Recent Episodes

Oct. 26, 2026

Corporate Horror Stories: Bad Bosses, Missing Bonuses & Maternity Leave Nightmares

In this episode, Kaila and Kyle detail some of the most horrifying (and unfortunately true) work experiences from listeners and friends, and discuss what they would do if they faced the same situation. 00:00 Intro 00:51 Corporate Horror Story #1: Getting iced out at work 04:43 What would you do in situation #1? 12:02 Corporate Horror Story #2: Maternity leave drama 17:43 Corporate Horror Story #3: Wildly uncomfortable office dynamics Want to get all of Kaila & Kyle’s career resources? Subs
Oct. 19, 2026

The Trap of Success: Why Working at a Successful Company Can Hurt Your Career

In this episode, Kaila and Kyle discuss the potential career pitfalls of working at a successful company, and how to avoid the “trap of success” when you do. 00:00 Intro 03:53 Kaila’s experience of leaning on Morning Brew’s success 06:52 Why it’s easy to get lazy at a successful company 09:19 The traps to be aware of at a successful company 14:45 How potential employers should analyze candidates from successful companies 16:56 Discussing the trap of success 22:51 A final note on the trap
Oct. 12, 2026

Busting Myths About Millennials at Work with Morning Brew Daily’s Neal Freyman & Toby Howell

In this episode, Kaila and Kyle are joined by Morning Brew Daily hosts Neal Freyman and Toby Howell for a funny and insightful conversation around millennials at work—the stereotypes, the myths, the areas of strength and the areas that could use some improvement. 00:00 Intro 01:12 What distinguishes millennials from Gen Z 07:57 Millennial myth: millennials are job hoppers 11:36 Millennial myth: millennials seek careers with purpose 15:08 Millennial myth: millennials need praise 18:39 Mille
Oct. 5, 2026

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
Sept. 28, 2026

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”? 2
Sept. 21, 2026

“75 Hard” for Your Career: The 5-Step Plan to Finish the Year Strong

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, booki

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