Per My Last Email

Latest Episodes:

Coworker Pet Peeves: What We Hate and What We Love Aug 03, 2026

Show notes

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

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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. Share the show with a friend, and leave us a review on your favorite podcast app!

AI Is Changing How We Talk to Each Other...And It's Annoying Jul 27, 2026

Show notes

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 AI is changing how we speak

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The Workplace Habits That Are Quietly Hurting Your Body & Brain Jul 20, 2026

Show notes

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 Policy

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/

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The Workplace Tech Trends You Can't Ignore (AI, Surveillance & RTO) Jul 13, 2026

Show notes

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 how to unplug

29:54 Game: Signal or Noise

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/

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Does a Real Vacation Even Exist Anymore? Jul 06, 2026

Show 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 Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/

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The Career Advice You Need at 25, 35, and 45 Jun 29, 2026

Show notes

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 to see changed about the hiring process

13:25 The anti-sell interview

15:29 The most important skill to develop as an early career professional

18:41 Advice for the transition into mid-career

23:37 What C-suite level professionals should be focused on

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/

Watch Per My Last Email on YouTube:

@PerMYLastEmailShow

Follow Per My Last Email

Instagram: @permylastemailshow

TikTok: @permylastemailshow

Twitter: @permylast_email

Have a question for us? Send us an email or voice note to permylastemail@morningbrew.com

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How Ambitious Do You Actually Need To Be To Succeed? Jun 22, 2026

Show notes

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 your own level of ambition

31:46 Work Rants

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/

Watch Per My Last Email on YouTube:

@PerMYLastEmailShow

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Instagram: @permylastemailshow

TikTok: @permylastemailshow

Twitter: @permylast_email

Have a question for us? Send us an email or voice note to permylastemail@morningbrew.com

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The Surprising Power of Constraints at Work (with David Epstein) Jun 15, 2026

Show notes

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 productivity

27:30 Creativity and the Green Eggs and Ham Effect

31:07 What is the relationship between creativity, expertise, and constraints?

35:08 Is having unlimited professional options actually good career advice?

39:28 Decision-making and Fredkin’s Paradox

41:00 How David’s two books Range and Inside the Box tie into one another

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/

Watch Per My Last Email on YouTube:

@PerMYLastEmailShow

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Instagram: @permylastemailshow

TikTok: @permylastemailshow

Twitter: @permylast_email

Have a question for us? Send us an email or voice note to permylastemail@morningbrew.com

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Following Coworkers on Instagram and Other Social Media Dilemmas Jun 08, 2026

Show notes

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 following on social media

18:11 Posting as a form of empowerment

21:32 Finding the balance between posting too much and posting too little

23:50 Should phones be banned from the office?

Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/

Watch Per My Last Email on YouTube:

@PerMYLastEmailShow

Follow Per My Last Email

Instagram: @permylastemailshow

TikTok: @permylastemailshow

Twitter: @permylast_email

Have a question for us? Send us an email or voice note to permylastemail@morningbrew.com

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The Rise of the Career Generalist (and Why It Matters More Than Ever) Jun 01, 2026

Show notes

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?

14:52 What is a “portfolio career”?

21:16 Are there certain personalities that are best suited for a portfolio career?

23:06 How Milly is thinking about AI

27:03 Is it more beneficial in the long run to be a generalist given the AI boom?

31:57 Per My Last Policy

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