Jennifer Couldrey

Jen Couldrey, was named a Women’s Executive Network (WXN) 2018 Canada’s Most Powerful Women: Top 100 Award Winner. Jen joined Upside in 2016 as the Foundation Manager, with the aim of helping to grow the Upside Foundation nationally. She now serves as the Executive Director of what has become one of the country’s largest tech-focused charities. 

Prior to leading The Upside Foundation Jen worked in corporate social responsibility at SiMPACT Strategy Group and human capital consulting at Deloitte. She also serves on the Board of Directors for Future Possibilities for Kids and on the SickKids Tech & Innovation Advisory Council. Jen has been recognized as one of the Top 30 Women Making a Difference in Tech by Ryerson DMZ and as a Corporate Knights Top 30 under 30 Sustainability Leader.



Jennifer Couldrey talks about the burden of achieving more, more, more and what it has taught her about what is actually important. She also shares a heartwarming story that changed her life and what we can do to be human beings instead of human doings.


Thank you again for agreeing to do this. When we met, I definitely felt a connection with you. I loved our talk on deep friendships.

Yeah, of course. We had a strong connection and an unusual type of conversation too, which was very refreshing.

Thank you. I wanted to say congrats on a major award that you just received for your work. People know of your accomplishments, but I would love to know you as a human being. What’s your story? 

I feel very lucky because I am a very privileged a person- I had a charmed childhood. Maybe it's because I do a lot of reading and watching movies and you see other people's experiences, from terrible tragedies to smaller challenges…you realize very quickly how blessed you are to live a ‘normal’ life.

I've always felt this big responsibility to give back and help other people. I volunteered a lot as a kid and in high school. I thought that I was going to go save the world, live in other countries and do international development work. I didn't really learn until a few years ago, that even if you have good intentions, you can't help anybody unless you actually know how to do something useful.

I decided to go to business school, so I could learn foundational skills. I went with the intention of fixing the world from the inside out. Getting into corporations and then fixing the world from the inside.

I really wanted to do international development work, so I went to Africa for an internship. I'm very glad I went, but it turned me off of doing that kind of work. I felt very jaded from the experience. I felt like there was so much corruption there, which isn't necessarily fair because there's corruption everywhere. I felt like the work I was doing wasn’t making an actual impact. We were fitting in with the already existing system, which I wasn’t convinced was making meaningful change. I didn't love it and decided not to pursue that as a path.

I set aside impact for later and focused on building a business career. For a few years, I focused almost exclusively on work: I was in consulting at Deloitte and I really enjoyed it. Later on, I started volunteering with Toronto+Acumen, which focuses on impact investing. I started learning more about the business applications of impact, and decided to shift my career in that direction. I took a new job in corporate social responsibility consulting, which was a perfect transition for me.

I learned a lot and I enjoyed the work, but it didn’t feel like a perfect fit. I hired a career coach and worked on figuring out what I wanted and what was important to me. Through our work together I gained clarity on the types of things I liked doing, which was operational focused. It was then I realized I wanted to build something and not just advise other people on building.

This role came up [the work she now does with The Upside Foundation] and it perfectly lined up with everything I wanted: very operational, very entrepreneurial. Working with tech startups sounded super cool. With business wrapped around impact, it was a perfect fit.


I really respect the work you do. My family is passionate about philanthropy and that work, giving back, is so needed.

I love the Upside model. I think it's very innovative. To me, it’s meeting the world where it is actually at today. A while ago I read about how global consciousness is rising. Before, humans were in survival mode, but now we're at a point where we can be conscious about the food we're eating, the clothes we're wearing, and the impact of companies.

It's very cool to step back and look at how humanity is caring more about the impact of their actions- and to be a part of enabling people to take positive action.


Yes! What is it like to be in your role?

There’s a lot of excitement, freedom, and meaning because the role is very self-directed. Our founding team has always been supportive and accessible to me, but it was clear from day one that I had freedom to do what I thought was best to help us meet our goals and expand our reach.

I started going out to a ton of events to meet with people in the tech community, and speaking at them to spread the word about Upside. Probably a month in, when I first spoke at an event, I totally bombed. I forgot what I was saying halfway through. But it was so fun to be meeting all these entrepreneurs and in such an exciting industry.

I think something that all founders or people in leadership roles can relate to is the feeling that the responsibility of our success or failure sits squarely on my shoulders. No matter what we achieve or do not achieve, it feels like it's attributed to me. It’s not true, of course, because we have a Board of Directors and a founding team who are all involved and who help and are very supportive. But I feel the weight of that very heavily.

2016 was a year of learning. 2017 was very exciting because we had a campaign and we just had so much growth and momentum. Everyone was so excited about what we were doing and that was thrilling. 2018 was very much a step back, embed processes, build a foundation for growth, and fundraise year. I had no idea what I was doing when I started in 2016, and sometimes I still feel that way- I think this is inevitable when you’re building a new organization and doing something that’s never been done before- but that doesn’t make it less hard. You just get comfortable navigating unfamiliar territory.


Like so many of us. Building the plane as we fly it.

Exactly and adjusting as you go, testing, and seeing what sits. It feels like if this fails, it's because of me and because of the choices that I made or how I chose to spend my time. That pressure definitely weighs on me every day.


Thank you for your honesty. What's been the most surprising part of your journey?

The ups and downs. I thought that once we hit a certain level of success, we would just continue operating at that level. It is still so up and down and it's so exciting when we get a big win, award, or member. But there are a lot of lows that come along with that.

I remember seeing someone I know win a Top 100 Award and being so in awe of her- thinking she had accomplished so much and had ‘made it’. It was a funny feeling, when I received that award- because I definitely did not feel like I had ‘made it’. But then I realized that everyone else likely felt the same way. Just because you're winning awards and having some success doesn't mean you don't still experience failure and rejection consistently. It was both disheartening and refreshing to realize this.


I appreciate that you’re being real. We rarely talk about that side, how difficult it can be.

When I was younger, I always figured when you're young, you work really hard and you work really long hours. And as you get older, you become an expert, so you get better paid, you work less hours, and it's not as hard because you've got it figured out.

I just figured it would get easier at a certain point. Some things get easier…but as you grow in your career and find success, you are simply faced with new challenges that you don’t yet know how to handle.

But, it doesn't get easier.


[both laugh] We can laugh about this now, but it wasn’t funny at the time.

That’s just life, right? You just have to get to a point where you accept that. To accept that I will always live in a state of tackling hard things and feeling like I don’t know what I’m doing, and that there’s too much on my to-do list to realistically be done. Every day I work on making a conscious decision to do the best I can, let the rest go, and life my life. To find a way to let the challenges drive you, instead of letting it bury you. You realize it’s not going away.


The ups and downs, they can be so intense too. No amount of reading and courses can prepare you for that.

Yes. I read an article recently that told the story of an ambitious man. He grew up in a small town in Kentucky, and decided he wanted more out of life- so he left the town and went off to have a big fancy international career.

His sister stayed home and became a teacher, and inhabited all the stereotypes of the South, shooting guns and hunting animals. They never got along because they could never see eye to eye on anything.

Then his sister got cancer and he came back home and saw how the town rallied around her, how people took care of her kids.

It was then he realized, “You did life right. I did life wrong. You have this community of people around you who know you and love you and care for you. I don't have that. I have a bunch of acquaintances and I've built this great thing, but it actually doesn't mean anything because I don't have this community.”

It resonated with me a lot because my sister just had a baby. I didn't really understand where she was coming from because she wanted a simple life with her husband and baby. I was always out building this career and chasing things, pursuing things, wanting to travel, hungry for more.

Now I see her with her baby and she's so happy. I ask her what she does all day and she tells me about feeding and napping and changing diapers- I ask her if it’s boring, but she says no, she absolutely loves it. I don't think I will ever be as happy as she is with her baby. Because by definition, being an ambitious person means that you are never really satisfied with what you have. You always want to build more, learn more, do more, achieve more. When does that ever end? When are you ever satisfied with your life and feel like you can just enjoy it?

You never do. You always are telling yourself: I'm not working enough. I'm not spending enough time with my family. I'm not working out enough. I'm not sleeping enough. I'm not enough.


I relate to that. Last year, I was working too hard and I wanted to relax. When I went to my to find a book, I realize all the books on my shelf were non-fiction. Self-help, business, spirituality. All the books.

I cried. It really hurt. It hurt to realize that after all this time, after all the years I dedicated to entrepreneurship, even my books were about improving myself. When have I decided that I made it in the world? What you shared resonated with me.

I totally hear you; that's exactly it. You look at what you've accomplished and realize, five years ago, I would've been blown away by what I've done. But today, I still feel like I’m just getting started; I still have so much want to do.

In some ways, it’s great to have a growth mindset. To want to accomplish more and achieve more, but in some ways, it's just exhausting.


It brings to mind the topic: What does it mean to be happy? A lot of people long for that.

Let me share with you a story first: I remember when I was joining Dovetail [a women founders’ community that we are both part of], on Facebook, you're supposed to introduce yourself.

I went first and I shared what I do for a living. The next person, she starts saying, “I have two kids and I love to do this.” It made me realize how much I wrap my identity up in what I do…and that it’s okay to talk about yourself in a way that doesn’t revolve around work.

I have other stuff that I do and other relationships that are important, but ask me who I am? That's the first answer that I give.

But ultimately, for me, my definition of happiness is to live spaciously and joyfully with impact. To keep ‘doing good’ at the center of what I do, but to not get so wrapped up in my work that I forget to live a full life. A life that’s not defined by a to-do list or a set of accomplishments, but that is full of moments and people that matter. I’m actively working on the ‘spacious’ and ‘joyful’ parts.


It’s hard to resist having your work define you because for founders, the role can take over our lives. It can be quite stressful. I am curious to ask: When there's times that you're having a low, what helps you get back up?

Good question. I have an email folder called Wins, and every time someone says something nice me, I file it away in there. But I actually don't look at it often; I should do that more.

A lot of the time, it's just removing myself from things and getting perspective. I feel like we have a tendency to blow things up in our minds to be way bigger than they actually are. Talking about it with other people can be really helpful.

Sarah Stockdale had a quote about this. Anytime you're getting caught up in your head, remember it’s not about you. This is about the impact you can make for other people. Stop letting yourself get caught up in yourself, whether it's positive or negative, whether it's your ego or you're feeling like crap about a failure you had. Stop, let it go.


Yes, our journey can often be for the long haul. Marathon, not the sprint. When it comes to self-care, what does that look like for you?

I'm trying to draw very strong lines around work and not letting work take up all of my evenings and weekends too. That's become a big priority for me. My life suffers a lot when I'm not consistently working out, so that is also a priority for me.

Meditation is so popular among founders. I think it’s because people struggle to shut their brain off. I've done some meditation, and am working on making it a consistent practice.

Sometimes, when I’m commuting between meetings or events in a cab, I’ll throw on a meditation or just sit and do breathing. Allow myself to have a break, even if it’s only for ten minutes. It’s so tempting to try to jam every minute with productivity- but ultimately humans are not capable of being ‘on’ and productive for 8-16 hours a day. It’s so important to just breathe and be a human being for a minute.

The thing is, most adults are not good at these things. Children are very in the moment, very present. My husband and I always go camping every year- for 5 days, we go completely off the grid. We carry all of our food, we carry our canoe. There’s no cell phone service. That's critical time to get away and be quiet and just focus on the activities you need to be alive.

This sounds so corny, but last year I was really captivated by the rocks and the trees. They’re so beautiful. They're not trying, they're just being. It reminds me I need to do more being and stop trying so hard. I feel like I run around like a chicken with my head cut off all the time- not only is that a sad way to live your life, it also doesn’t necessarily even yield the results you are working so hard to achieve. I don't always have something to show for it at the end of the day.

That's when it gets really hard. When you're a results-oriented person and you don't meet your metrics, it’s such a hit to your ego and you wear that so heavily. Sometimes, it feels like you just put so much unnecessary activity and goals we think we have to achieve in our lives. It doesn't actually make us happier or more successful.

The rocks and the trees don't try, they just are. Same with children. They're not trying to be anything, they just are being how they are- and doing it very successfully. I think we have a lot to learn from them.


Well said and a great way to end. Thank you for being a part of this, Jen. I really appreciate it.

You’re so welcome. Thanks for having me.

Cherry Rose Tanwave1