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New Year reflections with photographer Kassandra Donaldson

Hi, hello! Welcome to our very first blog post here at Little Sister!

We are excited to launch this corner of the internet as an outlet for stories, celebration, community and highlighting cool people doing cool things. After all, there just isn’t enough bar-top storytelling like there used to be. 

Feature one: 2020 >> 2021.

Yikes! What a year. A year of twists and turns beyond imagination. It was not easy to navigate for anyone – as businesses, as well as personally. LSCM is truly grateful for the community that supports this business, and we are – as always – eager to have honest and engaging conversations with the lovely humans that make up that community. And for the first time ever, online to share! 

We are so excited to chat about 2020, and more, with our first guest: Kassandra Donaldson. Kass is a wedding photographer here in Winnipeg, specializing in candid, fun, personality-filled moments. Dog lover, local lover, and supporter of Little Sister; we are such big fans! 

Girl holds coffee cup, smiling, while standing in front of coffeeshop.


Welcome, Kass! What are your pronouns? 


Tell us about your background—have you always been a wedding photographer?

Pretty much! It started out in a pretty organic way, basically as soon as I knew it was a career option- I was in love. It took someone asking me to second-shoot for them to get started and trust that I could do it, but I’ve been happily shooting couples ever since.

How did 2020 affect you as a business owner? 

Obviously, 2020 was insane. I had a huge year planned with work but COVID changed it all! It was really interesting and challenging because of all the problem solving I had to go through, both alone and with my clients. I ended up with only about a quarter of the amount of work that I had booked... a stressful year to say the least. 

Did you have to learn or use different skills as a business owner? 

Oh yeah. It was a whole different level of communication and problem-solving. No one in my industry had dealt with something like this before so we all had to navigate contracts and ever-changing restrictions.


Girl sits on bench with camera in lap, wearing mask and looking away from the camera


But here we are! And you totally navigated it all. How did 2020 affect you personally? 

2020 was the year that I got married in a turn-of-events kind of way… in the midst of a pandemic and my grandma battling cancer, and in the middle of wedding season. Two of my best friends got married as well, so there was both a lot of loss and excitement. It affected my life a LOT. It’s so crazy how many highs and lows can all happen at once, you know? Good things and shitty things!

Big time. We feel the same. Holding space for mourning losses while celebrating wins, big or small, is essential. How have you been affected creatively? 

There was a little moment of “hurray!” at first when I was put out of work because a break was much needed, but it has long passed the length of downtime where it’s positive anymore. I have so many creative ideas but I’m just not able to do them. It’s been a strange place to be; to have so much time to think and do things I normally wouldn't have the time for, while feeling so stuck simultaneously! 

Coffee cup sits next to a girl holding a camera. Only lower torso is in view, sitting on leather bench

What’s the biggest lesson you’re bringing with you into 2021? 

Business-wise, the biggest lesson I’m bringing into this year is to let things happen as they come. Last year was so much about trying to control something that was just out of control, but now that we know more about what it looks like we can step back, let it happen, and figure it out as it comes. 

Personally, not feeling bad about being stuck. We all keep wanting to improve ourselves but sometimes we just can’t! I don’t want to feel bad for being at a pause when it’s out of my control. 

We know you’ve been involved with standing up for fair COVID-19 small business support for professional photographers in MB, what was that like? For context: initially, professions such as photography, event planning, artists, tradespeople and other small businesses without a storefront didn’t qualify for the Manitoba Bridge Grant. The grant has since been expanded. (#mybusinessisnotahobby) 

Honestly, I feel very proud of what everyone accomplished through the petition. Standing up for my industry is something I’m very passionate about, but I felt so lucky and even out of place to have been asked to do an interview on Global News. Lauren from Stone House Creative really got everything going and got us approved for the grant which has been a huge help to me. I still think there is more work that needs to be done as we (photographers) are still often unrecognized or thought of when new restrictions come out. I don’t feel I personally did much, but it all matters. The petition was huge. 


girl sits in sunny spot on a wooden bench with vines behind her. She is wearing a mask and looking at the camera.

What is your top “creative fuel”?

Creative fuel... I’m having lots of downtime so being the visual person I am... I get inspired by movies, other artists online, or just my clients in general, honestly just reading their emails! The fuel is knowing I can work again one day.

It’s been interesting finding other outlets, such as a workshop I led for Stay Close Canada or working on my website. This overwhelming amount of downtime has almost made me obsessed with being creative because I’m planning so much for when I can be back in action. 

Any hopes and dreams for 2021? 

That I can work! That things are safer. That we can be together again. That my nan’s cancer goes away. That whenever a new normal comes around that we would appreciate every moment we have and not take a single thing for granted!


Tea latte steeping in female hands, atop crossed legs in blue jeans.

Okay, we can’t help it. What’s your go-to order at Little Sister? 

OKAY, BEST CHAI LATTES IN TOWN, give me them iced or hot, I’m happy. Also- any new merch... I instantly order for me and my gals, hahaha.

What are your favourite local small biz’? 

Black Market Provisions, Out of the Blue, Linay Co, Riley Grae, Sydney Rose, Land of Hands, Oh Doughnuts… to name a few. :) 

Find her on Instagram @kassdonaldson

Photos by Sierra Pries

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