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I’ve had only a handful in my adult life and they were all red.

I am naturally talking about lipsticks. What are you thinking??

I have never been a lipstick person. Growing up in a very relaxed country in the 1960s and 70s, lipsticks were the purview of my mother’s generation, not mine. I put makeup on my eyes, but never my lips.

With the exception of weddings, that is. When going to weddings, I’d wear lipstick and it was always red. And then I never wore it again. That is, until the next wedding, when the inevitable debate was whether the lipstick that had been rattling around in my makeup bag or drawer was still good or if I should purchase a new one. If the latter, it was red again. And never worn again after the big day.

And then a whole lot of things happened and collided in the last two years.

There was the medical adventure, which has had a significant impact on my life and no, I’m not just talking about the PTSD. For a very long while, I have struggled with how to reclaim my life, how to find a way to plug back into joyful living. To live in a way that acknowledges the gift of yet again being handed another chance at my life. Not exactly on a silver platter, but still.

Twelve years ago, I honoured my second chance at life by changing how I lived and who I was and that’s hard to beat. And then, a few months ago, it hit me.

Regardless of how changed I am, there are still some things that make me uncomfortable, some that I even find scary. And since I don’t want to waste the rest of my life backing off from anything, why not challenge those fears and discomforts?

And just to make sure that I am accountable — to myself and others — why not record them on video and share them with the world?

There’s a reason The Boy calls me All-or-Nothing Girl.

The other thing that has entered my life in the last year is YouTube videos. I never knew how wonderfully relaxing it was to poke around the different channels, but now I’m subscribed to at least a dozen and many of them are my go-to moments of calm and sometimes a laugh of the day.

Enter Boldly and Ladylike, both Buzzfeed channels, both targeted at women. And that’s when I got some inspiration. In a Boldly video some time ago, Jazzmyne challenged some of the other women to try bold lipstick. Fun video, which percolated in my brain for a while.

So why not try it? That could be an interesting way to challenge my discomfort around lipstick. The video above this is the result.

For those of you who might have become enamored of any one of the lipsticks used in the video, specifics are as follows:

• Day 1: Smashbox Be Legendary Matte Lipstick, Talk To Me
• Day 2: Sephora Collection Cream Lip Stain 10 Mandarin Muse
• Day 3: MAC — Anything Once (might be unavailable – I can’t find it on the MAC site)
• Day 4: Sephora Collection Cream Lip Stain ~ 29 Dark Forest
• Day 5: MAC Matte Lipstick – Dreampot
• Day 6: Smashbox Be Legendary Matte Lipstick, Screen Queen
• Middle Aged Vampire: MAC Satin Lipstick Cyber 3G
• End of video: Sephora Co;;ection Cream Lip Stain 01 Always Red

And yes, I am particularly enamored off the Cream Lip Stain Liquid Lipstick from Sephora — it’s wonderfully vibrant and sticks to your lips through almost anything. Except apparently eating toast (see Day 4).

This whole experience has had ramifications. Because of my now-increased comfort level with lipstick — I actually quite like it, especially the fun colours — and a certain friend and enabler, I accidentally/on purpose purchased the NYX Liquid Suede Cream Lipstick Vault during the Boxing Day sales. And aforementioned friend (this is JJ, The Boy’s sister) and I have decided to work our way through all 30 colours, one day at a time and I’m starting tomorrow. Because it’s January and you have to do something to liven up this time of year.

You can follow along on Instagram as I wear every single colour, no matter what it looks like.
What do you think I should do for my next challenge? Leave your suggestions in the comment section here or on the lipstick video on YouTube. Subscribe if you’d like to keep up with my next crazy idea.

How you feel about lipstick?