Issue #5: Feeling like you fucked it all up
If you're not asking yourself if you screwed your life up every few years, are you really living?

“Did I fuck it all up?”
I’m 24, laying in bed, staring at the ceiling after uprooting my life from Vancouver to move to Toronto. Leaving my friends and my job to be closer to family and better long term opportunities - yet finding myself working instead at a Toronto location of the same job, in a more expensive apartment with less friends.
“Did I fuck it all up?”
I’m 29, curled up in the fetal position. I just quit a great paying job where I had been offered a promotion, so I could pack my bags and blow my entire savings account on travel, with no idea what I would do when I got back. I’m both sure I’m doing the right thing and wondering what the hell I’m doing all at the same time.
“Did I fuck it all up?”
I’m back from travel with no prospects and rent due. I had wanted to start fresh with a new vision for myself and new career to launch into. Instead I’m planning on slinking back into my old office and asking my boss to hire me back tomorrow, if I can ever fall asleep.
“Did I fuck it all up?”
I’m 30 and just quit my job to launch a new business, after going back post-travel for a victory lap (walk of shame?). Except after my first week at it, I am coming to the horrifying realization that I know nothing about business, am totally in over my head, have none of the right connections, and my skills from my previous job that I spent my 20s developing are useless and unappreciated in this new role. Odds of failure are too high, I decide not to get out of bed in the morning.
“Did I fuck it all up?”
I’m 33, staring at the pregnancy test, reminding myself that this was intentional, that it’s time to start a family, that my partner and I did this on purpose, that I’ll definitely be able to figure out how to be a mom and an entrepreneur at the same time, that I won’t lose myself, that I won’t be one of those moms, that this won’t slow me down, that I can do it all.
“Did I fuck it all up?”
I’m 34, sobbing in the bathroom with the fan on to drown the noise, overwhelmed by how consuming motherhood is, how much I don’t want to work anymore, how much of an identity crisis I’m in, how unprepared I was for everything, how much my body hurts, how little I recognize myself. My husband knocks on the door. “I’m fine, just give me a sec.”
“Did I fuck it all up?”
I’m 36, pregnant again, wandering around our 700 sq foot rental apartment wondering how we are going to jam a second kid in here, wondering if our savings will ever catch up to the cost of a down payment, wondering if I should have used that travel money to buy a condo before prices went insane, wondering if I’ll be able to afford living in the city much longer, if its worth continuing to rent or if we should move to the suburbs to a life we don’t really want, wondering if this next kid will be as awesome as our first kid, wondering if I’m disrupting the balance, wondering if everything is about to go to shit.
“Did I fuck it all up?”
I’m 38 and this time the question comes with an answer:
“Even if you did, you’ll figure it out.”
It’s true, the second kid is awesome and our family feels complete.
“Did I fuck it all up?
I’m 39 and it comes with another answer:
“It doesn’t really matter if you did, you can handle it.”
It’s got a point. We just put a down payment on a house in our neighbourhood. The mortgage is bigger than I can wrap my head around but I know we can make it work.
“Did I fuck it all up?”
I’m 41 and staring at the black mirror of my computer screen after logging off of the worst zoom call of my life. I just got fired.
I’m taking in my reflection. My 40s were supposed to be the time I moved past the fucked up moments, but here I am, staring into the abyss of the biggest moment of fuckery I’ve experienced yet.
But a wild thing happens. As the shock and anger of the moment wear off, I expect fear and insecurity to swoop in, but it doesn’t. I’m strangely serene. Confident. Calm even.
No doubt, this is a messed up moment in my life. But I’ve been in versions of this moment before. This is not the first time I’ve wondered if I’ve fucked it all up, and I draw strength from that. I’ve navigated through darkness and found my way back to light. I can handle this.
“Did I fuck it all up?”
I’m 42 now. Life is good. And the answer is, yes. Of course I fucked it all up. Many times. But I figured it out. And it turns out, that’s the part that matters.
Role Model of the Week
A weekly instalment where I highlight people I’m looking up to this week who are using the power they have to do cool, impactful, disruptive stuff to shift the status quo.
Last week, Canada lost in incredible leader. Murray Sinclair, an Anishinaabe senator and lawyer who led the Truth and Reconciliation Commission passed away at 73.
His work as the chair of the TRC was groundbreaking for helping Canadians come to terms with the history of the country, understand what colonialism means in practice and the horrors of the residential school system that separated children from their families and communities. As a white, non-indigenous settler born in Canada, the TRC report and the conversations and insights it spawned have opened my eyes to how much I wasn’t taught - and what I was taught - about Indigenous and Canadian history.
No process is perfect, but the TRC process - modelled after the same process used in South Africa post-apartheid - created space for conversations and understanding that until that point had been silenced or ignored. The work towards achieving reconciliation is long and ongoing, but the point is, it has begun thanks to the work of many people like Mr. Sinclair.
“We have to learn how to talk to, and about, each other, with greater respect than has been the case in the past. We may not achieve reconciliation within my lifetime, or within the lifetime of my children, but we will be able to achieve it if we all commit to working towards it properly. Part of that commitment is that every year [on September 30, TRC Day] we will stand up together and we will say never again. What we did in this country was wrong, and we will never allow that to happen again.”
Learn about all 94 of the recommendations for action from the Truth and Reconciliation Commission here.
You sound like the train of thought that runs through my head at 3am when I don't grab my phone to jot it down because I don't want the screen glare to wake my Mister. 45 and still recovering from my last 3 or 4 fuck-ups.
As someone who just turned 30 on one hand it kind of sucks that this question never stops being asked. But on other hand it’s a nice reminder that even if you do you will always figure it out.