5 Questions to Consider When Drowning In Disappointment

Disappointments are part and parcel of life. But if you don’t deal with it the right way, it can slowly consume you and derail your life.

Hence, it is so important to learn how to deal with disappointment.

In this article, I am going to share with you the 5 questions to ask yourself when faced with disappointment. These 5 questions will help you cope with that disappointment, and propel you to greater heights.

1.    Why am I disappointed?

When you are feeling disappointed, sometimes it can be difficult to explain why, am I right?

It just happens. However, to cope with it, you must first begin by rationalising your disappointment.

Ask yourself questions like why are you feeling that way? What in particular triggered the disappointment?

When asking these questions, it is useful to use the “5 Whys” method.

For example, if you are disappointed because you did not receive the promotion you expected, ask yourself “why” 5 times.

By doing so, you will go to the root of your disappointment. Very often you will realise that the reason was so subtle that you didn’t even know it.

Unveiling the true reason behind your disappointment is the first step in effectively combatting against it.

2.    Was there anything I could have done to prevent the disappointment?

When faced with disappointment, a very natural thing is to feel regret.

But not every situation is your fault. Consider these questions, were you in control of the circumstances?

You will realise that more often than not, you actually couldn’t control your circumstances.

You may have given your best in trying to land a particular job, but in the end you couldn’t control whether the company was going to give it to you or not.

In rare circumstances when it was actually your mistake that led to the disappointment, don’t worry. In this case, focus more on question 5.

The key goal of this question is to distinguish between disappointments that you had no control over, and those that you did.

3.    How will I likely perceive this disappointment in 5 years’ time?

When I faced a particular setback in my life, my friend told me a crucial statement I still remember until today, “It wouldn’t matter at all in a few years’ time.”

That allowed me to see things from a new perspective.

Ask yourself, how significant will this setback be in a few years’ time?

When faced with disappointment, it is very easy for you to be caught in “tunnel vision”. You only focus on how horrible the disappointment is. You only focus on what you had lost. You only focus on all the negative consequences the setback has caused.

This often causes you to miss the bigger picture.

Sometimes, one “no” may just be the key to unlocking the door to a greater “yes”. In the long run, that setback may not only be insignificant, but it may also propel you to greater heights.

4.    When I look back after 5 years, will that setback really have made me worse off?

I once came across this article about a girl who couldn’t feel pain. She has developed a rare disease called congenital insensitivity to pain.

If she falls on the ground, she will not cry as she can’t feel pain.

Is that necessarily a good thing?

Her mother’s response will shock you.

“Some people would say that’s a good thing. But no, it’s not,” says her mother. “Pain’s there for a reason. It lets your body know something’s wrong and it needs to be fixed. I’d give anything for her to feel pain.”

In the same way in life, don’t see disappointments as entirely negative.

Pain may actually be a good thing. Pain may open your eyes to certain aspects of your life that need growth.

Pain is what causes us to know when there is a problem in our lives.

Thomas Edison once said, “I have not failed. I’ve just found 10,000 ways that won’t work.”

I am sure you can recite a dozen more quotes about failure and disappointment.

You know very well that disappointment is often the foundation to success. It is time to truly believe it. Look at your disappointment from the lenses of the future.

Will your disappointment really not make you stronger?

5.    What can I learn from the disappointment?

Even though it has already been countless years ago, I still remember this incident while I was studying in school.

My class had done very badly for a Math test, I myself included. It was then when my teacher told us, “Remember the pain you are feeling now. Don’t just brush it off. Because by this pain will give you strength in future tests to come.”

Don’t just treat the pain you are feeling as your enemy. Remember it.

That is because with that pain you will remember the many lessons that came with the disappointment. And that will be your catalyst for growth into a more mature and wiser person.

Thus, I recommend that you reflect deeply on the lessons you can pick up from each disappointment you face.


Disappointments are painful. I know.

But they can be the greatest launching pads for your future successes.

Don’t look down on your disappointments. Start asking yourself those 5 questions today.

Nathanael Siew is the founder of the personal development website Wise Living Today, a website aimed at inspiring people to see the world through lenses of hope. With in-depth content and fresh insights, his articles empower readers to live a more meaningful and effective life. Get your FREE handbook + checklist on “The 9-Step Guide to Applying ANY Advice in your Life”!


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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