Fireside Chat with Jacob Kojfman
- Prudence
- 10 minutes ago
- 9 min read
August 18, 2026
Men Are from Mars, Women Are from Venus has long been a lighthearted way of explaining why we sometimes see the world differently. Whether or not you subscribe to that idea, becoming a parent certainly has a way of reminding us that no two people approach the job in exactly the same way. We each bring our own personalities, instincts, strengths, and yes, even our own sense of humour. Perhaps that is why dad jokes never seem to go out of style. As comedian Jim Gaffigan has shown us time and again, laughter has a funny way of making even the most chaotic days feel a little lighter.
That sense of humour becomes even more meaningful when we remember how rarely we hear from dads themselves. Their perspective is often tucked quietly behind the scenes, even though fatherhood is filled with its own emotional depth, learning curves, and heartwarming moments. This is why this edition of the Fireside Chat featuring Jacob Kojfman resonated so strongly. Parenting with humour is not about making light of challenges. It is about making room for joy in the middle of them. His stories show that harmony is possible even when life feels like a cosmic balancing act. Parenting is not about finding the perfect approach. It is about showing up, adapting, and discovering what works for your family. Every parent has something different to offer, and sometimes the most meaningful moments are the ones that make us laugh when we least expect them.
As you read this Fireside Chat, I hope you find yourself smiling, reflecting, and perhaps seeing your own journey in Jacob’s stories. His thoughtful perspective is a gentle reminder that building a meaningful legal career and raising a family are not competing goals. They are lifelong journeys shaped by presence, perspective, and the people who matter most.
Without further ado, let’s get started.
P.S. If you are in the mood for a good parenting laugh, Jim Gaffigan always delivers. Check it out:
Part 1 - Introduction
Hi, my name is... Jacob Kojfman.
Year of call to the Bar: 2004 Ontario; 2007 BC; 2016 AB (gave it up).
Type of practice, your role, and where: Senior Legal Counsel, The Co-operators Group Limited. I work on commercial contracts, focusing on technology and professional services.
Part time GIF sharer.
How many children do you have? One human and one fur.
What do you do for self-care or stress relief? Exercise, read.
What would you do for work if you weren’t in the legal profession? My original career path was to be an accountant. If I could choose other careers, a politician or SNL writer.
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?
Jacob: I barely had a ‘pla’, let alone a plan. My original career goal was to be a securities lawyer and become chair of the Ontario Securities Commission. I didn’t summer at a law firm; I didn’t even know what I do now was an option when I was in law school and starting out.
Serendipity and necessity has driven a lot of my career decisions. I took jobs without thinking if it was the right fit for me. I’ve also been fortunate to have opportunities presented to me that I may not have found on my own.
For those starting out, I suggest you identify your values first. It’s easier to make decisions when they align with your values. It is always easier to find a job when you have a job, so even if you take a job that does not align with your values, that job will bring you closer to one that will.
Even if you have a plan, be flexible. Two of the greatest inventions of our time - Post-it Notes and Febreeze - came out entirely by accident. If something comes along and it is not in your plan, don’t dismiss it right away. There are sometimes other benefits that can come out of a new opportunity, whether it is substantive knowledge, developing a soft skill, or a new friendship.
A few things I tell every young lawyer:
Get a mentor, ideally someone outside your place of employ. They can help you navigate issues that come up and point you in the right direction. You don’t know what you don’t know. One of the hardest parts about any workplace is the politics, not the substantive stuff. There’s always lots of resources to learn substantive law.
If there’s a sliver of a notion that you need counselling, you do. When I graduated law school, we didn’t know about imposter syndrome. We didn’t know about the mental health and addiction issues afflicting the profession.
Do new things that are NOT related to the profession: volunteer somewhere you care about; go to a museum; read fiction; etc. in law you’re always dealing with people and people are more than just their jobs.
Take every opportunity you can to learn, especially from more-experienced lawyers. If you work with contracts, read other contracts. Be curious. Ask questions. If you wonder why a clause was drafted a certain way, ask the lawyer who worked on that contract.
Take care of yourself. Eat healthy; drink water; exercise; meditate; socialize; etc. Your career is a marathon not a sprint. The better you take care of yourself the better you can do your job.
Equilawbrium: Please list one soft skill that contributed to where are you now and suggestions on how to cultivate it.
Jacob: Is gratitude a skill? Anytime someone does something nice for me, I send a handwritten thank you card.
One soft skill I’m always working on is communication - how to clearly get my message across in a way that the recipient can understand it and values it.
Equilawbrium: Please list one hard skill that contributed to where are you now and suggestions on how to cultivate it.
Jacob: I’ve been told I’m a really good writer. Writing is a form of communication and a soft skill. Good writing is a technical skill. Knowing when to use fewer words vs. more words to get your point across, create greater clarity is a skill. Don’t use 8 words when you can get the point across in 4; don’t use 4 words when 8 words may save you millions of dollars in litigation fees down the road.
To become a better writer, read. A lot. And different things - novels, plays, memoirs, magazine. If you work with contracts, start reading your company’s/client’s biggest contracts. Then read books on your area of law, and then anything you can get your hands on, especially if not law related.
A collateral benefit to reading novels is that it increases your empathy and compassion, things that can help you communicate better with your clients and generally other people.
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?
Jacob: My child sometimes doesn’t get that my work continues in the summer because her school stops. The harmony is making sure the work gets done - whether starting early because I go see her school performance later in the day, finish work after the play, or doing some work on the weekend to get ahead so I can go to a track meet, etc.
Clients just want the work done. They don’t care when you do it. If you deliver quality work, they’ll give you a lot more slack. It helps that Co-operators emphasizes us as a whole person, more than just the job.
There are a lot of things we ‘outsource’ in my house. We have someone come weekly to clean our place. We have a salad delivery service because making salads is too labour intensive (my wife is a partner in private practice so she has an hourly rate we can compare against). We use a dry cleaner that picks up and delivers. We try to use other services either remotely or close to home where possible, e.g. I pick physiotherapists and RMTs that are within walking distance of home.
Sometimes I ‘habit stack’ - make sure I run multiple errands that are conveniently located to one another.
All of those things - family, work, life, etc. - are all balls in the air. We’re juggling them. Some of those balls are glass, some are plastic and some are those green glass balls full of nerve toxins from the movie “The Rock”. They’re not always the same ball at the same time. Work could one week be that green thing from “The Rock” and your child could be the same the next week. Those are the ones you make sure do not fall down.
A plastic ball falls, you wipe it off. A glass one, you clean up the mess and get a new glass ball. You’re only in real trouble when the green ball falls. That stuff’ll kill you.
Equilawbrium: Having walked the walk, what is the one parenting tip or trick that you wish you’d known?
Jacob: Keep Calm and Carry On. The best thing you can do for your little people is to be there. And to be calm doing it.
Equilawbrium: What is one of your most cherished memories of your children at that age?
Jacob: The sense of pride and excitement she felt the first time she beat me at “Ticket to Ride”. We’d been playing for years and I won every time till her first victory.
Once we were on vacation and in the hotel room, I was dropping ‘f’ bombs because of how poorly I was playing poker, my wife was dropping them at me because I was quite loud and she was on a call. The child lectured us that we’re supposed to be good examples. She’s very precocious. I kept a diary of things she said or did on a daily basis from age 2 until about age 3 that I can refer to.
Part 4 - Achieving Equilawbrium: how to survive & rise from the “Dual 10” Challenges
"You can have it all, whatever your all is. You just cannot have it all all the time at the exact same time." - Jacob Kojfman
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?
Jacob: Finding a career path. I was in private practice when my daughter was born. The firm was having financial troubles. While I was able to find some good in-house roles after that, they were either on a contract or part-time. It was hard to find a really good in-house role in Vancouver. I did find one in Calgary. For just over a year and a half, I worked in a different city than my three year old.
The other challenges are similar to every parent of young children - to spend enough time with them that they can grow to be amazing human beings and spend enough time at work to do your job, and have enough time for self-care.
My advice: whatever you can outsource, outsource. Think bigger picture - someone once told me your child will not care that the laundry was always immediately folded when it came out of the dryer. I was recently on a webinar for dads and the host said that if it is not in the calendar, it does not get done. Put the important things in your calendar - meetings, gym time, kid’s school activities etc.
Just know that there are tradeoffs and think about the juggling balls.
Equilawbrium: What is your take-home message for our readers who are trying to find their “equilawbrium”?
Jacob: Think about the balls. One day work will be those green orbs full of nerve toxin because you’re going on a family vacation the next day; another day, your child will be that green orb.
You can have it all, whatever your all is. You just cannot have it all all the time at the exact same time.
Equilawbrium: What is the one-word encouragement/support that you would want us to remember?
Jacob: Process.
PROCESS
<<End of Fireside Chat with Jacob Kojfman>>
**A MILLION THANKS TO JACOB!!**
<<Jacob's Biography>>
Jacob got a JD/MBA from Osgoode Hall and the Schulich School of Business, instead of following the exciting path to become a chartered accountant because he “was not ready to start working”. He grew up in Toronto, moved to Vancouver, and spent time in Calgary as part of his legal adventures. He is Senior Legal Counsel at Co-operators, a Canadian-only financial services company, after spending almost six years at the Canadian-affiliate of a Canadian-founded global IT services vendor.
He’s an active member in various legal communities and associations, including the Canadian Bar Association, Association of Corporate Counsel, and volunteers on not-for-profit boards. Unlike Groucho Marx, he will be a member of any club that will have him. He loves musical theatre, poker, coaching soccer, Peloton and making pop culture references. He’s also really proud that he creates educational CLEs that are also very entertaining.
Aside from performing stand-up in Las Vegas in October 2022, his other claims to fame are meeting Keanu Reeves, working out with former NBA star Grant Hill, and eating in the same restaurant as former Prime Minister Brian Mulroney.
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.
