Episode notes
In this episode, Kaila and Kyle debate whether or not taking a real vacation even exists anymore, and provide tactics for how to protect your off time. Can you ever really fully log off in a world with flexible working conditions? And how can we reclaim PTO? 00:00 Intro 02:20 How we got to the state of the working “vacation” 06:59 The real vs imagined expectations of your employer 11:08 Setting clear expectations with your team 14:32 Flexibility’s pros and cons 21:27 The other reason we can’t fully log off anymore 25:20 Other tactics for getting your vacation time back Want to get all of…
Per My Last Email
by Morning Brew · English · Business
Is it okay to ask your coworker how much they make? Is Gen Z set up for failure in the workplace? Should you really bring your whole self to work? Each week on Per My Last Email, Morning Brew's resident career experts Kaila and Kyle—whose careers have collectively spanned the corporate,…
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27 Jul 2026 · 30 min
AI Is Changing How We Talk to Each Other...And It's Annoying
In this episode, Kaila and Kyle discuss how AI is starting to impact how we communicate with one another at work. There are both obvious and subtle ways in which the technology is affecting how we speak, and Kaila and Kyle have some strong feelings about it. 00:00 Intro 00:18 The problem 04:04 How we got here 09:41 The inciting concern about how we talk to chatbots 13:05 Another communication heuristic that has been altered by AI 15:56 How using AI can be corrosive to work relationships 21:11 The linguistic tip-offs that signal something might have been written by AI 23:35 Another way that…
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20 Jul 2026 · 35 min
The Workplace Habits That Are Quietly Hurting Your Body & Brain
In this episode, Kaila and Kyle dig into the unexpected ways in which work impacts our mental and physical health, and provide some tactics for how to avoid some of these health risks whether you work remotely or in an office. 00:00 Intro 02:22 Remote work and unhappiness 09:28 Kaila’s hot take on remote work 11:27 Tactics to avoid the pitfalls of remote work 16:00 The impact of work on our physical health 18:55 The thing impacting our health more than sitting all day 22:08 Why going into the office (vs working remotely) might be healthier overall 24:13 Middle Manager-itis 29:54 Per My Last…
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13 Jul 2026 · 38 min
The Workplace Tech Trends You Can't Ignore (AI, Surveillance & RTO)
In this episode, Kaila and Kyle are joined by Tech Brew’s editor Saira Mueller to discuss current and emerging tech trends—from AI to surveillance technology—and how they’re impacting the workplace, and what we can do to improve our own work environment with them (or in spite of them). 00:00 Intro 01:39 How AI use has trended in the workplace 11:14 The AI software that has most impressed Tech Brew’s editor 12:24 The tech trends that have emerged with RTO (return to office) 15:33 Surveillance technology 18:47 The other reason companies use surveillance technology 21:44 Technology backlash and…
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29 Jun 2026 · 34 min
The Career Advice You Need at 25, 35, and 45
In this episode, Kaila and Kyle are joined by Cherry Miao, CFO of Hightouch, who gets into the art of conducting an effective job interview, how she susses out a job candidate’s mindset, and what she thinks should be changed about the job interview process in general. She also breaks down the skills that are most important to hone in each stage of your career—from your first entry-level job all the way to the C-Suite. 00:00 Intro 01:06 The art of the interview, and how Cherry identifies top talent in interviews 07:27 The blameless retro 09:26 Mindset vs skillset 11:05 What Cherry would like…
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22 Jun 2026 · 39 min
How Ambitious Do You Actually Need To Be To Succeed?
In this episode, Kaila and Kyle are debating ambition: do you really need to be super ambitious to have a successful career? What level of ambition is the ideal amount? And can you be ambitious in both work and life in equal measure? 00:00 Intro 01:21 How we’re defining “ambition” 05:42 Can you succeed without ambition? 13:30 What is the opposite of ambition? 17:05 Kaila’s framework for thinking about the qualities necessary for career success 18:18 How ambitious SHOULD you be? 24:04 Can you be ambitious at work and have some level of work life balance? 27:07 Advice if you’re questioning…
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15 Jun 2026 · 47 min
The Surprising Power of Constraints at Work (with David Epstein)
In this episode, Kaila and Kyle are joined by author David Epstein to discuss the topic of his latest book, Inside the Box: How Constraints Make Us Better. Listen to hear why constraints increase both productivity and creativity, and how to implement them on your own to help you in work and life. 00:00 Intro 02:05 The story of General Magic 06:02 Additive bias 09:14 Brooks’s Law 12:34 How Bell Labs is an example of useful constraints 14:48 Can removing constraints ever be beneficial? 19:31 How do we build a constraint to prevent distraction? 23:49 David’s observations on AI’s impact on human…
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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…
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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,…
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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…
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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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