Vulnerability and Resilience | Debbie Weiss on Finding Your Voice

Debbie Weiss, former accountant, author, and podcast host, reveals how radical vulnerability became her path to authentic leadership and purpose. After a lifetime of caregiving and self-doubt, she found her voice through storytelling. In this episode, hear how she reclaimed her narrative, built a platform that matters, and discovered that your second act isn't about reinvention—it's about finally becoming yourself. Her memoir, *On Second Thought... Maybe I Can,*, and her podcast prove that resilience isn't loud; it's quiet, persistent, and deeply human.
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Speaking of Phenomenal is created and produced by Amy Boyle. Podcast artwork by Amanda Eich. "Woman" by Tiffany Villarreal, used with permission. Be sure to subscribe, rate, and review and share the podcast, and stay tuned for more inspiring conversations. Support the show with on Patreon.

Transcript

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Amy Boyle (amyboylephoto) (00:00.088)
Have you ever looked at a challenge and thought, maybe I can't? Well, what if I told you that maybe you can is actually the starting point to an extraordinary life. Welcome to the Speaking of Phenomenal podcast. I'm your host, Amy Boyle. Today we're thrilled to have Debbie Weiss, author of On Second Thought, Maybe I Can, join us. Debbie's an author, podcaster, and Canfield certified trainer who's mastered the art of turning challenges into

Debbie's insights will leave you energized and ready to sprinkle a little more heart into your world. This is the Speaking of Phenomenal podcast. Welcome to the Speaking of Phenomenal podcast, Debbie. I'm so glad you're here. I am so glad to be here. Thank you so much. And it's so nice to see you again, Amy. Yes, I know. We just recently recorded for your show and it's great to have that familiarity. It's almost like having a coworker. It's really nice. How about you introduce the phenomenal you to our listeners?

Ooh, boy. Well, thank you. So hi everyone. My name is Debbie Weiss and I am phenomenal because for the first time at age 60, I became an author. And I think that's a pretty big accomplishment, especially for someone who

I been a family caregiver for over 40 years. started when I was 17 and my 45 year old father had a massive stroke. And it's continued on over most of my life. When I turned 50, I kind of had an aha moment where I said, if not now, when? I've been giving my life to everyone else as I think many women do and

there's anything wrong with that, but we also need to prioritize our own needs. And something about the number 50 for me, made me think about my own mortality. And since that time, I have been on a journey of self -discovery and that's over a decade, cause I'm going to turn 61 in a couple months. And it's been amazing, just amazing. and like I

Amy Boyle (amyboylephoto) (02:15.054)
with the author thing, it's led me down roads that I never dreamt of and found things out about myself. I never knew existed. I find that truly phenomenal, obviously. And I think we're very similar in the sense I also at 50 a few years back was like, big pivot. Like what is going on at that point too? My mother was ill. I had just lost my father. The kids were almost out of the house. And I was

Who am I? And I think a lot of us don't really get, spend that time to figure that out and kind of treat it like this great jumping off point, right? None of these things that we try or dabble in or whatever have to stick, but that's only being part of our collective experience that makes us more interesting, more unique, more alive. Tell us about the book. On second thought, maybe I can. The title alone is just like, I love

Well, thank you. The title came from really the story of my life because looking back, one, I was always a nervous Nellie, but two, for so many reasons, limiting beliefs I had about myself, I never wanted to put myself out there. So whether it was something as simple as, you want to go, I don't know, on that roller coaster versus do you want to, you know, move or start a new career, anything

was presented, my knee -jerk reaction was, I can't, I can't do that. And what I've discovered is if you just take a pause and a breath and give it a second thought and say, well, wait a second, why can't I do that? That that's when your life actually changes. And so that's where the title came from. And I decided

You know, when, when the whole idea came up and it was through a lot of different things that happened. And I said, you know, I don't see why my life is going to be inspiring because thank goodness I have not, you know, been a victim of, of abuse or violence or, know, I have all my limbs. Like I just felt like I didn't have some, you know, big T trauma. And what I realized

Amy Boyle (amyboylephoto) (04:42.03)
Thank goodness, most of us don't. So maybe it's more relatable to listen to someone who's just had little trauma after little trauma, and some of them are big, right? I took for granted what I've been doing the last 10 years. And I was actually just on another call where someone was saying, isn't it sad to think about those people who aren't taking this journey?

And I thought, isn't that what we're here to do? To let people know, Hey, there's more out there. You've just got to come find it for yourself. And it doesn't have to be some massive goal like Everest. could literally be like you said, putting yourself out there a little bit more than you did the day before, you know, getting on. We'll get into talking about podcasting because I definitely think that's changed my life and my worldview and my connection with others. And it feels

perhaps the same for you, but like, these are things that no one can make us do them. And when we do, and other people are going to reap the benefits of us being a braver version of ourselves. What have been some of the most wow things that really took your breath away when you on second thought, maybe you can. There's actually been so many. I would say when I was in my early thirties,

did do a big career change, moved from New York to New Jersey. And even though that doesn't sound far, from where I moved to New York to where I am in New Jersey, it actually is miles, not just, I don't mean miles, physical miles, but very, very different. And, you know, I went from something that a career that I was comfortable in, it was safe. had, I'd been a CPA, I'd been with the same firm for 10 years, right? I like knew my gig, knew my job,

comfortable in it and I became an insurance agent. Why would I ever want to be an insurance agent? I used to joke like nobody wants to talk to an accountant and now who the heck wants to talk to an insurance agent? Like, I guess it took me all this time to brand myself as something else other than that that people might want to talk to. But it was very, very scary. And once I actually started

Amy Boyle (amyboylephoto) (06:57.826)
the challenges just kept on coming. it was, honestly, if it weren't for my husband and my friend, it would have been very easy for me to just crawl back and crawl back over the border back to New York and knock on the door of the firm and said, take me back. But in the end, because of perseverance, because, you know, the reason that I did do it was for that freedom to be your own boss. It has given me

everything in my life. It has given me the freedom to take care of, my oldest son was diagnosed with developmental delays and then many other things. And it gave me the time to be able to spend with him and plan his therapy. And then my husband got sick and you know, all the things and I didn't have to worry about a boss or taking leave or just so many things, but it was not easy to get there.

And I'm really proud of myself that I did it. think the main point of this podcast and a photo project I did a few years ago is to give ourselves permission and a platform to stop and congratulate ourselves. We're so quick to dismiss it like, that was yesterday. What's tomorrow or that fire is put out. Now what do I do? And it's one of those things that these micro changes that become macro changes need to be celebrated.

Even when we're doubting ourselves, we are shining a light and inspiring so many other people along the way. And that's so important for everybody to realize. And I tell this to myself all the time now at other things that I'm trying to achieve. It's so easy to look at someone who's on the other side and say, yeah, look, it came easy to them. they didn't have any struggles. It's not like me, but you don't know what happened before.

It's not easy. It's not easy for anyone. And the prize I think is on the other side when it's no fun when it comes easy, right? It doesn't feel like an accomplishment. Yes, because if it's too easy, it's like, well, I don't know. I think we're born to crave challenge to some degree anyway. Just so if it was handed, then it's not earned or we didn't, or you didn't go backwards two steps to go forward one, you know, all the different things where.

Amy Boyle (amyboylephoto) (09:23.692)
the lessons and the magic happen, right? Absolutely. So tell me a little bit more. So a Canfield certified trainer. So what is that and how does that apply to your business now? When I was finished writing my book, you know, I had heard of Chicken Soup for the Soul. I have to be honest. I don't even know if I ever read one book completely, but I got introduced to Jack Canfield, not in person, but online.

actually was lucky enough to have him read my book and give me some really positive feedback, which was amazing. But what I found out was that he also co -authored a book with someone called The Success Principles. And he has a program that certifies people in his success principles. And when I read The Success Principles, I realized that kind of without knowing it, without

me having while I've been going through this journey, I didn't have a roadmap, right? It was kind of like, let me try this. what is this limiting belief thing? I didn't, you know, I didn't know the names. didn't realize any of this because honestly, this whole personal development thing was all new to me. I kind of thought it was a bunch of woo woo stuff before I started learning more. And when I realized

I don't need to reinvent the wheel. He has the wheel right here. He's just such an amazing speaker, a teacher. So I so relate to that. just love that, that relatability factor. Well, why reinvent the wheel? Right? I mean, if it's tried and true and in a time where you're open to change and we're already like putting ourselves out there, it's nice to have a formula.

to follow that we can build upon. So you said you shared your book with him. We've had a few authors on the show and I always love to hear the process. So what was that like? my goodness. So it was through a program that I actually did with one of his publicists and it was 16 authors, two full days on Zoom, nine hours a day. He and the president

Amy Boyle (amyboylephoto) (11:48.91)
his company read the book and they, well, they didn't read everybody's whole book. have to be honest. They read like, you know, I don't know, 50, 75 pages of the book. And then they shared feedback and you got to sit there and listen while they gave feedback to everybody else. So you sat there quietly for 18 hours.

Well, it went alphabetically. My last name starts with W. I was last. And I sat there listening and I'm thinking to myself, I can't believe I'm on here. This, what was I thinking? Putting myself out there like this. These people that, you know, the other, most of the other people either had written books. I just felt like they were more alerted. They sounded more intelligent than I did. I was literally ready.

Once they were up to someone with the letter T last name, I almost wanted to click leave now.

I was mortified. And you didn't know who was going to speak first, like, you know, whether it was going to be Jack or his president or the publicist. And so the publicist was kind of like the emcee. And then Jack says, well, I know I'm not really supposed to say this, but this was one of my favorites.

Amy Boyle (amyboylephoto) (13:17.612)
And then he quoted, started talking about a particular story that I told, you know, one of my chapters. That was one of his favorites and he knew it. Like, you know, he was clearly had read it and,

Amy Boyle (amyboylephoto) (13:34.05)
Yeah, it just goes to show that lack of confidence that I had. And even so, I started the whole conversation with him by, and this is what I used to say to everyone, I'm a numbers girl. That's where I am. You know, that's all it's been about. I never wanted to write, blah, blah, blah. It was like I was making all the excuses. So he didn't have to make any excuses. I was giving it to them, right? And he said to me,

You'll never say that again. You are a numbers end of words

And I can't tell you what that has done for me. It really has been incredible. know how much influence he's had over the world for all these years, decades now. So that must have been, especially if you're about ready to hit, leave the meeting. You know, I could feel that. I could actually feel that. I was like, yeah. I don't know. I used to be at the end of the alphabet. Now I was a Y. Now I'm a B. It was quite a jump, but

That feeling must have been amazing. How did you internalize that? Were you able to celebrate that after? then follow up to that was what was the first actionable thing you did with this now I am numbers and a words girl mantra, if you will.

I was able to celebrate it. He gave me some other feedback that I was actually allowed legally to put on my book. And so that was actually the first thing that I ran and did. And it was a lesson in you have to trust yourself. You have to trust yourself. You were about, literally, I wanted to press leave. The only reason I did, I don't know why I

Amy Boyle (amyboylephoto) (15:31.788)
I think just embarrassment is the reason that I didn't. And what if, what if I never put myself out there? What if I had never exposed myself like this? I mean, not to mention my book is exposing myself to the world, which I, is very scary, especially some of the stories that I did not want to share. It's uncomfortable. But like you said,

If we don't, then how are we going to share our message with other people? How are we going to have any impact? Because I always think about who's impactful to me, right? What do I find impactful? It's just like going on social media and looking fantastic and making the poses and doing all these things. Do I want to see that? No way. I want to see a real person going through real stuff and sharing.

and telling me it sucked and telling me, then triumphing or hearing what lesson they've learned. That's what I want to hear. And so it reminds me that if I want to hear it, other people want to hear it too. There's so much out there that's so sanitized or everyone's highlight reel is not the reality. And yes, you know, there's a time and place for super polished,

As we're seeing since the pandemic in particular, I think there's this craving for authenticity. With a professional edge, don't get me wrong, I think a lot of people kind of get a little too loosey goosey. It's just as far as like, well, this is the real me. And you're like, well, consider the audience. But overall, I think that is such a benefit. And the more people that have messages to share and can do it from a place

from the heart, which I know hearts mean a lot to you. So that's definitely coming from a space there. And your story about wanting to leave the zoom remind me, our first episode of the season with the podcast I had Jennifer Jones on, and she was the first black woman, Rockette. And she told the story of the day on a lark. She was almost late to go to this audition.

Amy Boyle (amyboylephoto) (17:53.9)
The line went down the block and she really thought, well, but if I leave now, I can make my favorite dance class at this other place. And then she had like a foot out and then went, I got to go back. And she ended up getting a call back and it changed her life and the lives of so many others just by going, yep. You know, that was that, that second thought kind of thing. It's so incredible. I love that. gave me chills.

So I know your connection with like hearts and the sprinkle effect. Can we talk a little bit more about why that message means so much to you and how it's making change out there?

Well, the hearts thing started when I was a little girl and I have no idea why. I just always had an affinity towards hearts and always loved things with hearts. And when I was in college in Washington, DC, back then there was a place called the old post office pavilion that had little boutiques. And one of the stores was a store.

that only sold items with hearts on it. And I thought I had died and gone to heaven. I never wanted to leave this store. I would like harass my friends. Well, let's go to the post office pavilion. They're like, again? And I vowed that someday I would own a store like this and then, you know, life takes over and that's that. And 40 years later, I was

scrolling on something, shopping, right? And I put in the search bar, hearts, because what I want, what I need, just another shirt with hearts, right? And all of a sudden it popped into my head and I realized, my goodness, it's whatever year, 2022 at the time, I don't need a brick and mortar store. And 60 days later, I opened my online store called A Sprinkle of Hearts. And when I was trying to come up with the name,

Amy Boyle (amyboylephoto) (20:01.836)
You you have to look and see what other names are out there. So all like the clever hearts names, they were of course all taken and I settled on countless hearts and I'm laying in bed and you know, these thoughts just come to you, right? You just don't know where. And I realized what's the other, what are other things that I love? And I wasn't consciously thinking about this. I think maybe I wanted this.

I love ice cream and I love ice cream with rainbow sprinkles. And a sprinkle of hearts just popped into my head and thank goodness it wasn't taken. And that's how I named the store. you know, kind of still carrying that thought, my memoir is just an inspirational story. There's no how -to or any commentary at the end of each chapter. And

I had to make a conscious decision when writing which way did I want to go? And that's what I chose. But afterwards I got some comments and understandably, well, you know, I want some concrete steps to take. And you know, they're not steps, they're sprinkles. And that's what my second book coming out in November is called The Sprinkle Effect. It's that idea

whatever we put out, no one's absorbing all of us at once. It is, it's totally a sprinkle and it's such a beautiful visual. And I love it. I can't wait to see it when it comes out. That sounds fantastic. Thank you. Yeah, I just can't wait. Of course the cover's done, but I just want to hold the cover, right? I want to have it in my hands and be able to show people, how cute this is. Because it makes me happy. That's the thing, you know?

All this stuff, feel like part of my personality is like that child. get so happy about things that I guess I could say are ridiculous, but to me they're not ridiculous and everybody has their own thing that lights them up. And for me it's hearts and sprinkles and Mickey Mouse. What can I say? But whatever that is for you, like everybody has something, right? That just brings them that kind of joy.

Amy Boyle (amyboylephoto) (22:27.598)
And I just want to give that to other people. And we should be doing as much of that as we can. Cause like you said, we all have these unique things to us, but just having that, for me it's photography, right? And when I'm out in a professional shoot, it gets kind of contagious. Cause I get so hyper geeked out about whether the lights coming or the, what we, what expression we just captured, we got those endorphins going where

We're happy, we're lit up, we're thinking on a different level and now we're taking that with us to whoever is the beneficiary of being on the reverse of our next conversation. So I say more sprinkles, absolutely. The more the better. Well, let's get into, before we wrap up, I'd love to hear more about your podcasting journey, what it's been like to talk to all these amazing people.

And your just major thoughts and takeaways on what it's like to add that to your, your work and your arsenal of sharing. I really resisted the whole podcast thing. And I don't know why. think it was just another thing that I was fearful of. What if I mess up? What if I don't know what to say? What if, you know, it was all of those fears and those limiting beliefs, you know, that we all have, but these were mine. And.

Finally, I just, you know, really was bullied into it by my business coach and I said, okay, I'll try. And, you know, what I realized was it's such a, again, I always go back to what do I like? And podcasts for me have changed my life. Every thing that I've done, every step along the

I can trace it back to hearing it on a podcast. And I didn't even listen to podcasts until I don't even know how, not, mean, people were listening to podcasts and I still didn't even know how to access one. So it's not like I've been listening from the beginning. And so I think that when I realized, you know, really reflecting how important they are. And, and one of the things that I initially said to my friend

Amy Boyle (amyboylephoto) (24:52.758)
was a big listener. Who are these people that you're listening to? Are they famous people? And she said, no. I'm like, so you're listening to nobodies. And she said, well, no, I'm listening to real people telling me real things. I realized that since they were so instrumental and have been and continue to be in my journey, I want to be giving

same thing to other people. So I started, it's been over a year. I started in May 1st, 2023. And yes, the people that I have met by far, that has been the best, the best part of it because

I have met so many wonderful people like yourself doing such great things in the world that I never would have gotten to meet. it just, gosh, don't you leave feeling like so pumped up and so energized. It's amazing. Like you said, you're spreading that joy to someone else. They're giving it to you and then you're taking it with you to the rest of your day. it's amazing.

The challenge, is, I do find it challenging. I'm hard on myself. question, you know, am I asking the right questions? Is the conversation interesting? You know, that kind of stuff. But again, I think to myself and I listen to other people and they say, yeah, this is my 853rd episode. Go back and listen to episode number one. And you got to start somewhere.

And so you and I have both started and I know that I will not stop. I will not stop. It's just such an incredible platform to be with so many people. And it's such a, like you said, such an intimate experience. mean, our headphones are on or AirPods are in or whatever. These people are coming with us while we're doing chores or going for a walk or, you know, even at the store or whatever. And

Amy Boyle (amyboylephoto) (27:10.934)
So it's a really powerful way to be with people and also find the community from like the interview side. I mean, it sounds like you're endlessly curious. I'm an endlessly curious person. you're like, I want to know more. Tell me how did you do that? What was it like when you felt X, Y, Z, you know, each one is better than the last because you're learning things about yourself too. And the, in this journey.

Absolutely. I want to ask too, when I was on your website, I loved watching your video with Kelly Clarkson. It was just so, it was just, she just seems like a warm person. What was that like and how did that affect anything that's going on for you? So that was surreal. And I knew, it, I got the opportunity kind of through a network connection and I, I knew it might be a possibility and

Then when I found out it was going to happen, I was given less than 48 hours notice. And my interview was over Zoom. It wasn't in person. I tried to tell the producer, you know, I'm right over the river in New Jersey. I could easily get to the studio. And he just laughed at me and said, no, we don't have any room for that. Just this. Okay. Just thought I'd put it out there. So it

surreal sitting in my house and they bring you in to the show. So the segment is the last segment, but I'm watching the show taping on my computer. And, you know, and then the producer's whispering, okay, you're the next segment after, you know, and your insides start to like, my goodness, it's not like a podcast. She asked me the first question or she made a comment and she cursed.

And she said, yes, Debbie, I do curse, you know? And obviously we knew that they were cutting that out. And I thought to myself, am I allowed to curse back at her now? Like, so I didn't know what to do. So I just kind of gave her a thumbs up, like, it's cool, Kelly. So she and I didn't have any like, you know, pre -chatter or anything. But I think to me,

Amy Boyle (amyboylephoto) (29:30.922)
she was very genuine and especially just adding that part, you know, when she said a few things to me that didn't make it on the show. I was petrified, especially because they really stressed that you have to give succinct answers and that's not my forte.

But it was an amazing experience. think I wanted to keep the little NBC logo on my screen after I got off. I'm like, okay, how can that like burn that in here so I can remind myself that, you know, I was actually on this show. And the impact was that the sale of my book increased dramatically.

for 30 to 60 days as well as new followers and all of that. So it was special. I feel like wheels turning and we definitely need to talk more frequently because we're going to have to wrap up sooner than later. But I would love it if you would give the audience your most thoughtful advice about facing the fear, facing fears and making change, whether it's, think you said

not capital T trauma, but like, how do we make sure we put ourselves first? Well, so the first thing that came to mind was what I was telling myself this morning, actually, when I was journaling over something.

I felt like I was thinking about that I'm not really making a lot of progress in this area. And it's hard and it wasn't podcasting, but maybe I should just quit. And it's so easy to quit, right? Quitting is easy. But what happens when we

Amy Boyle (amyboylephoto) (31:21.026)
Then whatever dream we had is never going to happen. Isn't it better to always, you know, just keep moving forward, even if you're not getting there as fast as you want. And I think that that's what it really is in my case. And I think in many cases, I want immediate gratification, right? Don't we all? Wouldn't that be so nice? But it doesn't work like that. And I would say that if you

are going to stay where you are in your comfortable little bubble. Just know that's what you're going to get out of life. And is that all there is? And I think that that's what scared me, that I was going to get to the end of my life and look back and say, man, maybe I could have done that. I never even tried. And I don't know about you. I don't want

I want to know I tried and if I tried and I failed, am I going to be looking back with regret? No way. I'm going to be proud of myself that at least I tried. So it's just that perspective that has helped me because as we know, the years fly by and you

Just like our parents and grandparents used to say, right, as you get older, they go by faster. And it's true. So it'll be here before you know it. So maybe that'll be some motivation for you out there.

Amy Boyle (amyboylephoto) (33:01.782)
And what is fail even if you tried? It's not really a true failure in my opinion. It's... Let me just say I heard something somewhere. Fail stands for first attempt in learning.

And it's true, right? I just wrote in one of my chapters or something, Thomas Edison, 10 ,000 attempts, 10 ,000 failed attempts at the light bulb. And, you know, he looked at it as, okay, that taught me what not to do. So it teaches us something, right? It always does give us something. So you're right. There was no such thing as failure as we think of it. Well, I can't thank you enough for being on the show today.

All your places for people to find you will be linked to the show notes. But for those who are audio files, can you please say where they can find you as well? Sure. Thank you, Amy. And it's been wonderful to be here. So my website's the best place. Everything is there. My website is debbyrweiss .com. You've got to put in the R, otherwise you wind

in California. Well, again, I can't thank you enough and keep sprinkling away because I love the message and what you're putting out in the world and I want more people to hear about you, know about you and darn it, drop a DM, get in touch with us. Thanks, Amy. Thank you for joining us on this episode of Speaking of Phenomenal. Be sure to subscribe, rate, review, and even share the podcast as well as stay tuned for more inspiring conversations.

Remember, each and every one of you is capable of extraordinary things. Until next time, take care and remember, you are phenomenal.