hard conversations

Putting off hard conversations doesn’t make them easier

Every hard conversation you put off is a pebble in your shoe. Each day is a painful step that you tell yourself “Not yet, I can’t stop and deal with this right now. It’s too much trouble or pain to face this, I’ll get to it later.” How many pebbles are in your shoe now? How many times throughout your day do you wince as you feel the pebble and dread dealing with it? How heavy is that emotional burden?

I realize you’re used to the pebble in your shoe. It is probably a dull pain but you endure it every single day. It must be so terrifying to think of dealing with this. I’m sure there’s people whose feelings will be hurt or crushed. Maybe you don’t know how it will go and you’re scared to find out. You’re acting like this pain or demon is locked inside a box and you’re scared to open it. Like dealing with the pain will suddenly overwhelm you. But look at all the days you’ve carried this burden, all the time you’ve spent limping and getting less out of life with this weight on your shoulders. Can’t you see? You’ve been trapped inside that box with your demons this whole time. Opening that box is the only way for you to get out.

The thing is, you will never feel ready to deal with this. The most important things in life are really hard and it’s impossible to feel totally prepared. Are you going to let that hold you back or will you use it as a license to do your best and move on? Pressing the call button on your phone might seem really scary, but it’s always going to be that way. You have something you need to say and you don’t have to feel ready to just try. This isn’t going to get easier, and every single day that you carry this burden you’re choosing to to get less out of life. When you’re 80 and you look back will you regret those days you can’t get back?

There’s some stoic solace in accepting that some things always feel impossible until they are done. It’s okay to feel sick to your stomach. It’s normal that being honest with someone might really upset them. Every single person on this planet has conversations they have been putting off, and there’s nothing wrong with you. So try to normalize this fear so you can act in spite of it. Recognize that someone wrote this post because they feel the same thing you do. Read my words knowing that 20 minutes ago I was petrified to click send because I probably just lost a friendship and I had been putting it off for a long time. Know that this rock had been scraping my foot raw and I was so horrified to take it out and try to heal. Know that I didn’t feel brave or confident or ready to click send. I felt nauseous and numb.

Being honest with people doesn’t always feel good, but it feels better than the alternative. And having that pebble out of my shoe is such a huge weight off my shoulders that I needed to tell someone. I needed to reach out to you and tell you that it gets better. I needed you to know that you’re not alone and you are strong enough to do this even if you don’t feel ready.

Putting this off is not going to make it easier – but it also doesn’t need to be easier. You’re strong enough now, and you’ve been limping for so long. You know what you need to do. It’s time.


Further reading: If this resonated with you then I think you would benefit from Meditations by Marcus Aurelias. Think of it as the pep talk a Roman emperor gave himself to work through the many hard decisions and conversations and discipline such a post entails. Stoicism has its time and place, but I find it incredibly helpful when I’m paralyzed by emotions. This can be a calm, logical rope to pull yourself forward when reactionary emotions are holding you back.

Leave a Reply