Conversation Challenge Connecting Through Purposeful Dialogue Practice
Updated: 5 days ago
Are you up for our Conversation Challenge?
Let me back up a few steps. If you have been following along, I have been on a journey for over a year now in helping people create more sensory based experiences through intentional living. Today, with more than 50 posts, Rooted & Refined Living has a growing community who share those same interests. As the community has grown, I have also expanded the site with additional authors, Amy Reinert, and my dad, Tony Fiore. I met Amy initially through LinkedIn reading about her posts about the Boston area. We met up in person last year and she has been writing on our website for a few months now. My dad has also been writing and having a great time sharing his years of storytelling to a new audience. And while I have heard many of the stories my dad has shared in his posts, I usually learn something new with each one.
The combination of having Amy and my dad write has sparked many conversations, either between us, about them, or from others. My favorite time is when others, who I don't know, carry the conversation on long after the post has been written and published. This comes in new forms including reading the conversations that happen on a social media forward or a conversation within my own home. One of my favorites is when my dad wrote about his two best friends of 60+ years. While the three of them talk weekly, as my dad started writing the post, they started talking more frequently, learning new things, and bringing back memories that were long forgotten.
This is the power of conversation.
Another story that came about recently is from a networking call I joined a few months ago. As a follow on to that call, I was connected with 5 individuals where I had new conversations. One of those conversations led me to pose a question about an idea I had around a behavioral change coaching business. After one day, the person asked me if I had started the business yet and then asked me again 3 days later. I thought about it for a moment and asked if she wanted to be my first client where I would test out the program on her. With great success, she saw real benefits out of the program, and I launched Rooted in Curiosity, which is designed for executives, business owners, and high performers seeking to eliminate daily exhaustion and reclaim sustainable clarity. It became a passion of mine and it all started through an initial conversation.
Rooted In Curiosity is based on the idea that to improve in anything, curiosity needs to take a front seat. For me, my curiosity led me to learn about a wide range of topics, everything from feeling better to improving my mindset to having better conversations. For the last one, I started following Vanessa Van Edwards, who helps people communicate with confidence. Vanessa speaks frequently on podcasts, participates as a keynote speaker, and is an author.
The author topic is the basis for this post and the following section. She reached out to her audience asking if anyone had a podcast that wanted to engage in this discussion to reach out. While I don't have a podcast, I do have an audience through a few different channels and thought I could make it work with a blog post. She (or her team) thought so too. I was selected among the podcast group to participate in this initiative.
Purposeful Conversation Challenge
A single good conversation can change someone. You already know that, it's what you do every time you pick up the phone (or in my case, write a blog post).
Vanessa has a new book coming out on Oct 9, 2026, called Conversation: How to Connect with Anyone and Make Every Interaction Count. It is built around one belief: the most meaningful moments in our lives don't happen by accident. They happen in what she calls purposeful conversations. And her mission is to spark more of them, all over the world.
Her purposeful conversation challenge was to have me answer 3-5 questions and have another person answer the questions as well. So of course, I reached out to Amy and my dad to help answer these questions. We will be picking different questions so it will be fun to see what answers come back when I get them and publish the answers below.
I am sharing all of the questions Vanessa's team asked us to start with in the hopes that these will spark new conversations with your family, friends, colleagues, or even strangers.
So here we go. Amy, Tony (my dad), and me answering 3-5 questions each.
Amy's Q&A
Would you ever write a book? What about?
I’ve been thinking about writing a book for years.
The book itself keeps changing.
For a while, it was going to be about motherhood. Then midlife. I even had a title for that one: Unapologetic, which I know is not exactly breaking new ground in the title department.
Then there was A Rude Awakening, a book about clarity. I liked that one quite a bit. It came fast and hard and furious, as some ideas do. And then it went away.
Right now, the book is called Life In the Box.
The Box is a real place. I live in a little town in Massachusetts called Boxborough, which we shorten to “the Box.” And I do, quite literally, live in it.
It’s a pretty nice box, too. Idyllic. Suburban. Safe. Beautiful. The kind of place where you can very easily look around and think, "Well, this worked out."
But I’ve been thinking about boxes in a different way for some time. Because I think we all live in one.
Not necessarily the Matrix. I’m not getting into string theory or arguing that we’re living in a simulation. I mean the boxes we build, inherit, accept, or don’t even realize are there.
Maybe it’s conditioning or fear or just some primal, evolutionary wiring that has kept human beings alive for a very long time and isn’t particularly interested in whether we’re fulfilled.
I don’t know exactly what Life in the Box is about yet.
I know what I don’t want it to be. I don’t want to write a self-indulgent book about me and my life. We all have lives. Mine isn’t boring, but there was no cataclysmic event to center the story.
Nothing happened to me that would be the thing.
In fact, maybe the book could be called Nothing Happened.
Because nothing did.
And yet, here I am at 53, increasingly curious about how much of a life we actually choose. How much of what we want is something we decided to want. How much of what we fear deserves to scare us. How much of what we think we know is actually ours.
Maybe that’s the book. One about ordinary life.
What would you do if you weren’t afraid?
Write the damn book. 😀
Which is probably why, when I was given a long list of questions to choose from, I picked the one about writing a book first.
So what am I afraid of?
That I don’t really have anything to say. That people would find it boring. That I’d spend a lot of time and money on it and it would flop. That I’d have to beg people to buy it. That someone would take issue with something I wrote. That people would tell me it was good when it wasn’t. That I’d look foolish.
Basically, I’m afraid it wouldn’t be good.
Because right now, the book in my head is very good.
It can have a great launch. I can be invited on podcasts to talk about it. Maybe there are speaking events. Someone asks what I do and I get to say, “I’m an author.”
It’s a lovely little fantasy.
And as long as I don’t actually write the book, I never have to find out if any of it is true.
The imaginary book can always be good. The real one has to be written, and then somebody gets to read it. And judge it. And judge me.
So what would I do if I weren’t afraid?
Write the damn book.
What have you always wanted to learn?
Knife skills.
I cook a lot, and have for years. Not because I particularly love cooking. It’s just one of those jobs I inherited over time because I was the one closest to home most often. And as a mother, I also somehow became a personal chef, making different meals for different kids and getting very good at cooking to please a lot of different palates.
But after all these years of cooking, and owning some pretty good knives, I never actually learned how to use them properly.
I watch a lot of cooking shows, and I’m always a little envious when I see an actual chef like Antonia Lofaso pick up an onion and chop the whole thing perfectly in about nine seconds. Fingers intact.
If you come to my house, you’re getting a "rustic" chop.
And by rustic, I mean I have no knife skills.
What is your biggest goal right now?
Learning to just be.
Without having to be someone. Or something. Or always have something I’m working on, building, accomplishing, fixing, improving.
That’s harder than it sounds, for me, at least. We put a lot of value on doing, and probably even more on becoming. There’s always supposed to be something next.
I have things I want to do. I have work I care about. I may even write that book.
I just don’t want to need any of it to prove anything.
So that’s the goal.
To be. And be fine with that.
Tony's Q&A
Working on anything exciting these days?
Interesting question because the most exciting thing I have been doing is writing stories in my son Steven’s website- Rooted and Refined Living. Steve gave me Carte Blanche to write whatever I want… sort of like what Andy Rooney did on 60 Minutes.
Most of what I have written to date have been stories about my life… My career, my friends- real and imaginary( as depicted in stories I told my grandchildren) and my family.
I found that I want to leave my grandchildren with the lesson that there are Ups and Downs in Life and how you handle each is how you will succeed or fail and how you will be remembered.
In writing about my career which was built upon reaching hard to reach college students in the 80s and 90s with Brand Advertising on Campus. That was the justification to get companies such as P&G, Honda, and American Express to pay our company millions to build brand awareness and trial. Today, our company, MarketSource, could not exist because these companies could reach millions of college students through the Internet on an iPhone. I realize how lucky I
was to be in the right place at the right time.
Writing about my younger brother Ray brought back memories of how great he was as a billiards player. We had a 4.5 year age difference and we certainly took different career paths but we were always close.
And writing about my grade school friend “‘Little Johnny “ brought back the days of being bullied by Bully George who charged a Daily Protection Fee ( to protect us from him). Bully George was a true entrepreneur. Amazing how funny it is now and how scary it was back then.
What would you do if you weren’t afraid?
I would hike up to the top of a large hill where I live and enjoy the endless view.
What makes me afraid to do so is a fear of heights that developed when I was a 10 year old boy playing stickball in our elementary school playground.
I was the batter and I hit a foul ball on the roof of the 4 story school building. Our stickball rule was that if you hit it on the roof you were responsible to retrieve it. After all a 25 cent runner Spalding ball was a big deal to have back then.
So I ran up the stairs onto the roof and I encountered a group of 14-15 year old boys who were smoking cigarettes and holding onto my ball. When I asked for it back and they laughed and said scram. I asked again and one kid said I think we should throw this little pest off the roof.
Realizing they were crazy enough to do so I ran to escape but was caught and lifted over the 4 foot roof wall. I was being held over the wall screaming for my life starting down below at a 50 foot drop onto concrete. My screaming drew the attention of the teacher in charge of the afterschool playground. He yelled at the bullies and they put me down and ran away. I ran down the school stairs to safety and ran home.
After that I was afraid to climb stairs and looking down below made me shake and sweat. I never sought professional help because I didn’t want to relived the experience. I probably should have but to this day many decades later I still have the problem and have still not hiked up the hill.
What book, movie or tv character are you most like and why?
Don Draper played by the actor Jon Hamm in the long running TV Show Mad Men.
Don Draper was an executive at an advertising in the 1960s. Advertising campaigns require strategy, creativity and repetition to achieve consumer awareness to buy the product. In the 1960s the top executives in large Ad Agencies had enormous power to influence Brand Decisions. Don Draper used that power to produce great creative advertising.
I was Marketing Manager for an antacid brand called Bromo Seltzer.
The Antacid Market is a large one as people overeat or eat spicy foods and need an antacid to soothe their stomach. Alka Seltzer was the market leader and was three times the size of Bromo Seltzer in terms of Antacid Market Share.
Bromo Seltzer came in a bottle and was granular. Alka Seltzer came in a bottle in tablet form.
Both products had the same ingredients yet Alka Seltzer was far more popular.
The challenge to me and our ad agency was to make commercials that would motivate antacid consumers to switch from Alka to Bromo.
We did have one point of difference. Each product had to dropped in water, stirred and then drank. Because Bromo was granulated it dissolved rapidly in water while Alka took a minute to dissolve. We built on that point of difference to insinuate that Bromo would bring relief in your stomach while Alka was still dissolving. We hired a young up and coming actor named Martin Sheen to demonstrate the difference. I met Martin at Kennedy Airport and took him to Barney’s to get two dark suits. The next day he flawlessly executed the commercial.
The commercial was a big success and grew Bromo 15%. I was Don Draper and got promoted to manage Schick razor blades, a much bigger brand.
A few years later Alka came up with the Plop Plop Fizz Fizz ad campaign which encouraged users to use two tablets instead of one.
Mad Men ran for 8 years and Jon Hamm has gone on to become a big star.
I will always remember my time on Bromo Seltzer and the Ad campaign created.
Steve's Q&A
What would you do if you weren't afraid?
Since I was in high school, I always had the idea of starting my own business. The problem was I never had the big idea that would make it happen. And then life happened with marriage, kids, and a full-time job that took me through a full 30 years before I got laid off in a corporate structuring in June 2025.
Through the advice of my wife, Mary Beth, and a few other respected colleagues, they all told me to slow down and think through what I wanted to do next. We were fortunate our financial situation allowed for some downtime while I figured out what I wanted to do when I grew up.
During our planned vacation 2 weeks after the layoff, we visited a Cacao farm in Kauai where when we left, my son Michael made the comment that now is the opportunity to do something with my passion around craft foods. This is what started Rooted & Refined Living. I found a way to monetize the website, although not enough to cover expenses of the site itself. However, the entire process has given me the opportunity to write (which helps the creative itch) and problem solve (which there is always something going wrong with a website). Creating the website was so much fun, but not enough to make a living from. The next step in the process regarding starting a business came when I decided to publish on LinkedIn that Rooted & Refined Living was a new job. This sparked new conversations including one that led me to pick up a contract job for a few months. What I learned through this process was I needed to start an LLC, which includes a business license from the state, accounting software, tax implications, and a bunch of paperwork, etc.
Ten years prior, my father-in-law passed away and he had owned his own business. As we were winding down and selling the business I saw first hand all of the things needed to be done to run a business from an administrative standpoint, and that deterred me from ever wanting to run my own business. But here we are 10 years later, and I had to set up the LLC for the contract role so I had a lot of the hard work behind me. In addition, a few years ago, I gave a TEDx on how my curiosity led to improving my health and well-being, which ultimately led me to be more productive at work. This evolved into blog posts on LinkedIn, a Udemy course I created (that I made $20 on) and ultimately led me to create Rooted & Refined Living. Fast forward to today, the next evolution came from the combination of all of those items from above, plus the love of helping people, which is why I created Rooted in Curiosity. With the idea in hand, and now the LLC, which was my biggest blocker, I was ready to make it all happen. So here we go!
What have you always wanted to learn?
This one is a bit retrospective, but something I am still very proud of and thought it was worth sharing.
When I was a kid, I used to try to solve the impossible Rubik’s Cube, but like most people, once you made your first move, it was messed up forever.
The original versions had stickers that you could peel off, as well as even pull apart the corner sections and replace them in the correct order. That was as close as I could come being able to solve it and figured it would take forever to learn.
Thanks to the time I had on vacation 4 years ago, I replaced reading a book to learning how to solve the cube. With about 30 minutes a day for 6 days and a YouTube video tutorial, I can proudly say I can now solve the Rubik’s Cube on my own.
While I don’t have a bucket list, I think this one would get a Big Green Check Mark!
Fast forward to today, I haven't picked up the cube in about 3 years as it is sitting nicely on my shelf in my office with all 6 sides perfectly solved. I would need a bit of a refresher course to relearn the skills, but I assume it's like riding a bike, and I would pick it back up relatively soon.
What did you always want to learn?
Would you ever write a book? What about?
Maybe. Still haven't decided about writing a book. I guess if I strung together all of my blogs, I could have a book already. Or perhaps the book would be about the concepts I coach on, which is all about improving through a curious mindset. I have had a few people ask me if I would ever write a book. The answer is not yet but someday!
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Here are the questions Vanessa gave us as prompts. I would encourage you to answer these for yourself and then reach out to someone and ask them. And then you have something to talk about sparking a conversation.
Working on anything exciting these days?
What's your personal passion project?
What's your biggest goal right now?
What have you always wanted to learn?
What book, movie, or TV character are you most like, and why?
How do you feel most misunderstood?
What would you do if you weren't afraid?
What gets you up in the morning?
Would you ever write a book? What about?
If you could wave a magic wand to heal the world, what would you do?
When was the last time you cried?
What's one thing you wish you could do but haven't, because you're afraid it won't work out?
Add your own .. what's a question you've been wanting to ask or answer?
The magic is in the mix! Choose the ones that spark your curiosity.
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