Authentic freedom is a complex concept that has been debated by philosophers and theologians for centuries. Authentic freedom includes the ability to make one's own choices, the absence of coercion or oppression, and the pursuit of one's own values and goals.
Our gemara on Amud Aleph discusses the psychological and halakhic concept of עַבְדָּא בְּהֶפְקֵירָא נִיחָא לֵיהּ for a slave. Becoming free is not necessarily considered an absolute benefit. The halakhic significance of this is that one cannot necessarily automatically acquire a bill of freedom on behalf of the servant because it may not be something that he wants. We cannot therefore presume his consent. The Gemara states that the reason why it is not a benefit for the slave is because though he will obtain freedom and autonomy, he will lose freedom to pursue a less moral lifestyle. First, as a slave he is not bound by certain mitzvos, and secondly, he also has access to other female slaves, who tended to be sexually promiscuous.
The Ishbitzer works with this idea of subjective freedom and slavery to describe two paradoxical trends in the human spirit (Tiferes Yosef, Pesachim 8). He goes as far as to say that the slavery in Egypt was more about the bondage of the soul and the inability to appreciate freedom as being free from desires. After all, the Jews declared that they had access to all the pleasures in Egypt?
זָכַ֙רְנוּ֙ אֶת־הַדָּגָ֔ה אֲשֶׁר־נֹאכַ֥ל בְּמִצְרַ֖יִם חִנָּ֑ם אֵ֣ת הַקִּשֻּׁאִ֗ים וְאֵת֙ הָֽאֲבַטִּחִ֔ים וְאֶת־הֶחָצִ֥יר וְאֶת־הַבְּצָלִ֖ים וְאֶת־הַשּׁוּמִֽים׃
We remember the fish that we used to eat free in Egypt, the cucumbers, the melons, the leeks, the onions, and the garlic. (Numbers.11.5)
The Ishbitzer maintains that the advanced refined soul can settle for nothing other than true emotional and spiritual freedom, while the lustful person is a slave to his or her desires, and happily chooses this form of slavery over actual freedom.
As our sages teach us in Pirke Avos (6:2)
וְהַלֻּחֹת מַעֲשֵׂה אֱלֹקְים הֵמָּה וְהַמִּכְתָּב מִכְתַּב אֱלֹקְים הוּא חָרוּת עַל הַלֻּחֹת, אַל תִּקְרָא חָרוּת אֶלָּא חֵרוּת, שֶׁאֵין לְךָ בֶן חוֹרִין אֶלָּא מִי שֶׁעוֹסֵק בְּתַלְמוּד תּוֹרָה.
And it says, “And the tablets were the work of God, and the writing was the writing of God, graven upon the tablets” (Exodus 32:16). Read not haruth [‘graven’] but heruth [‘freedom’]. For there is no free man but one that occupies himself with the study of the Torah.
Great people throughout history who had giant souls knew what real freedom was. Socrates has similar thoughts about freedom as he rebuked his accusers who sentenced him to death, and even his friends who try to arrange to break him free from prison, which he refuses to do. Socrates accepts his unjust punishment (Plato's apology of Socrates) more concerned about abiding by the law and his own personal values than his safety:
And I prophesy to you who are my murderers, that immediately after my death punishment far heavier than you have inflicted on me will surely await you. Me you have killed because you wanted to escape the accuser, and not to give an account of your lives. But that will not be as you suppose: far otherwise. For I say that there will be more accusers of you than there are now; accusers whom hitherto I have restrained: and as they are younger they will be more severe with you, and you will be more offended at them. For if you think that by killing men you can avoid the accuser censuring your lives, you are mistaken; that is not a way of escape which is either possible or honorable; the easiest and noblest way is not to be crushing others, but to be improving yourselves. This is the prophecy which I utter before my departure, to the judges who have condemned me.
And, we find similar sentiment in a modern day hero, Anatoly Sharansky (In his autobiographical account of his years in Soviet prison for the crime of merely requesting to live in Israel “Fear, No Evil”)
My arrest changed everything. When the prison gates closed behind me, the huge world that had opened before me in recent years as the arena of an all encompassing struggle between good and evil was suddenly narrowed down to the dimensions of a prison cell and my interrogator’s office. I had to take everything that was dear to me, everything that had meaning in my life, with me to prison. The world I recreated in my head turned out to be more powerful and more real than the Lefortovo Prison; my bond with Avital was stronger than my isolation, and my inner freedom more powerful than the external bondage…Yes we were bound to each other not merely by memories of the past, or by photographs or a few letters, but precisely by that elevated feeling of freedom from human evil and bondage to God’s covenant that lifted us above earthly reality.
Upon finally being set free after a decade, Sharansky reflects:
In one respect prison was easier: In the punishment cell I was inwardly a free man, and I knew I was doing everything I could. Here things are far more complicated: There are thousands of opportunities to act, and who’s to say what constitutes enough? In a sense I am no longer free, for I can become free only together with those I left behind.
In freedom, I am lost in a myriad of choices. When I walk on the street, dozens of cheeses, fruits, and juices stare at me from store windows. There are vegetables here I’d never seen or heard of, and an endless series of decisions that must be made: What to drink in the morning, coffee or tea? What newspaper to read? What to do in the evening? Where to go for the Sabbath? Which friends to visit? In the punishment cell, life was much simpler. Every day brought only once choice: good or evil, white or black, saying yes or no to the KGB. Moreover, I had all the time I needed to think about these choices, to concentrate on the most fundamental problems of existence, to test myself in fear, in hope, in belief, in love. And now, lost in thousands of mundane choices, I suddenly realize that there’s no time to reflect on the bigger questions. How to enjoy the vivid colors of freedom without losing the existential depth I felt in prison? How to absorb the many sounds of freedom without allowing them to jam the stirring call of the shofar that I heard so clearly in the punishment cell? And, most important, how, in all these thousands of meetings, handshakes, interviews, and speeches, to retain that unique feeling of the interconnection of human souls which I discovered in the Gulag? These are the questions I must answer in my new life, which is only beginning.
How can we actualize authentic freedom in our lives?
Freedom requires the ability to pursue one's own values and goals. In the modern world, the abundance of choices and the constant bombardment of information can make it difficult to focus on what is truly important. We must first understand the nature of freedom and then make choices that are consistent with our values.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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