Asking is Free

I was cringing inside.

This was taking too long to just order a piece of toast.

My friend loves to go off menu:

We’ll start with the tostada con tomate …but is it possible to just do half of this, and get the other half with salmon? Can you bring extra sea salt, and oh, some olive oil too?

During these RequestFests™, I’d get embarrassed that we were asking too much of the wait staff. Of annoying other people.

The amazing thing was, the majority of the time, she got exactly what she wanted:

Spanish style toast. Simple but so damn delicious.

And it cost her nothing to ask.

This small, pedestrian example made me question:

What if I truly asked for things that I wanted?

And a darker one…

How many times in my life have I denied myself what I wanted, simply because I was afraid of asking?

  • Mediocre haircuts because I was afraid of asking my barber to do more.
  • Substandard meals because I didn’t want to ask the kitchen to redo a botched order.
  • Not asking to get paid for extra hours I committed to on a project.

(Do you have any examples from everyday life? I’d love to hear in the comments.)

If asking is free (and often beneficial), then why was I so afraid to do it?

The Fear of Asking

It struck me how shamelessly my friend made her requests.

Shameless. That’s just the word. If she was shameless in asking…then I was shameful in asking.

Doing some root cause analysis, I realized that this shame came from my fear of not being liked.

  • What if I annoy others?
  • Will they think I’m cheap?
  • What would they think of me after making this request?

I developed a fear of rejection, and it all showed up in a piece of toast.

There should be no moral judgment by merely asking.

After all, businesses make money by providing for their clients. Restaurants are meant to serve their diners. Customer service representatives are paid to, well, deliver customer service.

On the flip side, here’s an opportunity to practice personal responsibility. If I’m unhappy with an outcome but don’t make a request for change, that’s on me. I have no right to resent others if I don’t communicate my wants1.

The best part is that sometimes you do get what you want…and the only cost is the discomfort of asking.

Changing my mental model around asking

”You don’t like asking for help, do you?”

It was a couple hours before a Dinner with Strangers event, and a friend watched me scramble to organize everything myself.

”Let me help you. Make me feel useful.”

Little moments like this loosen the screws of my reality –

My shame-based mental model had me assume that I was bothering people by making requests.

This incurred an emotional cost that disincentivized me from asking.

Now I see making requests as an opportunity to make others feel good and useful.


Ask great things of yourself and others. They might just rise to the occasion.

I realized the reverse was was true in my life.

When people asked me for help, I was glad to help.

When great things were asked of me, I rose to the occasion.2

Asking is a skill

With practice, the emotional cost of making requests goes down.


At first, there is an emotional cost incurred. But over time, as we accumulate skill and comfort, asking is free.

Some questions to try on:

  • Can we try this?
  • Is this customizable?
  • Are there other options?
  • May I suggest something?

Not only is asking free, but it’s also an empowering way to include others and live a more fun, responsible life.

  1. AKA “hidden contracts,” which are unspoken social expectations. Don’t resent someone for not giving you something you didn’t ask for.
  2. When former bosses and managers asked me to take on big projects, I was humbled they trusted me with a big responsibility. I suspect that the biggest cause of employee disengagement is that big enough things are not asked of them.

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