How the Hardest Month of My Life Made Me Believe in Myself and Follow My Dreams

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Hey everyone, this blog’s going to get really real. And very personal. So warning… if you don’t intend to get to know me MUCH better than you do, I’d stop reading now. 

October had to be one of the weirdest, hardest, most emotional months of my life. I felt grief, joy, defeat, fear, lost, honoured, comforted, empty, and at least a dozen other ways. October 2019 changed my life (for the better I’m assuming… might be too soon to tell but I feel pretty good about it at the moment). 

So let me run you through everything that happened and then we can talk through how life changing the month was and the new directions and all that.


Leading into October 2019

Three stressful/challenging things were going on leading up to October. 

  • My Grandma, late in alzheimers, hadn’t eaten anything since the beginning of September (very sad, very stressful).

  • I just found out I didn’t get a job I was really excited about running the Intramural Sports program at York University. 

  • I was still dealing with the post-event depression that hits me every September after new student orientation is over and my sense of purpose is kind of gone.

Then October happened. Lots of good things happened and lots of really bad things happened… here’s the rundown. 


October 2019

Oct. 1st - I donated $500 of my earnings to Matthew House to support refugees settling in Canada because my mom’s friend had a lot of great experiences working with the organization and, frankly, I wasn’t using that $500 for anything else. 

Oct. 3rd - I got invited to interview for a promotion, Manager of Student Life, in my office. I had been looking forward to this opportunity since January when the office first announced this position was being created. Woohoo! Excitement :)

Oct. 9th - First round interview for the Manager job goes really well! I prepared as hard as possible and it paid off. I nailed that thing! Now I’m really excited and starting to picture myself in the job. 

Oct. 11th - My Grandma passes away. It hurts. I had lost my paternal Grandma back in June so I also felt very weird telling people that my Grandma died… again. 

Oct. 12th - My best friend tells me he’s moving to Spain… 6 hours before he takes off to Spain. I knew this would happen one day, but yet another shock to the system that it happened so soon and without warning. Despite everything that’s going on, I am happy for him.  


Oct. 12th-14th - I traveled to Niagara to see my mom and spend the next couple days doing those unpleasant errands that one has to do after a family member passes away (visit the crematorium, cleanout the nursing home, plan the funeral, etc.). 

Oct. 15th - I spend the day on my couch… literally couldn’t do anything else.

Oct. 16th - I return to work and get invited to a 2nd-round interview for the Manager job! Success! More excitement… but I’m tired. 

Oct. 16th (later that day) - Someone I care about (being vague for privacy’s sake) loses a young family member unexpectedly. Tragedy and heartbreak. Shit.

Oct. 17th-20th - I leave for a long weekend vacation to Montreal… exciting! I’ve been looking forward to this trip for a long time. Holy shit, though, I’ve got a lot on my mind and I’m so tired. 

Oct. 21st - Fresh off the Montreal Trip, Ariana and I commit to the Hawaiian vacation we’ve been talking about for 6 months and we buy our plane tickets! Wooo!!! 

Oct. 22nd - Everything I’ve ever wanted since I was 7 years old… Raptors Championship Ring Night! I go to watch the ceremony in Jurassic Park with thousands of fellow fans. I cry. They win. And my favourite thing… NBA basketball… is back. 

Oct. 23rd - I go to a breakfast to be honoured for an award I won at York University called the “Bryden Local Hero Award”. I eat breakfast with the university president, I make a speech, it’s great :) 

Oct. 23rd - I immediately leave the breakfast to drive to the funeral for the young family member of the person I mentioned earlier. It’s heavy. Funerals for young people are hard, man. 

Oct. 25th - It’s time for the 2nd round interview for this Manager position. I’ve been prepping hardcore for a while now (between all the other stuff, believe it or not). It goes really well and my hopes are high!

Oct. 25th - I go to a Halloween Party at the Ripley’s Aquarium… I’m a Dollarama Pirate. Very fun and much needed :)


Oct. 26th - I have my first counselling session in years. A very good idea considering the above. 

Oct. 28th - My Grandma’s funeral. Did you forget this happened? Yeah, what a month? I delivered the eulogy, I saw a LOT of people I loved, and I got some quality time in with my mom. All-in-all, a pretty nice day considering the circumstances. 

Oct. 29th - I trek back from Niagara to Toronto to attend a beloved co-worker’s going away party. She’s not leaving the university but she’s no longer sitting in ear shot after 4 years. Still a big deal. More emotions. My tank is empty. 

Oct. 31st - Remember that interview from a week ago. My boss pulls me into the office at the end of the day and tells me… we offered the job to someone else. I’m devastated. I feel like I’m falling into a pit of nothing. I fantasized about that job for so long… and now it’s someone else’s. It hurts really badly. I rushed out of work without having eaten anything all day. Luckily, Ariana (who I called instantly upon getting the news) thought ahead and rushed out of work to bring me a chicken bowl from Chipotle… with guac. My hero <3

Oct. 31st - I return to the Second City Training Centre for my first Improv class in 3.5 years. Thank god. Even though I’m distracted… devastated… and exhausted beyond belief… it was pure, untarnished happiness. I belong there.

So that was my month… it was nuts. Lots of happiness and excitement. Even more sadness and disappointment. And here’s why it helped me.

How All This Changed My Life

You read everything that just happened… well despite all that very time consuming, mentally, emotionally draining stuff, I still managed to produce $1,793 in profits in my resume writing / interview coaching business. Plus I missed out on another 3 clients (~$650) because I was too busy. 

I had no time to blog, no time to do any marketing, and barely even any time to do the work for my clients. 

If I can make nearly $1,800 (over half my monthly expenses) in a month where everything (good, bad, or horrific) is pulling me away from my business… what could I possibly do in regular month? What could I do if I actually dedicated myself to this thing? 

Honestly, this might sound a little corny, but doing so well in a month where so much went wrong… I inspired myself.

And not getting that manager job… probably a good thing, because who knows how long I would have stayed in that role and not pursued my business in a full-time capacity? Probably longer than I intend to now. 

So What’s Next?

To be honest, I’m still recovering. I’m formulating the pieces of an exit strategy from my current job (everyone at work is aware of this, so no need to start gossiping) and I hope to have a plan in place before the December break. 

I have spent years thinking about going full-time on my business and now, for the first time, I can see it in the horizon and it’s starting to feel real. 

Now I just need to bust my butt to prepare for that moment. 

Thanks for reading. If you want to help me recover, my best source of energy is compliments, so please comment here or wherever you found this blog.