The Power of Understanding Why: Asking Questions with Tom Wheelwright
Tax strategist Tom Wheelwright says most people stay stuck because they ask 'Can I?' instead of 'How do I?'. He's talking about money and taxes, but the same swap unlocks almost any stuck spot in your life.
▶ Watch the full episode with Tom Wheelwright for deeper context on how to approach these questionsWhere You Got A No
Think of something at work, with money, or in your life where you asked an expert or yourself a question and the answer was basically 'no' or 'that's just how it is.' What was it, and what exact question did you ask?
The Small Question
Tom's example: people ask 'Is this deductible?' when they should ask 'How do I make it deductible?' Look at your question above. Were you really asking permission, and if so, what are you afraid the true answer is?
Ask Why Five Times
Take your last answer and ask 'why is that true?' Then ask why of that answer, and keep going five times. By the fifth why, what's the real reason underneath that you couldn't see at the top?
Change One Fact
Tom says you change the result by changing your facts, not by wishing the rule away. If the answer you want needs a different setup, what one fact about your situation would you have to change to make a yes possible?
Name The Who
Tom says luck is people plus action, and the wrong 'who' costs you for years. Who already gets the result you want here, and what's the first question you'd put to them, phrased as 'how,' not 'can I'?