Sometimes I’ve found myself in the situation of having to do something that I knew I had to, but that I was dragging for too long because I was afraid of what could happen. Often, this meant asking someone something (a business proposition, a favor, etc). Other times, just telling someone something.
I’m the kind of person who wonders for weeks what will the other person say. “If they say yes it would be awesome! Life would be so easy. If they say no, then that would suck and I’ll need to find a plan B.”.
I don’t immediately do it because a) it’s usually an uncomfortable situation to be in, like asking someone for a favor, or maybe quitting a job and b) because, in case I’m asking something, that would mean facing the situation of having them say ‘No’.
But I’ve come to realize waiting to do those things doesn’t make any sense, for a few reasons. First, all that time I wonder what can happen, it’s just a waste of time and energy. I’m never gonna *know* what they’ll say until I ask, so trying to fantasize about each answer they can give is pointless. Of course you should plan the interaction, but don’t overthink it. A lot of times I’ve tried thinking about all the possible angles a conversation could go to, and then when I actually have it it’s completely different and unexpected.
Another important point is the realization that that interaction you’re dreading and postponing HAS to happen, and ask yourself: would you rather have a YES or a NO to something important to you NOW, or would you rather wait for a month, getting all concerned about what will happen if… If you’re gonna get a NO, you might need to think about a plan B, and if you’re gonna get a YES, you’re most probably going to have to do something with that answer (like move forward on a business transaction). Whatever it is, it’s always better to know sooner rather than later.
So leave the fear of asking aside and just do it now.