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The Gen Mess with Tess

The Gen Mess with Tess

By: Tess Brigham
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Are generational divides in the workplace and in life driving you crazy?

The Gen Mess with Tess is here to help! Hosted by Tess Brigham—certified coach, licensed therapist, TEDx speaker, author, and mom to a Gen Zer—this podcast tackles the challenges and complexities of navigating life and work across multiple generations. From the unique struggles of Gen Z to the evolving perspectives of Millennials, Gen X, and Baby Boomers, Tess brings her expertise to the table, offering practical advice, expert insights, and real conversations to bridge the generational gap. Whether you're trying to communicate better with colleagues, understand your kids, or just get a clearer perspective on the "mess" of it all, The Gen Mess with Tess is your go-to resource for understanding how different generations think, work, and live.

Hosted on Acast. See acast.com/privacy for more information.

Tess Brigham
Career Success Economics Management Management & Leadership Relationships Social Sciences
Episodes
  • Ep 41: From PR Glam to Career Jam: Storytelling Your Way Out of the Void
    Dec 24 2025

    What if finding your dream job actually takes a year—or even longer?


    In this eye-opening episode of "Gen Mess with Tess," host Tess Brigham sits down with career strategist Liz Helton to pull back the curtain on the realities of job searching and career transformation in today's ever-evolving workforce. If you've ever wondered why sending off hundreds of applications can feel like shouting into a void, this episode will reveal why—and most importantly, what you can do about it.


    Together, Tess Brigham and Liz Helton dig into:

    • The shocking length of the modern job search—and why it’s no longer a "three-month process"
    • How technology and AI have totally transformed the hiring landscape (for better and worse)
    • Actionable strategies for networking that actually work, whether you’re an introvert, a new grad, or making a mid-career pivot
    • The key differences in how Gen Z, Millennials, and Gen X approach work, fulfillment, and branding themselves
    • Why keeping your own “brag book” is essential for beating imposter syndrome and keeping your confidence alive amid career changes
    • How AI isn’t taking jobs, but people who know AI are—and how you can upskill right now


    You’ll learn practical tips for standing out in a crowded applicant pool, making LinkedIn work for you, and reframing both rejection and uncertainty as essential steps toward meaningful work. Plus, Liz Helton shares her own journey from PR exec to career consultant, and why sometimes your superpower is that thing that feels as natural as breathing.


    If you feel stuck, overwhelmed, or unsure about your next step—no matter your age—this heartfelt, actionable episode is for you.


    Episode Overview with Timestamps:

    • [00:00:01] Introduction: Bridging generational gaps at work
    • [00:01:16] Meet Liz Helton: From PR to guiding career transformations
    • [00:06:44] The evolving job search: Why it takes so much longer now
    • [00:08:47] Why everyone feels like they’re “shouting into a void”
    • [00:13:13] How to beat interview anxiety and imposter syndrome
    • [00:17:44] Building resilience: The emotional side of job hunting
    • [00:19:38] Essential networking tips for introverts and extroverts alike
    • [00:27:40] AI in the job hunt: What you need to know now
    • [00:36:42] How Gen Z, Millennials, and Gen X view work differently
    • [00:43:01] Liz Helton’s #1 piece of advice for anyone feeling stuck
    • [00:46:49] Where to find Liz Helton and free career resources


    Tune in to discover why you’re not alone in your career mess—and how you can thrive in it.

    Hosted on Acast. See acast.com/privacy for more information.

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    49 mins
  • Ep 40: Golden Handcuffs & Gut Checks: Escaping the Career Carousel
    Dec 17 2025

    What if the brutal truth is that your corporate job is more likely to slowly kill you with stress than set you up for a dream retirement?


    In this episode of Gen Mess with Tess, host Tess Brigham sits down with powerhouse business mentor, international speaker, and award-winning author Katrena Friel for a candid and eye-opening conversation about breaking free from the golden handcuffs—and finding your true value.


    Katrena Friel pulls back the curtain on her own journey, from teenage jobs and personal heartbreak to a devastating $30,000 scam—a turning point that sparked her to build her own thriving training and mentoring practice. Together, she and Tess Brigham dissect why so many Gen Xers are “quietly quitting” or burning out, how younger generations are refusing to repeat the cycle of debt and overwork, and why we need to rethink the way we approach careers, money, and even family living.


    Key highlights include:

    • The shocking downside of “more with less” workplace culture—and Australia’s new laws holding employers accountable for worker burnout and stress
    • Katrena Friel’s $30,000 lesson in self-belief (and how that “scam” became the best investment of her life)
    • The three inner compasses—mind, heart, and gut—and how to use them to turn self-doubt into an ally
    • Why so many “expert” coaches out there deliver nothing but an expensive lesson (and how to spot the real deal)
    • Generational shifts: Why Gen Z is saying "no" to the boomer/American dream—and the case for embracing multi-generational homes and decluttering your life to gain headspace
    • Building your own brand: What it means to be the product, and how Katrena Friel helps you discover the million-dollar model inside your life experience
    • The truth about online programs: Why up to 95% are never completed—and why transformation requires actual mentorship, not just another “passive income” promise


    Loaded with tangible advice, real talk, and a bit of industry myth-busting, this episode will make you rethink everything you thought you knew about career success, purpose, and what it takes to build a legacy—on your terms.


    Episode Overview by Timestamp:

    • [00:00:01] – Welcome and intro to Katrena Friel’s journey
    • [00:02:11] – Early jobs and learning to be a self-starter
    • [00:05:02] – Miscarriage, grief, and the life-changing $30,000 scam
    • [00:08:17] – The unregulated coaching industry and lessons from mistakes
    • [00:11:14] – The three inner compasses: Mind, gut, and heart
    • [00:16:39] – Why it’s so hard to leave corporate: Golden handcuffs and generational differences
    • [00:24:20] – Declutter your life: Practical steps for big change
    • [00:27:28] – Rethinking the family home and intergenerational wealth
    • [00:31:09] – The career marathon mindset and building your own expertise
    • [00:34:09] – “Done for you” programs vs. the myth of the passive online business
    • [00:42:59] – How to connect with Katrena Friel and next steps for listeners


    Tune in for an episode packed with hard truths, practical strategies, and inspiration to reinvent work and life—no matter your generation!

    Hosted on Acast. See acast.com/privacy for more information.

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    47 mins
  • Ep 39: Law & Order: Time Management Unit
    Dec 10 2025

    What if the secret to building a thriving law firm wasn’t about grinding out endless billable hours—but about rethinking the entire way attorneys work and lead?


    In this eye-opening episode of Gen Mess With Tess, host Tess Brigham welcomes law firm growth expert Alay Yajnik for a candid conversation that shakes up everything you thought you knew about legal hustle and business success.

    Discover how Alay Yajnik pivoted from running multimillion-dollar Silicon Valley companies to coaching attorneys—and why most lawyers stumble when it comes to building a lasting, profitable business. You’ll learn why working harder doesn’t always mean earning more, and how breaking out of traditional law firm mindsets—from hourly billing to team management and rate setting—is the real game-changer.


    Key episode highlights:

    • Why technical skills don’t equal business success (and how “The E Myth Revisited” nails the problem for lawyers, therapists, and service pros)
    • The biggest pain points holding law firm owners back—hint: it’s not just the “hours in a day”
    • How shifting your mindset can help you work smarter, not harder—and finally create the time and income you want
    • Navigating generational tensions in the workplace: What attorneys get wrong about Gen Z, and why the newest workforce expects more work-life balance and financial stability than ever
    • Real talk about raising rates, burnout, hiring, and having those difficult employee conversations (plus how to screen for clients who are truly ready for change)

    Whether you lead a law firm, run a small business, or just want to understand how generational perspectives are upending the way we work, this episode is loaded with actionable insights and relatable stories.

    Episode Overview:

    • [00:00:31] Tess Brigham: Welcomes Alay Yajnik; his background in law firm growth
    • [00:01:23] Alay Yajnik: Story of switching from Silicon Valley to coaching attorneys
    • [00:03:08] Discussion: Why attorneys make great clients and what they uniquely struggle with
    • [00:05:15] Skills gap between technical expertise and business acumen; "The E Myth Revisited"
    • [00:07:16] The real issue: Time, burnout, and working smarter
    • [00:09:32] Traditional law firms vs. startup mindset; resistance to change
    • [00:12:11] Symptom vs. cure: Time management as a lever for transforming business results
    • [00:13:19] Raising rates, money fears, and business growth challenges
    • [00:17:27] Navigating client readiness and coaching intake
    • [00:18:07] Generational tensions: Gen Z’s approach to work, bonuses, and raises
    • [00:22:05] How the cost of living, technology, and burnout are shaping new workplace expectations
    • [00:27:04] A deeper look at employee expectations, creativity, and the evolving legal workplace
    • [00:36:33] Final reflections: Lessons from coaching lawyers, generational stereotypes, and business owner frustrations
    • [00:41:06] How to connect with
    • Alay Yajnik and his resources for law firm owners
    • [00:43:17]
    • Intro Announcer: Show outro and next episode preview


    Tune in for an episode that’s more than just law—it’s about building the future of work, one honest conversation at a time.

    Hosted on Acast. See acast.com/privacy for more information.

    Show More Show Less
    44 mins
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