I just read an interview in the New York Times about what it’s like to be a sociopath. The subject of the interview, Patric Gagne, is preparing to publish a book called Sociopath: A Memoir.

The article highlighted that I am not a sociopath because I care deeply — often too deeply — what other people think of me. Most of us do.

And caring too much about other people’s opinions limits us from doing scary things like asking for what we want.

Asking is hard

Asking for what you want can be really hard!

Let’s use a concrete example:

I would like to take you to lunch.
I know the best secret sandwich spot in Oakland.
​And then finally the ask: Would you like to come with me?

Asking means risking being told “No.” Or worse yet, getting laughed at.

Asking is even harder when we’re trying to sell something $1000 tickets to my annual Responsive Conference.

I am confronted by insecurities like “What if they take offense to me asking?” or “What if they agree, but then hate the experience?”

Asking is scary because of the risk of rejection.

What is rejection?

When I compare myself to someone who actually doesn’t care what people think of her, like the author of Sociopath Patric Gagne, I have to define my terms.

What is rejection?

Rejection is caring about what people think, even if I shouldn’t. It means basing my decisions and actions on how I think someone else might respond.

Rejection is the fear that you are going to be judged, or worse yet, ostracized by your peers.

Throughout human evolution, getting ostracized meant likely death. Infants can’t survive without the support of their adult caregivers. Prehistoric humans couldn’t survive without the support of their community.

Today, we live in a world with eight billion people. Even if we were to get excommunicated (which isn’t likely to result from a single request), that probably wouldn’t mean the death that would for our prehistoric ancestors.

The world is a lot safer and more convenient than it was tens of thousands of years ago!

Motivated by the opinions of strangers

I can rationalize why I should care about the opinion of my best friend. If I acted in a way that a close friend found unacceptable, I’d like to know so that I could at least consider changing my behavior.

I’m also highly motivated by what my parents think of me. This is less appropriate, because, at 37-years-old, I’ve outgrown the need for their approval.

Worse, I’m motivated by the opinions of strangers. When I meet someone walking down the street, I wonder what they think about me.

Most of us are too busy judging ourselves through the eyes of strangers to pay close attention to what we want, recognize our fears and then ask for it.

I haven’t found a magic solution to not caring what people think of me, but here are some approaches to overcome the fear of rejection.

How to care just a bit less

Courage

We have a word for acting in the face of fear. That word is courage.

And most of us want to be more courageous.

A good way to practice being courageous is to practice asking for what you want. Incidentally, you’ll get better at asking!

Identify what you’re afraid of

The first step to overcoming your fear is to identify what it is that you are afraid of.

Fear is often an amorphous emotion that clouds even our ability to notice what it is that we’re afraid of.

First recognize that you are fearful and then identify the specific thing that you are afraid of.

The worst case scenario

When I opened up Robin’s Cafe in 2016, I did so with the knowledge that if it failed, I might end up $50,000 or more in debt.

The only way I was able to step into the unknown and open the cafe was to literally calculate how long it would take me at $15/hour (plus tips!) to earn back that $50,000.

Ask yourself “What’s the worst thing that could happen?” Write down a few of your answers.

Practice asking

Asking takes practice.

Just like anything else worth doing, learning to ask for what you want is a learned skill that you can improve with practice.

Unless you work on a sales team, you probably don’t have a lot of experience selling, asking or risking rejection.

Make facing rejection a deliberate skill you practice.

Homework

I’ve started a new practice this year of complimenting strangers on the street. Any time I walk by someone who’s clothing or style I admire, tell them so.

It seems like such a small thing – and it is – but I, for one, and most of us are hesitant even to pay a compliment.

For the next week, complement someone you see at least once a day on some element of their clothing or style. As you do so, notice your discomfort – and complement them anyway!

By the end of the week, you may find that you are less uncomfortable than initially.