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 2026
My sons,
We live in a world that expects instant results. Whether it is startup life where companies are expected to achieve 8 figure revenues in their first year of existence, corporate life where employees are expected to turn around problematic behaviors or troublesome team dynamics in the next quarter, or personal life where we expect same day delivery, instant meals, high speed wireless internet, and every other instant gratification method we can think of, our world has been barreling down the path of bigger, better, faster, and more instantaneous.
In such a cultural dynamic, it is often difficult to pause, to take the time to think, and to expend the effort required to make decisions that are holistic and focused on the long term.
The value of patience
Fortunately, with a little bit of effort to expand our field of view, we can find many examples of outcomes that were only made possible with persistence, grit, and a steadfast commitment to stay the course. A number of age old adages come to mind:
“Rome wasn’t built in a day” “A journey of a thousand miles begins with one step” “Slow and steady wins the race”
Every one of these points us to the fact that nothing truly great can be rushed. Whether we’re talking about industry changing products, society changing cultural adjustments, or even life changing romances, every single thing that lasts, that is remarkable, that is revolutionary takes time.
Constant, gentle pressure
When I was younger, I believed in the epic moment, the great reveal, the climactic prestige. Everything around me pointed to it, and much of my surroundings and inputs led me to place a lot of value in it. Hollywood taught me that no matter how dire things got, a grand gesture (romantic or otherwise) can save the day, repair a relationship, or turn the tide of battle. I was repeatedly fed the myth that a hero could take any bad situation - a failed relationship, a lifelong rivalry, a generations-old conflict - and completely turn it around and be victorious. And they could do it in style, with a flair that was immediately daring and yet attainable, and all in the movie goer friendly timespan of two hours. Cue the credits.
Sadly, real life doesn’t work that way.
Real life works over the span of a lifetime. It works through the duration of a career, over the course of one’s academic tenure, and over the full cycles of our economic process. It requires a collection of little things, of the steadfast and persistent determination that is willing to do the unglamorous, of the grit required to slog it out. Not some heroic flash bang effort.
Success in real life requires constant and gentle pressure.
Slow cooking my steak
I love steak. When my brother got his first paycheck at his college internship, he took my parents and I to Ruth’s Chris steakhouse. While I’ve never solved the mysteries of who Ruth is, and what a “Chris steakhouse” is, that experience got me hooked onto steak for life. Throughout my young adult years I ventured into as many steakhouses as I could afford, lucky as I was to have work pay for many of these experiences in the guise of a work trip (I’ve been to every steakhouse in Cedar Rapids Iowa, Boulder Colorado, and even Mountain View and Sunnyvale California).
As I got older and became more financially responsible, I decided to learn how to recreate these culinary delights myself. I went through all sorts of books and articles, watched any number of master chefs argue for their method being the best, and experimented with everything from the reverse sear to direct grilling to baking and using my Searzall.
But then one fateful day during the COVID pandemic, I discovered the Sous Vide, and my life was changed forever. Picture perfect steak, cooked consistently all the way through, every single time. Heaven. The secret? Constant and gentle pressure. Well, constant low temperature water bath anyway. But you get the point.
The small things
As a dad, I’ve discovered that model to be an extremely effective one that works across a myriad of scenarios raising my children. My son now pitches for his select baseball team. But 6 years ago when we started, he hated baseball. Never wanted to play catch, didn’t want to go to practices. But over those years, several times a week I’d coax him outside to throw 20 balls with me each time. Slowly - painfully slowly - he started coming around to it, to the point where much of his identity is wrapped up in baseball, in his team, in his development.
Constant, gentle pressure.
As a leader and a manager, one of my strengths is in building great teams. We live in a world where nothing meaningful can be done on one’s own. Everything requires teams, and the more effective the team, the better the outcome.
A technique I stole from the late great Bill Campbell is the practice of starting every staff meeting with 90 seconds around the room of non-work stuff. There is much research that has shown that the greatest teams are the ones that have a strong amount of psychological safety. The root of psychological safety is trust and vulnerability - you need to trust that when you share your open and honest view that your teammates will respond well, regardless of whether they agree or violently disagree with the point at hand. Freedom to express without fear of retribution.
How do we build trust and vulnerability? By getting to know each other on a human level. Turns out when you hear 90s a week about a person’s life and you engage with them on those small tidbits, over the course of a year or two, you’ve actually gotten to know quite a lot about that person. I now know more than I could have imagined about fishing, about the types of gear, the different techniques, when one fishes from a boat vs shore etc, and I’ve never held a fishing rod in my adult life because every week for the better part of 4 years, one of my teammates would tell us all about his fishing adventures.
Constant, gentle pressure.
Turning on the pressure
A few thoughts on how to effectively start your own slow cooking process:
- Be transparent about your intentions. Whether you’re looking to improve the effectiveness of your team, to teach your children some great habits, or to elevate the conversations of your friend group, being transparent about your intentions up front is crucial. No one wants to feel hoodwinked, and if your intentions are good, generally you’ll get people to lean in simply by sharing with them what you’re trying to do.
- Start small. Remember, it’s gentle pressure. In his book The Power of Habit, Charles Duhigg shows us that the way to change our habits is to start small. Want to lose weight? Don’t start by trying to cut out all your favorite snacks and move to green smoothies. Start simply by stepping on the weight scale every morning after you shower.
- Be consistent. Whether we’re talking about raising children, growing teams, or managing customers, consistency matters. A lot. If you’re a notoriously chaotic person, then you’ve got to develop systems that will help you maintain that consistency despite your personal working style.
We see this phenomenon in nature as well. Places like Antelope Canyon in Arizona are breathtaking in their natural beauty. It took hundreds of thousands of years filled with flowing water, windblown sand, and natural erosion to produce something so marvelous. Let’s take a page from mother nature’s playbook and apply that same constant, gentle pressure to the beautiful things that we endeavor to build!
My sons,
The age of AI has brought with it many conveniences, productivity improvements, and new capabilities. Those that have wholeheartedly embraced the AI native life have seen drastic changes to every facet of their daily experience. Not only has AI changed the pace at which we do things, but for AI natives, it has changed the very nature of what we do, and has brought so many things that were once impossible within reach.
Gone are the days of needing to spend countless hours poring through bespoke documents to gain understanding, or the days of requiring a doctor to help diagnose a wide range of common maladies. Didn’t study graphic design but want to create beautiful and professional custom images and photo edits? AI can do that for you. Didn’t study music composition but want to record a song of your choice complete with full instrumentation? No problem.
Sounds magical, doesn’t it?
The dangers of magic
It is very tempting to outsource more and more to our AI agents. Model builders are consistently and rapidly outdoing one another with more powerful, more capable, more flexible models being released at a blazingly fast cadence. New capabilities are popping up everywhere. From reading and summarizing your documents to crafting responses to emails, from calendar management to creating and scheduling events, from building powerpoint presentations to writing code for you, these agents are no longer simply automatons that do exactly as they’re told.
Through the magic of large datasets and huge power-thirsty data centers, agents feel intelligent. They seem to be able to apply thoughtfulness, reasoning, and even empathy and compassion in their interactions with us.
And they’re helpful. Oh so helpful.
Agents seem like the perfect companion for us - super capable, very obedient, able to “remember” our preferences, able to adjust themselves at our whim. And so before long, we find ourselves depending on them, offloading more and more of our daily productivity to them. This is all fine and good, as long as we vehemently keep one thing in mind:
We cannot allow agents to replace our thinking.
It’s a slippery slope to go from asking the agent to put together a framing document for you to complete to asking the agent to write the document for you altogether. But if we give up our thinking to the agents, it’s game over.
The last bastion: writing
Writing has always been one of modern man’s superpowers. Not only did writing allow our ancestors to communicate thoughts and ideas at a scale never before possible, its very medium forced them to slow down and to carefully consider that which they were writing.
In its early forms, writing was expensive - ink, parchment, quills, storage - all of these were cost prohibitive, so they naturally steered us towards deep thought. As the cost of the medium dropped (we have the printing press to thank for that), the value in the thought behind the words steadily rose.
As AI improves and threatens to subsume our thought, we have an existential requirement to resist. We must resist the urge to have AI writing on our behalf for fear that it will silently expand to take over thinking on our behalf.
The benefits of writing
While there are many perils to outsourcing our writing, there are a number of outsized positive benefits to doing the writing ourselves.
- Writing forces clarity. Writing narratives is hard. Weaving the story in a coherent manner requires skill, practice, and effort. This is a good thing. The act of writing will force the writer to think and to synthesize much more deeply than any other communication mechanism.
- Writing increases information density. By writing long form prose on one’s own, one is forced to truly understand a given topic before putting it to paper.
- Writing tells a story. Storytelling is how our species communicates and inspires. Crafting a narrative requires the writer to deeply understand how the various points intersect so that they can take the reader on a journey.
As our world becomes more automated and runs at a daily increasing pace, it is tempting to lean further and give up writing. Resist that urge. For it is only by holding firmly to the thing that is uniquely ours - our thoughts - that we continue to stay in the drivers seat. It is only by thoughtfully crafting our words that we are able to inspire. And it is only by inspiring that we are able to change the world.
My sons,
On every playground in every school, in every city, in every country in the world, one of the most common phrases heard on a daily basis is this:
“That’s not fair!”
From an early age, we develop this sense of fairness, this belief that the world is supposed to be fair. We believe it so deeply that when we perceive something to be unfair, we throw on our biggest frown, stamp our feet, and in as loud a voice as we can muster let it be known that we have been wronged.
Problem is, the world isn’t fair.
Everywhere we look, things are not fair. There is no equalizing force that blankets the world in fairness, that spreads wealth precisely fairly to every human being, that gives the same number of opportunities to each candidate, or gives every 5 year old the same number of cupcakes for every birthday party. There is no cosmic force that gives every person the same number of years on this earth, that protects everyone in equal measure from the illnesses of life, or bestows the same gifts and talents to each individual person.
That’s just the personal stuff. The work stuff is even worse. If life itself isn’t fair, work definitely isn’t. Some people are given more opportunities than others. Some people are (to us) unfairly and undeservingly promoted. Some people seem luckier than those around them. The sooner we accept and embrace the fact that the world isn’t fair, the sooner we can take the next step; learning how to capitalize on that unfairness.
Power
These days, the word power tends to carry a number of negative connotations. Power is associated with folks who abuse their station, with bad actors taking advantage of those over whom they have power, and with depictions of power hungry and ruthless characters. While those are accurate depictions of the nefarious, they do not define power, and are not an inevitable conclusion.
Strictly speaking, power is the capacity to influence outcomes. That’s it. Nothing sinister, nothing negative implied. It is simply the capacity that a person has to have influence over the outcomes surrounding their situation.
With that definition, don’t we all want power? Doesn’t every person want the capacity and ability to influence their situation, their environment, and their outcomes? Especially when it comes to our professional endeavors, don’t we all want to be able to positively shape our outcomes?
In his book ~7 rules of power~, Jeffrey Pfeffer posits that power is not only one of the most misunderstood concepts in our modern world, but is the one that has the greatest influence on our lives and our livelihoods. Power dynamics happen in all relationships - professional ones, social ones, friendships, and even familial relationships. As such, it behooves us to better understand what it is, how to build it, and how to learn to use it for our own purposes.
Ways to attain power
In general, there are two methods that one can use one’s efforts to attain power.
- Working hard, being helpful, working for the greater good of the community
- Spending time on political advancement, self promotion, and building helpful social relationships
Studies have shown that there is a social class difference in each method. People from lower class backgrounds typically gravitate towards the former as a baseline. Power tends to flow to those that bring the most to the community, and even those that hold the political power of the community maintain that power by ensuring they continue to provide the most benefit to it. People from upper class backgrounds have a stronger propensity towards politics and often place a higher emphasis not on what you can do but rather on who you know. Power tends to flow to those who are the most connected, and much emphasis is given to currying favor with those more powerful than yourself.
Interestingly enough, people in lower classes are reluctant to use political power because they feel like it advances the self and not the community. However, when posed with a situation where using political advancement would help others, the class differentiation disappears and people in lower classes were willing to tap into that political power as well.
Harnessing your power
Independent of how you attain power is the question of how you harness and utilize it. We need to assume from this point out that each of us has to decided we are not going to “play fair” and no longer want to be a bystander in this game, playing the game as it is. If we want unfair results (ie rising to ranks higher than we might have otherwise, or faster than our peers, or faster than “the market norms” would otherwise dictate), then we have to learn to play unfairly.
As a Chinese Canadian, I grew up immersed in the ethos of keeping one’s head down, working hard, being loyal and reliable, and playing by the rules. There was an enormous amount of social pressure to stick to the plan, to color within the lines, and to do the respectable thing. Advancement meant working harder, longer hours, and being more dedicated than the next hardworking person.
The problem is that rising through the ranks, keeping your head down, and simply doing the work is not the optimal way for most people in this day and age to achieve the success that we’re all looking to have. The rules were made by those with power, almost certainly to ensure that they stay in power and no one disrupts that. How do we add to our hard work an understanding of power so that we can move from getting fair (or often, negatively unfair) results to getting positively unfair ones? How do we harness our power and utilize it for our benefit?
1. Understand and leverage your unique talents
I’ll never forget the first truth bomb my legendary Econ 101 professor Larry Smith uttered on the first day of class. “Look to your left. Now look to your right. By the end of the year, one or both of those people will no longer be here.” The reason? They were there because they thought they ought to be instead of being there because they loved it.
In the age of AI, finding our unique talents becomes increasingly difficult. AI has drastically lowered the barrier to entry for many things such that it behooves us to really dig deep to find our moat. This moat will certainly not be something we’ve picked up in the last year. It will not be a piece of knowledge or a single experience we’ve had, it won’t even be a cool new skill we’ve learned. It’ll be something much more complex and deeply engrained than that, and will definitely combine the set of our experiences and motivations.
This quest of self discovery isn’t easy. There are pitfalls, there are obstacles, there are even possible mid point conclusions that there is nothing unique about us. But if we want to harness the power that is uniquely ours, we’ve got to have the perseverance to push past those, to push past the life framing that others have for us, and to get at the heart of who we really are.
2. Move around
We are no longer in the age of the “Company Man” - you know, the circa 1940 way of life that had people join a company right out of college and retire on a pension there. Nowadays, 5 years is considered a pretty long time to stay at a single company, let alone a single team, and for good reason.
First and foremost, our world has gotten infinitely more complex, and as a result there is great need for folks with range. There is much research around the concept (if you’re interested, read Range by David Epstein) that shows how our brains subconsciously connect the seemingly disparate set of experiences we’ve had to produce more rounded and holistic decisions. Turns out the best leaders are the ones that can pull from a wide range of experiences and bring them to bear on their current work.
Next, moving around provides infusions to the growth of our network. As we discussed above, our world is increasingly impacted by those with strong networks, and moving around gives us an unnatural boost.
Lastly, with each move we take on an enormous amount of learning. The phrase “drinking from the firehose” is a common vernacular used in the tech industry to signify that someone is in the middle of a deep time of learning. That repeated firehose learning has an outsized impact on the power we have and on the value we bring to any organization.
3. Network
This one deserves some exploration. When I was younger, I used to hear this all the time. “Sam, you’ve got to network, you’ve got to go to these networking events and meet more people”. I hated them. From alumni events to tech meetups to conferences, I went to them all and dreaded them. I’ve since learned that not only was I doing it wrong, I was also missing the skills to get any benefit for it.
Networking doesn’t mean just meeting people. It means making a meaningful connection with someone such that there is follow up and follow through. It means maintaining that connection and nurturing it over time. This not only takes time and intention, but also takes skill.
Remember that networking is a two way street. The other person’s got to want to maintain a relationship with you as well, so you’d best have something to offer before you bother meeting them. This again, requires work. Intentional work. Their time, like yours, is valuable, and they’re not going to want to waste that time on a dead end relationship.
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Each of these is itself a topic that we’ll go into more detail in the future, but for now, suffice it to say that the world is not fair, but by intentionally learning and developing a few new skills we can skew that unfairness in our favor.