Letters to my sons

A collection of thoughts and lessons I've learned along the way for my little men, and anyone else that's interested.

Posts tagged with #Courage

My sons,

Life is full of choices. Some are easy and seemingly insignificant (what should you eat for breakfast?). Some are harder (should you go to Vancouver this weekend?). Some seem huge and very hard (which college should you go to?). No matter what aspect of life you consider - be it work, relational, academic, medical - we will have hard choices to make. These decisions are hard because they are by definition not simple (ie there is no objectively measurable way to decide) and because the impacts of these choices will typically have a pretty large impact and reach on our lives.

Studies have shown that the average adult makes 35,000 choices a day, around 250 of which are made on just food alone (Wansink and Sobal, 2007)! As a result, it is in our best interest to ensure that we deal with these choices well. To do that, we need to consider a few things.

Understanding the role of emotions in our decision making

For the majority of people, whether we admit it or not, our emotions play a large part in our decision making. There are many that want to believe that they are completely logical, and that emotions don’t play a part in their decision making, but the reality is that we are an emotional and relational species. It is almost impossible for the average person to completely remove emotion from their decision making.

The exception of course, is the clinical psychopath, who actually has deficient emotional responses and a lack of ability to apply empathy to a given situation. Since the majority of us are not psychopathic, we need to understand that the biggest threat to good decision making is harmful emotions. Whether that emotion is fear, anger, pain, or shame, strong emotional reactions left not checked are a great threat to our decisions and to our learning.

First, we need to realize this. Many don’t have the self awareness to realize that their emotions are actually playing a large factor in their lives. For much of my life, I prided myself on the ability to think logically and make decisions based on that logic. As a computer scientist, that was an incredibly valuable trait. Personality tests also confirmed this bias (the typical software engineer tests as an INTJ as their Myers-Briggs personality type). It took much learning through painful trial and error and several rude awakenings for me to realize that I in fact am a highly emotionally oriented person that masked (and rationalized) much of that in logical thinking.

Next, we need to understand that these strong emotions prevent us from learning. Learning is often greatest in pivotal/crisis moments, and strong emotional responses left unchecked will push us quickly into fight or flight mode instead of allowing us to learn from the experience. Remember that the important thing is to acquire knowledge and have it paint a true and rich picture of the world in which you need to make decisions. That requires an open mind, something that harmful emotions prevent.

Learning before deciding

Once we foster an environment of learning in our lives, we can freely realize and accept that learning must come before deciding. In order to make the best decisions for our lives, we must realize that decisions ought to be the process of choosing which knowledge should be drawn upon from the variety of inputs and alternatives that we’ve thoughtfully considered, and not solely based on how we feel at a given moment. If we do not learn, then our pool to draw from is very shallow, and our decisions will be reflective of this.

Learning is the act of taking in many inputs, thoughtfully considering them, weighing them against our values and principles, and creating a strong basis for us to make decisions. The stronger that basis the greater our ability to not only consider first order consequences but second and third order ones as well, which in turn allows us to make better decisions and allows us to have more confidence in them.

This is why we need a range of experiences.

From having a diverse group of friends to being exposed to a wide array of ideas and thoughts, from trying new foods, sports, and experiences to spending time reading about topics that you’re not immediately interested in, building a wide range of perspectives allows us have a larger pool to draw from when we consider our options. This in turn allows us to make better decisions.

Have the courage to make the choice

It’s not enough however, to just know what the right decision is. Often the case with hard choices is that the thing we don’t choose has a negative impact on our situation, so we must be ready for that. The reality is that there will be benefits and consequences to every option that we consider, and often the best decision is one that comes with a lot of cost.

The second order implication is that not making the right hard choice may be less painful at the onset but often has a much more painful outcome in the long run.

And therein lies the rub.

We often think only about first order consequences to things and make our decisions based solely on those. The problem is that the second and third order consequences often not only have a more lasting impact but a larger magnitude of impact as well.

Consider an example.

You have a friend who has done something to upset or offend you. You have the opportunity to discuss the situation with your friend and share with them how you feel. What do you do?

The first order considerations for dealing with the situation is to consider the immediate conversation. This will be an awkward conversation, and may hurt your friend’s feelings. However the second order consideration is to think about the long term health of your friendship. Despite this being a difficult conversation to have in the immediate term, the long term benefits are that you will build a stronger friendship based on trust and honesty. The converse is that your friendship will suffer without the conversation, and will eventually fade into another one of those acquaintances that we all have many of - you know the type, where you politely say hi and make small talk when you occasionally bump into each other and avoid all depth and meaning in the relationship.

It takes courage to make the right decision.

And so my boys, I pray that not only are your lives characterized by much learning and a diverse range of experiences and inputs that lead to great decisions, but by the courage and fortitude required to make those decisions in spite of the cost of not choosing the alternatives. May you find the strength needed to choose well, and may you find the comfort and support needed to support your decisions.


My sons,

As a youngster one of my favorite Proverbs was Proverbs 3:5, which says “Trust in the Lord with all thine heart, and lean not unto thine own understanding”. As a good Christian kid, this meant that there were things that I was taught to do that didn’t make sense to me yet, but I had the full belief that in the fullness of time they would. That didn’t stop me from learning though, and trying to further my own understanding of the world.

I enjoyed the debates, the reading, the studying, the ruminating. I enjoyed diving into many subjects - English literature, philosophy, religion, science and technology, leadership. As I moved through college life, that enjoyment strengthened, and I often found myself having conversations late into the night with groups of friends and other students about many of these topics.

When I graduated though, I discovered that debating about virtues and philosophy and all those other things was very different than applying those things to my life. I found that peer pressure didn’t actually fade away; rather, it morphed into an unspoken expectation of how I was to live my life. The more I settled into the routine of “the rest of my life” after college, the more I found myself swept away by the guidance of the crowd.

What happened?

Adolescence and the quest for knowledge

Our society has structured the first two decades of modern life around the primary goal of acquiring knowledge and skills. Once we enter into our school systems, we are expected to move along on the conveyer belt of knowledge injection until we graduate from college with enough retained knowledge and, hopefully, some small amounts of gleaned wisdom and understanding to enter “the real world”.

The problem is that society got more complex. With the dawn of the information revolution, the number of highly manual and physical jobs decreased dramatically and was coupled with an equally meteoric rise of knowledge worker jobs (a knowledge worker simply is someone who’s main capital and profitable resource is knowledge). This meant that our traditional schooling systems designed during the industrial revolution with a goal of churning out workers capable of operating heavy farm machinery needed to adjust to producing graduates armed with enough knowledge to work in the new space.

These institutions were never designed that way, and have had a hard time adjusting to accommodate. Instead of simply needing to graduate with the ability to drive a tractor or to repair an engine, graduates are expected to have a wealth of knowledge in math, physics, basic engineering, chemistry, and many more. As a result, schools (and many parents) attempt to jam an insane amount of knowledge into the student’s mind, requiring pages and pages of homework to be completed nightly with regular tests and evaluations to ensure the knowledge has stuck.

Goodbye real life application. Goodbye learning and understanding.

The need to have your shit together

Armed with our budding belief that knowledge is more required than wisdom, we enter the workforce where we’re confronted with terms like “imposter syndrome”, “meritocracy”, and “high potential employees”. The set of expectations placed on us increases exponentially and strongly incentivizes us to lean on the knowledge of others, to listen to mentors and managers, and to “follow the crowd at chow time”.

Socially, we want to fit in. We want to be liked, to be admired, and to be respected. When we’re first starting out in our careers, a lot of times that respect gets tied back to what everyone is thinking a lot about; our careers. And so we play the dance, and try to sound like we know what we’re doing, and that we’re advancing and making career progress. We watch instructional videos with titles like “How to sound like an expert” and “How to speak with confidence”.

Pretty soon, our time for, effort in, and motivation towards our own stream of learning and our own exploration of ideas dwindles down to a drip, and eventually may dry completely. Slowly but surely, we then begin to rely on the understanding of others. We begin to mimic, to follow in their footsteps, and to set out on the path that someone else has laid for us.

It takes courage to use our own understanding

Hopefully, over time, each of us realizes the folly of this path. Some realize it earlier than others. For some, it is an awakening that happens early into their careers. For some, it disguises itself as a midlife crisis. For others, it is a sobering reality realized at retirement. Whenever that realization hits, each of us hopefully realizes at some point that living a life where one does not fully express, does not feel agency, and does not use their own understanding is a very unfortunate state to be in.

In her book “The Top Five Regrets of the Dying”, author Bronnie Ware shares that an all too common regret is the wish that one had the courage to live the life that they wanted, not the one that was expected of them. It takes courage to use our own understanding and to forge our own path because our world isn’t designed for it! Humanity has an evolutionary need to fit in, to stick together. But that needs to be balanced with a thoughtful and learned approach for applying our own wisdom and understanding.

A few thoughts as to why:

  1. Living life according to the herd is great (and even necessary) when the herd is in survival mode. The penguins of Antarctica shuffle around in packs, huddling together and rotating which penguins are on the outside of the pack so that they maximize warmth for the pack. In order to survive, they have to live according to the herd. If you’re reading this, there’s a high likelihood that you are not (or desire not to be) in survival mode and should therefore make your life choices with a view towards thriving.
  2. Growth, innovation, and enhancement do not operate at herd level. One cannot do the same thing day in day out and expect a different result. Therefore one must do things differently if one wishes to grow.
  3. Every leap of advancement in human history began with someone questioning the norm. Is the world really flat? Can mankind really only travel on the ground? Is the moon really out of reach?

Everyone who has ever accomplished something great has run into resistance, and has had to reach deep to overcome those hurdles. Whether they be in the form of naysayers, political opposition, or financial barriers, each of these hurdles shouts the same message: stay where you’re at; don’t rock the boat. The Japanese have a proverb that says “the nail that sticks out gets hammered”. It takes courage to overcome the hammering.

Taking off the training wheels

When we were young, our parents made many decisions for us. As we grew, we ought to have learned to develop a framework by which we could make our own decisions. Ancient cultures had rituals that marked the point in a person’s life when their tribe believed them to have learned enough to decide for themselves. This rite of passage often marked the transition to adulthood, where the individual was able to transition from being led to being guided.

For a variety of reasons many have not made that transition and still rely on parental leading instead of guiding and coaching. We must take off the training wheels. We must learn to have the courage to use our own understanding without the guidance of others. We cannot truly learn and understand if we are always taking direction and applying the directed knowledge instead of figuring it out ourselves.

My sons, my hope as your father is for you to a beautiful transition, one which clearly marks your passage into adulthood. I hope that I can lead you when you need to be led, but teach you so that you can learn to make your own decisions, learn to build your own framework by which you evaluate the world. Remember that learning comes before deciding! So learn. Read. Ponder. And have the courage to apply all that you’ve gleaned!


My sons,

We live in challenging and complex times where nothing is simple, nothing is exactly as it seems. There are no black and white situations, and there are no clear cut answers. Every situation we face has an immense amount of nuance that needs to be considered, examined, and thoughtfully understood.

This year has been packed full of hard stuff. Natural disasters. Racial tensions. Riots. One of the most polarizing presidential elections in recent history. One of the worst global pandemics in all known human history. Social isolation distancing.

These are all extremely complicated situations. And yet we can learn something in them, we can grow in them, we can flourish as a result of them.

Something I’ve been learning lately is that so much of the battle is just showing up. That simple act of getting off the sidelines, picking a side, and standing with your fellow men and women to take on whatever’s coming is immensely powerful. Make no mistake - the enemy (whoever you want to think of as the enemy, be it fear mongers, racists, bigots, homophobes, religious persecutors, or any other person or power that tries to diminish the nobility of the human spirit) wants us to stay idle. The enemy wants us afraid, lazy, lethargic, arguing amongst ourselves, or anything else that would prevent us from action.

Showing up is half the battle.

Here’s why.

1. We create a positive, forward moving mental state

So much of success in the arena is simply about moving forward. When we are still, the battle is lost. But when we are in motion, when we are fluid, when we are gaining momentum and focused on a goal, that is a beautiful thing. That motion, that movement, that momentum and inertia moves our lives forward and gives us courage to take on even bigger things.

Simply showing up is a victory unto itself, and however small that may be is enough to spark us into action.

2. We encourage others

The human spirit is strengthened by witnessing acts of bravery, of honor, of noble intent. When someone sees us getting off the sidelines and showing up in the arena, something deep inside them sparks. Regardless of whether that spark itself is enough to light a fire in them, us showing up and bringing encouragement to another is itself a powerful thing.

3. We show the enemy we’re not afraid

So much of the world is shrouded in fear, in misdirection, in misinformation that leads to inaction. By showing up, we show the enemy that we’re not afraid, that we’re willing to stand shoulder to shoulder in the arena and take on what’s coming.

So my sons, my prayer for you is that you too would show up. That you would move life forward, that you would encourage others and find others of like mind to fight together with, and that together we can stand up against the injustices and the abominations of the world. For together we stand; divided we fall. I love you boys.


My sons,

It’s easy to look at the world around us and see its many flaws and many weaknesses. It’s easy to see the hatred, the racism, the sexism, the anger, the suspicion - it’s easy to look at all that and decide to keep your head down and mind your own business.

And no one would fault you for that.

We live in a world where people are expected to cower, to keep their voices down, and to do the bare minimum to appease their own consciences, often with little to no impact.

I implore you to choose a different path.

I recently read a beautiful speech from the 26th president of these United States, Theodore Roosevelt, which has since come to be known as The Man in the Arena. It reads:

It is not the critic who counts;
not the man who points out how the strong man stumbles,
or where the doer of deeds could have done them better.

The credit belongs to the man who is actually in the arena,
whose face is marred by dust and sweat and blood;
who strives valiantly; who errs,
who comes short again and again,

because there is no effort without error and shortcoming;
but who does actually strive to do the deeds;
who knows great enthusiasms, the great devotions;
who spends himself in a worthy cause;

who at the best knows in the end the triumph of high achievement,
and who at the worst, if he fails, at least fails while daring greatly,
so that his place shall never be with those cold and timid souls
who neither know victory nor defeat.

Yes, there are many ways in which we have fallen. Yes, there are many unspeakable acts and unimaginable crimes that have been committed, and even sanctioned in our lifetimes. Yes, we are surrounded by imperfection in this fallen world.

But let us stop standing on the sidelines watching idly as others struggle and fight in our stead. Let us never stop picking ourselves back up and getting back into the arena. Let us fight for those who cannot fight for themselves. Let us speak up for the voiceless. Let us defend the defenseless. Let us bring hope to the hopeless.

Let us let shine the nobility of the human spirit; that spark within us that when pressed enables us to stand courageous with a courage we didn’t know existed.

I love you, my boys. I pray that when you are old enough to understand these words, that you will find your father in the arena, that he will be standing side by side and back to back with men and women that he loves and loves him, and - most of all - that you will join them in the arena and fight together.


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