Cav,
I don't think the answer is always clear but I find it helps to look at people whom I admire and to consider what matters most for me and what I would like the world to become and go from there. Generally for me that means thinking in a bigger picture beyond myself or my local community. But also trying to take into account any groups that become minoritized (I don't think that's a word...) by my decisions. I think a lot of that only relates to issues with an ethical tinge though.
I can give a recent example from my own life. It's a practice, not a belief, but the issues connected to it had to do with understanding my ideals and values while honoring those things I hold sacred. I just ordered three pairs of neatzit tzitzit katan. It's the type of tzitzit worn attached to an undergarment. Neatzit makes it in sort of a T-shirt. I've wanted to have them for a few years now and with a thread of one of the modern researched suggestions for techelet, which is the blue dye made today of either the common cuttlefish or murex trunculus. Now that I'm vegan that doesn't really work for me, to bring back a practice that vanished which only harms more life. I'm not so bothered by existing ritual items made from animals (though I'd be interested in a papyrus (used to be used for Jewish sacred texts) Torah and would rather own a used shofar and tefillin than new ones.) I placed the concept of tsaar baalei chaim first which is the understanding of the paind and suffering of living creatures. And yet I'm still driven to have a thread of blue in my tzitzit and I wanted to honor that.
I found that indigo has been compared to the color of techelet. May have even been used to make fake techelet but people looking to make more money. Karaim use indigo for techelet. And according to some research it's a possible candidate for the original techelet. Halachically it's forbidden to use it. But the blue thread is more important for me than that. And it's unlikely many people will know the difference to see it besides me. For me though, it becomes a thread of compassion that I notice every time I look down or have my hands around my sides (which for someone who has difficulty with eye contact is fairly often

) without losing its more traditional reference to the Divine imperative for arbitrary, ethical and mythical actions that help one become aware of G!d's presence. And a reminder then of not just compassion for non-humans but for humans too.
To give an example where I'm more conservative, there's a lot of G!d language in Judaism that says King or Lord. I can't really relate to those things on a literal level. When I'm with a group of other people, depending on the community, I generally just say Lord and King, Adonai and Melech. If I'm in a community that says Yah instead of Adonai I'll do that but I'm not going to violate the comfort level of a given community. It's just not important enough. When I'm on my own my practice is a bit more varied. I still use those terms sometimes when that's the interface I relate best to. Sometimes I need Avinu Shebashamayim, our Father who art in heaven. Sometimes that's the way I relate to the Divine. And it's also my default language because it's what I was brought up with. But at other times I'll embrace other relationships and in general when I'm really in a need to connect with G!d I'll usually speak in terms of the Divine feminine. But that's in private practice. I think the only time I use feminine G!d language in shul is when there are references to the shechinah (G!d's indwelling presence, the Divine feminine) in the siddur (like the lecha dodi prayer) or for avinu malkeinu (Our Father Our King) where I'll say Imenu Malkateinu (Our Mother Our Queen) and I'll only do that there because it's the practice for that community and thus tolerated. Sometimes I'll test the boundaries of certain communities, but only if I'm invested in them and it's just a little stretch, a little at a time. There's a wonderful teaching from a school I went to, "No confrontation without investment" that I try, not always successfully, to keep in my mind.
I also try when making a decision that goes against the norm, not to leave G!d out of it, to make G!d a part of the decision-making process either by meditating on it, talking to G!d and always consulting earlier answers to the question to see what I can learn and what makes sense for me. The other thing that for me is very true is that it's okay to experience something non-rational that on an intellectual level I may have objections to. On an intellectual level I take issue with, for example, some of the stuff that happens with the Exodus from Egypt, and I don't beleive in its historicity. But I feel it as a living history, as a meaningful story my people have told about themselves that contains many truths. When I'm not on the experiential level I can let my intellect come up with lots of criticisms and judgements. At Pesach (for example) I don't entertain that stuff so much because it's time to submerge in the experience and try and lift my feet from the ground so it reaches every inch of my body (inadvertent mikveh reference.) In that way I can keep both of those aspects of myself happy and my intellect is okay knowing that the experiential is just one perspective. I get into a lot of arguments with theists sometimes when they ask me questions about belief in G!d (not so much arguing here.) But if instead they asked about experience of G!d or trust in G!d, if G!d's a part of my life they'd get a very different answer. I like a little dissonance. Keeps me from getting too set in an overly rational or overly non-rational approach.
Dauer