Maybe you were presented with a huge opportunity that could change your life, and you blew it.

Or maybe you did something that went against your moral code and you broke someone’s trust.

Or maybe you have been working really hard to excel, but always fall short.

Disappointments are the sad reality of living as imperfect beings in an imperfect world. At your lowest, it almost feels like the world is set up to be disappointing.

Hopes are dashed, dreams are crushed, plans are foiled and hearts are broken.

We take pride in our ability to learn, toil and perform. And yet one way or another, things don’t always work out the way we want them to.

Disappointment can be dangerous, especially if we present those disappointments to ourselves as evidence of why we’re not good enough.

This could lead to a state of learned helplessness, where we no longer care about improving and just give in to the idea of ‘What’s the point?’

I remember when I was in my teens, I felt disappointment almost on a daily basis.

Disappointment feels like being sick down in my stomach, as if I’d eaten something rotten. I didn’t understand why I was always so disappointed all the time.

Maybe I keep getting my hopes dashed, dreams crushed, plans foiled and heart broken.

I had a harder time coping with it then.

With disappointment comes shame – the feeling of not being worthy of anyone’s time. I avoided people because I believed they were disappointed in me as much as I was disappointed in myself.

And looking back, I’d get disappointed over the most trivial things.

I felt disappointed for not being brave enough to raise my hand in class.

I felt disappointed for getting a B when all my friends got A’s.

I felt disappointed in myself for not having the courage to ask for a girl’s number.

They seem trivial now but I guess for an ordinary teenager – they were matters of life and death.

But as I grew older and studied more about mindset and peak performance psychology, I realized that it was possible to even ‘turn off’ that instinctive habit of being disappointed all the time.

I did that, and as if like magic, life became undeniably simpler.

Not because I stopped feeling disappointed. No. It’s because I only got disappointed with the things that truly mattered.

And that made a world of difference.

My mind was clearer. I felt more at ease and free to just live. Consequently, I developed the courage to make mistakes and accept them as part of the journey of mastery.

That in turn made me way, way more successful.

I still do feel disappointment, but when I do, they’re about things that I truly cared about with every fibre of my being.

And I think that’s important.

So before we dive down into the dark, murky waters to try and pull out the weeds of disappointment, let’s zoom out and target the root of disappointment.

Why Do We Feel Disappointed?

Disappointment comes from only one thing: unmet expectations. 

When you feel disappointed with yourself, it shows that you had certain expectations for yourself, and you were unable to meet them.

Similarly when you feel disappointed with someone else, it shows that you had certain expectations for that person, and they were unable to meet them.

Being disappointed with someone else is another ball game altogether, so I won’t touch on that in this article.

So here’s where we break it down further.

The more expectations you have for yourself, the higher the chances of you feeling disappointed.

Also, the higher those expectations, the higher the chances of you feeling disappointed.

Simple, right?

So if you’re chronically disappointed in yourself, it could mean any of these two reasons:

1. You have too many expectations of yourself 

2. You’re expectations of yourself are too high

I don’t know about you, but I don’t enjoy feeling disappointed. Which is weird considering what I do.

Despite being a peak performance coach, I don’t expect myself to operate at peak performance all the time.

Because it’s a never-ending dash on a hamster wheel where you get burnt out chasing a prize that is impossible to achieve.

And yet in order to effectively be at peak performance – you MUST have a standard (re: expectation) of peak performance to rise up to and maintain.

So the question is: how do you continue to perform at a super-high level without getting barred down by constant disappointment?

Here are some suggestions that I’ve used myself:

Strategy #1: Recognize that most of your expectations are probably not your own.

First thing’s first: understand that our expectations are created solely in our mind.

Based on the references that we’ve collected in our past (e.g. our previous achievements, our abilities, our dreams, or what other people have achieved), we subconsciously set a bar for ourselves.

If you don’t sit down and take a hard look at the expectations you have unknowingly placed on yourself, you could be blind to the fact that those expectations are actually not your own.

It means you adopted them from somewhere. Your parents. Your friends. Your teachers. Your idols.

You got them from somewhere, but you’re pretending that they’re your own.

If you don’t check your expectations, it’s like you’re being a judge who is constantly putting yourself on trial and punishing yourself… for a crime you didn’t commit.

How is this a decent way to live?

I guess some people are okay with living by other people’s expectations.

But I see it like buying a suit: you only have a budget for ONE suit, but instead of going to have it custom-made to fit you, you decide to buy a cheap and inauthentic second-rate suit that someone else has worn.

Likewise, you only have ONE life to have it custom made. So you need to check it for authenticity!

Strategy #2: Allow yourself to be disappointed with only a few things… and let go of everything else.

Disappointment sucks.

Because it drains the life energy out of you like a leech.

Disappointment is inherently not a bad thing. We feel disappointed only because we CARE about things. We take certain things seriously.

But have you taken time to ask yourself what exactly should you be caring about?

Instead of trying to stop disappointment from happening when it happens (let me know if you found a way to do that), make a list of not more than 5 things that deeply matter to you.

Off the top of my head, this is my ‘Top 5 Things That Matter’ list:

1. Pursuing my purpose 

2. Living congruently with my core values

3. Being disciplined with my daily habits

4. Showing up at 100%

5. Being a leader of my community

From now on, I only allow myself to be disappointed with myself only if I fail to live up to these 5 things. They may sound like big ideals, but to me, they’re already how I’ve oriented my life.

So most of the time, I’m living up to these expectations.

For everything else – which I deem to be of less importance – I have learnt to embrace that if they don’t go my way, so be it.

I submitted a business proposal to a company and they decide to get someone else.

Should I be disappointed?

Maybe. But since it’s not in my Top 5 – shrug it off, move on.

I gave a humorous speech to an audience and my jokes fell flat.

Should I be disappointed?

Maybe. But since it’s not in my Top 5 – shrug it off, move on.

I ordered Crispy but I got Original instead.

Should I be disappointed?

Maybe. But since it’s not in my Top 5 – shrug it off, move on.

The lesson here is: without being deliberate and intentional about what to be disappointed about, we sometimes find ourselves being disappointed about everything.

So set yourself a new overriding expectation, and allow yourself to be disappointed for the things that truly matter.

Strategy #3: Lower your expectations.

Wow, groundbreaking isn’t it? But hear me out.

Did you know that tigers – the majestic yet deadly savage beasts we have come to know and love – only have a 5% success rate?

That means, 95% of the time when tigers hunt, they fail to make the kill.

And yet it doesn’t stop them from being one of the most impressive apex predators in the animal kingdom.

9 times out of 10, a tiger botches its attempt to kill its prey.

Do you think tigers ever get disappointed every time they miss?

You already know the answer to that.

Disappointment is inherent in human beings because we’re learning machines. Disappointment teaches us to course correct so that we can improve and make better decisions. 

Regardless of how high your expectations are of yourself, you will only rise to the level of your actual abilities.

And if you can only perform in accordance to what you can actually do, does it make sense for the tiger to want to grow wings and try to catch the eagle in the sky?

The beauty about lowering your expectations is that instead of being so obsessed with the result, you can now focus on the process and gain confidence by having small wins.

The power of small wins is the secret of peak performers. They get exceptional at what they do because they give themselves small, incremental challenges that stretch but are still within reach.

It’s hard to be disappointed when you’re winning, time and time again.

Give yourself that huge, unreasonable vision to strive for, but balance them out with small tasks to build momentum and seize those small wins.

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Disappointment, like most negative emotions, are only limiting when we allow them to be.

Know that there’s nothing wrong with you for being disappointed all the time, but there’s always a way to frame those disappointments and turn them into valuable opportunities.