Questions To Consider 🧭

đź’Ľ Business + Property Strategy

  1. What role do you want The Printing Press to play in your life five years from now?
    • Is it a passion project, full-time business, community hub—or something else?
  2. Would owning 33 Sixth Street give you more creative or operational freedom?
    • Could you expand offerings (events, classes, local art retail)?
    • Would the added visibility change your customer base?
  3. Do you want to build an upstairs apartment immediately, or phase it in over time?
    • Could you live onsite?
    • Rent it out?
    • Use it for family down the line?
  4. Would consolidating work and home (even temporarily in an RV or later in the apartment) reduce friction in your day-to-day?
    • More time, less commuting, easier logistics?
  5. How do you feel about hosting community events onsite—poetry readings, maker workshops, First Friday art nights?
    • Is that the future of the Press—or a distraction?

đź’° Financial Considerations

  1. What would you net from selling 6 Apache—and where does that money work best for your future?
    • Could it fund the purchase and the apartment build?
    • Would you feel financially freer or more exposed?
  2. Are you open to taking on new debt (mortgage, construction loan, HELOC), or is debt reduction a bigger priority right now?
  3. If you rented 6 Apache to your kids, would you structure it like a true rental?
    • Lease, rent amount, responsibilities?
    • Or more of a transitional arrangement?
  4. Could that rental support your monthly costs at 33 Sixth—or would it be emotionally complicated to manage?
  5. If your business revenue increased because of higher visibility, what would you do with the surplus?
    • Pay down debt?
    • Reinvest in the space?
    • Save for retirement?

🧡 Personal / Lifestyle Reflection

  1. What kind of lifestyle are you craving in this next chapter?
    • Simplicity? Community? Independence? Creativity?
  2. What does “home” mean to you right now?
    • A permanent address?
    • A space that serves your work?
    • A place to help your kids launch?
  3. How do you envision supporting your older kids as they move toward independence?
    • Is housing part of that support?
    • Or would another structure (shared property, nearby rentals) work better?
  4. Would living in an RV temporarily feel adventurous, exhausting—or both?
    • Could it be a bridge to something more stable?
    • Or just one more stressor?
  5. How do you want your life to feel one year from now?
    • What does a successful day look like?
    • Where are you waking up?
    • What are you building toward?