The Disappointment Toolkit

12 minute audio. 9 minute read.

Four things you need in order to deal with disappointment well. Thoughts on expectation management, emotional courage, and unshakeable hope.


No matter who you are, or how well you prepare, disappointment is an inevitable part of life. If you want to live a life of significance, though, you must heal from past disappointments. By definition, disappointment is “the feeling of sadness or displeasure caused by the non-fulfillment of one’s hopes or expectations.” It can happen in an instant. One moment the sun is shining, your family is healthy, you’re dominating the workplace, and you feel like Princess Jasmine on a magic carpet ride flying on cloud nine. And the next moment, the carpet is pulled out from under you, you get fired, your family gets strep throat, and you receive a rejection letter from your favorite schoolall in the same month.

My first officially documented disappointment happened when I was 8 years old, on a field trip to Gold Country. During the daily diary time, it took me about twice as long as everyone else to finish my entries because rather than just jotting down what happened, I wrote out a detailed description of what I thought would happen.  My expectations did not always match reality. “I was expecting to eat dinner at circle tables, where you can hear all of your friends,” I wrote. “But we ate at rectangle tables, and it was too loud to hear. Also, I expected to catch gold nuggets the sides of sour patch kids, but instead I caught gold flakes the size of sand grains.”  The list continued.

As I grew up, my disappointments evolved along with my expectations and hopes, but they never went away altogether. I have learned that so long as we still care about life, and people, we will never completely escape disappointment. But I have also learned, that with the right frame of mind, and the right tools in your belt, you can heal from disappointments with your heart and hopes intact. Disappointment is like fire. It can burn down your dreams and your dignity, or it can light the rocket that launches you forward. The difference depends, on how you deal with it.

Here are the 4 tools you need in your belt to deal with disappointment well.

# 1  An Expectation X-ray

Distilled down to its basic ingredients, disappointment is made of unmet expectation. Thus to handle disappointment, we also have to be aware of our expectations.  Many of us carry around hidden, unspoken expectations that sit like ticking time bombs waiting to explode.

As a practical expectation awareness technique, picture yourself as an airplane traveler and your expectations as your luggage. Before taking off on any meaningful life venture or transition, you have to send your expectations through various security checkpoints.

Frequent flyer tip one, travel lightly. No one needs to go through life with more than 50 pounds of expectations. And sometimes, even three ounces of the wrong kind of expectation can be dangerous. Tip number two, don’t hide anything in your coat pocket or shoes and be transparent with your co-pilots and co-passengers about what you plan to bring onboard. Start by making a list of every existing expectation you can think of. Write down what you expect from yourself, your friends, your coworkers, your Christmas vacation agenda… anything goes.

Then, scrutinize your list with as much intensity as a TSA official examining a carry-on baggage screen. Slow it down, put it in reverse, invert the colors. What do you see? Are your expectations the healthy and reasonable type that you want in your overhead compartment? Or are they unrealistic and based on things outside of your control?

Expectation Examples

  • Expecting your significant other to listen to you, is healthy. Expecting them to text you every five minutes, on the minute, is not.
  • Expecting yourself to prepare for a podcast is within your control, but expecting it to go viral on day one, is not.
  • Expecting the “yes RSVPs” to show up at your holiday party, is reasonable, but expecting your estranged, extended family members to link arms in a rousing chorus of Kumbaya, is beyond your control.

X-raying your expectations is not about lowering your life standards or renouncing your optimism for good things to come. Rather, checking your expectations is about taking an honest inventory of your assumptions so that you can communicate accordingly and prepare for take off!

#2 Emotional Courage (aka the willingness to feel anything)

Technically, disappointment is just a feeling. But it’s prickly and painful enough, that many of us do anything we can to avoid it altogether. Ironically, the attempted avoidance of discomfort in the short term only leads to more pain and disappointment in the long term—for two reasons.

First: When you deny the pain of a present disappointment, then you stunt the necessary healing and growth process which helps you move into your next chapter. In other words, denial keeps you stuck.

Second: If you try to protect yourself from feeling disappointment in the future, you have no other option than to shrink your life and dreams down to the size of your disappointment tolerance—which is probably not very high, if can’t stomach the feeling. In such cases, the very feeling that you flee from ends up owning you, by causing you to live small, and disappointed by default.

Surgery or Scar Tissue?

Here’s an example to illustrate the concept.  It’s the championship soccer game, and the star players on opposing teams, Mario and Luigi, collide while sliding for a ball during the 89th minute. Each of them breaks a leg on impact and the crowd holds their breath watching for the response. When Mario feels the sharp pain shooting through his body, he signals the medical tent, right away because he knows he needs help. After initial first aid, the medics whisk him off to the hospital for an x-ray, and later, surgery. Undeniably, it’s a disappointing way to end the season and a painful process of healing. However, within a couple of months—after active recovery, and hard work in Physical Therapy—Mario is back in the game, stronger than ever, and full of injury prevention tactics.

Luigi, on the other hand, feels the pain for a brief moment, and panics at the thought of getting sidelined by injury. Instead of calling for a sub, he pops some painkillers, hoists himself to his feet, and insists that he is fine. For the next few months, Luigi hobbles around with a lingering injury, thickening scar tissue and a stride that worsens every day. Even though he opts out of surgery, his process, of chosen non-recovery, is also painful. So much so, that when the next season rolls around, Luigi is so afraid to get back out on the field that he quits soccer and remains bitter towards Mario for years.

Disappointment is meant to be a transient feeling, not a permanent lifestyle. When you experience disappointment, acknowledge the pain, and do triage right away. The sting of antiseptic is far better than the festering infection of a wound unattended to. If you cultivate the emotional courage and allow yourself wade through discomfort, you will experience a richer hue of joy on the other side of your pain.

# 3 Adaptability

The two most common phrases I have uttered in times of my own disappointment are “this is not how it was supposed to turn out,” and “this is way different than what I imagined.”  Often, the anguish of disappointment comes not from irreversible tragedy, or devastation (while those things do exist) but rather from our despair about the discrepancy, between what is, and what we thought would be. It’s as though we hold our own ideas and predictions as the gold standard for what should come to pass. But to navigate disappointment, we need a high level of adaptability.

Road trip analogy.

A big group of friends divided into two cars, one  Forester and one Audi,  caravans northbound for an Oregon coast getaway. Trunks are stacked with surfboards and spikeballs. Glove compartments are stuffed with clam chowder menus and coastal coffee cards. It looks a dream road trip is about to unfold. That is, until, they hit road closure. Highway 101 is under construction and blocked off from Eureka all the way to the Tillamook Forest. That’s unexpected. What will they do?

The fixed mindset Forester crew is sorely disappointed and begins to complain about what a waste of precious time off work this is. Instead of accepting responsibility for not doing the research on the roads, they blame the road service. In protest, they set up a camp at the junction for several nights, before finally canceling the trip altogether and driving home in angry silence.

The adaptable Audi crew, on the other hand, also feels disappointed, but only for a short time. They forgive themselves and the members of the other car, for the oversight. And then, they re-calibrate their GPS systems, change course, and enjoy a mountainous adventure through Highway 5 and Lake Shasta, instead.

Life disappointment can look a lot like road trip disaster. You will plan to go to a certain destination, via a certain route, with a certain person. And then, a bridge will collapse, your main companion will need to go under personal construction, or there will be a forest fire at your chosen destination. It happens.

The important thing is that you have the adaptability to see your options, rather than fixate on your limitations. Adaptability will enable you to live with wonder rather than apprehension. If your life doesn’t look like how you imagined, that does not always mean you are on the wrong path. After all, we worship a God who is far beyond our imagination.

# 4 Unshakeable Hope.

Out of all the disappointment tools in your belt, perhaps the most important is an unshakeable hope.  In everyday conversation,  hope is typically surrounded by words that indicate fragility such as ‘shattered,’ or ‘crushed.’ Hope, as described in Bible, however, does not disappoint, and renews our strength.

Whether hope makes your heart sick or makes your is heart soar depends on where you place it. One time, I was devastated by a relationship that didn’t work out. Every Sunday, for months following, I visited the prayer team, and requested them to pray for “my hope to be restored.”  Clearly, I had hope misplacement problems. See, hope does not run away with a person, plummet with the stocks, or set with the sun, unless you install it in insecure places.

Living life with insecure hope is akin to sailing out on the open sea, in a boat made of rotting driftwood. While it may stay float just fine on a sunny day, it will get shipwrecked, and raided by pirates at the first storm of the season.

Living with your hope in God, however, is more like sailing on a Cruise Liner. It doesn’t matter if there are fifty mile per hour winds outside, you can still feast on tiramisu and take a nap anyway. You trust that you’re secure.

As Christians, we are called to be a people of Hope. While we might hope FOR things on earth, we place our hope IN things of Heaven. When our hope is in who God is, disappointment is a temporary, perplexing sting, but not a crushing crisis of faith. Don’t let the enemy steal your joy because of your circumstances. Rather, let your disappointment come face to face with unshakeable hope and unwavering belief of God’s goodness. Keep your eyes fixed not in what is seen, but in what is unseen. Finally, trust that no matter what happens, the best is yet to come.



2 thoughts on “The Disappointment Toolkit

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s