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You care, you want to be supportive, but you also feel protective of the person, the entity perhaps you are a member of and those you interact with within the entity. You want to be supportive, but you may also have a protective side, especially if you are an empath and intuitive etc… by nature who sees with the spirit guided by what the Spirit gives you.
When one of persons there is spinning their wheels to perhaps exhaustion trying to make an idea work that you know is not meant to be, sense they might be stuck in the past even with their personal life, and you sense this very clearly or even see any of this unfold right before your eyes, it’s tricky. If you simply tear down their dream, then you risk their resenting you for being a downer and all that. If on the other hand you play pollyanna and all is well, just smile and pretend all is bright and beautiful, you are not being much of a true friend. You are on a scale trying to keep the scale from tipping either where you are too harsh and totally make them feel crushed and like you have no faith in them, which you might, just not in a particular idea or project, or where you present a pollyanna unrealistic this is going to be great, all working out peachy, keep spinning your wheels, no biggie. Neither will serve anyone well. What do you do? For one if you are dealing with a professional situation, do your homework, so if you are going to give advice, you are giving it based on solid research and feedback maybe even that others have given on what has been going on. When you present any advice, even to a friend make it clear you support their dreams, their efforts to achieve a goal, but you are concerned about the spinning of their wheels, how that energy could be focused elsewhere. Anything regarding a personal nature, not moving on, returning to the past, maybe find a song that talks about leaving the past in the past and why it should stay there if they are artistically inclined. Letting them know you understand nostalgia can be powerful, but there is a reason people are not part of our lives, why we are apart, not truly connected anymore to others, best to move forward, not back, especially if that connection etc.. was toxic in any way.
We might know in our heart, spirit and soul that what the Holy Spirit has given us is what ought to be, a vision after God’s own heart that should be implemented, but others may not see that same vision, and may be spinning their wheels, banging their heads against the wall doing stuff that is not workable and not part of God’s great commission or even remotely part of his plan for the group, the person, the organization, but if we are going to get that vision across we can’t do it with the scale out of balance in either direction. Meditate, research, meditate on Scripture, and mediate some more. You will know how to approach things, even if not everyone will appreciate your efforts to do things right, the heavens will. Hope this helps in your journey through life and relationships.