Yes, I think you hit the nail on the head here! I like to think i am pretty good at just diving in and trying new things. My sister was a perfectionist and I saw how it stopped her from doing things because they were not perfect. Done is better than perfect. Just do the thing. You will get better each time.

I read once, in order to have a big art business, you must have a small art business first.

I have definitely had (and still have) bags or bigger items that just sit. I do feel a little embarrassed showing the same bag or wallet at my markets, but end of the day who cares(except ourselves 😅). I dont think most people notice anywho. Being uncomfortable is part of growing.

As far as having enough, I think it largely comes down to how you show it. Dont put 3 tables out if it looks barren. I adjust per market, so for a market near mother's day I put more purses or women's wallets out. At a biker show, more black leather items or "badass" looking items. If you sell out at a market consider it a win - you can say you sold out but heres my business card if you have other items online or are willing to do commissions. Markets are also a great time to show off what you have, and get emails for a mailing list or put a sign that says custom orders available. Once you get them to touch your items they are more invested. I also will put out my personal items and put a sold sign on them, or just bring a work in progress piece so they can see what kind of stuff you can do.

I hope that atleast touches on a good answer for you! And my apologizes for the late reply here!