Much of the trajectory of a typical human life is guided by fear, often a fear of rejection. And the form this guidance takes is of limiting one’s opportunities and accomplishments. This fear of rejection is a relic of our ancestral heritage. Extreme caution was appropriate in a small hunter-gatherer community in which a single rejection could result in permanent social ostracism, and our genes were shaped by that environment. But in modern society, communities are fragmented and typically non-overlapping, and many of the people you meet today you’ll never see again. You shouldn’t care what strangers and casual acquaintances think about you, but you probably do.
People tend to prefer suffering later rather than suffering now, and so they opt for the timid route of inaction, accepting future regret to avoid current rejection. But regret hurts more than rejection. In the nursing home you will regret not the things you tried and failed at but the things you didn’t try at all. The only thing you lose in a rejection is external validation, which you should not be seeking anyway.
Successful people get rejected more than unsuccessful people, because they ask for more. True failure isn’t being rejected, it’s giving up or not trying. The more you get rejected, the less it will bother you. Once you can treat rejections as a necessary step on the most direct route toward success, you can ask for anything at any time, without limit.
So get out there, be bold, make a few mistakes, make some slightly outrageous requests, and don’t worry about what people think. In business, in dating, in relationships, in life, the more you ask for, the more you get. Act like you don’t expect to be rejected but that even if you are that you don’t care. As long as you don’t break the law, your “failures” won’t go on your permanent record, and you’ll succeed a lot more.