Per My Last Email11 Aug 2025

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

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The Surprising Power of Constraints at Work (with David Epstein)

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...

15 Juni 46min

Following Coworkers on Instagram and Other Social Media Dilemmas

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 ...

8 Juni 34min

The Rise of the Career Generalist (and Why It Matters More Than Ever)

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 gen...

1 Juni 36min

Retirement Has Changed—Here’s How to Plan For What It’s Really Like

In this episode, Kaila and Kyle discuss all things retirement—how the concept of retirement has changed, how they’re financially planning for their own retirements, and what their ideal retirement loo...

25 Maj 36min

Why “Optimization” Is Actually Making You Miserable

In this episode, Kaila and Kyle are joined by author Brad Stulberg to dig into what we get wrong about “excellence,” what true excellence really looks like, and the achievable strategies to achieve it...

18 Maj 39min

Should You Be Friends With Your Boss? + 3 More Career Dilemmas

In this episode, Kaila and Kyle answer listener-submitted questions around career advice and work dilemmas. From just how friendly you should get with your boss to how to ask for remote work accommoda...

11 Maj 32min

The Hidden “BS” Holding You Back at Work (And How to Break It)

In this episode, Kaila and Kyle are joined by Aiko Bethea, Founder of Rare Coaching, to talk about the hidden bullsh*t at work, how it’s holding you back, and what you can do about it. From holding yo...

4 Maj 44min

The 5 Sneaky Ways You Might Be Sabotaging Your Career

In this episode, Kaila and Kyle break down the five sneaky (and surprising) things that are affecting your career, and what you can do about them. 00:00 Intro 02:42 Why your commute is more importa...

27 Apr 37min