How to Cope with Disappointing Others

May 1, 2024 Dawn Gressard

Many people find it challenging to cope with disappointing others, whether a loved one, a friend, or a coworker. I am no exception. I will avoid disappointing someone if possible. We all know how it feels to be disappointed or let down, so why would I want to inflict that feeling onto someone else? I possess great empathy for others, almost to a fault. So, to know that I am about to confront someone and make them feel sad or disappointed makes me feel guilty, which then leads to depression. However, lately, I have been trying to reroute my thinking and people-pleasing tendencies to remember the positives and why I can no longer appease everyone to help cope with disappointing others.

Coping with Disappointing Others: My Conflict

For instance, I am in the process of transitioning to a new job. It will have a more secure salary, and I can still work from home part of the time. Unfortunately, that means I need to leave coworkers and a job I love, funded only by grant funding that is not guaranteed every year nor guaranteed to last the whole fiscal year. 

In this transition, I have to discuss with my boss (and friend) the possibility of leaving our mission to help service members, veterans, and their family members train to be peer support specialists in holistic mental wellbeing. My new job will start very soon, and there is only a little time that I can waste procrastinating on having a challenging discussion with my boss about leaving. 

I have agonized over how I will even begin the above discussion as I must cope with disappointing her. Will she be angry with me? Will she be disappointed in me? Will she try to convince me otherwise? Will I even get to say everything I want and why I have decided to leave for a new opportunity even though I genuinely believe in our purpose and mission? This conflict and pending conversation have had me in a tailspin, so much so that I have found myself not only under significant anxiety but also slipping into depression. 

How Do I Cope with Disappointing Others?

So, how do I cope with disappointing my boss, who has been so supportive of me for the past two years? Although I am excited about the future, this is also a significant loss. So, trying to stay upbeat has been hard enough, much less adding the pressure of telling my coworkers I'm leaving. 

In the past week, I have come up with some ways that will help me cope with disappointing others and hopefully divert any depression from setting in. 

Tips to Cope with Disappointing Others

  1. Giving myself a timeline -- Giving myself a set day to speak with someone about a particular decision will provide me with a deadline I must abide by. This way, I can do what I need to do, and my anxiety and depression will stay at bay until close to the deadline. 
  2. Journaling about my thoughts -- Journaling is always a go-to when I'm feeling upset or down. Here, I can write out what I want to say and remind myself why I chose what I did. While writing, I can also work out my feelings of disappointing others and feeling guilty before going down the road of sadness. 
  3. Talking it out -- This post is about coping with disappointing others. To avoid feeling bad about it, I try to talk it out with the person I think I am disappointing. This will not only prevent burning bridges but also allow me to understand how someone is feeling instead of assuming how they feel. 
  4. Remembering my toolbox -- As always, using the items listed in my wellness toolbox (puzzles, scary movies, ice cream, etc.) also helps me avoid getting too deep into a depressive episode.

Ultimately, my empathy and guilt for disappointing others are significant. They can often cause me to become depressed, especially when it comes to my children and loved ones. However, as I have gotten older, I also know I must make choices for my best interests. My tips on coping with disappointing others will be put to the test very soon. If anyone else has any other tips, I am all ears. Please let me know in the comments below.

APA Reference
Gressard, D. (2024, May 1). How to Cope with Disappointing Others, HealthyPlace. Retrieved on 2024, June 17 from

Author: Dawn Gressard

Dawn Gressard is a freelance Veterans Affairs benefits, mental health wellness, and suicide prevention writer and a trainer of a peer-supported suicide prevention and crisis intervention program. Find Dawn on X, Instagram, LinkedIn, and her personal blog.

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