Disappointing Someone

When I ask people about their greatest fears, I often hear phrases like:

  • disappointing someone I love

  • being a disappointment

  • my parents being disappointed in me

  • feeling disappointed if it doesn’t go the way I want it to

  • disappointing myself

We all face disappointment in life, so why are we so afraid of it?

If you really examine disappointment, it is a feeling of sadness that our expectations were not met. So, let’s break that down even more: We are afraid of a feeling. A yucky uncomfortable feeling. A feeling that comes because we imagined one thing and experienced something different than that.

The covid quarantine days taught us all a lot about disappointment. Things were canceled. We were disappointed. it was a yucky feeling. But did we survive it? Yes. We know we can survive disappointment. In fact, we got used to it. We started to expect to be disappointed. We are getting better at this all the time.

Disappointment is just a feeling and we can manage our feelings.

Glennon Doyle, in her book Untamed, tells of a conversation with her daughter who feels obligated to join a club her brother belonged to in school. She doesn’t want to join the club and says to her mother, “but I don’t want to disappoint him.” Glennon responds, “Listen. Every time you are given a choice of disappointing someone else or disappointing yourself, your duty is to disappoint that someone else. Your job, throughout your entire life, is to disappoint as many people as it takes to avoid disappointing yourself.” Her daughter asks, “Even you?” Glennon responds, “Especially me.”

This took my breath away when I read it and it did again as I typed it for you. When I first read this story, I had to go back over it a few times to make sure I read it correctly. Wait?!?! It is okay to disappoint someone? Especially a parent? This was such a foreign concept to my brain. I have lived my whole life thinking my job was to never disappoint anyone. My job was to please all of the people and do all of the things, and never ever let anyone down. For the first four decades of my life, I thought it was better to disappoint myself to make someone else happy. I now see that I had it completely backward.

If we live our lives in fear of disappointing someone, do we ultimately live a life of disappointing ourselves?

I think so. Here are some examples people have shared with me:

  • A desire to change my major in college, but dad will be disappointed.

  • A longing to call off the wedding, but guests will be disappointed.

  • An urge to ask for a raise, but what if it leads to finding out that they are disappointed in my work?

  • Readiness to come out about sexuality, but afraid of the look of disappointment in a parent’s eyes.

  • Wanting to tell the truth, but knowing someone will be disappointed.

  • Dreaming of a creative or entrepreneurial project, but what if I’m disappointed in how it turns out?

As you read those, you might be thinking, "‘just do it, live your life!’ But, when it comes to your own fear of disappointment, is it that easy?

Glennon gifted her readers with this story. A life of pleasing everyone else leads to resentment. Resentment comes when our giving and receiving get off balance. Often, we deny ourselves and then feel mad at the other person after we give them what they want. I have had this flavor of resentment many times.

So here is our homework for this week - let’s get a little more comfortable with disappointment.

Who can you disappoint this week?

What can you say “no” to?

Where can you let someone down, but save yourself?


I’m off to disappoint someone now…but, I hope it isn’t you. (I’m a work in progress!)

Much love!