Flashback Files

Flashback Files
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Flashback Files is a real, honest look at how confidence, identity, and leadership are built long before job titles or promotions. Instead of pretending everything is perfect, this show goes backward—through childhood, high school, first jobs, first heartbreaks, mistakes, insecurity, and growth—to understand how people become who they are. Hosted by Josh Green, each episode breaks down personal experiences, journal entries, and conversations with others who are still trying to figure out their place in the world. If you’ve ever felt behind, overwhelmed, you'll feel seen here.

  1. 6D AGO

    NCAA Dreams, Exams and Big Decisions (Sara W)

    Sara W is in Grade 12 — and living in the “in-between” stage a lot of students are in right now: exam season, graduation around the corner, working part-time in the restaurant industry, volunteering weekly, and training at an elite level in beach volleyball with Team Ontario. In this conversation, Sara breaks down what her life actually looks like day-to-day, how she handles pressure (on the court and in the classroom), and the process she uses to make big decisions — including keeping options open for post-secondary, scholarships, and potentially playing in the U.S. We also talk about confidence, comparison culture, communication, and why success isn’t about having a perfect plan — it’s about building a process you can trust.

    46 min

  2. FEB 9

    I Started My Career One Month Before COVID — Career Pressure, Identity & Your 20s: Melissa V

    Melissa V is a registered massage therapist in Ontario, Canada who started her career in February 2020 — just weeks before the world shut down. In this episode, Melissa shares how growing up as a creative kid and soccer goalie shaped her self-leadership, communication, and ability to handle pressure. We talk about choosing a career when your first plan doesn’t work out, the “big boss” stress of licensing exams, how COVID reshaped her view of job security and financial stability, and why building identity outside work matters. We also dive into her competitive powerlifting journey — and what consistency, patience, and community have taught her about long-term growth. This episode is for students, recent grads, and young professionals who feel pressure to have everything figured out — and need permission to breathe, adapt, and build a path that actually fits.

    56 min

  3. FEB 2

    Just Keep Swimming: Caitlin on Career Pressure, Pacing, and Becoming a Mom

    In this conversation, Caitlin shares her journey from education to her career in law, discussing the impact of her upbringing, early work experiences, and the challenges of balancing relationships and ambitions. She reflects on her transition from university to college, her experiences in private and municipal law, and the importance of mentorship. As she prepares for motherhood, Caitlin emphasizes the significance of work-life balance and the evolving definition of success in her life.

    59 min

  4. JAN 26

    Unfolding: Finding Your Pace When You Feel Behind

    In this episode of Flashback Files, Andrea shares her journey from being the youngest sibling to becoming a successful occupational therapist. She discusses the influence of her siblings on her personal development, her experiences in school, and the challenges she faced in finding her career path. Andrea reflects on her transition to university, the importance of research, and the decision to pursue a master's degree. She also delves into the nuances of occupational therapy, the significance of building trust with clients, and the emotional challenges of working in healthcare. Throughout the conversation, Andrea emphasizes the importance of balance in life, the normalcy of feeling lost, and the value of authentic connections in professional growth.

    46 min

  5. JAN 19

    Your First Job Is Not “Just” a Job — Lessons From a 30 Year Career At McDonald’s

    In this episode of Flashback Files, I sit down with Cindy — my former McDonald’s boss — who turned a job she was hesitant to keep into a 30-year career. Cindy started as a teenage crew member, went to College for a correctional officer program, and thought McDonald’s would just be a paycheck on the way to something else. Instead, she moved from crew to store manager, regional consultant, national operations consultant, and now business consultant, earning top awards along the way, including the Global Ray Kroc Award (top 1% of managers worldwide). Together, Cindy and I talk about: • Growing up in a strict, structured house with six sisters and how that shaped her work ethic • Low self-esteem as a teen, but high confidence at work — and why work became her safe place • Why she walked away from her college path and came back to McDonald’s • The suspension I got as a young crew member and how that tough call changed me • Why feedback is a gift (even when it stings) and how to use it to get better • What Cindy sees in young workers today: strengths, blind spots, and professionalism red flags • How to keep your career feeling fresh, even if you stay in one company for years If you’re in your late teens or early twenties, juggling school and a “just a part-time job,” this conversation will challenge how you think about early work, confidence, and the habits you’re building now. Flashback Files is for students, recent grads, and young professionals who want to reflect on how early experiences shape confidence, identity, and leadership.

    51 min
  6. The Pressure To "Pick A Lane" Is Lying To You

    JAN 12

    The Pressure To "Pick A Lane" Is Lying To You

    In this episode of Flashback Files, I have chat with my lifelong friend Tom, exploring how our early experiences shaped our identities and careers. Tom shares insights on balancing various aspects of life, the importance of imagination, and the lessons learned from sports and academics. He reflects on his journey through different industries, the significance of mentorship, and the value of transferable skills. The discussion emphasizes the importance of enjoying the journey rather than fixating on the destination, providing valuable advice for young adults navigating their career paths.

    58 min

  7. JAN 5

    It's Okay To Not Know: Tori T Explores Career Clarity, Confidence and Pivoting In Her 20s

    In this episode of Flashback Files, I sit down with Tori T to unpack what early career confidence really looks like — and how career clarity can evolve over time. Tori shares how she became a shift manager at 16, what she learned managing older coworkers, and how COVID disrupted her post-secondary experience and momentum. We also talk about the pressure to “have it all figured out,” the reality of pivoting when your plan changes, and the difference between looking confident and actually feeling confident. If you’re in your late teens or early 20s and you feel unsure, behind, or stuck, this one will land. Topics we cover: early leadership, lessons from motherhood, career pivots, confidence, post-secondary pressure, mentorship and support systems, and building a path that fits who you’re becoming.

    39 min

  8. 12/31/2025

    2025: EXPLORING THEMES FROM FLASHBACK FILES

    In this episode, I reflect on their journey of creating a podcast focused on early adulthood, sharing personal experiences and insights gained from guests. We will also take a look at universal themes that came up across all guests and I. These themes include self-awareness, confidence, financial literacy, and the universal challenges faced by young adults.

    11 min
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About

Flashback Files is a real, honest look at how confidence, identity, and leadership are built long before job titles or promotions. Instead of pretending everything is perfect, this show goes backward—through childhood, high school, first jobs, first heartbreaks, mistakes, insecurity, and growth—to understand how people become who they are. Hosted by Josh Green, each episode breaks down personal experiences, journal entries, and conversations with others who are still trying to figure out their place in the world. If you’ve ever felt behind, overwhelmed, you'll feel seen here.

Information

  • Creator
    Flashback Files
  • Years Active
    2025 - 2026
  • Episodes
    19
  • Rating
    Clean
  • Copyright
    © Flashback Files
  • Show Website
    Flashback Files