It was a rainy day…

I could hear the soft rain and rumbling thunder as I listened to my sweet grandma over our land line. 

“What are you up to today Grandma?” 

“Well hon, I’m just sittin’ here working on my puzzle.” Said my grandma in her midwestern accent. 

As lightning illuminated the house, I sat on the stairs and admired how my grandma practices slow living. She works harder than anyone I know, but she also knows when to rest. 

I repositioned myself on the bottom step and was reminded of her entrepreneurial venture running “Happy Hours Preschool and Daycare.” 

“Grandma, can you tell me more about when you owned your daycare?”

“Well hon,” My grandma said with a smile in her voice, “I was working for Head Start as a bus driver. I was driving the kids all around before and after daycare, and I’d help out during the day…”

“…They eventually moved the daycare to another town, but I was still driving the bus. I was getting tired of driving the long distances on the school bus, so I just decided I’d start a daycare.”

“Just like that?” I asked.

“Ummhmm. I became state licensed, got a place, put an add in the paper, and opened up.” 

“Wow, really?” I asked. “Had you hoped of owning your own daycare someday?”

“No hon, I was just tired of driving the bus, and since Head Start had moved, Stockon was in need of a daycare.” 

“That’s ambitious Grandma.” 

“What are some of your favorite memories of the daycare?” I asked.

“Oh I have so many good memories,” She said with a smile in her voice. 

“I enjoyed letting them do art. We would do finger painting, but instead of using paint, I’d make chocolate pudding.”

“One time I tore off big sheets of paper and we had the children trace each other on the paper and paint their clothes on. We hung them all around the room and had the kids find each other.” 

“Another time I bought a little swimming pool to play in and as we were trying to fill it up, the kids started chasing me around with the hose!” She chuckled. “They thought this was so funny!” 

It was good to hear her reminisce and share the happy moments with me. 

“It sounds like you have many wonderful memories, Grandma. What did you enjoy most about your job?” 

… 

My Grandma was an entrepreneur in her fifties. She is now in her 80s and still doesn’t let age keep her from doing what her heart desires. She is resilient. She teaches with conviction and is a beautiful example of being faithful in everything. 

Previously, we discussed the importance of generational influence, the meaning of ORIGIN, and what it means to Live Your Legacy. Today, I am guiding you through practical ways to initiate enriching conversations with your family. 

Asking questions about family history can open the door for wonderful walks down memory lane, but they can also trigger hard discussions. The key is to not fear what you may be met with and to continue with respect.

First and foremost, it is so important to begin with love and acceptance; express genuine curiosity out of your love and acceptance. 

Begin questions with “Can you tell me about…” This phrase sounds less direct than questions that begin with  “What” or “Why” and will show the other person you are genuinely interested in their story and not just in receiving an answer. 

The “What” and “Why”  questions will follow, but if you are able to lead with “Can you tell me about..” I believe this will put the other person at ease and properly reflect your genuine character. 

 Some of these conversations may lead to a place of tension (this may be due to the subject matter or the willingness of the other person to open up about their life). 

Use your discretion in continuing to pursue conversation and always assure the other person of your love for them and your desire to learn more about who they are, so you are able to honor them in the best way you can — To make them feel seen and known and loved. 

I will leave you with 5 practical questions you may use to spark meaningful conversation with any of your family members. 

5 Questions To Ask Your Family

(Or Really Anyone You Are Curious About)

1. Can you tell me (more) about (when you were my age, when you met ___, the time that___)? 
2. What is your favorite (least favorite) childhood memory? 
3. Can you recall times in your life when you  felt very (loved, alone, confident, fearful) ? 
4. What is something you would have done differently (when I was growing up (if speaking to a parent), when you first moved out on your own, in your friendships throughout life)?
5. What is something you hope to leave in your legacy?

I’m sure you will come up with more questions as the conversation continues! These questions can be altered to fit your specific needs and essentially provide a starting point for initiating insightful and impactful conversations. 

I wish you the very best and would love to hear what you learn! Please don’t hesitate to share your stories with me, I am always interested. The upcoming posts will feature some incredible people and their legacy stories. 

Start Conversing, 

Caralee Rose