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.
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The Trap of Success: Why Working at a Successful Company Can Hurt Your Career
Monday, October 19, 2026 • Duration 30:48
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 of success
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
Learn more about your ad choices. Visit megaphone.fm/adchoices
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!
Busting Myths About Millennials at Work with Morning Brew Daily’s Neal Freyman & Toby Howell
Monday, October 12, 2026 • Duration 32:38
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 Millennial myth: millennials are too soft as managers
24:07 Lightning Round
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
Learn more about your ad choices. Visit megaphone.fm/adchoices
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!
The “Enshittification” of Work: Why Your Career Feels Broken
Monday, October 5, 2026 • Duration 35:08
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 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
Learn more about your ad choices. Visit megaphone.fm/adchoices
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!
What Gen Z Really Thinks About Work, Loyalty, and Ambition
Monday, September 28, 2026 • Duration 36:23
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, and vendors for your distributed team all in one place. Try Croissant now and they'll host lunch for you and your team in a Croissant space. Go to: getcroissant.com/PMLE.
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
Learn more about your ad choices. Visit megaphone.fm/adchoices
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!
5 Daily Habits That Could Transform Your Career by Year-End
Monday, September 21, 2026 • Duration 23:59
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 you and your team in a Croissant space. Go to: getcroissant.com/PMLE.
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
Learn more about your ad choices. Visit megaphone.fm/adchoices
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!
The Problem with “Executive Presence”
Monday, September 14, 2026 • Duration 31:02
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 sourcing, bookings, and vendors for your distributed team all in one place. Try Croissant now and they'll host lunch for you and your team in a Croissant space. Go to: getcroissant.com/PMLE.
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
Learn more about your ad choices. Visit megaphone.fm/adchoices
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!
6 Habits to Steal From the Most Successful Leaders
Monday, September 7, 2026 • Duration 31:28
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. Croissant handles the sourcing, bookings, and vendors for your distributed team all in one place. Try Croissant now and they'll host lunch for you and your team in a Croissant space. Go to: getcroissant.com/PMLE.
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
Learn more about your ad choices. Visit megaphone.fm/adchoices
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!
Am I the A**hole? Clapping Back at Work, Refusing a Referral and More
Monday, August 31, 2026 • Duration 27:03
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 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
Learn more about your ad choices. Visit megaphone.fm/adchoices
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!
4 Types of Networking You’re Probably Ignoring
Monday, August 24, 2026 • Duration 29:15
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 posting on LinkedIn)
20:17 The networking you do with your own boss
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
Learn more about your ad choices. Visit megaphone.fm/adchoices
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!
BONUS: The Career Advice We Wish We Knew in Our 20s (Live)
Thursday, August 20, 2026 • Duration 42:35
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 Sachs
04:19 Kyle’s first career experiences
08:57 On figuring out what you want to do with your career
11:41 The 30-60-90 Framework
16:41 On learning from your bosses
17:47 Using naivete to your advantage
19:59 SVP of Human Resources, Christina Schelling
22:02 Christina’s experience at the CIA
26:41 The unexpected skills that are becoming more valuable today
30:25 The areas that young professionals should focus on developing in the first 5 years
35:33 The cost of perfectionism in your career
39:37 The questions young professionals should ask in interviews
This episode was sponsored by Verizon. Visit mycareer.verizon.com to apply to open roles and learn more about working at Verizon today.
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
Learn more about your ad choices. Visit megaphone.fm/adchoices
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!
Per My Last Email, a podcast by Morning Brew - Stats, Episodes and Rankings - My Podcast Data