Recent Episodes

The Rise of the Career Generalist (and Why It Matters More Than Ever)
June 1, 2026

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 sta...
Retirement Has Changed—Here’s How to Plan For What It’s Really Like
May 25, 2026

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 01:3...
Why “Optimization” Is Actually Making You Miserable
May 18, 2026

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 n...
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...

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