Maybe I Can® with Debbie Weiss

Ep. 139: Designing A Life You Love... Beyond The 9-5

• Debbie Weiss • Episode 139

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In this episode of Maybe I Can, I’m diving into something close to my heart: how to design a life you truly love.

I used to believe adulthood meant responsibilities, 9–5 jobs, and chasing the next salary milestone. But I’ve learned that’s just one lens, and not the only path. Whether you’re a recent grad, a parent watching your kids find their way, or someone asking “what’s next?”, this conversation is about choice, freedom, and possibility.

I share:

  • How my son’s graduation sparked a new perspective on work and success
  • Why chasing money alone won’t bring fulfillment
  • A powerful Japanese framework called Ikigai that can help you find your sweet spot in life
  • Why it’s never too late to reinvent yourself

If you’ve ever felt stuck in “shoulds” or pressured to follow the traditional path, this episode is for you.

👉 Listen in, and let’s reimagine what life and work can look like when we lead with joy and purpose.

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Speaker 1:

Hello and welcome back to the Maybe I Can podcast. I'm your host, debbie Weiss, and thank you so much for joining me today. You know, many podcast hosts are a little more professional, I guess I would say. You know they have a thought-out plan, they record their episodes in advance, they have guests, they have a nice studio they show up with if you're watching on YouTube with, you know, done up with their makeup and their hair, not like I'm looking like today and I realized, you know, and now it's been a little over two years since I've been doing this podcast and I kind of now just give myself grace.

Speaker 1:

That is not for me. I do this podcast so that I can just share what's on my mind and my heart in the moment, and I literally just record a couple of days beforehand, typically just so that it's whatever I feel like talking about this week. And so this week just came to me, actually yesterday. I want to talk about designing a life you love, and the reason that this came up is because I was scrolling through some social media Instagram or Facebook, most likely and I saw posts about kids going back to college. One of my team members just moved their daughter back into her school this past weekend and I was feeling a little kind of melancholy over the fact that my youngest Ben we're done with that. He graduated in May it's hard to believe that it's already months later and he had such a wonderful college experience and I was excited that he was graduating, but then also sad. And over the summer, and let me just say he currently does not yet have a job. He's working on that and well, I'll go back to what I was just thinking. I was going to say his idea of what a job should be and mine are a little bit different and I'll explain that in a little while.

Speaker 1:

At first I thought to myself how sad, how sad that that part of his life is over, that wonderful college experience is over. And now what's he? Stepping into Adulthood? And the first thing that crossed my mind is and the first thing that crossed my mind is oh, the responsibilities, the money, the nine to fives, the worries, the whole thing. As a kid, you can't wait to be an adult and live on your own and not have to listen to anybody else's rules. And then, when you get there, you think, oh man, I didn't realize, this is what it is. And I was thinking that way, because that's what was ingrained in my mind and that's really my experience, my memory. When I look back, that is the lens in which I look. And then I had to stop myself and say, hey, wait a second, that's the old Debbie talking. That's the old Debbie's mindset. What about the fact that he has his whole life in front of him to map it out and to dream and do whatever it is that he wants to do? But it's just.

Speaker 1:

I don't think how our culture works. You know, it's all about success, it's all about money. I can see as his friends are getting jobs and looking for jobs. It's like well, how much does that pay? How much does that pay? And even my son said well, mom, that only pays, blah, blah, blah, whatever the amount was. And I said to him who cares, ben? Who cares how much it pays? You want to try and do something that you love. You are looking to get a job that sounds interesting to you and get some experience and find out, hey, is this something that lights me up? What is it about this job I don't like and what is it that I do like? And then move on from there. You're just starting out, money will come. It's not all about the money and I know that I felt that way, oh my goodness.

Speaker 1:

I remember when I graduated from college and I was an accountant and I got a job in a small accounting firm and I don't know why I remember this exact amount, but I made $16,100 a year and my cousin, who had not gone to college and had been working I think three years more than I had, was making $30,000. And I thought that was amazing. If only I was making $30,000, then I could fill in the blank. I think at the time it was probably buy a car, live know, and I always I think I always was chasing that number and doing that whole comparison thing instead of tapping into what I love to do. And I did enjoy things about my accounting career and it was great because I learned what I liked and what I didn't like, and I did it for 10 years. And then I opened up my insurance agency, which was something that I never you know, I don't know who dreams of being an insurance agent Maybe there's people out there, but not me but there are things about it.

Speaker 1:

Now it's been over 30 years doing that and there's things about it I love, and there's things about it that I don't, and I think that's why, when I turned 50, I started to look and say what can I do? That really lights me up, that I'm meant for, that doesn't feel like work, that feels exciting, something that I want to be doing all the time, something that I don't pay attention to. The clock, right, I'm not always looking, thinking, oh gosh, it's only 11 in the morning. Only you know another hour till lunch, or it's three o'clock. This day is dragging. You know what I'm talking about. You know that feeling. And look, we all have days like that, regardless of if we do something for a living that we love or we don't.

Speaker 1:

But I really saw the difference once I started stepping into this new vision and this new dream, and it was. It's really what has inspired me to keep going. It's really what has inspired me to keep going, even when I've changed paths and directions. It has always been exciting and I, for the most part, enjoyed the work. Look, with any job, there's things you don't want to do. That's just a part of life. But you know, if there's 20% of what you want to do and 80% of what you love to do, that's not bad, based on what the flip side could be 20% of what you love and 80% of what you don't.

Speaker 1:

I've talked to several other moms that have kids similar age and a couple of them are disappointed that their I'm going to say sons, because I've spoken to boy moms haven't taken that traditional nine to five path. Nowadays it's so much easier to create the life you love and I think these parents who are of similar age to me they're in that mindset that you get a job with a big company and you put in your time and you do the nine to five and you move up the ranks and you get retirement benefits and you get vested and all the things that it used to be. But the fact is those days are gone. In those early days there was security in working for big companies for your entire career, and I know a few people who've done that and I also know someone who, after 30 years, got laid off right. There is no security in that anymore. It doesn't work the same way. Times are changing as we know. They're changing very quickly with gosh, you know, with AI, we don't know where things are going and I feel that why shouldn't these kids try something they're excited about, even if it's not that nine-to-five job.

Speaker 1:

So let me give you a couple of examples. One of my older son's friends. He graduated from a very good public university with a degree in computer science about a year ago year and a half ago maybe and he has not been working that typical nine to five. Instead, he actually has a Pokemon card business. I know it sounds crazy. It sounded ridiculous to me. I could not believe how people, how much money some of these cards are worth.

Speaker 1:

And this kid has done his homework. This is his business. It is not a hobby. And he is learning. He's getting on-the-job training about so many different facets of the business. But yet his parents they're not happy about it. He doesn't have that security. They're not seeing that regular paycheck come in every week and get deposited into his account. They don't understand because they have no frame of reference. Because they worked for big companies and they did well and they moved up and they got their retirement benefits and you know all the things and that's not the path that he's taking. And you know all the things and that's not the path that he's taking.

Speaker 1:

But yet my feeling is, if not now, when it is harder to do something like that as we get older and we have responsibilities although it's still possible, because I'm living proof of that but this is the time right, when you're young, to explore all these different options. How great is it to do something that lights you up? This kid never stops talking about Pokemon and what he's learned and how much he paid for this and how much it's gone up in value. And this show that he's attending and this online sale, all the things he's doing it, and he loves it. He absolutely loves it. Isn't that what we all want? I think that's a rhetorical question, because who wouldn't want to live a life by design that you love, where you're able to support yourself, that you love, where you're able to support yourself? If we keep thinking and these younger kids keep thinking, that this is what they have to do?

Speaker 1:

When I was on vacation a few weeks ago with my family and my son, ben's girlfriend came with us and at dinner one night we were talking I don't even know how the career thing came up or in what context and both my son and his girlfriend said well, I'm gonna do this for now, but I'm sure my second career will be this. And his girlfriend said eventually I wanna do something like you do, where I'm not tied to that nine to fives. And I'm thinking to myself why do they think that has to be something down the road? They're both very practical people and they're both very responsible people and they're not like my other son's friend who has that entrepreneurial mindset which is fine. Not everybody has it but they have other ideas in mind what they want to do next. My son says well, I think eventually I probably will be a teacher, but for now I want to try this corporate thing, and that's okay, and I think that he should whatever. He wants to try this corporate thing, and that's okay, and I think that he should whatever he wants to try. I think he should because he shouldn't look back. If he truly is something he wants to try to see, if he likes it, to see if he's successful, then he should. That's his desire. The other kid's desire is to build this Pokemon business and I think that we should all be able to create a life that we love.

Speaker 1:

Last night, actually on I think it was Netflix, I watched this movie and I'm not sure of the name, but I think it was my Oxford year and it wasn't really the movie that I thought it was going to be it had a little bit of a heavy side to it, but a great message and knew that she was going to go to a good school a good college, I think in the movie. She went to Cornell and then she was going to spend a year in Oxford getting her master's degree and then she was going to work for Goldman Sachs. She knew that because she knew, oh, goldman Sachs, that's the pinnacle of success in the financial world. And that's what she did. At 11 years old, she set her mind to achieve that goal, that this was her idea of success, and she did it. She did all the things. She got a job at Goldman Sachs and she was able to defer it a year so that she could go over to England attend Oxford.

Speaker 1:

I forget what kind of poetry it was, but some kind of poetry. And, of course, through the circumstances of the movie, which I'm not going to share with you in case you want to watch it she realizes that that's not the end. All be all right. A life working for Goldman Sachs even though to some that might be the pinnacle of success that's not what lit her up and in the end, she changed paths. What I want Maybe this isn't what lights me up so we've got to shift our mindset to think that working that nine to five, or work in general, equals dread, equals, something we don't want to do. I remember at times having that Sunday night sickness, feeling like oh my gosh, I can't believe it's Monday already. Look, I still would like every day to be a weekend, kind of, but I think if that were the case, I know that sometimes when I'm on vacation, I'm like ready to get back to it. Right, I'm ready to jump back in to what I do separate from insurance, but I still am okay with that. And you know see where I'm going to go next. You know see where I'm going to go next. Let me share with you.

Speaker 1:

There is a Japanese framework and I hope I'm going to pronounce it correctly called Ikigai, and it asks you to explore or answer four different questions what do I love, what am I good at, what can I be paid for and what does the world need? And where these overlap, that's when you land on your ikigai, which is your sweet spot, your reason for being, and I just love this. You make those lists, or even like in a Venn diagram, right when you see the overlap of four circles and in that overlap, what do I love? What am I good at? What can I be paid for and what does the world need? And just now I hadn't really thought about it. What do I love? I love helping people. I hadn't really thought about it. What do I love? I love helping people. I love teaching. I love teaching. What am I good at? I think I'm good at those two things I really do. What can I be paid for? Sure, I can be paid for that. And is it something that the world needs? I'd say so.

Speaker 1:

The world always needs someone who can talk to you and give you an idea that expands your mind, changes your thoughts, that opens you up to a new world of possibilities. And that's my goal, right? I'm here to tell you that, regardless of where you are right now, regardless of how you think, it's not possible, it's not possible for me to figure these things out and then do something about it. But that's why I'm here. This is my sweet spot. I'm here to show you by example that is not the case.

Speaker 1:

There is always something you can do to move yourself in that direction of your ikigai. We have to redefine that. Adulthood does not have to be a trap. It doesn't have to be a trap. It's only a trap if you let it become a trap. I hate to say it, but it's true. We've got to look in the mirror. Who did this? Who created this life? We did. Yeah, there are outside circumstances Sure, there always are. This is life. But then we decide how we respond to those things. And so I don't care how old you are, I don't care if you're 20 or you're 70. There is always time. As long as you're breathing, you can do something to move yourself in the direction of a life that you desire.

Speaker 1:

I'll tell you, I was on a. This is a couple of years ago. I'll tell you, I was on a. This is a couple of years ago when I first wrote my memoir and I was on with some group. There was like 15 people, and most of the people were in their 70s and 80s, and they had written a book for the first time At 80-something years old. They were first-time authors. They didn't say I'm too old. They didn't say I can't do this, I have nothing to share. Nope, they believed and they did it, and so can you?

Speaker 1:

So what's your ikigai? I challenge you to answer those questions, see where they overlap and then, when you find out, what are you going to do about it? Again, what do I do? Oh no. What do I love? What am I good at? What can I be paid for? And what does the world need? Life after college, life after any big transition? Even no transition, it could be age, the transition of getting older. It doesn't mean the end of freedom. It's always the beginning of choice. We have the choice to paint our lives and sprinkle them with loads of color. That's what I got for you today. Go out there and design the life you love. See you all next week.

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Debbie Weiss

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