Strength of Struggle Q&A #14: When Assertiveness Feels Harder Than It Should

Q:

Dear Rabbi,

My friend and I feel better after being assertive. We’re not doing it enough, but when we do, it helps. The challenge is that I still get intimidated sometimes or slip back into not speaking up when I could. I’d really appreciate some ideas.

Shira

A:

Dear Shira,

Thank you for sharing this question. Knowing when, and how, to assert oneself can be very challenging.

First, the fact that you already feel better when you are assertive matters. That shows this is real growth. Slipping back does not mean you’re failing. It usually means the situation itself is harder, not that you lost the ability.

The Rambam writes that changing inner traits happens gradually , step by step, and not all at once (Hilchos De’os 1:7). A person may act one way in calm settings and still struggle when pressure or fear is involved. That does not cancel the progress. It shows where the work is still developing.

It also makes sense that this comes up more with strangers, customer service, or people who sound scripted, dismissive, or blaming. When someone holds power or speaks sharply, many people instinctively pull back. That reaction is human. But the mitzvah of kavod habriyos (respecting people) applies to yourself as well. Quiet that comes from fear is not humility.

One practical thing that helps is to stop trying to explain or justify yourself. Choose one simple sentence that states what you need, and repeat it calmly. For example:

“I understand. I’m still waiting for results from a call made 2.5 weeks ago.”

If they push back, you don’t argue. You simply repeat it, respectfully and steadily.

Another piece is internal. Before these interactions, remind yourself: “I’m allowed to speak respectfully and take up space here.” That is part of self-respect, not selfishness.

Assertiveness doesn’t mean never feeling intimidated. It means noticing it and still staying with yourself. The fact that you’re already doing this sometimes tells me you’re strengthening something that used to collapse automatically.

Hashem should give you the strength to be az kanamer, bold like a leopard (Pirkei Avos 5:20), to have azus d’kedusha , holy firmness, to do what’s right, especially when facing pushback.