Stop Protecting Your Feelings (And Start Getting More Clients)
The simple, uncomfortable habit that separates successful business owners from the rest
I felt a rush of butterflies I hadn’t experienced since asking a classmate to dance at a school disco decades ago.
The café was empty. I was the only customer.
I was clutching a fresh cappuccino, handed to me by a barista not 10 seconds before. Then, after she told me how much it would cost, she looked up at me expectantly and waited for payment.
Just ask, I thought.
Suddenly, a hundred situations played out in my mind at the same time.
She might think I was ridiculous. She might throw me out of the shop and ban me forever. Or somehow, I imagined an audience magically appearing behind me…and laughing.
Just ask.
It wasn’t like I was asking her to marry me. Although in the moment, it felt like getting on one knee and proposing was easier than what I was actually planning.
Before I could completely talk myself out of it, I opened my mouth.
“Could I have ten percent off this order?”
She paused for a second. Her head tilted slightly, just before her lips curled into a smile. “Well, all right then. Just because you asked.”
Cheap coffee was never the point
There’s a funny test in Noah Kagan’s Million Dollar Weekend.
It answers a simple question: Will you get out of your own way?
Go into a café and order whatever you want. But, just before you pay, ask for a small discount.
No context.
No defending.
Cheeky grin optional.
You may get the discount as I did. Or not. It doesn’t matter. The exercise is not about saving a few pennies on coffee.
It’s about asking for something, even if it makes you feel cheeky, or perhaps even a bit rude—when in reality, it’s perfectly inoffensive.
The funny part is how little we care that they might say yes. It’s how much trouble we go through to make sure they can’t say no. It might be a fear of seeming rude, or not wanting to inconvenience people.
But you know it’s bullshit when you think, “I’m trying to be a normal member of society” when in reality you were too scared of looking a bit silly for 10 seconds.
The world has to be allowed to hurt your feelings
Just think of all the situations people often don’t take chances.
the past client for a review.
the old contact for a catch-up or a reference.
the potential client if they’d benefit from your offer.
I started a photography portrait business recently and I’m almost embarrassed at how skittish I’ve been about offering photo shoots.
I’ve spent hours building up the business. Hand-picking my best photos from the years. Fine-tuning the copy on the landing pages.
But part of me has known for a while that the only way it’s going to really keep growing is this: get clients and go on more shoots.
I’ve got the contacts. Certainly people who would benefit from having up-to-date headshots. The funny thing was, every time I danced around the idea of sending out messages, I always found something else I could work on instead. Another blog post. Another round of photo edits. Another tweak to my branding and themes.
Anything to avoid giving people a chance to hurt my feelings.
It’s got to the point where realistically, my photography business won’t grow anymore with only things I can improve from the safety of my home. Even then, I probably hit diminishing returns a while back. And over the weeks, I’ve been forced to answer a simple question:
Was I genuinely improving the thing, or was I just postponing the moment somebody else got to decide?
Sometimes, the thing you’re avoiding is the thing you need
A “no” can tell you all sorts of useful things.
Wrong person. Wrong timing. Lousy offer. Not enough trust, or maybe people don’t care enough about the problem you’re trying to solve in the first place.
But you could be doing such a good job at protecting yourself from rejection that you refuse to get any of the above feedback.
What are you refusing to let the world reject?
Be honest.
Is there something you’ve been “getting ready to do” for months? Send the pitch? Ask for the introduction? Submit the article?
You might have a really good reason to avoid asking. But here’s a good test.
If you knew the answer would be yes, would you still be waiting?
No one can promise you it’s ever a guaranteed yes. But if the possibility of a “no” is what you’re really avoiding, then there’s a decent chance you're bullshitting yourself. Not only might that “no” be exactly what you need, but you’re shielding yourself from finding out if it would have been a “yes”.
For some reason, every time I thought of offering a photo shoot to someone, I pictured them ridiculing me or telling me where to go. But the funny thing is, in several years of trying to get out of my own way, I almost never hear the word “no”.
I’ve had people not reply—my offer wasn’t interesting enough.
I’ve had people say, “Thanks! I might take you up on that later.”
And in one case? “Thank you so much for the lovely message! I’m very interested in your very kind offer to do a photoshoot 😃”
Yes, some people are probably trying to protect my feelings. But it’s a far cry from the pointing and shaming I was terrified of for some reason. And if my offer were as ridiculous as I was worried it might be? I’d want to know that pretty quickly.
The worst scenario I could possibly imagine is spending years building a business that never had a chance of working because I was too afraid of giving people the chance to reject it.
So, stop imagining the stupidest possible reasons. Stop making up bullshit reasons you shouldn’t go for it.
Just ask.
If you protect yourself from ever hearing a “no”, you also deny anyone the opportunity to choose you.
It won’t always be comfortable. But the feedback you get is worth any number of “no”s you could hear in a lifetime.
P.S. If you’re up for it, do give Noah Kagan’s “coffee challenge” a try. Worst-case scenario is you pay full price for a cappuccino. Give it a go and let me know how it went!
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