Per My Last Email
Each week on Per My Last Email, Morning Brew's resident career experts Kaila and Kyle debate the trickiest challenges in work life, such as asking coworkers about salaries, whether Gen Z is set up for failure in the workplace, and if you should bring your whole self to work. They share tactics on how to overcome these challenges, drawing from their collective experience across corporate, government, nonprofit, and startup sectors.
Episodes
The Trap of Success: Why Working at a Successful Company Can Hurt Your Career
In this episode, Kaila and Kyle discuss the potential career pitfalls of working at a successful company, and how to avoid the “trap of success” when you do.
00:00 Intro
03:53 Kaila’s experience of leaning on Morning Brew’s success
06:52 Why it’s easy to get lazy at a successful company
09:19 The traps to be aware of at a successful company
14:45 How potential employers should analyze c
Busting Myths About Millennials at 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 for a funny and insightful conversation around millennials at work—the stereotypes, the myths, the areas of strength and the areas that could use some improvement.
00:00 Intro
01:12 What distinguishes millennials from Gen Z
07:57 Millennial myth: millennials are job hoppers
11:36 Millennia
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 “enshittificatio
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
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
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
6 Habits to Steal From the Most Successful Leaders
In this episode, Kaila and Kyle talk about the habits they’ve observed in the most effective and successful leaders they know, and how to incorporate them into your own work life. (And let’s just say a few of them are a bit controversial.)
00:00 Intro
02:31 Habit #1
08:50 Habit #2
12:38 Habit #3
17:59 Habit #4
21:18 Habit #5
24:32 Habit #6
This episode was spo
Am I the A**hole? Clapping Back at Work, Refusing a Referral and More
In this episode, Kaila and Kyle bring you another round of a fan favorite: Am I The A******? Listen to hear Kaila and Kyle react to some of the wildest, work-related AITA posts on Reddit, and weigh in with their professional advice.
00:00 Intro
00:25 Scenario 1 | Clapping back at a coworker
06:41 Scenario 2 | Office desk assignment
12:44 Scenario 3 | Job referral
18:27 Scenario 4 | Cove
4 Types of Networking You’re Probably Ignoring
In this episode, Kaila and Kyle dig into the more subtle (but incredibly important) forms of networking that you might not be thinking about. Whether it’s honing your personal brand or expanding your weak ties, Kaila and Kyle share some excellent tips on the more unexpected ways to network.
00:00 Intro
00:39 Kaila’s experience with back-channeling
04:26 Peer-to-peer networking
10:5
BONUS: The Career Advice We Wish We Knew in Our 20s (Live)
In this special bonus episode, Kaila and Kyle tape their very first live episode at Verizon HQ in Basking Ridge, New Jersey. Listen to hear Kaila and Kyle share what they learned from their own early career experiences with Verizon’s intern class (aka VTerns), as well as hear professional insights and advice from Christina Schelling, Verizon’s own SVP of Human Resources (whose early career experie
Why “Good Enough” Is Better for Your Career
In this episode, Kaila and Kyle discuss why perfectionism is actually a negative at work (and in life), and how to overcome it. And as a self-proclaimed recovering perfectionist, Kaila offers some excellent tactics and tips.
00:00 Intro
01:48 The misconception about perfectionism
06:16 The impacts of perfectionism
14:38 On whether we overrate intelligence
16:22 Measuring the delta betwe
The Most Overrated Work Perks (And the Ones You're Ignoring)
In this episode, Kaila and Kyle dig into and debate the most overrated and underrated work perks, and how to make the most of the ones you’re probably overlooking. Summer Fridays? Education credits? Unlimited PTO? You might be surprised by some of their controversial takes.
00:00 Intro
00:14 Reviewing the Morning Brew company party
05:09 Kaila’s party strength vs. Kyle’s party strength
0
Coworker Pet Peeves: What We Hate and What We Love
In this episode, Kaila and Kyle list the most annoying and the most appreciated qualities in a coworker. Plus, how to make the most of those good qualities and navigate the grating ones.
00:00 Intro
01:08 Coworker pet peeve #1
06:02 Coworker pet peeve #2
10:15 Coworker pet peeve #3
12:50 Coworker pet peeve #4
15:23 Coworker green flag #1
19:19 Coworker green flag #2&
AI Is Changing How We Talk to Each Other...And It's Annoying
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 communi
The Workplace Habits That Are Quietly Hurting Your Body & Brain
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
The Workplace Tech Trends You Can't Ignore (AI, Surveillance & RTO)
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
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 Settin
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 th
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 think
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 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 Bel
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 no
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 abo
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 retire
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. 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 b
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 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
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 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
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 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 Ta
Meetings Suck—Here are the Science-Backed Ways to Fix Them
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
Should You Flex at Work? The Career Math Behind Showing Wealth
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
Why AI Isn’t Killing Jobs (And What It’s Actually Changing)
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
You Survived a Layoff…Now What? (The Truth No One Tells You)
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
Inside the Recruiter’s Brain: How to Get Hired in the Age of AI
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 recr
From Happy Hour to Zyn: Navigating Drug Culture at the Office
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 dri
The 100th Episode Special: Work News, Gen Z & an HR Performance Review
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
Why You Should Stop Chasing Money and Start Chasing Obsession, with Bill Gurley
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 o
Why Emotional Intelligence is More Important Than Ever at Work
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
AI at Work: What We Got Wrong (And the Use Cases That Actually Work)
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. enhanc
Job Kissing, AI Slop, and Our Work Life Predictions for 2026
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:
Everyone Feels Uncertain at Work Right Now—Here’s How to Handle It
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 unce
BONUS: What Makes a Workplace People Actually Love?
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 com
The Biggest Money Mistakes of Our Careers – and How You Can Avoid Them
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 negotiati
Commit to Sh*t: The Productivity Advice No One Tells You
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
Why So Many Workers Will Fall Behind in 2026 (And How Not To)
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 in
The 5-Step Goal-Setting System to Getting Promoted in 2026
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 S
We Argue, We Rant, We Recap 2025: A PMLE Holiday Spectacular
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,
The 4-Step Guide to Acing Your End of Year Review
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
BONUS: Joel Kim Booster Gives Us His Holiday Hot Takes
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 h
Work Will Always Affect Your Personal Life – Here’s How to Control It
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
How to Be Less Online (While Your Job Still Needs You Online)
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 det
The Worst Career Advice You’re Still Taking (And What to Do Instead)
In this episode, Kaila and Kyle break down and debate the worst career advice they’ve ever heard, and what they think you should do instead.
00:00 Intro
02:45 Bad advice #1
09:28 Bad advice #2
16:28 Bad advice #3
23:30 Bad advice #4
27:50 Work rant
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 M
Everything’s an Emergency: The Rise of Workplace Crisis Culture
In this episode, Kaila and Kyle dig into “crisis culture” at work—what it is, how it came about, and what you can do about it if you’re experiencing it in your own workplace.
00:00 Intro
01:35 What is “workplace crisis culture”?
02:35 Why is this crisis culture happening?
09:49 How crisis culture has affected Kaila’s career
14:42 Kyle’s own experience with crisis culture
19:14 Another way t
So You Want to Be Your Own Boss? Here’s What It’s Really Like
In this episode, Kaila and Kyle sit down with journalist, media executive, entrepreneur, and NKA Media founder Nora Ali to talk about the realities of becoming your own boss. Nora gets extremely candid about what pursuing entrepreneurship really looks like in detailing her transition from the traditional 9 - 5 to founding her former startup Mason Media.
00:00 Intro
02:09 Nora’s career trajecto
Am I The A**hole? The Credit Thief, The Scrooge Boss, and The Office Narc
In this episode, Kaila and Kyle give their strong and uninhibited opinions on some more spicy work-related AITA Redditor submissions. From refusing to cover for colleagues to reporting them to HR, this episode brings the drama.
00:00 Intro
02:23 Scenario #1 - The Credit Thief
09:35 Scenario # 2 - The Scrooge Boss
17:02 Scenario #3 - The Shady Firm
21:54 Scenario #4 - The Office Narc
This ep
Co-CEOs, No Managers, and Zero Loyalty — How to Navigate “Work 2.0”
In this episode, Kaila and Kyle discuss the demise of the traditional corporate structure—from co-CEOs, to the elimination of middle managers, and even the death of workplace loyalty. It seems like everything we know about the way companies are organized are changing, so what does this mean for you?
00:00 Intro
01:43 What’s unique about this moment in time for workplaces
04:36 A possible explan
5 Life Experiences That Unexpectedly Make You Better at Your Job
In this episode, Kaila and Kyle discuss the pivotal life experiences that helped them in their careers in unexpected ways. Listen to hear Kaila and Kyle’s personal stories of rock-bottom moments and personal epiphanies that have ultimately made them better at their jobs.
00:00 Intro
03:13 Kyle’s biggest experience with failure
08:06 Kaila’s biggest experience with failure
11:54 The non-work th
The Great Lock-In: How to Crush Q4 and Finish the Year Strong
In this episode, Kaila and Kyle break down “The Great Lock-In”—the Q4 period where it’s advantageous for your year-end review to focus and get down to business. Listen to hear Kaila and Kyle’s extremely tactical and actionable advice on how to accomplish the most before the end of the year.
00:00 Intro
02:01 What “The Great Lock-In” is about
07:17 The first phase of “locking in”
13:14 The seco
Here’s What to Do If You Get a ‘Quiet Promotion’
In this episode, Kaila and Kyle discuss the rise of the “quiet promotion,” how to know whether or not you’re receiving one, and what to do if you have.
00:00 Intro
01:50 “job hugging”
07:42 Defining “quiet promotions”
10:12 Why quiet promotions are happening
13:40 Kaila’s experience with quiet promotions
15:28 Kyle on whether he’s been quiet promoted
17:41 What to do if YOU’RE being quiet
From “Yes Man” Bosses to Conflicting Feedback: We Answer Your Career Advice Questions
In this episode, Kaila and Kyle are responding to listener-submitted career advice questions…and they’re juicy! From how to handle conflicting feedback to wading through the “work fluff”, this episode is chock-full of useful tactics for handling tricky work situations.
00:00 Intro
01:25 Grab Bag Question #1 - communication issues
06:38 Grab Bag Question #2 - conflicting feedback
12:50 Grab Bag
Is Dating Your Coworker Ever Worth It?
In this episode, Kaila and Kyle debate whether you should or should NOT pursue your office crush. That’s right—we’re talking office romance this week, and Kaila and Kyle hold strongly opposing positions on the matter, based in part on their own personal experiences.
00:00 Intro
02:57 Historical context for the conversation
04:23 Kaila’s opinion on pursuing a relationship in the workplace
08:19
Is it Cringe to Try Hard at Work?
Is it cringe to try too hard? In this episode, Kaila and Kyle are joined by Normal Gossip co-creator and Defector Media co-owner Alex Sujong Laughlin to talk about the ins and outs of being a “try hard” at work. Alex’s new podcast, Try Hard, documents people attempting things that they’re afraid to do, and in this episode you’ll hear about a couple of moments when Alex and Kaila’s fear of being cr
Why Middle Managers Matter More Than You Think
In this episode, Kaila and Kyle discuss the current trend of laying off middle managers and the flattening of organizations, the impact this can have on individuals, and why we can’t forget the key roles that middle managers have in your career.
00:00 Intro
01:43 Who are the middle managers?
04:15 Stats illustrating the decline of the middle manager
06:40 How an absence middle managers can hin
How to Survive in an AI-Dominated Job Market
In this episode, Kaila and Kyle discuss how AI is impacting the job market, what the future of work may look as more roles and industries become automated, and how to stand out in the age of AI-assisted hiring processes.
00:00 Intro
01:41 Research on the impact of AI on job seekers
06:28 The rise of the “he-cession”
10:07 How AI is impacting the job hunt for mid-career level individuals
14:02
How to Navigate a Toxic Work Environment
In this episode, Kaila and Kyle discuss the three most problematic toxic workplace scenarios, and how to manage each of them. Plus, wait ‘til the end to hear a bonus fourth toxic workplace scenario that you probably haven’t considered.
00:00 Intro
01:42 Defining “toxicity” in the workplace
04:14 Stats on toxic workplaces
05:43 Toxic coworkers and how to handle them
11:46 How Kaila handled a
The Leadership Traits the Top 1% of Executives Use to Climb the Ladder
In this episode, Kaila and Kyle get educated on the four most important qualities of leadership that separate the top 1% of executives from the rest. Cassie Young, General Partner at Primary Venture Partners, joins Kaila and Kyle this week to discuss why these are the most important (and underappreciated) leadership traits, and why it’s important to know them even if you’re not a leader yourself.
Can You Get Wealthy With Just Your 9 to 5 Job Anymore?
In this episode, Kaila and Kyle are discussing whether or not you can actually get wealthy in your 9 - 5 alone anymore. Is the American Dream dead, or just evolved? Listen to hear their takes on the best types of companies to work for if you want to build wealth without the side hustle.
00:00 Intro
01:40 How money has played a role in career motivation for Kaila
04:14 How money factored into Ky
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.
What Parental Leave is Actually Like
In this episode, Kaila and Kyle discuss Kyle’s experience of paternity leave so far, what’s been the most surprising to him, and how he’s feeling about returning to his 9 to 5.
00:00 Intro
01:32 Stats on maternity vs. paternity leave in the U.S.
05:02 Research on the impact of taking paternity leave on a father’s brain
08:11 How pat leave has been for Kyle
13:53 Kyle’s feelings around retur
Business IS Personal, and Other Non-Obvious Truths
In this episode, Kaila and Kyle debate what they consider to be some non-obvious but very real truths about the nature of work and career. Plus, listen ‘til the end of the episode to hear Kaila’s bonus productivity hack.
00:00 Intro
00:26 “Per YOUR Last Email” segment
02:32 Non-Obvious Truth #1
05:30 The 3 “right” ways to be exploited at work
11:35 Non-Obvious Truth #2
19:33 Non-Obvious Tru
The 4 Types of Jobs Everyone Should Experience at Least Once
In this episode, Kaila and Kyle discuss and debate the four types of jobs that they think everyone should have at least once in their career. Plus, listen ‘til the end to hear Kaila’s work fail of the week.
00:00 Intro
01:06 Job #1
06:21 Pros and cons of working for a name brand
10:54 Job #2
20:04 Job #3
23:44 Job #4
29:32 Sequencing your career trajectory
32:08 Kaila’s work fail of
Why Office Politics Can Actually Be a Good Thing
In this episode, Kaila and Kyle discuss the ins and outs of office politics, what it REALLY is, and how to improve on your office politicking skills in order to advance your career.
00:00 Intro
03:09 The two buckets of office politics
07:48 Can you opt out of office politics?
10:24 Advice for groups who face more biases in the workplace
12:57 MIT study on promotions based on potential
15:07
How to Motivate Yourself – Even When You’re Burned Out
In this episode, Kaila and Kyle discuss the difference between extrinsic and intrinsic motivation, and how to artificially generate it when you find yourself lacking motivation.
00:00 Intro
00:51 Intrinsic motivation vs extrinsic motivation
03:08 Kyle’s intrinsic motivation vs Kaila’s extrinsic motivation
08:56 How Kaila hacks her motivation
14:52 Research-backed strategies for increasing mo
Am I the A-Hole? Coworker Gifts, Applying for the Same Job As Your Friend, and More
In this episode, Kaila and Kyle dive into some conversation-sparking Reddit “Am I the A******?” submissions, and give their candid opinions on each. From whether or not you should share details of your personal life with your coworkers, to the ethics of applying for the same job as a friend, Kaila and Kyle bring some strong opinions.
00:00 Intro
00:53 Scenario #1 - Retirement Gift
05:14 Scenar
How to Handle Failure Like a Pro
In this episode, Kaila and Kyle talk about their biggest work fails, a different way to think about failure beyond simply as a “learning opportunity,” and share tactics on how to best move through and recover from failures in both work and career.
00:00 Intro
00:40 Kaila’s biggest work failure
04:20 Kyle’s biggest work failure
09:34 The problem with “I don’t fail, I either win or I learn.”
17
Why “High Agency” Might Be the Secret to Growing Your Career
In this episode, Kaila and Kyle discuss what having high agency at work really means, the problems having high agency poses in certain contexts, and how to cultivate more of it in order to help your career.
00:00 Intro
01:20 Defining what having “high agency” is
06:52 The elements of high agency
10:34 An important point about having agency
14:17 An important element of truly effective high
On Steve Madden’s Viral Interview and Politics in the Workplace
In this episode, Kaila and Kyle discuss the viral Steve Madden interview and debate whether CEOs and corporations should be expressing their political views, as well as how to navigate politics in the workplace.
00:00 Intro
01:24 Steve Madden’s viral Cutting Room Floor interview
06:26 Lulu Cheng Meservey on “going direct” as a business leader
07:29 Stats on how different generations feel about
Is People Pleasing Holding Your Career Back?
In this episode, Kaila and Kyle dive into the problems with being a “people pleaser”, and how to balance being agreeable enough while also being effective and impactful at work. Plus, Kaila introduces The Workplace People Pleasing Matrix.
00:00 Intro
00:44 Defining what “people pleasing” actually is
01:55 Why the term “people pleaser” is inflammatory
06:09 Stats on agreeableness and income
0
Everything You Know About Work Stress is Wrong
In this episode, Kaila and Kyle discuss work stress and whether we’ve been thinking about it in the wrong way. There’s clearly such a thing as too much stress, but what about too little? And is there an ideal amount of stress we should be aiming for in order to be most successful at our jobs?
00:00 Intro
00:24 APA stats on stress and anxiety
02:53 Kaila’s relationship with work-related stress
Busting Myths About the Most Common Career Cliches
In this episode, Kaila and Kyle discuss common career tropes and debate whether or not the sayings hold up. Is HR really not your friend? Are your connections more important than your skills? Listen and find out.
00:00 Intro
00:36 Career myth #1 - “No one knows what they’re doing.”
07:35 Career myth #2 - “HR is not your friend.”
12:51 Career myth #3 - “It’s not WHAT you know, it’s WHO you know
How to Be Happier at Work, with Dr. Laurie Santos
In this episode, Kaila and Kyle are joined by Yale professor and host of The Happiness Lab podcast, Dr. Laurie Santos, to talk about the small ways you can find more meaning in your job, and the adjustments that help increase our happiness and well being at work.
00:00 Intro
00:44 Dr. Laurie Santos Intro
01:47 How much does your work factor into your overall happiness?
03:33 Dr. Santos’ take
Why Is AI So Annoying?
In this episode, Kaila and Kyle discuss the problems with the current conversation around AI, and debate the issues with and the benefits of the technology for the workforce, society, and individuals.
00:00 Intro
00:57 The problem with the discourse around AI
05:42 Why we’re not having good faith arguments around AI
09:43 The three use cases for AI that Kaila found helpful
17:28 Kaila’s conce
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