Good Question: How can I stop being such a perfectionist when I’m writing emails?

“Alex: I was wondering if you have any tips to help with ’email insecurity.’

I have an extremely annoying and time-wasting habit where I write an email and then AGONIZE over sending it. A simple two-sentence email can take me forty minutes to write because I re-read and re-write it so many times. Help!” –K.B.

Ah, yes. Email insecurity. A common plight.

Right up there with Internet Penis Anxiety.

I have 3 steps for you. Here we go:

1. Write an “easy” email, first.

Before tackling that “tricky” email, start by writing an “easy” one.

Say, a cheerful note to a friend. Or a fan letter to someone you admire. Something that feels low-pressure and effortless.

This will help to activate the part of your brain that’s associated with fluid communication and improvisational, creative problem-solving — instead of the part of your brain that’s associated with the paralyzing “fight or flight” self-preservation response.

2. Decide what you want your reader to feel, know and do.

Ask yourself the following three questions:

How do I want my reader to feel?

What do I want my reader to know?

What do I want my reader to do?

Once you answer those questions, getting straight to the point — without over-thinking or second-guessing — should be much simpler.

3. If all else fails: add your voice.

I’m a big fan of responding to delicate, sensitive emails using an audio note, rather than a written email.

You can record a quick message using Vocaroo (it’s free!) and then attach the mp3 file to your email.

In your email, say something like, “Hey! I’ve responded to your question with an audio note. See attached. Enjoy.”

It’s very unlikely that you’ll be misunderstood, once the person you’re responding to hears your tone of voice.

Plus, voice notes are rare these days, and kinda fun — they’ll be excited just to hear you, in the first place!

Most of all …

Remember that every time you place your fingers on the keyboard to blast off an email, you have an opportunity to add to the love in the world, or subtract from it. To elevate somebody’s spirits, or deflate ’em. To make somebody’s day, or dampen it.

Choose to be a Daymaker.

They will feel the love, in every word.

And you’ll never have to stress about hitting “send.”

Do you suffer from “email insecurity”? What kinds of emails throw a wrench in your day, or take up waaay too much time?