Freedom is Just Another Word for Everything To Gain

“Freedom is just another word for nothin’ left to lose.” 

– Kris Kristofferson “Me and Bobby McGee”

I hope you had a wonderful end of 2025 and start to 2026.

Like most people, the end of the year can be a catalyst for self-reflection. I recently finished the book On Purpose: Practical Wisdom for Designing A Life of Purpose Inspired by the Life and Teachings of the Lubavitcher Rebbe. The essence of the book is that our goal in life isn’t to find ourselves or happiness but to find out the unique reason we were born. If we live our lives with clarity of purpose then everything else follows, including happiness.

As an example of the difference between the more Western approach of living a life of freedom directed by our own needs and wants versus the Rebbe’s of serving others being at the core of our purpose, I made a query of Readwise regarding freedom. As a reminder, Readwise is an app that takes all of one’s Kindle highlights and organizes them, and allows one to use its ChatGPT feature to ask anything of it, and it will respond with its thoughts based on relevant highlights that it will cite to help answer one’s questions. 

We are often told that our ultimate goal should be to get to a point in life where we have tremendous personal freedom so that we can direct our lives in whatever ways bring us the most satisfaction. I was curious as to how Readwise would define freedom for me based on all of my Kindle highlights it has tracked for me. This is what it produced:

Freedom, for you, is the growing capacity to author your life and become who you truly are, by taking radical responsibility for your experience, within the real limits of life—and, through that, gaining inner release from compulsions, fear, and unreality so you can love, create, and respond to each moment more fully. 

I really liked it as I’m a big believer in radical responsibility as well as being very cognizant of dealing with what is versus how I want things to be. At the same time, I also know how being enslaved by the bonds of compulsions, addictions, fears, delusions, and unhealthy thought patterns can completely derail our lives, no matter how good our intentions. Finally, by dealing with what is, taking full responsibility for my actions, and avoiding negative addictive tendencies, this can enable me to be a fully present and alive individual guided by love, beauty, and creativity. 

I saw the potential for this definition of freedom to help me to develop a lens through which to fertilize my thoughts and to take action. And yet, as I began to reflect on it, something was missing for me. It was missing the mark in some form or fashion. My gnawing feeling was that perhaps it was a bit too self-centered. I felt that there needed to be an even higher level perspective because my experience has been the more I think about me, the more I see where I may be falling short which then serves to trigger those negative thought patterns that radically diminish my freedom. How do I end up experiencing a life filled with love, creativity, and tremendous presence? Paradoxically, I knew that it couldn’t be focused on me.  So to whom could I turn to help me come up with an even more powerful definition of freedom?

Over the past few years I have become more immersed in the teachings of the Rebbe and I have felt more drawn into his view of the world and our place in it. He was the leader of the Chabad movement of Judaism. Its focus on how the human soul is constructed and how we can best live our lives so that the Godly part of our soul can rule over the animal part of it has always made so much sense to me. I have believed for many years that every human being is engaged in a great civil war between his self-centered ego and the higher calling of his or her soul rooted in the guidance of some form of a higher power. The Rebbe’s approach seemed the best one for us to win that civil war. 

Given this dichotomy between the Rebbe’s set of beliefs and way of living that was guided by his Godly soul and the Readwise definition that seemed to me to be more led by our animal souls, I turned to Copilot to compare and contrast what Readwise produced versus what the Rebbe would say.

This is how it responded.

That’s a fascinating question because it touches on two very different frameworks for understanding freedom: one rooted in existential self-authorship and another grounded in divine purpose.

The definition from Readwise emphasizes autonomy and radical responsibility—the idea that freedom is about authoring your own life within life’s constraints and liberating yourself from fear and compulsion. It’s very much aligned with modern humanistic and existential thought.

The Rebbe’s perspective, however, is deeply rooted in Chassidic philosophy and Torah principles, where freedom is not primarily about self-authorship but about alignment with a higher purpose. A few key contrasts:

1. Freedom as Service vs. Self-Authorship

• The Rebbe taught that true freedom comes from transcending the ego and connecting to G‑d’s will. In his view, the self is not the ultimate author; G‑d is. Our task is to discover and fulfill the divine mission embedded in our soul.
• So while your definition centers on “becoming who you truly are,” the Rebbe would likely ask: Who defines that “true self”? If it’s disconnected from its Source, then it’s not ultimate freedom—it’s still bound by the limitations of ego and circumstance.

2. Freedom as Liberation from Inner Pharaoh

• The Rebbe often used the Exodus narrative as a metaphor: freedom means leaving “Mitzrayim” (constraints) and serving G‑d. It’s not just breaking free from fear and compulsion for personal flourishing, but doing so to become a conduit for holiness and purpose.
• In other words, freedom is not merely “inner release” but inner redirection toward divine service.

3. Responsibility: Radical, but to Whom?

• Your definition speaks of “radical responsibility for your experience.” The Rebbe would agree with responsibility—but not as self-sovereignty. Instead, it’s your responsibility to actualize the mission entrusted to you by G‑d, which is discovered through Torah and Mitzvot, not self-authored meaning.

How might the Rebbe respond?
He might say something like:

“Freedom is not the power to write your own script, but the ability to fulfill the script written for your soul by its Creator. When you live in harmony with that purpose, you are truly free—free from the tyranny of ego, free from the illusions of self-definition, and free to bring light into the world.”

What I will say is that, contrary to Kris Kristofferson’s famous line (incomparably sung by Janis Joplin) which has the implication of throwing caution to the wind and going for it no matter the cost or consequences, that I have now come to believe that freedom is just another word for everything to gain. It’s living a life rooted in purpose and selflessness which has the potential to generate incalculable rewards for those with whom we share our gifts and ultimately ourselves.

In my book The Philosophical Investor: Transforming Wisdom into Wealth, I included my personal purpose statement at the time which was:

Creating wealth through discovery, effort, and teaching.

If you read the book or followed some of my writings in the past, you would know that my definition of wealth goes far beyond the financial realm. This purpose statement has served me well over the past 10 years in that I think it has guided me to make decisions and to take actions focused on creating more wealth for others and myself through my work, writings, charitable endeavors, and personal interactions.

With the new year upon us and the book now having been in publication for over 10 years, I decided to revisit this purpose statement and see if it still fits, or if there is an even better one for me.

Stay tuned as this will be the subject of next week’s blog.