Why Dating Yourself After Divorce Changes Everything

Jennifer McCullough, a Midlife Brilliance Coach, shares how three divorces led her to develop a nervous-system-focused coaching approach. She recommends "dating yourself" as a practice to rebuild worth and establish boundaries, treating self-care as trauma release rather than surface wellness.
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Hello, heroines, and welcome back again for another interview. Today I have the lovely Jennifer McCullough. Welcome! How are you?
Thank you, I am fantastic. I'm happy to be here.
You look like you have fabulous weather, so you can't go wrong with that.
I can't go wrong. Short sleeves, feeling good, not sweating. I'm ready for it.
Awesome, that works. Anytime we're not sweating, that works. So, um, let's just get started super easy. Why don't you tell us where you're from and what you do?
I live in Minneapolis, well, just west of Minneapolis. I've been here for over half of my adult life, so we can call that home. And I am in probably my third encore career as a Midlife Brilliance Coach. I help women in midlife reconnect or connect, depending on how their life has gone, to their brilliance.
I want to hear more about that because midlife brilliance sounds just Brilliant. So tell us a little bit, like, kind of what was your journey? How did you— how did you— because you talked about 3 stages, right? So kind of take us through your story a little bit.
Yeah, sure. So I, uh, growing up, um, in the late 1900s, as my daughters like to say, did the go to graduate high school, do some college, get a job, rise up in the job, have a career. And it was a 24-year career, and I liked the first 18 years. And after that, I thought, I gotta do something else. What am I gonna do? I got certified as a coach. And what catapulted me out of that job actually was the death of my younger brother, because he had always told me that you're meant for more than this corporate thing. And when he died, and he's younger, was younger, I was like, "Oh, I guess you don't get all the time." So I just left that job with a coaching certificate and thought, "I'll just do my own. I'll do my own business. It'll be powerful. I'll change the world." Look back on that now and I think, you know, in the depths of grief, maybe isn't the time to start a business. So I got about 9 months into that endeavor and gave up on myself. And so I took another job, and it was coaching, so it was much more in line with what I was heading for and wanted to do. And it was a fantastic experience as far as I am leagues above skill-wise and experience-wise as where I was when I started originally. Um, but that lasted 5 years, and the first 2 were good. So then I left that last fall, and now I'm doing my own business. So Phase 3, 3 times. We're going to do it this time.
That's— and I love that. And I love it for a couple of reasons. One is that, you know, you kind of— you did what society expects us to do, right? You get the degree, you go into corporate and you climb the ladder, you do all those things until you get to the point where you're like, maybe there's more to it than that, right? Yeah.
Yeah.
That's where I was after 30. It took me 30 years. It took me a little longer than you.
It took me 30 for real. I did 20.
That's true, because between a 1 and 2.
Yeah.
And, um, but also because you decided to take control of your life and be reliant on, on yourself. So how did that feel in the beginning? Like, I'm thinking about our heroines in the group who might be in a place where they kind of have to start over after, you know, heartbreak. So What was that like for you?
Well, and in the middle of that story, I also was married and divorced 3 times. So the last— I'll talk about the last one because it was probably the most impactful. I was in, uh, leaving my corporate career, recognizing the end of a marriage that had gone on for way too long. And I'll just tell you, the year that that was happening was in like 2019 heading into 2020. And so then I jumped into like, oh, we're having a pandemic and I have these two daughters and terrifying is a word I'll use really honestly, not just the pandemic, but the idea that I didn't have a safety net that I'll say to anyone who's still in the area that I was, there is no safety net there either, but there's a perception of a safety net. So it was, it was really It was scary. It was exhilarating. It was— there were moments when I felt like I was on top of the world and other times when I was curled up in a fetal position. And that carries forth. Like, I've cried today already, but I'm also really excited about what I'm doing in the world.
So tell us what you're excited about.
Well, I'm excited because I see having gone through it, what I want to say, the hard— I know there's harder things, but the hard way, having done this journey from the matrix or whatever into where I am now, I feel like I can shine a light for other women. So it doesn't have to be as hard. I don't claim that it'll ever be easy, but it doesn't have to be as hard as when you're doing it alone. And so I'm so excited because I think No, I don't think, I know that it's up to women at this juncture in our world, in our planet, in our country to change it. And what I also know is that women who are in their trauma, in their stuckness, in their pain aren't going to be able to do that as much as if they're healed and light. And so I can help with that. That's where I come in. I want to help so many women to shake off the shackles, to shed whatever they need to shed, to shine their light, because we all have one. And if I can just say, I think the men have been in charge for a long time, and we see where we are. We are— it's our time, and I want to be part of helping. I can't do it just one, obviously, so I want to help so many other women to find their way to their brilliance and let it shine.
So can I get a fist bump on that? Because I think you and I then can do it together because that is absolutely the same mission that I'm on. Yeah, I feel like, you know, when I think about the past, and when I say the past, I'm talking the distant past, women used to be revered. Majora's Garden used to be— exactly, they were the oracle that men went to them for counsel. Society went to them for counsel, and somewhere along the way things got topsy-turvy. And there's a place for men, there's a place for women, and there's a place for our collective energies to move things in, in a positive way. So yes, when, when you talk about helping women find their brilliance and shine from their brilliance, what does that really look like?
What does it look like for the woman, or what does it look like for the work that I do?
For the, for the women, what's the transformation that they experience?
The transformation, I'm going to really simplify it, it's from burnout to brilliance. It's from the nervous system that is fried, it's from the confidence that is gone, it's from the physical body that is failing. And I'm going to say most of us are either peri or post menopause. It's from that place of just like, I took care of everyone my whole life, I'm falling apart to pieces, and there's no one to take care of me. And I'm like, yes, there is, and let's do it. Yeah.
And it starts with us taking care of ourselves.
It does. Yeah.
Because that's, that's what I found also when I came out of my marriage. I was like, I had given so much, it was like pouring from their proverbial empty bucket, right?
It was, it was very much like that. I, when I, in 2020, I forget which year, this is funny because it's a big deal, but I published a book called Self-Care for Your Apocalypse. And I published it, I wrote it because as I was working with women, they, I would say, what's your self-care like? And self-care, even to this day, has like, I feel like that word because it feels so trendy or unattainable or something. But anyway, I would ask, what's your self-care? And across the board, I would hear, well, I try to eat well, I try to get enough sleep, and I exercise when I can. And I'm like, that is literally survival. But that's what we thought self-care was until we learned that self-care is everything that makes you better. And so the self-care is critical.
I agree. And I think self-care gets trivialized because people talk about self-care and it's the mani-pedis and the this and, you know, the, the kind of more— which are nice, and don't get me wrong, I love me a good mani-pedi. Yeah, but it goes so much deeper than that because part of it to me is addressing whatever triggers, whatever patterns inside us so that we can, like you said, shine our brilliance.
It's with the healing. It's the healing, which is so mucky and so sludgy sometimes and so time-consuming— without that, I don't think we can truly take care of ourselves. And it's not really encouraged, allowed. It is more and more now, but if you're in the matrix, it's not. And so the healing, I think, like when you cut your finger, you get a Band-Aid. So when you have all these years of trauma that is stacked and stacked and stacked. We've got to help people unstack that and get it out.
Yeah, because holding on to it certainly doesn't do us any favors. None whatsoever. So how do you work then with a woman who comes to you with burnouts? Take us a little bit through your process so that we can wrap our head around a little bit, like how you work with someone.
Yeah, the first thing that I do, and this is how I explain it when I'm talking to people, is you're not going to feel like much is happening, but a lot of foundational work is going to be going on in the background. So I'm working with them on their nervous system, I'm working with them on their rituals, which can become routines. I'm working on the healing piece of it. I'm working on getting— whether I'm doing the healing or whether I'm referring them to someone else to do it, We have to clear the path, like we're weeding, clearing the rocks out of the dirt before we plant a garden. So that's about, I wanna say it's at least 3 months, usually about 3 months before we, there's breakthroughs along the way. But maybe at 3 months we might start talking about goals and where do we wanna head? Because the goal that you come up with when you're burnt out is like, when I first started this work, my coach said, what is the best feeling you could have? And I said, peace of mind. And we want peace of mind, don't get me wrong, but now I'm like, joy, non, it has to be joy. But I wouldn't, I would have felt embarrassed to say joy in the beginning. So goals come 3 to 6 months in, and then we start action planning once that healing, caretaking of yourself, once that is more of a routine, it's not a habit yet, but it's routine. And then what do you want? We're gonna get there.
Yeah, and I love that because it's digestible steps, right? Because the image that came to my mind and the saying is, how do you eat an elephant?
Yeah, one bite at a time, right? Yeah, exactly.
Sometimes the stuff that we have to deal with and the stuff that we have to release feels like that elephant, and trying to do that on our own can feel even more difficult.
I don't know how many of us do it on our own without help. I think that it takes, it takes us a team. It doesn't have to be a team you pay, but it takes a team of people. You, you have to have people that let you know and keep reminding you that you deserve it, because that's not something that we have conditioned in a state of burnout. We don't Even I'll ask people, women, like, what, what do you like? Nobody knows. I didn't know. Why would you know? You've never done anything for yourself. So it's like very much getting to the basics of seeing yourself as a human being that deserves care first, and then the world unfolds from there.
Yeah, and it's, it's funny to hear you say that because it's like, not only do we not know, but we've never been asked, so we've never stopped to think. What is it that I really want? And I know there are exceptions, because I know some women who have lived by the tune of their own drums and have always done what they wanted first, and whoever was in their life was along for the ride if they wanted.
Yeah, right, sure.
But I think a lot of women, probably a bigger majority, are in that place of giving.
Yeah.
And serving, because that's what I think by and large society conditions us to do.
It is. From the time you're little.
Yeah.
Be good, do good. Don't make waves. It's not girls will be girls. That's not it. It's you are here to support everything that is. And so unlearning that takes a minute. And before you can unlearn it, you have to believe you deserve to unlearn it..
And before that, you have to be aware that you have a pattern that you need to—
Yeah, yeah, it's, it is so deep in all of us. And I keep thinking, oh, there's the crux of it. Like, when I got to the training on nervous system fitness and health, I was like, there it is. And I'm like, but nobody knows that, that their nervous system is what's causing all these problems. We call it burnout, we call it that. So that's where I landed on burnout as a word. I have really strong feelings about the fact that we are actually burnt out.
People, we are—
it's not our fault. We're not doing things not enough, not hard enough, not strong enough. It's not that. But burnout, everyone understands. It's your nervous system though. It's fried.
So, and it is the first place to start because without getting that stabilized and well adjusted Everything else is going to be done from a place of fight or flight.
It is, or overwhelm or freeze. It's from somewhere that is. And that's when I, back before I knew the nervous system work, I would work with women and we would just be repeat, repeat, repeat. We'd make big progress during session and then the week between, we'd get to the next week and I'd be like, we're doing the same thing. And not that I expect, but I saw a trend is what I saw. And so when I learned the nervous system, work, that's when I thought, okay, here's something that you don't have to think your way through. You don't have to know what's wrong logically. You can just start healing your body, and then we can make some things happen.
Yeah, I love that. I love that. So when you went through your divorce, um, what was your biggest lesson? Because I know it often can feel like this is a, you know, a crap thing that's happening to me, right? But there's— in every crap situation, there is good. Yeah. Um, so what was your good?
Um, talking about the last one, the good was that I was able to finally see a pattern in myself that stemmed from where they usually do, from my youth, that was allowing me to continue to get in relationships that were not healthy. And it took 3 divorces before I was like— because, you know, you're like, is it me? Yeah, it's you, it's you. So it was— I was able to identify the pattern and then do something about it. So that was the best part about it, um, and that I'm not married to him. I mean, that's really the best part, if I can just be honest.
But I hear you, I hear you.
Yeah, that part's over. I got to decorate my house real pretty, you know, but these are all fun things. But it was the pattern identification that was really the life changer.
Yeah, I can, I can see that, I can see that. So Just trying to think a little bit, um, is there anything that you think is important to mention, um, that would really serve our heroines but that we haven't talked about yet?
I think it is really, really mandatory, critical— I can't think of the strong enough word— but that before, after a divorce or after a breakup, before you do anything else, you date yourself. And you date yourself like you date a new person. You like get to know the person. You— what is that person like? Give it— you like, you date yourself. And that was, um, also life-changing for me. I started doing that in 2020, haven't stopped.
But it's a good thing.
Really good. What happens is, one, you learn a lot about yourself and what you like and what you need. And two, you begin to think you deserve things. And then you're much pickier about who you'll let in your life, be it romantically or any other relationship. You're much pickier, your standards are higher. And I mean, my life— I'm not saying it's perfect because I'm in the process of starting a new business and that's hard— but I, I feel valuable, I feel worthy, I feel like I matter, all that. And I like my life even though it's hard right now. Date yourself.
Yeah, agreed. Like, learn to be okay and more than okay with, with who you are, and learn to be okay with being alone.
Yeah, exactly. That was a— I mean, obviously 3 times I wasn't okay with being alone, but I wouldn't have said that to anyone. I would have been like, no, I'm highly independent. But now I'm like, if somebody doesn't actually add value to my life, they're not invited in.
And I love that you put it that way because it is an invitation and we get to choose who we invite, right? If it's— if our life is our birthday party, we get to say who comes in, right?
We get to say who comes in.
And it's no, no wedding crashers here.
No wedding crash here. No, nobody. And it should be people that make you like the way you feel better, not do they like me. Do I like me when I'm with this person?
They come in because they enhance you, not because they validate you, and that's a huge difference.
It's absolutely different. They enhance. It's— I mean, I'm still alone. The standards are high, ladies.
But, and they should be.
Yeah, yeah. I've had men tell me they're too high, and I'm like, well, good, because you're not my person. I'm not going to be around you then. That's fine. Go find someone with lower standards. Fine. It's a great filter.
It is a great filter because I think what it allows us to do is have really clear boundaries. When we're unsure about who we are and what we want, yeah, we can kind of let the rhythm of life take us where it wants to take us. And that's when trouble comes in because we allow, we invite people in our lives that maybe don't need to be there.
Yeah. And I think if I could take the date yourself a little bit further, what I did, and I had a program for this a while ago, but it's gone because I outgrew it. But it was date yourself, date to learn, and then date for whatever you want, like whether it's fun or relationship. Because I've gone through the dating to learn, still dating to learn, I suppose, when I do it. But, and what I was able to see is I would have broken my pattern to a certain extent, but then I would slide into it and I would, oh, I'm overperforming. And it got much easier to back out of that. But dating to learn is a really powerful tool because we don't put the pressure on ourselves to like, I want him to pick me, or I want to be married, or I want to be in a relationship. I'm dating to learn about myself and how I interact in this romantic arena. And I learned so much about what— you're never going to be all the way healed, you're never going to be all the way— it's always going to be something like that. But I learned a lot about like, oh, I, I can be an observer during this process.
It's dating from a place of curiosity versus a place of checking the box.
Yeah, or attachment or something. Yeah, it was very much curiosity. And it was the first few times I noticed my pattern, I was, oh Am I still? And then I was like, wait a minute, hold on. Oh, I did it. But look, I backed out. Oh, but look, I corrected. Oh, look, I can just leave. Oh, look, I can just— like, you learn all sorts of new behaviors that you can carry forth, and they become your new patterns. I love it.
Absolutely love it. Jen, thank you so much for being here with us.
My pleasure. Thank you for having me.










