This Month We Asked Harder Questions
The questions that matter most are the ones we've been avoiding
What does it mean to be truly free?
I've been wrestling with this question all month as I wrote some of the most challenging pieces I've ever attempted. Challenging because they demand honest examination of how we actually live versus how we claim to live.
This month became a meditation on our power to choose. Every post circled back to the same fundamental question: In the space between what happens to you and how you respond, what determines your choice? Is it wisdom or conditioning? Courage or comfort? Your authentic values or the crowd's expectations?
The more I explored this space, the more I realized how rarely most of us actually occupy it. We react instead of respond. We inherit our opinions instead of forming them. We perform emotions instead of understanding them. We follow leaders instead of becoming worthy of leadership ourselves.
The readers who engaged most deeply with these ideas were the ones willing to sit with uncomfortable questions.
Real growth doesn't happen when someone tells you what you want to hear. It happens when someone asks you questions you've been avoiding. When they point out contradictions you've been hiding from. When they challenge assumptions you didn't even know you held.
That's what philosophy is supposed to do. Not make you feel better about staying the same, but make it impossible to remain unconscious about your choices.
The questions we faced this month struck at the core of how we live.
Are you keeping the promises you make to yourself?
Are you pathologizing normal human experiences?
What does it mean to stay grounded when everything falls apart?
What makes someone worth following?
Are you confusing yourself with your emotions?
Which of your beliefs are actually your own?
Have you been mistaking numbness for strength?
These weren't comfortable revelations. But comfort isn't the goal. Clarity is.
The ancient Stoics understood that the examined life is not necessarily the pleasant life, but it's the only life worth living. They didn't develop their philosophy to feel good but to live well.
The difference matters more than we might think.
But perhaps the most powerful moment came when we confronted the illusion of “someday”. Realizing that time is finite turned vague philosophy into a personal reckoning with how we’re actually spending our lives.
These posts aren't meant to be read and set aside, but to be wrestled with, questioned, and tested against real life. My goal is to make philosophy practical instead of merely intellectual.
Thank you for your willingness to be uncomfortable. Thank you for questioning your own assumptions. Thank you for doing the hard work of examining how you actually live rather than how you wish you lived.
The conversations we've started this month don't end when the post ends. They continue when you close the laptop and face the choices that determine who you become. That's where the real philosophy happens.
September awaits with new questions to explore.
Stay stoic,
SW
"No matter how much one might want to confuse independence and freedom, these two things are so different that they even exclude each other. When everyone does what they please, they often do what displeases others, and that is not called a free state. Freedom consists less in doing one's will than in not being subject to that of others; it also consists in not submitting the will of others to one's own; whoever is master cannot be free, and to reign is to obey. (…) I know of no truly free will except that to which no one has the right to oppose resistance; in common freedom, no one has the right to do what the freedom of another forbids them, and true freedom is never self-destructive. Thus, freedom without justice is a true contradiction; for however one goes about it, everything hinders the execution of a disordered will.
There is therefore no liberty without Laws, nor where someone is above the Laws: in the very state of nature, man is free only by virtue of the natural law which commands all; a free people obeys, but it does not serve; it has leaders, and not masters; it obeys the Laws, but it obeys only the Laws and it is by the force of the Laws that it does not obey men. All the barriers which are given in Republics to the power of magistrates are established only to guarantee the sacred enclosure of the Laws from their attacks: they are their Ministers, not their arbiters, they must guard them, not infringe them. A People is free, whatever form its Government may take, when in the one who governs it it does not see the man, but the organ of the Law. In a word, liberty always follows the fate of the Laws, it reigns or perishes with them; I know of nothing more certain.
You have laws that are good and wise, either in themselves or simply because they are laws. Any condition imposed on everyone by everyone cannot be onerous to anyone, and the worst law is even better than the best master; for every master has preferences, and the law never does.
J.J. ROUSSEAU "Letters Written from the Mountain" 1764
Thank you for these words . I am going through difficult times. I have been asked difficult questions about me . Who am I ? I graduated from a high school that used the motto “ to thine own self be true !” Even then I was like “ what does that mean , what self should I be true to ? When I don’t know myself ? Even now ! I’m 72 , retired and should be enjoying ( I think ) my retirement and old age . But I’ve made decisions recently that have been very poor in hindsight , and caused chaos in my life . I am going to go back and read your previous posts. Sometimes I skip over them because of just too many emails . But the words you posted today resonated with me at a ( I hope ) perfect time in my evolving life . 🙏