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

More from Per My Last Email

1. 

   6 Jul 2026 · 32 min

   Does a Real Vacation Even Exist Anymore?

   In this episode, Kaila and Kyle debate whether or not taking a real vacation even exists anymore, and provide tactics for how to protect your off time. Can you ever really fully log off in a world with flexible working conditions? And how can we reclaim PTO? 00:00 Intro 02:20 How we got to the state of the working “vacation” 06:59 The real vs imagined expectations of your employer 11:08 Setting clear expectations with your team 14:32 Flexibility’s pros and cons 21:27 The other reason we can’t fully log off anymore 25:20 Other tactics for getting your vacation time back Want to get all of…

2. 

   29 Jun 2026 · 34 min

   The Career Advice You Need at 25, 35, and 45

   In this episode, Kaila and Kyle are joined by Cherry Miao, CFO of Hightouch, who gets into the art of conducting an effective job interview, how she susses out a job candidate’s mindset, and what she thinks should be changed about the job interview process in general. She also breaks down the skills that are most important to hone in each stage of your career—from your first entry-level job all the way to the C-Suite. 00:00 Intro 01:06 The art of the interview, and how Cherry identifies top talent in interviews 07:27 The blameless retro 09:26 Mindset vs skillset 11:05 What Cherry would like…

3. 

   22 Jun 2026 · 39 min

   How Ambitious Do You Actually Need To Be To Succeed?

   In this episode, Kaila and Kyle are debating ambition: do you really need to be super ambitious to have a successful career? What level of ambition is the ideal amount? And can you be ambitious in both work and life in equal measure? 00:00 Intro 01:21 How we’re defining “ambition” 05:42 Can you succeed without ambition? 13:30 What is the opposite of ambition? 17:05 Kaila’s framework for thinking about the qualities necessary for career success 18:18 How ambitious SHOULD you be? 24:04 Can you be ambitious at work and have some level of work life balance? 27:07 Advice if you’re questioning…

4. 

   8 Jun 2026 · 34 min

   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 is it okay to have no social media presence at all? 00:00 Intro 00:58 Which social platforms you should and should not follow your coworkers on 08:05 A good rule of thumb for deciding whether or not to follow a coworker on Instagram 09:58 The most important thing to keep in mind when it comes to following on social media 18:11 Posting as a form of empowerment 21:32 Finding the balance between…

5. 

   1 Jun 2026 · 37 min

   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 generalists, and how to start building a portfolio career. 00:00 Intro 01:29 Defining what a “generalist” is 02:27 What does a long-term generalist career look like? 04:42 What people get wrong about specialists vs generalists 07:39 How do you figure out your strengths and fit as a generalist? 14:52 What is a “portfolio career”? 21:16 Are there certain personalities that are best suited for a…

6. 

   25 May 2026 · 36 min

   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 looks like. 00:00 Intro 01:33 What does retirement look like right now? 08:48 How Kaila and Kyle approach the financial element of retirement 12:58 Thinking about the non-financial aspects of retirement 22:30 Mini retirements 25:45 Where Kaila and Kyle plan to retire 31:13 Per My Last Policy This episode was sponsored by Granola. Head to granola.ai/brew to try Granola for free. That’s…

7. 

   5 Oct 2026 · 35 min

   The “Enshittification” of Work: Why Your Career Feels Broken

   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…

8. 

   28 Sep 2026 · 36 min

   What Gen Z Really Thinks About Work, Loyalty, and Ambition

   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,…

9. 

   21 Sep 2026 · 24 min

   5 Daily Habits That Could Transform Your Career by Year-End

   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…

10. 

    14 Sep 2026 · 31 min

    The Problem with “Executive Presence”

    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…

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