Episodes

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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June 30, 2025

Am I the A-Hole? Coworker Gifts, Applying for the Same Job As Your Fr…

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...

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June 23, 2025

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...

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June 16, 2025

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 ...

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June 9, 2025

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 0...

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June 2, 2025

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 Ple...

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May 26, 2025

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...

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May 19, 2025

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 ...

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May 12, 2025

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...

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May 5, 2025

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 pr...

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April 28, 2025

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 ...

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April 21, 2025

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 ear...

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April 14, 2025

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 reces...

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April 7, 2025

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 conversat...

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March 31, 2025

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...

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March 24, 2025

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 reac...

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March 17, 2025

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 i...

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March 10, 2025

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 opportuni...

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March 3, 2025

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...

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Feb. 24, 2025

Am I The A**hole? Revenge Quitting, Work Frenemies, and More

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Feb. 17, 2025

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 List...

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