Indicators of changing comfort levels

I regularly see posts that tell about the "Almost got Caught" or "Just forgot to remove all the evidence" type of experience. It's not uncommon to shortly after see the person who made the post has gone out for the first time, come out to someone or has moved from just doing midnight walks to shopping at the mall.

What I'm wondering about are the indicators of us approaching thresholds that define different levels of comfort and subsequent behavior. When we write that we didn't take the time to a good job of makeup removal and someone may have noticed or we didn't fully clean up after trying on new clothes, knowing someone was coming to visit, it seems pretty obvious in hindsight that something has changed in our thinking. We have become so comfortable and confident in our own minds with what we are doing that we are now open to new experiences.

I'd like to see what kinds of indicators for moving to the next step you've seen in your life. Are they subtle or earthshattering? Do some indicate moving back rather than forward?

I don't know how to rank the threshold indicators in terms of importance...but here are the ones that came to my mind:

1) going out the front door in broad daylight. In my case, I wanted to move the sprinkler, but didn't want to change back into my drabs for that minor task. When I realized I could venture out without bringing life to an end, I clearly had crossed both a literal and figurative threshold.
2) Getting a wig. I had moderate length hair, And although I had a professional cut and style, I just satisfied with my appearance. I bought a good quality wig, that I felt was flattering. I finally felt that I looked presentable enough to go out to public places.
3) Buying clothing and accessories that are age and situation appropriate. I use my wife as a model...if she'd wear a certain outfit in a particular setting, then I try to find things that are comparable. Oh, there are a few times, I'm a bit over-dressed for the grocery, but generally speaking I try to blend in. Having a wardrobe that fits the places I go has made it easier for me to venture out.

I kind of agree with Kim that the first time out the door dressed in any light is a major step. You've left the safety of your house and that is a biggy. Going out in daylight is even bigger in that you're more likely to be recognized.
Also when you start to shop and decide on your "style" and pick and choose what you like and also what looks good on you (not always the same).
Thirdly and the most exillarating feeling is when you can go out, and be comfortable with who you are and be able to interact with whoever you meet up with in any type of situation.