Episodes

Dec. 15, 2025

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 an...

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Dec. 8, 2025

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...

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Dec. 1, 2025

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 ad...

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Nov. 24, 2025

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 cultur...

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Nov. 17, 2025

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 ent...

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Nov. 10, 2025

Am I The A**hole? The Credit Thief, The Scrooge Boss, and The Office …

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 dram...

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Nov. 3, 2025

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 th...

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Oct. 27, 2025

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 h...

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Oct. 20, 2025

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 actionabl...

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Oct. 13, 2025

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 W...

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Oct. 6, 2025

From “Yes Man” Bosses to Conflicting Feedback: We Answer Your Career …

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 ...

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Sept. 29, 2025

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 i...

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Sept. 22, 2025

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 po...

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Sept. 15, 2025

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 ...

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Sept. 8, 2025

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. 00:0...

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Sept. 1, 2025

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 c...

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Aug. 25, 2025

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 ...

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Aug. 18, 2025

Can You Get Wealthy With Just Your 9 - 5?

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...

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Aug. 11, 2025

Balancing Friendship Inside & Outside of Work, with Morning Brew Dail…

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 ...

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Aug. 4, 2025

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. patern...

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July 28, 2025

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. 00:0...

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July 21, 2025

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 ...

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July 14, 2025

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...

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July 7, 2025

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 extri...

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