the gift of failure – and how to unwrap it

We grow up wondering if we’re ever going to feel “it.”

You know, maybe if we’re lucky, we’ll stumble upon that illusive feeling. What feeling do I speak of exactly? The feeling of inner worthiness. The one we refer to as being “good enough.”

In pursuit of this feeling without a set criteria, we create a false impression of ourselves. It begins in childhood when if we always feel like we’re coming up as inadequate then striving to be “good enough” becomes a motivator. In essence it’s because you unconsciously believe in a mythical place called “a happy ending” – that it’s somehow the pain on a painful journey that gets you where you really want to be.

(But that’s kind of a gross misinterpretation by ego that I’ll talk about another time.)

You know you’re striving for “good enough” as a “happy ending” when the rewards of your so-called accomplishments are empty, meaningless or meagre. Regardless of how impressive you are regarded as. They can’t quite satisfy deeply nor for very long. Compliments, higher pay, more vacation time, being liked or approved of … intrinsic satisfaction does not exist in spite of extrinsic rewards and validation.

It’s not enough because if you accept that you’re enough, you wonder how you’ll do better next time. “What will motivate me?” is what you wonder if not for the belief that you’re not enough. And the answer right now is: You have a point.

We find ourselves actually believing that feeling inadequate and striving for enoughness is what makes people good people – humble, kind, admired, generous, successful, loved, approved of. So to keep on this nobly intended path you’re always trying to be good by thinking that you’re not.

So how did this happen? Well, here’s me and my story. You may want to consider penning down your own:

When I was a girl of about 10 I’d bring home almost all A’s on my report card. But all the attention was given to the ‘failure’ of having received my one B(lemish) in math. No matter how hard I tried. And while a ‘B’ is far from failing, I was lured by the possibility that I had a real shot at being good enough if only I fixed this one thing. It would ‘happen for me’ if only I brought home an “unblemished” report card. I didn’t question that this is how I could achieve “good enough.”

So the miraculous happened, but I have no idea how. Perhaps it was just my turn or there was a quota for how many A’s they could give out in math or maybe it was that math suddenly for whatever reason started to feel a little bit easier because I liked the teacher more. Who can really say?

All that is to say that how I ended up with an A in math in addition to all of my other subjects was a mystery to me on the last day of grade 6 at the age of 12.

I was looking forward to congratulations, acknowledgement, gratitude, being asked what I wanted for dinner to celebrate. I had it in my head that I had finally become good enough and that someone would validate that belief so that it could be true. Then I could rid myself of this terrible feeling that ruled everything about how I lived. Even at 12.

But I was raised by people who never thought of themselves as good enough and that “good” was something you needed to trick and train and coerce yourself into being. So all they could pass on was what they thought motivated them and what they thought would motivate me.

I found out that I was still not enough that day. Except I still wanted to be enough. And I felt like I still had a chance. I still had my whole life ahead of me. After. All.

Turns out that I could maybe be good enough if I had neater hair, a room that was tidy all the time, completed chores without being asked or reminded, and a better memory (about the chores).

Failure seemed like it was the only thing I could achieve even when I was achieving. And so it became my goal to always think of and see myself as coming up short no matter the outcome so that I would always be motivated to be perfect and successful as a human being.

So what happens when you grow up learning that striving to be good enough is better then feeling good enough?

Well, it’s kind of ironic: You’re living in a way that has you actually believing that you’re eluding the feeling of inadequacy – at least in appearances. No one would ever guess that you feel like a failure based on your education, your job title, your salary, your fashion sense, your significant other, you fb status – the PR on your life looks great. But you know that it’s a lot of work to keep up looks that don’t make you feel how you want to feel.

Truth is you’d probably snap at anyone that suggested that maybe you didn’t seem happy under your happy exterior.

(Go on, just imagine your reaction to that suggestion to see if anything defensive happens within.)

What we don’t realize is the gift intended should we dare to really feel (sit with + be with) this feeling of inadequacy. We live erroneously expecting ourselves to goes through life without encountering this dragon rather than surrendering to learning to tame it. Instead our culture tries to eradicate or run from it until death. If we sat with him, invited him for a cup of tea, asked him to inform us – he would cease to be formless and scary and overwhelming because he’d guide you by teaching you compassion and how to make meaning from the meaningless.

You don’t see (just yet) that feeling like a failure doesn’t mean that you are actually willing to fail.

Only real failure can give you what the phoenix rising from the ashes has: A new life free from the past rather than building a life out of the past.

Let me explain with a story: I once met with a group of high school girls – grades 9 – 12 in Kuala Lumpur. Daughters of Anglophone expatriates and wealthy local families. Their guidance counselor asked if I would visit with them and talk to them unrelated to the reason for my business there.

Turns out that he was actually very worried because he would talk to these young women about what they “really wanted” and then see them go off in a direction that seemed at odds with and much below their aspirations. He was at a loss as to why and wanted to do something about it. I wasn’t supposed to lecture them or to sway them in any way. We were just going to talk about it. It was the elephant in the room.

So as they huddled around me on the carpeted floor of an air conditioned classroom protected from the stifling heat and humidity outside, I asked them something that I myself needed to seriously ponder even in my highly envied job:

Are you a success if you succeed in getting what you know you can get if you only go after what you know you can get?

They said yes. And of course no one could disagree with that. That’s what mattered. That’s what they were judged against – what they got – not what they tried for and didn’t get.

I wondered where this conversation would go. I mean, they weren’t wrong to see their lives as they did and pursue what they did accordingly.

And then this next set of questions and reflections came to me as I spoke in an unplanned way:

What about the thing that you really, really want that you’re not willing to fail at? You know, the secret thing or the thing your parents say you can do after you get “a real job”? What happens to that dream, wish, aspiration? Where does it go? What happens to you in the process of trying to dismiss it or get everything else done first before you can go near it?

What was funny, that I didn’t expect, was that they knew exactly what I was talking about.

Now we were having a real conversation. About fear. About rejection. About disappointment. And in hearing their thoughtful, un-socialized, completely authentic answers they connected me to the part of me that was just like them. True I was older than them, but no matter how old you are there’s still time to waste isn’t there?

Especially when you think your life has already been written or you’ve gone too far down a certain path – you still have your whole life ahead of you.

Your whole life is what you have yet to live. Tomorrow after all is still …

Undecided. Unwritten. Unlived. Not even yet acquired.

And you get to decide how making money + paying your bills + acquiring things feel – playful and engaging or debilitating and painful.

A fairy tale isn’t really about the happy ending anyway … it’s about the story.

So, you knew you’d be asked: What is that “thing” you most want to succeed at that you know you need to be willing to fail at?

What’s mine? You’re here reading this. Aren’t you?
I am also willing to fail at being a furry mom and a wife.

And if you ask me, that’s the secret to living a life that is both genuine + free.

make. believe. for real.
Where you fuel, re-tool and attune your imagination. Get your soul to work (on purpose). Ruthless compassion. Fierce gentleness. Sassy wisdom. And oodles of insight.