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PODCAST

Per My Last Email

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, government, nonprofit, and startup sectors—debate the trickiest challenges in work life, and share tactics on how to overcome them.

business careers

All Episodes

40:12

On Steve Madden’s Viral Interview and Politics in the...

Per My Last Email ·

2025/06/09

In this episode, Kaila and Kyle discuss the viral Steve Madden interview and debate whether CEOs and corporations should be expressing their political views, as well as how to navigate politics in the workplace.00:00 Intro 01:24 Steve Madden’s viral Cutting Room Floor interview 06:26 Lulu Cheng Meservey on “going direct” as a business leader 07:29 Stats on how different generations feel about companies voicing their political beliefs 09:53 Ben & Jerry’s vs. Target 15:07 Brian Armstrong’s

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38:45

Is People Pleasing Holding Your Career Back?

Per My Last Email ·

2025/06/02

In this episode, Kaila and Kyle dive into the problems with being a “people pleaser”, and how to balance being agreeable enough while also being effective and impactful at work. Plus, Kaila introduces The Workplace People Pleasing Matrix. 00:00 Intro 00:44 Defining what “people pleasing” actually is 01:55 Why the term “people pleaser” is inflammatory 06:09 Stats on agreeableness and income 07:53 The Workplace People Pleasing Matrix 17:12 The importance of knowing when to be agreeable 19:28

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34:19

Everything You Know About Work Stress is Wrong

Per My Last Email ·

2025/05/26

In this episode, Kaila and Kyle discuss work stress and whether we’ve been thinking about it in the wrong way. There’s clearly such a thing as too much stress, but what about too little? And is there an ideal amount of stress we should be aiming for in order to be most successful at our jobs?00:00 Intro 00:24 APA stats on stress and anxiety 02:53 Kaila’s relationship with work-related stress 06:57 Stats on workplace mental health 09:58 The Eustress Curve and how to rethink our relationship

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34:37

Busting Myths About the Most Common Career Cliches

Per My Last Email ·

2025/05/19

In this episode, Kaila and Kyle discuss common career tropes and debate whether or not the sayings hold up. Is HR really not your friend? Are your connections more important than your skills? Listen and find out.00:00 Intro 00:36 Career myth #1 - “No one knows what they’re doing.” 07:35 Career myth #2 - “HR is not your friend.” 12:51 Career myth #3 - “It’s not WHAT you know, it’s WHO you know.” 19:11 Career myth #4 - “Follow your passion, and you’ll never work a day in your life.” 27:33

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33:23

How to Be Happier at Work, with Dr. Laurie Santos

Per My Last Email ·

2025/05/12

In this episode, Kaila and Kyle are joined by Yale professor and host of The Happiness Lab podcast, Dr. Laurie Santos, to talk about the small ways you can find more meaning in your job, and the adjustments that help increase our happiness and well being at work. 00:00 Intro 00:44 Dr. Laurie Santos Intro 01:47 How much does your work factor into your overall happiness? 03:33 Dr. Santos’ take on the difference between how millennials and how Gen Z approach work 07:50 “Job crafting” 09:33

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37:14

Why Is AI So Annoying?

Per My Last Email ·

2025/05/05

In this episode, Kaila and Kyle discuss the problems with the current conversation around AI, and debate the issues with and the benefits of the technology for the workforce, society, and individuals.00:00 Intro 00:57 The problem with the discourse around AI 05:42 Why we’re not having good faith arguments around AI 09:43 The three use cases for AI that Kaila found helpful 17:28 Kaila’s concerns with AI 21:00 How Kyle uses AI in a way that’s additive and not a complete replacement of

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32:24

We Made You a Report Card for Your Job – Here’s Why

Per My Last Email ·

2025/04/28

In this episode, Kaila and Kyle talk about the value of giving your job its own performance review, the most effective way to do it, and the lowest rated jobs from their own career experiences. Get your copy of the Rate Your Job Template here! 00:00 Intro 06:46 The Rate Your Job Template 13:38 Explaining the template through an example 15:55 How Kaila used the Rate Your Job Template when choosing her current job 19:00 Using the template to rate your existing job 21:45 Why rating your job

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32:35

When A Side Hustle Is (and Isn’t) Worth It

Per My Last Email ·

2025/04/21

In this episode, Kaila and Kyle dive into what exactly constitutes a “side hustle”, and the circumstances in which it IS and ISN’T worth having one. Not all side hustles are created equal.00:00 Intro 03:11 Average income earned from a side hustle 05:11 The issue with the term “side hustle” 08:00 The most common types of side hustles 14:45 “Acceptable or Not?” game 20:46 Considering how a side hustle might be perceived at your job 21:48 Pros and cons of having a side hustle Want to get all of

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37:05

Can You Recession-Proof Your Job?

Per My Last Email ·

2025/04/14

In this episode, Kaila and Kyle dive into tips and tactics on the best way to protect your job and prepare yourself for potential job cuts during a recession.00:00 Intro 00:27 Listener email 03:19 What happens during a recession 06:24 What you can do to prepare yourself professionally if you are currently employed 09:10 “T-Shaped skills” 13:45 The importance of weak ties 19:09 Why you should consider posting on LinkedIn right now 21:06 Recession-proof industries 23:58 Recession-proof job

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30:44

Can You Be TOO Efficient at Work?

Per My Last Email ·

2025/04/07

In this episode, Kaila and Kyle discuss the reason why efficiency shouldn’t be the goal at work, and how to actually get better at your job.00:00 Intro 00:41 Our obsession with efficiency 02:26 The problem with the conversation around AI 06:46 What you lose when you focus too much on efficiency 11:42 When Kaila over-focused on efficiency in her career 18:06 How to actually get better at your job 19:46 Scheduling time for whimsy 23:17 Tactics Want to get all of Kaila & Kyle’s career resources

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35:48

Tackling Difficult Conversations with Erin McGoff

Per My Last Email ·

2025/03/31

In this episode, Kaila and Kyle discuss how to have those difficult conversations at work with career advice expert Erin McGoff of @advicewitherin. From addressing your lazy coworker to handling your micromanaging boss, Kaila, Kyle, and Erin offer specific tactics and approaches for conducting these challenging conversations.00:00 Intro 00:55 How Advice With Erin got started 03:49 Stats on how much people avoid having difficult conversations 04:34 How Erin recommends approaching difficult

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30:25

We React to Corporate Espionage: Rippling v Deel

Per My Last Email ·

2025/03/24

In this episode, Kaila and Kyle dig into the details of the Rippling v Deel corporate espionage lawsuit, and why—even if you aren’t a corporate spy yourself—it should matter to you.00:00 Intro 00:51 Background 07:26 Our reaction to the Rippling v Deel case 12:36 Remembering what Slack really is 18:08 What kind of information is okay to take with you from a job, and what is not 20:11 Noncompete clauses 21:59 “garden leave” 22:41 Why a work nemesis is good Want to get all of Kaila & Kyle’s career

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32:49

Are You a Bad Person If Your Job Doesn't Align With...

Per My Last Email ·

2025/03/17

In this episode, Kaila and Kyle get philosophical and discuss the ethics of working for a company that doesn’t align with your values. Is it ever acceptable to work at a job that you perceive as immoral? And what can you do if you have to work at such a place?00:00 Intro 05:30 Whether or it’s morally okay to work somewhere that goes against your values 09:08 Another important caveat when it comes to values aligning with your work 11:45 Effective altruism 16:08 How your role within an organization

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35:47

Is Nepotism In The Workplace Actually Bad?

Per My Last Email ·

2025/03/10

In this episode, Kaila and Kyle discuss the difference between nepotism vs. networking in the workplace, and how to make nepotism work for you even when you don’t think you have the connections you need to secure an opportunity. 00:00 Intro 00:46 Defining a “nepo baby” 04:54 How common workplace nepotism actually is 09:03 When people are, and are not okay with workplace nepotism 12:52 Is nepotism different from networking? 18:22 How to make nepotism work for you 19:56 The power of weak ties 22:19

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34:09

Are Millennial Managers Too “Soft?”

Per My Last Email ·

2025/03/03

In this episode, Kaila and Kyle discuss whether or not millennial managers are too soft, the different styles of management, and how to navigate giving tough feedback.00:00 Intro 02:29 How Kaila and Kyle define a “millennial manager” 07:49 The difference between a good millennial manager and a bad millennial manager 10:08 Previous generations vs millennials in terms of management styles 15:08 “Primal Leadership” and the styles of management 20:55 What to do if you have a millennial manager 24:27

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25:13

Am I The A**hole? Revenge Quitting, Work Frenemies,...

Per My Last Email ·

2025/02/24

We’ve done it again—this week Kaila and Kyle read and respond to your “am I the a**hole?” submissions around your work-specific situations…and they do not hold back.00:00 Intro 01:02 AITA scenario 1 | vengeful quitter 05:37 AITA scenario 2 | “friend” exploitation 09:57 AITA scenario 3 | senior exec’s personal tragedy 14:44 AITA scenario 4 | Reddit submission Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/ Watch Per My Last

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35:57

What Do DEI Rollbacks Mean For You?

Per My Last Email ·

2025/02/17

In this episode, Kaila and Kyle discuss the recent headlines around DEI, the potential implications of these measures, and what actually makes the most effective teams. 00:00 Intro 00:43 Recent headlines around DEI 06:05 Listener email 12:04 Stats around DEI from Morning Brew’s Insights and Analytics team 16:34 Why having a diverse workforce helps your business outcomes 20:04 An example of DEI efforts in the workplace 22:05 What are the the things that make for a truly high performing team? 24:49

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35:22

The Best Tips for Negotiating a Higher Salary, with...

Per My Last Email ·

2025/02/10

In this episode, Kaila and Kyle are joined by Hannah Williams, founder and host of @SalaryTransparentStreet, to talk about the importance of salary transparency, why it’s still such an uncomfortable thing to talk about, and how to negotiate for a higher salary.00:00 Intro 00:45 Hannah Williams and Salary Transparent Street 01:24 When Hannah first realized she was being underpaid 07:51 The experience of filming Salary Transparent Street 11:06 Why it’s so important to consider being transparent

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36:42

How to Take an “Adult Gap Year” – and When It’s Not...

Per My Last Email ·

2025/02/03

In this episode, Kaila and Kyle discuss the pros and cons of taking an “adult gap year” (aka sabbatical or “mini-retirement”), why they’re becoming more common, and how to financially plan for one if you want to take one yourself.00:00 Intro 01:56 Stats on burnout 05:54 Defining “sabbatical” vs “leave of absence” vs “gap year” or “mini retirement” 08:48 Companies providing sabbatical options 15:01 What Kyle and Kaila would do with a 4-week sabbatical 18:36 Harvard Business Review’s study on

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36:12

We React to Zuck’s “Masculinity” Comments and Meta’s...

Per My Last Email ·

2025/01/27

In this episode, Kaila and Kyle discuss some of the recent news surrounding Meta—from their announcement of cutting 5% of their workforce, to Mark Zuckerberg’s recent comments on masculinity in the workplace. 00:00 Intro 00:51 Meta’s recent announcement around firing practices 04:25 Two potential upsides to Meta’s “rank and yank” system 07:07 Issues with stack ranking systems 13:39 What is the ideal performance incentive at work? 17:29 How certain incentives cause “creaming” 20:09 What’s going on

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