What Happens When You Finally Ask “What Do I Actually Want?”

You’re Not Too Old to Start Over: The 62-Year-Old “Numbers Girl” Who Became a Bestselling Author

When everyone around you is planning retirement and you’re just figuring out who you really are

Debbie’s story is a powerful example of: “What happens when you finally stop living the life you thought you were supposed to live and start exploring what actually lights you up”.

At 50, Debbie Weiss realized she’d spent half a century living for everyone else and had no idea who she actually was. At 62, while her friends talk retirement, she’s a bestselling author who’s been featured on The Kelly Clarkson Show with 3.7 million TikTok views. This is what happens when you finally give yourself permission to try things and follow what lights you up even when you’re “supposed to” be winding down.

Today I’m speaking with Debbie Weiss. Debbie is a bestselling author and speaker and she’s written two books. One is called “On Second Thought…Maybe I Can” and the other one’s called “The Sprinkle Effect: A Guide to Creating a More Colorful and Fulfilling Life.”

I just talked to Debbie and her story was so inspiring. She’s about to turn 62 and told me she feels like she’s literally just starting her life. All her friends are talking about retirement and she’s over here building a whole new career and a whole new chapter for herself.

For years, Debbie was the person everyone leaned on. She worked as an accountant for a long time and then ran an insurance agency with her husband for 30 years. So that’s the classic responsible adult story.

But she was miserable inside and didn’t even realize it.

And then something changed. She started writing and discovered she’s actually super creative. And now she’s got books out there. She went viral on TikTok go check out her account, it’s really fun. I love a good TikTok. And she even got featured on The Kelly Clarkson Show.

At 62, it’s only just starting.

What really stuck with me was how she talked about finally figuring out who she actually is versus who everyone expected her to be. Like so many of us are out here just playing these roles the responsible one, the caregiver, the mom.

And internally, we’ve completely lost ourselves.

She’s had her new book come out and she’s helping people stop being victims of their own circumstances. And honestly, if you’ve ever felt trapped in your own life and you feel a little bit lost at the moment and maybe thinking it was too late to change things, you really need to hear her story and what she has to share. It’s very inspiring.

Debbie’s Career Journey as a Mom

MELLY: Welcome, Debbie. Welcome to Mama What’s Next. I’m so happy you’re here today. Thank you so much for joining us.

DEBBIE: Oh, thank you so much for having me. I’m very excited and happy to meet you.

MELLY: Yes, me too, me too. We’ve just had a quick brief conversation beforehand about the joys of podcasting and how it’s so amazing that we get to connect in this special way. We don’t know each other, we’ve never met each other, we live completely different lives and yet there’s this amazing social media and online world that makes us connect in this kind of way. And usually the conversations I get to have, and I’m so grateful for this, they are quite deep and meaningful. And we talk about meaningful work and creating careers and a life and a work life that really makes the most of life and every, all the time that we have. And that’s why I invited you today, because you’ve got an amazing story to tell. So I’d love to just start with you introducing yourself and telling us where you live, what you do, how old you are—all these things.

DEBBIE: Thank you. So I am living in New Jersey. I’m originally from Long Island. And I am about to be 62 years old and feel like I’m literally just starting my life. And so many of my friends are talking about retirement and winding down and all the things. And I’m thinking, no way. I am just stepping into and trying to figure out what I’m passionate about.

I’ll give you my brief career journey. So I went to college to be a CPA. I became a CPA. I worked as an accountant for 10 years in a small accounting firm. And there were parts of it that I enjoyed. There were parts that I definitely didn’t. Taxes—seven days a week, nights until 10 p.m. January through April it got to wear on me year after year. And inside, I was always yearning for something different, but I didn’t know what that was. And so I was dabbling, like, guessing maybe it’s this, maybe it’s that, but I never had the courage to step out of my comfort zone and leave my accounting job.

And then a very close friend of mine, she worked for an insurance company, and there was an opportunity for me and my husband. I was newly married at that point to move from Long Island. And it did turn out, now it’s 30 years later. So clearly it was the right thing to do. It really allowed my husband and I to be there for our boys. We wound up being able to job share. So I would stay home Monday, Wednesday, Friday. He would go to work Tuesday, Thursday, that kind of thing. So it was nice because they got to be, quality time with their dad, which so many kids don’t get, and with me. And we were still able to run the business and maintain our earnings and all of that.

The Hidden Cost of “Doing the Right Thing”

Notice how Debbie describes her life as doing what was “right” the stable career, the family business, being there for everyone. On paper, it looks perfect. But here’s what most people miss: you can be doing everything “right” and still be completely miserable. Success isn’t just about checking boxes or meeting external expectations. True fulfillment comes when your outer life aligns with your inner truth. If you’re exhausted despite “having it all,” that’s your signal that something needs to change.

DEBBIE: And my life was pretty difficult. I had a lot of personal challenges going on. I had been a caregiver to my father. In the end, it wound up being for 30 years. Our oldest son was diagnosed on the autism spectrum when he was two. And I didn’t know it then, but my husband was also suffering from different forms of mental illness. And in the end, my husband wound up walking out of our office one day—this is well into it, 20-something years into it—and saying, I can’t come back because he had shut down.

During a few years prior, when I turned 50, I was in not a great mindset in my life. And my friends insisted that we go away for the weekend to celebrate my 50th birthday. And I was like, I can’t leave these people. My family, I’m like the—I’m everything. I’m the manager. I’m the director. I have to point and tell them where to go. I have to take them there. My husband, too. It’s like I just had to turn them around, shove them in the right direction. What is going to happen? I’m going to need so much prep just to go away for the weekend and I’ll be worried the whole time, blah, blah, blah, blah, blah.

Luckily, I had great friends who said, it will be fine.

And from the minute that we met at the airport, the laughter started. I practically forgot my family members’ names, and we had the most incredible weekend.

But in that weekend, I realized that I, as a woman, as a person, was lost and in a bad place.

The Weekend Away

This is the moment most of us avoid at all costs, the moment we admit we’re lost. Debbie thought she was indispensable. She thought leaving for one weekend would be catastrophic. The truth? Everyone was fine without her. And that realization, while initially painful, was her liberation. If you’re constantly playing the martyr, ask yourself: What am I getting out of being “needed” all the time? Because often, we use other people’s dependence on us as an excuse not to face our own unfulfilled dreams.

DEBBIE: And how had 50 years flown by? And I don’t want to say, what do I have to show for it? But I watched my dad, who at that point had passed away a year before, and he had so many regrets. And my mom was always talking about the past and mistakes that she made that she regretted.

And I thought, I don’t want to be that person. I don’t want to be that person at the end of my life looking back saying, man, it flew by so quickly and I didn’t do what I was here to do.

But the thing was, I didn’t know what that was. I didn’t say I always wanted to be a writer, an actor, a doctor. I didn’t have that.

And so I came home and basically I’ve been in search and gone on many different exciting paths over the last dozen years since I turned 50. And it has been an amazing journey. And I don’t think that that journey will ever end because it’s always evolving. And over the past 12 years, it certainly has evolved.

MELLY: I think it’s so beautiful. And it’s been very touching as well because I think so many people, women especially, they go through this in life. And I read on your website as well and your background that you also took care of your dad for a while. So I don’t think it’s an easy journey to have that and then your husband in this kind of state. I know what it’s like to have someone with depression next to you and it’s not an easy journey. It’s challenging. And I think it’s really difficult to then not forget about yourself. And there’s so many challenges and also that heaviness kind of pulls you into another world as well. So you’ve got to, while being there for everyone in your family, you had to almost paddle for air as well and make sure that you actually stay healthy and positive, I think.

You talked about how you live your life now and that these last 10, 12 years have been so interesting and so inspiring. What do you think the reason is we’re here? What do you think we’re here to do?

DEBBIE: So I think that we’re all here I feel at this point, and I wonder, actually, does it have to do with age and wisdom and experience? Because I want to help those who are where I was a dozen years ago.

And it’s interesting because my youngest son just graduated from college, and I said, well, what do you want to do? And he said, I don’t know. I just want to help people.

And I do feel that that’s an innate thing that we all have. You can look at most jobs. And even if they don’t, I’m an insurance agent, it doesn’t feel like I’m helping people, but I am helping people. And I do get to see that every day. And that is rewarding. It’s just rewarding in a different way than talking to you and your audience.

So I think so many of us are here, really, that that’s the main goal is to help each other.

MELLY: Yes, to support each other. I think so, to support each other and inspire each other. And also, I think it’s just a learning and growing journey, right? Like to experience ourselves. Like, it’s like so many people, and I don’t know if you’ve experienced that, when you think back, obviously when you said you weren’t so excited about the insurance career journey, right? I was thinking, yes, and we always think there’s this end point, this final destination somewhere that we need to get to, to finally be happy. And just from listening to you now and also reflecting on my career journey over the last few years, I feel it’s just so much more like the experience of trying new things and trying out yourself and experiencing yourself in a new way. That’s how you feel to me now.

DEBBIE: Yes, that is exactly it, exactly it. It’s so funny, like I said, I’m still not, I don’t think there will be an end. And now what’s very interesting to me is that if someone asked me, Are you creative? I would tell them, I do not have a creative bone in my body. I am a numbers girl. I love numbers. Accountant, insurance is also numbers. Like there is, don’t ask me to draw something. Don’t ask me to write anything.

And what I found that really, really amazes me on this journey, once I started opening up to different possibilities and stop saying, oh, I’m not this and I’m not that, amazing things started to happen. And now every second, I’m like, oh, I want to do this. Oh, I want to create this. Oh, I have, like these ideas just keep coming. And I still can’t draw, but that’s not the only form of creativity.

The Stories We Tell Ourselves

“I’m not creative.” “I’m just a numbers person.” “That’s not who I am.” These aren’t truths, they’re stories we’ve been telling ourselves for so long we’ve started to believe them. Debbie spent 50 years convinced she wasn’t creative, and now she can’t stop creating. What story are you telling yourself about who you are or aren’t? And more importantly – is it actually true, or is it just comfortable? The most dangerous stories are the ones we use to keep ourselves small and safe.

DEBBIE: And it really, it feels like I just allowed a different side of me to come through that I honestly would never have thought – I had no idea it existed. And that is very exciting. And I almost have to stop myself because I’m so anxious to go to the next thing and I want to create this and I want to create that, and oh, I have this great idea. And I kind of have to reel it all in and say, okay, one thing at a time, and stick with it because I’m just so excited to try all these things. Like there’s not enough time in the day, in the week, in the month.

MELLY: Yes. I know exactly what you mean. It’s like, for me, it’s the podcast. And I’ve always had these kinds of projects. Sometimes it’s been a web project that I’ve done, like a big lifestyle blog that started like a passion project and eventually even made money for me. But even with the podcast, I’ve had someone close to me in my family when I, before I started it said to me, don’t take this the wrong way. Like who are you? Who’s going to listen to this? Like you’re not somebody.

And it’s hard.

The Critics Will Always Have Opinions

Here’s the truth nobody tells you: the people closest to you will often be your biggest critics when you decide to change. Not because they’re bad people, but because your growth threatens their worldview. If you can reinvent yourself, what does that say about their choices? The question isn’t “who am I to do this?” the question is “who am I NOT to?” Your voice matters. Your story matters. And the right people – your people – are waiting to hear it.

MELLY: I cannot imagine you being the accountant looking like this and talking like this. Like how did you come up with that kind of work and how you positioned yourself and how did that happen?

DEBBIE: So I think I would say I wasn’t that typical accountant that you think of. I had to grow up quickly. And so I’ve been that person who always does the right thing, who always, whatever situation I’m thrown into, I handle it. I’ve learned about so many things when different struggles have come my way. I became an expert in autism. I became an expert in Medicare, in the United States when my father first had the stroke and I was in my 20s, nobody knew about that when you’re in your 20s. And then mental illness and then so many different things.

So I had, that was me on the outside, but I’ve always had like this childlike excitement and it’s another part of my personality that the people close to me always knew. It’s nothing new. It’s who I always was. I always loved pink and hearts and I’m a big Mickey Mouse fan and I love my birthday and you could give me a thousand balloons. The girls at my office have done that, they’ve blown up balloons for my birthday and laid them all over the floor when I walked in. Like, so it’s always been me. It’s not, it’s just that I’ve allowed that to come out now.

It would make me happy if I put on a pink dress and I sprinkled people with joy and happiness and all the things. And everybody just shakes their head. But it’s who I am. It is who I am. And I also have that other side. I’m a good businesswoman. I can say I’m a good leader. And that’s part of my personality too. And why can’t they both come out?

MELLY: Yes, I love that so much, Debbie. I love it so much. And this is the struggle so many face, I think, to really be ourselves, right? Like we hide so much that kind of real truth, how we are. And I loved so much just listening to you, how you said, this is just who I am, right? And what would you say to somebody that struggles with that? Because obviously sometimes people have like little quirks and they’re different and they express themselves differently. What would you say to them? Like how would you respond to them if they struggle with just fully being themselves?

DEBBIE: I understand because it is hard. The woman who I took a course, there was like five of us who’d never written a book, blah, blah, blah. And so we would meet every week and she helped us along the way. And she said, would you be happy if one person, one person read your book and it had an impact?

And of course the answer was yes.

And it’s the same thing with your podcast. Who cares if millions of people aren’t listening to us? That’s not the goal, right? Because I remember thinking just the same thing that she said to you when I was writing the book, I’m not a celebrity. Who cares about my story? And luckily, I haven’t had some horrific, horrible thing happen to me that pulls people in. But then I realized, who do I want to listen to? Who can I relate to? I can’t relate to a celebrity. And I can’t relate to someone who, God forbid, was kidnapped for 30 years. I can’t.

I can relate to a regular woman who has struggles and what they did about it.

The Power of Ordinary Stories

You don’t need a dramatic backstory to have something worth sharing. In fact, most people can’t relate to extreme stories. What they need is someone who’s lived a life like theirs, messy, complicated, full of ordinary struggles, and found a way through. Your “ordinary” story is someone else’s permission slip to change their life. Don’t wait for your story to be “impressive enough.” Share it now, because the person who needs to hear it is already looking for you.

DEBBIE: And so I think the message is, if you don’t let your true self come through, just realize that you’re not reaching and helping the people that you were meant to help.

And when you suppress yourself, I mean, you are not living a life for you. And when you do suppress yourself, you’re suffering, right? You’re keeping it inside. You’re trying to hide. You don’t want anyone to know that side because what will people think of you? And especially nowadays with social media, it was different for the majority of my life. Everything is on display and it’s hard, but we have to shut out that noise and just be true to ourselves.

MELLY: Yes, yes. And Debbie, especially coming from you now this message because we, and I include myself here as well, I’m not quite at your age yet but I still didn’t grow up in the social media, I started with the Facebook times and stuff but I like, it’s the new generation now. I mean for them talking into a screen doing video it’s like drinking a cup of coffee in the morning, right?

DEBBIE: Yeah.

MELLY: For me that was not normal and I feel our generation still, like 50s and 40s and 60s, yeah, it’s not so easy for us. And I hear it always when in coaching sessions people are very hesitant to put themselves out there because they’re scared of the rejection, they’re scared of what people could think of them, right? What do you tell them? Especially women, because I think it needs more women your age also in their 50s that step into that because they are being called to work with their kind of people. We don’t want to listen to 20-year-olds.

DEBBIE: Not at all. So let me just, I’ll answer that by telling you what happened to me. So when I first started and I had to make a video I was crazed. Like where do I go? What do I say? What do I wear? How’s my hair? I made sure I looked good. I thought, all right, I’m going to, I have a minute or whatever it was. And I put it on index cards and I was trying not to look at the cards. And I re-recorded myself literally probably like 50 times.

And after doing this like three times, I thought, I can’t do this. This is so stressful. It’s a lot of work. I don’t look good all the time. I don’t. I mean, none of us do. And to have to worry about that.

And one day, I was walking my dog, as I always do, and something popped into my head that I just felt like, oh, I have to remember. I want to say this. And I thought, I’m just going to turn on my phone as I’m walking, first thing in the morning, after exercising with no makeup and my hair up in a ponytail like it is now. And I’m just going to say it.

And I did. And I put it out there. And people listened. And nobody said, and I don’t care if they were thinking, look at that woman, how could she go on social media looking like such crap? But they didn’t pay attention to that. And if they did, they’re not my people, if they’re that shallow, right?

Perfection Is the Enemy of Connection

On social media: people don’t connect with perfection. They connect with authenticity. When Debbie stopped trying to look perfect and just showed up as herself, messy hair, no makeup, raw emotion, that’s when people really listened. Your “flaws” aren’t what’s holding you back. Your perfectionism is. The content you’re too scared to post because it’s “not good enough”? That’s probably the content that will resonate most.

DEBBIE: And that moment realizing I can put that out there and people like it just as much, and I found out even more so, that gave me the permission. And oh my goodness, I’ve really gone down a rabbit hole. Sometimes I can’t believe what I put out there, how crazy my hair looks or whatever it is. But that’s me.

And I always feel, and I think this is always who I have been, is authentic. And we know that people want that now. And it’s easier for me because that is who I am at the core. I just, I can’t pretend. My mother used to say, Debbie, you don’t need to tell everybody everything. Because I would just, this is who I am and spill my guts.

And I actually had a video go viral on TikTok. It was crazy, crazy exciting. And I was walking and choked up and it was the message that got them. But I think I had 200,000 people hearting it. 3.7 million views. And nobody said, can you believe that woman walked and put herself out there looking like that? They just cared what I said.

MELLY: Yeah. That’s what I love about TikTok. It’s much less polished and more raw and real with people. Like you can just record a message in the moment, as if you were just picking up the phone talking to somebody. And it’s just a lot more real and connecting to people, I think. I love that about TikTok.

DEBBIE: Yes. We don’t need to, yeah, sure, sometimes depending on what you’re doing, you want to look good, obviously, but that shouldn’t stop you. And I think that as far as using social media for business, I have never been good at saying, okay, here’s the message that I want to get across. And this is the way I have to say it. And I want to hit these words. And if you’re looking from a business perspective, it actually is a downside and something I need to work on, because for me, it is just sharing what’s on my mind. Not necessarily a message that might go viral or reach my right audience. I’m just saying what I’m living.

MELLY: Debbie, how did you come to write the first book? Like I’ve got friends left and right going, I’m thinking I could, I wanted to, but I don’t know if I would, and I find it so hard and intimidating. And I’m like, but you’ve got to do it. And they’re like, I don’t know. How did you do it? Why did you do it? How did you overcome the fear? Tell me everything.

DEBBIE: So I’ll go back a little bit. Maybe about four years before I wrote the – first of all, I’ve never wanted to write. Like I said, I’m a numbers girl. I would go to school and take a class in college. And if I found out it had a paper, a big paper due, I would take another class because I didn’t want to write. And I never had a desire to write.

When I was, I was very involved in this organization for years. And I never agreed to be president because the president had to speak. And I was very involved on this journey. I really talked myself into it saying, this is something you’re going to regret because maybe you’ll be a good president. Maybe you’ll make a difference. But because you’re so afraid of speaking, you’re going to allow that to not have you do this?

And so I took the big leap.

When I had to speak, I start talking and I tell a little joke or whatever, and the people laugh. I’m like, okay, that feels pretty good. And then I get to this part where I say a few sentences about something to do with my father. And I had practiced it, obviously, a lot. And I never got emotional. But standing up there in that moment when I said that, and my father had passed away a few years earlier, I got choked up.

Vulnerability Is Your Superpower 

This is where the magic happens – when you stop trying to have it all together and let people see your humanity. Debbie thought getting emotional during her speech was a mistake. But that moment of vulnerability? That’s what connected her to everyone in the room. That’s what changed her life. Your story’s power isn’t in making yourself look good. It’s in being brave enough to be real. The moments you’re most afraid to share are often the ones that will impact people most deeply.

DEBBIE: And it was so powerful in many of their eyes. And after it was over, everyone came up to me, and they wanted to share their story of the same message that my story with my dad told. And they just said such lovely things. And I thought, oh my goodness. This is amazing. I felt so empowered and thought, I think this is what I’m meant to do.

And it changed, literally changed the trajectory of my life. I was not yet at a point thinking that I was going to do any kind of different career. I was just personally developing at that point. Years later, probably about four years later, led me to writing.

MELLY: So that was Debbie and honestly I could have talked to her for hours. There’s something about her energy that just gets you, right?

The thing that really stuck with me though is how she kept saying “I’m not creative” while literally creating all these amazing things. It’s so typical for us women, isn’t it? We have this story in our heads about who we are and then life comes along and shows us we were completely wrong.

Debbie didn’t want to speak in front of people because she was terrified. Luckily, she overcame that fear, got out of her comfort zone, and she did it anyway, and it completely changed her life.

Next time we’re talking about what happens when everything falls apart, her husband’s illness, becoming a widow, and how she somehow managed to write her way through the worst period of her life. So stay tuned for more of those sprinkles because this sprinkle fairy situation is quite special.

I will talk to you soon next Wednesday with another episode. Thank you so much for listening today. Goodbye.

Final Thoughts: What Debbie’s Story Teaches Us

If you’re reading this thinking “it’s too late for me” or “I’m too old to start over” or “I don’t have anything special to offer,” I want you to read Debbie’s story again.

She was 50 when she realized she’d lost herself. She’s 62 now and just getting started. She spent decades convinced she wasn’t creative – and now she can’t stop creating. She was terrified to speak in public, and that one speech changed everything.

Your age isn’t the problem. Your circumstances aren’t the problem. The story you’re telling yourself about who you are and what’s possible, that’s the only thing standing between you and the life you actually want.

So what story are you ready to rewrite?

Read the 2nd Part of our Interview here: Midlife Career Reinvention at 62 with Debbie Weiss

Connect with Debbie Weiss at www.debbierweiss.com and follow her journey on Instagram @debbie.r.weiss and TikTok @debbierweiss

Listen to the full Mama What’s Next podcast episode wherever you get your podcasts.

‘Mama, What’s Next?’ Podcast and community that provides holistic career coaching for mothers.

 

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