Rethinking Retirement Through a Portfolio Life

What if the next chapter of your career is an opportunity to design a life filled with meaning, contribution, and new possibilities?

On this episode of The Get Ready Money Podcast, I spoke with Maria Dastur, Founder of Second Half Community about rethinking retirement and designing a portfolio life that blends purpose, contribution, and financial security.

Key Takeaways: 

🔹 A portfolio life diversifies multiple streams of meaning, purpose, and income.
🔹 Strong networks provide support and opportunity during career transitions.
🔹 New chapters often require learning new skills and perspectives.
🔹 Failure and discomfort often lead to the most meaningful growth.
🔹 Clear non-negotiables help guide career and life decisions.
🔹 Knowing your financial numbers allows you to pivot with confidence.
🔹 Retirement can become a phase of contribution, flexibility, and impact.

🎯 Tony’s Take: A fulfilling life after mid-career comes from clarity, curiosity, and community. When we know our numbers, stay open to learning, and surround ourselves with people who believe in us, we create the freedom to design the next chapter with purpose.

Connect with Maria Dastur, MBA:

• LinkedIn: https://www.linkedin.com/in/mariadastur/
• Second Half Community Website: https://www.secondhalfcommunity.com
• YouTube: https://www.youtube.com/@secondhalfcommunity

Resources mentioned:

• Find Your Passion in Refirement! With Kathleen Rehl on the Get Ready Before Life Happens Podcast (here)
• Redefining Success for Women in Finance: The Power of Your Network with Cameo Roberson & Kari Ellis on the Get Ready Before Life Happens Podcast (here) 

Bio: 

Maria Dastur is an award-winning leader, career coach, and community builder dedicated to helping people break down barriers and thrive in their careers and lives. After more than 20 years in non-profit leadership, she launched the Second Half Community to help individuals realign their careers with who they are now. Maria’s mission is simple: help people create work that fits their life, not the other way around.

☕ Support the Get Ready Movement.

If these conversations help you think differently about money or prepare for life’s what-ifs, your support helps expand financial readiness education and keep this work accessible.

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Transcript

SPEAKER_01 0:16

Welcome to Get Ready Before Life Happens. I'm your host, Tony Stewart. Today I'm joined by Maria DeSteuer, founder of Second Half Community. Maria, welcome to the podcast.

SPEAKER_00 0:28

Thank you. It's such a pleasure to be here today.

SPEAKER_01 0:31

Yeah, I'm excited to have you. Thanks for again for joining us. So uh to start off, tell us a little bit about yourself. What is your origin story and how did it lead you to launching the second half community?

SPEAKER_00 0:44

Yeah, you know, I, like many women and many caregivers, was chose, I chose to leave my career to raise three kids. But during that time, I was also hit with a rare and chronic disease, became disabled for several years. And in that process of slowly healing and figuring out what comes next, um, it's really hard to come back from a 12-year career gap. How do you rebuild that confidence, the credibility? Um, is the mommy network going to help me in this process? And when I was able to climb back out and land roles at the director level and the executive director role, I wanted to be able to help people who were traveling similar journeys to make it faster and easier for them.

SPEAKER_01 1:34

Well, that's great. And um, yeah, I'm sorry to hear that you went through that with the personal health challenges. Um, so what I mean, well, how did you get your mindset around like, okay, I've been out for 12 years? How do I, you know, because it's, you know, being a parent, I I was working, you know, so I didn't have that gap, but you know, I mean, I can't even imagine what it's like to have that gap. And all of a sudden you're like, wow, I'm going back to my career. What was the mindset shift like?

SPEAKER_00 2:06

I 12 years is a long time to focus on three little beings: a family, a household, a husband. I was just ready. You know, the kids were getting a little older and they were getting involved with their own things. It was a little less time, you know, commitment. My health was getting stronger, and I was just ready to make an impact in a different way. But it's, you know, we're we're all have so many skill sets. I was that mom who volunteered in the classrooms and ran the was a soccer mom and ran different fundraisers. And so there were a lot of skill building during that time. But how can you like that the need to contribute to my household in a different way? You know, my husband worked for the government and there wasn't a lot of extra money. Um, club sports are very expensive, cars in college. So I just I wanted to be able to contribute in a different way. Um, and there's just this desire. Um, but how do you get back in? And it all started with just conversations with everyone in my network.

SPEAKER_01 3:12

I I like that, is it started out reaching to out to your network. Um, and that's something I had a couple of guests on who were just, you know, the conversation was just about the power of your network. And you're right. And although it makes me laugh thinking about club sports, is boy, I wish I had invited Club Sports. You know, those that's ridiculous. All parents out there, you can identify with how much club sports cost.

SPEAKER_00 3:40

It's yes. Uh, and the better they get, the bigger the price tag. Um, and when I work with clients, I often hear they're like, Well, Maria, I don't have the kind of network that's going to open doors for me. But my first job back came through a mother in the bleachers at gymnastics. You know, she knew someone who knew someone who was looking for a membership director. Uh, I just talked with one of my clients who had landed an interview. I'm like, how did you land that interview? Because it's it's very hard to get a job right now, especially if you're over a certain age. She's like, Oh, I was in my brother's driveway talking to his neighbor, and they had a job opening at their company, and I went several rounds of interviews. You do have a network.

SPEAKER_01 4:27

Oh, I think that is a great point that we all have a network, is sometimes it's not the network that we think we have, but it's everybody that we are connected to. And that's how a lot of people get jobs is I don't want to say by accident because that's not quite the right word, but by good fortune or being in the right place at the right time and hearing it is and it is tough out there. So um, what things you talk about is a portfolio life. What is a portfolio life?

SPEAKER_00 5:00

Well, to to uh use meta um money terminology, it's when you diversify your identity, you don't tie everything to one thing, um, and more specifically a portfolio career. It's creating those multiple streams of income and and multiple streams of meaning and multiple streams of resilience. Because if one of those things collapses, you're still, you know, have other things to hold you up.

SPEAKER_01 5:31

Yeah, I I I love that as, you know, I was just making a note is that sometimes we get really stuck on one meaning, and that that even gets back to what you were talking about is that we get stuck, uh, well, I shouldn't say stuck, but you know, in that purpose of being a parent. And it's very easy. I I did a lot of volunteering at my son's school. I managed his little 18. And so it's a big part of my identity and life. And all of a sudden it's like you're not doing that. And it's like, okay, what do I do with all that extra time?

SPEAKER_00 6:02

So absolutely. Empty nesting is is real. Um, and sometimes people pivot because they feel it's time to move on, but sometimes we pivot because we have to. You're um divorcing, you lose your job, or you're empty nesting and you suddenly have all this new time, or you or through divorce, oh, suddenly I have to support myself. So there's many different reasons why people would pivot. And to have a portfolio life or a portfolio career is like those are traumatic experiences. But if you also have uh your friends, your family, you have a church community, you have health and wellness, you have all these other things that help sustain you and give you a support structure if one of those were to fail. And with a portfolio career, you're diversifying, just like you would diversify your investments, but you're diversifying those income streams, that earning power. So you're not putting all those eggs in one basket.

SPEAKER_01 7:05

Yeah, I love that is don't put all your eggs in one basket. That uh that that's you know very always great advice. But you know, as you point out, is that these things help you through life's transitions because life is full of transitions. And so you have to be able to pivot, and you know, that's where your network comes in is to help you, whether it's your support team or whatever else. Um so you know, if somebody's stuck in a place and they're ready to move on, how do they start to spot the signs that, okay, now's the time that I should move on?

SPEAKER_00 7:48

Yeah. As I said, sometimes we pivot because we want to, and sometimes we pivot because we have to. But there's always those silent whispers before the big crisis. Uh my brother saw that their company stock was just going down and down and down and down and down, and they're trying to pretend like no one's gonna get laid off. But okay, that's that's a sign. Um some signs might be things like you feel competent at your job and it's easy, but you just never feel alive. There's no joy, you're not being lit up. Um, you've outgrown the problems that you are tasked with. It's just it's easy, it's routine. Um, sometimes it's just exhaustion. You just can't pinpoint why you're always tired and unmotivated. Um the the Sunday scaries, all you know, all those sorts of things.

SPEAKER_01 8:47

Yeah, I I I I haven't heard the term Sunday scaries, but I I get where you're going with that. I'm assuming it means when you're not ready to go to work on Monday morning.

SPEAKER_00 8:58

Yeah. Yeah.

SPEAKER_01 9:02

So, you know, as we talk about it and, you know, people start to spot the signs, how can they start to, you know, make that switch to saying, okay, I I'm seeing the signs, but how do I actually start to transition myself to moving on? Because that that in itself is a huge mindset shift.

SPEAKER_00 9:25

Yeah, for sure. And and it's it's first understanding who you're becoming and realizing that the people, the education, the all the things that got you to this place are probably not going to be the things that are gonna get you to that next place. So how do you expand yourself? You put your head up, you start hanging around with different people. You put yourself in rooms that feel a little scary. You experiment, you try things, um, you consume different media, different podcasts, learn about something new. You never know what's going to be that thing that's going to either connect you to an opportunity or help you just grow your vision of what the possibilities are.

SPEAKER_01 10:12

Oh, right. I love that. Grow the vision of what the possibilities are. And I think that's, you know, it's so easy to get stuck and say, okay, well, this is just it, instead of looking like, wow, the, you know, there are more possibilities. And I think when we see all those possibilities, then we can move to them. And I guess that's making that switch from scarcity to abundance, that there are there is an abundance of opportunities out there.

SPEAKER_00 10:38

Yeah. And if you feel like there isn't, that's you need to get away from the naysayers. You need to get rid of rid of those stories that you've been telling yourself over and over in your head. It's too late, I'm too old, my experience is outdated. My experience was outdated. I had a 12-year gap. Now, yeah, like there is a way, and and you have been upskilling. And even if you're caregiving, that coordination, putting yourself out there, um, advocating, there's there's always skills that you're getting in your daily life. Um, and just learning how to repackage yourself and knowing that it's you are gonna fail, and that's okay. There's growth in that failure.

SPEAKER_01 11:17

Yeah, and and I've heard that from other guests, you know, is growth and failure. And that is it, is you know, is when you think about kids learning how to walk, is they fall down a lot, and it's just part of the process. So, you know, life is like that. And as we, you know, work with our money or life, you know, we we are gonna make mistakes. It's you know, in my mind, it's how you recover from the mistakes and makes all the difference.

SPEAKER_00 11:45

And that's where the biggest growth comes. It sounds like so cliche, but you know, once you fail once, you don't want to do it again. It hurts, it's uncomfortable, you know, and and that's when you're gonna grow and force yourself to move from this uncomfortable place to what's next. Because sometimes it takes un you know, discomfort to make us move out of this monotony or safe zone.

SPEAKER_01 12:09

Yeah, and that's a that's a hard thing is to move from that safe zone, you know, to to whatever you want to do with your life. Um, but I'm reminded of I'm I'm a basketball head, uh, so you know, I'm reminded of a quote by Michael Jordan where he talks about all the times he failed. And he said, I had to miss so many shots and fail so many times in order to be able to succeed and hit the game winning shots and do the things that he did. And so it's inspiring from someone like him who you're like, he's Michael Jordan, you know, how could anything ever be tough? But when he talks about all the times he failed, it's you know, it's just what you're saying is that failure is part of his growing process.

SPEAKER_00 12:54

Absolutely. And I grew up in Chicago, you know, enduring the whatever four Pete, six Pete, eight Pete, whatever. You know, they just kept winning and winning, winning. And it was great when I was older and able to read those stories about the failure behind it, about being cut from the high school team, and just you know, just keeping going, believing in yourself and surrounding yourself by people who build you up and don't place limits on you.

SPEAKER_01 13:23

I love that. Surround yourself with people who believe in you. And I think that's really important is you know, one of the topics that's come up on the show is you know, um we've talked a little bit about financial abuse and domestic abuse and things like that. And so, you know, if somebody is listening out there and you know, there are people who are grinding you down, um, however you want to phrase that, is that you know, you can take your life and change it and find people who are going to support you and help you grow instead of grinding you down. Um so one of the things you also talk about is aligning work-lives with goals and values. So, how can people align their work lives with their goals and values?

SPEAKER_00 14:16

I think it's important to understand that it changes. And just because you're evolving or changing doesn't mean you're uh neglecting who you used to be or that that was wrong. But you know, we all grow and change and evolve as people. Uh, things that are going on around us change. Uh, things the way we used to judge people, the standards are different. Um, so just understanding who you are and who you are becoming, who you want to be next, how you want to make an impact. Um, in the format of a career, some of the questions I ask people, and and they're like, wait, you're asking me that? Like, what do you want a day in the life to look like? Do you want to go to the office? Do you want to work nine to five? Do you want flexibility? Do you want to commute? Do you not? Do you want to travel? Do you want a big team, a little team? Like all these questions, and people are like, wait, wait, wait, wait, wait, wait. I can decide that for myself before I look for a job. Yes. And I'm not saying you wouldn't ever have to shift some of those things, but it's very helpful if you understand what your non-negotiables are, how you want to create your impact, and how what you need from this job or career or whatever you're spending your time doing, how it supports your life, your rich life, your life that you have a vision for with your family. You have to understand what you need and want to build it.

SPEAKER_01 15:43

I love that. You have to understand what you need and what you want. Um making a note on that. Um, so I I I love that. I love where you're going with the non-negotiables because I think sometimes we forget about that. Is yeah, sometimes some of us are stuck in jobs that we can't easily get out of, but you know, that doesn't mean that we can't be thinking about finding a job or a career where we are able to thrive and you know, as you point out, live your rich life. So, you know, as part of that, how do we launch our second half and our next act?

SPEAKER_00 16:27

Giving yourself permission to do it, raising your head up. Um what I said earlier, knowing that the things that got you here aren't necessarily going to get you there. Um putting yourself in those rooms, experiment, uh consume different media, things I've already mentioned. Um, finding that team of people around you that will mentor you. Uh, maybe it's connecting with someone who's already doing something that you think is so cool and you just want to be near them. You just want to experience what they are to see if that might be the right thing for you.

SPEAKER_01 17:04

I love that is exploring uh different things. You know, sometimes we forget that, you know, when we're in school, it's easy to think about experimenting. But sometimes, you know, in our careers, we think, well, you know, I'm limited to what I can do, but that's not necessarily true, is you can. And as you point out, is you you learn different skills no matter what you're doing, is you're always learning skills.

SPEAKER_00 17:30

So yeah, you know, and it could be something like saying yes to a project at work that is outside of your scope. It could be going on an advisory board, doing a volunteer role, you know, and I work with many people who are in a quote job they can't get out of. But the minute they start this work of letting themselves dream again, going, going on a different path, consuming, talking to different people, saying yes to different projects, they the like the pressure valve gets released. And even though they're still in that same job right this second, because they know they're taking the steps that are that eventually is going to get them out, it just lifts them up and helps them feel better now.

SPEAKER_01 18:18

I love that. I love that. Just let yourself dream, go outside your comfort zone, and it can be hard to go outside your comfort zone. Absolutely. So, however, what I found is a lot of times when you go outside your comfort zone, it's not what you expect it to be. And it's oftentimes a lot better than you expect it to be.

SPEAKER_00 18:39

And going out of your comfort zone can be little things every day. Like every day you should do something a little scary. Drive a different route. Say yes if someone says, let's go rock climbing. Uh, join Toastmasters and learn to public speak. You know, that say yes to a leadership role that maybe you don't feel quite ready for. Step up. Like it every day do something a little scary.

SPEAKER_01 19:07

You know, I think you said something there that is absolutely critical is to say something, say yes to something that you don't feel quite ready for. Yeah. I I think that's a big part that a lot of us feel is that you know, we we have uh imposter syndrome or whatever you want to call it, but we have that feeling that we're not qualified to do it. And I think that you know, we all can say yes to things. And yeah, easy, you're never ready for anything. We're never really ready for anything.

SPEAKER_00 19:43

Yeah, there's all it's always gonna be a first.

SPEAKER_01 19:47

Exactly. And you have to do it. If you don't take that first step, you'll never get there. So one of the things you talk about is, you know, let's move just quickly to a career pivot. Is why is it important to know your numbers when making a career pivot?

SPEAKER_00 20:05

It's a it's a data point. I work, uh, I spoke to a group of out-of-work tech executives. These are people who were CTOs, CISOs, you know, just lots of initials, earning multiple six figures for a decade or more. And I remember speaking to this group, and there were people who uh wore their stress. It is stressful to be unemployed. It is job searches are brutal. But the the what they were talking about was every month I watch the money draining out of my savings, and they know I'm gonna have to replace it. And me and several others in the room are looking at this person like, are you really though? You may already be transitioning towards retirement. And another person in this group is like, oh yeah, I ran the numbers with my husband. I figured out I don't have to be a CTO anymore. This person went a got went and got a job at a ski resort for fun and then took consulting jobs on the side to pay for those higher ticket items like kids' weddings and travel. When you know your numbers, you're not making a decision out of this desperation, like, I've always had a job, I've always had a job, I have to have a job, but um, I've always been a CTO, I have to keep being a CTO. But do you really? So knowing your numbers lets you make an informed decision about what this next career move or thing has to provide you.

SPEAKER_01 21:31

I love that. And that that you know, it goes hand in glove, is what you were talking about with your values and everything else, is when you're making a career pivot, is it uh you know, aligning all those things helps make it the right fit because maybe you don't need that stress anymore in your life, and sometimes you know uh we live the life that we think other people think we should, or that other people Are leading instead of leading the life that is right for us.

SPEAKER_00 22:05

Absolutely. And I know many people who are retiring in their 50s and people look at them like, wait, well, or even earlier with the fire movement. You know, people are retiring. You're just really, you know, and and maybe we need to re-redefine what the word retire means. You know, retire doesn't mean I'm never going to work. It doesn't mean I'm going to not make an impact or contribute to society. It just means I get to choose how and what I do with my days.

SPEAKER_01 22:37

I get to choose my days. I I love that. Um I and that it's something on this podcast. People who've watched and listened to this podcast know that we've talked about it. Kathleen Rell talking about refirement and uh, you know, just all the different people and financial independence as you talk about for, you know, the fire movement, uh, you know, financial independence retire early is something that also sometimes people regret doing as well. So it's like finding that right middle ground for what works for you, but it is getting that freedom of choice. And that's that's what life should be about, having the freedom to choose.

SPEAKER_00 23:21

Yeah, that whole thing of living to work or working to live. You know, we it would be nice that you know, our work supports our life. You know, there are many people who just live, live, they're like just work is all they do. Some because they have to, some out of ambition, some out of just this broken record in their head that this is what culture says you have to do. Getting to that point where work isn't everything, it shouldn't be everything. It's a it's a mechanism to fund your life, your fun.

SPEAKER_01 24:03

Yeah, I I I love that. So, one of the things you talk about is transforming your life. What are the benefits of transforming your life and work as we've been talking about? You know, I you just you were starting to talk about that. Anything else you want to add to that?

SPEAKER_00 24:20

You know, it's just especially if you talk about a portfolio career, it's just building that security beyond one paycheck. And when you talk about passive income, everyone's like, ooh, passive income. You know, there's no shortage of reels and videos and that do this and do that. But if you stop and think, even in a more traditional trajectory in this country, you already have some passive income that you don't even consider. You might have stock that pays dividends, you might have uh CDs, you might have a home that's appreciating in value. You know, there's there's other ways that you're making income that you may not even really be aware that that's technically passive income. So you already have a portfolio of incomes coming. How can you grow that?

SPEAKER_01 25:13

Yeah, I I I love that. Is and that's something is about knowing your financial life is, you know, for people who subscribe to my newsletter, get my weekly action items, is that's one of the things we, you know, that I suggest to people that they go through is to think about all their different forms of income. And instead of just constantly focusing on cutting expenses, is to think about ways to maximize income, like you're talking about, because sometimes there's small pivots you can make with your income that can really make a difference to your life. And then it takes off the pressure of, like you said, is maybe you don't need to be a CTO if that's stressing you out and you're not getting enjoyment from it. Um so Maria, let's um, you know, it's the wrap-up time is what I call the get ready hot take trio. These are three quick questions I ask all of my guests. Uh, the first one is what is one career myth you're trying to break?

SPEAKER_00 26:15

It's that a nine to five employee job is safe. I I'm sure that we've all seen, even federal workers, that was considered very safe for many, many years. Um, nine to five employee jobs doesn't equal safe.

SPEAKER_01 26:31

Yeah, and I think we can say that goes double right now in the age of AI, is that we we don't know what jobs are safe going forward. So building skills will help you um because you never know what's gonna come uh down the board across the board. And one of the things about AI that I feel personally is we have no idea what's gonna happen. Um, there's predictions that run the gamut from it's gonna be abundance to it's gonna eliminate every job ever created. And in truth, it's probably gonna lie somewhere in the middle.

SPEAKER_00 27:07

Absolutely. So yeah, and just be up on it, use it, play around with it, understand how it can contribute to whatever it is you do. And if you truly see an end point for your career because of AI, adapt now, not before when it's a whisper, right? Adapt early before it's a crisis.

SPEAKER_01 27:29

I love that. Adapt early before it's a crisis. And you know, that's something that I'm leaning into this with this podcast and the name change, get ready before life happens, is you know, yeah, the earlier you can prepare, the better. So, Maria, let's get at the time machine for a minute. If you go back in time, knowing what you know now about careers and money, what advice would you give your younger self?

SPEAKER_00 27:59

I came from a small world. I came from the south side of Chicago, Chicago public schools. My world was tiny. So my advice to myself would have been get in bigger rooms, surround yourself by people who are doing bigger things than you can imagine, because that's when you grow.

SPEAKER_01 28:20

People who are doing bigger things. So the last question is what's your number one tip to change the way we think about our careers in life?

SPEAKER_00 28:30

Because I work often with women and because of my trajectory, you can't build or design your life if you're designing it around everyone else first. Put yourself first. Figure out what you want, and then you can put in them, though all the other pieces.

SPEAKER_01 28:54

I love that. Is I I I think, you know, and it gets back to what we were talking about earlier, is uh living somebody else's life and career. Um that doesn't work, and you're never gonna be quite happy doing that. You may survive, but you're not gonna find happiness if we're doing that. So that's wonderful advice. So, Maria, where can people learn more about you in the second half community?

SPEAKER_00 29:20

Uh website, secondhalfcommunity.com, and or I am the only Maria DeStour on LinkedIn, and I love to connect with people on LinkedIn, especially around career. Let my network become your network. Reach out, let's connect. I'm always happy to chat.

SPEAKER_01 29:39

Fantastic. Well, Maria, thanks for joining us on the Get Ready Before Life Happens podcast.

SPEAKER_00 29:46

It's been a pleasure, and um, I I love money. Uh, I love that you're having these conversations and you provide this platform to challenge people to evolve and grow their mindset around money and life. Thanks for having me.

SPEAKER_01 30:01

Yeah, it's been a pleasure and appreciate your kind words. And thank you, everyone, as always, for tuning in to get ready before life happens. So if you learned something today to change the way you think about money and life, please be sure to subscribe and to share this episode with a friend. You can also go to my website at TonyStewart.com to join the get ready movement and receive my newsletter and a whole bunch of free resources. Until next time, let's change the way we think about money.