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How to Overcome Life's Big Disappointments

How to Overcome Life's Big Disappointments

Life is disappointing sometimes. 

I hope this doesn’t come as a surprise to you. Someone should’ve told you that things don’t always work out the way you expect them to. Ideally, your parents forewarn you about this, and perhaps even prepare you for it. 

Unfortunately, most people don’t know how to handle their disappointments. And the only person who has taught them anything helpful in this matter is Mick Jagger singing “You Can’t Always Get What You Want”.

In many ways, big and small, life can feel unfair. Our expectations grow in our hearts unannounced, and we only notice them when they’ve been uprooted and left to wither in the sun. 

If you don’t know how to manage your disappointments, and process them in a healthy way, you will become cynical. While it might feel good to be cold or detached from your disappointments for a while, the benefits of being jaded never last very long. Cynicism is cyanide for your inner child. 

Disappointments lead us to a fork in the road. We either choose to address, and overcome, our disappointments–or we double back over the same ground and live in denial over the injustice of it all. 

Here’s how I’ve learned how to process my disappointments. 


Don’t pretend like it didn’t bother you. It did. You had a desire for a certain outcome, and it didn’t happen. If you don’t acknowledge it, you’ll be forced to lie to yourself and pretend it didn’t matter. 

But it did matter.

We learn to brush off small disappointments all the time. We go to a restaurant and they aren’t serving the thing we really wanted to order. We hoped that person would show up on time and they didn’t. We wished someone would’ve held the door open for us when we were carrying all that stuff in, but no–we’re out here, in the cold, groping around for our keys while they seem to jump from pocket to pocket. 

Maybe some of these small disappointments don’t break us. But the bigger ones do. When something or someone disappoints us, we either have to confront our feelings or lie to ourselves. 

The lie we try to make ourselves believe is that we didn’t have those expectations in the first place.

Here’s the truth: if you’re still stuck thinking about it, and if it’s keeping you up and night, and if you’re suppressing your emotions–then you did have expectations. And they came up short.


After you acknowledge what you’re disappointed in, you have to be honest about your sadness. Disappointment needs to express itself through mourning. Give yourself permission to grieve in a healthy way.

Notice I said, “in a healthy way”. If you begin weeping in the food court because they’re all out of poutine, you’re probably pretty bottled up to begin with. But the reason why small things might be so difficult for you is that you’ve never learned how to express the appropriate level of sadness over your disappointments! 

“Life isn’t fair.” That’s the full extent of how some people were taught to handle this kind of pain. What they’re essentially saying is, if you have to acknowledge your disappointment, then just take it off the chin and move on afterward.

You have permission to feel sad about your disappointments. But grieving well means your level of sadness is the right size and duration for the matter at hand. 

Permission to feel sad is not the same as permission to stay sad. If you’re going through it, then by all means, go through it!


If some people get stuck at the stage of expressing their grief, it’s only because they don’t know how to choose hope for tomorrow. Their disappointments have clouded their judgement and they’re stuck in the pain. They obsess over what went wrong and lament how they wish they had a time machine to go back and fix the past. 

The problem is their present is ruining their future.

Hope is not a wishy sentiment. Hope is resolute and steadfast–provided it’s put in the right things. The anchor isn’t keeping the boat in place when it’s sunbathing on the poop deck! You have to drop anchor in the midst of the storm in order for hope to function as a source of strength for you.

Maybe you have to re-evaluate what you put your hope in, too.

Hope, in itself, is a form of expectation. It’s the joyful expectation of good. If you’ve been disappointed, it feels so counterintuitive to hope again, because you feel like you’re setting yourself up for another disappointment! 

But if you refuse to hope because you’re afraid of being disappointed, you were without a doubt placing your hope in the wrong things. 

Hope cannot be placed in your favourite outcomes–your imagination over the future will sometimes let you down. And it can’t be placed in people–that will make you codependent, and nobody’s perfect.

Hope is only steadfast and sure when you believe the goodness of tomorrow will be greater than today. 

For myself, as a Christian, I call this placing my hope in God. To me, He’s the source of all goodness–so He makes my future meaningful. I get up in the morning believing I have a purpose, even if I have to process through my pain.

But even if you don’t believe in God, you can place your hope in a better future. You can lower your expectations over your circumstances, and approach your life with a little bit more childlikeness. 

You can, instead, place your hope in a coming day where you will feel peace and fulfillment–even when life isn’t going your way.


If I make it this far, then I usually feel pretty good about life again. But I’ve discovered how important it is to learn the right lessons out of life. Once I have hope again, it’s the perfect time to check my heart and grow by what I’ve just gone through.

Maybe my hope was in the right place–but did I set my expectations too high?

Was there another outcome–one I couldn’t see at the time–that would have been better?

Why did I want this to go my own way? 

How can I keep myself from cynicism–especially if this same disappointment happens again?

I ask myself these questions because I want to make sure, more than anything, that I am not trying to manipulate the outcomes of my own life. I want to hold onto my future lightly. I want to set my expectations in healthy ways. I don’t ever want to coerce or manipulate to get my desired outcome. 

I don’t want my life to be marked by my own demands. 

I want to be surprised and delighted again, because I haven’t set the standard so impossibly high.

Most of all, I want to live with the maturity to handle life’s disappointments when they come. I know that the prophet Mick was right about me not always getting what I want. 

But I believe he was also right about his next line, too. Hope will always make sure I get what I truly need.

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