Question from a reader:

Why do we tend to crave/desire/pursue a path that doesn’t necessarily makes us happy? How come the external success (money, speed- race results, etc.) we work so hard for (both mentally and physically) does not lead to us being happier? Why does that disconnect which you wrote about it exist? How come external success is an illusion?

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I’m going to share some insights but much better would be to read Thinking, Fast and Slow as well as Seeking Wisdom. It takes effort (that most will never make!) to understand those books. The knowledge you gain will serve you, and your family, very well. Applying the knowledge in the books has saved my family time, money and suffering.

To kick off, not everyone makes poor decisions – I make poor decisions in some areas and excellent decisions in other areas. So consider the specific area where you’d like to improve. The areas where I make poor decisions (trusting too much, character) have been the same for many years. Knowing my blind spots, I make those decisions more slowly and take advice from my wife (much stronger in that area than me).

I accept the fact that my family is going to make mistakes – what we want to do is share the knowledge from our mistakes, write it down, and remind ourselves of the mistakes in our family’s history. I also want to make sure that we evaluate decisions based on the information we had when we made the decision. Written records such as file notes, investment summaries, budgets and strategic plans are essential to learn from decisions and evaluate the quality of those choices.

You mention happiness – my most important technique is to write down the characteristics of my “good days.” The simplicity of these days amazed me – because they were so simple, nothing stood out and nothing was remembered! The pleasure of quiet serenity disappears into the background stress of a busy life. 

Because I know that the media doesn’t understand what makes me happy, I do my best to limit media sources. If you look deeply at the source of the goals that leave you most disatisfied then you’ll often find a root in our popular culture, reflected in all sources of media (most toxic are popular culture, anonymous forums and tabloid journalism – we must ditch these when self-esteem is an issue).

The happiest weeks of my life are when I disconnect and exercise with my wife in nature. I share this observation because it is the purest form of my athletic motivation and I don’t need to win, or even attend races, to achieve this goal! A big motivator for my current restructuring is arriving at a point where I can greatly reduce connectivity. So far, I’ve managed to break free from Facebook and greatly reduce email time – thousands of (serene) hours will flow into my life from these two changes.

Think deeply about endurance sports and you may see that it is the time alone, and the exercise, that drives the psychic reward. It’s not the achievement. 

With athletic goals, I’ve released myself from the expectation that ANY goal will ever make me happy. This is very different from focusing on a thought that achieving goals will never make me happy. I’ll explain.

If the goal is happiness then focus on what makes you happy… …working towards goals that create a life with meaning.

Goals provide incentives to create a way of life via structure. Structure, routine and directed work (resulting in progress) create meaning. Making the transition to seeing “a way of life” enabled me to take a holistic approach to athletics. If the goal is an incentive to follow a path then the game is about the “how.” I have many roles… husband, father, teacher, coach, writer, employee, custodian, fiduciary… I meet my commitments to those roles while working towards my goals. I’m cautious about making commitments and stubborn about keeping them.

Even if goals are illusory, even if they won’t bring happiness in themselves, even if I’m going to want something different in ten years times… my current life is far better when I am engaged in a project that creates value for myself, and my inner circle.

The key is to think deeply so that I choose wisely.

That’s the purpose of my writings.