

Per My Last Email
Morning Brew
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.
Episodes
Mentioned books

Sep 29, 2025 • 34min
Is Dating Your Coworker Ever Worth It?
In this episode, Kaila and Kyle debate whether you should or should NOT pursue your office crush. That’s right—we’re talking office romance this week, and Kaila and Kyle hold strongly opposing positions on the matter, based in part on their own personal experiences.
00:00 Intro
02:57 Historical context for the conversation
04:23 Kaila’s opinion on pursuing a relationship in the workplace
08:19 The types of jobs where office romance becomes more likely
15:53 The most important thing to remember when considering a romantic relationship with a coworker
18:58 Power dynamics in coworker relationships
21:02 Disclosure
22:35 Never be the main character
26:28 Perception
28:19 Kaila’s 4 conditions for pursuing an office romance
This episode was sponsored by Udemy. Try a free 14-day trial at Udemy now at udemy.com/personal-plan and use code PMLE14.
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! Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 22, 2025 • 37min
Is it Cringe to Try Hard at Work?
Is it cringe to try too hard? In this episode, Kaila and Kyle are joined by Normal Gossip co-creator and Defector Media co-owner Alex Sujong Laughlin to talk about the ins and outs of being a “try hard” at work. Alex’s new podcast, Try Hard, documents people attempting things that they’re afraid to do, and in this episode you’ll hear about a couple of moments when Alex and Kaila’s fear of being cringe nearly held back their career progress.
00:00 Intro
01:40 What is “Try Hard”?
05:29 Why being a “try hard” in the office is perceived as cringe right now
12:33 An experience that almost derailed Alex’s career path
17:18 How to gently encourage trying hard
21:33 What’s the right level of earnestness at work?
25:42 Is LinkedIn posting cringe?
28:09 A time where Kaila’s fear of being “cringe” almost held her back in her career
This episode was sponsored by Udemy. Try a free 14-day trial at Udemy now at udemy.com/personal-plan and use code PMLE14.
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! Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 15, 2025 • 31min
Why Middle Managers Matter More Than You Think
In this episode, Kaila and Kyle discuss the current trend of laying off middle managers and the flattening of organizations, the impact this can have on individuals, and why we can’t forget the key roles that middle managers have in your career.
00:00 Intro
01:43 Who are the middle managers?
04:15 Stats illustrating the decline of the middle manager
06:40 How an absence middle managers can hinder your career
11:09 The goal of a middle manager, and what happens when they disappear
18:44 Why companies should realize the importance of a middle manager
23:45 What to do if you see a flattening of your organization
This episode was sponsored by Udemy. Try a free 14-day trial at Udemy now at udemy.com/personal-plan and use code PMLE14.
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! Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 8, 2025 • 34min
How to Survive in an AI-Dominated Job Market
In this episode, Kaila and Kyle discuss how AI is impacting the job market, what the future of work may look as more roles and industries become automated, and how to stand out in the age of AI-assisted hiring processes.
00:00 Intro
01:41 Research on the impact of AI on job seekers
06:28 The rise of the “he-cession”
10:07 How AI is impacting the job hunt for mid-career level individuals
14:02 Strategies for applying to jobs in the current environment
19:20 Tips for once you finally reach the interview process
24:03 A major networking pro-tip, especially if you have a small network
This episode was sponsored by Udemy. Try a free 14-day trial at Udemy now at udemy.com/personal-plan and use code PMLE14.
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!
Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 1, 2025 • 40min
How to Navigate a Toxic Work Environment
Discover how to navigate the tricky realm of toxic workplaces, focusing on three key scenarios: toxic coworkers, challenging bosses, and problematic environments. Hear personal anecdotes that highlight the emotional toll of toxicity and the importance of communication in managing such relationships. Gain insights into the signs of toxic leadership and reflect on your own role in creating workplace harmony. Plus, enjoy a bonus tip that unveils a lesser-known aspect of workplace toxicity, rounding out essential strategies for a healthier work life.

Aug 25, 2025 • 39min
The Leadership Traits the Top 1% of Executives Use to Climb the Ladder
In this episode, Kaila and Kyle get educated on the four most important qualities of leadership that separate the top 1% of executives from the rest. Cassie Young, General Partner at Primary Venture Partners, joins Kaila and Kyle this week to discuss why these are the most important (and underappreciated) leadership traits, and why it’s important to know them even if you’re not a leader yourself.
00:00 Intro
02:32 Cassie’s career trajectory
08:00 “Highly forgettable people”
09:39 A tip for when deciding on a job based on the manager
10:21 The value of P&L fluency
15:44 Cassie’s favorite hack for getting more fluent in profit and loss
16:52 “First Team” leadership
24:03 “Pulse on Macromarket”
29:08 The importance of “bat phone” relationships
This episode was sponsored by Gamma. Try Gamma now at https://gamma.app/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! Learn more about your ad choices. Visit megaphone.fm/adchoices

4 snips
Aug 18, 2025 • 39min
Can You Get Wealthy With Just Your 9 to 5 Job Anymore?
The discussion revolves around the shifting landscape of wealth creation in today’s job market. Is the American Dream still alive or has it transformed? Kaila and Kyle explore how younger generations perceive wealth, emphasizing non-traditional career paths. They weigh the benefits of equity in startups against stable salaries and urge listeners to redefine expectations around financial success. Moreover, the conversation highlights the significance of having a financial safety net and aligning career choices with personal values for long-term happiness.

Aug 11, 2025 • 37min
Balancing Friendship Inside & Outside of Work, with Morning Brew Daily’s Neal Freyman & Toby Howell
In this episode, Kaila and Kyle are joined by Morning Brew Daily hosts Neal Freyman and Toby Howell to talk about a subject they know better than anyone—the reality of having a work bestie. Listen to hear Neal and Toby share the story of how they went from colleagues, to friends, to podcast co-hosts, and the unexpected benefits and potential drawbacks of having such a tight working relationship.
00:00 Intro
02:09 How Neal and Toby originally became friends
07:58 How being both friends and colleagues has affected their work
10:12 Developing the Morning Brew Daily show
13:31 On the period that Toby and Neal were together 24/7
16:14 Advice for someone unsure about cultivating a deep friendship at work
20:30 The difference between having work friends at a small company versus a larger one
23:00 Neal and Toby answer questions from their own Morning Brew Daily production team
29:41 Game:
This episode was sponsored by Gamma. Try Gamma now at https://gamma.app/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!
Learn more about your ad choices. Visit megaphone.fm/adchoices

Aug 4, 2025 • 40min
What Parental Leave is Actually Like
In this episode, Kaila and Kyle discuss Kyle’s experience of paternity leave so far, what’s been the most surprising to him, and how he’s feeling about returning to his 9 to 5.
00:00 Intro
01:32 Stats on maternity vs. paternity leave in the U.S.
05:02 Research on the impact of taking paternity leave on a father’s brain
08:11 How pat leave has been for Kyle
13:53 Kyle’s feelings around returning to work
18:24 How boundaries shift after paternity leave
23:37 How Kaila’s thinking about parental leave
33:41 The systemic problem that lack of parental leave policy in the U.S. is creating
This episode was sponsored by Gamma. Try Gamma now at https://gamma.app/partners/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!
Learn more about your ad choices. Visit megaphone.fm/adchoices

8 snips
Jul 28, 2025 • 32min
Business IS Personal, and Other Non-Obvious Truths
The hosts dive into surprising truths about work that challenge common perceptions. They discuss the intricacies of workplace exploitation, particularly for Gen Z, highlighting the risks and boundaries essential for career growth. The conversation shifts to 'personality hires' and how charisma must complement job performance to bolster team dynamics. Lastly, they emphasize the power of vulnerability in professional success and share a clever productivity hack for enhancing efficiency.