Career Crossroads – Details, episodes & analysis
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Career Crossroads
Jonathan Collaton
Frequency: 1 episode/12d. Total Eps: 101

Getting to where you want to be in your career is not always as linear as we might think. Not everyone picks one career path and sticks to it for the rest of their lives, and lots of people are confused about what they want out of their career.
Career Crossroads is on a mission to help people realize that being confused is okay - it happens to more people than you think! Host Jonathan Collaton talks to people with winding career paths, hears about the best advice career counsellors and career coaches and guidance counsellors give their clients and students, and talks to students who have changed their trajectory by modifying their academic plans.
If you're stuck at a crossroads or work with people who are struggling with their own crossroads, this podcast is for you.
Recent rankings
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Apple Podcasts
🇨🇦 Canada - careers
24/07/2025#70
Spotify
No recent rankings available
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See all- https://podnews.net
593 shares
- https://simpler.media/
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- https://taplink.cc/tunukamedia
117 shares
RSS feed quality and score
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See allScore global : 79%
Publication history
Monthly episode publishing history over the past years.
The End of Career Crossroads
Episode 101
mercredi 20 décembre 2023 • Duration 07:06
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 thank those who have helped me make it this far.
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You can find Career Crossroads at careercrossroads.ca or follow us on social media:
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
TikTok: @jonathancollaton
Mike Fernandes - Leaving his YouTube Career Behind for a shot at Student Affairs
Episode 100
mercredi 13 décembre 2023 • Duration 01:04:17
#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 YouTube. That simple action had a much bigger impact than Mike ever could have predicted. It was the first step in launching his YouTube channel which at its peak had over 325,000 subscribers and was getting up to 2 million views per month.
In this interview, we talk through Mike's early career plans that led him to university, the ride of his YouTube channel, and why he left it behind to begin a career in Student Affairs.
Find Mike's YouTube channel at youtube.com/@MagikMikeOFFICIAL
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You can find Career Crossroads at careercrossroads.ca or follow us on social media:
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
TikTok: @jonathancollaton
Dan Chan – From PayPal Mafia to Magician for Millionaires
Episode 91
lundi 19 juin 2023 • Duration 49:38
#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 but when he was first starting out he was making balloon animals at children’s birthday parties.
That’s because magic was not Dan’s first full-time job. After getting a degree in Finance from the University of California, Riverside, Dan was hired as one of the early employees at PayPal – before the merger with Elon Musk’s X.com – and Dan worked his way up from Customer Service to the Finance department. After 13 months, Dan’s path split dramatically from members of the ‘PayPal Mafia’ who went on to found companies like YouTube, LinkedIn, Yelp, SpaceX, and Tesla. Instead of staying in the world of tech, Dan committed himself to magic full-time and now, 20+ years later, he reflects on his career journey on Career Crossroads.
Mentioned in this episode:
- Danchanmagic.com
- Millionairesmentalist.com
- Follow Dan on Instagram @danchanmagic
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You can find Career Crossroads at careercrossroads.ca or follow us on social media:
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
TikTok: @jonathancollaton
Introducing Career Crossroads
mercredi 9 septembre 2020 • Duration 07:56
In this 8 minute introductory episode, host Jonathan Collaton explains what Career Crossroads is all about. He explains where the concept came from, what the show's format is, and his personal rationale for creating the podcast. This is the best place to start listening to find out if the show is for you!
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You can find Career Crossroads at careercrossroadspodcast.com or follow us on social media
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
Twitter: @jcollaton
TikTok: @jonathancollaton
___________________
You can find Career Crossroads at careercrossroads.ca or follow us on social media:
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
TikTok: @jonathancollaton
Chronicling Career Crossroads - New Format Success and Fighting Burnout
Episode 90
lundi 5 juin 2023 • Duration 10:18
#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 know about the podcast’s record-breaking month of May.
I also want to talk a bit about the importance of preplanning to take time off and my own experience with it. The best month in the history of the podcast came during the month I was paying the least attention.
Take a listen and let me know what you think.
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You can find Career Crossroads at careercrossroads.ca or follow us on social media:
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
TikTok: @jonathancollaton
Academic Crossroads with Ben Brown
Episode 89
lundi 29 mai 2023 • Duration 24:59
#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 football scholarship to an excellent school and was excited for the next chapter of his life. Before Ben’s university career began, however, tragedy struck as Ben’s father passed away. Suddenly, Ben was carrying the weight of his and his father's dream all on his own.
Despite this incredible hardship, Ben pressed on and outwardly, had a successful first year of university. His grades were good and he seemed to be happy, but internally Ben was struggling. He decided that he needed to step away from the football team and take a term off school for his mental health and when he came back, it did not take long to realize he no longer saw a future in his program of study.
With the help of a career counsellor at the university, Ben found a new path in an unexpected place that involved leaving the university behind. Now, years after graduating from Conestoga College, Ben is living a new dream as a firefighter.
Listen to Ben's Academic Crossroads today to hear the whole story.
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You can find Career Crossroads at careercrossroads.ca or follow us on social media:
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
TikTok: @jonathancollaton
Career Coach Conversations with Chris M. Wilson
Episode 88
lundi 22 mai 2023 • Duration 28:54
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 and that challenge led him to dedicate his life to helping people going through similar struggles.
As a career coach, Chris helps people find clarity in what they really want because without that you can't move forward. Before we talk about that, Chris walks me through the early part of his career as a helicopter pilot and mechanic and why he felt he needed to move on from that field.
Find Chris on social media and YouTube at @iamchrismwilson
___________________
You can find Career Crossroads at careercrossroads.ca or follow us on social media:
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
TikTok: @jonathancollaton
CC Shorts with Andy Thibodeau
Episode 87
lundi 15 mai 2023 • Duration 31:15
#87 - What 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 a 25+ year veteran of the industry, this was the only job Andy had ever really known and in the span of 48 hours, 31 bookings cancelled and his ability to make an income evaporated.
As Andy struggled with this new reality and the recognition that he was a people person who could no longer be around people, he visited a friend one last time before we headed into lockdown. Something that friend said gave him the mental slap he needed to act and less than 5 days later Andy had a new job lined up to provide him with both the income he needed and the interaction with others that he craved.
Hear about Andy's career crossroad on this week's CC Shorts episode.
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You can find Career Crossroads at careercrossroads.ca or follow us on social media:
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
TikTok: @jonathancollaton
Josh Green – From Acting, to Cookie Dough Connoisseur, to Business Consulting
Episode 86
lundi 8 mai 2023 • Duration 01:02:42
#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 way to a successful career as an actor and improv comedian? He was getting regular work, making more money than most actors he knew, and even had scenes in movies with Ice Cube and Danny Glover.
As 20-year-old Josh would soon find out, the way you feel today may not be the way you feel tomorrow, and when that happens you need to know what else interests you. It took years of travel and teaching abroad for Josh to realize that he wanted to be his own boss, and the best way for him to do that was to run his own company. Moving back to his hometown of Vancouver, British Columbia, Canada, Josh set to work on making that a reality.
This is the story of how over the past 12 years....
- Josh went back to school as a mature student to obtain a Bachelor of Business Administration (his second degree)
- Created, sold, and/or shut down many successful (and sometimes unsuccessful) businesses from a wake park to dog walking to cookie cough and beyond
- Ultimately, realized his passion is in helping other people through the process of navigating the difficult world of taking an idea for a business and turning it into something real
Everyone has a story to tell. Listen today to hear Josh's.
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Links from the episode:
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You can find Career Crossroads at careercrossroads.ca or follow us on social media:
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
TikTok: @jonathancollaton
Academic Crossroads with Frank Chen
Episode 85
lundi 1 mai 2023 • Duration 37:26
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 stable career, while also making his parents proud. To satisfy both desires, Frank chose to study accounting and he was successful in his studies.
During one of his co-op terms, however, Frank came to the realization that he wasn’t passionate about accounting. When he shared this knowledge with a colleague who was also from the co-op program at UTSC, Frank was informed he wasn’t the only one who felt that way. The more they conversed, the more they realized that a lack of love for accounting wasn't the only thing they had in common. Both of them were interested in entrepreneurship and it didn’t take long for Frank and his colleague to decide they were going to start their own company.
That is how Frank, a university student, became the co-founder of Sumer, a grocery delivery service in Toronto, Ontario, Canada. From the challenges of running a startup as a university student, to the difficult decision to shut it down in 2022, Frank and I talk through what he learned from his Sumer experience and how he is applying those lessons today.
More importantly, Frank and I discuss how accepting that he lacked passion for what he chose to study taught him a lesson that has influenced every decision he’s made since then.
Links from this episode:
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You can find Career Crossroads at careercrossroads.ca or follow us on social media:
Instagram: @career_crossroads
LinkedIn: Career Crossroads Podcast
Facebook: Career Crossroads Podcast
TikTok: @jonathancollaton








