I can really empathize with this struggle. >As a listener, are you agreeing with this or are you neutral nodding your head? The "trick" I do is to try to set

I can really empathize with this struggle. >As a listener, are you agreeing with this or are you neutral nodding your head? The "trick" I do is to try to set aside whatever train of thoughts I might have had before the person spoke to me, and try to imagine that the thing they talk about is happening to me. And then, voice my reaction to that. So if someone told me that "I'm fearful for my job. I think I might be fired soon", the first that comes to mind is "Oh my god, that's horrible! Why do you think that happens? Have they hinted about this before?" Now, this maybe works a handful of times in the conversation. A second thing that you can do is trying to imagine the relations of the thing that just got told to you. By relations, I mean relating to anything, how it connects to anything: the speaker's environment, life circumstances, your shared universe, anything. Continuing the example above: "The timing is such a shame, given what's going on in your life, I would have liked it that at least the job is stable". Third thing, you could discuss the persons possible actions and reactions to the event, and how others in their life have, or will have taken it. Continuing: "Do you have anything else lined up, just in case?" "Could your side gig support you until you find another job?" "How did your spouse take the news?" And the fourth thing, it's always worth thinking about WHY the other person told you the thing they did. What are you to this other person? A friend? Colleague? Are you their superior? Spouse? Do you relate, in a way, to the thing that they told you? Are you maybe a recruiter, and that's why they tell you that they are fearful for their job? The answers to these questions can bring you closer to your natural response to the situation.