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,
All of us have dreams. From a young age, we learned that the sky’s the limit for human ingenuity. We were told that we could be anything, do anything. But over time, those dreams start to fade, and our belief in our ability to achieve them (nay, whether we even deserve to achieve them) starts to fade. Most of us have lost sight of those adolescent dreams and have settled into the mediocrity that is adulthood. We are content in living the life that we’re supposed to live - a life that plods along slowly but surely, doing all the things that our culture tells us area part of a properly lived life.
Sounds pretty dull doesn’t it?
How do we snap out of that? How do we move back into a space where our lives are exciting, where we’re passionately running towards some big, lofty dream, and where inspiration comes and drives us to our limit and pushes us beyond where we ever thought we could go?
The answer is simple, and comes in the form of all sorts of cliches. Take your pick of them:
- Less is more
- Gotta take two steps back in order to set up three steps forward
- It’s not quantity, it’s quality
The truth of the matter is, our lives are so jam packed full of stuff, filled with noise, and overflowing with the seemingly urgent that we have no margin, no time, no mental space to allow ourselves to listen. It has been said that inspiration is very polite. She knocks softly and then goes away if we don’t answer the door. She does not force her way in, does not make a big fuss, does not cause a scene.
We cannot shove inspiration down someone’s throat. We knock softly, and if they’re not ready to answer, that’s okay, we can come back some other time. Similarly, we cannot be inspired if we are not paying attention to the knocking on our own doors. If we are too caught up in ourselves, too focused on our own worlds, or have too much noise drowning our ears, we will miss the gentle whisper that inspires and elevates.
If we want to hear the gentle whisper of inspiration we must first learn to listen, and to have the margin and mental space for her.
Learning to listen
An unfortunate reality of our modern world is that we are driven by noise. We praise great orators, admire the outspoken leaders, and aspire ourselves to have that type of impact. As a result, we focus much of our learning and our development on how to speak, how to convey an idea, and how to be heard.
But we don’t spend time learning to listen.
Active listening is a skill just like any other - it can be learned, can be practiced, and can be improved upon. It has nuances like every other skill does. It has its masters and its novices. Some are born with more of it, some with less. And like every other skill, where we start doesn’t matter. We can all learn to actively listen so that we are more attuned to what is going on around us.
Creating space
One of my most cherished habits is my nightly thinking and processing time. I use a modified version of Zettelkasten to support my growth and learning, and one of the disciplines I’ve picked up from it is creating space every night to process my thoughts from the day and to synthesize my notes into my own system. This process requires me to first sit and clear the thoughts in my head and then to pick up each thought that I’ve recorded throughout the day and to consider it, process it, and synthesize it into a long form paragraph or two.
Which system you use is less important. What matters is that you have a system, and you have a method by which you nurture and care for your thought life. The daily nurturing of your mind allows you to create space to listen, to be attuned to your surroundings, and to see where your thoughts lead you. This is gonna sound cheesy, but I’m going to say it anyway - your mind is like your sacred garden that needs to be tended to and taken care of. Cultivating a healthy and strong thought life will provide benefits to every other area of your life.
Cultivating our inputs
We must therefore be intentional about our inputs. Tending to the garden of our mind means we are thoughtful and careful about what we let into it. This should be an obvious one, and despite the fact that we’ve all definitely seen the effects of not guarding our minds well, most of us could use some improvement in the things we let in.
We’ve all done this and all have first hand experience with this. Remember that friend who was constantly negative and could (and would) complain about anything and everything under the sun? Prolonged periods hanging out with them probably made us more negative as well.
It works in the opposite too. When I was younger I had a great friend who was super passionate about technology and about the product that we were working together on at the time. We spent countless hours discussing the work we were passionate and excited about, and would even discuss some of the technical details of our work while on the chairlift at the slopes. It’s no surprise then that this period of my life was characterized by strong technical thinking and development, as well as a high amount of professional productivity.
I in turn was very much into motorcycles and would openly drool over the latest super sport bikes that were released each year. It’s also no surprise that my friend ended up getting a motorcycle as well.
Great inputs have the power to lift up a life, to change our mind, and to enrich our thought processes and passions. Bad inputs have the power to pollute our mind, to destroy our sense of self, and to turn a once-productive mind into a destructive one.
The gentle whisper of inspiration
Inspiration comes in many forms, and may sound different to different people. She may take different approaches, may speak through different people and events, and may look different each time she tries to visit us. She may speak to us through listening to a stranger’s story on the plane, or through the sight of a bird soaring high with “god rays” bursting through the clouds. She may nudge us when we’re dozing off watching the trees roll by on our commute, or may give us a glimpse of something greater as we’re playing with our kids.
One thing is certain though - she always whispers.
There is no sure fire way to guarantee that we will hear her every time. But if create space, if we spend the time to be mindful and attentive, if we learn to follow the little inklings that begin like whispers in the wind of our minds, then we may learn to distinguish her voice and pay more attention when she speaks. But we’ve got to be ready to listen to what she says! Remember that there is no confirmation bias for inspiration. She may often say things that make us think twice - that is a good thing! An inspired life is an elevated one, and we can surely use more of those in our world!
My sons,
A characteristic of the modern world that we live in is that we always seem to be short on time. We never seem to quite have enough time for all the things that we want to do, and the time we do have seems to slip through our fingers in a manner that leaves us not remembering what we’ve been up to, and wondering where all our time actually goes.
Whether we’re talking about our professional life (there never seems to be quite enough time to finish all our features, to fix all the bugs, to polish all the user experiences, or to ensure we’ve got the right metrics) or our personal life (how many of us are happy with the amount of time we spend on social engagements, with family, and with loved ones?), we never seem to quite have a handle on our time. The older we get, the busier life gets and the more problematic this becomes.
When time was a luxury
When we were younger, we had what felt like an abundance of time, especially when compared to the lack of other resources (such as money) and minimal commitments and responsibilities that demanded our time. We could therefore trade off time for other things. I distinctly remember in my college years standing at the corner of Albert and Columbia where I lived, and contemplating walking the 45 minutes to Conestoga Mall or spending the 3$ to take the bus. I walked. Yikes.
Not only were there fewer taxes on our time back then, but there were fewer things for us to do with that time. For the majority of us, the only real available options were hanging out with friends, studying, playing sports, playing video games, or eating. Or sleeping I suppose, but that’s one thing college students never feel like they need to do much of. Maybe give or take a few more things. But realistically, there were not that many options for us to balance between, and so we had plenty of time at our disposal.
Subservient to the system
Fast forward a number of years, and we find ourselves with more things to do than we can mentally keep track of. Things ranging from replacing dead lightbulbs to remembering kid birthday parties, from scheduling a follow up dental appointment to remembering to congratulate a friend on their promotion. Everywhere we look there is something we need to be doing, something we need to remember.
And that’s just the things we have to do. What about the things that we want to do?
What about finding time to have a heart to heart with a loved one, or to read that self-help book that’s been so highly recommended for you, or to try that new restaurant, or to simply sit and think? With all the taxes on our time, is it a surprise that most of our wants and desires go unfulfilled and unsatisfied?
60% of Americans feel they are too busy to enjoy their lives most of the time, while 12% feel they are too busy all of the time. That means that one in ten of us feels that we never have the time to enjoy our lives, that we are always too stressed to make forward progress in the things that we desire to do.
If this isn’t subservient to the system, I don’t know what is.
The important over the urgent
It is universally accepted that when push comes to shove and our time constraints squeeze more tightly, the things we trade off are the non-urgent but important things. This is the tyranny of the urgent, and happens in both our life and in our work.
In life, how many of us have traded off our personal reading and development time because we’re too busy? How many of us have told our kids to come back later when mommy or daddy isn’t working on something urgent that came up? How many of us have showed up late to a friends’ gathering and left early to rush home for that work call instead of showing up early to support and build that relationship? What about healthy eating and home cooked meals? What about daily exercise and meditation?
In work, how often do we make the short term fix instead of the right long term architecture? How many times have we swarmed to some urgent and tactical problem rather than spending the time to develop the right long term team and skill sets? How about burning a bridge with a partner team by escalating and effectively forcing them to get what you need done? How often do we focus on the transactional rather than spending the time to build ~non-transactional relationships~?
Managing the time you’ve got
It is true that much of our time is not our own. Time is a networked resource and gains value expressly because there are others that can make demands on it. As we grow in our lives and in our careers, there become more demands of our time that truly are outside of our control. How we manage the demands, and most importantly, how we manage the remaining time we have left is crucially important.
So how do we do this effectively?
1. Ruthlessly prioritize what you need to be in top shape
Perhaps the hardest one to do, it is also the most important. We need to take the time to thoughtfully determine what the daily requirements are for us to be in top shape. Have you ever shown up to a meeting fully prepared but not feeling your best self? You know your stuff, but it just doesn’t come out right. That’s because you’re not at your best self.
Take the time to figure out what that means, and be unapologetic about it.
Personally, I never leave my bedroom in the morning without having showered, groomed, dressed well, and made my bed. I spend at least 30 minutes a day reading, and spend as much if not more time than that thinking. With a few allowed exceptions, I also need to eat healthy. I need to exercise daily (this one’s been a struggle… but I’m working on it). I need to have quality sleep for at least 7 hours a night.
I am uncompromising in these, as without them for prolonged periods I am not able to be my best, and everything else suffers as a result.
2. Dedicate time to thinking
Another characterization of an overloaded life is that things are frantic, frenetic, and unorganized. We jump from urgent thing to urgent thing and run at a break neck pace for as long as we’re able. We spend all our time doing, and as a result end up decreasing our effectiveness by not thinking enough.
Most of us live reactionary lives. We react to the incoming torrent of tasks, demands, and requests made of us. We don’t spend the time to deeply think about what, and more importantly why we are doing what we’re doing.
Thinking deeply requires time. It requires dedicated, uninterrupted time. Our brains are bad at multitasking, and can easily get distracted. In order to be our best selves and to be the most effective and efficient in our endeavors, we need to spend time thinking. Whether we’re thinking about our intentions, our options, the possible alternatives, how to develop our staff, or our strategic advantages, we need the time to thoughtfully pore over our thoughts, data, and inputs.
Bill Gates used to have Think Weeks where he would go off himself to a secluded place with no interruptions and dedicate the week to reading, learning, and thinking about the business. While we may not all have the luxury of clearing out a full week like Bill could, we can certainly block off time throughout our week to think, and to remove the distractions and notifications while we’re doing it.
3. Learn
Above all things, we need to make sure we are learning. As our world evolves around us, we too must grow and evolve with it. Our thinking needs to adapt and mature. Our reactions need to consider new inputs and alternatives. Our plans have to accommodate the shifts in technological advances that are underway.
As such, we need to ensure that we are carving out time to learn. Whether it is a weekly time block, a quarterly retreat, or an annual reading goal, it is imperative that we dedicate time to our own learning and enhancement.
Putting it all together
As a manager, I need to get better about creating time and space for my teams to do these things. I can help by sharing more context, reducing meetings, and empowering more decisions to be made lower in the organization. As an employee, I need to be willing to take responsibility for the immediate outputs that I have balanced against the long term growth that we’ve been discussing. As a person I need to think about the big picture not only of what I’m accomplishing, but more importantly who I am becoming.
And above all, I have to have the patience to see this through, knowing that the tweaks I make in my life won’t produce results overnight, but will set me up for a lifetime of greater success and happiness.
My sons,
Human beings are wired for play. In our earliest years, life basically consisted of eating, sleeping, and learning through play and exploration. If you walk into homes with young infants or toddlers, you will commonly hear the sound of laughter, of bubbly little voices excited about the brand new discovery that squishing the plastic giraffe causes it to emit a squeaking sound (both of my children grew up with Sophie the giraffe teething toys).
But something strange happens in elementary schools all around the world. We begin to change the daily environment of our children from one dominated with play and exploration to one filled with learning, memorizing, and study. Once they hit middle school, daily scheduled play time (aka recess in America) gets eliminated altogether. Free play time at home after school gets replaced with extracurricular activities and more homework. Even volunteering, which used to be a self-initiated activity stemming from the goodwill of one’s heart has become a required prerequisite by our educational systems.
By the time that child graduates from college, free play, which used to consume the majority of their days, has been transformed into something that we relegate to our 3 weeks of vacation a year if we’re lucky. That child now lives in a culture that serves the god of progress and achievement, a god which happily will take any and all time that we do not fight to hold onto. They are told that excessive play is immature, and are in an environment that regularly reinforces that their only purpose in life is to make progress.
The benefits of progress
Let’s be clear - I’m not advocating for us to play constantly and to ignore our responsibilities in favor of that play. Our world is increasingly complex and requires increasingly dedicated, educated, and creative people to continue to make it better for us all. And let’s make no mistake about it - our world is infinitely better than the one previous generations lived in, across any and every measurable metric.
Average lifespans worldwide are longer. Many deadly diseases have been either eradicated or made treatable and non-fatal. More people are being educated. There is greater (although not perfect) gender equality. There is less violence and crime. The number of people in the world who have electricity has increased from 70% in 1990 to 90% in 2022.
I know there will be some that argue that the world is a more dangerous and terrible place than our past - to those I will highly recommend two books: Steven Pinker’s ~The better angels of our nature~ and the late Dr Hans Rosling’s ~Factfulness~.
On a more local scale, we have persistent access to the internet. We have a plethora of options of electric cars and carbon-zero household products. We have the ability to say goodnight to our home assistant and have her turn off all the lights, close all the garage doors, lock all the doors, lower all the shades, and turn off the bed warmer that was keeping our bed at a balmy 80 degrees for us to climb in. (Okay, maybe that last one was just princess Sam in action).
No matter how you dice it, that progress has many benefits.
The evolving conditions for progress
Unfortunately, our conveyor belt approach to equipping our children to carry on that mantle of success is in need of an update. While it is true that decades ago our assembly line approach to education produced workers skilled enough to work the machines of the day that propelled our world forward, our world has evolved, and the needs and conditions for that progress have changed.
As our world continues to move from physical and manual work to knowledge work enhanced by greater automation, the need for creativity, imagination, and ingenuity have become the new baselines for advancing our world forward. And as it turns out, creativity cannot be taught, it must be fostered and nurtured.
Intentionally unproductive
As a child, I found myself constantly bored. Whether it was sitting in a boring Canadian history class (I must have read about Vimy Ridge, the one important thing Canada did in WWI a thousand times) or sitting at home after school with no access to video games and on-demand TV/movies, I was constantly bored. I strongly believe that that boredom played a huge part in helping me achieve much of what I have accomplished in my life.
That boredom was the fertile ground that enabled my brother and I to invent games to play. It gave me the time and space to dream up worlds and explore them in my mind’s eye. It gave me impetus to read, to imagine, and to dream. It allowed my mind to wander into all sorts of places and situations.
Granted, there were down sides as well. I got myself into a lot of trouble because of that boredom (my mom and my principal were on a first name basis…), and I found myself more often then not finding creative ways to be mischievous. While running around with a can of WD-40 and a lighter lighting spiderwebs on fire and flushing out ant hills wasn’t particularly useful (or safe, really), that time of non-productivity was a launch pad for all sorts of creativity.
It turns out that our subconscious minds are much more capable than our conscious ones. It also turns out that our conscious minds are much louder than our subconscious ones, so if we’re constantly engaged, our subconscious minds have little time to be active and to make connections on our behalf.
DaVinci knew this. Excerpts from his recovered notebooks showed that not only did the grand master paint and create timeless works of art, but he allowed his mind to wander to all sorts of unrelated and fanciful topics. In 1485 for example, he imagined the first parachute three centuries before an actual parachute was made and deployed successfully, and he detailed out specifications for it in one of his notebooks. It was constructed in 2000 and demonstrated to work successfully at 10,000 feet! He also imagined a submarine, a helicopter, and solar power among many other things.
How did he do all this?
He had intentional unproductive time. He knew that his mind needed rest, space, and margin to do its best work, and he actively created time to daydream. He would often go for walks with nothing on his mind and nothing in his hand but a pencil and a notebook and presently realize that he had filled many pages with seemingly unrelated thoughts. In 1994, Bill Gates bought one of DaVinci’s notebooks for $30M. Other notebooks have gone for $5M or more.
Creating margin
I will never be a DaVinci or a Gates. Neither will you. But that doesn’t mean we can’t learn from the greats of our world and integrate some of their practices into our lives. It turns out there are many studies that show a plethora of benefits of having margin and allowing ourselves to daydream. A few benefits:
- We become more creative. When we daydream, our subconscious minds make connections between seemingly unrelated topics, letting us maximize the learning and benefits we get from our experiences.
- We can build better relationships. Something my college advisor told me that has stayed will me to this day is the truth that if you want to make connections with people, you have to make space. People don’t have crisis moments when it is convenient for you to show up for them. They don’t have breakdowns, epiphanies, or life changing events happen to them on your schedule. If you don’t have space for them, they will find someone else that does.
- We become more interesting. By giving ourselves margin to daydream, to pursue hobbies and interests, and to explore and experience without agenda or purpose, we become more interesting! No one is interested in a cookie cutter person that just eats, sleeps, and works. People are intrigued by those who go off the beaten path and explore!
My sons, I know that there is great pressure for you to be always productive. I know you’ve been told that the stakes are high. I know that without a doubt those things were told to you with the best intentions. But they don’t tell the whole story. Be productive, yes. But also make sure you spend time to be intentionally unproductive - I guarantee you won’t regret it!
My sons,
Lately I’ve been thinking a lot about culture - team culture, family culture, friend group culture - and how much it impacts our lives. In his book Wanting, Luke Burgis explains how much of what we think we want is not actually intrinsic to us but is rather a product of us mimicking those around us, mimicking the culture we have. If that’s the case, culture is an incredibly important thing for us to think through.
What is culture?
Culture is not what we desire to do. It is not a set of principles or values that we print out and put on the walls to inspire our teams. It is not “the way we’ve always done things”, nor is it what our founders had in mind.
Culture simply put, is the way we do things today.
That means culture changes with each new day, with each new person that joins the team, with each new adjustment to the daily norms that we introduce. It means that culture shifts and grows as we do.
Culture is the way you spend an extra 10 seconds to say “hi” to everyone on your way in. It is the way we gather everyone on the team to go to lunch everyday. It is our willingness to speak up in meetings, our courage to express our opinions, and our trust knowing that those opinions won’t be slammed down by our peers. It is how we utilize documents or presentations, what our expectations are of instant messaging and email, and how much information we share with or withhold from our partner teams.
And it is what every new person gravitates toward when they join us.
An intentional culture
The thing with culture is that it can happen “naturally” (aka accidentally) or it can happen intentionally. Intentionality is better.
I’ve had the privilege of seeing many different types of leaders at work, each with a wide variety of skills and competencies. I’ve seen leaders that are hyper intentional about the culture of their teams, and I’ve seen leaders who simply accept whatever culture their team has as long as the leader is able to work in the manner that they prefer.
The leaders who had a firm understanding of the type of culture they wanted to cultivate on the team were not only more well-liked (turns out people like it when their leaders care about their experience), but their teams had more longevity. Regretted attrition rates were lower, team loyalty and ownership was stronger, and willingness to collaborate was noticeably higher.
Some of this is obvious - a leader that cares about culture naturally values people who care about culture as well, thereby building a virtuous cycle of people who are intentional about the environment, habits, and practices of the team.
Less obvious for instance, is the reality that leaders that cared about culture typically cared to see the impact of the culture they’ve created. They engaged themselves in inclusive behaviors, in learning from the team what’s working and what isn’t, in getting feedback, and in having dialogue and discussions with the team. These leaders cared about culture, and spent time actively crafting, refining, and sharing. They led by example, both in their communications and in their behaviors.
What makes a good culture?
There are a number of dysfunctional behaviors and norms that have permeated themselves into our world, with some much less obvious than others. Unfortunately for our world, there are still some very overtly dysfunctional cultural habits in the workplace today. Things such as blatant disrespectful and discriminatory behaviors towards women or clear minority groups unfortunately still happens today. Less obvious are things like CYA (cover your ass) cultures, cultures where bosses take credit for their team’s work, or hierarchical cultures where subordinates don’t speak up unless spoken to.
Healthy cultures on the other hand tend to balance productivity with fulfillment. Healthy cultures are ones where people can come as their authentic selves and do their best work together. They are cultures which enable and empower while keeping strong expectations and a high bar. They are cultures that elevate people and stretch people, allowing them to grow and develop, not just as workers but as people.
My SVP says it incredibly well. He says he builds teams of passionate and relentless people. I love that.
We want to create a culture where passionate and relentless people thrive. People who are incredibly passionate about what they do, about the mission that they’re on, about the impact that they have on the world, and about their craft and their role in achieving that impact, but at the same time are relentless in their pursuit of excellence, in their dedication to their craft and their learning, and in their desire to build the best thing for their customers, whoever those customers may be.
There are a few things that are essential to create a culture that fosters these behaviors.
- Open communication. The most critical ingredient required for great teams is open communication. Any culture where a diverse set of passionate and relentless people can thrive deeply requires open communication. This is because people are different. When you’ve got a lot of strong people together with poor communication, inevitably one person ends up steamrolling the rest without listening to others and you end up with an adversarial and mistrusting culture.
- Strong opinions, weakly held. Another key part of great team cultures is the ability to have weakly held opinions, to be convincible. The world is big. The amount of information, knowledge, and wisdom out there is astronomical. To think that one individual has it all, is always right, and knows best is not only improbable and naive, but just down right stupid. We therefore need to build a culture that recognizes that great ideas can come from anyone, anywhere. Have opinions, yes, but be willing to be convinced of other viewpoints as well.
- Regularly revisiting cultural norms. Great teams need to regularly revisit their cultural norms and reevaluate whether adjustments need to be made. Our world changes - new technologies develop, the business landscape changes, societal trends shift - and if our teams wants to stay relevant, we need to change along with it. In order to ensure we do that well we’ve got to regularly revisit our norms to decide if the patterns and practices that have served us well in the past will continue to allow us to excel in the future.
Whether we like it or not, whether we’re conscious of it or not, and whether we have input into it or not, culture affects each and every one of us. It is the set of norms that we automatically take on whenever we enter the sphere of any group that we’re a part of, whether that’s work, friends, church, or even family. The more awareness and thoughtfulness we have the more we’ll be able to help craft and shape our cultures to be healthy and empowering places for all of us.
My sons,
Hobbies are supposed to be embarrassing. In this day and age where everything is supposed to be productive and well-polished, hobbies are explicitly not. They don’t further our careers, they have no future payout, they aren’t things we post about on LinkedIn. The reason we have hobbies is for the hobbies themselves, and as a result the world inadvertently looks down on them, which in turn causes us to be occasionally embarrassed about our hobbies - this is totally okay! This likely means we’re doing something that the world thinks is non-sensical, which usually indicates that we’re doing it because we love it.
In a world that is obsessed with forward progress, that preprograms us all to constantly strive for success, and that is becoming ever more impatient with delays each day, hobbies are counter-cultural. Think about the last few social interactions you’ve had, especially with new people that you’ve just met. Chances are, you talked about work (potentially at length!). Potentially you made some idle chatter about the weather, and if you’ve got kids, you probably talked about them and all the craziness that goes along with being a parent. Maybe you talked about the latest world events, latest technological advancements, or latest crazy policies to come out of our government.
If hobbies were mentioned and discussed, you were probably met with polite smiles and gentle nods, with eyes that seemed to say “oh what a quaint little hobby you have there - that explains why you’re not as successful/accomplished/[insert your choice of success metric here] as you could be!”.
Unfortunately, that is a huge misunderstanding of the value of hobbies, and of the potential that having great hobbies unlocks in one’s life!
Why we have hobbies
Growing up in a western society taught me to live life for tomorrow. From an early age it was imprinted on me that we do what we do today so that tomorrow will be better. Get good grades in high school so that you can get into a good university. Learn a lot in university so that you can get a great internship that will lead to a full time job opportunity. Do well in your job so that you can climb the corporate ladder and have a great life. It seemed like everything was done expressly for something else in the future. Even volunteering was done so that it would look good on your college applications.
That type of mindset misses the point altogether.
The justification for writing is the act of writing. Not some external benefit, not some reward or glory, but the pure beautiful act of writing itself. The reason we sing is simply to sing, to revel in its singular beauty. The reason for doing something ought to be the thing itself!
I read once that it is quite possible that this is the imprint of God. That there is beauty in the thing itself, without justification, without recognition, but simply because it is.
I love that.
Hobbies are important
We have hobbies simply for the sake of the hobby itself, for our interest in it, and for the joy it sparks in us. And as much as our hyper-growth-focused society tries to tell us, they are important.
In his New York Times best selling book ~Range~, Peter Epstein masterfully argues that our belief in specialization at an individual life level is misguided. Stories like that of Tiger Woods, debatable GOAT of the game whose father handed him a golf club at age 2 and who hasn’t stopped winning in the game since are inspiring and are distinctively noteworthy. However, folks like Tiger who have done one and only one thing their entire lives are the exceptions and not the rule.
The vast majority of the hyper successful have had a range of experiences which they’ve drawn from, many of whom owe their successes to the exposure, experience, and wisdom they gained in those arenas. Whether it is experiencing different companies, industries, or even just different bosses, the successful among us are the ones that have learned to harness the range of their experiences - both consciously and subconsciously - to their advantage. As Epstein explains in his book, the subconscious mind makes connections from realms of thought and experience that our conscious minds can’t draw any connection between and in fact may find ludicrous. Accounting theory being used to solve chemistry problems in molecule constitution. Hospital administration strategies used to solve computer science problems in concurrency.
The neural pathways that our subconscious mind creates between our various experiences lead to conscious discoveries and realizations that would never have been possible without. And hobbies are exactly that - a range of experiences that are typically different enough from our chosen professions that they opens up pathways to many patterns and strategies that we would otherwise not have access to.
A simple activity is to look at those around you that you consider successful, and ask about their hobbies. I guarantee you they’ve got a bunch, and if you show enough genuine interest, they may even share with you the would-be embarrassing ones to boot!
Hobbies make us interesting
Last but not least, hobbies simply make us interesting. Have you ever been stuck across the table from someone who has nothing apparent to bring to the conversation except for idle chatter about celebrity gossip, surface level understanding of and uninformed opinions of current events, and a mild penchant for talking about themselves in a thoroughly uninteresting fashion?
I have, and it was painful.
And as a result, I never want to be that person for someone else. Not only do hobbies make us interesting because they give us something to talk about, but because there is no pride in them, no excellence or worldly gain associated with them, they allow us to break down barriers, vulnerably put ourselves out there, and spark fun and creative conversations. They give us a natural avenue to have fun, to not take ourselves so lightly, and to invite questions and dialog with others.
And so my boys, my prayer for you is for you to have rich and full lives, filled with much joy, great connection, and loads of hobbies and interests so that you can not only be successful in the world, but can experience it to the full!
My sons,
One of the most basic instincts that human kind has evolved with is the instinct of fear. In much of our history, fear has been generally a good thing. When human beings were the smallest and weakest species on the planet, being fearful of all the other predators out there and keeping away from them was a good thing. That neck hair-bristling instinct, that sixth sense that allows us to know when danger is near has been an evolutionarily beneficial trait.
But we’re not in the wilderness anymore; quite the contrary, we’re now the apex predator on the planet. And just as our circumstances and place in the food chain have changed, so too must our understanding and application of fear.
What is fear?
Fear is defined simply as
“an intensely unpleasant primal emotion in response to perceiving or recognizing a danger or a threat.”
It can be triggered by both physical or emotional threats, as our body perceives both physical safety and psychological safety to be paramount to our survival, and therefore fires alarm bells when either are threatened.
In other words, fear is our body telling us that something isn’t right, that based on what we know, both intellectually and instinctively, we are under threat. It is a self preservation instinct, one that typically happens immediately before a fight or flight reaction, and it has served humanity well.
Fear in the 21st century
To really get a grasp of how fear impacts us today, it is worth us examining the different types of fear, and the responses that they elicit.
On one end of the spectrum, there is an understanding of fear that borders on the religious, the mystical. It is the notion of fear and reverence. This type of fear is closely related to respect, to awe, even to distant admiration. It elicits responses of deference, of thoughtful rumination, and of minimizing of the self. This type of fear is very useful as an overall collective society, as it allows us to see ourselves in all our imperfections and limitations, and can therefore promote collaboration and connection with one another.
On the other end of the spectrum is the gut-wrenching fear that closely neighbors terror, mania, and horror. This type of fear is debilitating, and often causes us to respond in a primal and instinctive fashion. Our fight or flight instincts are instantly triggered here, and we often are immediately moved to reacting instead of responding. It is an escalation where we go from zero to one hundred in an instant, and we throw logic and reason out the door and move straight to reaction. This type of fear has been evolutionarily beneficial, but is now arguably much less useful, and even potentially harmful for us as an overall collective species.
Good fear vs bad fear
Just as our more primitive ancestors had good fear and bad fear (ie fear of lions good, fear of puppies bad), we have to distinguish between good fear and bad fear in our modern times.
Good fear brings about good responses. It is a fear that brings us to positive action, that allows us to take steps to better our situation and circumstances. It motivates us to work hard, to take action, and to take ownership of our situations.
For instance, in business it is a good and healthy fear to fear that the tides will shift and the opportunity will pass us by. That fear causes us to work passionately and relentlessly to ensure that we don’t miss the wave, that we are able to overcome. In our personal lives it is a good and healthy fear to fear that our children will grow up very fast and that they will soon leave the nest. That fear causes us to allocate more time for them, to ensure that we build great and lasting memories with them, and to be thoughtful about the time we have left.
Bad fear causes us take instinctive reactions instead of thoughtful responses. It often brings knee jerk reactions that are not well thought out, and are generally bad for us in the long term. It causes us to be paranoid, to cower in its light, and to be paralyzed in our ability to move forward.
For instance, in business it is bad for us to fear that bringing bad tidings and news will be punished. That fear causes us to hide things from our teams, to try to cover our asses, and to spend time and energy making sure we avoid backlash and appeasing others instead of being productive and innovative. In our personal lives it is bad to fear that an action we take may bring retribution from our spouses or our partners. How many men live in fear that they can’t do the thing that they want for fear of the wrath of their wives? That is not a good fear, as it causes us to spend our energies avoiding pain rather than intentionally building up our relationships.
How to amplify good fear and minimize bad fear
So the million dollar question is how we can make sure we have ample sources of good fear in our lives and a decreasing set of bad fear? A few suggestions.
- Ensure you’re surrounded with emotionally healthy individuals. As the saying goes, “hurt people hurt people”. Surrounding yourself with emotionally healthy people is a great way to ensure that you don’t end up with bad fear because emotionally healthy people know that people make mistakes. They understand that life isn’t perfect, and they have the tools to effectively communicate through those mistakes.
- Regularly set aside time to see things in perspective. In business this means setting aside time on your calendar to take a step back and to examine your situation. Remove yourself from the equation and take a holistic, unbiased view of your surroundings. Learn to see the big picture and the longer story arc of your career. If you discover you’re working for an unhealthy manager or an unhealthy team culture, it’s probably time to start planning your exit.
- Practice positive self-talk. When we express fear and defeat, not only do we impact those around us but we affect our own perspectives as well. It is a well-studied phenomenon that the things that we say and express have a strong impact on our internal psychology and directly impact our performance. Make sure to practice expressing good fear with good intentions and actions to those around us.
I know this stuff is hard. It’s unfortunately not a subject that is ever taught. But I firmly believe that a life well lived is one that is intentional, that is purposeful, and that is based on the desire not to miss great opportunities instead of the desire to avoid pain. My sons, my hope for you is that you surround yourselves with people that model good fear and encourage positive, intentional, and thoughtful responses.
My sons,
One of my favorite games to play with you when you were young was the sleeping game. It was a silly little game that was designed to get you two to stay still and quiet for as long as possible. The game was simple - everyone lays down and sleeps, and the first to move around or to make noise loses. Not a very creative game, I know, but hey, I was a young dad who needed some peace and quiet, and you two were these tiny, loud, and rambunctious little things.
That didn’t change the fact though that I love sleeping. All my life, I’ve always loved sleeping. I slept a ton as a teen, and even as a young adult I’d spend Saturdays sleeping in as long as I can. The primary reason I loved to sleep? I loved dreaming. I loved the feeling of waking up from a wonderful dream and laying there, languishing in the feeling, trying to hang on to the last traces of it as consciousness permeated through.
One of the reasons I love dreaming is that dreams suspended reality. They allow my mind to build worlds, to create scenarios, to fully live out relationships and fanciful experiences that my real life didn’t enable. They open my mind, expand my horizons, and give me space to freely explore things that otherwise seem impossible. They provide an escape when I need, but most importantly they embolden me to think about the world as it ought to be, or even as it could be, instead of as it is. And then to do something about it.
Shaping our dreams
As I’ve looked back on my dreams over the years, I’ve recognized that they have been largely shaped by the inputs that I had in my life at any given time. The obvious (and probably mortifyingly funny) ones were the ones about girls. Yikes. My teenage years were filled with romantic flights of fancy with my crush of the day (and yes, there were many!). Combined with a healthy intake of rom coms (“She’s all that” starring Rachael Leigh Cook was my teenage favorite) and sappy love songs (“Kiss me” by Sixpence none the richer), I imagined many a sunset walk on the beach or a picturesque convertible joyride through the hills.
As I thankfully moved past those years, my college life of computer science, helping out younger class mates, and learning to ride motorcycles moved my dreams in those directions, and I found myself dreaming of working at Microsoft, of being an adjunct professor, and of exploring the continent on a motorcycle. Graduation brought dreams of success, of starting a family, of having two wonderful children, and of finding my place on the long road of adulthood.
But then a strange thing happened. I began to read more. I began to deviate my life from the daily grind, and began to fill my mind with books and with the ideas that those books brought about. While my childhood and adolescent reading was primarily filled with fiction which helped me dream of new worlds and encounters, and my regular, socially accepted inputs like watching Friends for a decade filled my dreams with common and relatable topics, in my thirties I started to really read. I read to learn, I read to grow, I read to become a better person.
Books like Mindset by Carol Dweck, The top five regrets of the dying by Bonnie Ware, When breath becomes air by Paul Kalanithi, Hit Refresh by Satya Nadella, and Infectious Generosity by Chris Anderson again shifted my dreams, this time in a much more elevated fashion. My dreams now turned to making an impact on our world, on figuring out how the world ought to be, and on finding my place and impact in it so that I could leave the world better than when I entered.
And slowly but surely I became convinced that we can shape our dreams. By controlling our inputs, by being intentional about the things that we exposed ourselves to, and by being staunch guardians of the inputs we allowed to influence us, we can guide and direct our dreams to topics and explorations of ideas that we want. Instead of allowing the activities of our subconscious minds to be governed by things like media (traditional or social), advertisements, and the general pessimistic and sensationalistic existence that is our societal norms, we can endeavor to shape and guide our unconscious thoughts and musings intentionally and according to the things that we value.
How do we do this?
We need to first recognize the impact that our daily experience has on our dreams. The environments we’re in, the worries that we have, and the set of activities we apply our efforts to in our conscious and waking moments all impact what our minds expand on in our subconsciousness.
One of the most beautiful characteristics about the human race is our ability to dream, to be inspired, and to find our own meaning and purpose for life. We do not merely exist and carry out our physical functions; no, we take those functions and try to assign meaning, to derive value, and to create joy in our experiences. The bigger we dream, the more our lives expand and the more rich our experiences become.
Dream big
So how do we then dream big? How do we get inspired, both consciously and subconsciously to take on bigger and better things? How do we go from a life that is rooted in the mundane experiences that our society places upon us - going to work, swiping up on your social media accounts, taking kids from place to place, and generally just running the rat race - to one that is uplifted, elevated, and expansive?
- Notice your posture. Have you ever noticed that we spend an inordinate amount of time looking downwards? Whether it’s physically looking down at our phone screens and the like or metaphorically looking down on other people and on situations that we judge, we spend a lot of our posture looking downwards. Look up. Look up at the heavens, at the grandness of the world above and beyond us. Look up towards the inspiring stories of those who strive to elevate life, to make our world better.
- Stop and smell the roses. We’re so busy with our lives that we never take time to rest, to have margin, to have space. When we force ourselves to smell the roses, when we turn our rat race running brains off, when we allow our conscious mind to lose focus and allow our subconscious to drift, we begin to rest. We begin to wonder. We begin to wander. We begin to dream.
- Read. I firmly believe that reading is the most important thing a person can do. If there is only one thing that you learn from me in our time together, if there’s only one thing I can impart on your lives as you grow, my hope is that you learn to love reading. Read books on life, on philosophy, on science, on generosity. Read biographies, fiction, exposition. Read for fun to enjoy a lazy afternoon. Read for study. Read to learn. Read to dream.
- Surround yourself with dreamers. We become like those around us. We adopt and elaborate upon the shared experiences with those closest to us. We can be lifted up, we can be anchored down. We can be inspired, we can be terrified. By surrounding yourself with dreamers and by creating times to discuss, to share, and to work out those dreams, we orient ourselves accordingly.
And so my boys, my hope for you, my dream for you, and my prayers for you are that you are dreamers, that you become men who both see the world as it is and as it could be, and that you be men of big dreams and even bigger actions to help us get there. I love you guys!
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,
We were made to dream. Before we even learned to speak and communicate, we learned to dream. There were a few sad nights when you little guys had nightmares, but thankfully those were the exception. More commonly we have beautiful dreams that inspire us, that soothe us, that excite us, or even embolden us to action. We were built to dream.
When you guys were little, you’d run around pretending to be firefighters, Air Force pilots, astronauts, or even professional soccer players. Children everywhere dream big dreams and run after them.
But for some reason, as we get older, we lose that. We get lost in the assembly line of adolescent preparation for adulthood and we lose sight of those dreams. We put them in a box, slap a “childhood memories” label on it, and stick it on the shelf, letting it collect dust over the years until it’s a long lost forgotten fragment of our younger years.
Gallup reports that roughly 20% of adults report actively pursuing their dreams, and only a third of those report achieving them. The rest of us go through life living uninspired, unambitious, and proper lives that are expected of us.
Sad, huh?
How does one live out one’s dreams?
It is easy (in comparison) to have dreams. It is much harder to live out those dreams, to run hard after them, and to pursue them with every fiber of our being. There are a number of things that can help make the journey palatable (and even possible).
1. Intrinsic motivation
When we were young, most of our motivation was extrinsic. Extrinsic motivators are motivators that are not your own, that are not core to your being. Things like parents pushing you, peer pressures, fear of falling behind, or even the communal pressure of living up to what’s expected of you.
To be clear, extrinsic motivators aren’t bad. In fact, they’re necessary for our survival and thriving as a society, and are a fundamental jump starter in one’s life. When we were young, our intrinsic motivators were for sleep, for food, and for play. Extrinsic motivators came in to motivate us to share, to collaborate, to learn, and to read. These are important.
Living out our dreams requires intrinsic motivation.
Intrinsic motivators are ones that you have internally, that are self-generated, and that are self-accountable. They are the things we do not because we want to do them, but because we feel deeply that we have to do them. They are a part of us. They are a part of our identity. They are an expression of our true selves, of the way that we believe we ought to live, the lives that we ought to have.
Runners don’t run because they want to reach a destination. They run because they love the run. They set their own distance, their own starting and ending markers, their own pace, their own goals. There is nothing external about that. It’s all internal. It’s all about you and what you want out of the run.
Intrinsic motivators are several fold more effective in maintaining focus, and in providing a lasting fuel to our industry. Because they are intrinsic, they need to be learned, practiced, and developed like every other muscle in our body. From an early age, children can develop the strength of their intrinsic motivators. They need time to play, to be bored, to wander, to try things out, and to discover those for themselves. By taking away all the freedom from their play and providing a ton of structure (ie here’s what you’re going to play, when, with whom, with what rules, etc), we rob them of the ability to figure that out themselves and in doing so figure out what their own intrinsic motivators are. The more we apply our intrinsic motivators the more strength they will have in fueling our endeavors.
When I was in high school, I had a number of high achieving friends. They were studious. They got straight As. They took advanced math classes and would school me on every test we had. They were bright, had creative ideas for class projects, and generally were earmarked for huge successes (at least, that’s what was written about them in our yearbook).
But once we got to university (yes, I’m Canadian, so we called it university… not “college” as the Americans do, or “uni” as our British friends do), they completely unraveled. Turns out without the ever watchful eye of Sauron (okay, okay, I’m a Lord of the Rings nerd… how bout eye of mom and dad then?) dictating their schedule and motivating them to do well, they had nothing to fall back on, no intrinsic motivation to get them through.
2. There is much beauty in the details
Great dreamers know that there is much beauty in the details. They, like great artists, know that the big picture is not enough. They know the secret ability that details have to generate great joy. They know that meticulously poring over every detail and painstakingly agonizing over every inch allows those who view the work to be uninterrupted in their experience.
It is one thing to enjoy driving. It is another to notice the smoothness of the gear shift, the refined but powerful roar of the engine, the accent stitching on the seats, and the amazing synchro alignment that allows downshifting to feel as smooth as butter. These details generate a richer and deeper happiness and connection with the car than simply enjoying stepping on the pedal and going.
This is true in every area of life. Whether we’re talking about the subtle hints of floral and fruity fragrances in the bouquet of wine, the refined brush stroke applied to a masterpiece, the technical complexities and details behind a seemingly simple everyday product, or the delicate lilt in the angel’s voice as she sings her aria, details and their recognition and appreciation are transformative.
As our senses are refined and heightened we begin to notice and appreciate each of the tiny details that make up the greater whole. This in turn allows us to be consumed by an experience, transported into a world where time stands still and there is simply the experience itself. And that, is a beautiful thing.
3. Sharing the gift
Passion is contagious. It is not learned, not cultivated, not given. It is inspired. It is sparked by others with passion. It can be a sudden ignition of an already-fertile ground, or can be the slow methodical rubbing together of sticks Boy Scout style. It is shared. It must be shared.
And so for the rare dream that does become a reality, for the one in a million dreams that is realized, we have a moral imperative to share it. When your dream becomes a reality, it doesn’t just belong to you. It belongs to the people who helped you - your family, your friends, your coworkers. It belongs to the world.
So share it. Share it for those who helped you get there. Share it for all those who may never have their own dreams realized, but want to be encouraged and uplifted by the stories of others. Share it as a testament to the power and beauty of the human spirit. Share it so that there is more light in the world than darkness. But most of all, share it so that you never forget it.
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!