as such are generally indicators of a gap.
- Check your defenses. Being defensive is another sign that there might be a gap. Especially when we’re not being attacked, things that trigger defensive responses are usually signs that we haven’t vulnerably fleshed out the topic and therefore have a gap there.
- Listen to your believable people. Believable people are people who have proven track record of being right about a specific area. When they point out things in your life, listen to them!
Good communication requires deep understanding of the topic, the context, and the parties involved. The more work we do to understand ourselves and how we show up the more impact we’ll end up being able to have on the outcome of our communicative interactions!
My sons,
It has been said that life is a series of moments. These moments can vary across many dimensions. They may vary in duration, in intensity, in importance, and in their impact on the overall trajectory of our lives. But it is these moments, strung together with some invisible string, that guide us, that give us meaning and purpose, and that ultimately define who we are and who we will become.
When we take the time to look back and be introspective about the strings of moments in our lives, we often discover that there were some moments that seemed more important than others, more prominent in our memory. They may not have seemed important at the time, or may even in retrospect be small or unremarkable, yet they nonetheless are critical moments that we remember as having some strong impact on us.
In the 2015 Pixar movie Inside Out, the writers propose the concept of core memories. These memories hold higher importance, and are memories that strongly shape our personalities and our character traits as we grow. But they don’t explore why these memories are important, why they become core memories for us.
I believe the reason is that these memories are memories of keystone moments in our lives, moments that hold strong value and have an overall greater importance than the rest. But what are these keystone moments and why do they have such a strong impact? I’ll define the following:
Keystone moments are moments that bring clarity to all the little moments along the way, causing us to introspect and compelling us to decision and action.
If it is true that our lives are indeed a string of events, a series of moments, then keystone moments are the ones that bring clarity, understanding, and unifying themes to some series of seemingly insignificant and disconnected moments along the way. They are moments that light up individual moments and allow us to see patterns and derive meaning from the otherwise endless and continuous stream of moments along our path. And they are moments that bring sharp attention and focus, compelling us to consciously examine ourselves and actively decide what path to choose next.
Very often, a keystone moment may not be immediately obvious. We may fail to notice their significance at the time of the event itself, only recognizing their significance later on. Often it is when our minds are quiet, when our hearts are at peace, and when we’ve got the head space to reflect that we then notice a significant moment has occurred.
At first glance, these moments may not seem significant - a note from a friend, a feeling of peace after a storm, opening your first piece of mail at your own home - but in context, they become incredibly important. They allow us to elevate our thinking, to see our lives in perspective, and to step back and look at the big picture. Perhaps the note came at the end of a long series of struggles and conflicts, the peace was hard fought through a long stormy period, the mail symbolized your first touch of freedom. Regardless of the context, these moments are the culmination of a set of experiences that have deeply impacted us.
Keystone moments cause us to introspect and evaluate
A trademark of a keystone moment in the making is that when it happens, we are compelled to introspect and evaluate. Maybe you’re like me and like the dramatic and romantic thought of looking out the window at the evening city lights with a glass of scotch in your hand as you reflect, or maybe you prefer sitting in your PJs wearing your favorite robe with a warm cup of coffee on a quiet Saturday morning to think. Regardless of your choice of dramatic underscoring, keystone moments nudge us towards rumination.
These moments strike a chord with us. They are moments that reach through the veneer of everyday life and touch some deeper vein of consciousness within us, begging us to turn off the autopilot of our lives and to strongly consider the implications of what we’ve just experienced. They resonate with our core values, perhaps contradicting, perhaps amplifying, but always causing us to pause and evaluate.
keystone moments allow us to strongly pivot and change course
Some years ago, I was at yet another work conference in Vegas, staying at my favorite Vegas hotel, the Wynn. One night after some conference events, I found myself at a bar next to the casino floor with two friends, drinking and chatting way into the night. This itself is a fairly common event for me - working in Big Tech, I must have been to two or three dozen conferences in Vegas by then. This night was like many others - a couple of friends, a thinning crowd at the bar as the hours wore on, and of course, several rounds of drinks which led to deeper and more meaningful conversation. Again, nothing new.
Eventually, 5am rolled around and we all decided that we should head back to the rooms in order to make it to our 8am meeting the next morning (unsurprisingly, two of us didn’t make it), so we left the casino to escort our one friend to the hotel next door where she was staying. Walking out the front door we immediately felt tired, and attributed it to the myth that Vegas hotels pump oxygen into the casinos to keep people awake (they don’t). We all had a good laugh at that, and that was that.
Some years later as I prepared for my transition out of that company, it dawned on me - that night in Vegas was more than just our typical after-conference evening. Something about that evening that to this day I’m not perfectly clear about impacted me. For some reason, that night solidified my understanding that the thing which mattered most to me was not the work. It wasn’t the brain stretching problems, the perplexing people management puzzles, the exciting new product ideas, or even the inspiring visions for how the world ought to be, how it could be. No, the thing that mattered most to me was the people. It was the relationships. It was the friendships.
From that day onward, I changed the way I thought about my career, about the roles I was willing to take, about the team environments that I sought out. That keystone moment brought about a clarity that allowed me to pivot, to change the way I behaved and the paths that I pursued.
One of the realities of an increasingly connected world is that the strength of the current of the path expected of us gets ever stronger. With an almost nonstop scrutinization of our lives in the form of friends, social media, professional networks, and public personas, the force required for us to adjust course is almost insurmountable for most.
It often requires some large event, some crisis moment that shakes us loose and forces us to move and to pivot. Those moments are one class of keystone moments that cause us to action and give us the leverage we need to pivot.
In 2019, we had a global event that caused crisis moments for virtually every person on the planet. This global pandemic had many, many negative impacts, but for some, for the thoughtful, the intentional, and the mentally strong, it also created a flurry of keystone moments that allowed for a strong pivoting of their lives.
In the comically light hearted movie Deadpool, Colossus is trying to convince Deadpool that being a hero doesn’t mean living a life with a perfect track record. He shares:
“Four or five moments. That’s all it takes to be a hero.” - Colossus
Four or five moments. Four or five keystone moments where we pivot hard and make the hard choice to be better. That’s all it takes. I love that.
My sons,
A good friend recently recommended I read The Pathless Path by Paul Millerd, a book that describes the author’s journey in finding meaning and fulfilling purpose in his life. In the book, Millerd lays out a concept that he calls the Default Path, a blueprint for life that outlines purpose, value, and success. It is a one size fits all path that we are all expected to adhere to. He asserts that for most people, the notion that a second path exists is almost entirely unbelievable.
The Default Path, Millerd argues, is the one that our upbringing, background, social, and economic systems work together to daily reinforce. It is the model for our lives that has been imprinted and reinforced in every interaction and every experience. It is so deeply engrained, so fundamentally expected that we never stop to ask if life must in fact be led this way. And when we eventually (and, arguably, inevitably) question the path at an inflection that many have taken to calling the midlife crisis, there is such an overwhelming amount of peer pressure and societal structure to overcome that we often end up concluding that rather than being an issue with the path there is instead something wrong with us.
For North Americans, that default path often resembles what’s globally known as “The American Dream” - the belief that anyone can achieve financial and social success through hard work and dedication to that work. Images of single family homes with white picket fences, a pair of cars, a pair of kids running around with a happy spouse, and financial independence - all attained through hard (and recently updated to include meaningful) work.
Everything in our upbringing reinforces that message so strongly that most of us never stop to consider if there is another path. Legendary economist John Maynard Keynes (aka “Our Hero, Lord Keynes” to anyone who has ever had the great privilege to have taken Larry Smith’s Econ classes at Waterloo) famously said that “worldly wisdom teaches us that it is better for reputation to fail conventionally than to succeed unconventionally”.
And so we play to not lose.
We play the game of life in a way that doesn’t seek to win, doesn’t seek to conquer new horizons and be filled with awe-inspiring experiences and journeys. No, we play in a manner filled with fear of losing, fear of failing. We fear missing out on what everyone else is doing, fear being left behind by the masses moving in the direction of the inevitable path.
We feel so strongly that not only is this the right path, but it is the only path. And so, on we go, putting all our energies and resources into working harder, making more money, having more social influence, and raising children who do the same.
We play this fear-driven and defensive game with the hope of not losing for so long that we inevitably wake up one day sometime in our 30s and 40s and wonder what it was all for. We have spent the entirety of our youth and the majority of our most productive years on a path that we didn’t even set for ourselves! No wonder we come to a moment of crisis. Coined in 1965 (coincidentally a short decade or two after the beginning and wide-adoption of the 9 to 5), the midlife crisis is a recognition that we have been passive players in the direction of our lives, and this terrifies us.
A rude awakening
We wake up one day realizing that we don’t have any earthly clue what our life’s purpose should be, and that our goals to this point were not in fact our own. Worse, we are thoroughly unequipped to set meaningful goals for ourselves and define what a rich and fruitful life looks like, so we revolt. We buy sports cars. We get plastic surgery and update our wardrobes. We do any number of nonsensical things in an attempt to silence that inner voice telling us that we’re playing this game wrong. What many of us never realize until much too late in life is that there is another way to play this game, another path that we can be on.
We can play to win.
We can learn to play the game differently. We can endeavor to gain much more clarity on the rules of the game, the terms of engagement, and, most importantly, the conditions for victory.
Most people spend the majority of their lives sitting in the passenger seat, having fully assumed the role of spectator in the unfolding narrative of their life and having fully accepted that the majority of decisions are made for them. We were never told that there is another way to play, another path to victory, and another role that we can assume.
Think back to the first big decision you made in your life; the one where you felt the true gravitas of the situation. For a fair amount of us, this was the act of deciding which college to apply for, and hopefully to attend upon acceptance. Think of how that decision was made, of the inputs, the factors taken into consideration. How small a role did one’s passions play in that significant decision? How much more did we consider things like future earning potential, prestige of the school, respectability of the profession, desires of our parents, or just plain ol’ common wisdom?
Discover yourself
From that early age we were taught to make decisions by someone else’s standards. Playing to win means that we need to throw out those standards and to come up with our own. We need to first discover ourselves, to do the hard work of uncovering the things that bring us joy, that excite us and ignite the passion within us.
We need to let go of the need for external validation, the compulsion to measure against what our peers are doing. We need to remove the mental pollutants in our lives - the likes, the retweets, the perpetual feed of an abundantly glamorized default path - and instead look within for validation, for meaning. We need to learn to trust our internal compass.
Own it
And then we need to own it. Once we’ve discovered what makes us tick, what things bring us joy, what types of people we desire to become, we need to unapologetically own it.
One of my great mentors told me once long ago that as a society we have become so focused on the next big thing - the next promotion, the next million users of our product, the next milestone in our children’s lives - that we forget to think about the people that we are becoming. We get so wrapped up in impressing someone else that we forget about what it does to our character, our morals, and our decision making framework. If left unchecked, we become like the environment we place ourselves in.
So we need to own it. We need to own how we show up at work, what we’re willing to do based on our boss’ orders or company expectations, and how we determine what a successful time in our place of employment looks like. We need to own what we work out with our children to actually be the best for them, and not what all their peers happen to be enrolled in. We need to own what traits in a partner make us happy, whole, healthy, and growing human beings, regardless of their social standing or their pedigree.
Playing to win means playing by your own standards, and not conforming to the expectations of the world. It means being okay with walking off the beaten path. It means spending the time and effort to discover your unique personal path that will bring you much lasting joy. And that is an incredible thing.
My sons,
You’ve both often heard me talk about having discipline, being efficient, and living intentionally. Without a doubt those are great things to work towards and to cultivate in your lives. Yet as with most things in this world, there is a balance that when struck correctly brings out an undeniable beauty. That balance is the skillful art of creating space, and knowing when and how to do so.
Space
The finest art is that which speaks most loudly to you. As the observer, yours is the only opinion that matters. Regardless of the artist, the medium, the subject matter, the artist’s intention as they created the piece, or even the opinions of the critics, the finest art is that which speaks most profoundly to you alone as the one experiencing that art.
Truly great art leaves space for the observer to explore, discover, and to savor.
It has been said that art is that which you leave out. It is the space created for you to fill with your thoughts, your background, your experiences, your worries, your struggles, and your triumphs. And once filled, it is the gentle nudge that begs us to deeply contemplate.
This concept is one that transcends art and finds its home in many other areas of life. In sports, coaches tell their players to train hard before the game and then to clear their head to give space for their instincts to take over. In love we give space to those we love to allow them to work out their feelings and choose to reciprocate. In music we have natural breath marks, spaces intended to allow the mind to settle and root itself on a mood or theme before being whisked away again. In friendship we share our thoughts and opinions with our friends and then give them the space to choose their own path while we support them wholly. Even in the act of Creation, God rested on the seventh day and made space.
Space to remember
It is with great intention and reverence that we create space to remember. At funerals we create a solemn space to remember the deceased and the life that they led, their impact on us, what they meant to us. At memorials we create an aura of silence to honor the dead and their sacrifice. At graduations we prompt our graduates to pause and reflect on their accomplishments in preparation for what is to come.
Space allows the heart to reminisce, to slowly and deliberately consider that which we are remembering, and to place ourselves in the midst of that experience once more. It allows us to experience more deeply, to love more deeply, to honor more deeply.
Space to heal
We need space to heal. The body cannot heal if we continue to put pressure and strain on our injury. The heart cannot heal if it is constantly being battered and under attack. The mind cannot heal if we continue to relive our trauma without the space or the tools to rewire our thinking. The soul cannot heal if it is not given the time to receive nourishment. When we have broken relationship, we instinctively ask for time and space to think, to ponder, and to heal. Without ever being taught, we know this. Deeply.
It is in that space that we are able to choose to heal, that we are able to take action towards healing. It is not a coincidence that many cultures have mourning rituals that specifically call for time and space to mourn. It is not a PR stunt for companies to offer bereavement time to their employees. It is because the space allows us to mourn, to remember, to honor, and then to integrate the reality of loss into our lives.
Space to grow
As a species, we are wired for growth, for forward movement. It is no wonder we have so many metaphors and images for growth. Perhaps one of the most common and well known images is that of spreading our wings and flying. We know this. We feel it. At a very early age, we instinctively spread our arms wide as we imagine taking flight and going to places currently out of our reach.
The beauty and glory of that image is not only in the jubilant and expectant pose we take, but also of the space around us; the space to explore, the vast horizon spread before us, the breathtaking view of the mountain we are about to soar over.
Human beings are meant to grow, and we need space to do that.
And so I urge you to create space. It may seem counterintuitive. It may feel awkward and unnatural. It may appear destructive at worst and not helpful at best. But we all need space. As you navigate your lives, my prayer for you is that you learn when you need space, how to skillfully create it, and how to confidently and unapologetically take the space that you need.
I love you boys.
My sons,
Something I’ve always valued is retrospection and introspection. Looking back at our experiences to learn from them, and looking within to thoughtfully consider the choices, decisions, and actions we’ve taken are two very good habits to build. As with any habit, it’s best to start building them early and when one doesn’t need them yet. Taking a page from Robert Redford in Spy Game:
“When did Noah build the ark, Gladys?”
“…“
“Before the rain.”
Looking back on this year, it has definitely been one for the history books with all the unexpected twists and turns. It’s been a trying year for most, full of challenges, upset routines, and new and very real fears. It’s brought folks face to face with many insecurities: meaning, purpose, relationship, isolation. It has caused many to look forward, to desire a different future, and to even take action towards making that different future happen.
As we think through those new beginnings, I want us to consider a few important things.
The future is decided by optimists
I’m not just being optimistic here myself, hoping for a future that is defined by optimists. The future will always be decided by optimists.
Why? Because it’s human nature to desire inspiration, to follow those that are inspiring. We are wired to move life forward, to strive for a tomorrow that’s better than today. Optimists paint those pictures, tell those stories, and dream of those grand and epic scenarios.
We aren’t attracted to pessimists. We may resonate with their negativity, and we may seem to connect over a shared disdain, fear, or dislike, but ultimately they don’t attract or inspire us in the long run. It’s the optimists that attract us, and ultimately it will be the optimists that change the world for the better and decide what our future looks like.
Be FOR other people
Coming out of this isolating time, I would challenge us all to be more for other people. We’ve already had enough focus on ourselves this year. Let us make tomorrow more about other people than ourselves. Let us make it a time where we think more of others, do more for others, care more for others, and love others more.
It’s never too late to start
Lastly, it’s never too late to start making the changes you want to see in yourself! If I’ve learned anything at all this year, it is that it’s never to late to get started.
You may have had a rocky start. You may have rough soil to work with. You may have spent years down a path that you’re not happy about. But that’s okay. We move life forward, one step at a time. Tomorrow isn’t defined by what you did yesterday; it’s defined by what you set your mind to do tomorrow. So as we start this new beginning, my challenge to you both is to start it by being optimistic that the best is yet to come, and by setting your minds on being for other people.
Happy new year!