Living with Disappointment

How to deal with disappointment from coworkers, everyday life, and friends/family

Christmas Eve 1995

I vividly remember a Christmas Eve night when I was 8 years old. I was so excited for Santa. The excitement kept me up far later than my parents expected, and as I snuck out of my room a couple of hours after bedtime I came across them setting up presents and my dad eating the cookies left out for Santa! 

This is an approximate representation of my reaction:

It was all the feelings an 8-year-old could feel - confusion, anger, bewilderment, wonder (wait… what about the Easter bunny?), sadness, disappointment, etc. I just didn’t want to believe it. 

While I’m generally less shocked by disappointments as I get older, I still regularly feel that same cocktail of emotions. I’m guessing you do too. In this article I’d like to explore a few disappointments most people deal with as adults and some tips on how to handle them.

Disappointed by Coworkers

At one place I worked there was a large scandal where two of my coworkers were sleeping together. Someone had arrived early at work and discovered them having a rendezvous. It was perhaps the most dramatic morning I have ever witnessed - when I got to work the cheating woman’s husband had shown up, there was a ton of yelling, and both of my coworkers were promptly fired. 

I was deeply saddened. I felt terrible for both of their spouses. I felt awful for my boss who had to fire them so abruptly. I felt bad for our clients who wouldn’t get their projects on time. I was disappointed that it had been happening at work; somewhere where I felt was professional and safe. 

While most experiences with coworkers aren’t this dramatic, there’s some learnings here:

• Trust can be shattered in an instant. If you miss a big deliverable, say something rude, or do something dishonest, your working relationship is effectively over. 

• Don’t have a “work spouse”. While you should strive to work effectively and build friendships, be careful that this doesn’t evolve into a romantic relationship (especially if you’re already married). Even if it’s truly platonic, others may see you as giving preferential treatment.

• Fire fast. My boss did the right thing to fire them immediately. Don’t let things persist. 

Jim and Pam: Perhaps the only acceptable “work spouse” scenario. 

Disappointed by Everyday Life

I remember one day at work where I was working on a media plan and pulled out what I had done last year. It was May 15th, and I was surprised to see that last year on May 15th I had worked on the EXACT SAME THING. That’s when I knew I couldn’t stay in the job, just doing the same thing over and over. 

Our lives are inherently repetitive. We have the same daily commute, work on similar annual projects, eat tacos on Taco Tuesday, and watch The Bachelor every Thursday night with a glass of wine. Routines are good until they aren’t. In my case working on the exact same project each year was killing me. 

So I found a new job. 

I strive to just try different things all the time. It’s a way of escaping too much “life repetition”. Here’s some things I’ve been trying lately:

• Reading. Rather than read my default genre (business), I’ve started to include classic, fantasy, and historical books in my rotation. I have been blown away with how reading Moby Dick has changed my perspective on life. Here’s 6 other books that have changed my life. 

• Outdoors. I regularly look for different hikes and places to visit. While I think it’s nice to have go-to places, the world is far too large to just do the same thing. 

• Food. I have really enjoyed learning to cook over the last few years, and it’s led me to trying some really interesting things, like smoked ice cream and making my own energy balls (It has also led to some disastrous cooks…). 

• Marriage. My wife and I try to do something different for our date nights. We have found that some of our favorite dates have been the simple ones that get us trying new things, like escape rooms or making pottery. 

• Shoes. I never buy the same running shoe twice - this gives me exposure to all sorts of different styles/brands and keeps my body in check so I don’t get “used to” a certain style. 

Some people really embrace the idea of always trying new shoes. 

(Unfortunately this is not my closet) 

Clearly there’s millions of ways to switch up your life. If you’re trying to add in good habits, I’d strongly recommend reading Atomic Habits. If you’re looking to add variety, I would recommend reading the book Switch: How to Change When Change is Hard. 

Disappointed by Family & Friends

The people who you’re closest with can disappoint you the most. You know more about their lives and the decisions they’re making than anyone else. And when they say or do something offensive, stupid, wreckless, or just make a bad choice (especially when it impacts you) it hurts. 

Ultimately I believe those we are closest to just need to know they’re loved and supported. When my kids make a bad decision it’s then when they need love the most. Note: this is really hard! 

In most cases you should (1) express your disappointment and (2) offer love/support. 

Recently my 5-year-old had a meltdown and was screaming, hitting, and just couldn’t be reasoned with. After letting him cool down in his room I followed my own advice of expressing disappointment and then offering love and support. He had melted down for a reason and really just needed love.

My 5-year-old (not melting down)

I think it’s the same with our adult family/friends (hopefully without the tantrums). When they make a poor decision (or even just a decision you wish was different) you have an important role to play to steer them in the right direction and let them know they are still loved. This is incredibly hard to do, but worth the effort.

As an example of this principle, I recently shared a story in this article about Helping Your Spouse Understand Your Career about how I had to work late one evening. When I texted my wife to let her know, she could have reacted in a wide variety of ways. But to her everlasting credit,  instead of getting upset, she offered to bring me dinner. 

In Conclusion

Life is full of disappointment. Whether it’s at work, in life, or by those you care about the most, there will be times when things don’t go as you planned or hoped. But you can always find methods to cope with the experience. Don't seek to run from disappointment, rather just embrace its reality and make the best of the situation. This has the tendency to turn you into a stronger, not a weaker or more cynical one.