Per My Last Email

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 cl...

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 th...

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 a...

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 productivity and creativity, and how to implement them on your own to help you in work and life. 00:00 Intro 02:05 The story of General Magic 06:02 Additive bias 09:14 Brooks’s Law 12:34 How Bell Lab...

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 t...

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 s...

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...

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. Also check out Brad’s new book, The Way of Excellence: A Guide to True Greatness and Deep Satisfaction in a Chaotic World. 00:00 Intro 02:08 How Brad define’s “excellence” 05:47 What is “zombie burn...

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 accommodations, this episode addresses a wide range of relatable scenarios.  00:00 Intro 02:56 Question 1 - Can you befriend your boss? 10:37 Question 2 - Can I ask for a raise after a round of layoffs? 15:50...

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 yourself, your colleagues, and even bosses accountable, to freeing yourself of a scarcity mindset, this conversation is packed with practical advice for anyone feeling stuck in their career.  And don’t...

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 important than you think 08:00 Tactics if your commute is negatively impacting your career 11:00 How discussing your AI use can impact your career 17:59 The consequences of being unknown at work 22:27 Tactics...

In this episode, Kaila and Kyle are joined by Rebecca Hinds, PhD, author of Your Best Meeting Ever: 7 Principles for Designing Meetings That Get Things Done. Rebecca breaks down the science behind why meetings so often fail—and shares research-backed tactics to decide which meetings are actually worth having, and how to design them for better outcomes. 00:00 Intro 02:36 Why do meetings suck? 03:47...

In this episode, Kaila and Kyle discuss the politics of displaying wealth at work, and how the perception of it depends on what stage you are at in your career. When does it go from being gauche to cool to flaunt your wealth at the office? And is it ever strategic to appear more or less wealthy than you actually are? 00:00 Intro 01:40 Why we’re discussing wealth at work 04:43 Kaila’s and Kyle’s ex...

In this episode, Kaila and Kyle are joined by LinkedIn Chief Economic Opportunity Officer (and former speech writer for President Obama) Aneesh Raman to talk about why we can be optimistic about AI. Aneesh’s new book, Open to Work: How to Get Ahead in the Age of AI, challenges the notion that AI is the death of entry-level work and instead argues that the technology is simply changing work as we k...

While there is a lot of advice out there about what to do if you’ve been laid off, there isn’t a lot of information for how to manage if you’re one of the lucky (or not so lucky) survivors of a layoff. From being more vulnerable to burnout to taking on more responsibilities, Kaila and Kyle discuss how to handle surviving a layoff both emotionally and professionally, as well as discuss how they nav...

In this episode, Kaila and Kyle are joined by author, speaker, and ZipRecruiter career expert Sam DeMase (@apowermood) to share the best tips for landing a job in the age of AI. From understanding how recruiters think and operate, to structuring your resume for maximum impact, to mastering the “upper third,” this is one episode you don’t want to miss. 00:00 Intro 01:10 What is the life of a recrui...

In this episode, Kaila and Kyle discuss drug culture and how to navigate it when it interacts with your professional life. Should you talk about your weekend marijuana use with your colleagues? Is Zyn use at the office hurting your reputation? And how many drinks should you actually have at the company party? 00:00 Intro 01:23 Disclaimer 04:01 Accepted and normalized drugs 08:17 Navigating drinkin...

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 care...

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 ol...

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 Gol...

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. enhanceme...

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 P...

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 uncertain...

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 compan...

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...