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 posted in 2024
My sons,
When I graduated from college, someone said to me (in jest, I hope, but at the time I couldn’t tell) “welcome to the rest of your life”. At the time, I perceived the statement to signify a transition of states; from childhood to adulthood, from schooling to working, from living under my parents’ roof to living on my own, even from a world with the safety net of mom and dad to one without. Regardless, I subconsciously absorbed the paradigm that this next stage of life was one big contiguous one, and if not the final stage then at least second-to-last from the final retirement stage.
Turns out that mindset is not only wrong, it is incredibly limiting.
When we think about our “adult life” as the second act of our life, one where we are constantly making progress along one single story arc, then we pigeon hole ourselves into the fallacy that it must therefore be the concluding act to the first act of life. And since most (if not all) of the first act was hyper focused on schooling and studying so that we can have successful careers, we can easily be misled into the falsehood that career success is the only true measure of a great life.
It’s easy to think of our entire adult life as a one-act play, that the thing we’re doing right now is the final act. There is a finality to that belief. It at best causes us to think of decisions as incredibly grave, important, and unchanging, and at worst causes us to feel stuck, to feel stagnant, and to be slowly driven to a crises of being, often referred to as the mid life crisis.
Instead, we must realize that life consists of multiple acts, and, most importantly, that we never know if we’re in the last act or not!
Let me restate that, because this is important. We don’t know if the current act is the final one!
This means that it could be, despite us not believing it is, or that it may not be, despite us believing it to be! That lack of certainty allows us to move to a belief that a rich adult life can (and should!) contain many smaller acts, some comic relief interludes, followed by additional acts.
As a result life becomes much more interesting. Our choices become less final and by extension less grave. We can make mistakes. We can take detours. We can choose for a time something that we reverse at a later time. A few great things come when we think of life as having multiple acts.
There is more excitement and possibility in the current act
Because we don’t know whether this act is part of the major plot advancement or some smaller subplot developing, nor do we know the duration of the act, we are left at once with the possibility that this may be the single most important act or may simply be a comic relief in the grand scheme of our life. This in turn allows us to fully live in the moment, not knowing whether it is a pivotal one or an afterthought.
For example, if you thought that this current job was the one you would hold for the rest of your life, your choices become much more grave, your tolerance for error much smaller. If however you thought of it as one of potentially many more stopping points along your overall career arc, then you have room to grow, to experiment, to learn from the mistakes that you make, and to really enjoy each moment.
Or another example (one which I… never… experienced… in my life…). If you thought the current person you were dating would be the one that you’d marry and spend the rest of your life with, then everything becomes incredibly important. Etch her birth date into the deepest recesses of your brain because forgetting that will cause irrevocable damage. The first impression you make on her parents, her friends, her family are even more critically important, as it will make or break your extended family for life. Busy and unable to show up to her sister’s kid’s birthday? Mortal insult and a foreshadowing of how your future children will be treated by their future aunt.
When we instead see the possibility that this act, this job, this girlfriend, this house may not be the one we keep until our last days, then we are free to make mistakes, to be bold, and to learn from our experiences.
We are free to invest in things that aren’t final
When we live with the finality that this is our final act, we feel that everything that does not lead to a successful completion of this act is a waste of time. When we see this phase as just another phase in life, one that too shall pass, then we can invest our time and our efforts in things that may not be final things.
We can buy that two seater sports car for a time and enjoy the wind in our hair. We can date that much younger girl who has “midlife mistake” written all over her. We can wholeheartedly invest in people and friends that may not be our lifelong friends.
As I reminisce on my college days I am reminded of how alive every experience felt. Each interaction, each new friendship, and each deep conversation felt rich and full of meaning, of potential, of lasting consequence. They felt that way because life was uncertain then. It was full of promise, of possibility, of unknown impact on the overall course of our lives. Back then, I never thought about things as being final. Okay fine, maybe I thought I was going to spend my life with my college sweetheart. But aside from that misguided thought, everything else was a stepping stone toward some future I didn’t know the shape of.
We need to keep that mindset. That lack of finality allows us to invest in all sorts of things that we would otherwise shy away from, and that creates an incredibly limited life.
We are free to be alone
There is a difference between being alone and being lonely. The Theologian and philosopher Paul Tillich wrote that “Solitude expresses the glory of being alone, whereas loneliness expresses the pain of feeling alone.”
It is regrettable that many feel lonely, though it is not the topic du jour (though it is likely one we’ll touch on later). It is, however, wonderful to spend time alone, to glory in the experiences that can only had when one is alone. Self-examination and self-discovery are critical internal actions, but so are the external actions of self-reliance and the appreciation of solitary experiences. These are all possible because we know they are not final, because we know there are more acts to come.
Therefore do not be chronic daters, always in relationship looking for the one that will last. Be willing to be alone, fully learning and experiencing the richness that comes from that mode of being.
I’ll leave you with two questions:
What if this is the final act?
What would you do differently? Perhaps you’re 25 with what you believe is a whole life ahead of you. Perhaps you’re 64 and believe that retirement is just around the corner. What if this is in fact the last act?
What if this isn’t the final act?
What would you do if you knew that there were more acts to come? Perhaps you’re 80 and believe that you’ve lived a great life. Perhaps you’re 65 and just starting on your retirement. What if this act is in fact not the last, and there are more ahead of you?
I love you boys, and I hope for a long and beautiful life for the both of you, filled with the deepness and expansiveness of experience. May yours be lives with multiple facets, having taken many journeys, and having found your way home.
My sons,
Ownership is one of the current day buzz words of the tech industry. Everyone seems to be talking about it. Amazon even has it as one of its Leadership Principles. And it’s generally accepted as an unambiguously good thing. But what is it really, and is it actually as good of a trait as we’re led to believe?
When we think about ownership, we generally think of the term in the possessive, the responsible. When it comes to something that we own, we think about the responsibility that we feel for it, the value we assign to it, and the care that we demonstrate in regards to it. We think about the joy derived from our ownership of it, of our uses for it, and ultimately for how it fits into the grand scheme of our lives.
Surely those are all good things, right?
Switching gears to our professional lives, ownership is generally associated with strong, positive behaviors on behalf of a team or an organization. When someone is said to demonstrate “strong Amazon ownership”, we associate all positives with the statement. We conjure images of the employee who demonstrates an almost devout sense of dedication to the team, the cause, and the product. We think, “wow, this person is consistently willing to go above and beyond”, and we sing their praises anywhere and everywhere that we can.
The converse is true as well. When we say people don’t demonstrate ownership, we immediately associate a number of negative connotations with them. They may be selfish, and do not do what is needed in favor of doing what they prefer. They may be lazy, not willing to go the extra mile. They may be not have backbone, preferring to back down from a fight rather than standing their ground for what’s right.
The challenge here is that there’s quite a bit more nuance when it comes to ownership than what meets the eye, and as such we should consider carefully the details that may not be entirely obvious at first glance.
We strongly overvalue the things that we have
Have you ever sold something in your possession? Whether it’s selling a car that you’ve outgrown, clearing out your dorm room as you prepare for graduation, or having a garage sale before a big move, we almost always overvalue the things that we have. This is because when we go to sell the thing, we immediately remember the great memories we’ve had with it. We remember the feeling of freedom that our first car provided, the sense of home and belonging the very first piece of furniture purchased for our first apartment brought, or the sense of accomplishment and adultness we felt mounting our first piece of artwork on the wall.
These feelings, memories, and experiences have shaped us, have made us who we are, and have left their strongly positive impact on our lives, and so we proceed to subjectively assign objective values to them.
The same is true in our professional spaces. We have incredibly fond feelings for the things that we’ve built, whether they be products, processes, teams, or even companies. The blood, sweat, and tears that we poured into delivering a risky feature in time; the long recruiting trips, lengthy conversations, and dozens of sell calls required to hire our team; the hundreds of walls we slammed our heads into before finally discovering the solution that beautifully brings it all together - all of these experiences have shaped us, grown us, and made us better professionals. They bring us joy at their memory, pleasure at their reminiscence.
And we overvalue them.
Whether it’s overvaluing the skill and effectiveness of our team, the importance of our project, or even our own contributions and impact, we have a very difficult time objectively assessing the true value of the things that are entrusted to our care.
We have a strong aversion to loss
When it comes to the prospect of losing something in our possession, our overemphasis of what we may lose is very strong. It is emotional, it is not rational. We intrinsically have a strong emotional attachment to things that we own, and therefore have a strong emotional aversion to losing those things.
This starts at a very young age. It is a very common sight to see a young child fiercely defend their toy from another, for fear of losing that toy. “Mine!”, they scream, only to put the toy down and race after another when they discover that the other kid has lost interest in their toy. The fear of losing what’s ours is incredibly strong.
This is again true in our professional lives. We have a strong aversion to the loss of whatever it is we’ve accrued; reputation, prestige, influence, team scope, headcount, even superfluous things like the bigger office, the better view, or the desk closer to the kitchen. While it may be somewhat positive to be protective of one’s team, and while there are times when having backbone to fight to keep strong value that we’re adding for our customers, our aversion to loss may often overpower those other benefits if we’re not carefully aware of ourselves.
We assume others see transactions from the same vantage point that we do
When it comes to transactional exchanges, we assume that others see the transactional targets with the same value that we do. Typically we are giving up something we currently own in exchange for something we currently do not, and we assume that the other party sees both objects in the same light that we do.
Since we tend to overvalue things we own, we are already prone to seeing our side of the transaction as having a higher value than it might objectively have, which our transactional counterpart will not see. Further, our counterpart will in turn see their side of the transaction as having a higher value than we will see, making this a double whammy and creating potential hurdles for us to have mutually satisfying transactions.
Overvaluing ideas
A final observation is that these quirks about ownership apply to the idea marketplace as well! We tend to overvalue our ideas and opinions, and will feel a sense loss when they are not valued, changed, or discarded. This too is natural.
Earlier in my career, I had a really great idea. I was working on the C# compiler at the time, and my buddy and I had this great idea to take the compiler and split it out into distinct phases, allowing those phases to be called at various times from the IDE. We spent a bunch of time building this, getting all our tests passing and all that. Then when we pitched it to our boss, he said no. I couldn’t believe it. How dare he! I couldn’t even hear his reasons I was so mad!
I made all of the mistakes we’ve been talking about. I overvalued my idea because it was mine. I overvalued the work that we had done on our prototype because I had poured my heart into it. I assumed he saw things from my perspective and valued the same things I did. Turns out, all those things were blind spots for me.
So what do we do with all this?
I believe that the key is to be aware of these quirks about ownership. There are undoubtedly many great outcomes to be had from demonstrating strong ownership, and it is without question a trait that is highly valued - required even - on great teams. But like most other things in life, too much of a good thing can become a bad thing, and these small quirks of ownership can rear their ugly heads at precisely the wrong moments if we leave them unchecked.
My hope for you is that you encourage one another to check that. That you never let your strong sense of ownership turn into competition, jealousy, overprotectiveness, or any of the other myriad of challenges that come from overcompensation of a good trait. Keep each other accountable in this, and be well.
My sons,
One of the most important factors that give life meaning is the passage of time, and its finite supply for each person’s existence. Without it, our actions have no meaning. With it, everything we do is viewed with the lens of the finite, and as such is a trade off of all the other things we could have done but have chosen not to.
A necessary (though often not taken) reaction to this is the act of maturing, of gaining perspective, of acquiring wisdom. As our time spent on this earth increases so too should our understanding of the big picture, of the tradeoffs required of us, and of the balance required to live a rich and fulfilling life.
Dying nobly
A beautiful characteristic of youth is its tendencies to lay it all out on the line, to throw caution to the wind, to go big (albeit without the slightest consideration that one might actually need to finish the second half of that phrase, “or go home”). Call it youthful arrogance, call it inexperience, call it a lack of perspective, or whatever else you may desire to call it, it is pretty widely accepted that youthfulness tends to be bold, to be idealistic, to favor action.
When we are young, we get fired up. We lean into causes, we want to go all out. We feel indignation at the errs and inconsistencies of the world. We want to fight, we want to make our lives count.
Our culture promotes this. We revere fallen heroes, we memorialize those who have made the ultimate sacrifice. We write stories about those who stand up, those who fight the good fight, those who refuse to take injustice sitting down. Everything seems more dramatic, more urgent, more impactful.
We feel more, love bigger, suffer more intensely, and even soliloquize more dramatically. We dream big. We long for a perfect world. We see injustice and we want to fight it. We see suffering and we want to end it. And we want to make grand gestures to do it!
Unfortunately, we are also indiscriminating about the cause which we want to fling ourselves headlong into. How many of us have not spent agonizing hours in a hair-pulling, helpless, even hopeless state over some unrequited love, some immovable and unchangeable consequence that prevents us from pure joy? And how many still cannot commiserate with the thought of making some life-ending (or at least, life-changing), impulsive, and probably stupid gesture as a result?
Come now. Be honest.
For me, it was seventh grade. Or perhaps ninth. Tenth? Twelfth for sure. Really, probably all of the above. My high school years were characterized by many immense mountaintop highs followed almost immediately by some unfathomable lows. Being dumped by my first girlfriend of a whole long 3 weeks, 2 of which were over Christmas break… over a written note no less! Or having my existence ignored by the pretty brunette whose name I can’t remember but whose face I can’t forget. Or wanting to crawl in a hole after thoroughly embarrassing myself in front of someone whose approval I longed for. Or almost failing to secure my first job because of some laissez-faire attitude applied to a misread situation.
Yeah, I’ve had my fair share of moments of wanting to go out in a blaze of glory.
Living humbly
Thankfully, those moments passed and I grew up. I matured. I developed more resilience, more balance, more understanding of the nuances of life. It has been said that
“The mark of an immature man is that he wants to die nobly for a cause, while the mark of the mature man is that he wants to live humbly for one” - The Catcher in the Rye
Absolutely beautiful.
As we mature, we begin to discover that our impatience tempers, our bias for action slows, and our once raging fire tapers down to an unobtrusive flame. Our youthful hotheadedness begins to cool, if not intrinsically then at least extrinsically due to our newfound understanding of social ramifications of unconstrained actions. And so we inevitably mellow out.
The danger here is to take that mellowing too passively, as so many do. Too many of us take the uninspired path of allowing the loss of our youthful arrogance to be replaced by a mature apathy. We fall out of our fiery and hyper-sensitive experiences into pools of insignificance, of lukewarm, purposeless living, and we follow an all too familiar path towards the midlife crisis - that existential crisis of purpose and belonging.
The best of us, however, learn that there is another path, another way to go that doesn’t lead to either a flame out in a blaze of glory or a slow and lackluster burn out. The answer is to put in the hard work necessary and learn to live humbly.
Why is this hard?
- Living humbly means genuinely caring about a cause greater than ourselves, more than ourselves.
- Living humbly is counter-culture. In a world fixated on Instagram photos proclaiming our wealth and experience, LinkedIn profiles touting our professional accomplishments, and ever more curated filters and edits of our public personas, being humble is quite unfashionable.
- Living humbly means suffering in silence, taking those inevitable injustices thrust upon us nobly, with dignity, and with a patient and calculated temperance that tempers our instant desire to rage out with indignation.
Lin Manuel Miranda’s rendition of George Washington says it well when he admonishes Hamilton:
“Dying is easy; young man, living is harder”
Living, indeed, is harder. Living humbly, harder still.
A few suggestions
By no means do I have all the answers, and by no means have I figured this out in a way that I can daily apply this to my own life, so take these suggestions as simply my thoughts in my journey.
- Actively look for places where you’re not the smartest one in the room. Our egos desire recognition and praise for our contributions and efforts. In seeking environments where others are further than us, we increase the ease by which we can place ourselves in postures of humility.
- Read. A lot. One of the most beneficial impacts of reading is that it puts us in our place. It causes us to come to terms with the fact that there is an incomprehensible amount of information, knowledge, and wisdom that we do not possess. At the time of this writing, it is estimated that the world currently contains anywhere between 125-150 million books. The amount of collective wisdom, experience, and knowledge contained in those volumes is enough to humble even the most arrogant among us.
- Measure your learnings, not your accomplishments. Instead of measuring what you’ve done, measure what you’ve learned. What we’ve learned tells us story of the journey; what we’ve done, the destination. The journey is infinitely more interesting.
My boys, my desire for your lives is that you would be kind, that you would be surrounded by people of integrity, and above all else that you would live lives characterized by a posture of humility and an eagerness to learn.
My sons,
I have always been a firm believer that the written word has power. Words have the power to create, to bring life, to elevate, and to empower, but they also have the power to tear down, to diminish, to dishearten, and to bind. They are the tools we use for communication. Whether we are conveying ideas, expressing sentiment, sharing dreams, or commiserating loss, they allow us to connect with each other with great depth and high fidelity.
We are a communal species. Whether you believe in creation, evolution, or whatever the latest theory of the day is, human beings are social creatures. We need one another. Together we stand. Divided we fall. And humanity has stood for many millennia, and hopefully will continue to do so for many more.
And so it behooves us to not only understand the power of our words, but to study, to learn, and to develop mastery over them. When used effectively, great authors and speech writers can smash through walls with them, can distill even the most complex of ideas for the masses, and can embolden an entire generation with them.
Our inputs inform our perspective
The things we take into our system inform our perspective. The things we read and hear daily impact the way we see our world. The words we commit to memory, the phrases and mantras we recite, the encouragement we hear from our environment - these all impact not only how we respond to our world, but also the people whom we are becoming.
It therefore is in our best interest to be vigilant in managing the inputs we get on a regular basis. Remember that it is not the severity of the input but the frequency that matters.
My mentor told me once that as a manager, when I feel that I’ve repeated myself so much that my team must think me to be a broken record, that is the point at which they may actually begin to hear me. So too are the inputs in our lives. When we encounter something once, our brains can filter that out as an outlier, but when we are consistently bombarded with the same message repeatedly across multiple channels, we begin to give credence to the message regardless of the strength of our defenses.
As such, we must watch our inputs.
The words we say and write shape us
Closely related is the fact that the words we say and write also shape us! Turns out that we like the sound of our own voices. Our ego is the portion of our personality that is experienced as “the self”, or “I”. It is the consciousness of your own identity that distinguishes itself from others and the external world. And the voice it listens to the most is our own.
This means that the things we say and write not only impact others, but they impact ourselves too! They reinforce ideas, they alter our emotions, and they change the way we see the world. We’ve all heard of the power of positive thinking, of power poses and of self-affirming inner (and outer!) dialogue. The reason that those things work is because they leverage the fact that our ego, our conscious mind, our “self” listens to us.
It is therefore important not only for us to guard our inputs, but for us to tailor our outputs as well! The things we discuss and debate, the company we keep, the topics spend our time learning about and sharing with others - all of these are important in shaping the people that we become!
This is why the Good Book tells us in Colossians 4:6 to
“Let your conversation be always full of grace”.
In speaking with grace, we become people of grace. In sharing big ideas, deliberating, debating, challenging, questioning, and reframing them, they become a part of us. In talking about great character and lofty traits that we desire for ourselves, we slowly but surely take them on. In speaking of our love for others, of why we love them, and of the things that desire for them, we not only encourage our listeners but we enlarge our own love for them.
We live in a time of influencers and trend setters. We live in an era where people are bombarded with all sorts of inputs ranging from traditional media, books, articles, social media, and podcasts that it is easy for us to become silent. Let us speak. Let us speak of elevated things. If we wish to be always relevant, let us speak of eternal things, of character, of compassion, of love for our neighbors, and of our moral duty to our world.
The power of writing
Finally, we must write. The written word has power for those that read, but it has an even greater strength to impact those that write! As surely as speaking changes our lives, how much more so does writing! Writing requires deliberation. It requires thought. It requires us to sit in silence, contemplating the concerns of our hearts so that we can express. It allows us to refine our ideas and discover the coherent themes across them, and in doing so makes us better.
And so my sons, I urge you to endeavor to master your words. Be mindful of your inputs. Be thoughtful in your outputs. Speak. Write. Listen. For these are the things that refine us as men!