DiscoverCareer Crossroads
Career Crossroads
Claim Ownership

Career Crossroads

Author: Jonathan Collaton

Subscribed: 5Played: 24


Getting to where you want to be in your career is not always as linear as we might think. On Career Crossroads, host Jonathan Collaton talks to one guest each week about the expected and unexpected choices they have made to get where they are in their career today. Starting with the question of 'what did you want to be when you grew up?", they discuss all the jobs they have had, the people that influenced them, and the decisions that led them to their present career. They reflect on how sometimes we have these 'crossroads' moments where we have to pick one thing over another. The episodes are about the guests and their stories.
32 Episodes
#31 – Hailing from the Cayman Islands, Lisa Hylton has always had a career where she crunched numbers, although who she was crunching numbers for has changed dramatically over time. After doing part of her university degree in Cayman, and then transferring to the University of Georgia to complete it, Lisa began her career in accounting with Pricewaterhouse Cooper. After establishing herself at home, she then sought to take her talents abroad via a PwC exchange program. After considering New York and Toronto, Lisa eventually decided on Boston and packed up to move countries once again. It was in there, in Boston, where she really began to shine in her field, but with all this success came sacrifice. Vacations were sparse, so after years of hard work, Lisa finally took an extended tried to the west coast and upon returning, decided that a move was in order. She packed up and transferred to the PwC offices in Los Angeles and continued with the same work ethic she has exhibited in Boston. Years later, Lisa began to wonder what she would command if she tried looking for work outside of her company. This search led to her first major pivot as she became the controller of a real estate investing company. It was while working there that she began to understand the value of real estate and she started doing some research. Now, 2 years later, Lisa is on Career Crossroads to tell her story and make a big announcement about the future of her career path.Lisa can be found at the following locationsWebsite: lisahylton.comInstagram: @lisahylPodcast: The Level Up REIYou can find Career Crossroads at or follow us on social mediaInstagram: @career_crossroadsLinkedIn: Career Crossroads PodcastTwitter: @jcollaton
#30 – Helen Hanison’s has lived a life of two careers. After stumbling a little as a teenager, she attended university at the age of 21 to get a degree in Media and Communications and after spending a term during her degree working at a high-profile Public Relations firm, she was hooked. This experience led to a long career working in PR in increasingly difficult positions, in multiple cities in her native England. Despite her success in the industry, it wasn’t an entirely smooth road. The fast-paced field created a lot of turnover and she had to navigate new supervisors and new firms along the way. Children and a move to New York City put a pause on that career but upon returning to England, she headed back to the frontlines of Public Relations. When things just seemed to not fit anymore, she headed back to school as a mature student to get a Bachelor of Psychology, as it was always the relationships with co-workers and clients that interested her about PR. Now, Helen is a successful Leadership Coach, helping people take the skills they currently have and find a new direction in which they can utilize them to their fullest potential.Helen's Contact InformationWebsite: helenhanison.comSocial Media: @HHanisonHelen’s Complimentary Career Framework:  click here
#29 - James Cridland knew from the time he was a teenager that radio and technology were two of his biggest passions. Given that, he had a fairly easy time deciding where to try and get hired after high school; a radio station. In a weird twist, early on in his career he was fired and rehired by the same person, but he realized that being the on-air talent full time didn’t allow him the creativity he desired. Using his other skillsets, over the next number of years he ran a radio station website, created a media directory, and was involved in the world’s first phone app for a radio station. Then a head-hunter approached him about a job with the BBC and while he took it, it proved to be a terrible decision. Since leaving, James has found his place consulting for radio stations around the world and ventured into the world of podcasting where he now runs Podnews, a daily newsletter and podcast that allows him to utilize both of his passions in tandem. You can find James at the following websites and social media accounts:Podnews Website: Personal Website: james.cridland.netTwitter: @JamesCridland
#28 – Jessica Bondy has always been a natural leader and from a young age she developed a passion for helping others. Towards the end of high school, as she tried to figure out what career path to go down, she flipped open a book about careers and landed on recreation therapist. Everything about the job seemed right so she set off to the University of Waterloo to begin her education. While excelling academically in her undergraduate degrees (she did two of them simultaneously), Jessica became heavily involved in student life, specifically in the area of housing. While she had plans to pursue a full-time Master’s degree once she graduated, a full-time job popped up in Campus Housing and Jessica jumped at the opportunity, thus beginning her career in Student Affairs.  Years later while on maternity leave from another role at the university, Jessica began to feel like she needed to make a change. After testing out many options, she realized that if she wanted to ensure happiness in her future career she needed to get back to her roots and help those in need. As she began to explore the non-profit sector, a crazy turn of events led her to become the Housing Director at House a Friendship in the Waterloo Region of Ontario, Canada; a role she is still in today.Social Links for House of FriendshipWebsite: @hofwatregFacebook: @houseoffriendshipwr  
#27 – Kristy Bernardo is the woman behind the wildly successful blog The Wicked Noodle, however, being a professional foodie wasn’t always in her future. Growing up in small town Wisconsin, Kristy didn’t have s strong sense of what she should pursue after high school although it didn’t take long for her to find out that she excelled in retail. After 5 promotions in 5 months, she was managing her own store in another state by the age of 20! Next came a move to Southern California where she lived for 16 years as she advanced her career through various companies from Payroll Specialist all the way up to Vice President of Human Resources for Wahoo’s Fish Taco. Upon having children, Kristy became a stay-at-home mom who had to learn how to cook, so she thought she might as well blog about it and this, The Wicked Noodle was born. Despite her low expectations, the blog gained a following quickly and within 6 months she was working with advertisers and opportunities were presenting themselves. Now, 12 years later, food blogging has taken Kristy farther than she ever imagined. She’s been a national spokesperson for major brands, worked with famous chefs, hosted TV shows and publish 5 cookbooks – all from a little hobby blog. Listen to her Career Crossroads interview to hear the whole story.Kristy can be found at the following links:Website: www.thewickednoodle.comSocial Media: @thewickednoodleOr look for any of Kristy's cookbooks on Amazon or wherever you buy books:The Big Book of Instant Pot Recipes: 240 Must-Try Dishes for your Multi-Function CookerWeeknight Keto: 75 East and Quick Recipes for Delicious Low-Carb MealsCooking from Frozen in Your Instant Pot: 100 Foolproof Recipes with No ThawingWeeknight Cooking with Your Instant Pot: Simple Family-Friendly Meals Made Better in Half the Time Easy Cooking with Your Ninja Foodi: 75 Recipes for Incredible One-Pot Meals in Half the Time 
#26 – Christine Dainard is in a vastly different place now than she was when she left high school in her teens. After not getting her diploma, she became a top 10 salesperson, nationwide, for a Canadian exercise equipment retailer. It wasn’t because she was really good at convincing people to buy things - Christine was just really good at understanding people’s needs and with her friendly and energetic personality, she was able to find solutions to their problems. After having a child and going through a divorce, Christine was looking for a change and upon evaluating her interests, decided that Public Relations was what she would pursue. After getting a college diploma, Christine put in the work to get a full-time government job that would provide her with the stability she wanted for her and her son, but after many years of hard work, the pressure of the job began to take its toll. As she struggled with what to do about a career she wasn’t happy with, a friend brought Christine to a winery in Norfolk County in Ontario for a relaxing weekend. Christine was awestruck by the tranquility of the area and literally couldn’t stop the words from coming out of her mouth – she was going to start a winery tour business. Five years later, Buzz Tour Company is Christine’s full-time career and she wouldn’t have it any other way.Listen to Christine’s career journey today!Christine's Website: buzztourcompany.caChristine's Social Media: @buzztourco
#25 - Composer, voice actor, sound designer, host. These are some of the words you can use to describe what Lindsay Graham does in his current career as a full-time podcast creator. He's the man behind American History Tellers, American Scandal, Business Movers, and many other hit podcasts that are part of the Wondery network, however, podcasting has really only comprised the last handful of years of Lindsay's career. Prior to that, he worked in insurance sales, marketing, accounting, and a variety of other roles that are not directly related to what he does today. So did he go from those jobs to podcaster? You’ll have to check out his Career Crossroads interview to find out.
#24 – Early in her professional career in India, Priyanka Ojha has moved around a lot. It started when she got her degree in mechanical engineering and was quickly recruited by Bosch to work in their diesel engine pump division. But one year into that career, Priyanka decided to expand her professional credentials and began a Masters of Business Administration in Finance. That led her to jobs in business development and employee engagement before she packed up to move again – this time to Germany where her husband’s career was located. Now working in software consulting for Deloitte, Priyanka has come a long way from where she started her career. Listen to episode 24 of Career Crossroads to hear Priyanka reflet on the career path she has chosen.Social Links for PriyankaPodcast: Social Media: @peoplesstoriespod
#23 – Ivan Lu was driven by respect and competition to follow in his brother’s footsteps in a corporate career. To make that dream a reality he decided to get a degree in Commerce, something that would provide him with a variety of opportunities when he graduated. While in university, his internships/co-op experiences helped him realize that some of what he was studying was just not that interesting. He did not want to sit in a room and crunch numbers so upon graduating he tried to find a job with more of a client-facing role. Bouncing between a couple of jobs, Ivan found himself spending more and more time on one of his hobbies, singing, and soon realized he needed to set off down a totally different career path than the one he initially intended.  Now, two and a half years later Ivan has his own vocal coaching business and is thriving.Website and Podcast: singingsimply.comInstagram: @singingwithivan
#22 – Chris Johnson has an idyllic life working at his own skate shop, Passion Board Shop, in Eau Claire Wisconsin. But when he was 18, life didn’t look like it was heading in that direction. With an interest in sales, Chris decided to study business at the University of Minnesota Duluth but quickly decided the degree was unnecessary. As he had learned working at a Zoomies store in his teens, you just had to be a good salesperson to succeed in sales, and that is what he wanted to do. Chris set out to begin climbing the corporate ladder at Kay Jewellers, Helzberg Diamonds, and eventually landed at Verizon Wireless as an Assistant Manager. Then one day, he looked around and realized he didn’t like the person he was becoming and decide to make a change. How does that lead to opening a skate shop?  Listen to Chris’s interview to find out.Find Chris at the links belowInstagram: @passionpodPodcast/Business Website: 
#21 – Raised in rural Kansas, Scott Mason would look up at the stars at night and dream of two things – disco and the big city! After finishing his undergraduate degree in Minneapolis, Scott was accepted into Columbia Law School and was quickly trying to find his place in New York. Upon realizing that his passion lay more in advocacy work, and not in litigation, he began working for the City of New York. During his 20-year career there he was involved in numerous projects and initiatives that he can be proud of but something wasn’t sitting right, and one day Scott decided to leave his job for the great unknown. While trying to figure out what was next, he began working as a small business consultant which opened up a world of opportunities that directly influence the work he does today. Listen to Scott's interview to hear his entire career journey.Scott’s Websites: and speakerscott.comScott’s Podcast: Purpose HighwayScott’s social media:  @s.scott_mason
#20 – From switching schools in undergrad, to working in the Bahamas, to living in 4 states before she was 30, moving around was never something that held Sarabeth Berk back. She had never been afraid of change, from the moment she decided to shift away from her plan of working with computers in university. Instead, she went in an entirely opposite direction and studied art. Upon graduating, she loved the creativity working as an art teacher gave her and found roles that she enjoyed. At the same time, she had the desire to affect change on a larger scale, which led her to pursue first a Master’s degree, and then a Ph.D.  After working for a private school, a school district, and a foundation working on early childhood initiatives, Sarabeth now finds herself educating people on the value of their career hybridity.  What is career hybridity you might ask?  Listen to Sarabeth’s career journey to find out. You can find Sarabeth at the following locations:Website – www.morethanmytitle.comSocial Media - @morethanmytitle
#19 -   Growing up near London, England, Josh De Luna decided to study law in university, but not because he wanted to become a lawyer. He was busy trying to figure out who he was and how he fit into this world – law just seemed like a fun thing to study along the way that would also appease his parents' wishes. Upon graduating, Josh left for an adventure in Brazil, volunteering for an environmental NGO, but many months later he decided to come home when the lifestyle wasn’t a good fit.  Thus, began Josh’s journey to find out what WAS the right fit. Watching his friend's careers take off, he moved to London and tried a variety of high-powered jobs so he could live the Wolf of Wallstreet lifestyle, but something with always slightly off. At some point, Josh realized that while he was running away from being a lawyer because it was what other people wanted for him, it actually was what he wanted for himself. After working as a bartender, and loving it, during his Master of Law degree, Josh is now in a happy place as a lawyer who lives life on his own terms. You can find Josh's  Personal Instagram here: Josh’s Podcast Instagram: 
#18 - Growing up in Nigeria, Yemi Timson aspired to achieve greatness. Despite her parent's wishes that she become a doctor, she had an interest in accounting and economics and completed a diploma at the University of Jos. While considering further education in accounting, she began to look to the career of Dr. Ngozi Okonjo-Iweala, the Managing Director of the World Bank as a template for what she should aspire to be. A promotional video with jet skis from Eastern Mediterranean University convinced her to do a degree in Cyprus and on her first day she switched into the economics program to follow in the footsteps of Dr. Okonjo-Iweala.  After 4 years in Cyprus, a Master’s degree was in the cards, and Carleton University in Canada was offering a full ride! Three provinces, her first experience with snow, and three jobs later, she is now working as an Economist for the Government of Alberta. Will she ever make it to the World Bank like Dr. Okonjo-Iweala? She hopes!If you want to listen to Yemi's podcasts, you can find Tunuka Media here:’s Instagram and Twitter - @MyPixelJourney
#17 - When leaving high school, Jonathan Miller took the route that many would say leads to success; he went to Wilfrid Laurier University, did co-op, and graduated with a business degree. His co-op secured him a good starter job in Toronto and it seemed like, at 22, he was at the beginning of a long career in marketing.  But just over a year into his career, he took a trip that changed his perspective on what mattered. Upon returning, he quickly realized he wanted more of that adventure and within 4 months he quit his job and bought a one-way ticket to Thailand.  Returning from his second big adventure, he worked his way up in the world of digital marketing, but when he and his partner had the opportunity to sell their house and leave it all behind for adventure number 3, they jumped at the chance. A journey that involved living in a van, philosophy books without answers, and rock climbing across North America, left Jonathan with the urge to build something himself.  Starting as a Communications Coach, he is now a successful Leadership Coach working with social impact founders in South Africa. Check out Jonathan’s story to hear how his career has unfolded.Jonathan's Website: Jonathan's Podcast:  Mindful Communication Podcast. Soon to be renamed The Leadership Gap
#16 – Ania’s career path has taken her many places. When she was in high school she wanted to be a lawyer but a guidance counsellor crushed that dream. When she wanted to go to fashion school in Los Angeles, the almighty dollar crushed THAT dream. After an amazing experience at Conestoga College, she finally settling into a career in business, however, a tragic loss led her to realize there was more to life than work. She began to look for something that would give her a better work-life balance and although she excelled at a career in insurance, it wasn’t a long-term career option for her. As Ania found herself drifting towards something where she could be more creative, she took the plunge and headed back to school as a mature student at Sheridan College for their Interior Design program. After a tense period of trying to land a steady job, she has found her fit at Wilfrid Laurier University while also managing her own design company, a YouTube channel, and a podcast.Link’s to Ania’s projects: Podcast: Youtube: Business: 
#15 – As a kid raised playing ball hockey on the streets of Toronto, Tyler Madarasz always knew he wanted to work in hockey. But when it came time to pick an education pathway to get him to his goal, Tyler wasn’t totally prepared.  He ended up picking a program that was not what he expected and quickly realized he needed to make a change. After getting advice from a family friend, he found his way to the College of Sports Media where he immediately fell in love with the program. During his diploma, he got a placement at SiriusXM NHL Network Radio and knew he found a place he could work long term. However, upon graduating from the college he faced the prospect of working his way up the ranks in small radio stations across the country to get his dream job. Where did Tyler end up? Listen to episode 15 of Career Crossroads to find out!
#14 - While cultures around the world are different, parents are all the same; they want their children to have a good life, and a stable career can help make that happen.  That’s why Sen’s parents recommended that their son, a bright student, should become a doctor.  The world always needs doctors, in good times and bad, so Sen took their advice and ended up as a surgeon in his native China. After a government policy change pushed him away from surgery and into the role of Quality Care Specialist, Sen moved through the ranks until he was the Director of Emergency and of the Patient Department at the hospital where he had done his training. Despite the success, some of the things Sen saw had him considering leaving China for the western world. Looking for a way to move his family to Canada, he found the Master of Public Health program at Western University and knew that was his pathway to immigration. Three and a half years after arriving in Canada, completing his Master’s degree, and working in the Canadian healthcare system, Sen reflects on how he got here. 
#13 - Will Smyth (a.k.a ImperialJedi) didn’t always know he was going to be a Youtuber/Twitch streamer, but he did have ambitions to do something grand or different. Racecar driver? Radio host? He couldn't settle on one thing, so when he had to pick a path out of high school, he decided to attend the University of Guelph. The plan was to work in either law or law enforcement, but an ‘existential crisis’ led to him abandoning that idea. While taking some time off from school, he stumbled upon a YouTube video of someone who had early access to Sim City 2013, the newest version of a game he played when he was younger. Early access? He wanted early access, so he decided to try and make his own YouTube videos with the hope of getting a few free games out of it. After going back to school for Business Administration, a marketing professor heard the passion he had for his YouTube channel and encouraged him to keep growing his online content. Then in 2015 with the release of a new game, Cities: Skylines, Will was hooked.  The day the game released, he created a tutorial video, uploaded it to YouTube, and by the end of the day, it was by far his most popular video. After funding a stable full-time job that allowed him to rebuild his relationship with his father and continue to work on his content, he built up a catalog of quality Cities videos and began to stream on more consistently. After numerous false starts, he finally made the jump to full-time content creator early in 2020, and now instead of getting video games for free, he's getting paid to play video games. Listen to episode 13 of Career Crossroads to hear Will’s story. ImperialJedi Twitch: Jedi Youtube:
#12 - Kait’s journey to her current career took her through a winding road in her late teens and early 20’s.  She tried multiple educational paths and finally settled on fashion as her career of choice.  But the path to being a Merchandising Manager was bumpy, and she turned to a more stable office administration role where she thrived.  With a constant urge to better herself, and with the support of her colleagues and friends, she moved across the country, again, to begin a marketing program at Humber College. Going back to school as she was turning 30, she wanted to have the traditional student experience she had heard about and joined the Humber College First Year Experience program; a decision that proved to be very beneficial to her long term.  After two lectures with her Organizational Behaviour professor, she had a conversation that changed the whole path of her degree.  Listen now to how Kait ended up in a career in Human Resources.
Download from Google Play
Download from App Store