One big consequence of our fear of embarrassment is that we're almost all overly sensitive to rejection. We haven't built up our acceptance-of-rejection muscles, and this is a major impediment to agency. I've found that the most efficient way to build these muscles is to make audacious requests.
Most of us carefully assess which requests are acceptable and which go too far. We avoid any request that's likely to generate social friction, behaving as if a denied request would be a disaster. We also really don't like being told "no," which feels like a judgment that we've overestimated our worth. Hence, we opt out of asking.
Yet trying to prevent ourselves from ever experiencing rejection costs us. If you are determined to avoid rejection wholesale, you will likely never ask a stranger in an unfamiliar field for help getting a job, ask someone you admire for feedback on your work, or publish anything creative online.
A more helpful point of view is that rejection is a form of information. When you experience rejection, you've learned that a given request won't work. That avenue is now shut off, freeing you to try something else.
A high-agency mindset goes further: seek out rejection, or at least welcome it. Remind yourself that if you don't routinely encounter rejection, you are not asking for enough — you're only making requests that are very likely to receive a yes. The more times you hear the word no and notice that it isn't the end of the world, the less aversion you'll feel.
The Art and Science of Asking Big
One: If you habitually avoid rejection, you are not going to be well calibrated about what's reasonable — which might be more than you expect. When I started training myself to make bolder asks, I found it helpful to think of myself as wearing rejection-sensitivity goggles: lenses that make every ask look more unreasonable than it really is, and every no feel more severe than it really is. The goggles also make us overestimate how often we will be rejected.
In a series of experiments, researchers Frank Flynn and Vanessa Lake got students to ask strangers for help. They asked the students to predict how likely people would be to help, and found that they underestimated by 50% — about twice as many people as expected agreed. The students displayed an "egocentric bias," focusing too much on their own feelings: because asking felt awkward to them, they assumed it must feel awkward for the people receiving the requests.
But of course, it often feels pleasant to be asked for a favor that you can capably grant. We just forget this, acting like we're visiting a curse on an innocent person rather than giving them a chance to show their capability and generosity.
Two: When you train yourself to be less afraid of rejection, you will find your requests are granted more often, because you'll make them with greater confidence. If you're scared to ask someone for a favor, they will feel your fear and take it as a cue: They're scared to ask this, so it must be a really big deal. I should say no! If you don't signal fear, they'll be more likely to consider the request reasonable.
Three: Unreasonable requests can open the door to reasonable requests. In a classic study by Robert Cialdini, researchers first made strangers a request so big that almost everyone refused it, then followed with a much smaller one. Those strangers agreed to the small request about three times as often as people who were asked for it directly. It works because of the social norm of reciprocity: if someone makes a tacit concession, we should reciprocate with one of our own.
Don't Hedge or Hector
Audacious asks can't be made hesitantly or halfway. Ask for what you want, straightforwardly. If you sense a no isn't necessarily the end of the conversation, you can ask: "Okay, I'm not trying to convince you to change your mind — but could you tell me why it's a no for you?"
This was a lesson Jia Jiang learned in his one hundred days of rejection: Don't run, ask why. There is an enormous difference between our stories about why people turn us down and why they actually do.
Agency is all about breaking through the fictitious barriers of your life and letting yourself be limited only by real barriers. A firm no is an actual barrier. Show respect for that, and tell yourself that you are now that much more aware of another limit, and free to pursue another ask.