Going to bed with questions

night skyReading for a while before I hit the hay usually leads to a few questions rattling around my mind. Questions keep me up at night. Well, good questions do. Not necessarily existential questions of meaning, though those can make for some interesting thoughts and discussion. Rather, questions of possibility, questions of why and thoughts of solutions rattle around in my mind through the night. I’ve found that over days and weeks some questions keep showing up in my evenings and resurfacing in the morning. I take that as a cue to spend time with them.

Reading Warren Berger’s A More Beautiful Question I was challenged to work through my questions from why, to what if and ending with how. Berger says, “We’re all hungry for the answers. But first we have to ask the right questions.” Here are a just a few of my questions:

  • Why was I so at ease with accessing debt and running up large student loan balances as a teenager?
    • What if high schoolers understood the long term impact of their choice of college and financing?
      • How do I create a platform to educate parents and prospective college students of the incredible and limiting impact of college debt on their future?
  • Why does the commission on a real estate transaction cost upwards of 6% of a home’s purchase price, at times the bulk of a seller’s equity?
    • What if buyers and sellers were in a position of strength in the real estate transaction and commission negotiations?
      • How can I establish a real estate brokerage that truly puts customers/clients in the driver’s seat, treating them as investors/partners, negotiating commission based on customer needs, market conditions and value? Or how could I do it for free?
  • Why, at times, have I felt stuck in my career and fearful of making healthy changes?
    • What if I, and others, could transition into engaging work with a great support system?
      • How could I create an environment where people could step into entrepreneurship in a highly supportive environment, providing coaching, financing consultation/connections and administrative support?
  • Why are so many people I know up to their eyeballs in debt (student loans, house, cars, credit cards) and normalizing it?
    • What if people wake up to the freedoms they’ve lost by accumulating debt, worked their way out of it and began to live out their dreams unrestrained?
      • How can I bring people together in/on an educational/motivational platform to help facilitate understanding of the value of a debt free life, delayed gratification and the freedom to pursue their dreams?
  • Why are churches better known for their answers than their ability to ask questions?
    • What if there was an environment where people of or interested in faith could connect with their questions rather than their answers?
      • How can I create/facilitate an environment where people are free to explore questions (even if they seem heretical), discover possibilities and learn together in a curious community of faith in Christ?

So, tonight, take a question or two to bed with you. If you wake up and they’ve faded then just start again. But, if they’re still there in the morning you may find yourself on to something important to you. Lean into them. Ask yourself the why, what if and how of your question.


Oh, and read Warren Berger’s A More Beautiful Question. It’ll help you come up with and craft your questions.

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