For me the thing that helped the most to cultivate a healthy relationship with passing was to focus more on looking attractive rather than focusing on looking like a cis woman specifically.
The reason it helps me is because:
-
attractiveness is more decoupled from transitioning
That's not to say that it's completely decoupled (I do want to be pretty!!!!) but thinking in terms of attractiveness helps me better separate what I'm doing for myself rather than what I'm doing to satisfy the cis gaze. Moreover, I don't have to wait until I'm done medically transitioning to look attractive; I can do stuff to make myself more attractive at any time and regardless of my gender presentation.
-
attractiveness is a "nice to have"
Thinking in terms of attractiveness reminds me that it's not the end of the world if I'm not attractive (lots of people are unattractive!) so I don't kick myself if I don't look attractive.
-
I don't have to look attractive 24/7
Even when I do want to look attractive I don't have to be attractive all the time. Some days I can just let myself go and that's okay and other days I feel in the mood to be hot as hell. I can just follow my mood instead of trying to be perfect all day every day.
-
I have more control over what attractiveness means to me
Framing things in terms of attractiveness reminds me that I can choose what it means for me to be attractive to others by choosing my style instead of trying to impersonate some stereotype in my mind of what I think a cis woman is supposed to like.
-
I don't have to look attractive to everyone
The flip side of the last point is that I can also choose what it means for others to be attracted to me! I can't be attractive to everyone (that's just silly) but instead I can focus on what kind of people I want to attract and cultivate my appearance accordingly. Choosing who I want to attract also gives me more control and input into my appearance instead of trying to please all cis people.