Should You Flex at Work? The Career Math Behind Showing Wealth

More from Per My Last Email

1. 

   4 May 2026 · 45 min

   The Hidden “BS” Holding You Back at Work (And How to Break It)

   In this episode, Kaila and Kyle are joined by Aiko Bethea, Founder of Rare Coaching, to talk about the hidden bullsh*t at work, how it’s holding you back, and what you can do about it. From holding yourself, your colleagues, and even bosses accountable, to freeing yourself of a scarcity mindset, this conversation is packed with practical advice for anyone feeling stuck in their career. And don’t forget to pick up Aiko’s new book, Anchored, Aligned, Accountable: A Framework for Transcending Bullsh*t and Transforming Our Lives and Work. 00:00 Intro 02:04 What Aiko is referring to when she…

2. 

   27 Apr 2026 · 38 min

   The 5 Sneaky Ways You Might Be Sabotaging Your Career

   In this episode, Kaila and Kyle break down the five sneaky (and surprising) things that are affecting your career, and what you can do about them. 00:00 Intro 02:42 Why your commute is more important than you think 08:00 Tactics if your commute is negatively impacting your career 11:00 How discussing your AI use can impact your career 17:59 The consequences of being unknown at work 22:27 Tactics for making yourself better known at work 24:51 How bad tech affects your career 30:16 Dealing with manager burnout This episode was sponsored by Allergy Insider. Ask your primary care provider about…

3. 

   20 Apr 2026 · 39 min

   Meetings Suck—Here are the Science-Backed Ways to Fix Them

   In this episode, Kaila and Kyle are joined by Rebecca Hinds, PhD, author of Your Best Meeting Ever: 7 Principles for Designing Meetings That Get Things Done. Rebecca breaks down the science behind why meetings so often fail—and shares research-backed tactics to decide which meetings are actually worth having, and how to design them for better outcomes. 00:00 Intro 02:36 Why do meetings suck? 03:47 Meeting Doomsday 05:40 Determining which meetings are actually useful 08:03 Considering remote employees 10:11 Making better meeting agendas 13:53 How to stop attendance inflation 16:13 How to…

4. 

   6 Apr 2026 · 40 min

   Why AI Isn’t Killing Jobs (And What It’s Actually Changing)

   In this episode, Kaila and Kyle are joined by LinkedIn Chief Economic Opportunity Officer (and former speech writer for President Obama) Aneesh Raman to talk about why we can be optimistic about AI. Aneesh’s new book, Open to Work: How to Get Ahead in the Age of AI, challenges the notion that AI is the death of entry-level work and instead argues that the technology is simply changing work as we know it in exciting and innovative ways. 00:00 Intro 02:30 How does AI unleash human potential? 06:25 Will AI weaken our ability to think? 11:48 Will AI increase the potential for cognitive debt?…

5. 

   30 Mar 2026 · 39 min

   You Survived a Layoff…Now What? (The Truth No One Tells You)

   While there is a lot of advice out there about what to do if you’ve been laid off, there isn’t a lot of information for how to manage if you’re one of the lucky (or not so lucky) survivors of a layoff. From being more vulnerable to burnout to taking on more responsibilities, Kaila and Kyle discuss how to handle surviving a layoff both emotionally and professionally, as well as discuss how they navigated their own layoff survival stories. 00:00 Intro 03:06 Kaila and Kyle’s layoff survival story 07:35 What NOT to do if you’ve survived a layoff 12:27 How your work changes post-layoff 16:48…

6. 

   23 Mar 2026 · 36 min

   Inside the Recruiter’s Brain: How to Get Hired in the Age of AI

   In this episode, Kaila and Kyle are joined by author, speaker, and ZipRecruiter career expert Sam DeMase (@apowermood) to share the best tips for landing a job in the age of AI. From understanding how recruiters think and operate, to structuring your resume for maximum impact, to mastering the “upper third,” this is one episode you don’t want to miss. 00:00 Intro 01:10 What is the life of a recruiter like? 06:28 How people are finding new jobs is changing 09:28 How to make yourself more appealing to recruiters on LinkedIn 12:59 Shifting from a experience-based resume to a skills-based resume…

7. 

   5 Oct 2026 · 35 min

   The “Enshittification” of Work: Why Your Career Feels Broken

   In this episode, Kaila and Kyle dive into Kaila’s theory that we’re seeing the “enshittification” of work, and how it is impacting the job market, college, and the career ladder. Listen to hear them explain the theory, and discuss what you as either a job-holder or job-seeker can do about it. 00:00 Intro 01:24 Where the inspiration for this topic came from 05:13 What we mean by “enshittification” 11:13 The promise we were sold of college 15:49 The “planned obsolescence” of the career ladder 18:50 The messiness of the job market 25:54 Advice for navigating the “enshittification” of work Want…

8. 

   28 Sep 2026 · 36 min

   What Gen Z Really Thinks About Work, Loyalty, and Ambition

   In this episode, Kaila and Kyle are joined by Morning Brew creators Annie Bennett and Meg Baniewicz to talk about Gen Z and work—the stereotypes, myths, truths, and how they REALLY feel about all of it. 00:00 Intro 01:44 How Annie and Meg come up with work-based sketch ideas 04:40 The work life themes resonating with people right now (beyond AI) 09:16 The technological shift that defines Gen Z 12:18 Has the role of the office changed for Gen Z? 15:34 Is Gen Z trying to “act their wage”? 23:22 Lightning Round This episode was sponsored by Croissant. Croissant handles the sourcing, bookings,…

9. 

   21 Sep 2026 · 24 min

   5 Daily Habits That Could Transform Your Career by Year-End

   In this episode, Kaila and Kyle break down a 5-step plan on how to make the most of the last 100 days of the year, and how to not only achieve your goals, but also improve upon them. 00:00 Intro 01:33 The inspiration for this episode 04:26 Why we made the Last 100 Days of the Year plan 06:26 Step 1 09:51 Step 2 11:23 Step 3 13:07 Step 4 16:32 Step 5 18:23 Preparing to start the Last 100 Days of the Year plan This episode was sponsored by Croissant. Croissant handles the sourcing, bookings, and vendors for your distributed team all in one place. Try Croissant now and they'll host lunch for…

10. 

    14 Sep 2026 · 31 min

    The Problem with “Executive Presence”

    In this episode, Kaila and Kyle discuss the idea of “executive presence”—what it is and is NOT, why it can be harmful, and how to either adopt or navigate around it in order to move forward in your career. 00:00 Intro 02:05 The problem with the idea of “executive presence” 07:27 The chicken or egg problem 10:31 Game: Executive Presence or Executive Privilege? 16:59 Listener email about executive presence 20:09 Amanda Goetz’s KUBA framework 22:53 How to handle it if someone tells you that you don’t have executive presence This episode was sponsored by Croissant. Croissant handles the…

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