If you’ve ever struggled to break a bad habit, this post is for you.
2013 will always be remembered as the year that I staged my very own “pajama-vention” – otherwise known as “that time I realized I was getting gross and decided to do something about it, and learned to kick-ass in the process.”
In December and January I participated in the Stratejoy Holiday Council. I learned how to let go of 50 things, made vision boards and set goals – some which I’ve already accomplished (!) I enjoyed the experience so much that when it came to sign up for the Stratejoy Willpower Council a few months later, I jumped at the chance. With my schedule now busier than ever, I knew I’d need to tap into my willpower to really “get shit done.”
One of our first tasks was to choose a bad habit that we’d like to change, or a good habit that we’d like to create. I knew right away what mine would be:
THE PYJAMAS.
As I’ve mentioned before, being a freelance writer and/or working from home does come with it’s shares of perks: a flexible schedule and dress code with a commute that never is longer than the distance between your bed and your laptop. The downside is that when you’re not even required to wear pants on a daily basis, things have the tendency to get gross pretty fast.
After almost a decade of working in a corporate office environment, when I started freelancing I embraced the novelty of being able to work in my pyjamas. However, what began as a fun and comfortable way to give the middle finger to my former office attire, soon evolved to the point where I was wearing my pyjamas all day, everyday. Unless I was leaving the house, I wouldn’t even bother showering or putting on clothes until late afternoon. As someone who is naturally prone to anxiety, my pyjamas weren’t just a wardrobe choice, they were like a security blanket – one that covered my whole body.
I jokingly nicknamed my well loved leopard print pyjamas my “freelancer’s business suit” and when I wore out my first pair, my Mom and sister lovingly purchased me new ones for Christmas complete with matching booties. You can file the photo below under “reasons I might be single.”
I hadn’t realized how bad the situation had become until my Mom and sister sat me down and told me I needed to start wearing real clothes around the house again. I agreed, but then told them I thought they were enablers.
“If you want me to stop wearing pyjamas, why do you keep buying me such awesome ones?! I mean, the matching booties: genius.”
My sister looked me in the eye and said, “Put on some real clothes Simone or I’ll burn those pyjamas in your sleep.”
The irony is, when I envisioned what my life would look like as a freelancer I didn’t imagine myself wearing flannel all day. Instead, I imagined myself wearing cute, casual basics as I wrote and worked on projects in my fun, colourful office. In other words, I wanted my day to day life to look more like my Internet Idol & Girl Entrepreneur Crush Jen Ramos (top left & bottom left.)
I could totally be the kind of person who spent the day working in funky striped dresses or a pair of leather leggings & a fun top. I already owned these kinds of clothes, so what was stopping me?! However, instead I settled for some approximation of this:
I knew I had hit rock bottom when I caught myself doing a phone interview with the head of marketing of a major Canadian bank wearing only a pink nightie, with a brown blanket wrapped around me.
That’s the thing I have learned about bad habits: they’re self sabotaging. We want one thing but we do another. I picked out clothes that embodied the vision I wanted for life, but stashed them away in the closet and instead, did exactly the opposite because it seemed easier somehow.
It wasn’t just the pyjamas that were the problem. It was my whole morning routine. I’d set my alarm early but instead of getting up, I’d lay in bed for 45 minutes running through everything I wanted to accomplish, instead of actually getting up and doing it. When I’d get up I’d be stressed and in a rush, so I’d reach for my “security blanket” instead of real clothes.
The first step to breaking a habit is figuring out why you have it in the first place. What’s the pay-off that you get from the behaviour? What need does it satisfy? Why did I feel stuck in my pyjamas?! Was it because I yearned for comfort or a slow ease into my day? Was it a deep seated desire to wear as much animal print as possible in a non judgemental environment? Was I just naturally gross & slovenly?!
After a lot of soul searching, I realized that I wore the pyjamas because I wanted to live my life on my own terms. The corporate world always seemed stifling to me and I wanted the opposite of that. Instead of a hectic commute, I wanted a slow ease into my morning and the freedom to plan my day – including what I wore to the “office.”
I spent a whole week experimenting with different morning routines to find one that would stick. Getting up and reading for 15 minutes. Getting up early and going for a coffee. Getting up early and doing Pilates before breakfast. Etc. However, the one that stuck was the most simple: getting up and showering immediately. I’d actually forgotten how good it felt to start the workday clean! The “comfort” of my pyjamas and lingering in bed was soon replaced with how awesome I felt when I got up early and got dressed.
I also learned that a simple maxi dress & a pair of flats is just as comfortable as pyjamas, plus I get the added bonus of feeling good about myself.
Except for a few days where I was legitimately sick, I’ve been pyjama free since the end of April. It’s amazing how much more confident and professional I feel in real clothes!
The great thing about exercising willpower is that it builds confidence. With pyjama problem under control, I felt ready for anything! When my Barre Method Teacher mentioned that she also taught a “Gladiator Workout Class” at a Martial Arts Studio in a neighbouring town, I knew I had to sign up. Why, you ask?! Because after reading Nicole’s post about changing your story, I wanted to change mine too. As humans we create our own stories about our lives. Unfortunately, a lot of them are very self-limiting. “I’m bad with money”, “I don’t have much willpower”, “I’ll never be a morning person” – these are all things I have told myself at some point. However, because I created these narratives I can also change them.
The Gladiator Workout is circuit training program that includes cardio, strength training, kick-boxing, yoga, Pilates and elements of boot-camp. It’s pretty intense and it starts every morning at 6:45 am. Which means that I actually have to get up, put on gym clothes and be out the door at 6:30am. Yes, me.
The crazy thing? I’ve been doing the Gladiator workout for a month and I love it. I never thought I was the kind of person who’d enjoy working out first thing in the am – let alone, do a workout that involves BOXING of all things – but I’ve discovered it’s the great way to start your day. In fact, when I was away last week I actually missed it. I even have my own pair of boxing gloves now!

I feel like I'm living in a 90's teen movie about a former Ballerina who takes up boxing and learns to kick ass, which is basically what's happening here.
I figured with my knack for attracting weirdos, I should probably take this opportunity to perfect my roundhouse kick. The workout is very challenging and is totally out of my comfort zone, but as it turns out, was exactly what I needed. Half of the time I’m not even sure whether I’m more proud of myself for completing the workout or getting out of bed to complete the workout. Either way, I get to start my day with my own private victory, which is awesome.
From Pyjamas to Gladiator. If I can do this, you can do anything.
What’s a habit you’d like to tackle?