Self Employed, Solopreneur, Freelancer Work Retreat Questions

Here are all the questions that I used for my work retreat Dec 2016. These are in order in which I worked through them, it took approximately two days.

Day 1

Warm Up Questions

  • What do you want to get out of this experience?
  • How do you want to enter into this reflection work?


  • What and to whom are you really grateful for this past year?
  • What actions do you want to take on that gratitude?

Taking Stock

  • In the past year, what did you do?
  • How do you want to celebrate your accomplishments this past year?
  • What has your relationship with work been this past 12 months?
  • What questions are driving your relationship and perspective on work?

Self Assessment

  • What went well this year?
  • What didn’t go well?
  • What are you spending your time on?
  • What work do you love/find most rewarding?
  • What do you wish you had done this last year?

Lessons Learned

  • What are the lessons that jump to mind from this year?
  • What are your big takeaways from this?

Day 2


  • What kind of world do you want to help create?
  • How do you want to relate to your work?
  • What questions do you want to center your work relationship around? What are the key questions you want guiding you?
  • What permission do you need for this next year? (from yourself, others, the world)
  • What didn’t happen this year that you wanted to happen?
  • What stopped it from happening?
  • Do you forgive yourself?
  • What would you need to do to get a clean slate?


  • How much do you want to work this year? What does that look like?
  • What does an ideal work week look like?
  • What are your big goals for this year?
  • What would make this year a success? What would make this year a great success?

Q1 Planning

  • What do you want to do during Q1?

Cool Down

  • What did you learn from this retreat?
  • What plans would you like to make for your next retreat?
  • What questions do you want to be sure to answer at the next retreat?

Want to read more about my biggest lessons and takeaways from this work retreat? Read more here.