Category Archives: Failure

On Failure

Failure and I have never had a good relationship. I was always that kid who could pick things up with relative ease, I was a star student and teacher’s pet throughout high school and did well in my university classes too. I won medals in my extra-curriculars and my bosses’ regard during summer jobs. I always thought that if I followed the rules, laid out a good path for myself and worked hard, then things would fall into place. But that feels like a very naïve perception of things now.

I understand that failure is a natural part of any learning process. I understand that failure allows people to evolve and become stronger. I even understand that it gives people character, experience and intellect. Yet despite understanding these things in theory, the fear of failure still stops me from living the exact way I want to. It means that I can’t stand being a beginner. Rock climbing, yoga, guitar –things I discovered I loved yet have completely stopped practicing because they involve too much public failure as a beginner. Even as I write this, I worry I’ll fail at getting my point across or at making this article compelling and relatable.

Lately, failure is mostly associated with the job hunt. I finished my Masters 6 months ago and I am still waiting tables. I’ve been told that’s a normal amount of time, and that in this economy it’s actually not even that long. But every day, my various visions of the future get a little bit fuzzier. That image of me managing a team of policy advisors then driving home in my electric car to my beautifully decorated home gets blurry when tips from work are bad that week and I worry about the electricity bill. The picture I have of working in the field, collecting data on endangered species in exotic locations fades with each rejection email. The constant feeling of failure does nothing to motivate me to keep sending more job applications into the void of HR email accounts. Each rejection letter ends up making me feel more entitled, like somehow because I’ve gone through this, I deserve the job more.

I’m aware I’m not the first recent graduate to feel this way. And I’m trying to take these daily feelings of failure in stride by making time for friends and being out in nature. But the sinking feeling is inevitable when I sit down in front of a miserably formatted Word document job application once again. I apply to most jobs knowing I’ll never get an email back, let alone a positive response. Every pep talk from well-meaning employed friends or family feels like a repetitive reprimand despite it coming from a place of genuine kindness and concern.

I’ve been thinking more and more that I want to get creative and approach the entire job process differently, as so many of my peers are doing. Young people are taking the cards dealt to them and turning their traditionally losing hand into something wonderful by starting creative businesses, working remotely in budding industries or foregoing the notion of a typically defined career entirely. But again the fear of failure stops me in my tracks, despite my extreme admiration for friends who have taken the leap.

For now, I’ll keep searching and enjoying the little things. No doubt that this idea of creating my own career path will keep brewing in my mind the whole time. Maybe I’ll try and think back to the days when I barely had a concept of failure. I’ll try to incorporate some of that boldness into my future career goals. After all, back when I was a straight A elementary school student, free from the fear of failure, I won our school’s Valentine’s Day lip syncing contest five years in a row.

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On running (and the downfall of pride)

It is a dreary, wet, and cold October morning, and there is paint dripping down my face. The helmet atop my head is two sizes too small, and has my skull locked in a vice grip. The small camcorder haphazardly taped to the top of that large child’s helmet is now getting wet, and so I’m not even sure that this little experiment of mine will work. Oh, and we can’t find the starting line. Well, we can see it, but getting there is another matter.

Confused yet? Fair. If your first thought upon reading the above was not “the start of Tyler’s short lived and disappointing running career” I could probably forgive your error. But that’s just what it is. Every word of it, the truth.

It was a Sunday and it was early. The helmet was on my head because I needed a way to mount the camera, and the camera was atop the helmet because I had the bright idea to film my 5k race, in the Scotiabank Toronto Waterfront Marathon. Both of those things were the case because I was, at the time, interning at EWB, and because interns are keeners, I was filming my race to make a video for EWB’s Run to End Poverty. Oh, and the paint…orange was EWB’s colour. So, naturally, I painted the helmet orange. Apparently, however, when you glob on large amounts of paint the night before, it takes a somewhat long amount of time to dry. This hadn’t happened, and now the rain.

But back to the race. After stumbling around confused, we found the start, and the race began. I had always been generally athletic, but this was my first official race. I hadn’t really trained, hadn’t really slept the night before, and I really had to pee. Did I mention the rain?

All this aside, I loved it. The race was a blast. I never really had opportunity to realize it before, but in those short 5K I saw just how into the competition I could get. The thrill of passing people drew me on, faster and faster, and in just under 24 minutes, it was over.

For a while after the race, that was that. It was fun, my video turned out surprisingly well, my shrunken head returned to normal size, I hung my race bib on the wall, and went back to everyday life.

But as the New Year rolled around I found myself thinking about running more and more, and began to play with the idea of training for the full marathon in next October’s STWM.

Now, on a few occasions during my young adult life, there were times when I ran consistently for general health and wellbeing. But I never considered myself “a runner” – I never formed part of my identity around the activity. That changed in March of 2013, when – with the help of my Uncle Bryan and Elevation Personal Coaching – I officially began to train for the elusive 42k.

It didn’t take long before I was hooked. The thrill of pushing your body beyond what you thought previously possible, and the ability to actually see your progress kept me coming back for more. Over time, running became a bigger and bigger part of my life.

I was building my schedule around fitting in runs, I was eating better, and more, to match my level of exercise. Hell, I had even bought protein powder.

Pretty soon, I started to eagerly anticipate Sunday mornings, when my world became one of a still rising sun, a cool crispness in the breeze, carbohydrate gels and logged kms, in my weekly long distance runs.

I will never forget my first attempt at 15k – the first time I experienced “the runners high”. As I rounded the last corner in my route, coming into a 3 block straightaway to my apartment, I was on top of the world. I didn’t feel tired, or sore, or worn out. On the contrary, it felt like I could’ve kept going for another 15K.

Part of my enjoyment from running came from – and excuse me while I ditch humility for a second – I was fucking good at it. I was managing the upper distances without too much trouble, and more importantly, to me, I was fast. My uncle and coach had dubbed me “Flash” and I became obsessed with the idea of speed.

It eluded me at the time, but looking back now I can’t help but think that running became a proxy for other things in my life. After some rough personal-life times and the stress of work-life times, as well as a general late winter/early spring malaise, it felt good to be doing something I enjoyed, and doing it well. In part, I think, because it was real and tangible. Unlike my work, which was ambiguous, short term and at times, hazy – where success was unclear and in an environment of brilliant people, often overshadowed – running was real. My times were definite and quantifiable; in the immortal words of Shakira: “Ooh, my Garmin don’t lie.”

I had something I was succeeding at, and was proud of it.

But my uncle’s nickname of “Flash” was not – I think – just a reflection of my finish times. It hinted at my tendency to be young and dumb and overzealous. Things were going great, I was feeling good, and so when Bryan would say things like “Keep the pace above 4:45” or, “Take it easy on this one,” my brash brain would, at times, respond, “but whyyyy?!” I could do it so much quicker. And I sometimes did. But with a body as complex and susceptible to injury as the one we’ve got, speed isn’t everything. And pride will be your downfall.

It was a gorgeous Sunday morning. I was in cottage country with colleagues. I’d avoided drinking the day before, in preparation for what was to come: an empty country road, a backpack full of water, and 21K. Now, I had done this distance before – this was a revisiting. A step back. A refresh. My instructions were to do it at a reasonable rate; just take it easy and enjoy it. But my pride had other ideas.

I wanted to crush it. I wanted to push myself and see just what was possible, and what I could do if I went all out. And so I did. I pushed and I pulled from deep within and in less than an hour and a half later, I was done. I didn’t tell Bryan. I think I knew that he would be less than pleased. But I did it. It was possible. And what’s a little extra effort now and again, anyway? Well…

I was sore. Not unreasonably sore, I convinced myself. Just sore. Looking back now, this was likely the beginning of the end. For it was a week or two later, 23K-ish out on the Toronto Waterfront that my right knee gave out. I’m not even really sure what happened, it just kind of…hurt. A lot. And I stumbled. And then running was impossible. And then walking was hard. But there I was, 20K from home, without money or a way back. So I walked. Slowly, and gingerly; in pain, both body and pride.

It was awful, long and slow, but I made it home and reported the news to my uncle. A few weeks off was the prescribed solution, along with a lot of ice and elevation. Despite my best attempts, however, a few more ups and downs made it clear that I wouldn’t be ready to run in October.

It was now my turn to be crushed. To have trained so hard and for so long, and now…this. Watching from the sidelines on race day pained me in a deeply physical and emotional way. All the success, excitement and hope for what was possible was gone. In its place, a feeling of stupidity and hopelessness about running.

It took a while, but I eventually got over myself, and life moved on. I resolved to come back better and, more importantly, smarter, next year. But when next year rolled around the universe had other plans. Despite months of rest, my knees just never felt the same, and life events threw curveballs in many attempts to get training back on track. After a number of these false starts and several long winded Facebook explanations to my uncle, I went silent. I stopped running and stopped communicating.

I had given up, and I retreated.

I was scared about the state of my knees and their ability to carry me on the wind again. Was embarrassed to have done this to myself. And, I felt like I was letting Bryan down. It was hard enough to admit all of this to myself, and so I never tried to convey it to my uncle. For a long time, I beat myself up about it, until eventually I pushed it out of mind and tried to focus on other things – work, writing, photography.

Recently, however, I went for a run. Not a timed, training run. Just a run. It wasn’t very far and it wasn’t very fast and I didn’t have carbohydrate gels and I didn’t post the results to my online training diary. And it was…nice. I was relaxed and without pressure. There was no expectation, no target to hit and no fear of what was next or whether I’d be able to run again in the future. Just me and the trail. For so long, running had been a means to an end – I was training for a marathon. There was an end goal in mind and running was (quite literally) the vehicle that would get me there, across the finish line at the 42K mark. Now, for the first time in a long time, running was an end in itself. It was a nice change, and one that sparked a realization about my relationship to a lot of what I do in life. It was in this moment that I was reminded, in particular, about this crazy hectic panic filled transition between “now” and “adult life.”

Because I have very much been treating that transition as a means to an end. Work has been the thing, the experience, and the connections that will lead me into whatever my “place” is. I’ve seen work as the path leading me to my real purpose – the big shiny pot of gold at the end of the terrifying rainbow of young adulthood. In approaching it this way, it has been needlessly stressful. Every slight hiccup, diversion or stumble along the path has been so much more than that, because of how it was detracting from my pursuit of “the end.” I have consistently failed to see these things for what they are: a challenge, a learning opportunity, a potential for skill development. That’s not to say that these moments wouldn’t still be stressful through this different mindset, but I’d be able to take them as they were, instead of as what they could be.

So maybe, if I can get over myself for long enough, work too can become an end in itself. I can take pride in the everyday small projects and wins. And maybe, I can start to find enjoyment in it again.

For now I’ll keep running. Not far, or fast. And without my Garmin. I’ve accepted that there probably isn’t a marathon in my near future. But someday. And when that time does come, I’ll be smarter. And I’ll listen to my coach.

(ps sorry Bryan)

Until next time.

Ambiguously yours,


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on learning about, and from, failure

The other day I caught myself saying, “when I left my job” instead of “when I was laid off”. This week marks the one year anniversary of that event, and it’s remarkable how much my narrative about it has changed.

For a long time shame held me back from candidly talking about my unemployment; a shame born out of a fear that I had somehow failed. After all of those long hours, sleepless nights, heart and soul conversations about money and change and potential and better worlds, why was I let go? It must have been because I was too critical. I didn’t deliver. I wasn’t good enough. For a long time I waded through neck deep amounts of internalized failure shit, and I thought awful things about what it meant to be laid off (but really what it meant to be a person).

In January I started working on a conference about failure, in particular how to build a productive relationship with failure. I took on the social media role and spent near every day reading other people’s 140 character insights on what it meant to fail forward, scoured blogs for content, and tried to  sell people on why they should attend a day long event on failure. While I in no way planned for this to help me out of my internal failure funk, it did, because there is something powerful in surrounding yourself in the thing you want to avoid the most.

I found myself in the midst of a community of admitted failures who were brave enough to move beyond their emotional response to failure (shame, and all of the baggage that it brings) to pinpoint what went wrong, and how they were involved. A decisive resolve to own your failure helps to shed some of the negative hangers on of it – like assuming the whole thing is your fault, or taking it personally when it’s not intended to be.

At the same time a coworker noted how few things seemed to ruffle my feathers and I joked that being laid off helped me find my zen place, but really I had begun to differentiate between small f and big F failure, or as I think of them, oops and oh shit moments. An oops is forgetting a sign at the office on your way to an event, or not putting the toilet seat down in the communal bathroom. They are mistakes that maybe it would be best not make again. An oh shit is sending out an e-mail from your boss’ personal account to the VIP mailing list without clearing it with her first. Here there’s an opportunity for a revised external communications process, with room for a certain someone (me) to ask better clarifying questions about work tasks. My zen developed from being able to shrug off the oops’, and try to learn from the oh shits (though at the time, nothing else hurt more than the layoff, so to some extent I was still shrugging off the oh shits).

Two weeks ago we hosted the failure conference and I was blown away by how excited the participants were to talk about failure. Personal, professional, it didn’t matter – they dove in to conversations about failure like they had found an oasis in the desert. They wanted to take on the challenge of learning both about and from failure. They wanted to move forward, fully recognizing what had gone wrong, with the intention to do it differently the next time. They inspired me.

One year out from my layoff and I’ve had 5 contracts, planned, or helped to plan, 14 events for 20 to 700 people, but the failure conference has by far been the most rewarding. Today if you were to ask me about failure I would proudly share all the things I’ve learned from that work. Today I say “when I left” because it doesn’t matter now that I was laid off. That’s not what defines who I am, or the work I do. Losing that job remains one of the more painful things that has happened to me, but like any other failure (either mine or someone else’s) what matters most is how I learn from it.

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On Toast

I was at a diner with my Dad a few weeks ago, and in ordering breakfast, he requested that his toast be burnt. The owner paused for a moment, but nodded, and went back to the kitchen. When our breakfasts arrived, sure enough, the toast was well done.

My Dad is so specific about his toast that this year he bought a new toaster, in the hopes of achieving toasting perfection. He knows the difference between dry toast, burnt toast, crunchy toast, and any other modifier you can think of. I have never thought this much about toast in my life, nor used the word so much in a sentence.

I grew up thinking my Dad liked burnt things — when he would accidentally burn a batch of cookies, or leave a hamburger on the grill for too long, he would laugh it off and eat it anyway. He ate his mistakes, moved on, and somewhere in the process developed a very specific attitude toward toast.

This year has been my year of burnt toast. I had something of a high school reunion at a funeral. A family member I cherished, respected, and rooted a piece of my personal story in, passed away after a long and beautiful life. I spent half the year unhappy beyond belief in a job that asked me to be something I was not, and I wasn’t even able to admit how unhappy I was. I was then laid off from said job, and spent the other half of the year unemployed and staring down a black hole of personal crisis (not that you would have guessed that, my posts on here are nothing but sunshine and rainbows).

I messed up a lot. I neglected relationships, and ran broken hearted from others. I wallowed, selfishly, in circumstance. I forgot what was most important to me, and let that confusion build a barrier between myself and others. I wasn’t honest with myself, and let friends and family down numerous times. I didn’t show up this year.

This is my burnt toast, my blackened cookies, my charred burger. Hindsight lets me see that while this year was bad, I also wasn’t at my best, and that is something to learn from.

Chatting with Dad the other night, he said “what doesn’t kill us makes us stronger”, almost as if in passing. Never has Kelly Clarkson (she said it first, right?) been so right and has it been so clear why he prefers darker toast than most. In learning how to feed a family, switch careers, move countries, and raise children he might have ruined his fair share of food, but he also figured out exactly how he likes his toast (among other things).

I’m not making any resolutions this year. Instead, I recognize what the past year has helped me reap, and I’m going to ensure that stays constant. Never before have I been so sure of my close friendships, and I’m slowly circling in on how to prioritize those people over all other things. I get to practice that at one of my oldest and dearest friends wedding this year, and hold it as a beacon of hope and goodness in the months to come. My career is moving in a surprising, but wonderful, direction and I’m excited to build it upward and onward. More than anything though, I’m working hard. I know that I’m going to burn a lot of food, I’m going to eat it, and while I might not like it, I’m just going to keep toasting.

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On 2013

I am not generally one for New Year’s resolutions. Not because I don’t think you should strive to change or improve, but because I’ve always found it sort of weird to try and use the start of a year as the impetus for doing so. If it’s actually something you’re interested in doing, shouldn’t the date be irrelevant? Anyway, not the point.

THE POINT IS. I AM one for doing some yearend reflection. And what a year it has been, both for me and for the people in my life. I’ve seen relationships end and folks take new jobs. Friends have moved continents and love has grown. There has been loss, challenges, huge successes, and lots of fun.

Part of 2013 will, for me, always be “the year that injury stopped me from running the Scotiabank Toronto Waterfront Marathon” (I’m saying this now – and you can quote me – I’m going to fucking crush that shit next year). From an Embracing Ambiguity point of view, my year has been a bit of a rollercoaster. I’ve tried to map the major changes out. See the highly scientific, super rigorous graph below:


So clearly, things have (mostly) gotten less ambiguous as the year has progressed.

I started the year finishing up an internship at a Canadian charity and am ending the year working for that same charity. The one difference is that instead of interning I’m now (mostly) managing our major yearend fundraising campaign, and have an offer of an “actual” (non-contract) job on the table.

It’s quite a leap.

I’ve gone through a hell of a lot to get to this point: from multiple short term contracts to a sudden fulltime (contract) role, long nights and early mornings of proving that I had something to offer and offered something worth keeping.

And now, so close to the thing I’ve been aiming for since the day I graduated university (a job-job), it feels…different than I was expecting (maybe?).

In truth I guess I don’t know what I was expecting. I think*, however, that I thought I’d just feel like “me”. And in a sense, I do. But I also don’t…ya dig?

More so now than at any other time in my life, I feel certain in my uncertainty. I don’t have all of my shit worked out, and the way forward is still unclear, but there’s a greater…awareness? Like I’m no longer “faking it till I make it” – which, don’t get me wrong, isn’t to say that I’ve necessarily “made it” – but I definitely know some shit. And I’m definitely willing to fight for the chance to prove it.

The successes in my place of employment have also come coupled with a failure, of sorts, in my extracurricular pursuits. Those of you who read this blog somewhat regularly may know what I’m referring to: The Storytelling Project. Since early in the year, I’ve kept this quote above my computer:

“When I get to the end of this year, I want The Storytelling Project to be at a place where people and organizations are approaching me to have their story told, because they see value in what it is I’m doing”


The quote above is from a work retreat we had last January, where we were asked to think about our lives one year into the future. With one story produced and a few more stuck in development, I can’t exactly say I achieved my goal. There was a time when I would’ve beat myself up about that. A lot.

A time when I would’ve questioned what it was I had spent my time doing. Questioned if it was “enough”.

Now? I’m definitely a little bummed, but I’m also recognizing that I have done a lot this year. A lot I should be happy about and proud of.

I’m also recognizing that making a “splash” in the way I had hoped, is hard.

Like, really fucking hard. It’s uncertain, exhausting, time consuming (time you don’t have when focusing on the thing(s) that pay the bills) and can often feel like you’re trying to walk up a down escalator.

I’m recognizing that it’s okay it didn’t happen this year. All it means is that I get to regroup and try again in 2014.

I guess what I’m really saying, folks, are these two things:

1)      Embrace the ambiguity. It will never go away completely, but you will start to get a handle on it. You will. Even when it looks like that’s impossible. You will because you’re bright and passionate and driven and a fucking baller. And don’t tell me you’re not because you are. And if it doesn’t feel that way now, it will. You just need to find your place. Everyone has one. When you do find it, embrace it, too. Fucking own it. Don’t spend your time comparing it to someone else’s. You are your own unique snowflake. Remember that it’s not where you’re at; it’s what you do with where you’re at.

2)      Take it easy on yourself. It’s okay to stumble. It’s okay to fail. It happens. But you know what else happens? Recovery. Ass kicking. Take a second and think to yourself: what’ll be your Scotiabank Toronto Waterfront Marathon in 2014? Let’s crush it together.

I know these things aren’t “new” or even very insightful. But they are important. And they are things we can forget as we rush through the day to day, head down and feet moving furiously towards our next test. So take a minute to remember them.

All this said, I think part of what I’m saying is that (maybe) I’m growing up.

Just a tad.


Until next time. And next year. (Haaaaaa! Yes, I went there.)

Ambiguously yours,


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on facing the black hole

If you’ve been following this blog since its creation, you’ll know that a lot of what I started off talking about was my transition from University graduation, to soul crushing grocery store job, to internship with a Canadian charity and finally, to a personal venture I was really stoked about – The Storytelling Project. If you’ve been consistently following us since then, and are a particularly astute observer, you may have noticed that any further mention of the project after its launch has been strangely absent.

Things have fallen slightly off the wagon, it would seem. Not to say that I don’t still love the notion of pursuing it. Its just been, well, a mixture of things. Having a ton of footage but no time to edit it is the first problem. And to be fair, work (paid work, that is) has kept me quite busy as of late, and I’ve been doing a much better job at balancing my life – I’m still not sleeping a ton, but at least now I’m no longer working 15-20 hours a day.

All of these things aside, however, I think the main thing stopping me from pursuing it full steam ahead, is fear. Fear of the uncertainty. Of the question marks. Fear of the black hole. To pursue The Storytelling Project full time would be to risk it failing, to risk my financial well-being, to leave a job I am mostly stable in and, in general (despite recent events), enjoy.

I know that I love talking to people and collecting their stories. I know that I love using my skills in video production and narrative creation to craft a visually engaging story. I know that I love the idea of doing that as a career. I just don’t know…how. How to bring it from a fun, enjoyable thing I do in my spare time, and make it into a thing that pays the bills. I know that the answer is probably to just go for it, but it’s easier said than done. Especially when I get emails once a month from the Ontario government reminding me how much I owe in student loan debt.

Like I said last time, though, I don’t want to let money dictate my decisions. And so, the fun of transitioning to adult life. Things are never quite easy, and never quite clear. It’s a bit of a black hole. A bit of a journey through a thick fog. You know which way you want to go – it’s just the path there that is unclear.

And so that’s where I sit currently: at the intersection of where  am and where I know I want to be, one foot hovering in the air, slowly moving back and forth between the scary, uncertain path with the patch of light somewhere down the road, and the constant, familiar path that is lit along the way but doesn’t seem to be leading anywhere in particular.

I simultaneously do and do not understand how the choice can seem so obvious and so difficult at the same time. And its not like I dislike the things that I’m doing now – my job with a Canadian Charity and contract videography work for a University – I just know that they’re a place holder. A momentary thing keeping rent paid and belly full. They aren’t leading me anywhere beyond the place I’m already in. That said, I also enjoy them enough to keep doing them, despite knowing I’d be happier with TSP.

There are other parts to this quandary, too. The somewhat hilarious notion that I’m scared to start because I’m scared to see it fail, all the while the site sits un-updated, the footage un-edited, and my dream of taking TSP to a place where people and organizations are actively seeking me out to tell their story, as far away as ever. It has, as much by inaction as by potential action and outcome, failed. Then there’s the people I feel I’m letting down – those who believed in me and cheered me on when I started, and those whose stories I’ve collected but, by my inaction, smothered. Kept hidden and collecting dust, instead of letting them out into the wild, to be consumed by others.

Part of me wants to force myself into action by quitting my jobs. Fight fire with fire and overcome my fear by injecting a new kind of it into my brain; use the threat of dwindling groceries and looming rent payments to get my butt in gear. The other part of me thinks that’s stupid and isn’t afraid to vocalize it. I don’t know which part is right. I’m just hoping that, somehow, I can find the courage to step into the black hole and get things back on track.

Whatever does end up happening, I’ll be sure to share.

Until next time.

Ambiguously yours,


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On getting lost…

I can feel it starting again. It’s a slow but sudden creep that eases its way in – unintentionally, of course – but once it does, it’s almost impossible to stop. All of the passion, drive, excitement and enthusiasm of the past while just starts to trickle away. Keeping up with projects becomes more and more difficult. The lure of distraction becomes stronger and stronger, and suddenly, getting any real work done is near impossible.

I’m not sure why it happens, but when it does, it’s crippling. It can make answering even the most straightforward of emails seem a challenge. It also creates a silly downward spiral of emotion. I start out feeling crummy and demotivated for no reason, and this causes me to be overly critical of myself. It suddenly becomes that I’m too lazy. That I just don’t work hard enough. That if I really wanted to overcome this feeling, I could. That I’m just using it as an excuse to do nothing.

I can’t tell if this is a regular experience. If the others I work with also wake up to days where they just feel like lying in bed, curled up in a ball, occasionally getting up to eat peanut butter off a spoon. Can’t tell if it’s just me, or if it speaks to some deeper seeded issue of confidence.

It’s a difficult part of this transition to real people life though. To feel so passionate about a project one week, only to completely lose steam the next, is incredibly challenging. I constantly find myself questioning whether I’m the right person for the task, questioning my abilities and my decisions about the work I’m going to do. I often feel as though I don’t do enough. As though I don’t work hard enough, or push myself far enough.

Confidence is a shaky thing, it seems.

On the one hand, I know this sounds crazy. Anyone who knows me and the 3hrs of sleep I average a night would probably agree. But on the other hand, I can’t help feeling this way. Despite whatever praise I may get for a job well done, it constantly feels as if it isn’t entirely deserved. As if I always could’ve done more. I constantly struggle to understand whether or not that is actually the case.

Perhaps part of this comes from the idea that, compared to the people I work with, I’m still a kid (less in age, more in experience). Perhaps with this view comes a belief that what I’m doing can’t possibly be as good as what others could do; this then feeding into the cycle of uncertainty that leads to those crippling moments and days of “I can’t do this…where’s the peanut butter?”. I don’t know for sure, but perhaps?

I’m realizing quickly that this is something I need to work out, and fix, before it continues to cause me problems. I’ve lately been considering applying for a new position at work, for instance. It would be a considerable step up (to a managing position) and with the experience I have with the particular project, I am – at least on paper – somewhat well poised to have a reasonable shot at it.

That’s on paper, though. My head, on the other hand, is plagued by doubts and fears. Doubts about whether or not I could handle it, could do a good job, and could stay organized. Fears that I’d let people down; people who’ve invested a lot of time and belief in me.

Which again, is probably silly. I’ve yet to completely botch anything just yet, so I don’t know why I’d suddenly start now.

I think that, perhaps, part of all of this is actually something positive (at least, here’s hoping). Within all of the uncertainty and fear is, I think, a sign that I’m on the right path. If I wasn’t doing something I was truly passionate about, then I can’t imagine that same level of concern would exist – concern about whether I’ll succeed, whether I’m the right fit for a role or whether someone else could do it better. Perhaps there is no “transition to real people life” where suddenly everything makes sense. Perhaps I just need to get better at working through and becoming comfortable with these uncertainties, instead of letting them get the best of me.

Then again, what do I know? I ate popcorn for dinner last night and spent yesterday on a bike, in a Superman costume.

Until next time.

Ambiguously yours,


On failures, fuckups and missteps

If you’ve been following my posts on this blog (all two of them), you’ll (hopefully) know that I’ve been telling the story of my journey from graduation to where I am at now – I thought this would be a good way to kick things off before delving into more specific topics.

Last time, I ended off with a hint about something that I stumbled into in late January of this year, and have been pursuing since – The Storytelling Project.

I was all set to crack that can of beans wide open this week; to let you waft in the sweet smell of preservatives, when I came across this image:


Immediately, I knew that I had to take a bit of a detour. See, that image has essentially been my life the last few months. Despite the excitement that has come with pursuing The Storytelling Project, I’ve also spent much of the time feeling like shit.

It’s the result of a number of things: the shot confidence that comes from multiple job rejections. The financial stress of only having part time work that barely (if even) covers expenses. The emotional ups and downs that come with still working through the after effects of a breakup.

It has been a constant struggle to stay motivated and upbeat; to get out of bed some mornings. I routinely have days where I don’t. Well, except to eat copious amounts of cereal.

Side note: Cereal is the greatest fucking thing on the planet

Within this maelstrom of emotion, I’ve spent a lot of time dwelling on my failures, fuck-ups and missteps. Those three things characterize much of my last few years.

Example: when I applied to the University of Toronto’s Philosophy program, and then switched out of it after two weeks, and into English…which lasted another few months. English to history, history to…Middle Eastern Studies? How’d that even get in there? To, eventually, settling on a major in Peace and Conflict Studies. What a mistake that was. At U of T, the PCS program starts in second year. At the end of that first year in the program, I wrote a paper and gave a presentation called “Why Peace and Conflict Studies Sucks” (I think my professor really enjoyed it).

I wanted to drop out.

But…I didn’t. I didn’t have the courage to face the black hole that life would have become. The uncertainty, the second guessing and the limitless (read: overwhelming) choice.

Besides, I was already two years and $15,000+ in, might as well finish what I started, right?

Besides, I was “supposed” to get a degree, right?

Besides, despite my dislike of the experience, my marks were excellent, so I should just be happy; grin and bear it, right?

But the fuck ups are not limited to school.

From bad financial decisions…spending money I didn’t have on shit I didn’t need.

To career decisions…failing to move quickly enough, or with enough motivation and drive to secure jobs; failing to suck it up and work jobs I didn’t want when the need for money was greater than the need for job satisfaction.

To relationships…failing to see beyond my own somewhat abnormal obsession with work; failing to balance my priorities and fucking up one of the few things that had been consistently positive over the last couple years of this journey into adulthood.

Our failures, fuckups and missteps litter the road from adolescence to “real people life”. As I stumble down that path, tripping over all that is strewn about before me, I’m realizing that the hardest part of that transition is not letting the fuckups drown you. The hardest part is realizing that everyone has them, and that they don’t make you any less than you are. Realizing that, in the grand scheme of this thing we call life, they really aren’t all that big a deal.

I can’t pretend that I’ve gotten any good at any of those things (I also can’t pretend that I am not currently sitting on my bed as I type this, drowning my feelings in a box of Ritz Bits sandwiches). I just know that they need to happen.

Hopefully, through this blog, we can try and get to that understanding together.

Until next time.

Ambiguously yours,


Bonus! This song made me feel really crummy today. It’s great, though…


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