What happens after you escape corporate? How do you make your solo business work long-term—without burning out or losing the freedom you left for?

In this episode, Brett sits down with Jenni Gritters, author of The Sustainable Solopreneur and coach to creatives, consultants, and coaches who want to build profitable, flexible, and fulfilling solo businesses.

Jenni shares her journey from The New York Times to building a six-figure business working just 25 hours a week. Together, Brett and Jenni unpack what sustainability really means—financially, mentally, and emotionally—for Gen Xers who’ve left corporate (or are ready to).

They dive into:

✅ The “three-to-four-year wall” most solopreneurs hit—and how to move past it

✅ Building multiple revenue streams without chaos

✅ Shifting from survival mode to intentional growth

✅ Why sharing your numbers builds trust (and confidence)

✅ How to measure success beyond money—using purpose, time, and happiness

If you’ve escaped corporate or are thinking about it, this conversation is your roadmap for building a business—and a life—you actually want to sustain.

Connect with Jenni Gritters

📘 The Sustainable Solopreneur

🌐 jennigritters.com

💌 Newsletter: The Sustainable Solopreneur

Connect with Brett Trainor

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Hi, Jenny, welcome to the Corporate Escapee Podcast.

Thanks, Brett. I'm glad to be here.

Now I'm excited. I love authors by the way. So anytime I get a chance to bring somebody on, but an author who just wrote, which I will share with folks, the sustainable solopreneur, right? And also coaching solopreneurs. So I'm like, I have to have her on the podcast to talk about this.

Now, there she is.

Yeah, we got a lot to talk about. Yeah, we got a lot to talk about. And the book came out this past week. So, yeah, I feel like I'm in the thick of like book launch mode. So it's been a good learning.

okay.

Awesome. And you were nice enough to send me the advanced copy, which I really enjoyed. I was telling you offline, I'm like nodding my head off. I'm like, yep, this would have been helpful five years ago when I was starting to go through this process. one can group. Well, it's learned, right? We learned from the experiences and, you know, learn from, know you're also a coach, so you've got a lot of shared experiences with folks going through this, this transition as well. So,

Yeah, same for me.

Exactly.

Absolutely.

All right, so before we get into it, why don't you just share with the audience just a little bit about your background, what you're working on. We kind of teased it a little bit, but then we'll get into the conversation.

Hmm?

Okay, yeah. So my background is as a journalist, actually, I spent a decade plus working in major newsrooms. So New York Times newsroom was the most recent one. And I got laid off in 2018, which is a little bit of a rite of passage in media. I think I rarely meet people who haven't been, but I sort of avoided the layoffs until that point. And I had a moment of what if...

I could do this on my own. And so I staged a little experiment for three months and, you know, spoiler alert, I'm like eight years in now still working for myself. And so I started my business working as a freelance journalist and writer. And then over time, I had a really popular podcast called the Writer's Co-op and ended up starting coaching, getting a coaching certification. So at present, I would still say I'm a writer, but my writing is now in service of...

my business, so writing this book, I have a newsletter, most of my marketing is writing, and then I coach solo printers. So my big thing is I coach mostly creative, so people that kind of applies broadly, lots of consultants, lots of coaches, but also marketers and communications folks and artists. And I teach you how to do it in a way that doesn't burn you out. So I started to notice that around three or four years, people found they couldn't sustain what they had built working for themselves.

And so that's where this body of work comes from. And I have, you know, different programs. do one-to-one coaching. I do some intensive so we could talk about that later, but there's sort of a bunch of different ways I help people figure out what model works for them, not just what they've been told to do.

Yeah, no, and it's so good and it's true, right? Because I'm in year five, so I did hit kind of that. It's kind of like that seven year in your marriage, right? You seven years, you get through it for sure.

Totally. You're like, wait, hold on. The things we've been doing aren't going to like, I can't do this for 15 years. You know, that's what people say to me a lot. I love working for myself, but I don't think I can actually keep doing this or I don't trust that it will make money or that my capacity will carry, right? Hence this body of work about sustainability.

Yeah. And that's what I love about it. Cause there's folks that'll talk about how to get started. Right. I do that all the time, but I think the sustainability is a piece that I forget and don't incorporate very often. Cause I'm just trying to get people to get started. Right. We'll worry about sustaining it once you get, know, take that first step, but there's something to be said for that because when I went solo, I didn't tell anybody, which was a huge mistake. Right. So solo consulting and then probably by year two, then I did some fractional in.

started to figure out, I think the last check, like 10 different ways to monetize my corporate experience. But it took three or four years to go through that process, right?

It does. It's around year three or four that I get people coming in going, okay, I survived. Now what? You know, because you really are at the beginning just like, I hope this works. And that's normal. It's really normal, but you're really reactive. Usually you're trying a bunch of different things, very spaghetti at the wall, energy. And so there is this refinement moment that is required. And people will come to me and say, I'm either going back full time or I have to make this work differently. Right. So we're there.

Yeah.

Yeah, which again, I'd rather have that choice, right? If how do I make this work differently than go back to corporate? I've kind of burned all those bridges, so there's no going back for me. But exactly.

Me too. Me too. We make a lot more, we work a lot less. I mean, there's no way. I've worked myself absolutely out of any structure.

And it's, yeah, a hundred percent would not, would not change it. But, know, you got me thinking about that, that transition I had, cause I did solo consulting for about a year. I'm like, this is good. More energy than what I had in corporate. Then I kind of found fractional leadership. I'm like even more energy because I didn't like the project plan and virtual stakeholders anymore. And so that found it, but it wasn't until I uncovered some of the other revenue streams that it got coaching. Like the corporate escapee wasn't even.

You know, I thought eight to 12 two years ago, it wasn't even in, so no idea. It wasn't even on the radar, but it kind of meandered and where I, I don't want to say struggle with the transition, but I got through the solo work where I could figure it out to 25 hours per week. I was making the right amount of money. Everything was rolling pretty good. And then I'm like, let's take on the escapee thing. It like doubled my hours and it just, it blew my model back up. So I had to go back and re figure.

You like got the puzzle put together, right?

Again, all stuff I want to do, so it's not a negative, but it just changed how to figure it out.

Yes.

I think that's how it goes. It sort of expands and contracts, right? So I always say to everybody you sort of have your solid part of your business and you have something that's evolving. So for you, it's all the corporate escapee stuff, right? That's evolving. And so then that starts to grow and then that almost becomes the main nut. And then you have something else that's evolving. That's really common, but I don't think people prepare you for how do you add that and then also manage your capacity well. So

I often teach sort of like different stack structures, puzzles, sort of like ways for people to understand you're kind of always going to be growing something. That's why you picked entrepreneurship, presumably. And it does, sort of causes chaos and then we refine it again and it causes chaos over and over and over again forever. You know, it's like what we signed up for. Yeah.

Yeah.

Yeah, and when did you figure out? Because for me, was my timeframe was like six months, I had some success. had my first client and close to the second. After about the first year, my run rate was close to what my corporate income was. Not for that 12, but that month 13 was close and so sustainable. Then by year two, I'm like, now I know I'm not going back. But to your point, I don't know what the future looks like, right? It's one of those.

that next inflection point, right?

Yeah. Yeah, absolutely. I think I doubled my income from my former job within the first year. And so I really knew at that point, and I wrote something that went very viral, which is what turned into the podcast, because people were like, making six figures. I didn't think people could do that. And I've always been very forthcoming about my numbers. I care very much about it because I think people can't create what they can't see. And people don't get a lot of examples of

Yeah.

alternative models. And so I had that sort of first year win, but then, you know, I got kind of tired of doing freelance writing. And so for me, it's always been almost like boredom and industry shifts actually as well have sort of forced some of these changes over the years, right? I think it might just be how my brain works too, but the money is always, that part has been good for me all the way along, right? So I trusted that part, but it was the like,

Yeah.

Is there something I could choose that I would want to do for more than a year or two? It has always been the question in coaching, actually. I've been coaching for five years. So it was just took me a while to get to that part.

Right.

same, right? was that was probably year four. No, it was when the escapees started is when I started to pick up the coaching. And interesting, a lot of the folks in our collective who again, left corporate, no entrepreneurial experience, right? Maybe they thought about it, but not really. And so they're like, all right, well, I'm just going to be I want to be a fractional this or a consultant, those types of things. But

Thanks

It's got to be at least 30 or 40 % are doing some kind of coaching now is as part of it, even though they weren't even thinking it. So there's something to that. I don't know if you've.

Yeah, well, I think there's a growth edge. So you usually start out as the technician, right? You're kind of the doer when you leave your job. And so you just kind of jump over to doing the same thing you were doing in corporate, but in a different context. And that's sort of usually the first survival stage. You're just transplanting it a little over, right? And then there's a phase where you start to become more interested in the strategy. And so at that point, I see people kind of jump.

If they haven't been consulting, are, they're kind of starting to sell packages or, you know, they're tapping in a little bit of a different way with their clients. And that's sometimes where coaching comes in. And then they'll sort of step into more of a managerial role where they're kind of like, either they have contractors, right? So there's sort of these like stepping stones. So for a lot of us, I think we also start asking, what's the point of this? Do I want to have impact? Do I want to help people? And so those of us who end up coaching, I think we're really interested in the

the people and the tangible impact, which is like a little bit harder to see, I would say, with the, you know, going back and doing the client work. It's just a different monkey, you know?

Brett Trainor (09:39.756)

Yeah. And it's again, I think, and I write about this all the time that my change in mentality, right? Cause it was when I left, I was in, so I did corporate for 25 years and I went into management consulting. actually convinced them to hire me after I had a contract with them whole other episode, but then realized that, when I, they quit on me, I'm like, I just want to make more money. That was my sole goal. hadn't, I wasn't even thinking about purpose or time.

Yeah.

but that opened it up, right? All of sudden you have this time, all of you're making the money and other things started to become important. The health, right? The time is definitely a big one. The purpose of what are we doing? So people still incorporate like, that's not for me. I'm like, you say that now, but I...

time.

I know you just change. mean, and again, you kind of get out of survival mode, I think too. So, you know, once you're like, okay, I can trust the money. What's next? It's almost always purpose and health. Right. and so I write a lot in the book about for each season you're in, you have to ask the questions again, what do you value and what are your priorities? And like, have to, you have to ask that every six months or so, I think at least every year in your business and

Yeah.

So asking those questions, mean, I also have two small children, so they forced this a little bit, right? They're three and six now. But when I started coaching, I realized this is what I love, but it took me three or so years for that to be a solid business model. So I want to say that out loud too, right? That like, there was also the puzzle of, you know, I hit $25,000 months regularly now, but like, it took me a while to build that model.

Yeah.

So I kept some of the editorial consulting work on as sort of a financial engine. So I see people doing this a lot, right? You're sort of like, what do I care about now? OK, I'm going to turn that direction. It's a new puzzle to solve.

Yeah, no, and I appreciate your transparency with the finance, because it is, right? And I just wrote that down to trust the money, right? I think that is the hardest part for folks, but honestly, I don't want to that's easy part. It's there. I mean, it's not complicated. You have to work hard. You can't just show up and it's going to roll. You still have to work hard, but it's not rocket science what we're talking about, right? Yeah.

I agree. mean, it's math, right? And I say that a lot. say like, you know, it's also clarity, though, I think, Brett, like a lot of people come into it saying, well, I want this to work. And I'm like, okay, first of all, what do you want to work? Second of all, what are those numbers? Third, how much time? You know, when I teach business models, I'm like, okay, what's your capacity? And how much time do you have to your point of like, of this many hours, you need to make that much in these hours. So there is that puzzle. I think once you learn how to do it, you become pretty adept at applying it in other situations.

Yeah.

But it is, it's not complicated, I guess, is what I would say to that, right? Yeah. But the clarity is the part that I find is hard for people to kind of, they'll just say, well, I want to make six figures. And I'm like, okay, but why and in what way, you know, let's get really specific about what that is. Yeah.

No, that's easy, Not easy, but it's...

Yeah. And that's, again, I've been writing more about that recently is the what do want? Right? Because again, I said it was money, but then all of sudden, so I've got a crude scorecard that I just call the six F's of happiness. Again, it seems woo woo. But the fact is I look at this every quarter now and say, am I on the right path from where I was? Because I tell people all the time when I was in corporate, my whole life revolved around corporate. When I take vacations,

Right. When do I go see a doctor? When do I work out? Everything was around that job. All of a you've got all this time in the world. You start redefining what, success looks like and yeah.

Yes. I think it was year three in my business where I had a spreadsheet that would show how much I was earning each month, right? And I ended up adding six more lines to it that was like, okay, a successful month looks like yes, this revenue number, but also am I healthy? Am I interacting with people? Like I really had to nuance out the success metrics. And I think people, for a lot of us, money's the easy button. You can say, look, I'm making this much so it's working.

Yes.

But I think probably you see this too, Brett, like a lot of the people I work with are not happy and it's not sustainable. Like, yes, you're making that much, but you're working 80 hour weeks and I need you to go outside. I need you to interact with people. I need you to actually be well. And I think there's no cookie cutter for it once you start your own job, which is kind of what you're saying, right? You're like walking away from baked in structure and baked in success metrics. And now you gotta come up with your own.

Right.

No.

Yeah, come up with your own. I do love the idea. And again, like I said, if we would have met six years earlier, five, you would have helped me think through this quicker because right when I left and I think a lot of us, think it's, I'm going to do on a smaller scale what I did in corporate. Yeah.

what I

It's job title. I'm a lot of time I spend with folks is stop thinking job titles, the small business world and solo. They don't, nobody cares about job titles. They want to know problems. What problems are you solving and how do you solve it? And ideally are you a little bit different? How do you do it differently than other folks? And that's a tough shift for people to think differently. Like I was a VP of sales. I'm like, nobody cares. it's not in a bad sense. It's just who your identity was. And so I know you get you right about that too. How do you start to.

Thanks.

Yeah.

It's a transition. It is a transition or transformation somewhere in between those two, I think.

It is.

Yeah. And the identity piece, I think that you're speaking to is huge, right? It's interesting. think I, it was really easy for me to say, I'm a journalist, right? people would say, amazing. I'm a journalist in the New York times. Cool. It like comes with all these credentials and understandings about my competency. And then I vividly remember saying to somebody, I'm a freelancer now. And they go, that's not a real job. And it was like, yeah. And I was like,

Alright, you're unemployed.

you know, and I'm making double what I used to make. It's like, but these things are not the same. So I've really, think that part of learning how to talk about yourself is one of the hardest parts of the transition and something that takes a lot of reps, almost like a lot of practice. I would find myself even a year in telling people at, you know, cocktail parties that I was a journalist. And it's like, that's not what I'm doing, but it was easier to say that than to say,

You know, my mom can't even explain what I do know. She's like, your internet business of helping, you know, it's like, it's hard. So it takes practice, I think. And it takes frankly, like some internal work of extracting yourself from that identity that was almost like a filler for an understanding people might have about you. Yeah.

Yeah. And I think you'll appreciate this story then, cause I was at a wedding, friend's daughter's wedding, maybe a month ago. And some of these guys haven't seen for 10 or 15 years since they were in grade school. And they're like, well, what are you up to now these days? And I hadn't really practiced. I could talk about the solo when I was doing that, but now with the escapee and you know, with I'm like, kind of a media company, right? Cause I've got, I'm on, I've got 76,000 followers on TikTak. They're like, what?

Yep.

Right. And so I'm like, all right, I really need to come up with a better pitch for what, what am I doing? And,

Yeah.

I know. It's hard. mean, and I think also like you made it up. I made it up. We made up what we're doing. And that's so incredible. And also it's a different language to speak. So I also tell people, I have a friend right now who's, she's leaving corporate like as we speak and she's like, I think I need to be around people who don't think this is delusional. And it is, it's so, I mean, it's why you have community spaces, right? It's why I do. Cause there's something about having someone

Yes.

reflect back to you that you are making a choice that makes sense. Because I actually think this is safer than a lot of after watching people be laid off and laid off and laid off. Like, I would choose this every day of the week. But it's a different version of safety. It's a different version of risk, right? So yeah, it depends what room you're in. If people think what you're doing is amazing or completely confusing. And you want to be around the people who think it's pretty cool and helpful.

Yeah.

Yeah. And support it for sure. And again, people, yeah, looking at you with you said two small kids walking away from they're gonna be like, are you out of your mind? I'm like, no, I mean, layoffs you said he you only hit one layoff. think in the course of my career, it was probably laid off three or at least three or four times. And again, one of our founding members in the collective, he's like, I was laid off three times since 2021. He's like, that's it. I'm not I'm just not doing this anymore. And so

Totally.

Yeah.

The number of people that still think corporate is a safer path is insane. It's become my personal mission to educate and say, you can go test this even if you want, right? You can always go back. Why you'd want to go back? I don't know. I'm not judging, but there is a path to test this.

Yeah. I mean, I think for you and I both, we were talking a little bit about experimentation at the beginning. And part of what I love is I have like 12 revenue streams. If one drops or the market starts to shift, I'm still safe. I can just shift that one versus, mean, was, journalism has totally fractured since I was in that industry. Right. And so I sort of watched it fall apart and started to build other things and ended up

Right.

Much healthier. mean, I work 25 hours a week maximum. I spend a ton of time with my tiny kids, right? I'm like, I'm very well. I'm much more wealth than I was when I worked 60 hours a week as that editor. And it's because of the way this is built. And I think that's maybe sometimes people think you're just sort of flailing yourself off a cliff. And it's like, we have intentional business models. We are pretty clear about where the money is coming from and why. And a lot of the experimentation is also how I think about this, right? Like.

to kind of, okay, this part could maybe grow. Let's play with it a little bit while keeping this stable. You can't do that if there's a structure that's pretty sure. Yeah.

Right. Yeah, no, a hundred percent. And again, it took me a little bit to figure that out. But I love you write a lot about the intentionality, which I need to start doing more. I've gotten a lot better with it, Rex. used to, cause there's a fine line between chasing shiny objects and being an experimenting, right? And you got to find that happy medium where it makes sense. So what was kind of the process for you? How did you, cause I'm assuming when you started, it was one revenue stream. So how did you kind of think through or start?

Yes.

Yeah.

testing multiple revenue streams.

Yeah, I think it's always been dual parts, people asking me for it and my interest colliding. So, you know, when I first started out, I was a freelance writer, right? So I'm just writing. It was a lot of like case studies, reports, articles, blogs. I mean, it was kind of a heyday for those. so, but I had to churn really quickly, right? And then I got really sick when I was pregnant with my son. I got hyperemesis, gravidarm, you puke five times a day. So all of a sudden,

no.

no longer sustainable, right? So part of it is like life has forced me to ask some questions and experiment because I had to, right? How much could I get done asynchronously in 10 hours a week? And still I've always been the primary earner. like, you know, I couldn't just drop that revenue stream. But I think even now what I think about is usually there's this sort of influx, even with the podcast, when I started moving into coaching, people started asking for coaching.

They started asking for the trainings on the podcast. And then they also asked for a lot of other things I didn't want to do. And so I think there's this intersection of, is it fun for me? That's my personality type. If it's fun, I will talk about it. Is there enough interest in it? And then do I strategically see that there's possible revenue there? And something like a podcast or a media thing, that's trickier, frankly. Coaching is almost like...

Yeah, I gotcha.

I don't want to say easier, just a different model. So now I have, you know, six or seven different programs and different things and ways money is coming in. Yeah. So the experiment is usually, it's not just totally off the wall, right? It's usually, there's a lot of information coming in a way that I'm like, this would be a wise thing. But I also say, I'm going to try this for three months. I'm not going to judge it at the end of three months. I will sit down and do a sort of like post-mortem and see, does this make sense to continue?

Yeah, yeah.

Right.

So there is a scientific.

Yeah, no, I love that. And again, I've been definitely, I've definitely become more strategic with thinking through and like, this isn't the right path and flipping this, the script into something else if it's truly not working, right? Cause there's right. Repeating the, um, what I, right. I'm like,

Hmm.

Yeah, repeating the things that are you're like hitting the wall and you're just doing it again and again. I always say it's like you're like trying to bang on a locked door and there's like an open window. Yeah, well, and I think too, like right now there's a lot of buzz about building a big audience and all these things. But I'm constantly saying to people that doesn't necessarily mean monetizing, right? Like there's a big difference between a big audience and a monetized audience. And so the strategy really matters. I mean, coming from a media background.

Right? Just look around the corner.

have like a triple dose of this. And so I'm really careful with people to go, do you want that? Is it an ego thing? Is it a thing that that's the direction you want to build? it, why? Not that it's wrong. And once you can answer that question, we can be much more clear about the strategy we apply to it and the amount of effort you're applying to that experiment.

Yeah.

Yeah, no, makes, and there's not a lot of resources to help people think through this, right? Cause there's, got the VC people and the entrepreneurs and raise money and scale. like, I don't want to do that. Most of the people I work with, nobody wants to build a big business. If you do, if you want to see how big they can build something, most want lifestyle, solo, something I can scale. want to make good money. I want to figure out how to make more money in less hours. And that's the balance, but it's.

Hmm.

Yes.

There's not a lot of resources for folks that have done this in the past to say they don't teach it in business books. They don't, they really don't teach it anywhere. So it's just, again, resources like you that, you know, need to be out there that shared experiences, right?

Yeah, it is. It's like, you people always say to me, well, are you scaling to sell? And like, no, you know, I'm interested in clean, simple, high impact work that's really lucrative. Like, isn't that the best? mean, like that to me sounds amazing. And that's what I've built. I mean, I had a three hundred thousand dollar year last year. I'm working 20 hours a week. Like people will be like, that's insane. It's like, no, that's strategic. That is built that way. That's on purpose. I did that on purpose, you know. And so.

Yeah.

with intention. mean, if you could see the notebooks I have and the diagrams I draw and the ways I'm constantly, my audience knows I'm tweaking things always. And they've kind of come to be used to it. They're, Jenny's changing the program again. It's because I'm learning and I'm listening and I'm adapting. But you're right. There's not a lot of people talking about how do you approach your business with some level of agility and strategy. People really like the strategy part, but there's also the whole other.

Yeah.

sort of like mindset, energy, flexibility arena.

Yeah, you got to build it. the beauty is, again, my audience is all Gen X, right? I'm sure we got some millennials that have snuck in and we got some boomers hanging out too. But I mean, they've got the experience to do all of this. That's the beauty of it. again, it's hard. One, when I first started this, I thought it was going to be more tactics, strategies, right? Here's the framework of how to craft your first offer.

Hmm.

Absolutely.

It's a step before that, right? When you talked about being intentional and having the confidence to like, I can't sell. I'm like, well, you solve problems. If you interview for a job, that's basically a sales call, right? You're thinking, you're listening. Can I do this job? You're hearing business owners say, this is what I need. And you can I solve that problem or not? And then there's just, there's a cost to solve it. And I like to overs, you and I share that it's simple. Keep it simple. Just keep it simple.

We're going back to the essentials. Somebody has a problem. You are fixing the problem with the skill sets that you have. I mean, most of the people I work to, I would say are like really high competency. And that's my favorite because we're not looking at do you need to skill build. And I think people come into this going, well, I need certifications and I need classes and I need and I'm like, I actually don't think so. I think we start with what you are very competent in. And also we do have to, you know, as you said, build a personal brand, look at how you uniquely solve these problems.

Right.

but it gets to be simpler than I think a lot of people make it. And you really only need two or three good clients when you are stepping out. I have a client who she came in making like two or three K a month and now she's just landed two really juicy retainers and she's at 10 K months. And it's like, that's literally all she needed. And it was just a few conversations. It's simple. She's now making 120 K a year. It's like it's landed.

And the opportunities out there, right? mean, that's the thing that we, you know, one of my 10 golden rules is the Pareto principle is your friend, right? The 80-24. So you get the foundation right on a lot of this stuff. The other stuff's going to take care of itself. And then where do you want to dial into on certain pieces? And I'm guessing a lot of your clients are, well, maybe let's take a step back. So the clients that come to you, where are they in their journey? So have they already gone solo? Are they thinking about it? And kind of how do you...

Yeah.

You

Most of them have already gotten solo, so I do get a handful of people who are fresh out of usually corporate jobs. I still get some media folks. Typically it's post layoff angst, you know, and they come to me going, So that is a time when people really like to invest in the intentional build. So I will take a handful of folks. I don't put them in my programs. like take them one to one and we build that infrastructure, the model, the website, all the things.

So I do a little bit of that, but mostly I'm working with people in the refinement stage. So the like three to five years in and it happens again, I would say there's sort of like income threshold. So around 13 K months, there's a tipping around 22 K months. There's a tipping. So people come at those inflection points when they need refinement. And that's my favorite thing, right? Cause we really have something to work with. We're doing a lot of auditing, but also frankly, right? Like that's when all the patterning starts to come up to the sort of like

Yeah.

all the stuff from your childhood or from your former jobs, what you think you have to do, we're really, at those points, we have to look at those because they're usually what's keeping you from growing, not the practical bits. It's almost like if we can work on that, then the strategy is much easier to execute. You can't execute a big marketing strategy if you have visibility issues. If you don't want anyone to look at you, you're not going to show up. And that's because your nervous system is all messed up and has, you know, the patterning there is really

Yeah.

Clenchy and so I do a lot of that kind of work with people to almost like shake out the blanket give them more wiggle room So the strategies work really well. Um Yeah, so it's a little bit more mindset. Mm-hmm

Yeah. No, it's that it's good. It's funny. One of, he's not in the collective. I'm still working on it, but he was a former, news anchor at, think he was Fox here in Chicago, but I don't know if he got caught in layoffs like two years ago, but then he went out to start his own communications company and doing some coaching. Just, I think I was a closet creative all these years. I was stuck in corporates and it's funny. There's a lot of us, GenXers coming out. Yes. It's so.

to

Yeah. So many people were. Yeah.

yeah, I don't think again, Tik Tok wasn't on my bingo card, but it's, it's, it's worked. But you know, back to your point of, it for the, the volume or the, what the you use niche, was the impact your target or who are the, and that's where I've kind of refined my message because a lot of what I blew up with was the anti-corporate rants.

I love that for you though.

The impact maybe, yeah.

Yeah.

So I did find a lot of GenXers that were curious, but it was less about what do do about it, right? You can complain all you want. I say, that's not the future. But when I started to change the message, the overall volume dropped, but it was more of the people that I wanted to connect with. So that was a disconnect in my brain a little bit because it got so used to go volume, volume, volume, but the volume isn't for what my business model is, right?

Yeah, it depends on what you want, right? Like my model is very much about depth. And so it's interesting when I have stuff go viral, it doesn't help my business whatsoever, because those are not the people who want the depth. They don't want to come in and like, repattern their subconscious and build a business that looks like this, because it's hard work. They just want to be, you know, they're kind of just there for the flash. And so I really have had to work with I think my ego around, you know, I have an email list that has 4000 people on it. And still, I, you know, I had a 70k launch a couple weeks ago, like,

The numbers are not necessarily correlated in the way that you think there and so I think a lot of people are like, oh I got to grow and Again, my question for why for what you know, um, I'm not opposed to it I can teach you how to do it. My first job was an up worthy. It was the viral media, you know capital Internet all those years ago. It was like the journalists brought in to teach the clickbait. It was my first job I can teach you it but why right? Um, and so it saves people a lot of time

Why?

yeah, yeah, yeah, yeah.

Yeah, it's such a good point. The why is, a big, and maybe, maybe I'll have to, I'll have to catch off on it. Maybe I can take one of your courses because where I'm learning now is figuring out what are the courses, right? Do I want to hit the top of the funnel, right? Still people in corporate, cause it's a big market and the more people I can get shaken loose and not even if they don't even come into my, you know, the community afterwards, but it's just, I think I can help more people up there.

Yeah.

Yes.

Okay.

think and realize there's an out, but I don't know how to build all that type of stuff, right? I don't know how to build programs. I'm testing and learning, it's so it's part of the.

Yep.

Mm-hmm.

And you'll you'll learn right? I mean, I think especially with that audience to there's so many lurkers, I get people who have like been in their corporate jobs for them, and they send me a DM and they go, Whoa, I love what you're doing. Wait, do you really make? Can you make? I'm like, you better bet you can. So I think for you that I mean, it's such a good in but I talk a lot about offer ecosystems. I think I talked about this in the book of sort of like, you know, it's been interesting. So you're catching me right after this book has been launched. And so I sold a lot of copies, you know, several hundred copies last week. But also,

Yeah.

My wait lists are now packed for all my upcoming programs. There's new people on my email list. And like, that's the point, right? Is like, come on into my ecosystem. And I get a lot of people who hang out for two or three years, and then they're ready for the whole one-to-one thing. That's great. It means my pipeline is so full that I don't have to stress about, you know, what's going to happen in the next few years. I know there's people working their way through. So, I mean, it sounds like that's what you've got to build. We can talk about that online, but wait.

Yeah.

Yeah.

Ways for people to develop a relationship with you that don't actually require your active, you know, face to face.

And it's fun. you're so right on the lurkers because I got, I was tagged in a LinkedIn, a couple of LinkedIn posts, maybe six, didn't even, we worked at the same company a while ago, but we didn't know each other, but he was leaving his company and within his, I'm leaving to go do my thing. He mentioned my name in the LinkedIn post. We had never met, but he had been following my content and it gave him just enough of a spark to go. I'm like, that's why we do this. All right, fine. Yes.

That's exactly why we do this. Because for Ma, I mean, somebody told me the other day, you're like a way fun or way show or a little, you know, you're like the little flag that everyone's like, that's the whole, you know, it is. It's my favorite thing when people say, you inspired me to, you know, ask more questions, frankly, about how work has to look. That's, think we probably share that, right? It's like, you're in a prison, and you know, you have the keys in your pocket, right?

Brett Trainor (33:36.557)

Exactly, and those golden handcuffs aren't so golden if they make a change without your approval, which they will.

No, no, I'm yeah, I mean, there's like I talk about obligation versus inspiration, like which place do you want to build from? What kind of life do you want to have? And I'd rather the inspiration every day of the week, even though there are challenges, obviously to running our own businesses, right? There's a lot of up and down and ebb and flow and all the things but for more people than you'd expect it is the right choice. I think I mean, I don't know about you. I think this is the way of the future anyway. I think we're going

Yeah.

Yeah.

a hundred percent. Right. I mean, I think, yeah, that's a whole separate topic, but I think, right. mean, I'm kind of argued because one of the things I'm looking at without chasing too many shining objects is I've got like centuries of experience now in this collective. So how do I marry this with small businesses that need this help? I mean, one off people are working with them, but I think there's a bigger opportunity to do that. And one of my, I am convinced that if under 10 million, you don't need any, you don't need employees, right? There's enough.

fragmented. Yeah.

It's good.

Mm-hmm.

Yeah.

folks that are very good at doing certain things. And if you build the right ecosystem, love that term too, that as small businesses don't need employees. And so I'm a hundred percent on your boat that if the future is changing, you might as well get out in front of it.

Absolutely. Yeah, I have, you know, I have one contractor. She works 20 hours a month. She is an operations person. So I have a idea for a program and I send her all the info and she gets it all set up for me and it's been the best, but it's not super expensive, right? Like these are things that are important for people to understand. It's a $300,000 business. It's a thousand dollars a month to employ this person to help with some of these things. That is juicy, right? So there's just part of the reason I wrote the book the way I did too is like,

All right.

you're the blueprint, whatever you want, we can probably build for that's like, what I've become known for is everybody walks out with a different business model. And that's on purpose because you all want different things. Yes, like that is how it's purpose built, right. And I think I hope we see more of that. It's much more artful kind of unique approach. The internet is full of loop, you know, this is how you must do it. I just I don't buy it. Yeah.

Perfect. Yeah, it's intentional, right?

I think we will.

Yeah. And I think it's changed, right? Cause the early days and still I'm not a hundred percent. I think we still need a new term for what the future is because, you know, people are still stuck with the old freelancer as, you got to get your from Upwork or Fiverr for the $25 deal. I'm like, no, those days are gone. And the way I tell people to think about it, if you're in corporate, that's, that's a one way, right? It's command and control. They, for the salary, they're going to tell you what to do, where you need to be, what you need to do.

Yeah, I agree.

Yeah.

where the different business models you can go from like contractor, which is more transactional, right? Hey, you're paying me to do this task while I'll get it done. But there's the next elevated level is the partnership, right? Is a fractional. don't, and again, I tell people all the time, I don't care what you call it. You don't have to put a label on it. It's solving the problem. But the relationship is you guys both have to be on board with this. It's not a, I'm paying you. I'm going to tell you what to do. If you get in that, then you might as well stay in.

collaborative. Yep.

corporate, right?

Yeah, I do a lot of working with people at the start to figure out what is your preference, unique sort of mapping on how you work with people. I'm very much a partnerships person. So I always loved either the fraction of whatever you want to call it work that was like strategic partnerships and building. And that's also why I still have one-to-one coaching in my business. A lot of people would say that's not a good idea. For me, it's actually the right fit because I love

partnership. And so there's just, mean, there's just a lot of options. I work with some people now who've opened up collectives. And so it's sort of like an agency, but it's mostly just like, if there's an RFP or, you know, several members of the collective pop in, there's, there's like everything you can think of, right? There's tiny studios, there's agencies, there's, I'm just a contractor. And so the, I think the proliferation of models, at one point I like had this idea of creating a business model library. I haven't done it yet, but

Yeah.

Yes.

Ooh, that's a good idea.

The point is I want people to see look how many ways there are to do this. As many ways as there are people probably. And also the weirder, the more resonant, the more unique, author probably better itself. yeah.

The better and you only need a few people for it to work. yeah, it's again, we were, cause I just had something that it's in my, my starter kit that's 17 ways to monetize your corporate experience and it's growing, right? It's every time I find something new, I'm like, what's added to the list. And I love that idea too, of the different business models. think even with small business owners, there's a different way. don't have to package them as a contract. There's other ways I haven't figured out what that looks like yet, but if you ever do put that.

Yes.

panel together or some think tanked, I'm more than happy to jump in.

We'll let you know.

Yeah, I think a bunch of people would probably put their their info in so sort of like a, you know, a group resource. I do have a column in my newsletter called sample paths that gets at this a little bit because I'm asking people what are the rules you don't follow? How are you? You know, where's your money coming from? What are the so I love that kind of thing. I think you probably do. It's like I just want to see. And the book has a lot of these two case studies where I'm like saying, OK, here's four different ways that you could actually set up a sustainable financial infrastructure like based on kind of where you are and what it looks like. So

Yeah.

Which I found actually, again, it would have been super useful a few years ago for me, but anybody out there that's listening that's still in there, pick this book up because you're right. show it from different perspectives, which it just isn't your, this is what it did for me. You give examples of different ways to think about it. I just think it's...

It's a little...

Yes. Yeah, I actually didn't talk about my model till the conclusion on purpose. You know, I'm like, it's the big reveal at the end of the book, because part of what happens is people come in and say that I want a business like yours. And I actually now say I won't do that. I'm not interested in that. It's not going to work for you. I am like weird and prolific and work in a different way than you do, you know, so it's why I sort of hit it until the end. And so but I do this a lot in my work where I sort of stripped back

Yeah.

Okay, here's a case study of this person. What were they doing? Why did they do it? You know, somebody once told me I'm a practical visionary. It's the right phrasing because it's like, do have big ideas, but I'm also really interested in how it all moves together, right? Like, how are you actually doing that? Not just why, you know?

Yeah, I know that's good.

Yeah, no, it makes it makes perfect sense. And even with the financial part, when did you start becoming more open from was it from day one when you went solo, you started talking about it or

Day one. Yeah, day one for better or for worse. I always, I think it's good for better or for worse for my mental health is why I say that because, you know, sometimes when I talk about money people, there's two parties, there's a group that gets pissed and says I'm lying. And then there's a group that are like, my god, this is amazing. I want to do that too. And so money is just still really divisive. It brings up everything for people. It's very emotionally charged. It's part of why I love teaching about money, but

Now I think it's smart.

pretty much since day one. And I think it's right because it was an experiment, right? And so when it's an experiment, I'm just like giving you data. I mean, I did this this past week with the book launch. Here's how many books I sold. Here's what that means for royalty is like, I want you to know what this looks like in case you decide to do it. You know? Yeah, it's good.

Yeah.

Yeah. And I think it's, I would love to, I thought I'm like, I could do that, but part of me, just 25 years of taught not to keep everything close to the vest, overanalyze it, don't share. but yeah, but I think that the opp, the opportunities, if you do the math, right, again, you, you're good at sharing. I'm, and I was even thinking about what I'm doing with the, the escapee and maybe in some of the small business stuff is start just.

sharing as I go through this process of what it looks like. think people would find value. It's just, I've got to get out of my comfort zone a little bit.

Well, we've been we've been taught that it's uncouth and you know, embarrassing and why would you do that? And so I do think the context is really important. Like I don't just say, look, I made 300k. I'm like, here's my expenses. Here's what my take home actually is, you know, here's what this, you know, if I say a 70k launch, okay, here's what that breakdown is. Here's how many people here's when I'm getting paid that amount.

Right.

You know, I'm also like, have two small children in preschool. Like there's all these things going on in my life, which is why I am making what I'm making. You could make 10 K a month and be happy in a different situation. Right. So, um, but we all have a lot of conditioning. I have a soap box a little bit about money because it's been very dehumanized. Right. It's like this thing that's like separate from us and we push it over here, but it's like, all, we're all human being. It's like such an integral part of everything we do. Like.

Yeah.

Yeah.

And we, and you need it, right? It's not going anywhere. No, you're, you're absolutely right. And no, I appreciate that. was definitely in the book too. You, you laid out the, um, again, cause one thing in corporate, at least for me, when I was in corporate, I looked at everything was, I know I'm getting paid every two weeks. I know what's coming in. Everybody could just rely on, this is what we're budgeting. But when I went solo, then all of a sudden it became cashflow. I'm like, all right, I need this to pay for the insurance. I need this for the mortgage.

Yes. Yeah.

And then after that, then it's just reframed the way I think about it. And even with the money, I tell people that not as detailed as you have that as I've gone through this process, right? When I was in solo consulting, I got that up into the six figures. And then I'm like, I don't, don't, just don't want to do this anymore. And started to look for the fractional. Then I went all in on fractional and got that to six figure. like, no, it's like the Goldilocks, right?

And there is the like I mean I always say there's like building years which are usually kind of financial plateaus and then there's growth years so I had a building year where I set up all the infrastructure for my whole business and my group coaching program and then The revenue showed up the year after I mean, it's just kind of how it works And so I do think there's a huge permission slip in it though for people it sort of just busts all the myths of how

Yeah.

That's what it is.

how we're making money. I wanna know how other people are monetizing their media platforms too. That's hard. Is it sponsorships? I just really believe rising tides lifts all boats too. There's something about like, just because I'm making a lot of money doesn't mean you can't. Somebody said to me the other day, I saw you do this book launch strategy. Would you mind if I use it? And I'm like, go for it. Would love for you to use it.

I'm with you, yeah.

That's what we're here for.

That's literally why I talked about it. Like I launched it and talked about how I was doing it. So, I mean, I told you, I have a podcast called trying stuff that is literally about this, where I just say, Hey, here's something I'm experimenting with. And, you know, here's how it's working for me. The book was an experiment too. That's how it started.

It makes sense. I'm in a deep experimentation phase because I kind of walked away from a lot of the other revenue streams to go all in on the escapee and right. TikTok doesn't pay me a ton, but there's some revenue there and sponsors have. So it's just I've gone away from everything that I've known. Right. Because even as a solo, it was everything I knew into this new world. But part of it is I know I can always go back to some of the other things I was doing before if I have to don't want to. But if I have to, I

I'm proud of you.

Yes.

honestly.

I can absolutely do that.

But you can. Yeah, exactly. I mean, and I think it's always edgy when we decide to do that, right? There's a lot of different ways to bring in revenue. when I switched freelance writing is very like, send a pitch, get a client, it's almost like hit a button, get money. And coaching is like, say something and five years later, someone will hire you, you know, it's like a totally different energetic framework. And so it took a while for me to trust that that model was in place. Well, so

Yeah.

I think you just, you know, that's what happens when you do a pivot. I'm probably like six pivots in. So, you know, you can join the pivot over three years building something new. But yeah, I mean, I think it also like your audience. I've at least found that my audience loves to watch me build. It's part of why they show up and why they're excited. I did a launch squad last week for my book, which meant 95 people signed up to promote the book on my behalf and

You

that's awesome.

It was such a cool, and then I gave them resources, a private workshop. Like it was such a cool give and take and they signed up because they wanted to watch me do all of it behind the scenes. And then I had a hundred people talking about the book on the day of launch. So it was cool. It was so cool, but these are the experiments, you know, and it gets to maybe be fun, as well, you know,

God bless you.

Yeah.

You've inspired me. I am going to become more public with what I might make sense, right? This some of this will work. Some of it's definitely not going to work. I know that for sure. But yeah, it doesn't. I do think people are curious, but it's just it's against my nature. So I just need to keep cracking the shell and.

Yay!

Yes.

Yeah, I love there's a creator I follow who once a month just publishes her numbers and explains what they mean. And I even love that, you know, I like don't even need any of her other content. I'm not her ideal client, but I get her newsletter because of that. So there's something good about you know, we all we all have a little voyeuristic tendency to you want to see what's happening. And we want to know that like some things actually don't work. You know, I've launched programs and then publicly pulled them back a week or two into launch.

For sure.

because I'm like either the pricing's wrong or I don't like it. And I somehow end up with more clients when I do that, right? Cause I think it's honest. and I feel like you have that same, you would do the same thing. Yeah.

that's it. Did you find to when you say, no, I don't, you might not be the right fit or I'm not taking more clients. Well, more people want to work. The more you don't want their business, the more they want to work with you. So I'm like,

Oh yeah. Yes. We'd love a waitlist. I mean, I'm running a waitlist for one-to-one coaching right now. I don't have any more space and my poor assistant, she's like, do not put anybody else on the schedule, But of course, because there's a waitlist, there's like more attention on that, you know? So it is a little, little scarcity. Our human brains like scarcity for better or for worse. Yeah.

Yeah

Smart. So smart.

For sure. No, you're absolutely. And again, this is a brave new world for most of us. so again, there was the Chuchanos, there was corporate, there's entrepreneur, and this is just a whole new world that's unfolding. So I'm excited. Like I'm super energized. This is what I'm doing. I always said I'm never retiring. I want to do what I want to do when I want to do it and make some money. but again, a lot of other variables have now become the driver versus just the money. So.

No,

I think so too. Yeah, and the self expression. mean, I think of it almost as like a and you'll see this in the book almost like an art gallery or something, right? It's like everybody's businesses are these little like fingerprints and the way they're I mean, a business is a vessel for helping other people being of service. Like, it's the thing we do as humans and we got a corporate almost like removes you from that person to person. I help you you help I mean, money is a trade, right? I give you value, you give me value. And that's like,

Yeah.

Yep.

ancient for humans. to me, there's something kind of juicy. And that's why people start asking about purpose and identity when they start to do that.

Yeah, no, I'm not.

I like, because you wrote about that in the book too, about the human to human, which I think is so important, especially in the age of AI, human is going to become even more relevant versus irrelevant. And yeah.

Yeah, make some mistakes, know, like have some typos, you know, just like the less perfect, the better these days, I think, honestly. So I say the weirder, the better, the more resonant. We've all been on LinkedIn. It's crowded there. So say something different. It's like.

Yeah. And that's funny. That's why did, cause I was busting my butt forever on LinkedIn and just slow incremental, then tick tock overnight went say, Hey, here you go. I'm putting you because the unique thing with those, the 75,000 people is 80 % of them over the age of 40 on tick tock. Right. So I couldn't get in front of my audience on LinkedIn, but I can get in front of him on, on tick tock by ranting. That's all right.

Yeah, that's awesome. No, I mean, it's also like, again, break the rules. Like people might tell you, you know, lot of people said, why would you self publish a book? Why would you, you know, you're gonna let other people help you launch the book? What if they say something that you don't want them to say, right? Like, there's all these reasons. But if you're having fun on TikTok, and your people are responding, why wouldn't you be there? Right? It's like, win, win.

Yeah, it's part of me now. It's easy to record. I don't edit it. it's, yeah, for good. And I used to take it personally too. I feel like, wow, I thought this one was going to be really, you know, I'm like, yeah, I have no idea if some are going to be good or not. It just.

Yeah, because it's real.

You're not responsible for that part. That's what I always teach you create it and you let it go. You're not responsible. You are responsible for showing up. You're not responsible for the way people receive it. Because the ones you think will do great never do and the ones that are like throwaway posts are the ones that everyone loves, know, so it is it's there's this like perfection thing that keeps people real stuck with creative output. And I just it's my goal to teach people don't put garbage out there. But like really, most of the people I work with are so conscientious that

All

Yeah.

you can let it be a little looser. It's like, it's be okay.

Yeah, I had and if somebody I don't know if she follows me on tic-nac-a-lom she watches the listens to the podcast But I got it and I don't usually look at too many of the direct messages just because it gets super noisy She's like, you know, you really should you should uncross your arms And I didn't realize that in all my tic-tocks every one of them at my arms are sort of crossed I'm like, my god, I didn't even know I was doing that. So yeah, it's

Give your arms grass.

Yeah, you're protecting yourself. It's a subconscious protection. Literally, that's a body thing we do. Yeah, you're like, I'll use my hands.

And I'm like, Hey, look, it's not comfortable. I'm getting more comfortable with it. But, well, Jenny, we've used it least a ton of your time, but I would love to have you come back. I don't want to, because I didn't even get into half of the things I wanted to ask you about how you coaching and some of your processes, but there, I think there's a lot of value in this, but I'd love to have you come back and do a deeper dive into, some of your methodologies, that we haven't done.

Be happy too.

Yeah. Always happy to. Yep. Always happy to. And I have a program in January that I'm offering called create, which is an eight week, like renovate your business model. so it's a fun way to play along. If people, I'll, I'll send you the link and we can put in the show notes, but that would be a good example of kind of what I'm talking about here of experimentation. Like we're literally looking at pricing offers ecosystems and capacity and how do those dance together and doing little experiments and making tweaks. and it's usually about.

30 or people who do it together. So it's really fun. Artful, right? It's just kind of, because this is, I was laughing, I was looking at this book in the lineup on Amazon, Small Business, and I'm like, I'm talking about a very different thing here. it is, you know, it's much more cyclical, seasonal, artistic, and I think highly effective, to be honest. So, especially right now. Yeah.

Okay, that's awesome.

Yeah.

Yeah, it's actionable. That's what I liked about it. was, you can read it and go like, can start doing this now. Right. It's not aspirational. You do have some aspirational piece that you reveal at the end, but yeah. Yeah. Yeah. Yeah. So highly encourage folks to check it out. And people know I don't have people on the podcast unless I liked the book. So that is the one thing. The one thing I make sure is I read books before I have authors come on just because, I want to be a, yeah. But it's surprising the number of people that don't actually read them.

Yes.

That's very practical.

Thank you.

Yes.

Good thing to do. I know from...

books.

Yes, it's very, I appreciate you reading the whole thing. And yeah, well, we can pop back on here and always talk more about strategically my model and my methods. I'm always happy to talk about it.

Yeah, no, it's so cool. So great to finally meet you. I appreciate you spending the time. And like I said, I'll put all the links into the show notes, but what's the best way for folks to connect with you if they want to learn more?

Sounds great.

Yeah, my website is jennygridders.com. Great place to find me. I'm also on Instagram and LinkedIn at jennygridders, both places. And yeah, I have a newsletter of the same name, the Sustainable Solopreneur, same name as the book. So that is a great way to get essays, case studies, all sorts of things every Monday. In inbox. Yeah, can follow me. Wherever you follow me is fine. You'll get all the info you need. Find me on the internet. Yeah, I'm there. Yes, that is the truth.

Make sure you follow her.

You'll get everything you find one and you get everything so awesome Well congrats on the book and good luck on its the launch I didn't I knew we were close to the launch date, but I didn't know we were that close So it's awesome. So appreciate you coming on and We'll catch you here in the not too distant future. Appreciate it

We'll be right back.

Mm-hmm. Yep. Yeah. Thanks so much.

Sounds good. Thanks, Brett.