If you don’t ask, the answer isn’t no

There’s a common idea that “If you don’t ask, the answer is no.”

The problem is that when we don’t ask, it doesn’t feel like rejection. The consequence is silence and inactivity, which feels less bad than an actual rejection.

Thus, we are reinforced for not asking.

I’m still nervous when I quote my hourly rate.
I still hesitate before asking a beautiful woman on a date.

But my three profitable businesses of the last decade succeeded only because I was able to overcome my fear of asking.

Here are a few ways to motivate yourself to ask for what you want.

The desire to prove yourself

Every entrepreneur I’ve met is either fueled by a chip on their shoulder or because they are chasing something they love. And, in the beginning, a majority have something something to prove.

When I started Robin’s Cafe, I had a chip on my shoulder. I wanted to do something everyone told me was impossible. I wanted to prove my parents wrong!

This isn’t what I think of as clean fuel. The desire to prove someone wrong is a great motivator, but it doesn’t leave you feeling good about yourself. It comes with consequences like self-loathing or burnout.

When you are trying to prove yourself, you make the cost of inaction more painful than the risk of being told no.

Away from pain

It is painful to ask for what you want and be rejected. But there is often an even bigger pain that won’t get solved if you don’t ask.

You can also use that impetus to move away from the shame or humiliation of defeat. What you want is what you are moving away from not happening if you don’t ask.

Loss aversion

We are motivated by more potential of loss than by gain. This is loss aversion is – the human bias to prioritize avoiding losing even over achieving the equivalent gains.

When you don’t ask for what you want, it doesn’t feel like a loss. But it is. You are losing the opportunity that you’d otherwise have had a chance to achieve.

Anytime you don’t ask for what you want you are losing the opportunity.

Towards joy

Joy, delight and enthusiasm are powerful motivators. They are also a cleaner fuel – they don’t come with the negative consequences that a chip on your shoulder does.

When I started Zander Media, I was really curious and excited to learn how to do digital storytelling on the Internet.

That motivation – joyfully pursuit of something you want to accomplish – is an incredible motivator, if you can find it.

Make your purpose clear

Have a clear purpose – a reason that you are attempting something difficult.

I started Zander Media because I wanted to figure out how to do digital storytelling on the Internet.

And I wanted to earn money.
I wanted to do great work for our clients.
Then, as I hired employees, I wanted the company to be a great place to work.

Identify the reason you are tackling a particular challenge. When you know why, you are much more likely to attempt it.

Have a lot of reasons why

Even more than a single clear purpose is having a lot of reasons why.

I started writing Snafu because I wanted to practice writing and improve as a salesman.

Then, as I told friends about the newsletter, I was writing for a handful of other people. Those few people grew into several hundred, and now this newsletter has nine thousand weekly readers!

While not all of you write back to me (you should!), that is nine thousand reasons why I do my best to write a useful newsletter each week.

We say that “If you don’t ask, the answer is no.” But that’s inaccurate. The answer is silence, which feels better than rejection.

Whether because of a chip on your shoulder, chasing joy, or serving a cause greater than yourself, hopefully this article gives you some cues towards action.


I think a lot about where your motivation comes from. My desire to do handstands, for example, stem from my joy for incremental progress.

Pick an objective you are currently chasing: trying to learn to sell something, persuade someone, or change your own behavior.

Write out five reasons why you want to accomplish that goal.

Then, examine where you draw motivation for that objective.

Are you trying to prove something to yourself or someone else, afraid of losing out, chasing your objective for the joy of it?

Until next week,

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