On a recent edition of First Draft Friday, I talked with author Debbie R. Weiss about how she stepped through self-imposed boundaries of fear and anxiety to write her memoir, On Second Thought, Maybe I Can.
Here are some key takeaways from my conversation with Debbie:
1. Embrace unexpected paths
Debbie never intended to become an author. She described herself as a “math numbers person” who believed she lacked creativity. However, a transformative period in her life led her to realize she had a story worth telling.
2. Recognize the power of intuition
Debbie’s decision to write her book was influenced by an unexpected moment of intuition. She felt a strong connection to an author coach on a podcast and decided to follow this newfound inspiration.
3. Overcoming self-doubt
Like many new authors, Debbie grappled with self-doubt. She worried about her lack of formal training and feared her writing wouldn’t be engaging. However, by sharing her initial stories with her writing group and receiving positive feedback, she gradually built confidence.
4. Writing as a therapeutic process
Writing her memoir proved to be a cathartic experience for Debbie. Recounting her life’s challenging moments, she found the process healing, allowing her to release pent-up emotions and gain new perspectives.
5. The importance of structure and flexibility
Debbie struggled to figure out her book’s structure. Initially, she felt compelled to write her stories in chronological order, which hindered her progress. Realizing she could write in any order was liberating.
6. Leveraging support systems
Debbie benefited greatly from participating in a writing course and connecting with a supportive group of fellow first-time authors. This environment provided her with the accountability and encouragement she needed.
7. The value of journaling
Though initially resistant to journaling, Debbie discovered its benefits through prompted exercises and later, free-form journaling. This practice helped her unlock her writing potential and gain confidence.
8. Pushing through personal challenges
Debbie continued writing even during her husband’s terminal illness, finding solace and purpose in the process. Embracing writing as a means of escape and expression can be particularly beneficial in navigating personal challenges.
It was a great discussion, one you won’t want to miss! Click below to watch our 30-minute recording and hear the questions we answered from the live audience. Keep scrolling if you’d prefer to read the transcript.
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Find out more about Debbie at DebbieRWeiss.com
Enjoy the show? Check out our past First Draft Friday episodes.
TRANSCRIPT:
Alessandra Torre: Welcome to First Draft Friday. I am your host Alessandra Torre with Authors AI. And today I am joined by Debbie Weiss, who is going to be talking all about breaking through your self-imposed boundaries, overcoming hurdles to write your first book, or potentially your 10th book wherever you’re at in your process. And Debbie’s book is titled On Second Thought, Maybe I Can. So I’m excited to talk to her about her book, her process, and the boundaries that she broke through. So welcome so much to the show. It’s great to have you here, Debbie. To all of our listeners watching, don’t be shy. Feel free to comment and interact with us during the broadcast. But, Debbie, do you want to just tell the audience a little bit about yourself?
Debbie Weiss: Sure. Well, first of all, thank you so much for having me. I’m very excited to be here. I’m always excited when I go on a show that’s about authors because I still can’t believe that I’m one of them. So yes, I wrote my memoir. On Second Thought, Maybe I Can. I will just tell you that I never thought that I would be an author. I never had any intention of being an author. And my whole life I was a math numbers person and thought I didn’t have a creative bone in my body. But you see, you never know.
Alessandra Torre: Now you’re here. I love that. I love that. I also never thought I would write. I was not a numbers person, but I never thought I would write. I thought authors lived in New York and were born into a literary family. And had lunch with agents and stuff. I don’t know, I thought it was this whole thing. So, and welcome, I’m seeing some of our regulars in the audience. Hi, Chris. It’s great to see you. So what prompted this book? What was the journey that got you there? Not all the way to the end, but the journey that made you say, you know what? I’m going to write a book.
Debbie Weiss: Sure. Well, I was kind of going through a transformative process of my own figuring out what I want in life. I spent all of my life taking care of other people. I’ve been a family caregiver for over 40 years to my dad, my husband, and my eldest son, who has disabilities. And I had an aha moment which kind of sent me down this path of exploration. And I have a little bit of a story. And people my whole life would always say, oh, you should write a book. I mean, everyone says that, right? Oh, yeah. Yeah, someday I will, but I never really meant it. And all of a sudden, a couple of years ago, I said, figuring out my path and realized that I had a message that I did want to get out to people. The book idea kept showing up in front of my face and I would say, that’s ridiculous. And one day I was listening to a podcast, a podcast that I don’t typically listen to, and the host was interviewing a guest who helped first-time authors get their story out there. And I felt she was speaking to me, and she was someone that I felt or would feel comfortable with, and I kind of just gave into my intuition and said, I think this is a sign. And after the podcast was over, I contacted her, and I did connect with her, and I told her my fears. I was comfortable sharing my fears, saying. I don’t know how to write. How is this even a possibility that I could write a book? And that’s how it all started.
Alessandra Torre: So what if you are comfortable sharing what were your fears? What were the major reasons why you said, I can’t write a book or I’m not going to think about writing a book? What were those fears?
Debbie Weiss: I have no idea what I’m doing. I felt that I needed formal training. Honestly, and you’re younger than I am, so I don’t know if these books are still out there, but, growing up, I learned to read on. See Dick Run, See Jane Run. And I really envisioned that’s what my book was going to sound like. And who would want to buy that book? I felt I was not a literary genius. So who would want to read that? And then I thought to myself, what do I like to read? Do I like to read the classics? No, I don’t. I mean, I’m going to be honest. I want to read a relatable book. And so if that’s what I want to read, then there must be somebody else out there who’s going to enjoy it.
Alessandra Torre: I agree with that. And I think I meet so many people, especially younger people, especially people in their 20s and 30s who say, oh, I’m not a reader. And I think a lot of people, they’re not readers because the only books they’re exposed to are the books that we read in school. And those are the classics. I’m with you. I don’t want to read a classic. It’s hard for me to read a classic. I don’t enjoy reading. I like contemporary fiction. People think they don’t like to read, or they might think that they can’t write this or don’t want to write this. And really, they just haven’t met their type of book yet. And those that are voracious readers, we all know we love to read because we found what we love to read. But I think so many people, they only read what’s required to read and then they have to analyze it to the nth degree. And that takes all that fun and love out of it. We did have a question on YouTube. From Danny. He said, what was the name of that podcast?
Debbie Weiss: So it was “Powerhouse Women With Lindsay Schwartz.” The podcast is geared towards female entrepreneurs.
Alessandra Torre: So you did end up working with that where they are writing coach. Is that what they were?
Debbie Weiss: Yeah, yeah. So actually she was just about to launch a 12-week course for first-time authors and simultaneously, out of the blue, my husband was diagnosed with terminal blood cancer. Before that, he had been ill and had physical as well as mental illness. So it had been a super tough time in our lives. But this diagnosis was unrelated to anything else. I didn’t know what was in store. I do work full time. I was able to work from home and luckily was able to stop going into my office and really not having to work too much, but. The course was going to start and I hadn’t signed up for it yet. And then we got this news and I went to my therapist and I said, I’m embarrassed to even tell you that I’m considering taking this course during this time. I told her my fears. What if there’s homework? What if I have to write a certain amount of words, or whatever it is, each week, and I can’t do it because of my situation with Gary, my husband? And what if we go to the group and they make us read our work, and then people are going to judge me? I had so many fears and I was a good student, so I didn’t want to sign up for this class and not be able to show up and do all the things that I was meant to do. And in the end, she said to me, I actually think that this is the perfect time for you to do this because you need something completely separate. And she was right. So I took the course. It was a small group of people who were all in the same boat, all writing.
Alessandra Torre: All the same fears.
Debbie Weiss: exactly, exactly. And so, so quickly those fears were taken away. And I looked forward to our meeting each week. There are different people in the group now, but today at 1:00, I still have the meeting, and it’s something I look forward to every week. And what I did was since my life and my schedule was all over the place, I was very dedicated to making sure each day or most days I wrote for at least a period. Some days it could only be 20 minutes, other days maybe it was an hour. When they had co-writing sessions I really tried to attend. I needed that accountability. And, my husband lived for six months and when he passed away, I was about two chapters shy of finishing.
Alessandra Torre: Wow. Wow. That’s amazing. I have two things to say. One, I think one of the best books I ever wrote was when my husband was going through cancer. He survived. And I’m sorry for your loss. But it was the same thing. We were spending our days in chemo and radiation and, all of that, and this was my an hour and a half each day where I closed my door and I could escape into this other world, and I could focus on that, and it would give me something to think about, other than all of the things that we were dealing with financially and health wise and everything else. So I think writing can be such a fantastic escape. Now, you were writing a memoir, so it might not have been as much of an escape because you were writing about the things that you had gone through or were going through. But at least from a fictional standpoint as a fiction author for me, writing a light, funny story that had absolutely no grounds in what I was experiencing was it was my salvation during that time and, something I really needed. The other thing. And so do you feel comfortable sharing the name of the course that you took?
Debbie Weiss: Oh, sure. Oh, yeah. Yeah, yeah. So Lauren Eckert is the woman who was the coach, and it’s Burning Soul Press.
Alessandra Torre: Lauren Eckert, Burning Soul Press.
Debbie Weiss: So your first fear, and I have to say, I do a workshop each year for newer authors. And the first thing I ask them is, what are the reasons why you haven’t written your story yet? Then I give them five multiple choices and in over half self-doubt is the number one. They are only allowed to pick one reason. Self-doubt is the number one. The others are, I don’t have time. I don’t have money. I don’t know how to do it. I don’t even know if that’s an option. So it falls under self-doubt. But, you certainly weren’t alone. And one of the nice things about joining a program is that you quickly realize that everyone else has similar concerns and doubts that are facing them. But when you started how did you go from, I don’t know anything and I don’t even know where to start. And I have this story that I want to tell, but I don’t even know how to tell it. What were the first steps that you went through that made that manageable and gave you a path forward?
Debbie Weiss: Boy, one of the hardest parts is not knowing. I had so many questions. And along with the group, there was a course that took you through a series of exercises that helped you kind of put it together. And it took me a long time to figure out what the structure is. And I really had a lot of roadblocks with writing until I figured that out. And I had to decide if I wanted it to be just stories. Is it going to be a memoir? Is it going to be self-help? I didn’t understand since I was new to this, what is the difference? Am I going to tell a story? And then am I going to come out of the story and give a message or give an exercise? So I was trying to figure that out. Would the structure of the book just with a bunch of stories not really linked together, would that work? So I played with a lot of different things. And in the end, I did have help from Lauren, from the group, from the course. And it did take a while for me to decide what it’s going to look like. And it is just a compilation of stories. It is not a self-help book. It is just stories of my life that, in the end, are inspirational to someone realizing that you have the power to change your life regardless of what’s happening.
Alessandra Torre: I love that. I can see it being very difficult. I’ve never written a memoir, but I can see that being really hard especially if you are straddling the self-help line, and a lot of memoirs are, figuring out that figuring out that structure. So when you said it took you a long time what is a long time? Did it take weeks or months to figure out the structure? Did you end up writing something and deleting it? Were you working off an outline? What was that process?
Debbie Weiss: It probably took a month to figure it out. And no, I don’t think I ever really had to delete anything. Maybe just move things around. But once I had the outline, oh my goodness. Then it got so much easier. And the other thing as a first-time author. Maybe it’s my numbers thing, I don’t know. I had in my head I had to write it in order. Why? Why did I think that? I mean, especially me, because of it. It was a bunch of individual stories. And when I realized I didn’t have to do that, that was so freeing. Each day then, I would open up my computer, look at my outline, and say, what do I feel like talking about today?
Alessandra Torre: Yeah, I think I’ll write…
Debbie Weiss: Yeah. I’ve never written a fiction book, but I’m sure that’s very different, obviously, than this. There you don’t really have much of a choice, I would assume.
Alessandra Torre: Yeah, I say yes and no because if you’re pantsing, if you’re not working off an outline. It’s hard to write out of order because you don’t know what’s happening until you’re writing it. Oftentimes you’re figuring out where you’re going. But for someone with an outline… So I was talking to a new author the other day, and she was really struggling because she didn’t know what she wanted to happen in the next scene. She knew what she wanted to happen five scenes from now, but she didn’t know how to get from one place to another smoothly. And she was new. I mean, she’s only written five scenes in her life, or ten scenes in her life. It’s still a new thing for her. And I was like, just go start writing from where you know you’re getting to. Go from there. And she’s said, what do you mean? And it was the same thing. I can write out of order or I can just skip forward?! And I said, yeah, you can just come back and write those scenes later. And it was such an unlocking thing and again once you finish the book, then it’s much easier to say, oh, I’ll use these as a connector or you’ll know more. You’ll say, oh, I need to add a hint to something happening, so I’ll put it in there.
Debbie Weiss: Exactly.
Alessandra Torre: And so I love that. We do have a question from Chris on YouTube and he said, “How did you overcome any self-doubt while writing a book of such heavy stories? Did you just keep going? Road on your book writing ignorant, so to say?”
Debbie Weiss: Good question, Chris. So I think once I got started I wrote a couple of stories and I shared them with Lauren in the group and I got positive feedback, which was helpful. I think that started to alleviate some of the self-doubt and then also the realization of, to stop judging myself. I’m just putting this on paper. Nobody’s reading this first draft or the public’s not reading this first draft. It’s okay if I wind up scrapping it. It’s okay. This is all a learning process. Some of my stories were heavy, actually. I mean, I don’t think as a reader they were. But for me, just as you said before, putting myself back in those situations, some things were remembering how I felt when I was five years old. It was amazing. I never understood when people would say how cathartic, that is. Yeah. I just didn’t understand until I did it. And then I realized to share the story with impact, I had to let the reader know what was going through my mind, how I was feeling, and so I had to put myself back there. And in the end, there were some days, Chris, I’m telling you, there was one. There were a couple of stories that after I was done or in the middle, I had to stop and cry. But it was a release and so it helped. It helped to keep going because it was cathartic, and even though it was heavy, it was still different than what was going on with my husband.
Alessandra Torre: Is. Did it cause you to look at things and sometimes some things in the past in a different way because you were looking at telling the story? I would just be curious if it would allow you to maybe forgive. I mean, I don’t know the situation, so I don’t know what I’m talking about really. But yeah, I’m curious if it caused you to kind of walk in different shoes as you were going back and reexamining that event and, the situations around it.
Debbie Weiss: Absolutely. Absolutely. I can say just figuring out what stories to put in the book where I would have a story. I didn’t even realize I had a story to tell. Yeah. it really is a whole process of self-examination and, thinking about, well, what happened in my life to cause me to have this limiting belief, to cause me to make my had this victim mentality that I had for such a long time, what were the circumstances? And so, as I did write it, for sure, sometimes I had some aha moments like, ohhhhh. So that’s how I felt. Or, a lot of the story had to do early on with my mother. My parents were divorced. My father had a stroke when I was 17, and I wound up being his caregiver for the next 30 years. And so, I had some maybe unresolved feelings towards my mother, even though she didn’t do it on purpose to put me in this situation putting myself back. My mother was 39 years old. I’m writing it at 59, thinking, gee, 39, and understanding, trying to understand from my mother’s perspective a little more what was happening. It let me release some of that resentment that I had.
Alessandra Torre: That is so interesting. And so in the writing group, you posted some early now. From a fictional standpoint. We have scenes, right? So we’re writing in either first person or third person. I’m assuming you were writing in first person.
Debbie Weiss: Yes.
Alessandra Torre: And, were you telling it past tense, For example, in the summer of what you might call it I was living here. I was doing this one day. This happened. Was it that?
Debbie Weiss: Yes.
Alessandra Torre: All right. So how long would typically a scene be for you?
Debbie Weiss: You know what? That was another question that was another interesting thing that I hadn’t thought of that was brought up. Do the chapters have to be equal in size? Right? Because some of my stories were not so long.
Alessandra Torre: Yeah.
Debbie Weiss: Yeah. At one point, once we were in the editing process, the editor wanted to take two of the stories and combine them into one chapter. And I didn’t want to do that because I felt that didn’t happen anywhere else. Who cares? I never think about it as a reader. I’m always thinking, as a reader, am I noticing this? No. Oh, this one’s only three pages and this one’s 12. Yeah, I don’t care.
Alessandra Torre: I agree with you wholeheartedly.
Debbie Weiss: Yeah. So, I just told the individual stories, wrote the individual stories, and was pleased.
Alessandra Torre: So if I go through your process, you figured out your structure, you wrote an outline. You then just started going through and cherry-picking and writing the scenes in whatever order you wanted. You wrote all of the scenes in the outline and then what was your work count then?
Debbie Weiss: Oh, gosh. I mean, in the end, I wound up with 83,000 words.
Alessandra Torre: Wow. That’s that’s a significant. Yeah.
Debbie Weiss: That’s what Lauren said.
Alessandra Torre: After edits and everything.
Debbie Weiss: Yes, I think after edits, that’s what it came down to. It might have been 86,000 or something.. Now, I did add an epilogue three months after my husband passed away.
Alessandra Torre: Yeah.
Debbie Weiss: When we were in edits I added that. So yeah that’s what Lauren said. She said for someone who said they couldn’t write and a first-time author, this is a lot of words. I said, well, I talk a lot, so that makes sense.
Alessandra Torre: I love that, someone said, “Writing a book for the first time around is quite an accomplishment. Have you ever in your life kept a journal? If so, would you say that practice helped you in any way with your writing later in life?”
Debbie Weiss: Oh, I’m so glad you asked that question. I had never kept a journal, ever. I mean, as a kid, I always wanted the little diary with the lock, but, you know nothing. I never did it long term and i, my time of transformation or I guess we’re always still transforming. Journaling was something that I was introduced to. I was very resistant. I mean, just the thought of looking at a blank piece of paper. And I’m supposed to write something that was terrifying. I could not understand how anyone could do that. I don’t remember what I was doing, I think I was taking a course and in the course, they sent you a journal, but it had prompts, so that was a little less intimidating to me. I still didn’t like it, but I stuck with it.
Alessandra Torre: What was it that felt like a chore?
Debbie Weiss: I think it was more who did I think was reading this journal and grading me? I think it was that kind of thing. What if I write the wrong thing? There was a part for affirmations. I’m not sure what that means. What if I write the wrong thing? Am I allowed to write the same thing two days in a row? That kind of thinking. Once I got past that and permitted myself to do whatever I wanted, I really started enjoying it. It actually was probably about three months before I heard Lauren on the podcast. I had heard another podcast that talked about the benefits of free-form journaling, and I thought to myself at that point, okay, now, you’re a journaler, you’re doing this, just try it. And I sat down that first day with no prompt or anything, and I started writing. I remember what they said, so start writing. I have no idea what I’m supposed to be saying here. That’s kind of how I started. I’m telling you, I don’t even know if it was 15 minutes later when I looked up, my hand was hurting. My writing took a story from I don’t know what I’m going to say to some deep thing that I didn’t even know I was thinking about, and that was it. I was hooked, and it honestly was because of that. That gave me a teeny bit of confidence that I didn’t want to admit. Maybe I can do this because look at what I’ve just written.
Alessandra Torre: Yeah, there are words in me. There are things that can come out. Okay, so we only have 3.5 minutes left. And we do have a few more questions. So David said, “In therapy, there’s a process called journaling. It sounds like maybe you were doing something similar.” That’s not really a question, but just chiming in. Danny said, “Did you ever think, will anyone want to read this?”
Debbie Weiss: Oh, gosh. Please. All the time. All the time. Who’s going to want to read this? And the fear when you let someone read it for the first time? Oh, my gosh, that was intense. Just giving it over to the editor. I think she was going to have it for two weeks. And sometimes I would see her on Zoom or in something else. I said, oh, Allison. So how’s it going? Just baiting her? Please, please just give me something. So that was a very long two weeks of my life. But yes, I definitely think. Did anybody want to read that? And also, I’ve shared some extremely personal things, that we didn’t even really talk about that portion of doing something like this. It is very scary.
Alessandra Torre: I can’t even imagine. So was it hard for you? Just letting your family and friends know about it with this awareness that they were going to have this intimate look into your life, into your history and your feelings?
Debbie Weiss: Absolutely. And different people I had different feelings about. Right. Yeah. What they were going to think and how they were going to perceive this. And, there was one story in particular that I did not have in the original outline because it was something I was too ashamed to write about, and really nobody knew. Nobody knew the extent of the situation. And it was about money. And in the end, I decided that if I’m writing this to inspire people. I need to be completely honest and completely open because if I don’t write about that, maybe I’m shutting off a whole group of people who could relate to this.
Alessandra Torre: Yeah. Who needs to hear it?
Debbie Weiss: Yeah. And I said, if you’re going to do it, you’ve got to do it 100%.
Alessandra Torre: I agree with that. And I sent an email out to my list in the last year and I had had a failure and I had talked about that and I was so not sure about sending that because gosh, I really don’t want to share. I mean, I feel bad about this now. I’m sharing with others. But I thought maybe this would help. I did learn some lessons. Let me share. I got so many responses from those who were so appreciative. So yeah, was it also a little cathartic for you to write that?
Debbie Weiss: I was scared at that point. What I found now afterward is I cannot believe I just gave a talk at a women’s expo and I opened with the story about the money. And afterward, I thought, can you believe you’re standing up here talking to 100 people, telling them the secret that you said you would never share? And now. So now it feels amazing because it’s something that I lived with and suffered with for so many years.
Alessandra Torre: Yeah. Well, it was absolutely wonderful to talk to you. Thank you to everyone in our audience who was here and who participated. If you’re watching the replay, thank you for watching the replay. Please leave a comment. And if y’all are interested in reading Debbie’s book, you can find out more about her at DebbieRWeiss.com. Can you just give the name of your book again and where they can find it?
Debbie Weiss: Sure. On Second Thought, Maybe I Can. Sitting right back there and it’s on all the normal places online Amazon, Barnes and Noble.com, that kind of thing.
Alessandra Torre: Fantastic. Well, thank you so much, and thank you to everyone who joined us. We’ll see you in another two weeks at another First Draft Friday. Thank you again, Debbie.
Debbie Weiss: Thank you.
