Recent Episodes

Should You Be Friends With Your Boss? + 3 More Career Dilemmas
May 11, 2026

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 addre...
The Hidden “BS” Holding You Back at Work (And How to Break It)
May 4, 2026

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, ...
The 5 Sneaky Ways You Might Be Sabotaging Your Career
April 27, 2026

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 Tact...
Meetings Suck—Here are the Science-Backed Ways to Fix Them
April 20, 2026

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—...
Should You Flex at Work? The Career Math Behind Showing Wealth
April 13, 2026

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 ...
Why AI Isn’t Killing Jobs (And What It’s Actually Changing)
April 6, 2026

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...

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