Dear Lisa
Dear Abby gives answers. Dear Lisa asks better questions.
The magic isn't: "Here's what you should do." The magic is: "Let's figure out what question you're actually trying to answer."
About the Segment
Dear Lisa is a recurring 10-15 minute segment on The New Reality podcast. Each episode takes an audience-submitted life question — about career, family, money, or relationships — and looks beneath the surface behavior to the motivations and assumptions underneath.
Most advice columns tell you what to do. Dear Lisa helps you understand why you're asking the question in the first place. Because the surface question is rarely the real question.
How It Works
- You submit a question — anything from career dilemmas to money anxiety to relationship crossroads
- Lisa reads between the lines — what's the real question beneath the question?
- The episode explores the assumptions — which inherited beliefs are shaping this situation?
- No prescriptions, just clarity — the goal isn't telling you what to do; it's helping you see what's actually happening
Example Episode
Listener letter:
"We bought our dream house in 2021. Between insurance, taxes, and maintenance it's becoming difficult. We can still afford it, but it feels like the house owns us. Are we failing if we downsize?"
Surface question: Real Estate, Equity, Ownership
Real question: Status, Success, Attachment, Keeping up Appearances
The episode doesn't give a yes-or-no answer about downsizing. Instead, it explores: who told you that the house was the goal? What does "enough" look like now? If no one was watching, what would you actually want?
Submit a Question
Have a question for Dear Lisa? Send it to dearlisa@thenewreality.com. All submissions are anonymous. The question you're afraid to ask is probably the one someone else needs to hear answered.