Fireside Chat with Jennifer Goodstadt
- Prudence
- 6 days ago
- 8 min read
January 1, 2026
Happy New Year! I’m so delighted to begin 2026 by sharing this Fireside Chat with our extraordinary guest, Jennifer Goodstadt. Jenn is a seasoned lawyer, a deeply respected colleague on our sister team, and someone whose presence would leave a lasting imprint on me.
We first met a few months ago during our onsite team meeting, hiking along the Smokey Hollow Waterfall trail. Picture a breathtaking fall backdrop, leaves swirling, cliffs looming, and me clinging to the edge for dear life, questioning every footwear decision I’d ever made. Somewhere between my panicked scrambling and Jenn’s steady, grounded stride, we fell into one of the most open, honest, and unexpectedly soul‑warming conversations I have ever had with a colleague. In that moment, in between me trying not to slip and her radiating calm, I knew she was someone special. So when I later asked if she’d join this Fireside Chat series, she said yes without a moment’s hesitation.
What stayed with me from that day wasn’t just her wisdom, but the warmth behind it. Jenn carries a quiet hopefulness, a calm strength, and a generosity of spirit that feels especially meaningful to me after a year as challenging as 2025. Maybe it’s the parallel in our lives: she’s a mother of four daughters, and I grew up in a family of four girls. Maybe it’s the way she embodies the kind of steady resilience you see in strong female leads on legal dramas. Or maybe it’s simply that she is one of the most genuine, supportive colleagues I have had the privilege to know.
As we step into this new year together, I can’t imagine a better voice to help set the tone. Jenn’s story is one of courage, adaptability, and redefining success with intention and heart. It is a reminder that work‑life harmony is not a finish line, but something we continually shape as our lives evolve.
To all of you, especially the working parents who are juggling, striving, and showing up in a thousand unseen ways, I hope this conversation offers a spark of encouragement as we begin 2026. Here’s to finding our own version of Equilawbrium this year: with more hope, more compassion, and a little more grace for ourselves along the way.
Without further ado, let’s get started!
Part 1 - Introduction
Hi, my name is... Jennifer Goodstadt.
Year of call to the Bar: 2001.
Type of practice, your role, and where: I am in-house legal counsel at Co-operators.
How many children do you have? 4 children (all girls!) ages 22, 21, 18, and 16.
What do you do for self-care or stress relief? Starbucks and hang out with all my pets! My dog, Stella, and my 4 cats.
What would you do for work if you weren’t in the legal profession? Something with dogs or cats – I would love to establish and operate an animal shelter.
Part 2 - The first “Dual 10” Challenge: within the first 10 years post-license
Equilawbrium: Did you have a master plan for your career path? What was the driving force behind your career decisions? What are the important things to consider as you are figuring out your career path?
Jenn: I had a general plan for sure, but it evolved over time. I knew I’d like to practice at a full service law firm early in my career and gain a solid set of foundational legal skills, preferably in the area of financial services law. I was grateful to join an amazing team at Blakes in Toronto upon my call to the bar in 2001 where I was able to begin to build those skills. I left that role to pursue an opportunity in-house with RBC where I was fortunate to join another incredible team of professionals and continue to develop my skills. There, I also found the flexibility I was looking for as I thought ahead to starting a family. Within my RBC team, I was able to move to a part-time role after my first maternity leave and later to a job-share arrangement, both of which were perfect for the work-life balance I was seeking at the time. Not the preferred options for everyone for sure, but they aligned with my vision for how I felt I could best design a work-life balance that worked for me.
The driving force behind my career decisions has been how I could best manage my involvement in the profession and my role as a parent. I wanted to ensure I had room for both – not both to the same degree at all times, but a shifting balance of both over the course of my career. I think for others considering their own career direction, it’s important to assess and define what that balance looks like, because it’s different for everyone. But once you’ve at least defined what it looks like for you, you can start to seek out paths and options to allow you to achieve it.
Equilawbrium: Please list one soft skill that contributed to where are you now and suggestions on how to cultivate it.
Jenn: I think adaptability, flexibility and a positive attitude (that’s not one, but I think they’re all important!). As someone who has sought out flexible or reduced work arrangements early in my career, I have ensured that I have been both grateful and adaptable to options that have been made available to me. I appreciate the flexibility that others have afforded and continue to afford me and I am always looking for ways to pay that forward, so to speak, with others.
Equilawbrium: Please list one hard skill that contributed to where are you now and suggestions on how to cultivate it.
Jenn: Writing skills! Not just traditional legal writing skills, but being able to communicate your ideas to non-legal audiences, in my case, internal business clients. I have been fortunate to have worked with other lawyers who are clear and concise writers and that has helped shape my writing. Be open to feedback and continuous improvement – there’s always something new to learn!
Part 3 - The second “Dual 10” Challenge: have kids in their first 10 formative years
Equilawbrium: How did you juggle work/life responsibilities? Is it possible to have a family life and a work life simultaneously and harmoniously?
Jenn: I think the juggle will look different for everyone, but for me, I chose to manage my work/life responsibilities by moving from full-time to part-time work, hiring a part-time nanny and generally lowering my expectations across the board 😊. For me, this combination allowed me to achieve a harmonious balance of both – it was still hectic and busy and, at times, exhausting, but on the whole, it was manageable.
In my case, I was fortunate to have had a very supportive manager at RBC (who herself had 4 children) who approved my request for a part-time (3 days per week) position after the birth of my first child. Later, after the birth of my third child, I was able to move to a job-share arrangement with another lawyer (who also had a young family). I would work 2 days and she would work 3 days one week and then I would work 3 days and she would work 2 days the following week.
After the birth of my 4th child, I decided to resign from my position. At that time, I had a 1, 3, 5 and 7 year old and my husband had an opportunity to work in the US. I was able to stay at home with the girls full-time for 6 years and I began considering returning to the workplace when my youngest daughter started Grade 1. In 2017, I was offered the role of senior counsel at Co-operators with another wonderful team of lawyers. Despite having no background in insurance law, my manager was willing to provide mentorship and guidance, and I remain eternally grateful to him to this day for providing me with that opportunity.
Equilawbrium: Having walked the walk, what is the one parenting tip or trick that you wish you’d known?
Jenn: Let perfection go. Doing YOUR best is THE best! Try not to focus on balls that get dropped or things you don’t have time for. Focus on finding the joy (and humour!) in the chaos and celebrating the things that you are doing well.
Equilawbrium: What is your fondest memory of your kids at this age?
Jenn: When I was at home full-time with 4 young daughters, we were a busy bunch, with school drop offs and activities. I have fond memories of loading everyone into the minivan with backpacks, dance bags, skating bags and snacks and getting everyone buckled into car seats and booster seats and then seeing their 4 little faces when I’d look in the rear-view mirror as we’d set off. Those days were busy and long, but yet somehow all but 1 are now off at university!! Where DID that time go??
Part 4 - Achieving Equilawbrium: how to survive & rise from the “Dual 10” Challenges
"Let perfection go. Doing YOUR best is THE best! Try not to focus on balls that get dropped or things you don’t have time for. Focus on finding the joy (and humour!) in the chaos and celebrating the things that you are doing well." – Jennifer Goodstadt
Equilawbrium: What was your biggest challenge going through the Dual 10 phase? Any advice for our readers who are living and breathing this phase and trying to survive and excel?
Jenn: It’s sometimes hard not to be overwhelmed and feel like you’re failing at all the things. There will be those days. The challenge is to keep perspective. Allow some balls to drop, forgive yourself for things that get missed or don’t go as planned. Keep trying different strategies to help you manage schedules and demands and don’t be discouraged if something doesn’t work. Try something else. Just keep trying and keep believing in yourself and giving yourself credit for all that you’re managing and all the effort you’re putting in. If you can outsource some household tasks, absolutely do it. Use any supports, family or otherwise, that are offered. If a part-time or job-share arrangement might work for your situation, ask for it.
Equilawbrium: What is your take-home message for our readers who are trying to find their “equilawbrium”?
Jenn: Equilawbrium will be different for everyone. Try to be guided less by others’ choices of what equilawbrium looks like for them and instead unapologetically define what it looks like for you. If, for you, it means a reduced hours arrangement, either on a temporary or permanent basis, or a few years away from the profession while your children are young, seek that arrangement out. My career is evidence that, within the profession, you can work part-time or take a break from your career if that is right for you and still later return to a robust and meaningful full-time role!
Equilawbrium: What is the one-word encouragement/support that you would want us to remember?
Jenn: Flexibility.
<<End of Fireside Chat with Jennifer Goodstadt>>
**A MILLION THANKS TO JENN!!**
<<Jennifer's Biography>>
Jennifer graduated from Osgoode Hall Law School in 1999 and was called to the Bar in Ontario in 2001. She practised financial services and banking law for 10 years, first as an associate at Blakes and then as in-house counsel at RBC, followed by 6 years in semi-retirement as a full-time mom. She joined Co-operators in 2017 as Senior Counsel where she provides regulatory advice and contracting support primarily for the life insurance business.
Disclaimer: Any views, information, and personal opinions expressed by the authors or guests are entirely their own and do not reflect or represent those of their employers or clients.