Always Ask First

One of my classmates at Yale is taking a course at the business school called “Mastering Influence and Persuasion.” Last month, one of his homework assignments was to practice getting rejected.

He decided to do his homework at an upscale hotel down the street, one with uniformed doormen and sparkling chandeliers.

Dressed in his usual t-shirt and jeans, my friend ambled through their beautiful glass doors and asked the man at the front desk, “Excuse me, sir, do you have any vacancies tonight?”

The guy replied that they did have a couple of rooms available.

“Great. What’s the rate for the cheapest single?”

The response fell somewhere around $300 or $400.

“Cool,” said my friend. “Could I…uh…get that room tonight for free?”

The guy looked at him like he was crazy.

My friend said, “I don’t have enough money to rent a room, but it would be great if I could stay a night without having to pay for it.”

Incredulously, the guy at the desk explained that this was against company policy.

So my friend said, “Okay, sir, I understand. Could we negotiate some other arrangement? For example, I’m in an a cappella group – I’d be happy to sing for your customers in the lobby, in exchange for one night’s stay.”

At this point, the guy politely told my friend to get the heck out of his hotel, and my friend politely got the heck out.

Afterwards, when my friend told me this story, I thought it was a really interesting assignment. It was the first time I realized how much I live my life in fear of rejection. And it was also the first time I realized how harmless a lot of rejections really are, when you stop being afraid of them.

My friend’s professor based this assignment on the project “100 Days of Rejection” by an entrepreneur named Jia Jiang. After his startup got turned down by investors, Jiang realized that one of the main roadblocks in his path was his own fear of rejection. To desensitize himself, Jiang spent a hundred days asking for simple, relatively harmless things that he thought likely to be rejected. For example, he asked strangers to give him compliments. He asked to assemble his own sandwich at Subway. He asked to make an announcement over the intercom at Costco.

Speaking as a relatively shy introvert, I know I’d feel starkly uncomfortable making any of those requests.

But here’s the thing – every successful person I know has, at some point, faced the risk of worse rejections. And maybe they felt starkly uncomfortable asking for what they wanted, too. Still, when it really mattered, they pushed past their discomfort and asked anyway.

To me, that’s the single most underrated trait a person can have – the courage to ask for what you want, even when you’re afraid.

Ninety percent of the time, you might be told to get the heck out of the hotel. But in the long run, you’ll get a lot farther than if you’d been too scared to ask at all.


Hello! I’m Ashi, the Content Creator of the My Halla Blog and I appreciate you stopping by. I hope the Halla Blog is an inspiring and informative resource for you. Born and brought up in Dhar, I completed my education in Rajasthan. I am passionate speaker by day and a writer by night. Full of enthusiasm is what best describes me. I’m a self-motivated person and I get inspired from my own life experiences and other people’s life stories to write. When I’m not working, you would find me teaching small kids on weekends. I believe in giving back to society and making a positive difference in the life of others. A cup of coffee and some scribbling is what keeps me going! Want to know more?Connect with me on

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