What I’ve Learned about Feeling like a Failure

A short story about a conversation with a friend that invited me to reflect back on my career and why I felt like a failure.

Amanda Baker
4 min readMar 26, 2021


I was speaking to a good friend a little while back, reflecting on the past year in lockdown. She shared her frustration and sadness around her career and mentioned feeling like a failure because she made the decision to walk away from a job that didn’t feel right for her anymore.

She asked me how I’ve overcome this feeling in the past. And that got me thinking.

I’ve shared my friend’s feelings not so long ago. When I made the decision to make a move like hers. It’s hard. It’s heavy and a bit lonely too. Because suddenly, it hits you that you’re about to move into a space with no ground under your feet. Who you are and how you introduce yourself and everything you were a part of making real is dead. Yep. Dead.

I think failure is made out to be this grumpy, dark and lonely thing that shows up when shit hits the fan. And yeah, it does. But for my friend, shit didn’t hit the fan and blow up, shit just changed. She changed. What she wanted changed. She became more aware of her feelings and started listening to herself and that’s what led her to leave her job. And that feeling of failure still showed up. Why? I think there are a few reasons why. And I can summarise it in one word. Identity.

The work we do, our title, our conscious contribution to the world shapes our identity. It helps us communicate who we are and what we do to people. It helps us connect with people. We can’t live without our identity. It’s how we belong in the world. As Brene Brown puts it: “Belonging is when others want you.” We all want to be wanted.

For example, a year ago I would introduce myself as Amanda, co-founder of Flamingo Punk. About 5 years before that, I was Amanda, Founder of Fashionably Skint. These roles, duties, ventures, missions, purposes were a part of me. They made me ME in that chapter of my life. When things didn’t work out the way I’d planned, yep, you guessed it, I felt like a failure. It was a scary and shaky space where I felt lost and a bit lonely. Who am I now? Just being Amanda didn’t feel enough.

My identity had suddenly vanished. And that’s why I felt like a failure. But it never lasts long, just a few blank pages or so. Because that failure feeling always disappears when the next calling turns up, and it always will. The space we move into after our lives suddenly shake up is an incredible space to be in. It’s like the universe has invited you (again) to write down what you want, what you want to be, do and see. How you want to show up. How you want to be remembered. What you care about. What you want to be known for — all of that good stuff.

We get the power back. The blank pages are the fucking power. The blank pages represent the not knowing bit. As scary as it sounds, fuck me, it’s so freeing you wouldn’t believe. It’s a spiritual awakening. A chance to feel it all for a bit. And sit with it. I mean, how often do we get the chance to do that when we’re in the thick of living?

Pema Codron, Buddist Author of, When Things Fall Apart, talks about it like this:

“Things falling apart is a kind of testing and also a kind of healing. We think that the point is to pass the test or to overcome the problem, but the truth is that things don’t really get solved. They come together and they fall apart. Then they come together again and fall apart again. It’s just like that. The healing comes from letting there be room for all of this to happen: room for grief, for relief, for misery, for joy. When we think that something is going to bring us pleasure, we don’t know what’s really going to happen. When we think something is going to give us misery, we don’t know. Letting there be room for not knowing is the most important thing of all. We try to do what we think is going to help. But we don’t know. We never know if we’re going to fall flat or sit up tall. When there’s a big disappointment, we don’t know if that’s the end of the story. It may be just the beginning of a great adventure.

My advice to my incredible friend was this:

Think of your life like a story. Like a book. You have all these chapters filled with people, emotions, situations, stuff that happens that makes you who you are, at that moment. What was the message of your 2020 story? And what is the title of your 2021 story? Thinking about life in this way gives us the invitation to ask those deep and simple questions like, ‘what do I want?’ ‘what feels good’ ‘what makes me happy right now?’. And get creative with our lives. Next chapter. New adventure.

I think, the reason why we feel like we’re a failure from time to time is because we forget that we are always in transition. We are always changing.

Ram Das says it perfectly… “Make friends with change.”

(Deep breath.) I love that. Let’s do that.

Thank you for being here. I hope you enjoyed reading this piece.

Here’s a little bit about me…

I’m the co-founder of Make Us Care — a strategic creative partner for businesses doing good in the world. I work closely with founders, leaders and marketing teams to build brands people care about. My magic sauce is a communications framework I created called the 5 Stories.



Amanda Baker

Founder & creator of 5 Stories, a methodology I use to help businesses tell stories that connect with people. I write about storytelling and entrepreneurship 💫