Episodes

Dec. 20, 2023

The End of Career Crossroads

All good things must come to an end. It's been a wonderful journey over the last 3+ years but today marks the end of Career Crossroads. In this final episode of the podcast, I discuss why I'm saying goodbye and …

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Dec. 13, 2023

Mike Fernandes - Leaving his YouTube Career Behind for a shot at Stud…

#100 - Like most kids, Mike developed his musical tastes as a teenager. He liked a wide range of bands and one day decided to try and mash up a couple of his favorite songs and publish the mix on …

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Dec. 4, 2023

Career Coach Conversations with Betty Xie

#99 – As Betty Xie headed toward post-secondary education, she had a plan: study math because that would lead her to a good job. The closer she got to starting classes, the more she realized that while that was practical …

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Oct. 20, 2023

Matt Cooksey – How A Breakdown Led Him To The Perfect Career

#98 - Matt Cooksey ended up in his first career because he was following a family member's footsteps, and it took him almost a decade to realize he wasn't happy. He was always chasing something - more money or a …

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Aug. 16, 2023

Stephanie Chan - Leaving Law Behind to Help the Elderly

#97 - Getting a law degree and passing the bar is quite the task, so it's not often people go through all that work only to leave their law career behind. That's what makes Stephanie Chan such an anomaly - …

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July 31, 2023

Mike Gallagher – Taking his Creativity from Film to the World of Mark…

#96 - As Mike Gallagher spent his teenage years filming his friends skateboarding around the Metro Vancouver area, someone took notice. A high school teacher recognized Mike’s aptitude for film and developed an independent st...

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July 17, 2023

Collision Conference 2023 Roundup - Chatting with Tech Founders Who C…

#95 – When you go to a tech conference like Collision, you might expect that all the founders attending to showcase their companies have deep roots in the tech industry, My experience at Collision, however, shows me that is n...

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July 10, 2023

Kelvin Beachum - NFL Offensive Lineman and Investor

#94 - This week’s guest on Career Crossroads is Kelvin Beachum, a professional football player who plays left tackle for the Arizona Cardinals of the National Football League. As an 11-season veteran who has played in over 15...

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July 3, 2023

Academic Crossroads with Sam Demma

#93 – When Sam Demma started his undergraduate degree at the University of Toronto Scarborough it didn’t take long for him to realize that while he might be in the right place, he was there at the wrong time. Had …

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June 26, 2023

Career Coach Conversations with Soma Ghosh

#92 - When clients come to Soma Ghosh to help them with their careers, they often want support in getting out of an untenable situation. As a Career Coach Soma can certainly help them move to a new job but …

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June 19, 2023

Dan Chan – From PayPal Mafia to Magician for Millionaires

#91 – Every good magician has a stage name and Dan Chan is known as ‘The Millionaire’s Mentalist’. He has earned that name after a career of performing at events for wealthy tech moguls from companies like Twitter and Amazon …

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June 5, 2023

Chronicling Career Crossroads - New Format Success and Fighting Burno…

#90 – Today’s episode of the podcast isn’t an interview- it’s just you and me talking. Now that we’re two months into the new show format, I wanted to give an update on how things are going and let you …

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May 29, 2023

Academic Crossroads with Ben Brown

#89 – As a first-year offensive lineman on the University of Waterloo’s varsity football team, Ben Brown was supposed to be living his dream. With the support of his father, who had been his football coach, Ben received a foo...

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May 22, 2023

Career Coach Conversations with Chris M. Wilson

When you know you want to change your career but you are unsure of where to go, you might seek the help of a professional. Chris M. Wilson, this week's guest, struggled to find the help he was looking for …

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May 15, 2023

CC Shorts with Andy Thibodeau

#87 - What's would you do if your ability to do your job disappeared overnight? How would you react? That's a question Andy Thibodeau wrestled with in March 2020 when Covid-19 shut down his career as a public speaker. As …

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May 8, 2023

Josh Green – From Acting, to Cookie Dough Connoisseur, to Business Co…

#86 -If you told 20-year-old Josh Green that he was going to be a business consultant in the future, he would have thought you were joking. How did he end up a business consultant when he was well on his …

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May 1, 2023

Academic Crossroads with Frank Chen

85 - Attending university can change your life. Sometimes, in ways you don’t expect. For Frank Chen, coming to Canada from his native China to study at the University of Toronto Scarborough (UTSC) was a way to get into a …

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April 24, 2023

Career Coach Conversations with Wei Huang

#85 – “What can I do with my degree?” This is one of the most common questions asked by students who have nearly finished pouring their blood, sweat, and tears into completing a difficult academic program and are now realizin...

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April 17, 2023

CC Shorts with Brian Millado

#83 - In the early days of his career, Brian Millado jumped between jobs in the Department of Student Life at the University of Toronto. He wasn't jumping because he didn't like his roles, or because he was chasing higher …

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April 10, 2023

Chris Lewarne – From New York City corporate lawyer to Barry’s Bootca…

#82 – Chris Lawarne is well known in the Toronto fitness community as one of the trainers at Barry’s Bootcamp, helping people achieve their fitness and health goals. Fitness, however, was not the path Chris set out on when le...

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April 3, 2023

Chronicling Career Crossroads #5 - Where We Stand

Today, we get vulnerable. In this short and final episode of the chronicles series, we cap we discuss what new episode formats are on the horizon and talk about how this series has driven forward Jonathan's public speaking wo...

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March 22, 2023

Chronicling Career Crossroads #4 - Marketing

When products change, their marketing has to change: that's the core of the fourth episode of the Chronicling Career Crossroad series. But how to market something that is still in flux? It's not a question I can answer on my …

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March 7, 2023

Chronicling Career Crossroads #3 - Content

Content is king. You've probably heard or read that phrase over the last decade with the rise of online content creators, but the origins of the phrase can be traced to magazine editing in the 1970s. What does that have …

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Feb. 23, 2023

Chronicling Career Crossroads #2 – Research

When this episode was first conceived it was titled “Research – or how to make sure what I’m doing isn’t a waste of time”. As the episode title was….simplified, the core idea for the episode stayed the same: research. In …

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