In this episode, Kaila and Kyle celebrate the 100th episode of Per My Last Email with a fun and informative variety show, followed by a surprise walk down memory lane at the end.

00:00 Intro

00:32 News You Can Use

07:55 A check-in with our Gen Z correspondents 

15:00 Game: Slay or Nay?

18:41 Skillcation report

23:47 Per My Last Email gets a performance review

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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Have a question for us? Send us an email or voice note to [email protected]

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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!

Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Kyle sits down with venture capitalist and author Bill Gurley to talk about how to figure out your passion, what people get wrong about networking, and why pursuing your dream career isn’t such an idealistic idea. 

00:00 Intro

01:23 How do we recognize if we have a “passion”?

04:40 Do we spend enough time in a sampling period?

08:48 Something Bill advises young people to ask of older adults

09:14 How Bill responds to the pushback that people should aim for a stable, money-making career instead of their dream jobs

11:21 On mentorship and networking

17:09 Bill’s “Go where the action is” principle 

21:54 Advice to people early in their career with regards to emerging technologies

Be sure to check out Bill’s new book, Runnin’ Down a Dream: How to Thrive in a Career You Actually Love.

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 [email protected]

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

In this episode, Kaila and Kyle discuss their thoughts on the age-old question: is it ever okay to be emotional at work? Listen to hear their anecdotes of crying with colleagues, surface acting vs. deep acting, and why they think emotional intelligence is so crucial at this point in time. 

00:00 Intro

04:26 The aim of this episode

07:27 Affective Events Theory

09:53 Primal Leadership by Daniel Goleman 

14:15 Is going with your gut an example of being emotional?

17:33 The contagious effect of emotions

20:42 Crying at work

25:16 Surface acting vs. deep acting

27:42 The gender disparity when it comes to emotions in the workplace

29:57 Tactics

32:20 Per YOUR Last Email

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 [email protected]

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

In this episode, Kaila and Kyle revisit the topic of AI (2 years after their first episode on the topic) and discuss the major objections to AI, how the perception of the technology has changed recently, and the best ways to use it to enhance your work.

00:00 Intro

01:27 How our perceptions of AI have changed in the past 2 years

03:56 The shifting public perception of AI - efficiency vs. enhancement

12:38 First objection to AI - environmental concerns

18:13 Second objection to AI - it’s weakening our ability to think

22:08 Third objection to AI - the controversy over the way AI was trained

23:41 Use cases and tactics

31:44 The most common error Kyle sees people making with AI

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 [email protected]

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

In this episode, Kaila and Kyle share their predictions for work and work culture in 2026. From “job kissing” to the careers we think might be eliminated in 2026, you’re not going to want to miss this episode. 

00:00 Intro

01:48 Prediction #1: Slight imperfections will be a sign of effort

06:06 Prediction #2: There will be a premium on being able to explain the business impact of your work

08:50 Prediction #3: “Job kissing”

13:06 Prediction #4: Your degree and your network will matter more than ever before

17:18 Prediction #5: The two career paths that won’t exist by 2027

23:54 Prediction #6:  Career growth is going to become a lot harder 

27:12 Bonus Wackadoodle predictions

28:32 Per My Last Policy

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 [email protected]

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

In this episode, Kaila and Kyle discuss uncertainty at the individual, external, and societal level, and share their best strategies for managing and coping with the anxiety that comes with it. 

00:00 Intro

03:08 Addressing uncertainty on the individual level

08:57 Kyle’s bucketing approach for tackling uncertainty

15:23 Dealing with external, corporate-level uncertainty

22:28 Discussing uncertainty at the societal level

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 [email protected]

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

In this special bonus episode, Kaila and Kyle sit down with Industrious president Anna Squires Levine to discuss the role that connection plays at work, the future of offices and hybrid vs. remote work, the role of leadership in the modern workplace, and advice on making career pivots.

00:00 Intro

01:16 University of Chicago Booth School of Business study on human connection

07:45 What most companies get wrong about how to design a great working environment

10:31 Advice for companies trying to introduce more fun into their culture 

12:42 How should leaders think about creating a great workplace given the mixture of hybrid, remote, and in-office employees?

15:57 Game: Ask Anna

22:43 How Anna approaches building a culture of energy (vs. one of burnout)

25:37 Anna’s advice for those looking to make a career pivot

29:47 What parenting has taught Anna about navigating work

This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour. 

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 [email protected]

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

In this episode, Kaila and Kyle get into personal finance—the money lessons they learned the hard way throughout their careers, and how they approach managing their savings, investments, and spending now.

00:00 Intro

02:36 A big wake-up call money moment in Kaila’s life

07:27 Kyle’s big wake-up call money moment

10:21 Kaila’s experience with lifestyle creep

13:56 An important salary negotiation in Kyle’s career 

18:10 Learning to how to spend based on your values

21:40 Structuring your compensation

25:18 How Kaila and Kyle structure their savings and personal finances

This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour. 

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 [email protected]

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

In this episode, Kaila and Kyle share the productivity tips that help them accomplish their to-do list, and to get your 2026 off to a strong start. 

00:00 Intro

02:20 Kaila’s and Kyle’s word of the year

04:30 Productivity tip #1: The Sunday Setup

09:29 Productivity tip #2: The Bullet Journal

13:06 Productivity tip #3: Commit to S***

16:57 Productivity tip #4: Lean into the Eustress Curve

19:09 Productivity tip #5: Time Block the Bull****

22:20 Productivity tip #6: Create Boundaries Around Your Energy

25:18 Productivity tip #7: The Great Filter

26:03 Bonus listener question

This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour. 

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 [email protected]

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

In this episode, Kaila and Kyle discuss why there is a fear of being “left behind” in the workplace in 2026, and what you can do to avoid that outcome. 

00:00 Intro

02:08 Where the “left behind” framing is coming from

04:19 The “K-shaped” economy

09:02 Kyle’s hot take prediction on 2026

13:58 How to set yourself up for success in 2026

16:50 How Kaila and Kyle have started incorporating AI into their workflows

23:14 An example of how AI proved to be incredibly helpful in Kaila’s work

25:52 Another key tip for not falling behind in 2026

28:22 Extreme prioritization

31:09 The parable of the farmer

This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour. 

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 [email protected]

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