If you get up the guts to take the risk of just asking, might as well go one step further and ask boldly. Think about it: if you ask someone if you can borrow money, let’s say for a business loan, and the answer is yes, are you really going to sit there and ask for a measly couple thousand dollars?
If you’re going to ask, as for as much as you possibly can. Ask for the moon. Remember the worst thing that can happen? The person says no? And then what have you lost? (Nothing.) And so what if the answer is no? You negotiate down from your original request. But if you ask for a loan of say $10k, and the yes comes all-too-quickly, you know right away that you asked for too little.
Sometimes risk-taking means you make a bold decision in answer to your own question.
Example: I have been contemplating not teaching in the fall, mostly because it’s a lot of work for not a lot of money. But I’ve been thinking about it more and more lately. Every time I sit at my desk to “work,” I’m spending most of my time prepping for class, reading for class, responding to essays for class, and very little of my time on projects that I actually want to be working on — like building a bigger audience for these monologues.
So I inquired about fall classes, and had told myself that unless two specific classes were offered, I wouldn’t accept any. The answer came back. Two classes were offered. But neither was one that I had agreed with myself to take. I emailed back saying, “I’m more suited for these other two courses, are either of those available?” The answer came back again. “No. But I have this instead.”
I boldly took the risk of saying, “I think I’ll pass this time.”