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.

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!



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