Are You Self-Aware Enough to Know if You Are Helping or Simply Enabling Someone?

Diana Rose
Know Thyself, Heal Thyself
3 min readJul 13, 2021

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Image by Sirisvisual on Unsplash

There’s a fine line between helping and enabling.

Both spring from our desire to help someone but one does more harm than good for the person we are trying to help.

I’ll take my own experience as an example.

A few months before my ex and I broke up, I remember him telling me that he was enabling my negative behavior — in one of our fights.

And while I know the word and the concept it carries, I barely understood what he really meant.

We often fight because of my insecurity and whenever he would call out my behavior, I would always convince him that my insecurities were well-founded and that I was just only asking for his reassurance.

In his desire to help get rid of my insecurity and give our relationship a chance, that fighting-reassuring dynamic in our relationship went on until we eventually broke up in our last and most ugly fight.

Only in our breakup did I fully understand what he meant when he said he was enabling me.

At the core of our humanity is the desire to help others, especially those we care about. And while helping others is a good intent— it becomes counterproductive when we don’t add self-awareness into the equation.

“Self-awareness is the ability to see yourself clearly and objectively through reflection and introspection. “ (Courtney E. Ackerman, MA)

In harnessing the power of self-awareness, you may ask these questions:

  1. Why do I want to help this person?
  2. How long should I help this person and when do I stop?

From there, you can start identifying your own expectation or motive and can also check whether your reason for helping is really for the benefit of the people you are trying to help — or if it benefits them at all.

True self-awareness allows us to know the extent of what makes us who we are — our thoughts, motivation, feelings, aspirations and goals — and use them to our advantage.

In the context of helping loved ones or people in general, self-awareness lets the helper see the demarcation line to discern when helping does its job and when it is enabling.

Let me take again my failed relationship as an example:

My ex did not lose his self in our relationship. He was able to tap into his self-awareness and have the courage to end the toxicity I had slowly injected into his life. He knew the relationship was not serving him nor was he able to help me overcome my insecurity.

In retrospect, he was right all along when he said he was enabling my negative behavior. It may sound counterintuitive, but he was only able to truly help me when he left.

As I said in the beginning of this article:

There’s a fine line between helping and enabling.

That fine line lies in our self-awareness.

And so, the next time we are caught in a situation where we have to decide whether or not to help someone, let’s not forget to be self-aware.

This is in response from Diana C.’s challenge that she laid out here.

(Question #2: How does being endlessly understanding get in the way of true closeness?)

Diana C., thank you so much for giving us an opportunity to reflect using your thoughtful and brilliant question-prompts. 😘

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