Ask and Ye Shall (maybe) Receive

Avik Ashar
3 min readMar 2, 2021

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Let me ask you a question.

Do you have any regrets related to speaking up, where you could have asked that hot person out, asked for a raise, asked for help, just asked for something… And you didn’t?

Odds are you answered yes.

Let me flip this question around.

I have a briefcase of money (let’s say $1 million big ones). I offer you a coin. Heads, you get the money, Tails, you get a handshake.

Would you do it?

Odds again lean towards yes. Your odds are pretty much 50%

Let me add a third option

You could walk away. In this case your probability of receiving $1 million bucks is ZERO.

The World is Yours

Fear of Rejection

Rejection. No. Go Away. Nahi (hindi). Nyet (Russian). Nein (German)

I could go on. As Human Beings, we automatically shy away from all forms of rejection. It’s a fear we can almost taste, that paralyses us when we are about to take a leap, when we are about to ask for something.

The root causes of this fear are numerous (and I’m definitely not qualified to dive too deep into them) but I will attempt to.

#Failure: Psychologist, Guy Winch, explains it (fear of failure) as causing people to “unconsciously sabotage their chances of success, in a variety of ways.” I particularly love this definition as I can relate to it at so many times in my life.

Hot woman at the bar? I won’t go up and talk to her because ‘I’m having a great night by myself’ or ‘I’m not ready for something right now’.

Amazing job? ‘But I love working for 14 hours and very little money where I am’, ‘They are probably just looking for XYZ’.

We are so scared of failing at something that our brains manufacture reasons to NOT go for it.

This is partially linked to our societal celebration-of-success. We do not celebrate failure. We don’t even showcase failure. It’s a taboo topic.
So when it comes down to asking for something we want to be sure we will succeed.

#Shame: What happens when you face rejection? I used to draw away, cocoon myself and lick my wounds. I felt worthless, powerless, humiliated.

Unless you’re a Buddhist Monk on the verge of Nirvana, some part of our self worth is inexplicably linked with society. Whether they view us as smart, fit, attractive, successful etc.

Rejection of my request (help, job, raise, date..) felt like a Rejection of me as an individual, chipping away at my self esteem.

#Likeability: We all crave to be liked. It’s an inherent human need to seek validation through being ‘liked’ by other people.

This tends to create a dilemma. Asking for something (payment for extra services, help shifting homes) carries an emotional cost.

  • What if I piss him off?
  • Will she think I’m cheap?
  • Will they stop being my friend?

Whether it’s Failure, Shame or Wanting-to-be-liked that’s holding us back, the end result is we don’t get what we want. (and I want ice cream)

GET THE ICE CREAM!

Asking is free

Borrowing some lessons from this fantastic post by Oz Chen, we need to flip the mental model.

Asking is Free. There’s no cost to it. In economic terms, unlimited upside, virtually no downside.

It’s time to flip your mental model.

Asking is like a muscle, the more you exercise it, the easier it gets.

Ask any salesperson on commission (and EVERYONE should do this), asking for something, in their case selling, is the only way to put food on the table.

Every successful businessperson I have had the good fortune to encounter has mastered this skill.

Whether it’s asking for that corner table with the reserved sign on it, a better price for a shipload of steel or a date, they always ask.

And fairly often, they receive!

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Avik Ashar
Avik Ashar

Written by Avik Ashar

Investor @ Artha Ventures | Exited Founder | Experienced Operator | I drink whisky and read fantasy fiction

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