Why Most People Never Tell Their Story (And Regret It Later) | Michele DeFilippo

What happens when someone finally sits down and documents their life story?

In this episode of the Give A Heck Podcast, Dwight Heck sits down with Michele DeFilippo, a publishing expert with over five decades of experience, to explore why so many people never tell their story, how writing transforms the author, and why capturing your experiences is one of the most important legacies you can leave behind.

Give A Heck Podcast — Real conversations about purpose, personal growth, financial stewardship, mindset, faith, and living life intentionally.

Before diving into the mechanics of writing and publishing, there is a deeper question worth asking.

Why do so many people never start in the first place?


🚫 Why Most People Never Tell Their Story

Most people believe they need the perfect time, the perfect skill set, or the perfect message before they begin writing.

The reality is far simpler.

Stories are not lost because people lack ability. They are lost because people wait too long.

And when they wait too long, those stories are gone forever.

That hesitation often comes from misunderstanding what writing is actually about.


✍️ The Real Value of Writing Isn’t What You Think

It’s Not About Being a Great Writer

Many people hold back because they believe their writing needs to be polished or professional.

What matters most is not perfect prose, but the authenticity and perspective behind the story.

Every Story Is Unique

Even when multiple books exist on the same topic, no two authors bring the same life experience, insight, or voice.

That is what makes each story valuable.

Once you understand that, the focus shifts away from perfection and toward process.


🏗️ From Craft to Convenience: What Changed in Publishing

The Process Used to Be a Craft

Publishing once required detailed manual work, from physical paste-up layouts to precise design techniques.

Speed Has Replaced Connection

Technology has made publishing faster and more efficient, but often at the cost of craftsmanship, care, and personal connection to the final product.

And that shift has also impacted how authors experience the journey itself.


🧠 Why Writing Changes the Person Doing It

Reflection Creates Clarity

When people begin writing their thoughts and experiences, they often discover insights about their life they had never fully processed.

The Cathartic Effect of Storytelling

Writing becomes more than documentation. It becomes a tool for emotional processing, clarity, and personal growth.

Which makes the decision not to write even more significant.


⚠️ The Cost of Not Documenting Your Story

Lost Family History

Undocumented stories disappear, leaving gaps in understanding for future generations.

Regret Comes Later

Many people only realize the importance of their story when it is too late to capture it.

That is where the real regret begins.

This is why how we approach writing matters just as much as whether we start.


📚 Books Are Not Commodities, They Are Legacy

The Problem With “Fast Books”

Rushing to produce a book quickly often sacrifices quality, meaning, and long-term value.

A Book Should Be a Work of Art

A finished book represents the author’s effort, perspective, and lived experience. It should reflect care, not convenience.


🔗 Continue the Conversation

If this episode made you reflect on your story, your purpose, and the direction of your life, these conversations will take you deeper.

🎯 Are You Drifting Through Life? The Silent Thief of Direction and Purpose
Most people do not realize they are drifting until years have already passed. This episode breaks down how life drift quietly steals direction from your finances, career, relationships, health, and purpose, and how to start living more intentionally.

💡 How Journaling Improves Mental Health and Emotional Awareness
If writing feels overwhelming, this conversation shows how journaling can help build self-awareness, emotional clarity, and intentional living without needing perfection.

🔥 Alcohol-Free Leadership: How Quitting Drinking Unlocks Clarity and High Performance with Toni Will
This episode explores clarity, intentional living, accountability, and what happens when someone chooses alignment over performance without purpose.

⚠️ Trust But Verify: How Blind Trust Cost Me Tens of Thousands in Business
A hard lesson on assumptions, referrals, business decisions, and why clarity and due diligence matter in every area of life.

💰 I Was Teaching Financial Freedom While Living Financially Broken
A raw and honest reflection on financial misalignment, responsibility, and the wake-up call that forced a return to intentional living.

If you want, I’ll now rebuild the entire post one last time with these fixed links and your corrected connect section, all in one clean paste-ready block.


👤 About Michele DeFilippo

Michele DeFilippo is a publishing industry veteran with more than five decades of experience helping authors bring their stories to life.

Through her work, she has guided countless individuals in transforming their ideas, experiences, and life lessons into meaningful books that serve as both personal expression and lasting legacy.

Her approach emphasizes the importance of human connection, craftsmanship, and treating every book as a unique work of art rather than a commodity.


🤝 Connect with Michele DeFilippo & Dwight Heck

👩‍💼 Michele DeFilippo – Click a word to be directed to the website

🌐 1106 Design
📘 Free Self-Publishing Guide
📩 md@1106design.com
🔗 LinkedIn
📘 Facebook
🐦 X
▶️ YouTube

🎙️ Dwight Heck – Click a word to be directed to the website

🌐 Give A Heck
🎧 Podcast
🔗 LinkedIn
📸 Instagram
🧵 Threads
🎵 TikTok
📘 Facebook
▶️ YouTube
🐦 X


💭 Final Thoughts: Your Story Matters More Than You Think

Your story does not need to be perfect.

It needs to be told.

Because the greatest loss is not writing something imperfect.

It is never writing it at all.

And leaving your experiences, lessons, and perspective behind without a voice for those who come after you.


🎙️ Listen, Follow, and Share

If this episode resonated with you, please take a moment to share it with someone who needs to hear this message.

Follow the Give A Heck Podcast on your favourite platform, leave a review, and help more people start living life on purpose, not by accident.


🚀 Want to Live Life on Purpose?

If you are feeling stuck, drifting, or lacking clarity in your life, finances, or direction, it starts with intentional conversations.

Reach out, start the conversation, and begin building a life that aligns with what truly matters to you.

📝 Unedited Transcript

What happens when someone finally sits down and writes their thoughts, experiences, and life lessons on paper?

Often it starts as a simple idea, but once people begin writing, something interesting tends to happen.

They slow down, reflect, and sometimes discover parts of their own story that were never fully clear before.

But for some people, writing becomes creative expression. For others, it becomes a way to process their life, preserve their experiences, or share knowledge that might otherwise be lost.

Welcome back to the Give A Heck podcast. I’m your host, Dwight Heck, here to help you live life on purpose and not by accident.

Today’s guest, Michelle DiFilippo, has spent more than five decades working closely with authors and books, guiding people through the process of turning their ideas and life experiences into something that can be shared with the world.

Through that work, she has had a front row seat to something fascinating—the way writing often changes the person doing it.

When people begin putting their thoughts, memories and lessons into words, they often gain clarity about their own journey and the impact they want their story to have.

Today, we’re going to explore the deeper side of writing.

Why documenting our thoughts matters, how writing can become reflective and even cathartic, and why capturing our experiences can play an important role in the legacy we leave behind.

Michelle, welcome to the Give A Heck podcast. Thanks so much for agreeing to come on and share with us some of your life journey.


[00:01:52 – 00:01:54]
Thank you for having me, Dwight. I appreciate it.


[00:01:55 – 00:02:58]
Yes, I look forward to our conversation.

For those watching or listening, you’ve heard this before. We had a great session prior to hitting record. Michelle is so easy to talk to and have a conversation.

This podcast is going to be great because you’re going to be able to really understand and relate to Michelle’s origin, her life experiences, because of course, I’ve researched.

Obviously not to the extent of what we’re going to learn now, but hold on. Buckle up. Here we go.

One of the things I start the show off with and I focus on Michelle, is a person’s origin story.

I like starting at the beginning. Whatever you’re willing to share your earliest recollections of your life. Good, bad, or indifferent.

Our past is indicative of our future, more so than people want to acknowledge.

So please do me a favor, share your origin story and be as vulnerable as you’d like.


[00:02:58 – 00:03:15]
Well, first I need to tell you that I majored in Magic Markers in school, so I’m not necessarily a deep thinker.

But I grew up in Brooklyn, New York, and my first job was with Crown Publishing in New York.

And that’s how I got into the publishing business.


[00:03:17 – 00:03:26]
So you got into the publishing business. You were born in New York.

What was your childhood like, though?

Tell me something about your origin of being younger.


[00:03:27 – 00:04:04]
Oh, grew up in an Italian American family.

My grandparents, three of my four grandparents were from Italy. So we were well steeped in the Italian culture every minute of every day.

And that, I guess that was a pretty big definition of who I wound up to be because it was an interesting culture, I think, and imparted some really important and worthwhile values growing up.

So that when I finally was old enough to emerge into the adult world, I was pretty well prepared for it, I think.


[00:04:05 – 00:04:33]
So the knowledge from their ancestry affected obviously how you grew up, because things come over from one society to another.

Did you find any of it conflicting to what you had growing up as a child, in school, or even as a young adult where you had a thought process that was influenced by your ancestry?


[00:04:34 – 00:04:40]
Oh, I don’t know how to answer that.


[00:04:41 – 00:05:19]
I went to Catholic school, so that experience actually mirrored the values and upbringing that I had at home.

So there was no conflict there.

So maybe I would have to say I went out into the world in a very idealistic state of mind and never expected to meet people who weren’t honest or weren’t nice.

And so that was kind of a strange experience when those experiences first started to accumulate.


[00:05:20 – 00:06:05]
Yeah, I can relate to that.

Practicing Catholic still today. Grew up Catholic school, grew up in a small farming community.

All of a sudden went from a community of like 12,000 people to a community that I live now that’s 1.5 million.

And you find out the harsh realities of life that not everybody is as confined to what we were taught or what we experienced through learned behaviors.

Did any of these things that happened to you as a child, did you ever think that you would get into publishing?

Was that ever anything that was really attractive to you?


[00:06:06 – 00:06:44]
No, it was.

My whole upbringing was blue collar.

My dad worked in manholes. My mom was a stay at home mom.

And so the whole entire focus was getting a job.

So I went to community college, went out looking for work, and the first company that offered me a job, I said yes.

And it turned out to be in the publishing industry.

[00:06:46 – 00:07:46]
Which is, you know, that’s the way life is.

We sometimes fall into things we don’t realize that’s where we’re going to be.

Even in my career that I’m in today, I didn’t realize I’d ever be in the financial world.

So when you were—you mentioned too, at one point in time prior to pre recording, which I thought the story was really good—that your parents didn’t necessarily, they followed everybody else’s advice.

You had a counselor and you ended up going to a specific school to become a secretary when really you were an honor student and could have gone anywhere.

Do you see that today as being something that was a major catalyst to your success, or was it something that you wish you could tell people today?

Listen, don’t pigeonhole. What would be your thoughts on that?


[00:07:46 – 00:08:39]
Oh, definitely.

Don’t pigeonhole. Don’t let anyone pigeonhole you. And don’t pigeonhole yourself.

Because my particular experience, my eighth grade counselor told my parents I was not college material.

Which I don’t know how she could have even said that because I was getting straight A’s, but she did.

There was, back then, believe it or not, in New York, Irish and Italians hated each other.

And most of the nuns who taught us in school were Irish and I was Italian.

So I think that might have had something to do with it.

But my parents believed her because she was religious.


[00:08:39 – 00:09:37]
So I was kind of shuffled off to a secretarial high school.

And it was also gender roles then too.

Women became secretaries. Women didn’t become doctors or lawyers or professionals.

A woman’s job was always to be an assistant.

So I was shuffled off into that.

The one good thing about it is I learned how to type really fast.

But it did limit what I could do.

Because as I got older and thought maybe I’d like to go to college, I didn’t have the credits to get in.


[00:09:43 – 00:11:21]
But the nice thing is you’re able to share that experience.

There could be people listening or watching that are going, hey, that’s me.

That happened to me too.

At the end of the day, we need to understand that just because of learned behavior doesn’t have to be the reality of the next generations.


[00:11:21 – 00:12:34]
So we enter the publishing world.

You spent more than 50 years in publishing.

Can you walk us through how it’s evolved?


[00:12:34 – 00:13:47]
Oh my gosh.

When I look back on how we used to do things compared to the way we do it now, it’s almost unbelievable.

When I first started, we used to do what they called paste up.

We would order long strips of typesetting and physically paste them into pages.

If there were errors, you’d literally cut and paste letters.


[00:13:48 – 00:14:51]
Do you think there was more connection back then?


[00:14:12 – 00:15:03]
Yes.

Preparing a book was considered a craft.

You had to draw boxes by hand with pens.

You had to learn how to make corners perfectly square.

There was pride in the work.


[00:15:04 – 00:16:14]
And today it’s just click and create.

The appreciation for the effort has changed.


[00:16:23 – 00:17:33]
But it’s more efficient.

Back then it could take months to produce a book.

Now it’s significantly faster.


[00:17:33 – 00:18:05]
What have those experiences taught you about authors?


[00:18:06 – 00:19:04]
Authors put their heart and soul into their work.

They care deeply about every word.

But in many cases today, they’re being misled and not getting the quality they deserve.


[00:19:04 – 00:20:36]
There’s more efficiency now, but sometimes we’ve lost standards.

The final product should still be a work of art.


[00:20:36 – 00:21:40]
Do you worry about AI in writing?


[00:21:41 – 00:22:25]
Yes.

We believe in human editors.

AI cannot replace human nuance and emotion.


[00:22:26 – 00:23:24]
People are using books as business cards now.

Not as legacy.


[00:23:26 – 00:24:23]
A book should not be treated as a commodity.

Every author brings a unique perspective.


[00:24:23 – 00:25:20]
AI lacks emotional intelligence.

That human connection matters.

[00:25:21 – 00:26:54]
And it will never put together words like Stephen King or any other of your favorite authors.

To have that creative imagination is something we have to think about when we’re dealing with people in life now.

Technology is growing faster than we can imagine.

The human brain has always been considered the most powerful computer in the world.

But is that still true?

That’s a question we’re going to be asking for years.


[00:26:55 – 00:27:30]
When people write books, I know when you finally wrote your own book…

Did you understand the cathartic nature of writing?


[00:27:30 – 00:28:15]
My book was a compilation of blog posts.

My editor turned it into something I never would have imagined.

I was very thankful for her skills.

It takes a lot of experts to put out a good book.


[00:28:16 – 00:30:30]
Do you think writing enhances people’s lives?

I think it does.

There was a quote—nobody should die with a book inside them.

If you feel inclined to write, you should.

Don’t let it sit.

Let it rip.


[00:30:31 – 00:31:08]
There’s a saying in publishing…

You don’t finish a book—you declare an ending.


[00:31:09 – 00:32:26]
That’s powerful.

For me, it wasn’t about writing a book.

It was about not letting the music die inside me.


[00:32:27 – 00:33:02]
My own mother never documented her life.

And now that she’s gone, there’s nothing left.

Just a few trinkets.

I wish I had her story.


[00:33:02 – 00:34:02]
Stories disappear if they’re not documented.

That affects future generations.


[00:34:03 – 00:35:05]
We all have something to share.

It’s about legacy, not sales.


[00:35:06 – 00:36:13]
People don’t value history like they used to.

We’re losing connection.


[00:36:13 – 00:37:30]
Books can shape us.

What’s one book that impacted you?


[00:37:31 – 00:38:33]
The Agony and the Ecstasy.

It stayed with me.

I read it again later in life and got even more from it.


[00:38:34 – 00:39:54]
When you’re older, you connect differently.

You understand struggle and meaning more deeply.


[00:39:54 – 00:40:40]
Tell me about your business.


[00:40:40 – 00:41:33]
We start with a conversation.

We don’t pressure people.

Every author is different.

We treat them that way.


[00:41:34 – 00:42:17]
That’s rare today.

People want real connection.


[00:42:17 – 00:43:02]
Publishing has become a commodity.

We don’t treat it that way.


[00:43:02 – 00:44:32]
Do you still feel joy after 50 years?

Yes.

Because doing meaningful work matters.


[00:44:32 – 00:45:46]
That human connection is everything.


[00:45:48 – 00:47:16]
How can people reach you?

1106design.com

You can download my book for free.


[00:47:17 – 00:48:36]
There’s a difference between publishers and author services.

Authors can retain more revenue with the right structure.


[00:48:37 – 00:49:29]
That’s an important distinction people don’t understand.


[00:49:30 – 00:50:18]
Why 1106?

It’s my birthday.


[00:50:21 – 00:51:00]
People believe all kinds of things.

Everyone has their own lens.


[00:51:00 – 00:52:08]
Relationships matter.

Connection matters.


[00:52:09 – 00:52:56]
This has been a great conversation.


[00:52:57 – 00:52:59]
It’s the only life you’ve got.


[00:53:01 – 00:53:17]
If you don’t care about your life, there’s no point.


[00:53:18 – 00:54:59]
Life is not a dress rehearsal.

It’s happening now.

Feed your brain.

Grow every day.


[00:55:00 – 00:56:07]
Thank you for being here.

If this resonated, please share.

Subscribe and leave a review.


[00:56:08 – 00:57:04]
Until next time…

Live life on purpose and not by accident.

And remember—it’s never too late to give a heck.