Episodes

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...

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 ...

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...

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...

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...

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...

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 ...

In this episode, Kaila and Kyle talk about the habits they’ve observed in the most effective and successful leaders they know, and how to incorporate them into your own work life. (And let’s just say a few of them are a bit controversial.) 00:00 Intro 02:31 Habit #1 08:50 Habit #2 12:38 Habit #3 17:59 Habit #4 21:18 Habit #5 24:32 Habit #6 This episode was sponsored by Croissant. If managing workspace for a distributed team has somehow become your job, go to getcroissant.com/PMLE. Croiss...

In this episode, Kaila and Kyle bring you another round of a fan favorite: Am I The A******? Listen to hear Kaila and Kyle react to some of the wildest, work-related AITA posts on Reddit, and weigh in with their professional advice. 00:00 Intro 00:25 Scenario 1 | Clapping back at a coworker 06:41 Scenario 2 | Office desk assignment 12:44 Scenario 3 | Job referral 18:27 Scenario 4 | Covering my friend’s maternity leave Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My ...

In this episode, Kaila and Kyle dig into the more subtle (but incredibly important) forms of networking that you might not be thinking about. Whether it’s honing your personal brand or expanding your weak ties, Kaila and Kyle share some excellent tips on the more unexpected ways to network. 00:00 Intro 00:39 Kaila’s experience with back-channeling 04:26 Peer-to-peer networking 10:56 Building up weak ties 14:16 Building your personal brand 18:42 Ways to grow your personal brand (beyond post...

In this special bonus episode, Kaila and Kyle tape their very first live episode at Verizon HQ in Basking Ridge, New Jersey. Listen to hear Kaila and Kyle share what they learned from their own early career experiences with Verizon’s intern class (aka VTerns), as well as hear professional insights and advice from Christina Schelling, Verizon’s own SVP of Human Resources (whose early career experiences include working for the CIA). 00:00 Intro 03:08 Kaila’s internship experience at Goldman Sach...

In this episode, Kaila and Kyle discuss why perfectionism is actually a negative at work (and in life), and how to overcome it. And as a self-proclaimed recovering perfectionist, Kaila offers some excellent tactics and tips. 00:00 Intro 01:48 The misconception about perfectionism 06:16 The impacts of perfectionism 14:38 On whether we overrate intelligence 16:22 Measuring the delta between time and output 19:31 100 rejections in 100 days Want to get all of Kaila & Kyle’s career resources? ...

In this episode, Kaila and Kyle dig into and debate the most overrated and underrated work perks, and how to make the most of the ones you’re probably overlooking. Summer Fridays? Education credits? Unlimited PTO? You might be surprised by some of their controversial takes. 00:00 Intro 00:14 Reviewing the Morning Brew company party 05:09 Kaila’s party strength vs. Kyle’s party strength 06:53 Are company parties a good work perk? 08:42 Underrated work perk #1 10:28 Underrated work perk #2 ...

In this episode, Kaila and Kyle list the most annoying and the most appreciated qualities in a coworker. Plus, how to make the most of those good qualities and navigate the grating ones. 00:00 Intro 01:08 Coworker pet peeve #1 06:02 Coworker pet peeve #2 10:15 Coworker pet peeve #3 12:50 Coworker pet peeve #4 15:23 Coworker green flag #1 19:19 Coworker green flag #2 21:00 Coworker green flag #3 23:23 Coworker green flag #4 Want to get all of Kaila & Kyle’s career resources? Subscribe t...

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 2...

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...

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 Surveillanc...

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 ca...

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 ta...

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 ...

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? 19:3...

In this episode, Kaila and Kyle dig into the unspoken rules of social media at work. When is it okay to follow a colleague on Instagram? When is posting about your company empowering vs. harmful? And is it okay to have no social media presence at all? 00:00 Intro 00:58 Which social platforms you should and should not follow your coworkers on 08:05 A good rule of thumb for deciding whether or not to follow a coworker on Instagram 09:58 The most important thing to keep in mind when it comes to...

In this episode, Kaila and Kyle are joined by Milly Tamati, the founder of generalist.world, to talk about the benefits of being a career generalist (vs. a specialist), what people get wrong about generalists, and how to start building a portfolio career. 00:00 Intro 01:29 Defining what a “generalist” is 02:27 What does a long-term generalist career look like? 04:42 What people get wrong about specialists vs generalists 07:39 How do you figure out your strengths and fit as a generalist? 14...

In this episode, Kaila and Kyle discuss all things retirement—how the concept of retirement has changed, how they’re financially planning for their own retirements, and what their ideal retirement looks like. 00:00 Intro 01:33 What does retirement look like right now? 08:48 How Kaila and Kyle approach the financial element of retirement 12:58 Thinking about the non-financial aspects of retirement 22:30 Mini retirements 25:45 Where Kaila and Kyle plan to retire 31:13 Per My Last Policy Th...