Prompt #8 is very straight forward. Have a conversation with you 5 years ago and 5 years in the future.
The past me:
Congratulations, you've moved to a community that is very down to earth. Not every kid on the block is involved in 2 dozen activities. Most families are happy taking 1 vacation and not disappointed by taking only 2 vacations. The elementary school has a new principal and she's great. Most of the folks in the NW burbs are asking, "So when are you moving back?" I answer, "Moving back where? I'm home."
It's time to face the facts about your career. You realize that employees are valued less and less each year. Despite predictions that the death rate should be rising with the death of the boomers, there are fewer jobs in funeral service. The day of the career employee is coming to an end. You don't want to own a funeral home. If you don't make a plan you're going to get run over and your family may be flattened along with you. You're smart enough. You're well liked and well respected. Figure this crap out, the sooner the better.
The future me:
What do you know, you have survived. Things didn't go quite the way you planned, but what does? The business you've started has grown each year. You are beginning to see a steady stream of referrals and groups are asking you to present at their meetings. Maybe there will be some sales for that book you've been writing for 5 years. The economy is finally creating some good paying jobs, but you are pushing 60. Who would have hired you? It's a good thing you decided to start that business. Sure, it took longer than it should have to get started but you did get started. Forget what you haven't accomplished and relish all that you have accomplished. All in all, it's gone pretty well.
That's my conversation with the past and future me. What would the chat you would have with your past and future self (5 years) sound like?