Published On: December 1, 2023By

This month we’ve got crushes so nice, we’re writing about them twice! Kendra Penner, a photographer, and Hayley Penner, a songwriter and author, are two talented sisters with a famous father named Fred. We sat down with the pair to chat about everything from growing up in a creative household, to navigating the creative industry, finding your passions and even getting inked.

Unlike many of our Creative Crush conversations, which are often done online, we were lucky enough to invite Hayley and Kendra to our Winnipeg office. This change in setting not only set the stage for a fantastic chat with two seasoned performers, but also made for a wonderful opportunity for the two to play off of eachother in a way only sisters could.

Hayley: I’m getting a Yahtzee tattoo for sure. I’m getting snake eyes.

Kendra: You should, I support that. Snake eyes? 

Hayley: Yeah, two singles are snake eyes. She hasn’t been playing Yahtzee for as long as I have. I don’t want to brag but…

Tell us about yourselves.

Hayley: I am a human woman. I’m 37 years old. I say my age because I’ve been hooked on the Julia Louis Dreyfus podcast. Have you been listening to this? It’s amazing. She interviews aging women, and I’m proud to be an aging woman. So I’m starting with that. I’m a songwriter. I’m a writer, I’m a sister, I’m a friend, a cook, a thief—

Kendra: You are. She has a real habit of taking things and then leaving things she doesn’t want behind. It’s like, “I don’t want this.” That’s why I threw your scrunchie at you today. I was like, “I don’t want this!” I’m Kendra, I’m a sister, I’m a photographer. I used to be a dancer. I taught Pilates. I’ve done a lot of creative things. I went to design school for a little bit. And now I just do photography. 

Hayley, what’s one thing that you wish you knew about the music industry before you got into it?

Hayley: No is a complete sentence. You know, at the beginning, you don’t know how to leave a space because it’s not like we have a session from two until six. The session starts at one, and then you leave when it’s over. It made it impossible to make plans, impossible to make friends, impossible to build a life in LA. So just knowing now that you can walk into a room and say, “Okay, I have until six” or “I have plans at seven” and it doesn’t slow down productivity. It actually hurries up productivity. Everyone has an understanding of what the day looks like. Structure is great for productivity and creativity. 

And like any muscle, the ability to say no is like a muscle. It was hard to use at the beginning, it was tough. I would have to coach myself into it for a while, but then eventually you get better at it. I also think that’s a product of aging and just slowly caring less through time. 

Kendra, what’s one thing that you wish you knew about the photography industry before you got into it?

Kendra: Saying no is a huge one. It’s great. It’s important to do. Say yes to things you want to do and don’t just take all the work that comes to you because that never ends well. If it’s something you don’t actually want to do, or things aren’t lining up right, follow your gut. 

I didn’t really know just how much of it is not about shooting. It’s actually running a business. There’s so much more than just photography and the actual business side of it, than I knew was there. I have an accountant, but I still have to do a big part of that. And the amount of editing and the amount of social skills. Working in the restaurant industry for years I think was really helpful, managing and knowing how to work with people, how to deal with conflicts. That’s something I didn’t really think about when becoming a photographer. 

Have either of you ever doubted your talent? How do you get past that doubt?

Kendra: If there’s something really specific that’s come up then I will reach out to friends. It always comes and goes and sometimes I know it’s there and I think, what am I doing? And then it just fades. Something happens or it creeps in and out but I don’t think I’m always aware of it.

Hayley: What, like today? Yes. It’s funny because it’s never just a bit of doubt. I’m either certain I’m a genius, or fully stupid, there’s no in between. And how do I get over it? I walk. I walk a lot. I talk to friends. I let friends remind me I’m good. Friendship and walking. 

Friendship + Walking = Happy Life. Beautiful recipe, honestly.


What does the creative process look like when you’re behind the scenes?

Hayley: I feel like my creative juices come from walking. If I’m ever stuck on anything, I’ll go for a walk. Walking is the thing for me. And if I’m at home working, writing on my own or something, it has to be dead silent. Sometimes I’ll put on earphones even though I’m in a quiet house, just to feel totally isolated. 

Kendra: I find it’s different depending on what I’m doing. I think unintentionally, I’m often in silence. I have to really know what I want to listen to in order to listen to something. It’s hard for me to just have something on unless it’s really fitting my mood or what I’m working on. But every Monday I listen to Smartless. Sometimes if I’m editing for a really long time I’ll have my TV show on in the background or my casual Spotify playlists. I feel like it either needs to be completely silent or I’m choosing to go sit in a coffee shop or a busy place. And I really like that sometimes, it makes me feel a little more motivated. 

Hayley: Yeah it’s easier to not then hit a wall and turn on a show, because I’m not going to go to a coffee shop and then watch Frasier. I could, but I’d be too embarrassed.

How do you deal with burnout? What are some things that you do to help protect your mental health?

Hayley: The feeling that I associate with burnout immediately becomes extreme sadness. If I’m not prioritizing wellness or walking or whatever it is that makes me feel good, it will immediately show up as something else. And I think with Kendra, it will immediately show up as anxiety. Right? It’ll become obvious that you need to make more space for you.

It shifts quickly. It doesn’t stay as, “Oh, I need a break.” I never feel that way. I haven’t felt that way in 20 years of doing this that I just needed time off. But if I’m feeling exhausted by something, then I get tremendously sad and I feel like a loser right. And then I get mad at that voice that’s calling me a loser and that’s it.

Kendra: I think burnout is something that I’ve struggled with. A real goal of mine is to create separation between working and then being off work and with my job because it’s so easy to stay connected, to look at my phone, look at an email, think I should post something on Instagram right now. Everything is so available to me. But burnout just lingers and then it will dip away and then it’ll come back. I think cooking for me is one, I really try to just give myself time to cook. Breathing a lot, breathing is really helpful.

I reach out to people a lot if I’m feeling stuck or have questions. Having a real community around me, I think is probably the most important thing. And if I feel like it’s a dumb question, or I’m a little lost in something, the more I reach out to people, the better it is, because it’s very easy to just get stuck in my head and think something’s not going right, or I’ve done something wrong. 

As I start talking to people and hearing their experiences, and sharing stories it always makes everything better.

Hayley: I do find having friends who are not in your industry is incredibly helpful, just reminding yourself that the world is not your industry. So to talk to people in other industries, who are also sometimes not 100% fulfilled and thrilled all the time, it’s helpful for prospective.

And when conversations do come up surrounding work with someone who isn’t in your field, it really comes from a truly curious place. I really want to understand how things work. It’s not a pissing contest. Which is what sometimes it becomes  when you’re with another songwriter. They’re like, “Oh I just got this cut,” and you have to be like, “I’m so happy for you.” And you are happy for them, but also then you feel bad about you. It’s a lot of negotiating envy to just have a coffee with someone you admire sometimes. So sometimes it’s nice to just talk about a different industry and exist in it with curiosity and excitement and interest and have it be in no way a reflection of your personal success in that moment. 

I don’t keep Instagram or TikTok or anything on my phone. If I’m posting I load it up, I close it, I take it off. Because obviously, mental health, no good, we can all agree. You’re never going on Instagram and leave thinking, “I feel better about me and the trajectory of my life.” Never, I only leave feeling jealous and bad and not where I’m supposed to be and not good enough. It’s not a helpful environment for mental health. 

Kendra: Yeah, I mute people often. Or I make it a real choice when I’m looking at other photographers or other creatives and how they’re working, versus just always having them open. Because then I’m only comparing myself to other photographers, or thinking, “Oh, I like that style. I want to do that.” And then I end up totally losing how I’m shooting, and it doesn’t feel like me anymore. I make sure that I’m not looking at other people regularly. And then when I do, it’s a choice, or I try to make it a choice, or I’m trying to connect with other people. But yeah, to not have it around me all the time because it just becomes really easy to compare.

I’m sure this is a question that you’ve never been asked in your entire life, but what was it like growing up with Fred Penner as a dad?

Kendra: As a kid being asked that question, I was like… he’s dad. Like “Well, what does your dad do?” It was just his work. He was on the road a lot. So he wasn’t always around and then when he was, it was fantastic. It would take forever to walk through a mall with him, like a very long time.

My favourite “walking through the mall” moment with him was when this couple came off the elevator after we had been stopped every 30 seconds to sign autographs. And this couple came down and had British accents when they chatted for a second. He was like, “How did you know me? I’m just curious, I’m not very well known outside of Canada.” And they were like, “Oh, we have no idea who you are, you’ve just been signing autographs all day so we figured we should probably get your autograph too.”

Hayley: Really?! That is so weird. It’s so exciting because now as an adult, I’m just like, what he did was phenomenal. Objectively looking at the arc with his career it’s mind blowing. So now I’m just so inspired by him. His show started when he was 41. I’m 37. I love a later in life success story. He didn’t know what he was doing. He was doing shows here and there. He went to university, he’s going to be an economist or something. This was a later in life thing that happened in his 40s. With his second child just born, he was going to be a parent and just figure it out. So I just really connect to it. 

Anything can happen, the world is a big, beautiful, magical place. And I’ve certainly been kicked around a lot, but I still believe that so completely. 

And I feel like he has that too. He’s such an optimist. And he’s so excited about the world and life and possibilities, and it’s just so beautiful. Such a beautiful spirit. 


Fred Penner as photographed by Kendra Penner.

Black and white portrait photo of Fred Penner taken by Kendra.

So being part of a creative and artistic family, did you feel like that came with expectations that you were limited by?

Kendra: I feel like we all were really given the room to do whatever we wanted to do. I danced since I was little, so I think mom always wanted me to just be a dancer, but I got no real pressure to do it. I think Dad secretly wanted me to be a doctor because—

Hayley: Well, we all did. One of us should do something—

Kendra: Well, sorry about that.

Hayley: There’s still time!

Kendra, you are great at making your clients (including some of us more self-conscious UpHousers) feel comfortable in front of the camera, and just as importantly love their photos when they come back. How do you do it?

Kendra: I think it comes from so many different things that I’ve done throughout my life and so many different jobs that I’ve had from dancing and just being around people all the time. That’s a big one for helping me tell people how to pose or how to move their bodies in a really natural way. And trying to connect with the people as much as possible before we actually get into a shoot, or even as we get going. I’ve got a few little tricks for when we’re shooting, just telling people to breathe or close their eyes for a second. And I always have music playing. 

I think in general it’s just connecting with people and trying to make them feel comfortable. And trying a lot of different things too, in terms of people liking photos. I want people to feel comfortable, it also helps me do my job, and I want to feel comfortable with them too. So creating a connection with them is so huge and helps me love my job too. Otherwise, it’s just all downhill from there. Make sure that they’re okay in front of the camera and just take your time with it too. I really try not to rush when people are doing a portrait session, going as slowly as I need to. 

Hayley: I also just think it’s who you are, and have always been. You are not an aggressive addition to a space, you are only a nice welcoming addition to a space. People don’t feel like your presence is pushy, or too close, you have very good spatial awareness so you can move in a way that is both invisible but also very supportive. 

What’s one thing that you want people to know about you?

Kendra: I want to connect with people. I want to engage with people. I want to work out problems when they come up. I’m just here. I’m just human. Be nice.

Hayley: I feel like I’m such an open book, like there isn’t a ton I’m not thinking and then immediately saying. So my brain really goes to things I like to cook or bake or make, you know, recently I’m on a real chia pudding kick. I’ve got a big thing of chia pudding in my fridge at home. 

Kendra: You want people to know that you love chia pudding?

Hayley: I want people to know that I have chia pudding in my fridge right now when it’s empty, I’m gonna make more. And sometimes I take a scoop of it and walk right out the door. 

Kendra: Yeah, it could be a very small thing. I make great risotto.

Hayley: You make great risotto!

Kendra: We love to cook

Hayley: Yes and… Yahtzee 

Kendra: And it all comes back to Yahtzee

Candid photo of Hayley and Kendra laughing as they bake together.

Next week, we’ll be diving into Kendra and Hayley’s inspirations, momentous moments and what it’s like to find yourself as an impromptu author in LA.