Episodes

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...

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...

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...

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 ...

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...

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...

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 ...

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...

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...

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 ...

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...

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 ...

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...

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...

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 ...

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...

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...

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...

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...

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 ...

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...

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...

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...

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 ...