The Biggest Money Mistakes of Our Careers – and How You Can Avoid Them

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 companies get wrong about how to design a great working environment 10:31 Advice for companies trying to introduce more fun into their culture  12:42 How should leaders think about creating a great workplace given the mixture of hybrid, remote, and in-office employees? 15:57 Game: Ask Anna 22:43 How Anna approaches building a culture of energy (vs. one of burnout) 25:37 Anna’s advice for those looking to make a career pivot 29:47 What parenting has taught Anna about navigating work This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  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 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 Kyle’s career  18:10 Learning to how to spend based on your values 21:40 Structuring your compensation 25:18 How Kaila and Kyle structure their savings and personal finances This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  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 the productivity tips that help them accomplish their to-do list, and to get your 2026 off to a strong start.  00:00 Intro 02:20 Kaila’s and Kyle’s word of the year 04:30 Productivity tip #1: The Sunday Setup 09:29 Productivity tip #2: The Bullet Journal 13:06 Productivity tip #3: Commit to S*** 16:57 Productivity tip #4: Lean into the Eustress Curve 19:09 Productivity tip #5: Time Block the Bull**** 22:20 Productivity tip #6: Create Boundaries Around Your Energy 25:18 Productivity tip #7: The Great Filter 26:03 Bonus listener question This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  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 why there is a fear of being “left behind” in the workplace in 2026, and what you can do to avoid that outcome.  00:00 Intro 02:08 Where the “left behind” framing is coming from 04:19 The “K-shaped” economy 09:02 Kyle’s hot take prediction on 2026 13:58 How to set yourself up for success in 2026 16:50 How Kaila and Kyle have started incorporating AI into their workflows 23:14 An example of how AI proved to be incredibly helpful in Kaila’s work 25:52 Another key tip for not falling behind in 2026 28:22 Extreme prioritization 31:09 The parable of the farmer This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  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 break down their 5-step goal-setting framework that will help you get promoted in 2026.  00:00 Intro 02:17 Step 1 of goal-setting: Get clear on your company’s goals 07:21 Step 2 of goal-setting: Pick a word of the year 10:14 Step 3 of goal-setting: SMART goals 13:47 An important detail of setting SMART goals 17:08 Step 4 of goal-setting: Getting input 20:02 Step 5 of goal-setting: Create a check-in system 25:58 What if your goals are determined for you? This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  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

This week, we’re bringing you a special (and very fun) variety show-style holiday episode. Listen to hear Kaila and Kyle quiz each other on 2025 news trivia, followed by a listener-submitted Am I the A******?, 2025 work rants, and finally our rose, bud, thorn of 2025. 00:00 Intro 01:31 2025 Workplace Trivia 18:26 Listener-submitted “Am I the A******?” Segment 24:12 Work rants 30:36 2025 Rose, Bud, and Thorn This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  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 break down their simple and effective End of Year Reflection Framework, which will help you give the best end-of-year performance review possible.  00:00 Intro 01:55 Kaila and Kyle’s 2025 overall vibe check 04:52 Step one of the reflection framework 08:34 Step two of the reflection framework 16:01 Big takeaways from completing the first two steps of the 4-step reflection framework 19:35 Step three of the reflection framework 27:46 Step four of the reflection framework 34:39 Step five of the reflection framework This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  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 very special bonus episode of PMLE, Kaila and Kyle are joined by comedian, actor, and producer Joel Kim Booster to get his holiday hot takes. Listen to hear how Joel would organize his own office holiday party, the rule he thinks would make corporate America more fun, and his honest opinions in a round of Iconic of Moronic.  00:00 Intro 00:31 What Joel’s performance review would say if he held an office job today 02:02 The most unhinged party theme Joel would institute if he were in charge of the office holiday party 03:09 The office rule Joel would put in place that would make everyone’s work a little more chaotic and a lot more fun 04:34 Rapid Fire Round 09:34 Iconic or Moronic A very special thanks to Cup Noodles for making this episode possible. Follow Cup Noodles to see which lucky Joel Kim Booster fan will receive an office party rescue. 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 both how family has influenced their career paths, how they talk about work with their families, and the importance of figuring out what the right amount of spillover is between work and family life. 00:00 Intro 01:40 How Kaila and Kyle talk about work with their families 07:28 The “spillover-crossover model” 13:19 The danger of co-rumination 15:42 How Kaila’s family influenced her career path 20:34 How Kyle’s family influenced his career path 25:12 Tactics This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  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

Is it possible for us to start to digitally “detox” while still leveling up at work? In this episode, Kaila and Kyle are joined by Kate Noel (host of the podcast People Person, and Morning Brew’s SVP of People Operations) to talk about how we can start to become less dependent on our screens, while still remaining diligent at our jobs.  00:00 Intro 02:53 Should we even be trying to digitally detox? 06:37 How Kate, as an HR leader, is approaching organizational boundary setting 10:55 How to cultivate a boundary-respecting culture within an organization 15:08 How to help cultivate a boundary-respecting culture as an individual contributor 17:27 A different way to think about “work-life balance” 22:12 Should we be on our phones when we’re not working? 27:15 “You don’t rise to the level of your willpower, you fall to the level of your systems.” 32:49 An important thing to consider if you’re feeling overwhelmed at work 34:12 Final tactics for setting better boundaries at work This episode was sponsored by Industrious. Try out Industrious for yourself with a day pass OR a meeting room booking, now 50% off for Per My Last Email listeners. Visit industriousoffice.com/pmle to get your discount or free tour.  Check out People Person here: https://www.podpage.com/people-person/  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