Bitachon and People-Pleasing
We’ve established that bitachon and the quality of our choices reinforce each other, yet those most committed to responsibility may suffer more fear and anxiety than others.
While spiritual sensitivity should ideally bring peace, unresolved wounds from the past can distort that sensitivity into chronic self-doubt. Childhood experiences and toxic shame can create an overactive conscience, leading to excessive guilt, remorse, and a disproportionate sense of responsibility. This often manifests as a need for perfection, self-unforgiveness, and taking responsibility for uncontrollable events. It’s important to recognize that these circumstances are intertwined with one’s mazal and are essential for fulfilling our tikkun-tafkid.
Yet understanding the source doesn’t eliminate the struggle—it only clarifies what must be overcome. These extraordinary individuals—firm in their emunah—do not struggle from a lack of conviction but from a deeper fear of disconnection.
The result is a compounded struggle: First, they live with a persistent hum of anxiety, acutely aware that they find it difficult to assert themselves when necessary. They become people-pleasers—perpetually on edge, emotionally drained, and unsure how to stand their ground. Second, when they inevitably give in to appease others, their self-esteem suffers—driving the ego to rationalize the behavior: either (a) it was the right thing to do or (b) who am I to stand up and say no? This cycle of fear, concession, and justification not only strains relationships but also deepens the rift between them and their authentic selves.
Fear in Disguise
On the surface, it’s easy to confuse someone who gives to be liked with someone who gives because it’s right. Yet these two modes leave different emotional imprints. Intention is everything—it’s the difference between giving a donation and being robbed. In both cases, money moves from one person to another, but one experience is empowering while the other is debilitating. Giving out of fear or guilt drains self-esteem, because we are not truly giving at all—the other person is taking, with our consent. Unable to tolerate the thought of disapproval, we choose the path of least resistance.
Earlier, we established that the more our identity feels threatened, the more the ego steps in to shield it—often by avoiding anything that challenges our self-image. We want to believe “I’m a good person,” and, thanks to the ego, being good often becomes equated with doing what others want, so we contort ourselves to protect that fragile self-image. But this is a fool’s errand. If we define our goodness by being liked by everyone, we will not only become anxious through our dependence on others, but also feel like failures when we inevitably fall short, as we all do.
This struggle isn’t limited to people-pleasers. Those who project arrogance and self-assurance often battle the same cycle—driven not by appeasement but by domination. Arrogance may look like confidence, defiance, or self-righteousness, yet it masks the ego’s fragility and a desperate need for recognition. Someone amassing great wealth, for example, may seem indifferent to others’ opinions, yet the pursuit can be rooted in a craving for validation. They remain perpetually restless and unfulfilled—just as dependent on others as the pleaser, only in a different disguise. As we explored in the previous chapter, such individuals often experience intense fear and anxiety, though they are typically more skilled at hiding it.
Shield and Shell
Rabbi Simcha Zissel Ziv writes, “If you observe people carefully, you will see that someone who loves the approval of others will, as it were, sell himself as a slave to those who flatter him. He will not even realize what is happening” (Chochma U’Mussar, Vol. 1, p. 219).
We often wear masks and play games—curating an image to avoid self-reflection and to project a version of ourselves we believe the world expects. This ensures we receive the right feedback while keeping others from seeing the real us. Our actions are no longer pure; they are manufactured in a factory of fear.
As the authentic “I” fades, so do energy and vitality. This self-encasement—living through the ego’s lens—chokes passion and will. It breeds guilt, despair, and even depression as we realize we’re not living the life we were meant to live. When the ego shapes our goals, we tell ourselves we’re playing it safe, when in reality, we’re hiding—from challenge, from rejection, and most of all, from ourselves.
This dynamic becomes especially destructive when we consider what Chazal teach about honor and shame. Chazal teach that publicly shaming someone is worse than killing them (Bava Metzia 58b), because humiliation can be devastating—especially for a person with fragile self-esteem. It can drive them into hiding, and in effect, destroy their life. By contrast, Chazal instruct us to show honor to others (Pirkei Avos 4:1), yet when it comes to our own honor, we are told to run from it, since the pursuit of honor stems not from the soul but from the ego.
The path to freedom lies not in avoiding all honor or seeking universal approval, but in grounding our sense of worth in something unshakeable. Chovos HaLevavos explains that bitachon frees us from this trap: “One who trusts in Hashem will not submit to anyone, set his hopes on any person, or place his trust in human beings” (Shaar HaBitachon 4). Recognizing that no one can harm or benefit us without Hashem’s permission, we release fear-based dependence on others and place our trust solely in Him. As Shlomo HaMelech declares, “The end of the matter, when all is said and done: fear G-d and keep His commandments, for this is the whole duty of man” (Koheles 12:13). This is the only fear that matters—the fear of wasting the Divine potential within us. Ultimately, the greatest pain isn’t from what we failed to achieve—it’s the shame of what we never dared to become.
Exciting News!
For the past 11 months, we’ve serialized my book How Bitachon Works (Feldheim Publishers), and the feedback from readers has been both humbling and energizing. Now, I’m thrilled to continue the journey with a new six-part series addressing the real-world struggles so many face today—stress, anxiety, panic, fear, overthinking, and emotional overload.
Using cutting-edge insights from neuroscience and psychology, all viewed through a Torah lens, we’ll turn these challenges into practical, usable strategies that you can instantly apply in your life. See you next week.
To be continued.