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 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
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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
We Made You a Report Card for Your Job – Here’s Why
In this episode, Kaila and Kyle talk about the value of giving your job its own performance review, the most effective way to do it, and the lowest rated jobs from their own career experiences.
Get your copy of the Rate Your Job Template here!
00:00 Intro
06:46 The Rate Your Job Template
13:38 Explaining the template through an example
15:55 How Kaila used the Rate Your Job Template when
When A Side Hustle Is (and Isn’t) Worth It
In this episode, Kaila and Kyle dive into what exactly constitutes a “side hustle”, and the circumstances in which it IS and ISN’T worth having one. Not all side hustles are created equal.
00:00 Intro
03:11 Average income earned from a side hustle
05:11 The issue with the term “side hustle”
08:00 The most common types of side hustles
14:45 “Acceptable or Not?” game
20:46 Considering how a side hu
Can You Recession-Proof Your Job?
In this episode, Kaila and Kyle dive into tips and tactics on the best way to protect your job and prepare yourself for potential job cuts during a recession.
00:00 Intro
00:27 Listener email
03:19 What happens during a recession
06:24 What you can do to prepare yourself professionally if you are currently employed
09:10 “T-Shaped skills”
13:45 The importance of weak ties
19:09 Why you should con
Can You Be TOO Efficient at Work?
In this episode, Kaila and Kyle discuss the reason why efficiency shouldn’t be the goal at work, and how to actually get better at your job.
00:00 Intro
00:41 Our obsession with efficiency
02:26 The problem with the conversation around AI
06:46 What you lose when you focus too much on efficiency
11:42 When Kaila over-focused on efficiency in her career
18:06 How to actually get better at your job
Tackling Difficult Conversations with Erin McGoff
In this episode, Kaila and Kyle discuss how to have those difficult conversations at work with career advice expert Erin McGoff of @advicewitherin. From addressing your lazy coworker to handling your micromanaging boss, Kaila, Kyle, and Erin offer specific tactics and approaches for conducting these challenging conversations.
00:00 Intro
00:55 How Advice With Erin got started
03:49 Stats on how m
We React to Corporate Espionage: Rippling v Deel
In this episode, Kaila and Kyle dig into the details of the Rippling v Deel corporate espionage lawsuit, and why—even if you aren’t a corporate spy yourself—it should matter to you.
00:00 Intro
00:51 Background
07:26 Our reaction to the Rippling v Deel case
12:36 Remembering what Slack really is
18:08 What kind of information is okay to take with you from a job, and what is not
20:11 Noncompete c
Are You a Bad Person If Your Job Doesn't Align With Your Values?
In this episode, Kaila and Kyle get philosophical and discuss the ethics of working for a company that doesn’t align with your values. Is it ever acceptable to work at a job that you perceive as immoral? And what can you do if you have to work at such a place?
00:00 Intro
05:30 Whether or it’s morally okay to work somewhere that goes against your values
09:08 Another important caveat when it come
Is Nepotism In The Workplace Actually Bad?
In this episode, Kaila and Kyle discuss the difference between nepotism vs. networking in the workplace, and how to make nepotism work for you even when you don’t think you have the connections you need to secure an opportunity.
00:00 Intro
00:46 Defining a “nepo baby”
04:54 How common workplace nepotism actually is
09:03 When people are, and are not okay with workplace nepotism
12:52 Is nepotism
Are Millennial Managers Too “Soft?”
In this episode, Kaila and Kyle discuss whether or not millennial managers are too soft, the different styles of management, and how to navigate giving tough feedback.
00:00 Intro
02:29 How Kaila and Kyle define a “millennial manager”
07:49 The difference between a good millennial manager and a bad millennial manager
10:08 Previous generations vs millennials in terms of management styles
15:08 “P
Am I The A**hole? Revenge Quitting, Work Frenemies, and More
We’ve done it again—this week Kaila and Kyle read and respond to your “am I the a**hole?” submissions around your work-specific situations…and they do not hold back.
00:00 Intro
01:02 AITA scenario 1 | vengeful quitter
05:37 AITA scenario 2 | “friend” exploitation
09:57 AITA scenario 3 | senior exec’s personal tragedy
14:44 AITA scenario 4 | Reddit submission
Want to get all of Kaila & Kyle’s ca
What Do DEI Rollbacks Mean For You?
In this episode, Kaila and Kyle discuss the recent headlines around DEI, the potential implications of these measures, and what actually makes the most effective teams.
00:00 Intro
00:43 Recent headlines around DEI
06:05 Listener email
12:04 Stats around DEI from Morning Brew’s Insights and Analytics team
16:34 Why having a diverse workforce helps your business outcomes
20:04 An example of DEI e
The Best Tips for Negotiating a Higher Salary, with Salary Transparent Street
In this episode, Kaila and Kyle are joined by Hannah Williams, founder and host of @SalaryTransparentStreet, to talk about the importance of salary transparency, why it’s still such an uncomfortable thing to talk about, and how to negotiate for a higher salary.
00:00 Intro
00:45 Hannah Williams and Salary Transparent Street
01:24 When Hannah first realized she was being underpaid
07:51 The experi
How to Take an “Adult Gap Year” – and When It’s Not Worth It
In this episode, Kaila and Kyle discuss the pros and cons of taking an “adult gap year” (aka sabbatical or “mini-retirement”), why they’re becoming more common, and how to financially plan for one if you want to take one yourself.
00:00 Intro
01:56 Stats on burnout
05:54 Defining “sabbatical” vs “leave of absence” vs “gap year” or “mini retirement”
08:48 Companies providing sabbatical options
15
We React to Zuck’s “Masculinity” Comments and Meta’s Big Layoffs
In this episode, Kaila and Kyle discuss some of the recent news surrounding Meta—from their announcement of cutting 5% of their workforce, to Mark Zuckerberg’s recent comments on masculinity in the workplace.
00:00 Intro
00:51 Meta’s recent announcement around firing practices
04:25 Two potential upsides to Meta’s “rank and yank” system
07:07 Issues with stack ranking systems
13:39 What is the i
The Right Way to Make a Major Career Change
In this episode, Kaila and Kyle discuss when and how to make a career pivot, and the questions to ask yourself before starting.
00:00 Intro
01:19 Listener career pivot story submission
05:06 Kaila’s biggest career pivot
07:55 A crucial consideration before making a career change
08:21 Kyle’s career pivots
12:13 The importance of finding what you actually enjoy doing
15:54 A common mistake with ne
Is 2025 The Year of “Revenge Quitting”?
In this episode, Kaila and Kyle discuss the rise of revenge quitting, what it is, why it’s seemingly on the rise, and their takes on its effectiveness.
00:00 Intro
01:43 Defining what “revenge quitting” is
04:05 Why 2025 will be the year of revenge quitting
09:30 Why the year of revenge quitting might actually be something else
10:37 Why Kaila loves the idea of revenge quitting
16:35 The truth ab
How to Get Promoted This Year
In this episode, Kaila and Kyle discuss the real strategies and steps involved in getting a promotion, from how and when to have the conversation with your boss, to how to get clear for yourself what you really want in the next stage of your career.
00:00 Intro
00:36 Kaila and Kyle’s first promotions
05:38 Kaila and Kyle’s 2025 career goals
07:12 The number one thing you should be doing to set yo
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