Compassion is a word that gets used a lot, so much that most of us actually don't know what it means. Many people site the Latin etymology compati, which means 'to suffer with,' but what does that look like in practice? Obviously if we are in a situation where someone else is being harmed and we are able to intervene or help, then we should. But in many cases we are faced with another's suffering that we can't do anything about. In those situations we often have instincts to try and comfort or provide an answer of some sort. Unless the person we are with has directly asked for input, our advice and good intentions can often create more suffering when they feel like they have to pretend to be better, or take care of our anxiety at their distress.
Having willingness to be uncomfortable together means that we check our own good intentions. It means that we listen to the reactivity that arises in ourselves around another's pain. It means that we do the work of not taking their experience personally, while also being accountable as a witness and listener with them. It can also sometimes mean that we stop enabling another person. If we have relationships where we are always the one who somehow needs to fix, comfort or modify around someone else's trigger or addiction, when we choose to stop our enabling we have to be willing to be uncomfortable for a while and let the relationship find a new balance point.
This relationship experiment can happen anywhere, anytime, and it's often most effective with people who are close friends, family, or partners. You can do the experiment when you notice that you are responding or acting habitually. You know what this feels like, it's when you shut down, go on auto-pilot and actually stop feeling the other person. The willingness to be uncomfortable is the choice to be present the actual moment of interaction and to respond honestly: don't fix anything you can't fix or don't want to fix. Don't enable. Don't placate or pacify. Try to give yourself lots of space for the uncomfortable moment and remember to breathe! Notice what shifts.