Per My Last Email

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/ 

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@PerMYLastEmailShow

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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!

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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