How to Be Brave and Send an Email You Don’t Want To

Getting stuck when you go to send that email? This will help.

The majority of email messages that you get can either be easily processed or really aren’t worth your attention anyway. This is one of the fundamental principles of Email Triage, and it’s true whether it’s our system or any other that you find or create. This principle is obvious upon consideration, but the way a lot of people check email (rather than process email) doesn’t really come to grips with this.

The email messages that remain and get stuck typically involve:

  1. Making a decision
  2. Creating something (a solution, a plan, an asset, a proposal, art, whatever)
  3. Setting or enforcing a boundary
  4. Being vulnerable (making an ask, apologizing, coming clean, etc)

What rests underneath each of those four categories, though, is fear. Fear of making the wrong decision. Fear that the solution won’t work or be liked. Fear that whatever needs to be created will be rejected. Fear that someone will not like you if you start saying no. Fear that people will hurt or shame you if you’re vulnerable.

You Have to Be Brave

Yes, this is another one of those scenarios where fear is the highest common denominator.

Which means that your way forward through these emails is more of a heart game than a head game — in each case, the solution isn’t figuring out what else you need to know (which feeds the lie that “more research” will make it easier); but figuring out what you need to do to be more courageous.

When framed that way, a common first reaction is frustration or exasperation. I know this first hand, because I hold a metaphorical punching bag for my private clients, and it often comes up for our Email Triage customers who write in and tell me they’re stuck. It gets even worse when I refuse to give them my recommended resources on how to be more courageous.

The root cause of the frustration is that the person often then knows that the only thing between them and whatever’s on the other side of that email message is their willingness to be brave. No more research. No more re-editing or re-crafting the email message. No more punting the frog for another day.

The backpedaling that normally starts here, though, is that then people want to wait until that chimeric time when they’re going to feel much more up to sending it. While it’s true that it’s a lot harder to summon your courage when you’re in a HALTS state — hungry, angry, lonely, tired, or sick — the reality is that, outside of those scenarios and maybe a good coaching or mastermind session that fires you up, you’re not going to be in some Zen state. Furthermore, the way most of us are living, it’s a rare day that you’re not going to be in one of the HALTS conditions.

Here’s where we have to remember that courage isn’t the absence of fear, but the response to fear. As I’ve said to people who tell me that they believe that they’d cry in a combat scenario, it’s not that the tears aren’t there, but that you learn to fire through them.

Muster Up the Courage and Hit Send

The practical takeaways here are thus:

  1. Whenever you’re planning something that requires you to send email of the type outlined above, give yourself extra time, space, and self-compassion. Five email messages that require courage to send really can take you a month to send, even if they’re sitting in your drafts folder ready to be sent or someone has given you the perfect email. It’s not about the words; it’s about your fear.
  2. Emails that require courage to respond to or send need to go in Focus Blocks or they’re likely not going to be done or done well.
  3. In my experience, the length of your message is directly proportional to how much fear you’re feeling. The result is often sending someone an email that they have to work really hard to process, because it’s long and they have to figure out what’s really going on. You may need to write more for yourself, but you don’t need to send all of those words. You can write brief messages without being a jerk, presumptuous, or hoisting your fear on someone else. Your recipient is going to sense or recognize your fear one way or the other and likely already understand why it’s there.

Today’s challenge is to send one of those stuck emails. While starting with the one that scares you the most may provide the biggest relief, it may also trigger a vulnerability hangover that wipes you out for a while. But, before you send that email, figure out what you’re going to do after you send it so that you don’t spend the next hours or days hovering over your inbox to see what the recipient says. Going outside or for a workout can be especially nourishing.

You can do this. Will you?

Charlie Gilkey is an author, business advisor, and podcaster who teaches people how to start finishing what matters most. Click here to get more tools that’ll help you be a productive, flourishing co-creator of a better tomorrow.

Originally published at medium.com

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...


3 Reasons Fear Makes You Feel Stuck and What You Can Do About It

by Keysha Angel
nd3000 / Shutterstock

To Make Smarter Decisions, Look For Single Decisions That Remove Hundreds of Other Decisions

by Thomas Oppong

Why It Takes You Hours to Process Your Email

by Carson Tate

Sign up for the Thrive Global newsletter

Will be used in accordance with our privacy policy.

Thrive Global
People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.


We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.