Making Friends With My Disappointment

Jun 15, 2026 | Coaching, Facilitation, Leadership

(My first time being managed that is!)

I’ve had a couple of personal disappointments recently including not getting a facilitation consultancy that I was hoping for. And this was on the tails of a conversation with someone who was asking how they could stretch themselves to go for a challenging new opportunity without being disappointed. The two experiences felt like an exploration into that icky feeling that many  of us actively try avoid.

Even thinking about what disappointment feels like feels icky (I don’t have a better descriptor than icky at the moment). Putting words to it is hard. I feel like the blood drains out of me, leaving me feeling shame and embarrassment. It makes me want to go and sit under a blanket, or comfort eat ice cream, or run away to escape the discomfort it brings. It feels like an objective truth. “I am a disappointment”. And I will do anything to escape that feeling.

This time though, maybe thanks to my previous conversation, I decided to lean into it and sit in the ickiness. The stickiness. And ask this feeling what it wanted me to really know. Rather than trying to snap out of it, I stuck with it. And got curious. And, like with most of the monsters that sit under our beds, when I pulled it out to look at it, it wasn’t at all what I was expecting. Nor did it tell me what I was expecting to hear. These are some of the things ‘she’ said:

“Anna, you know that all of your feelings are trying to protect you, or help you. Even the ones that feel horrible – what do you think I want you to know? Part of me is trying to help you notice that what ever just happened or didn’t happen, was something that is important to you and you care about. Pay attention to what the essence of that is. You want to avoid feeling this way – so maybe this inspires you to try harder, or differently or get more creative. But please, oh please, don’t think that this is an invitation to make yourself smaller. If you aren’t ever experiencing me, it means you are playing it too safe. All the time. If you are never disappointed, it means that you have never tested beyond your limits. Which probably means that you are playing always in your comfort zone. We know that muscle strength grows when we push just beyond our comfort zone, allowing the muscles to micro tear, and then heal. So the next time we can push harder, dream bigger. I’m not suggesting you set yourself up for disappointment after disappointment after disappointment. That would imply you aren’t taking the lessons from the experience and putting them to practice. But a life without disappointment might feel a little bland to you

As you can see my inner disappointment persona had quite a bit to say – and after she’d said it I felt lighter. And the actually thing I didn’t get felt way less important.

My coaching invitation is to invite you to pick an emotion that you don’t like to experience, and next time it shows up, invite it into conversation and see what it wants to tell you – you might learn something interesting!

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