The podcast episodes discuss various life milestones, including personal relationships, overcoming adversity, music and memory, family, caregiving, and the challenges of navigating one's twenties.

For example, the episode 'Introducing 'Life in Seven Songs'' explores how influential figures share the songs that have shaped their lives, while 'Your 20s are NOT your best years' delves into the common struggles and uncertainties of the twenties.

Other episodes, such as 'It Sucks to Be 33' and '"Can I Have a Wedding When I'm In Debt?"', examine the economic and financial implications of life milestones, including homeownership, marriage, and starting a family.