On “failing at adulting”

old suitcase

I’m walking around an Ottawa suburb with my mom, getting some fresh air and exercise on a sunny late winter day when this thought crosses my mind.

“I hope to God I don’t run into anyone from high school.”

As soon as I think it my heart sinks and, I feel small and powerless and alone.

It’s a familiar feeling… but also an odd one.

Why would I dread seeing someone from high school? That was a millennium ago (or so it seems). High school sucked for sure but we’re all adults now.

Then it comes to me, the other thought that precipitated the sinking heart and feelings of being small, alone and powerless:

“I am a failure.”

Or more specifically “I’m failing at adulting.”  

It’s a thought that’s been bouncing around my mind for the past three years.

I don’t own a home, I don’t have children or a spouse, my business isn’t sustaining me, and my RRSPs wouldn’t get me through two years of living expenses.

I never really cared about any of these things until my late 40s. But, in retrospect, it’s not surprising they would surface now.

All of these represent a form of security and, although I’m not fully aware of it in this moment, I haven’t felt safe for a very long time.

But I don’t know that at this moment.

I only know that when my heart sinks and I feel small and powerless and alone on this walk with my mom on an otherwise beautiful day, I recognize the sensations and decide to get curious about them.

Because I am weeks away from moving to a different city, and these sensations – the heart-sinking and feeling small and powerless and alone – are exactly what I felt 25 years ago when I first moved from my home town.

At the time, high on Tony Robbin’s Awaken the Power Within, I’d decided to become a motivational speaker, quit my job, and told all the disbelievers in the office “Just watch me!”

Three months later I was broke, high on marijuana, and half-naked on a hotel bed during what I’d originally thought was a job interview for a “personal development speaking opportunity.”

I was mortified, ashamed, and unable to face myself.

I am a failure.

So, when the first opportunity to run away presented itself, I took it.

I packed my bags and moved to Toronto where no one would know me or know what a failure I was, and I could safely pack those feelings away.

But when feelings aren’t dealt with, they don’t go away. They just surface in other ways.

As I prepare to move to Prince Edward Island (this time pursuing a dream rather than running from myself) I’ve been sorting through my stuff.

Noticing these feelings, I realize there is one more box I need to go through before I go:  my good ‘ol suitcase of failures.

Because “failing at adulting” is just the latest verse in a sad song that’s been with me for longer than I can remember.


Later that day, I make myself some tea, take a deep breath, and get down to some long overdue unpacking.

“Where have I felt this way before?”

Turns out, I’ve been dragging the ol’ suitcase of failures around with me for most of my life, and is that thing ever stuffed!

There, underneath not investing in Toronto real estate, I find:

  • Launching a program that nobody signs up for – I am a failure
  • Spending two years of my life writing a book that doesn’t recoup the costs of publishing it – I am a failure.
  • Trying to get my high school boyfriend back by seducing him only to have it backfire and make me the laughingstock of the school – I am a failure
  • Learning that the middle school dance I organized is being canceled because of a flu outbreak – I am a failure.
  • Not getting long division, sucking at bowling, being the last picked for the soccer team, feeling like my parents love their new dog more than me – I am a failure

I unpack layer after layer – a greatest hits of my life’s disappointments – and as I do, I feel them all once again.  

Once I get my breath back, however, I’m struck by how many of these things were out of my control. I’m surprised I didn’t blame myself for John Lennon getting shot, the Challenger exploding, or 9/11. (Sorry guys, I should have tried harder.)


I know rationally that I’m not a failure.

I’ve written plays and a book and some pretty good songs, I sang with a band at the Winter Garden Theatre and danced in a weird opera at Burning Man where I was a gold-painted sun snake.

I helped change the corporate culture of a massive organization. I did a speech that’s had over a million views on Facebook. I have a list of accomplishments 60 pages long, and dozens of emails stored with people thanking me for something I did for them.

If creative output or inspiring others was the standard measure of success in our world, I would be killing it!

I can’t remember anyone ever telling me I was a failure.

In fact, most people around me tell me they believe in me and think I am capable of great things.

They’ve told me so my whole life. Yet, instead of fully internalizing this and going with it, I’ve always had this feeling of not measuring up.

My inner cheerleader is strong but there are days when she is no match for my inner bully.

I am failure.

I can’t remember where this thought first came to be, but I do know this:

I was bullied and sexually assaulted as a child.

 I also felt like I needed to be super good to get my parent’s love and affection. It didn’t feel safe to show weakness and it didn’t feel safe to be bad at things. As a child, I didn’t have the tools to give myself the compassion I needed and for whatever reason, I didn’t go to the adults in my life for support.

Instead, I internalized difficult events. Blamed my own ineptitude and felt worthless and alone.

And then a part of me developed to prove those feelings – and the people who hurt me – wrong.  

I am a failure, it whispers. 

And when it does, I get into action. I set big goals and work myself to the bone to make them happen. And then, when they do happen, I celebrate for a day or two until that part of me decides to search for the failings in the achievement and I get down on myself once again.

This is the pathology of the overachiever, the perfectionist, and the people pleaser. And this is a lose-lose situation. Because when a part of you feels, despite all outward accomplishments, you aren’t good enough, it’s going to look for evidence that it’s right.

It’s going to blame you and make you feel guilty for things are out of your control.  It’s going to encourage you to set ridiculously high expectations of yourself in ridiculously short-time frames.

And when you do succeed by stepping out of your comfort zone and learning things you would have never known any other way, and even impressing the fuck out of others, it’s going to tell you to focus on what didn’t happen because…

You are a failure.

It does all these things, not because it’s evil incarnate or the most abusive mofo you’ll ever meet (although at times it will feel like that).  It does all these things to keep you going because it sincerely believes that if it didn’t, you would die!

It believes without it protecting you and motivating you to keep achieving, you will not get the attention you need and will therefor cease to exist.

Because this part of you? It thinks you are still two or seven or twelve or fourteen or however old you were when it first developed inside of you.

That is a lot of responsibility for a little kid.

That is a lot of responsibility for a full-grown adult and my ol’ suitcase of failures can old hold so much.

The leather is cracked. Its zippers are bursting at the seams and try as my inner critic might, there is simply no room for one more ounce of self-condemnation in it.

“Failing at adulting” was apparently one failure too many.

I’m good with that because this is one piece of baggage that I don’t want to take with me on the next leg of the journey.

That said, I can’t just pretend to leave it here either because to do so would be to ignore the parts of me that need my attention – parts of me that need my compassion, an apology for ignoring them all these years, and my love.

And so today, a month and a half after that late winter walk with my mother, that is what I am doing.



And recognizing that although some of the things I wanted to happen in the past never came to pass those “failures” aren’t real. They are merely interpretations of events.

And those feelings  – of being small, of being powerless, of being alone – don’t mean that I am that way.  They are merely echoes of past me signalling to present me that I need to give myself some love.

Which works because I am human.

And like all humans, I come with not only parts that get down on me sometimes, I come with a part that doesn’t care whether I win or I lose: a part that only wants to love, a part that is love.

And it’s this part that is holding my hand and whispering today:

I am here. I am me.

I am enough.

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