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

In this episode, Kaila and Kyle discuss how AI is starting to impact how we communicate with one another at work. There are both obvious and subtle ways in which the technology is affecting how we speak, and Kaila and Kyle have some strong feelings about it. 00:00 Intro 00:18 The problem 04:04 How we got here 09:41 The inciting concern about how we talk to chatbots  13:05 Another communication heuristic that has been altered by AI 15:56 How using AI can be corrosive to work relationships 21:11 The linguistic tip-offs that signal something might have been written by AI 23:35 Another way that AI is changing how we speak 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 dig into the unexpected ways in which work impacts our mental and physical health, and provide some tactics for how to avoid some of these health risks whether you work remotely or in an office.  00:00 Intro 02:22 Remote work and unhappiness 09:28 Kaila’s hot take on remote work 11:27 Tactics to avoid the pitfalls of remote work 16:00 The impact of work on our physical health 18:55 The thing impacting our health more than sitting all day 22:08 Why going into the office (vs working remotely) might be healthier overall 24:13 Middle Manager-itis 29:54 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 are joined by Tech Brew’s editor Saira Mueller to discuss current and emerging tech trends—from AI to surveillance technology—and how they’re impacting the workplace, and what we can do to improve our own work environment with them (or in spite of them).  00:00 Intro 01:39 How AI use has trended in the workplace 11:14 The AI software that has most impressed Tech Brew’s editor 12:24 The tech trends that have emerged with RTO (return to office)  15:33 Surveillance technology 18:47 The other reason companies use surveillance technology 21:44 Technology backlash and how to unplug  29:54 Game: Signal or Noise 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 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 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 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 to see changed about the hiring process 13:25 The anti-sell interview 15:29 The most important skill to develop as an early career professional 18:41 Advice for the transition into mid-career 23:37 What C-suite level professionals should be focused on 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 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 your own level of ambition 31:46 Work Rants 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 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 Labs is an example of useful constraints 14:48 Can removing constraints ever be beneficial? 19:31 How do we build a constraint to prevent distraction? 23:49 David’s observations on AI’s impact on human productivity  27:30 Creativity and the Green Eggs and Ham Effect 31:07 What is the relationship between creativity, expertise, and constraints? 35:08 Is having unlimited professional options actually good career advice? 39:28 Decision-making and Fredkin’s Paradox  41:00 How David’s two books Range and Inside the Box tie into one another 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 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 posting too much and posting too little 23:50 Should phones be banned from the office? 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 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 portfolio career? 23:06 How Milly is thinking about AI 27:03 Is it more beneficial in the long run to be a generalist given the AI boom? 31:57 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 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 granola.ai/brew to try it today for FREE.  Find Granola-generated notes on this episode here: https://notes.granola.ai/t/a9006ea5-1bbd-41d5-855f-b456a44d2822-009c2hma 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