Can Your Passion Become a Side Hustle After 50?


If you've been thinking about starting something on the side but you're not sure whether it's worth the time, the money, or the risk, this episode is for you.
Turning a passion into a side hustle after 50 can feel uncertain. Many women know what they enjoy or what they are good at, but they question whether it can realistically become a business. In this episode, Georgianna shares how she turned something she genuinely loved into a paint party business while still working her full-time job.
She didn’t start it because she was a painter. She started it because she wanted something to land on if her day job disappeared. What began with a tax return and a market scan turned into a sold-out business she truly enjoys—one she rebuilt after COVID, a relocation, and a major career shift.
Josefina Bonilla Velez and Georgianna talk honestly about what it actually takes to start and sustain a side hustle after 50. They walk through the financial logic of starting small, recognizing real demand, keeping risk low, and building something meaningful that fits your life.
This is not a highlight reel. It’s a practical conversation about momentum, community, and thoughtful decision-making for women who want to move forward without pretending they have unlimited time, money, or energy.
What you'll hear in this episode:
00:00 Introduction: Meet Georgianna
00:25 Georgianna explains her paint party side hustle
00:45 Why she started the business as a safety net
02:10 Discovering demand and doing the “paint party math”
03:26 Learning the business and launching in 2014
04:05 COVID shuts the business down
05:22 Rebuilding after relocating and starting over
07:45 Finding a supportive paint party entrepreneur community
09:03 How much time a side hustle actually takes
10:11 What keeps her motivated
11:09 What to consider before starting a side hustle
12:05 How to book a paint party with Georgianna
12:53 Closing thoughts and Money and Motion sign-off
🌐 Website: https://moneyandmotionpodcast.com
#WomenOver50 #SideHustle #MidlifeReinvention #WomenEntrepreneurs #Women50Plus #StartingOver #FinancialEmpowerment #JosefinaBonillaVelez #GeorgianaArtBar #MidlifeMoney
Josefina Bonilla Velez: Georgiana, thank you so much for joining us. I'm so happy you're with us. Tell me a little bit about yourself.
Georgianna: Well, so I'm from Massachusetts â and spent some time living and growing up in Puerto Rico. And of my work has been in Massachusetts. And so â I've a lot of different careers â and kind of at the point now where I'm doing the thing that I had, â that pathways led me to â and loving it.
Josefina Bonilla Velez: So tell me about your side hustle.
Georgianna: My side hustle. So I have a paint party business and it is super fun. when I launched it, I was not a painter. I â hadn't since middle school, up until months before I decided to launch this business.
Josefina Bonilla Velez: wait, what made you decide to launch it?
Georgianna: the time, â there periods in your work life where the work environment feels unstable â and really hard to put faith â in people to determine your future financial destiny. And part me wanted to have something that should the choice not be mine to leave an organization or the, you know, something changes, they reorg, something happens that I had something that could keep me going and it wouldn't pushed me so far back. So I never really intended to leave my full-time job, but I wanted to have something to land to keep me going. So that's why I launched it when I did. And I went. some friends to a party and paint party. Kicking and screaming, I didn't want to go. I didn't enjoy â art. very creative, but the painting part, â So â went and had such a good time and I home I showed my family my painting and â they oohed and ahed and it made me feel really good. And liked the way that it made me feel. I liked that experience. So then I went on to YouTube University and I learned how to paint. I bought my own painting because, you know, going to the parties for me was a big investment. Like it's okay to go once in a while for fun, but the rate I wanted to do it, then I was like, how can I write this off? Like this is a lot of money on paints and supplies. Yes.
Josefina Bonilla Velez: Thank wait, there's a disconnect between you going to your first party and then you deciding you want to do this for a side hustle.
Georgianna: Okay, no, you're right. There's a gap in the story. So, was doing this painting, and I was at home and I was learning and, having a good time with it. â one of my brothers â having a birthday and I suggested that we go to a paint party. And took me three, â we to go out three weeks, because every around us was sold out and they were doing five, six parties a week and they were sold out. And I was like, â wow, this is there's a huge demand for this, right? And so then we show up to the party and I'm in this brick and mortar place with 40 benches and like easels and I'm just doing the math, right? I'm like, they had a party earlier today, this is the second party today to have another one tomorrow and I just did the math. And I was like, you don't actually need to have a brick and mortar either because I'm not planning to leave my day job. So the entry point for something like this was a low risk. So I... I started, that's when it started kind of taking root in my head. I, it â around the time when tax returns were coming â I was thinking, well, I could pretend I didn't get a tax return. And I took the money and â immediately invested in, you know, the website and â which I did â what they call that? A market scan, right? So. â
Josefina Bonilla Velez: Right, right.
Georgianna: I looked at how many businesses were in the area. I actually went to more parties to do some research about like, how do you run this? Like, what does it look like? And my biggest obstacle was making sure that I felt like I understood how to paint enough to help others do this. knew how to teach. â in my background, I'm outreach educator. â know, I know how to get people's to pay attention and to be hooked. â Like part was there, but the painting part was YouTube University and still something I spend time learning. Now it's been established in 2014.
Josefina Bonilla Velez: But you established in 2014 and then it stood a little quiet for a while and then you restarted it, right?
Georgianna: Yes. Yes. â hit and it's a, it's an event platform at the time relied on people coming together in person. So you are entertaining people. are, there's no downside to this business. it's just the appeal for this particular business â that are just coming to have fun. They're there for two hours. â They leave something that they're happy with. I, it's always So.
Josefina Bonilla Velez: Sorry.
Georgianna: COVID hits and at the time I didn't have the technical skills to figure out how to shift this to an online modality. And so I walked away from it for a little while. I just let it go to sleep. And now back. Like we figured out how to navigate â wearing and doing things like that. And I relocated. Like I've made a lot of big changes in my life. â I relocated, left a job, I started a new career. and it felt like this was a good time to try again, right? So it was successful when I did it. COVID was the thing that pushed it aside, but you know, here I am and tomorrow I have a party that's sold out, you know? So really fun. Like I am so excited about going to the party tomorrow.
Josefina Bonilla Velez: Bye. I am sorry I'm going to miss it. As you know, I'm flying out to Puerto Rico tomorrow, honestly, would have been â â me about your challenges. What have been some of the challenges you faced? â necessarily at the beginning, because I feel with you starting again, you sort of reinvented what you were doing. So can you talk a little bit about the challenges?
Georgianna: was my little violin. It's okay. You know, I will say that the difference between then and now for me is that I'm a lot more confident in my product. Like I know how to run the business. For me, the biggest challenge is my network, right? So I've relocated to a different part of the state â have been working to establish a circle here. And so I've had to think about my business in a different way and approached it with figuring out partnerships â of who are established in this area. And so. They need people to come to their businesses or to them to do things and I need that as well. â have the network, I have something that will add appeal and so we've been working together. That's been super successful for me. My sold out party tomorrow is with a partner. I partner with a farm. We do things that wouldn't have even been on my radar when I first started doing this, but I'm trying to be creative and also having a lot of fun.
Josefina Bonilla Velez: And remember, â the most important financial decision you will ever make is deciding to pay attention. We can't back, but we can move forward together. And remember to subscribe now. wherever you listen to podcasts.
Georgianna: real challenge is I haven't been back long enough to understand the cadence of like, is it, if I don't sell well in a party, is it about my partnership with the venue or is it about the time of year? know, so there are things that I'm still navigating as an entrepreneur because I don't have enough time in a particular space. So in this part of Western Mass. So. I also did something different this time that has helped me. Now I research as part of my day job, I research entrepreneurship. So I know that when you want to be good at something, you immerse yourself in that community, right? You're supposed to be around people who are thinking about the same thing. it's one thing to immerse yourself around other entrepreneurs because we're all hustling to be the best that we can be. And that's helpful and useful, â I hadn't. figured out how to immerse myself with other people who run paint parties, because we're in competition with each other, right? So we're vying for the same venues or, but I found a group online that a membership would was really exactly what I was looking for. And at first, when I joined, I was thinking, I think to join this place because they have paintings that I could use and that would help me not have to come up with new paintings. And what I was a community of people who were sharing strategies. and who weren't afraid of competition, who are really about lifting each other up. And for me, that's home. I want to be around people who lift each other up. â â would give you stories about things that didn't work well. â they would say, I wish I had known this before I did this type of party. I tried this product, and here's what happened with the product. Maybe you'll have a different experience, but you should know that wrap it this way. So little things that save me a lot of time and also give me creative ideas. Like I didn't ever consider buying sleds to paint I actually really had a hard time pulling the trigger because you know, you're an entrepreneur you front a lot of money for product and you don't know if people are going to come â so I kept watching them be successful so I did it and it was successful, you know, but it's hard to be brave when you are spending money. that â you don't know if it's going to yield a return. â know, being in this place of risk taking, I think I'm a lot better at taking that leap, â I'm also a lot more discerning than I used to be about why I do this? And would I like it if I did it? And so I don't do anything I don't want to do anymore. So.
Josefina Bonilla Velez: That's awesome. much time are you spending? And the business?
Georgianna: On the business, so the reason I, so the quick answer is as much time as I want to, right? So I get to decide because I don't have a brick and mortar if I'm going to schedule two parties this week or once this month. per party, my investment in the party itself is usually about five hours, the setup, â the delivery and the cleanup. And I, ahead of time, it's the marketing and the average, you know, the setting up the materials finding venues. So â average, I probably spend about 10 hours a week on business. And if a week where I have multiple parties, like this week, I have one Saturday and one Sunday, it will be more. And there are weeks where I've said, you know, this week I have a lot going on in my day job. so I'm not scheduling anything or I'm going on vacation so I'm not scheduling anything. So it gives me the flexibility, the way that I built this to choose when I'm going to invest time. But it does require momentum. So you can't take big breaks. have to keep advertising. You always have to have something on the calendar. â so I'm out there having coffee with people that I haven't met before and building new partnerships. â
Josefina Bonilla Velez: And what's motivating you? Because I know sometimes when you start a business, you have to be self-directed. Nobody's telling you when to do it, how to do it. And you have to push that yourself. What motivates you to move forward?
Georgianna: Well, for me, it's fun. So I pick something that is fun for me. I would paint if it wasn't to be paid. â get my energy. I'm an extrovert on steroids. I get my energy from other people. I'm someone who could go to the fair and just walk around and be so happy. Where other people need to be alone to recharge, I charge around people. So my motivation is â I it. And I to try new things. I like meeting new people. So the business model and my passion for what I'm doing converge.
Josefina Bonilla Velez: That is very nice. Now what would you tell someone that is thinking about starting a side house or maybe something similar, what should they consider?
Georgianna: think that if it feels like work, like if you dread it, you should probably listen to that because the amount of time that you have to put into it and the times that you have to ride out droughts because there are, it's feast or famine, even with pain parties. Like during the holidays, you would think, â everyone's going to go to party. They don't. They go different kinds of parties â that there times when whatever business you're going to â launch, will have its hot times â its slow times. And so if you're not passionate about it, if you don't love what you're doing, if you wouldn't do it not being paid, think hard and long about whether or not this is something you want to invest your resources into. And resources and money, but it's also your time and energy. â I give up going to things or different kinds casual things that I might do to do this instead.
Josefina Bonilla Velez: And how would someone reach out to you to book a party?
Georgianna: So I have a website, masterpieceartbar.com. all social medias under the same name, â And are links there to send me an email or my phone numbers on there so that you can just call. I, know, beauty of this is I do have events that are, that anyone could just buy a ticket to and come. But I also have worked with, you know, I do parties at organizations who want to â have some of a bonding activity with their team. nonprofits who want to do something for their clients. I do birthday parties. I'll come to your home and I'll travel. â So a limit to the travel of how far, but try me, ask me. And if I can't, I'm part of a network where I can help you find someone who can do the thing. That network for me has been a game changer. But I love I and I'll bring that energy to your party.
Josefina Bonilla Velez: Great. Well, thank you, Georgiana, for joining us and we will see you soon.
Georgianna: Thank you, Josefina.



