The Wisdom of Disappointment

“We must surrender our hopes and expectations, as well as our fears, and march directly into disappointment, work with disappointment, go into it, and make it our way of life, which is a very hard thing to do.” - Chögyam Trungpa

If you’re like most humans, you’ve done everything possible to avoid feeling disappointment, perhaps even built your entire life around experiencing it as little as possible.

Perhaps you do one of two things: 

You keep your life small which means avoiding having hopes, dreams or expectations: 

I’m fine like this. I just want a simple life. I don’t want to want anything because then I’ll never be disappointed. It doesn’t really matter to me anyway:

If I don’t open my heart to anyone, then I won’t be hurt. 

If I don’t have ambition, then I never have to put myself out there and risk being disappointed.

As researcher and writer Brené Brown says, this is about choosing to live disappointed in a low grade kind of way rather than risk feeling disappointed in a bigger way at certain moments in life. 

The second possibility looks very different: Striving for perfection, in an effort to avoid failure and disappointment: If I do everything right, I’ll never make a ‘wrong’ decision so I’ll never have to feel disappointment.

Avoiding Disappointment

How does it make sense that we might have learned to protect ourselves from disappointment in these ways (and others)? Chances are, as a child, we experienced disappointment as extremely painful:

x Perhaps we were criticised by care givers or teachers when we did something wrong, and the feeling of being a disappointment felt unbearable. 

x Perhaps a parent’s disappointment in us was interpreted as there’s something wrong with me, I am not worthy, I will be abandoned - which felt unbearable.

x Perhaps our parents said something like: I’m not angry at you, I’m just disappointed and that cold feeling was even worse than anger.

x Perhaps we felt our parents’ disappointment in their own lives, not necessarily through words but through what we picked up on.

x Or perhaps we were disappointed by parents who couldn’t show up for us in the ways we needed them to when we were children.  

Even if experienced only once, it makes sense that we would come to the (unconscious) conclusion: It’s too painful to feel disappointed so I must avoid it in any way I can.

And so we built our internal villages to avoid ever feeling this ‘dangerous’ emotion again, even at a very high cost.

Yet what we resist, persists. Again, Brené Brown: 

“When we deny our stories and disengage from tough emotions, they don’t go away; instead, they own us, they define us.”

Being Willing to Feel Disappointed

Instead of being unconsciously ‘defined’ by avoiding disappointment, I want to suggest something that may seem counterintuitive: 

While never easy to feel, disappointment can actually be a very wise guide.

The etymology of the word disappointment comes from the old French desapointer: dis- reverse, opposite of + appointer - to appoint, which is a form of choosing. So literally the old French desapointer means to un-appoint or as I interpret it, to un-choose.

So I see the role of Disappointment Villager in our internal villages as simply telling us that something in our current reality is not working for us and that we may need to un-choose in some way. 

This un-choosing does not mean having to completely give up or let go. It isn’t an all or nothing thing. What it might be signalling is that something in our current reality has not worked out, and this could be an expectation, a belief, a dream, an ideal, a part of ourselves or a way of doing things.

Disappointment says nothing about our value as a human. In fact, if we are open to life, and fully experiencing the messiness of being human, if we are putting ourselves out there and opening our hearts, then disappointment is inevitable and unavoidable because we can’t control everything.

The Gap

Imagine walking along a path. At some point you look around and realise: This isn’t where I want to be. Something isn’t right.

There’s a gap between where you are and where you want to be, or had hoped to be.

Hello, Reality vs Expectation.

Allowing disappointment can look like: 

x Stop. Allow yourself to feel disappointed without resistance. After all, it is not your enemy, simply a messenger with some important information. Hello, Disappointment.

x Take stock of the current situation with curiosity (not judgement). What is this feeling telling me?

x Re-calculate: Un-choose what no longer works and re-choose what feels more aligned.

So disappointment steps in and helps us admit the current reality is not working in some way. It allows us to be honest about our reality IF we can avoid going into blame or wallowing, which can actually be a way of avoiding the more difficult task of taking responsibility.

It helps us take stock of the situation: What isn’t working for me here? What part of this am I disappointed about?

It helps us re-connect to values and re-calculate how to keep moving towards them, like a GPS: What does this tell me about what really matters to me? How else can I keep moving towards these values, perhaps in a different, more realistic way? Do I need to adjust my expectations? Do I need better boundaries or self-care? Do I need to admit that the current reality does not meet my needs and adapt in some way? Do I need to walk away?

Disappointment allows us to land in reality with a thump: This is where you are. Stop. Take stock. Re-evaluate.


Afterall, as Psychologist Les Greenberg says: "You can't leave a place until you've arrived."

By doing this, disappointment helps us re-shape reality in a way that can be helpful, it helps us figure out where we go next.

For example, disappointment may tell me: There is a gap between my desire for intimacy and connection and my actual relationship. This does not mean getting rid of my values around intimacy and connection. It does not even necessarily mean letting go of the relationship. When I can allow myself to sit with disappointment, I find that on the other side are creative solutions, new possibilities, new paths that I could not see before listening to disappointment.

So I might decide to do something different to create more opportunities for intimacy. I might talk to my partner. I might decide to look for this more outside the relationship. I might work on my own capacity for intimacy. I might question whether my expectations are realistic.

Disappointment is not the end of the path. It’s simply a necessary stop that can help us take stock, un-choose what doesn’t work and re-choose what feels more aligned. 

By being willing to feel disappointment instead of trying so hard to avoid it, we dare more, risk more, and open our hearts more - knowing that if things don’t work out, it’s OK.

When we can see disappointment as just information that can help us to un-choose and re-choose, we no longer need to build our lives in an attempt to avoid it.

A reality check

I think we all have unrealistic expectations of life, of ourselves and of other people, and this gap between our expectations and the reality of life and what it means to be a messy human can lead to a lot of unnecessary suffering.

David Richo outlines these five core challenges that we all face yet are often in denial of:

Everything changes and ends.

Things do not always go according to plan.

Life is not always fair.

Pain is part of life.

People are not loving and loyal all the time.

These are the core challenges that we all face. But too often we live in denial of these facts. We behave as if somehow these givens aren’t always in effect, or not applicable to all of us. But when we oppose these five basic truths we resist reality, and life then becomes an endless series of disappointments, frustrations, and sorrows.” - David Richo, The Five Things We Cannot Change: And the Happiness We Find by Embracing Them