Guest Blog Series, Part 1: Imagining and Reimagining

Dawn Sully Pile is an author, speaker and hybrid coach/consultant whose passion is people. Whether working with children or adults, her intention is to be a catalyst for imagining new perspectives and possibilities and to step into them with courage. 

Dawn is a Certified Professional Co-Active Coach and also holds a Master of Arts in Ministry. After 35 years in the education world she established her own business, Dawn Sully Pile, MA, CPCC, which is a wonderful potpourri.

For the sake of this writing, her most valued credential is that at 72 years old she is passionate about facilitating intergenerational conversations within families, whatever the family configuration, about end-of-life details and what matters most. To do so before it is too late is one of the greatest gifts to give and to receive. 

Her book is Baby Boomers +: A Guide to Designing These Years, Honoring the Full Circle of Life, and Creating Life-Giving Conversations. It is available through Amazon in paperback and on Kindle. You may be in touch with Dawn at

You may be in touch with Dawn at

Part 1: Imagining and Reimagining

My imagination is a part of me I have never spent time longing for or developing. If there were a wordle, a word cloud of all of my qualities, IMAGINATION would be big, bold and center. It has taken me into stunning ideas, scenes, sounds, places, and even into the indescribable.

At the same time, I am equally skilled at letting it take me into stories and assumptions that do not serve me, from the silliest notion I can quite easily dismiss to spiraling down a rabbit hole that likely contains little truth. The rabbit hole only surrounds me with fears, worry, and fabrications that deplete my energy.

A tool that comes in handy in those moments is reimagination – taking that which ushers me into the gloomy, pessimistic space and shifting it, realigning it with my values, or bringing it into the light. I get to reframe.

I am always in choice as to how I allow my imagination to take up residence, as are we all.

Why does this matter?

It deeply matters when discerning how to engage in what I call life-giving conversations with family members or those closest to us. Family can be many configurations. 

It makes all the difference when we are called to be in communication with one another about important life and end of life details.

Come with me into two rooms.

In the first, I, a woman in her early 70s, am sitting in a circle with age peers having a conversation about the third-third of life.

Specifically we have gathered to talk about how to communicate with our children or those closest to us about how we choose to live life now. More importantly, it is about how to share important information that allows us to exit this life knowing all is in order.

The circle contains many emotions and imaginings.

In the room right next door, I, a woman in my early 70s, and because I treasure my imagination, I can be in both rooms simultaneously, am sitting in a circle of those in what I call the second third of life – 30-60.

Here, too, the conversation is about current choices, how to manage busy lives and how to engage parents to learn their choices for end of life matters. The desire is to not be surprised with messy estate resolution, knowing it will be enough to adapt to the void created by their physical absence.  Those gathered are wondering how they can be initiators, if necessary.

This circle, too, is filled with many emotions and imaginings.

Little does either group know how the conversations mirror each other. If only the wall could talk.

I do want to acknowledge there are families for whom these conversations are natural and flow seamlessly. That is a gift.

For most, the discussion about end of life, in particular, offers a challenge to be courageous and to create the time and space for it.

Here are a few examples of imagining that came up in both groups and how to reimagine each conversation:

  • Imagine: I only want to talk about life, not death. It’s too soon to have that conversation.
  • Reimagine: Death is part of life. There is birth and there is death. We celebrate the word birth and find it harder to bless the word death. We can, if we’d like, talk about life as a continuum or life as a full circle. That feels softer and we will still keep it real.
  • Imagine: If I bring this up with my children…If I bring this up with my parents…they will instantly shut down the conversation and maybe even walk out of the room.
  • Reimagine: It would be so easy for me to refuse this conversation, so easy. I know, though, that having it will allow me to live without regret and that we can erase the fears. It will be done! Check! The time for us is now.
  • Imagine: I can imagine how __________ will respond and that will be different than how ___________ responds and it is just going to create a big mess. ________always gets mad and ______________starts to cry when we try to talk about anything with difficult layers. There is only one calm person among us. I just don’t think I can deal with it.
  • Reimagine: We can set an intention together to honor each person for who they are, to feel what they feel and allow time for processing. When we gather again it will be with more ease.
  • Imagine: I’m afraid if I talk to my child about my death and my choices…. I am afraid if I talk with my parents about death and their choices…that it might feel like it is going to happen soon, as if I might make it real just by talking about it.
  • Reimagine: It is natural for me to think at times that I am going to call something to me that I do not want. How many times has that actually happened? Rarely! But I am very good at believing it will!

The list goes on. Each of us has our own imaginings and stories, perhaps attached to generations that have gone before.

We have a beautiful opportunity to participate in creating ways of coming together for the good of all, to model a new conversation paradigm for future generations. This past year has imprinted more than ever the importance of this work.

I believe with my whole heart that we have the capacity to do this and do it well…with generosity of spirit, grace and love.  

In Part 2 we will leave the rooms and go on a journey together to a well. I look forward to walking along the path with you.  Imaginary dress is casual.