Embrace the cringe of the character(s) we are trying to be. - Remember, ultimately, we are all here to roleplay at the end of the day.
I think it’s natural to have some self-doubt. I, at least, despite my years of roleplaying across various mediums and even DMing tabletop games these days, haven’t lost mine.
And it can be a vicious spiral; the more you overthink it, the farther you can descend the spiral. - So, how to combat it? For me, it’s repetition and routine.
Repetition is pretty self-explanatory, but I find there is no better way to build confidence, regardless of what you are doing, whether it’s creative riding or riding a bicycle. - It is by far the simplest, but it takes time. It can be done by simply having a goal of approaching at least one person in character to say, “Hello, Nice weather today, huh?”
Routine - Establishing a routine can help both In and Out of Character, and wouldn’t you know it goes hand in hand with repetition.
IC routines can be as varied, in-depth, and complex as you want them to be or just simple goals. For me, having established routines for my characters allows me to have small, achievable goals, reasons to approach people and a general purpose. - I establish these routines for my characters as a way to remain purposeful, however vague, because personally, I’ve found that being idle allows for self-doubt to fester.
OOC Routines can be just as good to help with creative writing. - To give an example in regards to roleplay, depending on the theme, or area and what mood I want to convey, I listen to what I think is appropriate music, and it can help immensely with immersion.
That’s how I, in general, deal with self-doubt. But as far as your more specific examples…
This one is fairly relatable, especially as someone whose English is not my first language; it can be really easy to find yourself flailing. - In fact, when I first came to AD, I barely spoke, let alone wrote it, and I think one of my biggest worries, too, was my ‘style’.
I think the way I dealt with and still deal with it is to hang back, observe how others do it and imitate their style and establish my own through it by altering or adding my own ‘twist’. - So my advice would be, imitate those around you, find your own style and in turn, confidence through this.
I think this one is likely the trickiest of all your examples, and by far the one that allows the most room for doubt if just because it’s something we cannot always control.
Instead of focusing on the What If of other people’s opinions, I think it’s better to stick true to your character’s identity and person, their flaws and goals. - Always allow for constructive criticism, but also fight for your vision of your OC and realise when constructive criticism is just criticism for the sake of it.
This one can be a bit harder to gauge on your own. - And if you are uncertain whether your character fits the theme of the event or the Campaign, ask. Ask your fellow Roleplayers, ask the Campaign organiser or the relevant DM. And like above, fight for your vision of your character fitting the theme, lay out your reasoning, but also be respectful of others. - The worst we can do is assume the answer ahead of time because you might find people agreeing with you.