Debbie Weiss: On Second Thought, Maybe I Can

On episode #227 of The Author Factor Podcast I am having a conversation the author of the nonfiction book, On Second Thought, Maybe I Can, Debbie Weiss. Debbie is not only a seasoned entrepreneur but a new voice in the world of memoir writing, having transitioned from a diverse career in finance and insurance to becoming an author. Her journey reflects a rich tapestry of life experiences and personal evolution.

Debbie Weiss and Mike Capuzzi

Debbie’s book, On Second Thought, Maybe I Can, provides readers with a deeply personal narrative that is both empowering and relatable. It appeals to anyone who believes it might be too late to change their life’s direction. Her story beautifully illustrates that meaningful change is possible at any stage of life, making it a compelling read for anyone facing their own crossroads.

Debbie Weiss shares her Author Factor

Unlocking the Author Factor: This Episode's Big Takeaway

The key author factor from this episode is the transformative power of sharing personal stories through writing, as exemplified by Debbie Weiss. Debbie’s journey from feeling like a victim of her circumstances to using her experiences as a foundation for her memoir and subsequent works illustrates that writing can be as therapeutic for the author as it is inspiring for the readers. Her story encourages listeners to consider writing as a viable medium to overcome personal challenges and to impact others, demonstrating that it's never too late to change one’s life narrative and inspire others through storytelling.

Learn more about Debbie Weiss by visiting:


Mike Capuzzi: Welcome back to another insightful episode of the author Factor podcast. My guest today is Debbie Weiss, a multitalented entrepreneur, and an author with a flair for navigating life's challenges. Debbie's penned the best-selling memoir on second thought, maybe I can, which we're going to focus on today. Her remarkable journey of resilience and her mission to inspire others makes her a truly exceptional guest. Debbie, welcome to the show.


Debbie Weiss: Hi, Mike. Thank you so much for having me.


Mike Capuzzi: Well, first of all, congratulations. I know it's still less than a year since your first book, and then I just heard a little bird said that maybe you might be working on a second book, but I don't want to jump the gun too soon. Debbie, I just very briefly introduced you. Can you give our listeners a little bit more of a background of what you've done and what you're doing today?


Debbie Weiss: Sure. So, I have had many careers. None of them had to do with writing. Never thought that I'd be an author. I CPA, practicing CPA for ten years, and then I became an insurance agent and had my own insurance agency for the last almost 30 years. So a few years ago, I realized that based on my personal life circumstances, I had learned quite a bit, and I had a lot to share with others, and it seemed like writing a book was the best way to do that.


Mike Capuzzi: Very interesting. So let's go a little deeper, because before we focus on the book, it's interesting that you decided a book was a good medium to share your experiences. Again, the purpose of this podcast is to inspire others to do what you've done. And we haven't had too many memoir. I mean, is that how you would classify the book?


Debbie Weiss: Yes, definitely.


Mike Capuzzi: So we haven't had too many memoir authors. So let's, before we jump into the book, tell me a little bit more about, you know, the thought process behind this, because obviously, being in business for so many years and doing so much, you know, it's a big task. But why a book, Debbie?


Debbie Weiss: So, on a personal level, I have been a family caregiver for over 40 years since I was 17. I was my father's caregiver for 30 years. And then I have, my oldest son has some disabilities, and then my husband as well, became permanently disabled about five, six years ago now, and he passed away the end of December 2022. The majority of my life, I was a victim of my circumstances. I. That's how I viewed it, you know, that, um, this is it. My road seemed tougher than my friends and family, and. And I felt sorry for myself.


Debbie Weiss: I wasn't walking around like a Charlie Brown. I mean, I always, you know, tried to be positive, but yet, you know, just felt that I had no other options. Like my life was weighing me down and I had kind of an aha moment when I was turned 50 and realized, you know, how much life do I have left? And do I want to get to the end of that life and still feel the same way I do now with a lot of regrets of things that I never did. And I thought, no, and nobody's going to change it except for me. So I’ve been on, I’m 60 now, and I’ve been on that journey for ten years. And I felt like if I felt that way, there had to be others that felt the same. And the best way to do it was by sharing my story to hopefully inspire others to know that there’s choices out there.


Mike Capuzzi: So I would imagine that writing a memoir and well start focusing on your book, but I would gotta imagine it was a therapeutic process for you. I mean, I'm sure you wrote it just as much for yourself as for the potential listener out there or reader out there. Correct.


Debbie Weiss: You know, let me just touch on the fact that I did never expect to write a book and just kind of the signs were there. And I wound up with a coach who helped first time authors get their stories out there. So I had no idea what I was doing. I didn't believe that it was really going to be therapeutic. And when I actually made the decision to write the book, my husband was diagnosed with terminal cancer simultaneously. And so I was going to put it off. I mean, I'm going to jump in now on something. I have no idea what I'm doing.


Debbie Weiss: And I actually, the therapist that I was seeing at the time said, I don't think you should do that. I think you need to have this for yourself, to focus on something separate from what's going on with your husband and your family. And. And she was absolutely right. And it was therapeutic. It really did put me back into different times of my life, you know, a lot that were very difficult as well, you know, as what I was going through. But, um, it still was time just for me and that learning something new and finding that maybe I am creative, maybe I can write things that I had told myself my whole entire life that I couldn't do.


Mike Capuzzi: So let's now focus on the book. On second thought, maybe I can. So the first question I have to ask you, because when I saw you submit that, that's a pretty intriguing title.


Debbie Weiss: Well, thank you.


Mike Capuzzi: So share a little bit more about that title, how you came up with it. And then, if you don't mind, share some details about the book and, you know, who should read it and what you think that targeted reader would get from it.


Debbie Weiss: Sure. So the title really came from kind of the story of my life. You know, I was so afraid of everything. I had a lot of limiting beliefs. You know, if I was seen, I would be judged. I'm not good enough, you know, all. All the things that we all have, right. In some form or another.


Debbie Weiss: And so whenever anything was presented to me, it could be big or small, you know, do you want to try skiing or do you want to, you know, change your career? No, that was my first knee jerk reaction. Right. And what I've learned is, look, that's still kind of like. That's the first thing that crosses my mind. But if you wait 1 minute, 1 second, what happens? Then? You say, well, wait a minute, and then you can talk yourself into it. Well, why can't I do that? I've done this, this, and this. What's the worst thing that can happen? But you need to have that second thought, right? So that's where it comes from. On second thought, let me think about this.


Debbie Weiss: Yeah, maybe I can give it a try. So my book is really a compilation of stories of my life divided into three parts. The first part being, you know, my childhood and how I did develop those limiting beliefs. The middle part being, you know, continuing kind of those challenges and what I viewed as challenges. And now I think, like many of us, if I looked back, I'd say, no, I don't want to live through that again. However, you see how you grew during that time. And then the third part is my journey from that aha moment to where I am now. As far as it's so funny, I thought that my ideal reader was someone like me, a middle-aged woman who thought, oh, this is it, you know, so, you know, it's fine.


Debbie Weiss: It's almost like I feel guilty. My life is pretty darn good compared to other people. What am I have to complain about? But what I found so interesting is that it seems to resonate. You know, one of my sons has. Is in college and like all of his girlfriends, friends that are girls read it. Of course, my son didn't read it, but the friends did, and they loved it, too. And then I had a 70-year-old man who loved it. So, you know, I think anybody who has those limiting beliefs or those thoughts of, well, it's too late, right? It's too late to do that.


Debbie Weiss: No. I'm such and such an age, or I'm at this stage of my life, I should be retiring now, not learning something new. And anybody who really feels like them. They've. And they might not recognize that victim mindset.


Mike Capuzzi: I know you have a podcast now. I did not check it out, but is the podcast Debbie related to the book? Was the podcast before the book? Tell me a little bit about that if you don't mind.


Debbie Weiss: I launched the podcast about three months before the book was published. And so, yes, it is called the maybe I can podcast, and the episodes are there to. To talk about the different ideas. You know, as a matter of fact, I was just planning my one for next week, which is about limiting beliefs. Today, I'm going to be talking about mindset. I have guests that share their stories. Right. Of transformation that are also inspiring.


Debbie Weiss: Yeah.


Mike Capuzzi: So you knew the book was. Obviously, you were working on the book. I want to dive into this a little deeper because this is very intriguing. It's something I encourage our clients when we help in your past life, you'd be interested. We help business owners publish, you know, lead generation books, etcetera. This idea of wrapping a podcast, whatever that may be, around a book, I think can be a very smart strategy for a lot of people. So it obviously was intentional because you knew the book was coming out. What was the thought process there, Debbie? What were you looking to do with the book and podcast and what, you know, does it tie into what you're doing today?


Debbie Weiss: Sure. Well, I was certainly with my podcast, looking to build my audience. Right. I mean, the whole social media thing, I do it. I can't stand it, to be honest with you. You know, it's. It's hard. It's a lot.


Debbie Weiss: And I feel like through a podcast, people really get to know you better, right? I mean, than just a social media post or a minute video. You know, they. When they hear you and if they relate to you. And the funny thing is, you know, that's how I found my book coach was through a podcast. I found somebody else that started me down this whole road and wound up taking some of her courses from a podcast because I felt like they were my friend. When I heard them talk, it felt like I wanted to know that person. Right. We've all landed on podcasts, and you're like, yeah, there's something about that person I just don't care for.


Mike Capuzzi: Hopefully not this one.


Debbie Weiss: No, of course not. Those other ones.


Mike Capuzzi: Those other ones.


Debbie Weiss: Thank you.


Mike Capuzzi: So it's been, what, eight, nine, probably seven or eight months since the book was released, August of 2023. Tell me a little bit about what you did either then or now, because obviously now you're starting to realize, you know, writing the book, obviously it's a, it's a challenge, but marketing and promoting a book is, I think, a bigger challenge, in my opinion. Tell me more. I mean, you did the podcast. Tell me what you've been doing to get the word out about your book.


Debbie Weiss: I couldn't agree more, and I was not prepared for what a challenge it was. I mean, when I look back and I thought writing my first draft was the hardest part, that was the easiest part. And I'm trying to tell myself that now as I'm writing the second one. Don't complain. What are you doing? This is the easy part. So for me, I actually tried to do a podcast tour. I went on as many podcasts as a guest as I possibly could, and I have not even counted how many I've been on. I would guess maybe about somewhere between 40 to 50.


Debbie Weiss: I also got lucky enough to have a very small segment on the Kelly Clarkson show at the end of November, and that was the one thing that really boosted my sales. But it was only for a month. The bump was only that first month. And so that just goes to show there. I got on a national show. You would think fantastic. But no, it's just still a constant work in progress.


Mike Capuzzi: So how did that happen?


Debbie Weiss: It was actually a connection through my book coach and because I've been a family caregiver, and it's a lot of my story, even though I don't really write excessively at all about it. In my memoir, it was November is national family caregiver month. And so she had me on a small segment to talk about that.


Mike Capuzzi: It's interesting, we've had some clients that have gotten on tv, not national, but more like local tv, and they said the same thing about the sort of the focus of the hit for their books. They see a spike, and I guess it's just because we're all inundated with so much stuff. Only a day or two later, people kind of forget they're on to the next thing. But at least you had that opportunity. It's a great opportunity.


Debbie Weiss: Yes, absolutely. And I was actually on two other local shows as well. And, you know, I, I don't even know if I really saw a spike. Maybe I sold a few books.


Mike Capuzzi: It's still part of the thing, though. It's, you know, rising tide lifts all ships, in my opinion. So it's, it's, you know, it is good exposure. And plus, and you may have found this even with your own author journey, you never know who you may have impacted on those shows. Right? You don't, they may have bought your book. They may have read it. Most people don't reach out, but it's just part of the, I think, the necessary path that book authors should be on and want to be on. So you had mentioned you are working on a second book, so I probably don't want to talk too much about that.


Mike Capuzzi: You might not be ready to, but can, can you give us a little insight there? Sure. What's the focus?


Debbie Weiss: So it's not. So when I, you asked in the beginning, is it a memoir? My current book, and it was a big decision when I was writing it to decide what is it going to be? Is it a self-help book at the end of each chapter? Am I going to offer, you know, tips? And I decided not to. So now the second book is going to be more in that self-help genre, even though I seem to, as I'm writing, like, I just, I just tell my stories with a bit more, you know, specificity about the topic at hand in the chapter, and then I do have, you know, activities and stuff to complete at the end. So the first book was more inspirational, and the second is, well, how did you do it? How did you get from a to b?


Mike Capuzzi: Are you finding it to be a different, a different process for yourself? Is it easier for you than the memoir? Do you find it easier?


Debbie Weiss: So much harder.


Mike Capuzzi: Oh, really?


Debbie Weiss: I do find it a lot harder because I found it much easier to write about my own personal experience. You know, I find, like, when I'm talking about mindset, I feel like, oh, that person said that, you know, and because I'm, you know, reading and in that world, I feel like I'm just spitting out and trying to figure out how to rephrase something that somebody, a million other people say. And so that's the thing. Now I have to do less story in each chapter and more of the other. And I'm finding that very, very challenging.


Mike Capuzzi: That is really interesting insight because I've never written a memoir. I've published 20 books, but I've never written a memoir. And I would think, I don't know if I could. I'm much better at the other kind, sort of the nose grindstone tactical. So it's really, I'm always mesmerized. I just interviewed an army veteran he wrote about his time overseas in Afghanistan and how traumatic it was. And he was sharing about this storytelling that was recorded, required to, you know, to share his message. And I'm just thinking that would be.


Mike Capuzzi: I would find that, personally, I would find that hugely challenging.


Debbie Weiss: That's so funny. Are you the kind of person who shares when you, like, talk to people? Like you're open to sharing your. Well, maybe that's why I'm. I'll tell you anything. Ask me before every interview. There are people like, is there anything you don't want to say? No. No. I'll pretty much say it all.


Debbie Weiss: So maybe that's it.


Mike Capuzzi: That's actually. That's. That is the key insight. I mean, it's not that I'm not a social person. It's just I tend to be a person. A few words. And I have a family member.


Debbie Weiss: I do. Mike. Oh, sorry. Maybe you need to do it.


Mike Capuzzi: Probably. Probably. And I. And I probably could. It's just not my natural inclination.


Debbie Weiss: Yeah.


Mike Capuzzi: Though I do have a family member who's the complete opposite of mine. And whenever we have dinner, you know, family dinners, it's like he take. He consumes the entire conversation. But I digress.


Debbie Weiss: Yes. So, Debbie, what?


Mike Capuzzi: I'd love you to share, because, again, you're such a relatively new author, is there a word of either encouragement or something you'd want to warn other people who might be where you were a year or two ago about either the writing, the promotional journey? Just something to say, hey, here's how I did it. I probably wouldn't do it again. Maybe that way, or I would do it differently.


Debbie Weiss: You know, I think that, as I said earlier, I didn't realize how difficult the promotional part would be. But even. And so I guess my word of advice would be, don't think that you're going to set the world on fire with money coming through your computer or through Amazon or. However, that's another whole thing, how you sell it, because that's not going to happen. However, to hold my book in my hands and to know that I actually accomplished this, that I'm a published author, and I still find that difficult to say that, like, when people call me an author. Well, I'm not really an author. Yes, I am. Why can't I step into that? That is an incredible accomplishment.


Debbie Weiss: So as long as you're not thinking that this is going to shake that money tree for you as far as book sales, unless, you know, look, we all know there are other ways to do it. And like you said, you do it promotionally, and a lot of people do it to, you know, use it as a promotional tool. I think that's what it is. It's to help you sell your other stuff.


Mike Capuzzi: Are you doing that now? Is that part of the bigger picture now?


Debbie Weiss: So I didn't have other stuff. I mean, that's the honest answer. The honest answer was is that when I originally wrote the book, in my mind, it was to help me get paid speaking engagements, which I have done a few, but, you know, that's a challenge as well. So I am in the process of creating a digital course. I do have some private coaching options available, but I've been now working on book two and starting to work on the course.


Mike Capuzzi: Yeah, I mean, it makes sense based on what your background has been and what you've gone through. So, yeah, having that coaching consulting courses, I think is a nice addition to the podcast and the book. So congratulations with that. So, Debbie, I think you've already shared it, but I'll ask it anyway. What has it meant to you to be a book author?


Debbie Weiss: I have shared it. It really, it's an incredible, incredible feeling of accomplishment that I don't really think I've ever felt before, or maybe one other time, but it's in a different way. And with the memoir, it's also something that I'm leaving a legacy to my children and their children. And I think what I've also done is my boys are in their early twenties, is to show them that if you set your mind to it, you can accomplish anything. And I love that they're proud of that and they've seen firsthand what you can do.


Mike Capuzzi: That is awesome, Debbie. So can you share with our listeners? How can they learn more about you? Where can they see your or listen to your podcast? And where can they get the book?


Debbie Weiss: So everything from my website, it's the easiest way. And it's Debbie dot.


Mike Capuzzi: We'll link that in the show notes. Debbie, again, congratulations. And soon you're going to be a multi book author, so you'll be able to proclaim that. But thank you for your time today.


Debbie Weiss: Oh, thank you so much for having me, Mike.