EVERYONE Needs a WING-WOMAN: UNCORKED with JEN ANDERSON

What if the real catalyst for your next breakthrough isn’t another process, but a person? 

In this energizing and deeply human episode of the UNCOMMODiFiED podcast, Tim Windsor sits down with Jen Anderson, a self-described “professional wing-woman” who’s made it her mission to fly beside founders, creators, and leaders who are ready to stop overthinking and start soaring. Jen doesn’t just help people manage their tasks—she helps them manage their mindset. With radical curiosity, sharp emotional intelligence, and a knack for hearing what people don’t say, she helps her clients borrow her confidence until they find their own again.

This isn’t fluff—it’s flight. You’ll hear how Jen partners with people to boost their situational awareness, challenge their self-doubt, and get ideas out of their heads and into the world. You’ll walk away rethinking independence, realizing the strength in having someone who’s got your “six” when life or business gets turbulent. 

Whether you’re leading a company or leading your own personal growth, this episode will challenge your view on going solo—and may convince you to invite a wing-woman into your cockpit.

Tim Windsor
the UNCOMMODiFiED Podcast – Host & Guide
tim@uncommodified.com
https://uncommodified.com/
  
PRODUCERS: Alyne Gagne & Kris MacQueen 
MUSIC BY: https://themacqueens.ca/

Transcript

PLEASE NOTE: UNCOMMODiFiED Podcast episode transcriptions are raw text files and have not been proofed or edited. They are what they are … Happy Reading.

© UNCOMMODiFiED & TIM WINDSOR

[00:00:00] What if the missing piece in your personal and professional life isn't just a new strategy or a new process, but a wonderfully provocative person, someone who sees what you don't, says what others won't, and helps you to take bold steps. When you're too cautious or too afraid to take them in a world that celebrates being self-made and hyper independent, what if the smartest move you can make is to connect with someone who's got your back?

Sees your blind spots and senses your breakthrough even before you do some days, helps you stop shrinking, start soaring, and flying free. And what if that person was part consultant, part cheerleader, and a full fledged wing woman? Aha. That's interesting. Hey, my friends. Welcome back to the Unmodified podcast.

I'm Tim WinDor, and today on the show my guest is Jen Anderson. Jan, welcome to the show.

Hi. Nice to see you today. 

[00:01:00] Ask now, who is Jen Anderson? So Jen is a professional wingwoman, which we're gonna talk about today. She partners with business owners on strategy, collaboration, communication, and getting ideas out of their heads and into the real world around them, which isn't easy for people 'cause we overthink things and get stuck.

Sometimes we need somebody flying, beside our plane to help us. So that being said, I love Uncorked drink with my guests. Let's do that. Jen. What are you drinking tonight?

almost summer. 'cause it's what Nice weather here. I've got a classic iced tea, a spiked iced tea. Sun Cruiser. 

that looks good. Okay. Well you know what I, I went sort of similar, a little different. Open it up first. Hopefully I don't get it all on me. I doing a white claw, a hard seltzer li it's 

I like 

So Cheers. 

to you. 

Yeah. Celebrate celebration of almost summer. 

Hmm. You know what? That's a decent drink. I don't drink a lot of those, but they're not too bad at all.

All right, so I love to sort of crack open a conversation with the question, and I'm just gonna lay out my questions in general to you to start and we'll sort of pick [00:02:00] at them as we go. So I gotta, I gotta understand, and my listeners have, what is a wing woman? Okay, we gotta understand that. We obviously have to figure out why do you identify as one and why does everyone need one?

So let's start with this. What the hell is a wingwoman, Jen?

Isn't that the question? That is the burning question that I get asked frequently. It is a self-made, uh, title that I have, bestowed upon myself. Because what I found was that the people that I started to work with, I originally kind of thought I was gonna be an assistant. Um, I came from, my background is in fitness and I was in leadership and I led teams 50 plus people.

70,000 square foot building all the places, spaces, marketing, all the business things that you do. so I had all of the business background and the people skills, and when I decided to leave that world, I was like, you know what? I'm gonna take my skills and bring 'em online and, and see who I can help out.

Some visionary, uh, entrepreneurs [00:03:00] that need some help. I can be an assistant. And then I very quickly saw that that really wasn't where my skillset was because what I was finding was they were kind of operating in a silo. And they didn't have anybody to strategize with and collaborate with and bounce those ideas off of and somebody to hear what they're not saying.

So when I started working with my people in that capacity, they were able to open up their capacity and not necessarily their workload. So I was like, the only way to describe it was I was like, I'm a wing woman, I just. I'm partnering with these people. I've been using that term since my, you know, my kids were little.

and that's just kind of always who I am, just a natural collaborator. communication is super important. I'm good at that. So I kind of just started pairing up with people and that was sort of the evolution of that. 

Pretty powerful. And you know, I always like to figure out where do things come from? You know, so where are these words coming from and how does this work? So I did a bit of research, which I [00:04:00] found interesting. And of course most of us probably know that this title originally started as Wing Man.

And that's only because we live in a very patriarchal world, Jen, where we. Tend to look it this way, but the term wing man, I was interested to find out, it's a, obviously it's a military term, but it was started being used first of all in World War II in the 1940s. And it particularly referred to a pilot who flew beside or slightly behind another pilot in formation.

And the interesting thing for me was when I read about this, is that there was some specific things that they had to do. They had to provide support. They provide a protection and additional situational awareness. That's actually from like the manual in 1940s, additional situational awareness. So I wanna talk a little bit about that.

So do you provide additional situational awareness for the people that you consult? And what does that look like? How do you get into their world, figure it out and become situationally [00:05:00] aware of what it is that they might need to be thinking about?

That's awesome. I love that. I'm gonna, I'm gonna be stealing. That situational awareness because that is exactly what what I'm doing with my clients. So once I start to know their, business model, their industry, what it is that they're looking for, lots of times when they're doing whatever job it is that they're doing, they're not looking for the other opportunities and the, the gaps and the opportunities, and that's where I get to come in.

So I get to find them. Things like going on podcasts and talking to people about what it is that they're doing, getting maybe getting on stages or going to networking events. I help them fill the gaps. When you go to a networking event, what are you gonna do afterwards? You just met all those people.

You just gonna put all their business cards in a box. Let's make a plan for that. Let's look at where you're presenting yourself and where you wanna be seen, you know, what audiences do you need to be in front of, whether It's You know, networking or like I said, on stages, on [00:06:00] podcasts. so I get to help them with that 360 degree view because sometimes they're doing, they're focused on that task, and I get to go, Ooh, you know what you missed.

Let's get you over here.

It's really powerful and full disclosure to my listeners, I mean, Jen is how I ended up connecting with Diane Osgood. And, uh, you know, so Diane and I, our episode, would've aired by now, months ago when this one releases and I. Jen connected me with Diane and that was a great connection. And actually there's a couple of other people who eventually are gonna find their way onto the podcast as well that Jen connected me with and I really appreciated that.

Jen, we had a great connection. We, we can, of course we connected over this great thing called LinkedIn and then, you know, people reach out and you wonder if you should talk. And it's always that sort of awkward moment of like. What does this person want from me? And all the weird stuff that goes with that.

I thoroughly enjoyed our first conversation, just chatting about life and business and how you look at the world, and it's one of the [00:07:00] reasons why I wanted to have a conversation. 'cause I do think that you embody this essence of, of this. Idea of being unmodified. You wanna take a different vantage point on it.

You wanna help people see a different vantage point on themselves or on their business or on their opportunities, which is really, really powerful. You use this term of sort of this 360 idea. I think that is really powerful because I do think that we all have blind spots, we, things we can't see. sometimes it's a false sense of humility.

That we just don't wanna own. Maybe what we're good at or what we're great at and we're not comfortable in our own skin. I think we've been all sort of overfed this, a little bit of this idea of imposter syndrome at times, where it's like, I can't even feel good about myself because I must be an imposter.

But I think you see through all of that. And you help people get clarity as they're flying sometimes a little bit in, in the clouds. Is that how you would characterize what you do? And, and help us understand why you think that's so important.

Yeah, when. I'm a product of my own service. [00:08:00] So when I was in leadership, I worked best. When I collaborated with other people, that's when the best ideas came. That's when you could kind of feed off of one another, like kind of getting those little nuggets of wisdom or borrow the confidence from the person next to you if you don't have confidence in, in yourself all the time, which all of us don't all the time.

I mean. Hope that you do, but that's just not how life works, right? Like to, to your point, imposter syndrome. But it's like, borrow some of the confidence that I have in you. 'cause I've already seen your social proof, I know you got this. So that's how I worked best and I was like, that's what I wanna bring to the people that I work with.

You know, when they're kind of, again, in that silo and working on their own and taking that 360 degree look, I mean, listen, you know, I came from fitness. So I worked in a room with 360 degree mirrors. That's what we did. I had, I could, you can't hide. You 

Oh. You know what? I would never see, I mean, listen, I, I feel bad for the people who are behind me when I work out. I don't, I would not wanna have [00:09:00] to see that. And then every, gotta see that all the time. I don't, I don't know if I'd like that. You know, you said something before that I find very interesting and I just wanna pause on this for a second.

And I also want, as listeners, I want you to think about this. You talked about Allowing somebody to borrow your confidence. That is a really interesting idea. And also I love the way that's phrased, so, so what, if I understand correctly, every once in a while, people lack that confidence for some reason in themselves or their work, whatever.

But you are confident for them. You've got faith, you've got belief, and they can borrow some of yours when they need it. And I think that's just a challenge to all of us. I mean, who in your world. Do you need to lend some confidence to, do they need to borrow some of your confidence? Who in your world, maybe it's in your family, your children, maybe it's with a coworker, or maybe it's with somebody in business.

Maybe it's somebody in a community group that you work with, but that you know is lacking confidence, but you see it in them all day long. You recognize they can do it. They've got it. You need to lend them your confidence so that they can take that and [00:10:00] say, Hey, you know what? I can do this again. I challenge you to find that person and allow them to borrow your confidence.

It's a great way of looking at it, Jen. I love it.

Yeah. Thank you. Yeah.

I mean, Uh.

we all have those days. You know, nobody's confident all the time, but I also get a chance to hear what they're not saying, and I get to observe and I get to see the cues that they're leaving me visually. So, even though I work remotely, right, when we're talking, I can still see their body language and then my brain goes, oh, they didn't believe what they just said.

I, I'm, I'm gonna help 'em through this. And then I can kind of help 'em with their messaging or help 'em with their presentation or whatever it is that they're working on, their pitch, their proposals. It's like, did you really wanna say that? How's it, how about if we say it in this way or we kind of, then we get a chance to sort of collaborate and massage those things till we get to that right, right moment. 

Powerful. And, again, you, I just love the way you look [00:11:00] at things, hear what they're not saying. It's a really crafty way of thinking about it. And, and so often, you know, I do a lot of coaching and I, I would sort of mirror the experience where sometimes I'm talking to somebody and I'm like. You don't believe what you just said.

It's pretty clear. You. Oh my gosh, man, you're trying to bullshit yourself and everyone else. 'cause you don't even believe what you just said, 

man. I think, I think I heard your own eyes roll. You know, it's a really strange experience when you're listening and watching something and, and I, you know, the one thing I would say about.

the pandemic and how it forced us all into this virtual world and, and even like into Zoom environments and all of these things. the thing I find interesting about that is, is that I've done a lot of coaching over my life a lot. Like I have 70 something coaching clients myself, and we have.

Almost triple that in my whole business. So we got a lot of coaching clients, and I'll tell you there, what's happened to me is when I used to do coaching in a room, you know, I had the whole room going on when you're in person and distraction and everything, but when you're doing zoom [00:12:00] or video virtual coaching and you're, no way to hide and you're looking right into that person and they can be sort of bigger than on your screen.

You start to pick up on things that you wouldn't have. And it is very, very intimate and intense and you can feel it differently in some ways. I find that very fascinating about the sort of the move to the virtual world. A lot of people disdain and I know, but I actually think in some ways it brings us into that experience and exchange in a different way.

Yeah.

I agree. The two dimensional aspect of it is, is sometimes even more telling than 3D. 

Yeah.

So yeah. and when I first went virtual, I was still in fitness at the time and, and You know, I was told, well, you gotta go online and teach classes, which I did not wanna do. That was the last thing I wanted to do.

So I went into my living room and I did, but the funny thing is, is That people started saying, Hey, I'm watching you in California. I'm watching you in New Jersey and Costa Rica. And I was like, there's a whole world out there. I've been inside these four walls. Look at all the people I could meet [00:13:00] and work with if I decided to embrace this.

And it was like. Oh, this looks cool. This looks interesting. I wanna know more about that.

That is cool. And what I love also about your journey and story, Jen, is because the wing woman is not a crafty marketing hook that you just, came up with so you could, you know, haw your wares. You talked about this, that this is a term you gave to yourself or found yourself in, or knew you were back.

With your children, which I find even more powerful in the story because it makes it more authentic. It's not like you just, you know, you went on chat GPT and say, gimme a great handle. I'll, this is who I think I am. So when do you first, like with your kids? I wanna talk about that for a second.

'cause I really think the cool part is this is just something you've, you have been and you understood, you have been for a long time. So how does the discussion of, hey, I'm your wingwoman happen with your kids?

Yeah.

Both of my boys, they're now 18 and [00:14:00] 16, but they played travel sports, their whole life hockey, amongst other things. But really when they were about like eight or nine, my husband and I said, guys, we no longer talk to coaches like you are the athlete. If you need something, you're going to your coach.

And I would tell them all the time, mom will always be your wing woman.

So when you have to go have an uncomfortable conversation with your coach, which they did, because that's just life, Right. My, One of my boys was having a really hard time with a coach and I said, you have an opportunity to turn your season around, but I can't do it for you and I can't want it for you.

But I'm paying for this. So we're gonna go and I want you to take, take control of this and I will be your wingwoman man. If you struggle, you just give me a look. I'll finish your sentence. I'm not gonna leave you hanging. 'cause this was like a scary coach, right? I wasn't scared of him, but you know, the kids, I think he was probably 10 or 11 and he went and he had that uncomfortable conversation with the coach and I just sat by his side and I said nothing.

And [00:15:00] he didn't need me to. He knew that I was there and at the end, the coach said, I've never had a kid come to and do that before. And I said, well, now you have, and you also coach. Please listen to my child. That's your job now. And then at the end of the season, he really, he called my kid out. He said, you know, he was the only one who came and talked to me and changed his whole season.

But I always told him that both of my boys said, this is on you, but I will be your wing woman. I always got your back. 

Awesome. And apparently your dog is your wing dog. I just heard your dog in the background. 

It's like you 

didn't 

know he was so 

dog. I like that you got a wing dog. Which is, which is pretty cool. You know, the way you describe that story with your son, that's interesting. 'cause it, it is so much the image of the research I did historically.

It's this flying alongside, it's, again, if I understand it correctly, historically, you know, you have, a plane and a pilot who has a main mission. but they have this wingman, they have this other plane, another [00:16:00] pilot who's watching out for them supporting, protecting, providing situational awareness, letting them know what's happening.

Particularly interesting that they were watching what they called historically the, leaders six. The six was the rear, the place of the plane. They couldn't see that, that. Back where they were more vulnerable. And so what I love about the analogy is it's like you're telling your son, Hey, you're the pilot here.

It's your plane. You gotta fly it. I can be beside you, I can be there for support, but this is your mission. And I, so it just translates so well. But even more importantly, again, not just some made up marketing stick. So you can go out and say, Hey, I gotta find a crafty sort of hook so that I can be, I can make myself something I'm not, which would be rather inauthentic.

You have been this for a long time, and now you're deciding and figuring out, Hey, I could do this for others. There's, there's a lot of people out there who can, who understand maybe they've got a mission, they're trying to do this, but they, they need some help along the way. So I'm interested to listen, Jen, as, as you've gone on this journey, [00:17:00] what have you learned about yourself, do you think, in the last couple of years?

And what are you learning about? What are you seeing as common challenges that maybe some of your, clients are facing that you're saying, Hey, this is the typical. Challenge I see for a lot of people, and here's maybe ways to mitigate it or work around it, but, but what do you learn about yourself too, along the way?

That's a great question. I, you know, somebody who is in a job for 20 plus years, like I was right in one building, typically doesn't like change. I. What I'm finding now is that my job is changed every day and I'm kind of good at it. I'm, I'm okay with it. it's something I think that really scared me Before it was like that safety, that bubble of like, but I have a job.

I've got all the things I'm needed here. And it's like, that didn't come to be, but I can make my own way. I, I'm, I'm okay. I can figure this out on my own. So that gives me a little confidence. And I, I feel proud of myself sometimes. And even, you know, my boys will say, you know, they ask me, mom, [00:18:00] how's your business going?

And, you know, who are you talking to this week? Who are you networking with? Like, I feel like they're proud of me. So that makes me happy too, that they get to see that, you know, if you don't like what you have, you're, you're not stuck. Go, you can go figure this out.

Um, even at, you know, I'm not, I'm not a young, I'm not a young gal anymore. I'm sure that's shocking to everybody. I. But, um, you know, I'm, I, I like to say I'm well seasoned, so I, I, I have made my own way to do this. And then what I see in my clients is it's really hard to talk about yourself, and that's where they get stuck when we are working on, offering a new package or some iteration of a service that they have or, you know, some new, new messaging or marketing or pitch.

Um, it's really hard for them to talk about themselves kind of objectively. But in a very positive way. So I, you know, those, the communication skills that I have, I think really come in handy because I can help them sort of massage all of that and [00:19:00] say again, like, were you trying to say this? And then lots of times they'll go, Yeah.

I love to write.

And I, and I like to write copy for people, and capture their voice. And they're like, that was exactly me. And I'm like, that makes me feel great. that's what I want the world to see. I see how great you are. So that's what I want everybody else to see. The people that wanna come and work with you. 

Well, so you're not only letting them borrow some of your confidence, you're actually then letting them borrow or access some of the skills that you have to help them articulate themselves, tell their story, write a story, write a narrative that. They can own and feel comfortable in their own skin and using, presenting, speaking with, and all these things.

But even more importantly, along the way, you're also learning that you know, you're actually a lot better at change than you thought you were. Which I think that's a great learning. 'cause change seems like this daunting sort of crazy thing. Actually, at the end of the day, you know? Change is this, ruthless inevitability that we live with every day.

And it's [00:20:00] amazing to me that we all have such anxiety and angst around change. You know, the other day my wife and I were. I don't think a memory came up on her phone as they do. And it was for a number of years ago, and our grandkids were much younger in the picture and they were in our backyard in a little pool on a little slide.

And you know, it was interesting because there was that, and then the next picture was my wife with the grandkids. And it was interesting because both her and I focused on, look how much the grandkids have grown. And then I had this epiphany and I said, Pam, look how much we've changed. And this is the weird thing about your own changing and aging and all of that is that you don't really see it okay.

Until you look at a picture and you go, oh my gosh, I'm, I'm definitely looking older than I was. And, but that's the thing about change is that we have this weird relationship with change, which is just this, part of the natural order. We're constantly evolving, changing, um, morphing, getting wiser, getting more seasoned, getting all of these things we talk about.

But [00:21:00] we're in constant change. And, and yet we have such anxiety and like, people almost like, oh, um, I'm gonna resist change and I don't want to change. I don't know how that really works.

Yeah.

And people will say to me now, they go, oh, you love this so much. This is so great. Don't you wish you would've done it sooner? And I'm like. No, not really. I don't think I would've been ready. I needed all that life experience. I needed, whatever those challenges were, you know, working in, you know, in corporate and working in team building, which I, I loved, I did, I, I really loved that.

But, you know, there's a lot of challenges. I needed all of that to be in here before I could keep moving on. So, you know, I, I also tell my clients sometimes you can't mess up what's meant for you. So like, this is, this was meant for me. So here I am. So 

yeah, I just didn't. Well, and it's a, that's a great way of looking at life too. And I think, there's an ancient saying or proverb and it, and it sort of tucks into that, it it's quite interesting to me. It says A man or woman with a wise [00:22:00] heart, not a wise mind, a wise heart, understands the proper time and procedure for all things, even when the matter weighs heavy on their heart.

Okay, 

so there's this sense of this, this time and procedure coming together, crescendoing together. To your point, the right moment where, sometimes we, we live with a regret. Oh, I wish I would've done that earlier. The reality is though, is that oftentimes there's this preparation phase. We're being prepared for something we may not fully understand, and all of this start is to make more sense.

Maybe when we get there, we go, wow, all of this has been preparing me for this moment. And I guess that tucks into a sense of destiny and all of the stuff that goes with that. do you feel that for yourself and for your clients?

I do, I do. I feel like all the stuff I just took, all the leadership skills, all the, stuff, the life that I've been, you know, becoming more self-aware. I think, clearly the, the older we get, I guess not clearly, but hopefully [00:23:00] the more self-aware we get Right.

People that are, I'll speak for myself, not people, when I was in my twenties.

I would've been a lot different doing a lot of these jobs. So like I, I needed all of that, in my toolbox before I was able to really come and unleash it and help, other people find theirs. 

Yeah. There's a certain, patients in, finding wisdom 

and and some of it can come. I mean, you can have very young people who are very wise. It's not about age, but 

there is an opportunity, at least with age, to collect a little bit more applied knowledge and wisdom if we're willing to be humble enough to learn it.

So there, there might be a critical component to, you know, not necessarily being still in our teens and having everything figured out. I mean, I don't know. 

You'll go through this soon. How old are your kids now? 

16 and 18. 

So you'll go through this like we did Jen. So from the time, you know, until my kids got to, maybe you're different with your kids, but when my daughter and son turned like 28, we got a lot smarter.

All of a [00:24:00] sudden we got super smart When they turned 28, we got super smart. So 

it's, it's a journey that happens for sure. So. 

So it's coming is what 

It, it's coming. it's Yeah. You'll get, and then it, it'll happen. So, so I want to look at this analogy in a different way for a second. So we've been talking about this idea of wing woman and we've been talking about it in relationship to the traditional way of understanding it militarily as a plane.

So I, do you also think of it in relationship to this idea of like a bird and wings and flying and soaring and nesting and, taking care of things, or do you not see this analogy that way?

I do. I do see it that way. That's part of. Innately, I think who I am, 

I, I've always really rooted for the underdog. I've always been the person. I would even when I was, you know, in school and, if somebody else was getting picked on, I would stand up for that person. But if I was getting picked on, I could just walk away.

It didn't really bother me. So there's always been sort of that energy of like, I want this for other people. And it feels good to me. [00:25:00] Like maybe people say that's my love language, maybe, right? That's, maybe that's your love language when you, you really want to nurture those other people into their own, greatness so that 

Yeah. 

to experience that. 

So I, again, I, I think this is just a really interesting way of looking at this. And so I wanna just push this analogy just for a second and say, are there times where part of your opportunity, uh, or obligation, or your job, or your role, call it, what you'd like is to sort of. Push somebody right out of the nest.

This is like you, you gotta fly baby. Like you don't wanna do it. But is that part of what you do? Do people pay you to push them off the cliff? 

They do. 

Oh my gosh. Like 

knew? Yeah. 

would pay you? Push me off the cliff. No, 

Yes, yes. Several, several people that I've worked with actually. Um, things like, oh, I don't, I don't know if I could, get up on a stage and talk about that. I don't have something prepared. 10 minutes of me [00:26:00] typing what they're saying. I go, here's two presentations.

Let's go. Applied, booked 'em, got 'em. They're doing it. And it's like, now I really gotta do it. And I was like, but you know what? I'm your wingwoman. We got this. We're good. 

You know what I like about that? You know, so here's the great part of what you do, Jen, you if I contracted you, you would, and with one hand, with one wing, you would push me right out of the nest, three fallen like scared shitless, and with the other wing, you come alongside me and help me fly.

Come on this, Jen, 

this is brilliant. Jen, what you do? 

Scoop you right up. with that.

Yep, you right up. Put you out with one 

Yep. 

you up with another. 

That's right. You know, it's just, that's, it's that, that idea, like you, you, you're not doing this by yourself. You know, you're not doing this by yourself. I've got you. I got your back. I'll be, promoting this. I'll be talking about it.

I'll be helping you shape it.

Like this is like a teamwork thing. 

Yeah. Yeah. And it does so much fight in the face, I [00:27:00] mean, of this hyper independency that we have. You know, we've moved into this economy where we've got so much solar entrepreneurship. We've got people working on their own. We've got people figuring it out. There's a certain loneliness that creeps in with that.

All the things that go with. That. And so you're providing a very interesting window into a world that I think is gonna become more and more popular for people to move into solo, enterprises. And yet, while doing that, they take themselves out of that collegial environment, that collaborative environment.

And that's the, the downside, the negative. And what you're doing is sort of trying to push that back in for them in a very purposeful way.

Yeah. And you know, usually, like I said, by the time they get to me, they're ready. They want to increase their capacity, but not really their workload. And so by helping them sort of organize, even if it's just organizing what's in their brain, they come to our. Our meeting meetings weekly, biweekly, whatever we decide on.

there, I'm, I'm prepared so that [00:28:00] they can tick off the boxes and then go back to the task. So then we have that sort of partnership with that. So, they can increase their capacity, but not necessarily their workload. 

That's amazing. So right now you, you do this, you live on Jennifer Street, by the way. I love it 

is for those of you who aren't, for those who are listening to the podcast, you have no idea why I just said that. For those of you watching the video, you know why Jen's got a sign, behind her, says Jennifer Street.

You live on Jennifer 

Street. So I'm interested to know. So what's the next season for you? I, I'm assuming it's just Jen right now. I'm assuming you're a solopreneur. Is that right? 

I am. 

Yes. 

so what's your, what does Jennifer Street look like a couple years from now? Is it, do you have a vision to change the dynamic of your business in any way?

Do you still see, you see yourself as an independent wing woman helping one person at a time? And where's the journey gonna take you, do you think?

That's really good question. I've been floated that a few times, like, you know, people that well-meaning and, certainly, and people that have asked how, you know, I wanna increase my, [00:29:00] capacity in the things that I can provide. But I don't necessarily know if I want, an agency, if I want a team of wing women.

If I want to continue to work one-on-one with clients and you know, help them assess where they are and what do they need in a wingwoman. Um, I know a lot of people that are doers, so when, you know, we identify some of the gaps and some of the things that are not my best skillset, like. You know, doing some of the, the administrative type work, I can get them those people.

So that's what I really like to do, is just kind of keep exploring who I can partner with and, and help them get to the next levels, and then I get there too. 

Yeah. And I, and I like that. And you know, my own journey, you know, I was a solopreneur for, oh. I don't even want, I'm embarrassed to say a quarter century or more. And you know, I only recently, uh, had somebody come into my business, uh, and has become a partner in my business. And recently, in the last number of years, couple years, two years, I've hired my daughter-in-law and [00:30:00] my son does some contract work now in the company.

And it's different now today, but I. Purposely, kept my business small boutique. I kept it, I kept it very intimate, very personal that that fit my value set, it fit what I wanted. I surely could have, more than likely made a lot more money if I would've sort of canned something and, scaled it and all of these things that we, encouraged maybe other people to do, but it just wasn't.

Right. For me, it wa it doesn't mean it's wrong for people, it doesn't mean it's wrong for you or anybody else, whatever, but for me it wasn't right. It wa didn't fit who I wanted to be at the end of the day. And, you know, we've enjoyed a very, very, great life in relationship to being provided what we needed to be provided in the season.

We needed it, but I just didn't it. I didn't want it to be what it never should be for me. So I like the fact that you are in a conundrum about that, Jen. I like that your, your answer isn't just like everyone, well, oh, of course. We're gonna scale this thing. I think the thoughtfulness [00:31:00] of, I don't know what it should be, and I don't know what's right for me, I think it's a really great answer because it's so easy to give the other answer, oh yeah, we are gonna build capacity, we're gonna scale it.

This thing's gonna, you know, which is. Which is okay. 

At the same time, going back to Destiny and what you're created for, I really love the thoughtfulness that you're in a quandary about, and I would encourage you to sit in the quandary. I really would, because 

I think so many of us just default to, well, it's, go big or go home.

Right. 

Maybe not.

Yeah.

It's funny that you say that because you know that, that, again, that idea has been kind of floated. Like, do I train people to do what I do? And I could train people, and it was like, same thing with fitness. I can teach people how to teach fitness, but what I can't teach them is the intangible, and that's what I always hired for, and I believe that that's what people are hiring me for and that I can't teach.

So I could find great people. There's no question. There's a million. You know, you talk about being unmodified, [00:32:00] there's, there's a million people that can do something similar to what I do. I'm sure. But I have that intangible that fits with the right people, 

so, 

yeah. 

it's the, it's the Jennifer, 

it is the, the specific Jennifer that you have to put on this, which is, which is perfect. So listen, if somebody wanted to hunt you down and, and figure out if you were a good wing woman for them, uh, how do they find you? Jen? What's the best way?

Sure. Um, you know, I don't even have a website. I never needed one. All of my business has been referral and word of mouth. Uh, so you can find me, I can give you my email, which is, my initial j, my last name, Anderson, A-N-D-E-R-S-O-N, five969@gmail.com. jAnderson5969@gmail.com. Or you can find me on LinkedIn.

I'm very active on LinkedIn. Um, I really love connecting with people. That's how we met. 

It is, yeah. 

I make a lot of good connections there too. 

You do, and on LinkedIn, I think it's Jennifer 

[00:33:00] Anderson. Right? 

Absolutely. No, I love it. And listen, if you're in need of a wing woman, uh, this could be your wing woman. You need to find her and look her up. So, 

hey, 

let's bring this. That conversation for a bit of a landing, we'll put her back in the nest.

So I, of course, I always like to end my conversation with this question because my world is this idea of un commodification. You talked about it living a unique expression of ourselves for the positive benefit of others. That's, that's an important caveat. And my question to you is, when you walk into a room of people, could be a business room, could be a personal room, you, you decide the context and you're bringing the Jen.

Whatever Jen can usually bring in her unique expression. What's Jen doing in those moments, in that room that you know is, your unique contribution to that space?

I bring curiosity, I bring connection, eye contact. I wanna look at people, I wanna shake a hand, have a conversation, ask a lot of questions, and get to know the people that [00:34:00] I connect with. 

Yeah. 

Yeah. 

And I love that. I think, I mean, curiosity and connection are great qualities. And again, if you're listening in, I think you listen for a reason. I always tell you listener again, what connection are you making in a room of people? It's a powerful understanding. So let's go back and sort of end where I started so again, listeners just listen to this and consider this.

What if the missing piece in your personal and or your professional journey, isn't. Just a new strategy or a process for your business or for your life, but it's actually a person, someone like Jen in your life, maybe Jen, maybe somebody else who sees what you don't at times, who says what others won't, who allows you to borrow their courage and helps you take bold steps when you're a little bit too cautious or a little bit too afraid, and you need a gentle or a forceful thrust.

The nest and then someone to fly alongside you when you [00:35:00] find your wings. That is a powerful opportunity. Maybe you need to be somebody's wingwoman or wing man. We don't wanna leave the men outta this one, but thank you very much, Jen, for your time. And listeners, thank you for your time. Cheers. Have an awesome day.

Thanks Tim. 

Thank you so much, chip. This is fun.