Careers & Coffee Talk

Laura Edwards
  • 5.0 (14)
  • Careers
  • Updated Weekly

Welcome to Careers & Coffee Talk — where real people spill the beans about their real career journeys, one cup at a time. ☕ We’re here for the twists, turns, fresh starts, and all the moments in between that shape us. These are quick, casual coffee chats with people figuring it out as they go — just like the rest of us. Because the best stories (and the best advice) are always better over coffee.

  1. Building the World's Longest Resume to Find the Right Career with Gabriel DeSanti

    Apr 29

    Building the World's Longest Resume to Find the Right Career with Gabriel DeSanti

    In this episode, I’m joined by Gabriel DeSanti, co-founder of Staj and creator of what’s been described as the “world’s longest resume.” By trying jobs across industries and sharing those experiences with a broad audience, Gabriel offers a different perspective on how people can approach career decisions. We discuss the pressure to choose a single path, the gap between expectation and reality in many roles, and how individuals can explore new opportunities without leaving their current jobs. This episode is Part 2 of a 2-part series and builds on the conversation with Alex Dworsky in the previous episode.

    34 min
  2. Stuck in Your Career? How to Actually Figure Out What You Want to Do with Alex Dworksy

    Apr 20

    Stuck in Your Career? How to Actually Figure Out What You Want to Do with Alex Dworksy

    In this episode, I’m joined by Alex Dworsky, founder of Staj. After building her career in corporate America, Alex recognized a gap in how people make career decisions, often choosing paths without ever seeing what those roles actually look like in practice. She went on to found Staj, a job-shadowing platform designed to make career exploration more accessible through hands-on experience and real conversations. We discuss why so many people feel stuck in their careers, what’s missing from traditional career advice, and how to explore new opportunities with more clarity and confidence. 🔗 https://www.gostaj.com 📲 https://www.instagram.com/go_staj/

    39 min
  3. Inside the Chief of Staff Role: Maggie Olson on Leadership, Influence, and Impact

    Apr 11

    Inside the Chief of Staff Role: Maggie Olson on Leadership, Influence, and Impact

    What does a Chief of Staff actually do? And how do you actually become one? In this episode of Careers & Coffee Talk, I sit down with Maggie Olson, Founder of Nova Chief of Staff, to explore one of the most in-demand and often misunderstood leadership roles in business. Drawing on more than 20 years of experience across retail, technology, and operations, Maggie shares how she built the Chief of Staff function from the ground up, supporting senior leadership and helping drive alignment across a large, complex organization. In this conversation, you’ll learn: ☕️ What the Chief of Staff role really looks like in practice ☕️ How to build trust and influence at the executive level ☕️ The skills needed to succeed as a strategic operator ☕️ Why the Chief of Staff career path is growing across industries ☕️ How Nova Chief of Staff is helping shape the future of the role Whether you’re exploring a Chief of Staff career path, stepping into a leadership role, or looking to better understand how organizations operate at the executive level, this episode offers practical insight and real-world perspective.

    35 min
  4. Women in Finance and Building a Life on Your Own Terms with Urmi Hossain

    Mar 16

    Women in Finance and Building a Life on Your Own Terms with Urmi Hossain

    The finance world has a stereotype: the “finance bro.” But what about the women building careers in that same industry and redefining what success looks like? In this episode of Careers & Coffee Talk, I sit down with Urmi Hossain — finance professional, author, speaker, and host of the Stories Beyond Borders podcast. Urmi works in the financial services industry, and she has built a platform focused on women’s empowerment, identity, and self-leadership. Growing up as a Bengali woman in Italy, Urmi navigated life between cultures while searching for belonging. Those experiences shaped her journey and ultimately led her to write the book Discovering Your Identity: A Rebirth from Interracial Struggle. Urmi began building meaningful work alongside her career, using her hours outside the office to mentor women, host conversations about identity and migration, and advocate for financial independence and leadership. In this conversation, we explore: ☕ What it takes to succeed as a woman in finance ☕ How identity shapes confidence and leadership ☕ Turning your free time into purpose and impact ☕ Navigating career pivots without burning everything down ☕ Why self-leadership and financial independence matter more than ever If you’ve ever felt like you didn’t fully fit the mold in your career, this episode is for you. Links from the episode: Women in Leadership https://www.womeninleadership.ca/ Urmi Hossain on LinkedIn https://www.linkedin.com/in/urmihossain/ Stories Beyond Border Podcast https://podcasts.apple.com/us/podcast/stories-beyond-borders/id1831413373 and https://open.spotify.com/show/2vbwcrVNedmvljLnT5UEPc?si=34e2e613ba454865 Discovering Your Identity: A Rebirth From Interracial Struggle by Urmi Hossain https://amzn.to/4ltIcvr

    41 min
  5. From Flight Medic to National Leadership: Nitin Natarajan on Saying Yes to the Career You Didn’t Plan

    Feb 16

    From Flight Medic to National Leadership: Nitin Natarajan on Saying Yes to the Career You Didn’t Plan

    What if the career you end up loving isn’t the one you set out to build? Nitin Natarajan thought he’d spend his life in emergency medicine. Instead, his path took him from flight paramedic to hospital administrator, to national security policymaker, to Deputy Director of the Cybersecurity and Infrastructure Security Agency (CISA). In this episode of Careers & Coffee Talk, Nitin shares the pivotal moments that shaped his journey — including getting “kicked out” of college, leaving a stable corporate job for a $7-an-hour EMT role, responding to disasters, navigating imposter syndrome in rooms full of Ivy League credentials, and learning to lead in fields where he wasn’t the technical expert. Throughout his career, one principle has guided his decisions: do right by the people, and make sure everyone goes home at the end of the day. We talk about: ☕ Why saying “yes” can open doors you never imagined ☕ The transition from frontline response to national policy leadership ☕ Leading teams without pretending to be the expert ☕ Imposter syndrome, even at the highest levels ☕ What public service really means in an era of constant disruption ☕ Why hiring managers should look beyond traditional career paths ☕ Finding purpose in uncertainty and career pivots Whether you’re a public servant, private-sector leader, first responder, or someone figuring out your next chapter, this conversation offers honest insight into building a meaningful career without a master plan.

    56 min
  6. Shared Responsibility Saves Lives: Craig Fugate on Disasters and Leadership

    Feb 9

    Shared Responsibility Saves Lives: Craig Fugate on Disasters and Leadership

    What does leadership look like when the clock is already running? In this episode of Careers & Coffee Talk, I sit down with Craig Fugate, former FEMA Administrator and longtime emergency management leader, to talk about what it really takes to respond when disaster strikes, and how those lessons still apply today. Craig shares his career journey from volunteer firefighter and paramedic to leading FEMA through some of the most demanding disaster years on record. We talk about why speed matters more than perfect information, how back-to-back disasters can reshape leadership, and what he learned rebuilding trust in FEMA by focusing on execution and outcomes. Our conversation also dives into emergency management as a shared responsibility: why bystanders are often the first responders and why empowering the public leads to better outcomes. Craig explains how better information changes decision-making and what today’s emergency managers should understand about AI, automation, and predictive tools. We also take a look ahead at the skills the next generation of emergency managers will need, the work Craig is doing now through his consulting practice, and the experience for survivors when emergency management gets it right.

    1h 1m
  7. From the Marine Corps to the Mat: Coach Kelly Grissom on BJJ, Lineage, and Leadership (Part 2)

    Jan 28

    From the Marine Corps to the Mat: Coach Kelly Grissom on BJJ, Lineage, and Leadership (Part 2)

    In Part 2 of this two-part conversation, we pick up where military service meets lifelong practice. Retired Marine Major Kelly Grissom, known to many as Coach Kelly, shares how his transition from the Marine Corps led him to Brazilian Jiu Jitsu, and how the principles of leadership, discipline, and accountability carried seamlessly from command to the mat. We talk about: ☕ Discovering BJJ as a path to self-mastery ☕ Why the name KOA connects his military service to his next chapter ☕ The importance of lineage in martial arts, including the influence of Master Leo Dalla ☕ Training first responders, military, and federal law enforcement ☕ Coaching confidence, humility, and resilience — without overemphasizing competition ☕ What it means to leave behind a legacy This episode is about showing up every day, doing the work, and carrying forward what was entrusted to you. 👉 Part 1 is available now, covering Kelly’s Marine Corps career and his career-defining experience in Afghanistan during Operation Whalers.

    57 min
  8. Coach Kelly Grissom on Operation Whalers, Combat Leadership, and the Path to Jiu Jitsu (Part 1)

    Jan 18

    Coach Kelly Grissom on Operation Whalers, Combat Leadership, and the Path to Jiu Jitsu (Part 1)

    What does leadership really demand, when the stakes are real and the consequences last? In Part 1 of this two-part conversation, I sit down in person with retired Marine Major Kelly Grissom, known to many today as “Coach Kelly," to talk about the chapter of his life that shaped everything that followed. Kelly shares his journey from enlisting in the Marine Corps to leading Marines around the world, including his role as Company Commander during Operation Whalers in Afghanistan in 2005. We talk candidly about leadership under uncertainty, the weight of command, and how public narratives often miss what leadership actually looks like on the ground. We also discuss the transition home, why you don’t return from experiences like that unchanged, and how those lessons carried Kelly toward Brazilian Jiu Jitsu and yet another form of service. This episode focuses on leadership, responsibility, and identity beyond the uniform. 👉 Part 2 drops next week, where we shift to the mat: lineage, coaching, training first responders, and how Kelly built KOA Martial Arts as a community rooted in discipline, humility, and purpose. Stay tuned!

    46 min
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5
out of 5
14 Ratings

About

Welcome to Careers & Coffee Talk — where real people spill the beans about their real career journeys, one cup at a time. ☕ We’re here for the twists, turns, fresh starts, and all the moments in between that shape us. These are quick, casual coffee chats with people figuring it out as they go — just like the rest of us. Because the best stories (and the best advice) are always better over coffee.

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