Trading Commas And Contracts For Creativity

Your life can look “successful” on paper and still feel wrong in your body, and that quiet mismatch is often the real start of midlife reinvention. I sit down with Osayi Lasisis, a business-to-business growth leader and fractional growth marketer, to talk about what happens when the identity you worked for stops being the identity you want. She planned her whole life to be a lawyer, earned the credentials, and chased the most prestigious track she could find, only to realize the day-to-day work drained her spark.

We get into the messy middle: career disappointment, depression, the weight of expectations, and the fear of hitting pause when you don’t yet know the next move. Osayi shares how returning to Nigeria became a reset that opened space to explore new skills, rebuild confidence, and eventually embrace marketing, events, and go-to-market strategy as a creative path that still ties directly to revenue. If you’re navigating a career change, burnout, or a midlife crisis that doesn’t match the stereotype, this story offers both clarity and permission.

Then we shift into purpose-driven entrepreneurship with Pocketlings, the brand she co-founded with her daughter after her 10-year-old couldn’t find brown plush dolls that looked like her. We talk representation, building products from real needs, creating affirmation books for kids, and even entrepreneurship training through libraries and community groups. We close with simple, real practices for staying connected to your people and a line worth repeating: fear is normal, and investing in your joy pays exponential returns.

Subscribe, share this with a friend who needs a reset, and leave a review so more women can find the circle. What part of your life is asking for a brave pivot right now?

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Transcript

Episode Kickoff: Ignite Your Spark

Speaker 0:02

Welcome to the Find Your Lady Tribe Podcast. This season we are deep diving into the heart of Midlife Reinvention. That sense that you've mastered your roles, but you've lost your spark. You are exactly where you need to be. This season is inspired by the framework of my upcoming book. Ignite your life's purpose and save the world. We're gonna help you move from autopilot to on fire by hearing from incredible women who have reclaimed their own life force. It's time to stop just going through the motion and start living your next chapter with intention. Let's ignite that spark. Save the world, sister. Hey everyone. Welcome back to the Find Your Lady Tribe podcast. My name is Brenda Ridgley, and I'm your host. And today I'm super excited to have a guest on. Her name is Osayi Lasisis, and she's got a great, incredible midlife transformation story that she's going to be sharing with us. But first, I'd like to just kind of tell you a little bit about her background. Osayi Lasisis is a business-to-business growth leader with 13 plus years of experience turning events into revenue engines. As a fractional growth marketer and GTM strategist, she has closed accounts and built 100 plus enterprise opportunity pipelines through account-based event strategies, virtual conferences, and personalized engagement programs. She is also the founder of Pocket Lings, a brand she began with her 10-year-old daughter when her daughter couldn't find brown plush dolls that look like her. So they co-create dolls and books and facilitate training events for kids. Osayi, thank you so much for being here. Welcome. Thank you, Brenda. I'm so excited to be here.

Speaker 1 1:57

Thank you.

Why Midlife Is Not A Number

Speaker 1:58

Awesome. Well, I just want to jump right in because, you know, you are, you know, a younger mother in the midlife scheme, you know, of all the life stuff that we have going on. You know, women have, you know, uh careers and kids and family and all the all the boxes that we check along the way. But you you have children at home still, but have already lived a bunch of life and feel very much that you've been through, I think, a number of transitions. And I I think it's just important to go to say because I don't think midlife is a number. You know, we discussed this earlier. Midnight midlife is an experience level. You've checked some boxes, you've gone through some hard stuff, life has thrown some stuff back at you, and you thought you were on track and you and you have to readjust. And that can happen, it does happen several times throughout your life. And I want to hear your story, what you feel like kind of your midlife transformation has has occurred so far. So so just I'm gonna let you start.

Walking Away From The Lawyer Dream

Depression, Shame, And A Hard Reset

Speaker 1 3:04

Yeah. Um, like you mentioned, I've been through a few of those transitions, but I'd say the most defining one for me was no longer being a lawyer. So my whole life as a kid, I planned to be a lawyer. I looked for the hardest, most prestigious job out there. And that's the one I wanted. And being a lawyer was that for me. Um, so whatever classes I needed to take, I took them. Whatever programs I needed to be a part of, I did that. And then um whenever it was time to do like personality tests, I always skewed it towards being a lawyer. Like it needed the I needed the results to say lawyer, you know. So it was it was such a fun experience when I was in high school and things were tough, and you know, some teachers that I felt were being unfair, but in my mind, I was always like, when I'm a lawyer, I'm gonna show you, you know. Um, and then I went to law school, I even got a scholarship to law school, and that was so exciting because I almost couldn't get in because I couldn't pay for it. Then I got a scholarship, and you know, just like going through everything, like I'm gonna get this. And then I'm in law school and I'm kind of like, ooh, I'm not quite sure if this is what I thought it would be. Because, like I said, the way I decided was the most prestigious, the the one that would pay the most. And I didn't really think about what I would enjoy. And so I was like thinking about contracts and compliance law, and it was just like, yeah, we don't have a lot of black women in there, so I'm gonna be one of the few black women, just all of that. And then I get out of law school and I was still going, but then a few things happened. One, we had the financial crises of I think that was like uh 2008, um, the housing crisis. So it was so hard, and I was an international student in the US, so it was so hard for me to get a job where they were willing to um pay for somebody who is, you know, that there's that additional fee for an international immigration and all of that stuff. So that was challenging. So I got some jobs, but I wasn't as excited about it. And then I started dealing with some depression because I was having this like crises of is this what I was supposed to do? I'm not quite enjoying it. Um, is there something else out there for me? And so I decided that I needed to take some time away because it was getting quite serious. And and so I was like, I'm just gonna go back home, go to my parents. But what's interesting about that is my parents were not just like across the street. I was in the US, I was in North Carolina at that time, and my parents were in Nigeria. They travel a lot, but they were living in Nigeria, so it meant uprooting from what I was comfortable with for the last couple of years and trying to re-understand living in Nigeria and dealing with the thought that I might never come back to the US. I might be what felt like stuck in Nigeria because there's so much that's different in Nigeria. And because all my education was in the US and I had my bar license and everything, but it was US, I would need to get all that education again and get recertified and everything if I decided I wanted to practice in Nigeria. So it was really scary for me. And then there was that shame and that fear that I had failed that, and this is somebody who was always like this big achiever, this doer. Like my brothers were always, oh, you're the smartest one in our family. My parents were always, oh, you're so smart, you can do anything. And it just felt like I had failed. I cannot do anything. Um, and my whole identity.

Speaker 6:52

Let's talk about that a little bit because you went into law school all gung-ho and excited. Were you getting any external, like you should shoulds from people, like because you're the smartest and all this, you know, and setting up these expectations for this role that you created for yourself?

Speaker 1 7:13

So, what was interesting was that I wasn't getting any you shoulds. Um, some people would recommend like the medical field. Oh, be a nurse, you'll always have a job, those kinds of things. But being a lawyer was like prestigious enough that people were like, oh, is that what you want to do? Yes, I have respect for you. And then while they never said you should be a lawyer, being able to say my daughter, the lawyer, or my sister, the lawyer, or whatever, um, was such a big thing for people that it made me feel good. So considering not being that person anymore just made me feel very shameful. Right.

Speaker 7:51

So you totally um created this persona for you, and you were really good at it, apparently. And you were, you know, in demand and you get into the the real world, so to say, at an economically challenging time. I remember 2008 very well. Um, had businesses myself for that time that were that struggled. Um, it was a difficult time, and I can only imagine I do kind of remember the job market for uh people come coming out of college and stuff being tougher at that time. And it just kind of makes you question everything. You've been on this fast track of of success, success, success. And then you get out and and you and you mentioned kind of first, even before that, you're kind of going, is this really what I want to do? Did I, you know, how what did I get myself into? So talk about the feelings during that time a little bit for you after kind of like coming off this high. I've got my um bar, I passed the bar. Oh my gosh, that's huge. That's an incredible thing that very few people do. So tell us, you know, it seems like there was a slow letdown after that that took you back home.

Speaker 1 9:03

Yeah. So um I'd say, you know, it started while I was still in law school, and I was on the track on that track to be a contrast and compliance lawyer, which means I was going to be reviewing documents for the rest of my life, it felt. And you're looking at commas and you're looking at periods, and you're looking at the right, you know, and for some people, that's amazing. They love that. For me, it was just not, it didn't give me excitement. Like I like the excitement of researching sometimes and finding out about these big um um opportunities and where you can kind of have a merger with this company. And like those things sounded fun. But for me to be the one reviewing that contract to make sure that the merger happens in a good way and there are not all these challenges, it just wasn't exciting for me. But I continued because the promise was you'll make a lot of money, and then you can do other stuff that you enjoy. And then I get out, and I'm still feeling that kind of way. And I um was doing some fun hobbies, and that's where marketing came in. I was learning about marketing and Facebook, and uh, and then after a while, Instagram became a thing, and then I wrote a book just to like practice monetization and a blog and all of that. So that was so interesting to me, but it was so challenging to be able to say, to just think about oh my goodness, am I going to give up on this thing where people are so proud of you or that I've worked my whole life for for this marketing thing that people were like, oh my gosh, I hate marketing, I hate marketers or whatever. Um, so so that was really, really tough for me. And I would literally um be in bed sometimes and just lie down all day. And I was staying by myself uh by that time. I had my own apartment. So nobody would know. I'd just be in bed all day. I wouldn't get up. And I was like, this is not healthy, you know? And my mom would call and I would talk, yeah, yeah, yeah. But she could tell like things were not the greatest, you know. So it was it was really a tough time that I had to really think do I continue this way because I'm promised that yeah, I'll make some money and maybe things will work out, um, or do I just take a break and try to figure out what's next?

Homecoming To Nigeria And New Options

Speaker 11:29

So when you pushed pause and just to reevaluate everything and you went home, how did that feel? And I I think you mentioned that you felt kind of like a failure. You know, how were you received? How did that that home come? How was that homecoming?

Speaker 1 11:47

So there was relief at first just to make a decision and do something, but then I was so scared because I hadn't lived in Nigeria for so long. Uh most of my formative years were outside of Nigeria, so I was always nervous that I could um even function because it's a different society. And um my parents were like, oh, don't worry, we'll, you know, make sure that you are successful, we'll set you up for that. And then the other thing was I hadn't lived with my parents for so long. Um, so I left when I was like a teenager, um, early teenager, um, early teens. And then here I was like a young adult. And going back, I was just like, will my autonomy still be respected? So I was really scared. And um, but in the back of my mind, I said, you know what? I can always find a way to come back if I if I need to. Maybe there'll be an opportunity to come back. So uh, you know, I put my um the renewal of my license on on pause, like you could pause it for a couple of years and stuff. So I did that. Um, and I was like, okay, I'll renew it later. But there's a story around that as well. Um, because when I got to Nigeria, I had the opportunity to go even deeper into marketing while considering um relicensing there in Nigeria. But then I just couldn't motivate myself to go through all of that again when I was just like, I don't know that I'm excited about it. Um, maybe if I could go back, maybe I would have just picked a different um part of the the law to practice, right? Like maybe not contracts, but maybe something else that because there's so many things you can do. But um I didn't think about that at the moment.

Marketing As A Creative Revenue Path

Speaker 13:40

Yeah. So you're back and you're on pause. And that's so you're it sounds like your family just welcomed you back with open arms, and we're probably super excited you were there for the time being, anyway. Tell us about the transformation because you have found have this new thing that you that you're really kind of excited and interested in, which is marketing. And you just tell us what what happened.

Speaker 1 14:04

Yeah, so what was really fun was I had the opportunity to really explore different things that I enjoyed. So I was enjoying marketing. Um, so I was able to find opportunities, look for clients, work for clients. Um, I was practicing sales, you know, supporting, I got the opportunity to work at an agency. So I was doing that. But also, um, someone had recommended that, oh, with your legal background, you can also do HR, and we always need great people in HR. So I was exploring that as well, but it was still me leaning towards what I thought would pay me more. Um, so it was an opportunity to explore different things. And um my parents really tried to find communities for me to connect with um as much as they could. And so I said they were really helpful there, even though there were some communities that I didn't want to participate in. That's also another conversation. But uh it was just it was an opportunity to rebuild that relationship as well with my parents because I've been gone for so long outside of, you know, a few visits and a few phone calls and stuff like that. And that's kind of how the immigration journey can be sometimes. It's just like it can be a strain in so many different respects. But yeah, it was it was scary, but it was also kind of fun when I look back because I was able to really explore a lot of different things that I thought, oh, this might be a good idea. This might be a good idea. Um, and then I was able to just keep honing skills in marketing. And then I found out that, oh, I love events, um, I love talking to people, I love tying my marketing to um to revenue, those kinds of things.

Speaker 15:54

Hey lady, just wanted to take a moment and interrupt right now in the middle of the show to ask you to subscribe. Yes, press that button right now. This show is all about you, the midlife woman. Let's do this thing together. So join us, subscribe now. It makes such a difference when you find that spark, right? That go, this lights me up, not the commas and the and the periods and the uh oh my gosh, that would that minutia osay would drive me baddie. And that would be a slow death for me. I'm just saying. So I I totally feel you on that one. But you find something that really energizes you and drives you and and leads you to like a very successful career in marketing and all kinds of uh things like that. So tell us about kind of your life now.

Speaker 1 16:49

Now I am I'm just really thankful that I kind of embraced marketing. And there were some steps along the way. Like I tried to go back into legal, I tried to do like a bit of contract law where I got um, there was an opportunity where you would just be like the and it every time I would try, I'd be like, oh my gosh, you know, but it was always this idea, this idea that I can make more money doing this thing and just this fun thing put it on the side. But then at some point, um, I kind of just started letting it go and just really enjoyed the process and then realized that, oh, guess what? You can make money as a marketer as well. And so now I've worked in corporate where I am, you know, I'm working full-time and I'm an employee. And I've also worked as um, you know, with my own business. And it's been so great because as a marketer, I find that I get paid to be creative, which is the most fun thing for me. Like I just get paid to come up with ideas and execute those ideas. I get like I'm like, this is amazing. I get to do this. So um it just it just lights me up. And then now with my daughter's brand that we're working on together, I get to also use those skills and support her and just set her up for success with anything that she wants to do.

Speaker 18:16

Oh, so that's so awesome. That's such a great story. And I and I can't wait to get to the pot like why am I struggling with that? I told you I was like like I needed to exercise my words today. Pocket links. Got it, right? Um, I can't wait to talk about that more. But I would kind of want to just mirror back to you in my own experience. I, you know, have I have a master's degree in human resources development. And um and I worked in that field for 10 years. And and there were parts of it that were fantastic, and then there were there was a lot of minutiae also. And um, you know, towards the end of my career uh in that area, I had become it was it was actually um, gosh, right before you got out of school, um, when our company was downsizing regularly. And guess what the HR person gets to do? I was the terminator for a year. No fun. Nobody wanted to see you come into the room, right? And that is so not me. I was a trainer and uh, you know, personal growth and you know, let's develop you for your for your succession plan, you know, all this stuff. And then all of a sudden, nope, that's not the role we need for you anymore. You you are HR, so this is for you. So anyway, I I I kind of just when I had my daughter, I was like, uh leave. I'm like, I'm I'm not, I'm just not coming back, you know, and that was that's a scary thing to say. I have all this education and even experience now, and I'm making, you know, significant income that makes a difference for our household, but I am not whole. I am feeling, I hate every minute of it. So go and again, it took me a few years to muddle through it, but I found a very creative um way to express and earn as well. So I feel it, I get it, and I I respect your journey. But I do want to talk about your pocket pocket pocketlings.

Speaker 1 20:16

Pocketlings. But you know, before we go there, I wanted to talk about what was it about having your daughter that made you was it just you had more time because you were on maternity leave, or what was it about it that you're just like, you know what, I'm not coming back?

Speaker 20:33

Yeah, that's a great question. So I mean, I came home for leave for you know a number of of I can't actually like a month because I had reasons we won't go into here. But um it was just like I took a breath and and realized how that my internally that was not good for me in that environment. It wasn't who I was, and I I just dreaded going back and dreaded and dreaded, and you know, and it probably, you know, having a child absolutely changes you. I mean, everybody says your life's gonna change, right? But you have no idea once you bring home that baby, how your priorities are completely different. And although money is always gonna be a factor and important because you need to, you know, live and you need money to live, um, your priorities shift around so much. So definitely I'd say that that priority shift. How about you?

Speaker 1 21:32

Yeah, um, well, definitely having kids changed a lot of things for me as well. But I I was just curious about that, that pause. Like, because it's not easy, right? To decide that I'm not going back and I don't know what I'm going to do, but I just know what I'm not going to do because that can be so scary. Because you're just kind of like, let me just hold on to this thing. Oh, okay, while I'm holding on. Maybe I'll find something else. But sometimes that energy from that thing that you don't enjoy is so draining that you can't even find the other thing.

Speaker 22:08

So yeah, I think it's a matter, and maybe and correct me if I'm wrong. And for me anyway, uh, energetically speaking, it was turning away from what I didn't want anymore and look and looking towards what I did want and just trying to find my way that way. That's good.

Speaker 1 22:26

And I I think that makes a lot of sense because we spend a lot of time focused on what we don't want, not realizing that the more we focus on it and think about it and talk about it, the more we keep attracting that same thing. So I think that makes a lot of sense.

Pocketlings Dolls, Books, And Kid Business

Speaker 22:41

That is the truth. That is so tell us about the business with your daughter and how that started. And um, that's just uh it's just a beautiful story and something that you uh a legacy you're creating for your family.

Speaker 1 22:54

Yes, it's so exciting. So my daughter, uh, she was around 10 at the time. She was getting ready for her 10th birthday, and she was coming up with her list. You know how these kids come up with lists, and she wanted a plush doll, but she wanted a brown plush doll, and she couldn't really find them. Um, so she was just kind of like researching and researching, and she couldn't find them. She's like, you know what? I'm gonna make them and I'm gonna sell them so other kids have access to them and they're not searching like I am. And I was like, oh, that's amazing. How are we gonna do this? Because I don't seem, you know, like what's gonna happen. So um I wanted to also know that she was actually serious about this because you know, everyone has ideas, but it takes work to get stuff done. So I I tasked her with like, go do some research. What does the market look like? Do people even like plush dolls? Um uh I said, if we could find a manufacturer, then great, we can do it because I'm not gonna take a you know, thread a needle and figure this out. So, you know, so she did the research and then she did a presentation to the extended family via Zoom, and she just kind of talked about it, and then I supported her with some data and stuff like that. And everyone was like, Yeah, we love you to both support you. Um, and so we were like, okay, let's create a prototype. She designed the dolls, she drew them, we sent it to the manufacturing company, sent them a little bit of money. They sent us a prototype, and then we had some feedback, some adjustments, and then they sent us the final dolls and we started selling them. And in between that, my daughter and I started working on some books together. Um, and we started selling the books. We have an affirmation book. Um, the books are pretty much themed around affirmation and just like you're awesome. And so we started out with the ABC for awesome me, and you're learning your alphabet, but it's like A, I am adored. And so parents and um and teachers love it because they read it to the kids and then the kids start reciting it to themselves later. And so it's always it's so fun, right? It's like I am adored, I'm brave, and it's it's amazing. So um we really like that. We started going to vendor events, then we got some grants, and so that was really fun so that we could keep going. Of course, we had some hiccups along the way because all the tariffs and stuff really changed a lot of the plans and um all our like uh cash flow projections changed because of tariffs. So that was interesting, but the grants really helped us with just kind of continuing despite some of those fluctuations. Um, and so that's what we've been doing. And what we've also started doing is now we're doing some entrepreneurship trainings with the library, with community groups, and we train kids on starting their own businesses. Um, and they're around the same age as my daughter. So it's been a lot of fun. It's just, it's just so nice to be able to use a skill that you've developed to support your child and just let her know something that I didn't know when I was her age, which is you can make a living doing what you love. And so this is something she loves designing and drawing. So she gets to do that. Um, and we're in the middle of launching our new book, which is a um a period tracking journal for tweens. And I'm really excited about it because some of those things I learned in my 30s, um, just about like you have a cycle, and yes, you know, there's a wide range of what cycles can look like, but if you track your own, then you know what your cycle can look like. So that's been fun, just being able to come up with ideas like that together and just execute together.

Speaker 26:42

Brilliant, Osayi. Wonderful. And you are actually, you and your daughter together are changing the world, making it a better place. So thank you for that. How do we find how do we find you? How does you know everyone out here find you and and your um your books and your dolls and all that good stuff?

Speaker 1 27:00

Yes. So for the dolls, you can go to our website, pocketlings.com with the S. I say that it's my 11-year-old CEO. She picked the name, she picked the logo, she picked, she did everything. So I'm just here, you know, uh supporting her and just helping her with her strategy. So you can go to pocketlings.com and you'll learn more about the dolls and the books. And then personally about me, you can go to my website, osaelasti.com. And if you just wanted to have a conversation, you can book a call, osailastici.com slash focus.

Investing In Joy And Staying Connected

Speaker 27:35

Awesome. And I will put all of your information in the show notes. So everyone out there, you can find it easy with an easy click. Awesome. Thank you. So do you have any words of wisdom to the women out to the woman out here that might be in a situation where she has to make a 180 switch or she or she's she's contemplating it and she's afraid. What what what words of wisdom would you give her?

Speaker 1 27:59

I would say that fear is normal. So just remember that it's okay to be afraid because you're going into the unknown. That was one of the biggest things where it's like, if I'm afraid, then maybe it's not a good idea. But fear is normal because you're trying something new. But the most important thing is that your life is so valuable, it's too valuable for you to just invest your time being miserable. When you can invest your time and enjoy your life, enjoy all the things that you get to do. So, my thing is investing in your joy is really important in an exponential way. So whenever you get the opportunity to do, to do that, to reassess where you are, remember that your joy is valuable. So invest in your joy.

Speaker 28:52

That's great. I love um that you mentioned fear is normal because it absolutely is. It's a part of life. And I heard an acronym once um, fear is false evidence appearing real. Right? We imagine all the worst case scenarios and we worry about it. Um but in that flip the switch on that and imagine the best things and move towards it. So thank you for sharing that. So um, Osayi, I wrap up all of my podcasts with a question. How do you tribe? And it's about your closest circle of friendship. How do you stay connected? What kind of rituals do you have?

Speaker 1 29:34

Um, what has worked for me over the years, because I have lived in so many different places, has been something as simple as WhatsApp. So just saying hello, how are you doing, being in WhatsApp groups and just sometimes we're in life groups where we're like, okay, we're gonna build muscle together or we're going to tighten up our eating together, or something like that. But I'd say those communication tools have been so helpful because we might not talk for years, but then when we reconnect, it's so it's so powerful. And I found that it's something that has really gotten me through a lot of really challenging times in my life, just being able to say hello. I might not say anything, but just say hello and somebody's there, like I love you, you know, that kind of thing. And just realizing that there are people here that love you, that that miss you and you're here for a reason. And so do your best to just keep enjoying it. And so um, I'm so thankful that I get that opportunity where people just reach out to me. And um, I always say I live in Canada now, so winter is gonna be particularly tough because people stay indoors and they're in their own homes and you might not see people, but when they reach out with a call or a text message, it's always so much more meaningful. And then summer times we just run around and we have fun and we have a lot of play dates.

Speaker 31:05

Right. You have to be intentional. You have to, you know, it's just not going to happen organically. You have to be the one to reach out as well, right? And keep those connections alive. So thank you, Osaya. Really enjoyed our conversation. I think it's very meaningful to our audience to hear your story about you know the very professional track of the midlife crisis of the smoke source. I like to finish with the last line of my book, and with you and myself and the listener, when three or more gather, we are tribe. Thank you so much for being here, Osayi. And thank you, listeners, for tuning in. And I can't wait to see you next time. Thank you for spending this time with your lady tribe. I always say that when three or more gather, we are tribe. And today, with my guests, myself, and you listening in, that circle is complete. I hope this story reminded you that your purpose is worth the pursuit. If this episode stirs something in you, please take a moment to subscribe, like, and leave a comment. Your engagement helps other sisters find their way to our circle. If you're ready to take the next step in your own transformation, I invite you to join our gathering place, the Save the World Sister hood Facebook Group. It's where we unmask, connect, and cheer each other on as we ignite our lives together. Until next time, I'm Brenda Ridgley. Save the world sister.