Who Are You When The Boxes Run Out

You can do everything “right” and still feel lost when the boxes run out. That’s the moment we dig into with Sheree Holt, founder of Why Not Rome, a boutique travel brand created for midlife women who crave culture, community, and real connection. Sheree’s path moves from performer to corporate leadership, then straight into the midlife funk that hits when success stops feeling like you.

We talk about the identity shift so many women over 40 experience but rarely name: the gap between who you’ve been and who you’re becoming. Sheree shares what it felt like to leave an unfulfilling job without a perfect plan, how fear and control show up during a career pivot, and why waiting for a single “big epiphany” often keeps us stuck. The real breakthrough, she says, comes from small actions that disrupt routine: new rooms, new people, new choices that slowly reveal what fits.

You’ll also hear practical midlife reinvention tips you can start this week, including how to name your biggest pain points, stop spiraling into self-diagnosis, and use simple tools like journaling and tiny goals to rebuild momentum. Sheree also points you to her free Midlife Playbook so you can create your own next chapter with intention.

If you feel that quiet restlessness creeping in, listen now, then share this with a friend who needs it. Subscribe, leave a review, and come connect with us in the Save the World Sisterhood Facebook group.

Ways to Connect with Sheree:
Personal site:  www.sheree-monique.com
Company:  www.whynotroam.com

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Transcript

Midlife Reinvention Season Kickoff

Speaker 1 0:00

Hey everybody, welcome to the Find Your Lady Tribe podcast. Wow, this season is so incredible. It's all about midlife reinvention and all of the awesomeness that we are becoming as midlife and beyond women because we aren't done yet. And I'm particularly excited to share with you Sheree today. Her story is fantastic. I want to tell you about Sheree Holt. She is the founder of the Why Not Rome Company. Is that right, Sheree? That is correct. It's a travel brand for midlifers. Absolutely, a boutique travel brand, born from her own midlifer reinvention and designed for mature travelers seeking culture, community, and connection. You're my people, Sheree. A creative entrepreneur and lifelong traveler, she stepped away from a successful but unfulfilling corporate path to pursue a life that felt more aligned and authentic. Through both her businesses and personal platforms, she encourages women to rethink what's possible, reconnect with what moves them, and create a life that reflects who they are now. Welcome, Sheree. I'm so glad you're here. Thank you. Thank you for having me. I appreciate it. Welcome to the Find Your Lady Tribe Podcast. I'm your host, Brenda Ridgley. This is season four. 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. Okay, so Sheree, let's just get started from the middle. All right. Kind of the middle. I want to hear your story. So don't leave anything out. Uh we want to hear uh where you started and kind of your the process that you went through to get to where you are now. And just give us the funk. Sure. So I was born on a little farm.

Speaker 2:20

No, I'm I'm kidding. Um I have um pivoted many times in my life, but I was a theater kid. I grew up, um, did that for a decade or so as a professional performing artist, moved into my 30s um and transitioned into business. And that's kind of that set the stage for my midlife reinvention, which, you know, I knew at the time as a crisis. I've been this creative performer. I kind of grew up a little bit, got a little more mature, I got into business, and then I started to kind of ascend the levels. I got into senior leadership and HR, and I'm like end of my 30s, and I'm like, okay, I've done the things. Now, what's important to understand about me is that I'm a box checker. Very few things please me more than setting out to do a thing, writing it out on my whiteboard, and then checking that box. All through my 30s, I'm checking boxes, checking boxes, checking boxes. I bought the house. I drive the car I want, I'm taking my trips because I love to travel, I'm doing all of the things. Um, hit 40 right before my 40th birthday. I said, you know what? I need a husband. So let me go check that box. And I go out and I go through the painful process of dating and I find my husband. And then the 40s came, and all the boxes were checked. Not that I was just like some multimillionaire just living, you know, a blissful life, but I had a good life. And there were no more boxes to check. And I didn't have every single thing that I wanted, but I absolutely had everything that I needed. And I there was a silence that I was uncomfortable with because I'm always moving and shaking and checking the boxes. And I felt lost for a second, and then the lostness turned into sadness, and then the sadness turned into confusion. Because if I'm not all the things that I've prided myself on becoming and being, if I'm no longer those things, then who am I?

Speaker 1 4:30

And I love this. Sheree, can I just um talk more about the box checking? Have you ever gone and done something and then checked it off? I mean, then like written it in your book and then checked it off. I am guilty because I'm a box checker too. And I get it. I totally it's satisfying to okay, visually see because a lot of times we're like doing all these different wild things, and you go, What did I get done at the end of the day? But if you like have these boxes to check, that's just feels so good.

Speaker 4:58

It's so uniquely satisfying. And like you said, I've done the thing, didn't even have a box for it, but I'll go back and be like, Nope, we're gonna, because I want my credit for checking the box. Absolutely. Yeah, yeah.

Speaker 1 5:12

And then and then going through I I get it, all the boxes, you know, all the life pivotal moments that you're like, okay, done, dun, dun, dun, done. And then when you get to the point where you don't really know what the next box is, or you're like, what I did it. Uh you fell into this you know, fla floundering, you know, period is kind of what I'm hearing.

Quitting The Job Without A Plan

Speaker 5:34

Yeah. It was a funk, and I did not know, it was unlike any I'd ever been through before. Like I'd been through not getting the thing that I wanted or having to work extra hard to push myself to achieve something, but to just be like, what is there? I don't know what I'm supposed to do now, was very, very new territory for me that came with a mix of emotions, including guilt. Because when you have the things that you prayed for, how dare you be ungrateful for the things? What do you mean you're not you're you're not fulfilled? Fulfillment. There are people out here who are praying for what you have right now. So then there was that too. Yes. And I had to get really still to figure it out. I was like, I don't know what I'm supposed to do, but I know that sitting here every day rehashing it and stewing in it is not doing me any good. And so I was at a point where, you know, I'm doing well in my job, I'm making good money, but it was just increasingly annoying me on a daily basis. And I'm getting this nag, like, leave that job, quit your job. And I'm like, what do you mean, quit your job? Who's giving up the like and do what? Like because I didn't have the next step, I refused to do it. But the feeling became so strong that I said, okay, I'm going to obey this voice and I'm gonna go ahead and quit my job. So I go, I think about my how I'm gonna say it. And I say, you know, I'm gonna write my my letter, I'm gonna send it to my my manager, and boom, woke up that morning, sent the letter, boom. Now, let me sidebar this by saying, I'm a firm believer that the universe will give you the same lesson repeatedly until you get it. So I the morning comes in, I log in, I send my letter some relief, but also scared, like, okay, boom. You know, this is it. I'm leaving my job. I don't know what I just did, I don't know what I'm going to do next, but I'm done. So instead of a reply, I got a meeting on my calendar. And by the end of that meeting, I was like, okay, well, I I need, you know, I guess I could stick around a little longer. So I didn't, I didn't quite listen.

Speaker 1 7:50

Someone else's some what someone else wanted you to be who they wanted you to be.

Speaker 7:55

Right. So I was like, all right, well, you know, I mean, they didn't tell me to kick rock, so they must really want me here. And it's a little toxic and a little unfulfilling, but I'm gonna I'm gonna power through. And that was earlier in the year, and then by the end of the year, we were back in the same place. The lesson came around again. I was like, I got it this time, done. Um, and then started the process of the reinvention. So silence, confusion, sadness, a little anger, because it's like I worked too hard to not, you know, know what I'm going to do next.

Speaker 1 8:27

Um, maybe a little fear.

Speaker 8:29

Did you have any fear? A little fear. I felt like I got married late. I didn't get married till I was 40. So I was thankful that I had my husband to kind of pick up the slack. And he's always been very supportive. Like, do he? I'm a person that I have to think 10 steps ahead. Like, I like to know, okay, I'm at the edge of this cliff. There's a few things that could happen. I could get, I could rappel down, I could fall off. I could like I would literally go through those motions and say, these are all the possibilities that could be the result of me standing on this cliff. Whereas my husband's like, you're gonna jump? You get like it's very black or white for him. So he's like, if you don't, if you don't like your job, quit it. If you don't like your life, change it. Like it's very, very simple for him. And I'm like, okay, but that's not really how I work. Um, so yes, I was fearful, but I said, you know what, I'm just gonna get still and try to figure it out.

Speaker 1 9:18

And what about let me just ask about your identity? How much of your identity was in that role for as your this go-getting high very successful professional?

Action Prompts That Create Clarity

Speaker 9:29

I I would say a lot at that point. And and that was a big transition from me being a creative, um, from being a person who's toured the world, who's been a union theater actress. And what so my identity early on was I'm an artist, I'm, you know, I'm an actress, I'm, you know, these things. And then, and then I was until I wasn't. And that was a hard transition, but I felt like I was a little more, I was younger, I was more like there's more to explore, you know. But when you do it, when you're 40-ish plus, um you wonder what opportunities maybe the world isn't exactly my oyster at this, at this age. Can I afford to take these types of risks at this point? Um, I've worked so hard to get to this place. If I fail or don't reach what I want, will I ever get back here again? And will I regret it? So all of those things. And I sat for a while and I felt like after a while, I was like, oh, well, this is kind of cool. I can wake up, I can do what I want. I can, you know, for maybe like a couple weeks, I said, I could be a housewife. This is this is good. I'm watching my shows, I'm doing the things, and then I was like, but but what? Um, and so I really had to come up with a a formula for how am I gonna move myself out of this ambiguity? And I decided that it was action. And I was like, what action? Any action, anything that I don't normally do, any place that I don't normally go, any people I don't normally hang out with, that's what I'm gonna do until something clicks for me. So I'm out at networking events, I'm out and I'm I'm like an introverted extrovert. I'm very much a people person, but it's conditional. Like I gotta feel like it. I gotta, so I would push myself several times a month. I'm out, I'm networking, I'm meeting people, I'm going to women's groups, I'm joining Facebook, I'm doing all these things to try to get a spark. I went to a woman's brunch with a bunch of strangers. There were probably about 15 of us at this nice brunch place, and we were all at a round table, and everybody starts to introduce themselves and say what they did for a living. So as I'm a maybe, I'm maybe the seventh person, I'm in the middle of this table. But so she's like, Oh, we're just gonna introduce ourselves. And I just thought they were gonna be like, Hey, I'm Jesse. Nice to meet, I'm from this part of town, nice to meet everybody. But people started to like list their hi, I'm you know, I'm Jennifer and I, you know, do this, and I and I'm like, What am I gonna say? Hi, I'm Sheree, and I'm unemployed. Didn't quite sound right. It didn't quite sound like the thing to say. So I've been bouncing some ideas around in my head. Um, but when it comes to me, I literally say, I mean, I mentioned, yeah, you know, I've I've you know been in HR consulting for a while and you know, whatever. I was like, but I'm starting a travel brand for midlife, um, midlife travelers, or however, I don't know how I phrased it at the time, but it just came out of my mouth. Like I had never said that to anybody. I never, but it just kind of flowed at the moment. And so everybody else goes around the table. I leave that lunch and I go home and I start thinking. And I'm like, okay, how can I take what I have? Because I'm not starting. I had colleagues who had gone who were burned out from HR, um, because HR can do that to you. And they like literally started nursing school, like start it from ground zero. And I was like, wow, I don't have that kind of tenacity. So I'm like, what can I? I don't, just to be honest. I was like, I don't know. Yeah, like I don't have that page. I'm I'm a I'm an ambitious person, but I I can't do it. I'm like, you're sitting there with like science books. I at our age, I don't know how you do it. Um, but I was like, let me think about the skill sets that I have and how can I take what I have with what I love and merge those things together. And as I started to kind of just meditate and think on that, it just became clear. I started playing around with um logos and design. And I might have sent like four or five to my sister and my mom. I'm like, hey, I'm thinking of doing this travel thing. What do you think of these logos? They've weighed in. And um I started training, I started doing all these things, and I'm looking at names because you know, of course, you got to look at who what names are already out there business-wise. And everything I thought of, there's already a company that's kind of sounds like that or or looks like that. And I was just like, it just came to me. There's a whole wide world out there. Why not Rome? And I was like, hmm, I love it. Okay. And so that, and then once I latched on to that, then it was full. Then I actually had something to reach for again. And so that really just ignited a fire in me that I had that was missing for literally like a year and a half, two years.

Speaker 1 14:19

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. Yeah, I'm sorry. I love all of this, and I just kind of want to go back to what you shared about doing things differently and things you hadn't done before. What and that's basically getting out of your comfort zone. I'm an ambivert too. I know what you're talking about. Um, and it's it's it's a decision, not just because I want to go out and you know, network and meet new people and do things that are it's because some people are energized by that. Some people absolutely are. Yes, and you and I are not, but to do something uncomfortable uh gets you by doing that, you opened up all this world of opportunities that inspired you.

The Identity Gap In Your 40s

Speaker 15:20

Yes. Absolutely. And I think that there is a a there's like an identity lapse that I think happens to a lot of women, especially in their 40s, that we I just feel like it's not talked about enough. People talk about the perimenopause and they talk about the night sweats and all the things, but there's really, by the time you get to our age, you really latched on to an identity. Like you've established yourself. Some people are, you know, it's like I'm a mom, I'm an educator, I'm this, I'm that. Like, and you're really married to that because you've spent time. You there's this give and take, because in one way, um, you're so comfortable with who you've become and you're maybe have some pride in what you've accomplished and achieved. But then there's also like a little bit of a disconnect as your world starts to change, as you because there's like literally an awakening. You're like, that thing that my grandmother always told me is actually not true. That's an old wives tale, or that you know, this does nothing really breaks if I do this. So there's there's these little awakenings that happen, and you really start to break away from yourself. And in between there, there's a gap. And then you wonder why you're not happy or fulfilled. It's because you're still operating in the old version of you instead of really embracing who you're becoming. And I don't know what that I'm not a psychologist or social, I don't, but I don't know what that gap is called. Maybe someone has named it.

Speaker 1 16:49

You know what? Maybe we should call it something. Um, because I this has hit me a couple of times throughout your story because you're like you're I was I was becoming and I was becoming. And when you stopped becoming, you were like not unbecoming, but it was like, you know what I mean? It was like that growth and um vision. I don't know what we should we need to come up with a name for it.

Speaker 17:13

We need we got to come up with something. You're not you you're very very right, you're very correct. You're not unbecoming, but you're just there. And you have to be able to sit in the there for a second. And it's a it's the most uncomfortable seat I've ever sat in to just be there. Because how often can do we have the opportunity to just be? People have kids, they're like, I got a dog, a cat, a partridge, and a pear tree, my job, my like there's so much going on that even if you do have some free time, maybe you hit a concert or you do a date night with your spell or you know, whatever, but you don't how often do you just have time to just be? And so when that stillness comes, especially if it's unplanned, it's very uncomfortable to sit in because you're like, okay, uh I'm supposed to know something, but you just gotta wait on it. And then you've got to give yourself action prompts so that you can begin to move out of it. It takes a little time, took me some time. I don't know, you know, for anybody else, but it took me a little time um to to get there. But once I started doing something, those little somethings were the steps. Yes, baby steps, yes, the baby steps that planted the seas. And I think what I was waiting for was the big bang, like the epiphany, like I'm gonna go. Like, I love Oprah. Oprah's like, sit in the stillness amongst the nature. And I thought like an acorn was gonna hit me on the head, and I was gonna be like, Bam, there it is. And it was not like that at all. It was a lot of little things that led me to, okay, this is what the next chapter looks like. This is what's possible. When I thought everything was done and I checked all the boxes, and I did for that chapter. Now I took the step where there was no visible, you know, floor. And as I started to do that, the seed, the some things started to plant the seeds for the next steps. And now I'm okay. That I don't I don't I'm not a fortune teller. I don't have to know everything that's gonna happen. I'm still cautious by nature. I'm still a little bit, I'm a little bit of a recovering control freak by nature, but I'm much more comfortable with saying, you know what? Whatever's gonna be is gonna be. But I do have some control over, I don't have control over outcomes, but I have control over my emotions. I have control over my attitude, I have control over um, you know, my mood when I get up and how I set my day. And so once I embrace that, I was off to the races.

Speaker 1 19:46

And you have control of how you read the signs that come to you, because that's definitely could go either way a lot of times, right?

Speaker 19:52

Either way, overthinking, overanalyzing, um, worrying about what other people think, which is the thing for a lot of people, and even for I'm a pretty confident person, but you know, I because I'm so um just prone to think out everything, I'm like, okay, well, if I say this and I do this, who's that gonna affect? How might that blow back on me? How might it be misinterpreted? But you can't be all the things to all the people all the time. All you can do is be yourself. And when you approach anything earnestly, um I think people get it. Some people will just always be intent on misunderstanding you or twisting your words, or you know, what those aren't the people. Um, so the other thing part of that is just finding your people and and not mourning the loss of the people that are left behind, because that's another thing that happens. Um you shed some people along the way as you're becoming the newest version of yourself, right?

Speaker 1 20:50

And how they react to you is not about you at all. When you really when you realize that it's really all about them, and that gives you a little peace, and you I can leave them where they are. That's their choice. Um, so I want to just I would I just love how your inspired thought came to you. Really, it just you can't you can't even say where it came, it just flowed out of you. So go and you started to, but go from there to like today. Let's hear it.

Fast Start Tips And The Midlife Playbook

Speaker 21:22

So after a while, um I really became comfortable. I'm like, you know what? I wouldn't have been given these ideas, these thoughts, these feelings if they if there wasn't something to it. So today I'm comfortable in who I am, I'm comfortable in what I'm doing. Um, I can't see the full picture of where it's going to go, but I started my company two years ago and um it's thriving, not in all the ways that it could thrive, but it really got an amazing start the first couple of years. Um I became okay. With people not initially clapping for me. Not that I necessarily needed it, but it would have been nice. You know, when you kind of break apart from the herd a little bit and you start to do something, or you do things that people aren't used to seeing you do, or you're becoming somebody that people aren't quite as familiar with. It can invoke a lot of feelings. Not necessarily and people will automatically say, oh, they're jealous of me. They're not supporting me. They're, you know, it's not always malicious. Sometimes you doing your thing reminds other people of what they're not doing or may not have the courage to do. And that makes them uncomfortable. And as you said, that has nothing to do with you. That's more them. So today I feel great. I feel great about what I'm building. I feel great about who I am. And I really am focused at this point on spreading that to other people. Because you don't have to be it doesn't have to be a crisis. And I think if we I think about what, you know, I I joke with my mom when I started Perimenopause. I was like, why would you not tell me about this? Like, what? You didn't tell me I was gonna sweat through my sheets at night. Like, and she's just like, well, you know, it was different in my day, you know. And I'm just like, how helpful would it have been for me to know to just I thought I was dying? Like, I was like, what? I need an EKG. Like my heart, like what is going on? So I think it's helpful. Um, a lot of times we get on the internet, people in general, I think it do a lot of things that are so that they say is in the name of helping people, but it's more for clicks and likes and attention. And I'm not that kind of person at all. I got plenty of that as a as a performer, but genuinely connecting and finding my tribe, so to speak, um, and connecting with like-minded people who are about the business of just living well, living your best life, which sounds cliche, but it's really true. Like I'm really, I just want to live well and be happy and do good things in the world. There's enough sensationalism, enough all the other things. Um, so finding my tribe and cultivating my tribe has been like a really just fun, fulfilling thing for me in this, in this time, in this space in my life. Oh, I love it.

Speaker 1 24:21

So, Sheree, tell us and the listeners especially, like maybe one or two or three, you know, fast start tips, like if they're going through a funk or questioning or afraid, um, and they are they're they're in that floundering phase. Yeah, uh, what what tips do you have for them to kind of make shift that they could start today or this week to kind of start moving them, take taking those baby steps?

Speaker 24:49

Absolutely. So first acknowledge it. You're not going crazy, you're not necessarily depressed. Um, don't be so quick to doctor WebMD yourself and and self-diagnose. It's a change. You're going through a transition. Um, so and I actually wrote a little uh it's called the Midlife Playbook. It's a freebie on my website. Um, that kind of gives you some steps, some actions that you could take. So acknowledge it, feel it, know it, and know it's not gonna last always. Second, identify your biggest pain points. Like is it that I don't have enough time? Or you might know something that you want to pursue or do, but you don't have the time, or you might have no clue at all. Just figure out like what's the what's what's the first or second thing that if I could do, I would do. So once you acknowledge that thing, and then do something, do anything is what I say. Not nothing crazy, but do anything. Um, start to deviate from your pattern because in at our age, we love, we love our patterns, we love our routines, we love, you know, I get the kids up, I give them their cereal, I we love that. You gotta start shaking stuff up and action really disrupts routine and monotony. And so once you start doing those things, um and start writing things down, put it on paper, get a little lined journal, um, get a whiteboard. I've got a whiteboard in here, um, and just start sketching some things out, whatever comes to your mind and break up the monotony and then take tiny baby steps towards one goal. You don't have to do it, you don't have to fix your life, you know, in one in one fell swoop, but you can begin to make little changes that will um spark inspiration and or um just help to to improve your mood and help you to feel better.

Speaker 1 26:38

Right. Great advice, Sheree. Awesome. So, how do we all find you? And I heard about a freebie.

Speaker 26:46

How do we get that? Yeah, so my personal website is shere monique.com. It's s-e-r-e-e, hyphenmonique, m-n-i-qu-u e dot com. And the midlife playbook is right there, front and center. As soon as you log on, you can click that and download it and uh and start your own your own journey.

How To Tribe And Closing Calls

Speaker 1 27:04

Awesome. Awesome, absolutely. And I will put that link in the show notes, everyone. So if you're driving, just come back and and you can click right on it. That's awesome. So uh let's see. You know, I always wrap up every podcast with the same question, and it is Sheree, how do you tribe?

Speaker 27:25

I meet people where they are. Um, I have several close friends, none of whom are close to me. They're all kind of spread out around the world. Um, but I think we meet each other where we are. We're intentional. Um, we show up for each other when we need to, um, or even when someone doesn't want us to, but we know it's needed. Um, but yeah, I just meet I don't, I don't project, I don't um assume, I don't judge. I think we just meet each other where we are. We realize that, hey, we've come this far. A lot of people have not made it this far in life, but we're here and we've got each other, and we're gonna think the best about each other, and we're gonna support each other um as much as we can and do our best to help each other get through this thing called life. It's all you can do.

Speaker 1 28:14

Yes, absolutely. That's fabulous. Well, Sheree, it's been such a pleasure having you on, and I love your story, and I love where you've taken your midlife funk into this helping women all over the world explore. And uh and you guys go to her website, find out more about what she's doing for women, and get that freebie, uh that midlife checklist. I'm gonna I'm gonna do it myself because you gotta keep learning, right?

Speaker 28:42

You gotta keep learning. Thank you so much, Brenda. I appreciate it.

Speaker 1 28:46

Absolutely. And and ladies out there, if you have a friend that this any that you thought of during this conversation, please share this with him. That's how that's how we we help each other. We help the sisterhood by sharing this kind of good stuff with each other and grow this sisterhood. So, with that, um, when three or more gather, we are tribe. 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 stirred 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 Sisterhood 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.