Apostoic

An excellent mental exercise, rooted in Stoicism, is to start at the high level of the activities that make up the lion’s share of your daily efforts. Select one that you would rate as being highly important, write it down on a piece of paper, and then ask the question: “Why? Why do I do this?” Given the unbelievably expensive nature of attention, why do I select this thing and place it above all the other things I might do with the time I have? You are going to begin to plumb the layers of conscious and then subconscious reasoning behind your constant engagement in this activity. You will uncover much by doing so, gain a better understanding of yourself and what motivates you, and if need be, make some life-changing adjustments through self-reflection.

The first layer down, you should pretty easily be able to give a reasonable answer to why you engage in this activity, one that is fairly surface-level and seemingly obvious. With that answer on your brain and on your paper, quickly test its logic and its moral compass. Is this a logical thing to do? Is it aligned with what is good and right? Does it help or hurt me? Does it help or hurt others? This assessment need not be delved too deeply just yet. Quick answers will do, and the reason that first comes into your head is probably the correct one. Once done, ask “why” a second time, this time examining the first and most obvious reason behind your activity. Ask yourself why this reason should merit the unbelievable expense of attention, taking precedence over so many other reasons and motivations that one might have.

See if you can go another level deeper into the abyss of your motivations. This will be slightly more thought-provoking, but still not difficult at this level. With a newly identified reason for your reason, test this for logic and morality as well. Then keep going. While this Stoic exercise will progress in difficulty as you begin to near your core motivation, apply yourself diligently and honestly to it, and eventually at the bottom of all of your self-inflicted, childlike “whys?” you will arrive at an absolute. You will arrive at a bottom line of reasoning which is self-containing, the very bedrock of your motivation. If you have never done this before, it may be a highly enlightening experience. You may learn a great deal more about yourself than you previously knew through this philosophy. Done correctly, you should discover one of two possible outcomes. (1) This core driver is both logical and aligned with the highest good. (2) It is illogical and rests on shaky moral ground.

If the former, great. Carry on about your business. If the latter, it may be time for some deep thinking and realignment of this core driver, which is going to require some spiritual and mental work. This realignment has been given many names: Self-improvement, soul searching, attitude change, mental adjustment, a change of heart, to name a few. Whatever name you’d like to give it, I would posit to you that there is no fundamental difference between this and the Judeo/Christian concept of repentance. You are analyzing your own thoughts and actions for alignment to what is good, useful, and beautiful, attempting to identify where you are going astray in that pursuit, and then resolving to make a new attempt to change that thought or behavior starting from its root—a hallmark of personal growth in Stoicism.

The Time-Tested Tree Illustration in Stoic Philosophy

Envisioning a tree is helpful in understanding this Stoic exercise. If you have a tree in your backyard that produces a mix of good and bad fruit, you might start by picking off and discarding the bad. Engage in this for a season and you will have a tree with a greater ratio of good fruit on it; however, this will do absolutely nothing in the line of improving future production. The following year, the same good and bad fruit will appear, and you’ll need to do it all over again. You might instead notice that some of the branches are diseased and rotten, and busy yourself with removing the bad branches to give more nutrition to the good ones. This will certainly get you a little further, but the tree that produced bad branches is likely to produce more, given time to grow them. So you keep going, eventually deciding to dig around the tree and check the health of its roots. Here you finally discover a rotten, diseased root buried among the healthy. With great care, you set about removing this without harming the good, healthy, thriving roots. Finally, you have addressed the real issue at its heart, and your tree can once again make progress toward the future you desire, a bountiful harvest of nothing but good fruit—a vivid metaphor in Stoic philosophy.

Unpacking your Daily Efforts with Stoic Self-Reflection

Now that the exercise is well understood and illustrated, let’s examine a realistic example. Let’s say a man is heavily engaged in seeking a higher salary through promotion at work. 62% of his waking hours are given over to this chase (10 of 16 hours). When one promotion is achieved, and his salary is increased, he is happy. But, he realizes, this happiness trends toward the temporary rather than any lasting and solid contentment. When his salary goes up, his spending goes up, and he finds himself very soon pursuing the next promotion and the next salary increase. This cycle carries on for 20 years of his life, but eventually he stumbles across this article or something similar, and the spark of self-reflection ignites. He decides to begin plumbing the depths of this pursuit, and the desire erupts for the first time to find the root motivation. What drives him to choose this engagement over the myriad of other engagements he might choose? What makes this sacrifice a good one, if it is a good one?

 He asks his first “why?”

Question: “Why do I want the next promotion?”
Answer: To make more money.

He tests this answer for logic and alignment with the good. On the surface, he decides that wanting more money is logical. If you want to buy more or better things, you need more money. If you want power to do more in life, you’ll need money. Therefore, engaging yourself in getting more money is logical on that front. But is it good? He isn’t quite sure. He decides that the goodness or badness is dependent on how the money is used, so he asks “why” again and goes down another layer—a Stoic method of inquiry.

Question: “Why do I want more money?”
Answer: I want more and nicer things.

Once again, he pauses to examine the answer. Is it logical to want more and nicer things? Maybe yes and maybe no. If he were a man struggling to feed his family and put a roof over their heads, the answer might be yes. It is his job as a provider to ensure that his family has its needs met, so if the basis were need, he would be behaving both logically and rightly to strive to provide more food if his children are going hungry. If his family is cold, it would be good to provide them with more clothing. However, this man has decided to be honest in his engagement with this self-reflection exercise, and not to lie to himself. He assesses that need is not the driver of his motivation, but rather want. He goes down another level.

Question: “Why do I want more and nicer things?”

Answer: I want others to admire me.

Now, this was a very difficult thing for him to admit. To get there, he envisioned himself driving a nicer car than the average person can afford. In doing so, he had the revelation that while driving this car, the pleasure will not come from the car itself, but from the eyeballs pointed in his direction. The last person alive in a zombie apocalypse doesn’t care how nice his car looks. The value of a good-looking car is entirely hinged on the existence of other peoples’ opinions. While driving the car, he would be inside, focused on getting from point A to point B. He would not be outside, admiring its beauty. Fundamentally, nothing will have changed for him. With his current car, he goes to work and the grocery store. With a more expensive car, he would still go to work and the grocery store, but more people would admire him while he does it. He swallows hard. He tries to go down one more layer.

Question: “Why do I want others to admire me?”

Answer: Other peoples’ respect is one of the things I want most in life.

This is not the core motivation for everyone who needs to buy a new car. However, committed to honesty in this Stoic exercise, it is the motivator at which this man arrived. Notice that the question and the answer are now inextricable. We have reached the rock-bottom level, the level in which the reason is self-containing. But we aren’t quite done. Now comes the most difficult thing of all. Now we’re going to analyze this core driver, this bedrock of motivation, for alignment to what is wise (logical evaluation) and alignment with the highest good (moral evaluation)—a cornerstone of Stoic philosophy.

Testing Logic in Stoicism

Epictetus writes about the folly of pursuing acceptance and admiration from people whose lives, values, and choices are not what you wish to emulate. You pull into the grocery store parking lot in your fancy new car. Who is most likely to call out “sweet car dude!” Will it be the wizened, aging grandmother or grandfather who have given their entire lives in sacrifice to their children and are now living out their days in quiet simplicity, shopping at Aldi, sharing fun and wisdom with other people’s children in their church or community? People who were wise with their money but did not live for the pursuit of possessions. Instead, they understood their wealth to be for the purpose of good service they could do for their loved ones. They have no appearance of affluence and live a simple, humble life before God and man. Are they going to give you the attention you so crave? Likely not. Are these people worthy of your respect and admiration? Likely so. Instead, you will probably get the attention and envy of the young and foolish, who spend their days in pursuit of fashion, style, and selfishness. High schoolers, college students. Young, career-driven, money-loving clowns who worship the god of appearance. In other words, punks and fools. Are they going to give you the attention you so crave? Much more likely. Why would you want it? Why would you want the acceptance and admiration of people who have never done anything noteworthy or admirable in their lives, who have never sacrificed their pleasures for the good of others, who have never stopped looking in the mirror or squabbling for social status long enough to realize that their life is pointless and useless. Why?

Desiring the respect of people whom you do not respect is completely illogical.

Testing Morality in Stoicism

Beyond the practicality of need, the morality of a purchase needs to be examined by opportunity cost. Almost all of us could be wealthy. Most of us are never going to be wealthy enough to maintain the appearance of wealth AND be wealthy. The money spent in pursuit of other people’s respect and envy could be invested and used to produce real wealth. Do this over a long enough time period and you’ll be able to help those in your life that need it. You’ll be able to give your daughter and her young husband a starter home or pay their enormous medical bill. When someone in your church or community has the desire to rescue a child out of the foster care system, you’ll be able to fund their adoption. The real value of money lies in the good it can do in the world. On the basis of this opportunity cost, buying respect is not in alignment with the highest good. Buying wealth is, if it’s going to be used well. How much real wealth could you have built if you had never made a monthly car payment in your life, instead choosing to drive practical used cars purchased in cash?

Now, this examination does not necessarily show that you should never spend money and enjoy life. Rather, it suggests that you examine and correct what your “enjoyment” is through self-reflection. Choose to enjoy what is good. Choose to take no enjoyment from that which is illogical and useless.

Digging to the Core: A Stoic Path to Wisdom

The discipline it takes to ask why all the way to the bottom level takes time to achieve. Begin practicing with those activities that make up the greatest part of your effort and time. You will discover things about yourself that you never knew. You will find motivations that are aligned with what is wise and what is good. You’ll find others that are not, and you’ll have the opportunity to change yourself at the very core. This is what true personal growth is about in Stoicism. We are not seeking to improve our ability to get what we want. We are seeking to improve what we want. In doing so, you may find yourself accidentally becoming content.

Call to Action:

This exercise just handed you a shovel to dig straight to the rotten roots of why you chase what you chase. What you’ll find down there might change everything. If you’ve ever wondered why temporary wins never feel like enough, send this to the friend whose life looks perfect on the outside but exhausted on the inside. One honest “why” chain could be the start of real contentment. — D.S. Cook

https://apostoic.com/2025/03/10/the-art-of-asking-why-a-stoic-exercise-in-self-reflection-and-personal-growth/

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