If I have to, yes. I used to spend hours agonizing about how to approach an editor, or the owner of a micro-press, with questions, requests for updates, clarification of certain points in the guidelines. I didn’t want to “bother” them. They’re so busy. They have other writers, vendors, computer issues to deal with. I was raised not to put myself forward, so I’m usually uncomfortable speaking up. Finally, I got tired of the hamster wheel in my brain. Just ask. I tell myself, if you’re not sure, ask. If you’re still not sure, ask again. Did I turn some of those editors or publishers off? Without doubt. But I’ve decided it’s better to risk that than to either stew in uncertainty, or turn them off by not following their preferences. On the other hand, once things are clear, I follow rules. If a publication says wait three months for a response, I wait three months. If they want a certain format, I follow those instructions.
I also used to refrain from asking questions after talks or panels, thinking my ignorance of some basic thing that absolutely everybody already knew but me, would be met with scorn or exasperation. But then I decided, this may be my only chance. If people scoff, so what. I’ve also learned over the years, that if I’m confused about something, very likely someone else is as well. And if I speak up, they’ll be grateful that I did it and they didn’t have to. Or maybe the question hadn’t even occurred to them until I gave it voice. And guess what? My biggest fears have never come to pass. My concerns and questions have been treated only with respect and also with the precise missing piece of knowledge I needed.
Nobody’s born knowing this stuff. We all have different pieces of the puzzle, and luckily we can also count on each other, our fellow writers, for information. We share advice, tips and leads, on forums, in groups, and in private email exchanges. There’s a line between being pointlessly shy and being a pest. But this is my work. Like someone said, no one will ever care about my writing as much as I do. So, I risk a negative response if I’m a pest. But the whole business is about taking risks. At least let me take the risks that give me a chance of success.
Sometimes I wish I were an accountant. I’m actually good with numbers. So, I could have been, back when I was supposedly “choosing” a career. But nooooo, I had to do something with more romance, more cachet. Like being a writer. But man, I sometimes envy accountants, bookkeepers, actuaries and the like. After all, the numbers either add up, or they don’t. If they don’t, there are various tricks and techniques to help you figure out the glitch. Then, AHA, problem solved. Numbers are not subjective. There’s no judgement from them or from an unseen “editor.” You never have a bunch of fellow accountants sitting around a table, making suggestions on how they would add up the numbers if it was their balance sheet. There’s never a need to stare at figures and wonder, is there a more accurate, more descriptive number, the way I sometimes agonize over word choice. It’s either the correct number or not. And numbers, too, can tell a story. The dwindling totals in a bank account. The set number of days between exposure and symptoms. The timelines that don’t add up, revealing gaps in an alibi. And bankers can be detectives. See 
Lida Bushloper 