Chasing rejection

Short note: I wrote about chasing rejection after rejection with unchanged optimism. Please reply to my email or comment here with your thoughts. I also write a newsletter with commentary on how businesses make money. Newsletter link here.

Rejection is awful. You could expect it and it would still sting. It feels unfair, unwarranted and a glaring mistake. You were the only victim of a bloodless crime and you live to see the day. The person/ entity that rejected your proposal did not give you a real opportunity. It was pre-planned, the answer was always no and the world conspired against you. We deflect rejection and how it feels with such perfectly reasonable thoughts.

All my life, I have pursued a ‘Yes’. An acceptance from the right girl, the right company and the right stakeholder. I painstakingly sought out acceptance at the cost of all else. I carefully planned my days to maximise approval and minimise rejections. This resulted in fewer moments of despair but also fewer moments of accomplishment attached with a ‘Yes’.

I didn’t see it then. Even now, I don’t fully value the fringe benefits of rejection. You’re supposed to pursue opportunities with a higher probability of success. You want to play games where the odds are in your favour. I now realise that if you play winning hands all the time, you’re potentially missing out on asymmetric upside. 

In other words, you should pursue opportunities with a low probability of success if the resultant upside is high enough. This can be more rewarding than only choosing opportunities where you are likely to succeed but the rewards are immaterial. Not everyone gets this maths right. I haven’t, not even close. 

However, I have now begrudgingly realised the value of asymmetric bets. If you get them right, and this takes a cocktail of luck, work ethic, self belief, right people and immaculate timing, it is life changing. If you get these wrong, let the anguish harden your resolve for the next bet. Do not succumb to despair. You have to get back to work and get better.

In a hypothetical situation, you should pick yourself up after failure and figure out how to better yourself. You must not question your ability or potential to do great things. It is right to pursue bets that can elevate you versus bets that just validate who you are. All of this is infuriatingly common sense.

However, chasing rejection is still an uncommon pursuit. It feels foolhardy and the lack of a ‘Yes’ feels like you are going off-track. At this time, remember that the ‘No’s’ add up as long as you learn from every situation. In the words of Chris Paul, ‘just keep stacking days’, and you will realise that you are evolving for the better. It gets hard but you have to keep at it. Chase that rejection and the one after, because these take you closer to a life-changing acceptance.