The Coffee Chat (#60)
My conversation with Erin Bury - Co-founder & CEO at online will platform Willful, Avid reader, Pizza lover and Mom to two girls!
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Hi there 👋🏽
I have a love-hate relationship with work travel.
I love the fact that it helps me reconnect with the old unencumbered me - the person who was only responsible for herself. After traveling with young kids, you truly appreciate the luxury of listening to a podcast or reading a book on a flight (though let's be honest, I'm usually plowing through a Deck!).
But I always find myself more exhausted for the next few days once I'm back. In your absence your SO plays the role of the lead parent which means the minute you walk in through that door, for the next few days for the sake of a happy marriage you solo parent!
Thank goodness for caffeine.
P.s: Last Sunday I did something fun - Was invited on the Purpose with Pals Podcast - (🎧) where I spoke about Taylor Swift and her dichotomous existence, my childhood growing up in multiple cities, making unconventional choices and why we all must not ignore the fact that we contain multitudes!
☕ Now, on to today’s coffee chat…
Meet Erin Bury
Erin is the co-founder and CEO at Willful, an online estate planning platform that makes it easy for Canadians to create a will in less than 20 minutes.
While she is frequently in the press talking about marketing and entrepreneurship (you will find her in the pages of The New York Times, Forbes, CNN, Profit, Inc., and Canadian Business. She also is a weekly tech commentator on CTV News), I was thrilled when Erin so generously offered me the time to sit down and talk about her reflections on being a working Mom!
We hit it off instantly - we are both moms to daughters and are daughters of strong independent professionally successful mothers!
Below is my conversation with Erin…
Please tell us a little bit about yourself and your family
I think first and foremost, I am a mom of two beautiful girls under three years old - a nine month old and a two and a half year old. I live with my husband Kevin in Prince Edward County, Ontario and moved out here full time in 2021. After living in Toronto for 14 years never thought I would live outside of a big city and I now live in a village - the village of Wellington and I absolutely love it.
Professionally I am an entrepreneur who has worked in startups for most of my career. Prior to being an entrepreneur I spent time as a tech journalist - I was on the founding team at BetaKit and I fell in love with entrepreneurship partly by writing about and telling entrepreneur’s stories. Post that I spent some time running a Tech marketing agency and then it was really my husband Kevin, who came across the idea for Willful and roped me into being a co founder and we've been running it together for almost seven years.
A few things I'm passionate about outside of work and outside of parenting. I love traveling. I've been to six continents! This year’s big trip is Morocco. I love reading - I read usually between 40 and 50 books a year, it is my #1 hobby. So if you're like how does she read that much? Usually the answer is I prioritize it over TV and other things but I also just absolutely love love is - Pizza. It is like a part of my personal brand. That's how much I love it!
I love that passion for Pizza, I can see it in your eyes.
I Peloton so I can eat pizza.
Ah well, whatever gets us moving.
So, something that caught my attention is that you and your husband are both co-founders, and you also parents together. There’s a lot of literature on the pros and cons of this, but given that you both manage a company and a household, how are you truly operating in this amazing dual career structure so well?
I reflect a lot on the dynamics of the expected roles, especially as a mom versus a dad. I grew up in a house where my mom and stepdad both worked at Nortel, both in tech. My mom had the bigger, busier career and was the main breadwinner. So, I've always had this example and a lot of ambition as a result.
To be honest, nothing brings me more joy than my two girls, but there was a time when I didn't know if I wanted kids. I felt resentful about being the one to go through pregnancy and take leave - We’re the ones who have to step back and pause. I knew I wanted the bigger career. That was just what I wanted. Now, I'm so grateful I decided to have kids—there's absolutely nothing better.
I thought being an entrepreneur would be a hindrance, like it would be nice to work for the government, take that 18-month mat leave, and go to the park every day. But upon reflection, being an entrepreneur has been a secret weapon in my journey to parenthood. Kev, my husband and co-founder, is more of the creative, in-the-clouds inventor. He’s not the type-A, get-the-day-to-day-tactical-stuff-done person. Knowing we wanted to start a family during COVID, we hired Julia as CEO. She’s amazing and naturally stepped in as interim CEO for both of my mat leaves. I took about four months off for each, and Kev took the eight months of parental leave after mine.
So, we’ve had this flip situation where usually the mom takes more time, but I haven't had to step away for long. Even during those four months off, I chatted with Julia weekly and stayed very in the loop. Six weeks into our first daughter’s life, we aired on Dragon's Den, so we were carting our six-week-old to Toronto for a viewing party.
We’re very passionate about our business, the problem we’re solving, and our team. It doesn’t feel like a chore to integrate work with parenthood. Having a partner who’s flexible, who can take parental leave and understands the demands of entrepreneurship, has been really helpful. I don’t think I would have done well taking a year off, as much as it might sound nice to eat bonbons and go to the park. It’s been really nice to get back into it.
I think what you said really is the big unlock for me: autonomy, which being an entrepreneur certainly gives you. There comes a point where it feels like the career clock and the biological clock get into this weird conflict. That autonomy is missing when you’re on a certain path, working certain hours, and showing up at a certain place at a certain time. Any sort of flexibility is almost held against you because the assumption is that if you’re not fully adhering to this rigid structure, you’re not fully invested
I think even if I wasn't a parent, I would still be on this journey to reject the hustle culture that comes with entrepreneurship and startup life. Ten years ago, it was so in vogue to brag about how much you worked, how little you slept, and how you sacrificed your health and personal life for your business. If you didn’t, you were seen as a bad entrepreneur who didn’t care. But now, we've swung the pendulum the other way, and COVID was a big catalyst for this. We all went remote, and productivity increased in most cases.
At Willful, we’ve created a culture, led by my desire for flexibility, that focuses on output rather than hours spent. We have policies like the ability to work from anywhere. The ethos is: get your stuff done. Be online and available for meetings and collaboration, but otherwise, we care more about accountability than hours logged.
I’m taking my daughter to dance class at 4:30 on Mondays, doing daycare pickups, and I’m not working till five. I’m certainly not working during the chaotic morning rush or toddler dinner hour, which, as you know, is impossible for getting anything done. My journey has been about focusing on high-impact tasks, not working more hours.
How do I get more high-impact things done? How do I focus on the $1,000-an-hour tasks, delegate what I can to my team, or just deprioritize tasks that aren’t moving the company forward? The constraints of parenthood have actually helped me reflect on using my time more valuably and getting more high-impact work done.
100%. There’s this idea that work fills the time you give it, and putting constraints on it actually helps. Another thing I always tell people is to hire more parents. They excel at time management, empathy, and putting someone else’s needs before their own—all essential skills in parenting.
The narrative that parenting is just about constantly cleaning dirty diapers and feeding kids misses so much. These skills should be elevated more so organizations see how valuable parents are and give them the autonomy and flexibility they need.
How can organizations better recognize and leverage the skills that parents bring to the table, and what steps can they take to provide the necessary autonomy and flexibility?
I’ve always considered myself an empathetic leader, but having kids has given me another level of empathy for parents and caregivers. It doesn’t have to be just parents—anyone who has someone relying on them. I absolutely think I’m a better leader and employer now that I’m a parent. I can truly empathize with the demands on people’s time and the need for flexibility. It’s a secret weapon for any organization to have parents in leadership positions because a huge percentage of your workforce will be in that situation.
To your point, there are so many exclusive practices that we follow. I think back to my 20s when I spent most of my time going out to tech events two to four nights a week in Toronto. Now, the hours of 5 to 8 p.m. are sacred for me because that’s when I’m spending time with my kids. That’s dinner time, and I don’t miss that very often.
There aren't as many events now since we’re in Prince Edward County, but most events—whether it’s breakfast meetings or evening events—are catered towards people without caregiving responsibilities. As a tech community, I’d love to see practices, events, and policies that are more inclusive towards caregivers, parents, or even people who just want to relax and recharge in the evenings rather than going out and shaking hands.
Do you feel like there’s been a shift in the tech ecosystem? You’ve been in it for some time, first covering it and now as an entrepreneur. There was a time when the whole "Girlboss" culture and figures like Elon Musk promoting hardcore work ethics made it seem like working in tech meant being unencumbered, living and breathing at the office, with nothing else in your life. That was so ingrained in the DNA of tech that many people wouldn’t even consider joining the ecosystem because they couldn’t rationalize giving so much of themselves to an organization.
Have you seen that shift, or do you feel like you’re still one of the outliers trying to fight the prevailing culture?
I think it depends on the age and stage of the company and the tone set from the top. For example, if your company is just getting off the ground, you’re probably going to put in more time—not because you have to, but because there’s just more to do and fewer people and resources to get it done. The age of the company matters, as does the age of the people. I advise a company where one of the founders is in his early 20s. He’s in that phase of working all the time, not because anyone’s telling him to, but because he’s passionate about solving problems and doesn’t have kids or other obligations.
In contrast, my life now, seven years into Willful, is different. We’re at a stage where we don’t want to work 24/7 because we have lives outside of work, and we’re parents. It’s important to us. But I know startups that are 10 years in and still have a culture of working all the time. Leadership sets the tone. There’s much more attention on mental health now. Studies show that specifically for engineers, the more time they spend coding, the more mistakes they make, and the lower the quality of their code. There’s so much data showing that working 18 hours a day does not increase output. It leads to attrition, burnout, and bad reputations.
At least in Toronto, I’ve seen the tide shift. This shift is closely tied to empathetic leaders, many of them women, who have been vocal about how unacceptable toxic workplace cultures are. We don’t see as many toxic horror stories as we used to because people have realized that if you want to hire and retain talent in 2024, you can’t run a sweatshop that treats people like garbage.
One of the things you started by saying was that you grew up with your mom as the primary breadwinner. You identify as an ambitious, driven woman. And I identify as one too. I always thought ambition meant getting the bigger title, running faster, and working harder.
Then parenting happened, and I realized that a part of me changed. The amount I could invest and the speed at which I could continue running changed. I’m still trying to understand what all this means. Am I still ambitious? Have I completely changed as a human being?
I wonder how you look at yourself now. How would the Erin of her 20s look at you? What are your reflections on this transition in your own life?
I resonate so much with what you are saying! It’s funny because my biggest concern about having children was that it would slow down my success curve and force me to be selfless instead of selfish. Whether it’s deciding what to do on a Saturday or making career choices, I worried that I’d lose that freedom. Now, my reflection is exactly what you said: the number one most important thing in my life is my family. It always was—my mom, my husband—but I would have put Willful up there pretty close. Willful is still extremely important to me, but if you told me I had to live in a shack in the woods and work at the local grocery store, as long as my kids are happy, I’d be fine. My definition of success and happiness has changed.
When I had my first daughter, I took a few months off, and I was so hormonal—it hit me hard. I remember sobbing to Kev one day, saying I couldn’t go back to work, that I needed to leave Willful and be a stay-at-home mom. I couldn’t imagine leaving her. Kev, bless him, was so supportive. He was like, “Okay, okay, I hear you. But what are you going to do when she goes to school in a couple of years?” He was trying to be rational, but I was so emotional. A couple of months later, when the hormones dissipated, I was like, “Oh my God, I need to get my identity back.”
When I think about my life in 15-20 years, my goal is to be to my kids what my mom was to me: a role model with a rich professional life, ambition, and who shows the value of hard work, but always put me first. Even when she was on a plane half the month, or missed my birthday because it coincided with the largest telco conference in the US, she never made me feel like I was a second thought. That’s my version of success: having a rich professional life that doesn’t define me, and using that to set an example for my daughters without being someone who resents them.
I saw this Instagram meme that hit me right in the face: “The only people who remember if you work late are your children.” I don’t want to be that person. I want to be present. I think we’ve set up a culture at Willful, and society with virtual work, where that balance is possible.
I love that both as being a mom to a daughter and being the daughter of a strong independent professionally successful mother! Any final reflections?
One reflection I've had is that the people reading your newsletter, I would guess, are like me and you—type A, organized people. My husband is incredibly helpful; he's an amazing dad and shouldered a lot of the burden during parental leave and such. But as women, there's still this emotional labor that comes with parenting that I don't have a solution for, but I think about it a lot. It's things like making sure there are enough diapers ordered, knowing what gifts to get for birthday parties, preparing Easter baskets—all these details.
So, it's not just balancing parenthood and motherhood; it's also managing the household, and it's a huge project. I wonder if the paradigm shift we'll see in the next 10-20 years is recognizing, celebrating, and offloading some of this emotional and logistical labor that women often take on to run a household with kids.
+1 to that!
So final question, given you do read 40-50 books a year, any recommendations?
I really loved "The Poisonwood Bible" by Barbara Kingsolver. I loved the book "Between Two Kingdoms," a memoir about a woman's battle with leukemia—it sounds depressing, but it's very beautiful. And I also really loved "Bad Blood," which is about the Theranos and Elizabeth Holmes scandal. Three very different books, but each fascinating in its own way.
🤓 Open tabs…
(I have modeled this section after those “open tabs” that we all have with a few (okay 30-40) interesting links that we promise we will eventually get to one day. These are the links that I had open for sometime that I finally got to …)
⭐The Birds and the Wasteland
If you find yourself in a wasteland, you must find a place where you can nourish your soul. You must find a sacred space where you can reconnect with the source of life.
Nobody will walk this path for you….. The answer to a dead culture emerges when you realize how truly and deeply alive you can be.
Then you start walking.
⭐Why Women Can’t Overwork Themselves Out Of Workplace Inequality
In the study, men who clocked 60 hours per week were 8% more likely to receive overwork rewards than women who also clocked 60 hours per week. Although the evaluators tended to rate all overworkers as more committed and more competent than the full-time workers, this ratings boost was significantly larger for overworking men than overworking women.
The evaluators appeared to strongly attribute men’s overwork to greater career commitment. But the boost in perceived commitment was smaller for overworking women due to gender biases about competence. Evaluators appeared to attribute women’s overwork in part to lower competence that required more hours to get the job done.
⭐Are Millennials the Most Nostalgic Generation? (🎧)
No, millennials are not the most nostalgic generation — we’re just in a deeply nostalgic moment in our lives, reckoning (sometimes gracefully, other times less so) with no longer being the Main Character in the generational story.
📖 My private thoughts from my very public diary…
(Sometimes on X (Twitter), sometimes on Threads)
Thank you for reading! Did you know that liking this post or leaving a comment helps it find more readers? More importantly, I would love to hear from you, feedback is always welcome!
And if you happen to know an inspiring working parent who should be featured in a future edition (or if you yourself are one) - please do get in touch
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Disclaimer: All views expressed are my own and do not necessarily reflect the views of my employer