If only the world were so simple. They say that closed mouths don’t get fed, which is true. Some people are rewarded handsomely for displaying audacity. They get life-changing opportunities against the odds because they had the guts to ask for it. However, I think we need an opposing proverb to describe what I’m feeling. If you open your mouth at the wrong time, you might swallow a fly.

I would love to think of asking for something as a neutral action. If the person doesn’t want to give it to you, they say no. No harm, no foul. I thrive in contexts where this is the rule. But in most social contexts, this isn’t how it works. Asking someone for something can offend them, because they will think about why you’re asking, and sometimes they will come up with an answer that damages your relationship. Asking someone for something can freak them out, because they will think about what happens if they deny your request, and sometimes they will come up with an answer that makes them feel coerced. I’m guilty of doing this too, even though I try not to jump to conclusions without gathering conclusive evidence.

It makes a lot of things in interpersonal relationships fraught. Asking for something without a reason to believe I’ll receive it uncoerced is a huge risk. I can’t just ask people for time, I have to sell them on what they’ll get in return. I can’t just ask people about their private lives, I have to demonstrate that I’m not a threat. I can’t just ask people for attention, I have to prove that I deserve it. I can’t just ask people for sex, I have to have a reason to think that they want it too. I can’t just ask people for opportunity, I have to know that they’ll believe it should go to me. I can’t just ask people for a certain price, I have to estimate how low/high I can go without bruising their pride. When I skip these steps, I ruffle feathers and make enemies most of the time, and occasionally I win big just by being the first person to ask.

It’s exhausting, the gap between wanting something and being allowed to ask for it. Minimizing the risk of blowback requires gathering so much information, but I can’t just ask for the information I need. I can obtain it through back-channels and patient observation, or I can just take a leap of faith. It’s gotta be the least fun form of gambling. I feel deeply alienated from people who don’t understand why it’s hard for me to deal with this.

Sometimes, I find myself in a position where I want something, but I don’t have the means of creating the context to ask for it. Maybe I don’t know how, or I don’t have the time or the resources or the relationships or the patience to do it. Historically, I’d resolve this by asking anyway. They say that fortune favors the bold, after all. They should also say that misfortune favors the bold too, because this strategy has often backfired. It seems like the context is genuinely required. You don’t just get rejected from programs and turned down by women, you become the subject of blacklists and gossip for daring to ask. You can learn to tolerate rejection as much as you want, but other consequences will catch up to you if you keep asking for things you’re not supposed to.

Every time you see someone appear to beat the odds — they landed a lucrative job or a bombshell partner, or pulled off an impossible event, or extracted some secret information, or made a massive sale, anything that requires asking in order to work — and it looks like there is no context for this achievement, it doesn’t mean that context wasn’t necessary. It means that the context wasn’t public.

The work of setting up a context where it’s acceptable to ask is something that I yearn to be able to skip. My closest relationships (the ones where I feel like I can be myself) are the ones where I feel like there’s nothing I might want to ask for that would backfire, the ones where the relationship itself is the context that makes most things acceptable.

Outside of such relationships where your guard is down and you can assume good faith, the context is required. Accepting this reality has been hard for me. I haven’t figured out yet how to make this jive with the rhetoric that encourages audacity. I haven’t figured out yet how to strive for greatness without being limited by my lack of context. I want it all, but asking can sometimes hurt more than it helps, so it feels like I have to do it all alone.