How to Be an Adult

How to Be an Adult


How to Ask Yourself Great Questions (Ep. 24)

April 22, 2025

The questions we ask ourselves determine which thoughts subsequently enter our minds. If we ask ourselves about counterfactual scenarios, our mind floods with counterfactual scenarios. If we ask ourselves about reassuring truths, we find reassuring truths, almost as though we were typing a query into a search engine. This episode is about how to ask yourself the second type of question.



  • Good questions can lead to productive thoughts, while bad questions can evoke unnecessary anxiety and confusion.
  • The way we think is influenced by the questions we ask ourselves, which can shape our emotional and physical well-being.
  • It’s essential to challenge the premises of our questions, as flawed assumptions can lead to unhelpful answers.
  • Questions about others’ opinions or actions distract from our agency; instead, focus on self-directed questions using “shall” to emphasize personal responsibility.
  • Using frameworks like the five W’s (who, what, when, where, why) and strategic versus tactical questions can guide effective self-inquiry.
  • Intuition plays a crucial role in decision-making; allowing time for reflection can lead to more satisfying answers than immediate rational thought.
  • Individuals should prioritize asking themselves questions about their own values and priorities rather than seeking validation from others.
  • Recognizing one’s agency in decision-making can reduce anxiety and empower individuals to shape their futures.
  • The ultimate goal of questioning is to approach truth and broaden perspectives, leading to actionable insights and improved self-awareness.

Table of Contents:


0:00 – Intro

0:55 – Why good questions matter

8:26 – “What if” and “why” questions

13:36 – The purpose of a question

19:25 – The 5 W’s and H

24:42 – Let questions sit


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