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Natalie Ellis
Welcome back to the Boss Babe podcast.
Danielle Peazer
Okay.
Natalie Ellis
I was supposed to be coming to you from the Cotswolds, but we actually cut our UK trip short, and I am back in Austin now, which, you know what, feels really, really good. There were so many reasons that we cut this trip short. We left later than we were going to, and then we come back a couple weeks earlier than we were planning. And I just think I overestimated how easy it would be to travel internationally with being so pregnant. Like, third trimester travel during a heat wave when you have no AC in the UK is quite an experience, let's put it that way. Put a toddler in the mix of that. And I was like, you know what? I'm ready to get home, have my home comforts be in my routine. I think that would feel really good.
Danielle Peazer
And I think we're just gonna do.
Natalie Ellis
Maybe a fun California trip or something like that. That feels a little bit more manageable, let's say, as our kind of final trip before baby arrives. But, yeah, that is my little life update. But diving into today's episode. Today's episode is for the woman who has built a really beautiful resume, but can't IG whisper that there might be something more? So I'm sitting down with Lindsay McMillan, who is a former VP at Goldman Sachs who walked away from Wall street not because she hated her job, but because she loved the idea of something else more so. She was in finance for six years with a promotion to VP at 28, which is wild. And just after that promotion, she made the leap to pursue her dream of becoming a published author. And not just any dream. We're talking Penguin Random House book deals and incredible, incredible love stories. And so in this conversation, we talk about why leav your career to do something else or. Pivot isn't always about burnout. It could be about a dream pulling you forward. What it takes to build a double life as a corporate exec and a creative. The fears behind leaving a really prestigious title and salary, even when you know it's time. And then how we can all begin to honor that quiet voice asking, what if I did the thing I actually really want to do? So if you've ever wondered whether it's too late to pivot, if it's too risky to leap, or too indulgent to.
Danielle Peazer
Choose your art over your title, this.
Natalie Ellis
One is for you. And I think you're right.
Danielle Peazer
Really, really going to love it.
Natalie Ellis
Let's dive in.
Lindsay McMillan
Lindsay, welcome to the Boss Bay podcast.
Hi, Natalie. Thank you so much for having Me. It's wonderful to be here.
Danielle Peazer
I'm really excited to chat. I just before we hopped on, I read a really interesting stat that 47% of Americans who quit their jobs during the quote unquote, great resignation actually said that they wanted to pursue like a passion as a primary reason versus workplace toxicity or being burned out. Which really surprised me, actually, because I. It totally would have been around the burnout conversation. So I'm just curious, now that you're on this path, have you seen a lot of this and have you noticed this being a really big shift?
Lindsay McMillan
Yeah, it's a great question. And for context, I did. I quit my corporate job three years ago when my first book came out, became an author and creative entrepreneur. And I described it back then as I was not running away from a job, I was running towards a dream. And I think that's exactly what you're talking about of this wave of feeling like, okay, we have this good on paper job. I was working at Goldman Sachs. I was a vp. I could have a very nice future there. But I just felt like, okay, the. The existential crisis of life is too short not to actually be following what's lighting us up. And I think I felt like I was maybe on the forefront of that wave a little bit, but. Absolutely. Especially in the last few years, we've seen so many more people kind of reassessing just what it means to do corporate. I know you're very entrepreneurial and have an incredible story too. So I'm sure you see it and it feels like this total generational rethinking of our attachment to work and our loyalty to an employer versus refusing to quit on ourselves. I said, I'm not quitting a job. I'm just not quitting on me.
Danielle Peazer
I love that. I think it's so true. Right. Like, there's such a difference between leaving a toxic job. Like, that's one thing, but you actually left a really great one. And you talk about that. Do you feel like it was harder, I'm assuming, yes. To leave something good than was awful?
Lindsay McMillan
I think so. Right. Because, I mean, if you're so miserable and you're kind of. Or you're laid off, or it's kind of like you're pushed up against the wall and there's no other choice. And I think that can be beautiful catalyst that people turn that negative moment in their life into something really positive and find the more entrepreneurial track. I think for me, like, I was enjoying it. I was getting to live in London, which was always A dream of mine to be transferred to their London office. I had just made vp, but the context was I had been trying since I was 18 years old to get a book published, and I had gotten hundreds of rejections over the years. I had written five books that didn't get published before my debut novel that people call my first book. So for me, it was kind of like, okay. I knew I had this window where I had my first book deal and then I got my second book deal even before I quit. So I say it's kind of like when the risk of staying became greater than the risk of leaving. That was when I finally was like, okay, I'm going to do this. The day my bonus came in, I went into my manager's office. My manager was also leaving, which made it maybe a little bit easier. But I think we both did feel maybe a little bad we were leaving our team. But you just have to honor that. And people were really supportive because it's nothing personal at all. It's just this is a lifelong dream and this is something that I would regret looking back and saying, oh, you know, I didn't give everything to this. So it felt like the right time.
Danielle Peazer
Which is so funny talking about the right time because you hit VP at 28, which is so young, and then you quit literally a month later. Like, I want you to take me back to that time and talk to me about that. Because I'm assuming, I guess both things can be true. Like, you're working this corporate job. The goal is always, you know, growth. I want to make sure I'm growing, my efforts are being seen. But then also you're getting this book deal. Talk to me about that time in your life and how that promotion felt and then coming to this decision because it's such a big one.
Lindsay McMillan
I know. And it was one of those things where I had thought about leaving. I thought I was only going to be in finance at Goldman Sachs for two years. I thought I was only going to be in New York for two years. I'm from small town Michigan. Kind of like, you know, go do the big city thing and then come home or do something more artistic. But I think I surprised myself with how I thrived in New York and had amazing friends around me and great mentors. And I also navigated being at Goldman Sachs. I gave myself almost a rotational experience where I got to be in investing roles, in branding roles in marketing roles in New York and London. And so I was keeping it fresh. I felt like whenever I was plateauing in A role. I got kind of a new experience. And then when I was transferred to London, that was a bet on myself too, because I didn't know anyone in London. I was moving in 2021, just kind of still Covid times. And then I did. I advocated for myself for the VP promotion. I had fantastic advocates for me, but that was not a clear promotion track. I knew it was a little bit of a risk having to start from scratch with a new team over there. And there were times when I was like, ooh, is this bad? That I'm pursuing my books and my writing and that's my first choice. But then I'm also really trying for this promotion and I felt like I didn't want to sell myself short by not going for it. And I'm really glad that that did work out. It's also parlayed into great experiences. There's so much business that goes into publishing books and building a personal brand and as a creative entrepreneur. So all of that has been extremely helpful. But it was interesting. I think it was lucky timing that I got the promotion when I did, because otherwise I would have left maybe. Right. I got that promotion and it was really. It felt good, like I had really earned something over those six years and I would always have that. And hey, whatever I do next, books and beyond, that's kind of a level of credential that I can't have taken away. So I do feel grateful for how that worked out. It did make it a little tougher to tell them I was leaving after they were good to me and gave me that promotion. But it was just, again, it was back to the timing of it all.
Danielle Peazer
One thing that you talk about is you actually had a pretty good work life balance at Goldman, which probably is quite rare, especially getting promoted to VP at, you know, know, in your 20s. How did you manage to get promoted and, you know, do such a good job while also having a work life balance? Because I don't feel like I hear that a lot from people in their 20s who are on that kind of trajectory.
Lindsay McMillan
Yeah, I mean, when I was an intern in my first couple of years, there was really no work life balance. And I was deep in the investing side of things, doing private credit and private equity investing. And look, that was great because I was a liberal arts girl. I didn't have the technical skills. I was learning the financial modeling, learning how deals were made. But I got to the end of that couple of years and I was like, look, I am burning. Turned out, I do feel like my spark has been diminished and I'm not. I was still carving out time to write. I was also like studying for the gmat. It was maybe I go back to business school. I wasn't really sure what was next and what. I guess the way I thought about it, I was also thinking about getting an MFA in creative writing. Do I go to grad school for that? But I thought, hey, is there a way that I can actually have better work life balance, still get paid, still have my healthcare benefits and my 401k? And before thinking about a really dramatic leap, I think oftentimes when we're feeling frustrated in our corporate job, especially a really intense environment like Wall street, we're kind of an extremist where we say, okay, I'm just going to quit altogether or I'm going to totally Pivot Industries. You know, at 24. And I just networked within the firm and found the marketing, corporate communications, branding side of things. I was mostly attracted to that. Sure I like storytelling and I have the skill set for it. But candidly it was for the hours and having a more predictable schedule. Because when I was on deals in my first role, I had no protected hours. I didn't have any. It was just very bad on my mental health. It was very had for my outside passions and relationships and all the holistic things that were important to me. So I feel like by navigating that shift and just moving to a part of the company that had a little bit more of regular hours, so I was working, you know, call it more 8:30-7 or so would be more of an average, which is very reasonable for still those years. And I was able to actually thrive because I wasn't a shell of myself when I was there. I had a lot of energy, I was really productive. I also learned that I would carve out time before work to write. So go to the Starbucks across the street at like 5:30 in the morning when it opened, I would write for a few hours and then I would come in. And paradoxically, I feel like I did so much better at work on those days that I was writing before work because I was doing something for myself. I was activating my mind, my imagination and I was feeling really lit up. So I think sometimes companies are worried about people pursuing outside passions cause they think it'll take away from the time that they give what they give to the company. I actually think that the reason I was able to rise up, up as fast as I did and contribute what I did is because I was feeling on fire. For my own things as well.
Danielle Peazer
How did you maintain that kind of rhythm? Getting up so early, you know, putting in three hours of work before even going to work, then working a full work day for a pretty long time. I mean, I'm assuming you did this for years. How did you maintain that?
Lindsay McMillan
Geez, I don't know. I look back on it, Natalie, and I'm like, how did I do that? I think it's partially the adrenaline of love, 20 something life. And look, I was, you know, single, not a family. Like I had a lot of privileges of not needing to be a caretaker, things like that. Right. So it's not like I was some superhuman, But I did get in this rhythm of waking up really early, carving out the sacred time in the morning, going to work, going to the gym, having dinner, trying to still manage friendships. I had amazing friends. And it was about six years, but I think it was kind of those post college years where everything feels very exciting. There is a lot of adrenaline and there's also a rhythm of just getting into that flow with it. I think now if I had to go back and do it all in that same structure, it would be a little, A little too intense for where I'm at right now.
Danielle Peazer
I know I always encourage anyone when they're in the earlier stages of their careers, if they're in their 20s or if they're in their 30s and they still don't have kids and a mortgage and all of those extra responsibilities. I'm like, that is your time to hustle. We talk a lot about freedom, we talk a lot about balance. But I don't think you get that without putting in the groundwork. Whereas that is a lot harder to do when you have a lot more responsibilities. I look at what I was doing in my 20s and I just think there's just no way my life could look like that now and I could enjoy it. But I do think, you know, when you have that ability, you just have to fully go at it. So I love that you talk about that. Another thing that I want to talk about is money, because you went from a Goldman VP salary, which I'm assuming is pretty nice to. You know, it's a very common knowledge that royalties of advances from writing fiction in the beginning don't always is not like the most abundant paycheck. Maybe it was for you, but I know that's like definitely common, common thought for people. So how did you navigate that financial cliff jump if it was one for you?
Lindsay McMillan
Yeah, absolutely. I think it's so important to Talk about money and be transparent with it because it's all fun and games to say quit your corporate job and follow your creative dream. And hey, that's not really the most realistic without talking about all the money. And like you said, I still make, I make maybe about 25% of my. I have a portfolio career, right Is how we talk about it. So about 25% might come from my advances in my royalties. But then I also do coaching. So I work intimately with young professionals navigating career transitions who want to go from one industry to another or carve out more time to feel fulfilled, et cetera. And then I also work with aspiring authors. So I do small group cohorts, coaching, helping other people bring their books to life. I do keynote talks. I've given four TEDx talks which are unpaid. But then that did translate into more paid speaking opportunities. So both at universities, at companies, unlocking your creative power at organizations, women in business organizations. So speaking is. Speaking is more lucrative than the books themselves. And then I still do consulting projects. So I have Lindsay macmillan Creative LLC is the LLC that holds all of this. And then I will. I like having the flexibility to take on consulting projects maybe when it's a down season for my books and then scale off off. Right now I'm moving into a book launch season. So it's nice that's able to be my main focus for the summer. And then, hey, come fall it would be amazing to take on an aligned consulting project for the portfolio and the money of it all. But also I'm more creative and I think I'm at my best when I'm doing multiple things. I used to think my dream would just be writing and in a cabin in the woods, secluded, right on Walden Pond. But I think that that's not really me. I think my magic is that I have, have all of us have this multi dimensionality and I think I thrive when I'm able to be in teams and solving business problems. And that actually makes me much more creative as well. So I had the way I approached it though. I gave myself one year that I wasn't focused. After I quit my Goldman Sachs job, I said okay for one year. Also I had been saving a ton of my salary. I, I saved a lot of my salary while I was at Goldman and I, you know, was very much living below my means in New York in a 300 square foot studio apartment and budgeting really for that stage of life because I knew that I called it like my creative fund. I was just putting money away to enable whatever came next. And so that gave me a year that I didn't actually have to have that pressure so much of immediately making money. I also moved back in with my mom in the beginning and like took a lifestyle hit. And I think there are these trade offs that people don't always want to talk about. So I love that you're kind of bringing that to the forefront. And I, I think it's really cool that we live in an era now that we can have these portfolio careers now as you have done so beautifully, build brand online. Right. Like the fact that we can record this from anywhere, it's really opened it up.
Danielle Peazer
Yeah, I do think it's really important to talk about because I think one thing I hear a lot is the, oh, you know, I could go and make twice the amount elsewhere and work half the amount of hours. And I hear it like when someone's thinking about transitioning from a job into their own business. And I hear it and I'm like, yeah, you absolutely could. And that doesn't always translate. Sometimes takes a long time to get there and often when it sounds too good to be true, it is. And I think it's. I really enjoy how you're bringing in the realness of, yeah, I'm an author and I'm doing what I always wanted to do, but I'm also doing other things on the side to fund that because it does take time and it's just, it just takes that sometimes. I know with my business it wasn't an overnight success. It's taken so many iterations to get to a place where it is financially very, very successful. But it's not something you just dream up and jump into immediately without having any of the prior knowledge or anything set up. So for you, did you want to make sure you had like book deals, a certain amount of money coming in, a certain amount of money guaranteed before taking the leap? Like, how did you think about that decision?
Lindsay McMillan
Yeah, I think for me it was having not just the first book deal, but the second book deal signed before I left because that made it. That went from okay, this is a pipe dream, Lindsay, or this is a one hit wonder to hey, this is the base of an entirely new career path. And again, I knew it wasn't going to probably be just the books. It's kind of you win the lottery if you can just live off your books for a few people, that happens for most of us, that's again one segment. But I took a bet on myself and I said, I'm building This brand and it's actually the Lindsay brand. And then the books are really one pillar of that and that I'm able to do. I gave my first TEDx talk two weeks after I quit my Goldman Sachs job with no public speaking experience. Just went on stage and did it. And I'm a big believer in not even overcoming the fear, but just moving through it. But I think for me it was having the first two book deals signed and then having, you know, just, I guess like that good Safety net of 6ish months of salary tucked away that I knew that I was not going to be so stressed about that during my first book launch and give myself through that first summer of my book launch. And then I sat down and I reassessed and then, hey, I did take on a consulting project, right? But the goal was to always increase the amount of time that I can spend working for myself and decrease the amount of time working for other people. And that's sometimes a slower intersection. But I also think it's a blessing that, hey, we have different levers that we can lean into if we want to be, be bringing in, you know, more money in one season or if we're able to take some time and just go on ourselves and build our personal brand and know that we're not having to be in survival mode because when we're in survival mode and scarcity mode and like we're just feeling so stressed about the next paycheck that of course impedes creative flow. So that's actually why I think corporate jobs can be incredibly nourishing for creative flow until they burn you out. I think there's this sweet spot and a lot of my friends are very creative while in corporate jobs and there is a level, level of security that that can give. I think for me, I just have always been drawn to a more entrepreneurial path and I knew that the books were going to be a part of that, but it was going to be much bigger than that.
Danielle Peazer
Have you ever regretted the decision or sat with, like, what if I did? And has that ever creeped in since you left?
Lindsay McMillan
I've never regretted it for a second or thought, what if? I guess, I mean, I have days when I miss being on a team and going into an office and especially there's kind of a nostalgia to 20 something life in New York City and in London and there's definitely nostalgia for that life stage. But then the reality is so many of my friends have also gone off and done their own thing or left Goldman. And it's kind of this great training ground. So I don't think I've ever regretted it. Sometimes though, I do think I'm like, hey, would you know me being a fractional chief strategy officer somewhere in more of a longer term? Because right now I've taken more shorter term consulting projects. Call it three to six months. There's something nice about contributing in a long term environment and having colleagues and friends around you for the long term. So that's something that I reflect on and I'm kind of meditating on for this future.
Danielle Peazer
Yeah, I love that. And I love how you're just so open to talking about how this can all evolve and how it can look different. Because I do think we just live in a time now where we have so much more choice than ever before. Like you really can go and do and create anything and everything and there's so many ways to make it work for you. I know for myself, I don't think I would fully enjoy being a solopreneur. I love working with people, but I know there's ways in which I want to do it and ways in which I. I don't. But I also feel like you can only learn this through doing it. You can't listen to a podcast and hear what it sounds like. You can only learn it by doing it. So I'm curious for you now, you know what your life looked like then versus what it looks like now. What are the big contrasts?
Lindsay McMillan
Yeah, I mean, you're so right. And I think I went through that season where I was listening to every podcast and reading everything and trying to emulate someone else's business model. And it can be kind of overwhelming for as beautiful as it is to have all these choices, there are also a lot of people on Instagram, on LinkedIn, and in saying this is how you, you know, sell your book and sell your courses and build your brand. And a lot of that was just energetically not resonating with me. I feel like a brand like you, Bill. It's just so. It's really authentic to you. Also, scale isn't always the goal. Like getting venture capital funding and becoming a billion dollar unicorn isn't everyone's goal. And I think so for me, looking at it as, hey, I went from thinking that I needed to scale, scale, scale versus creating this really sustainable model that nourishes and funds my life. Right. So rather than having it be the business verse, at it as the life first. And I think the way that that looks is I was just so the months and even the Year after I left Goldman, I was still so in that culture and that kind of masculine, rigid way of working and thinking and I put all that pressure on myself. I was still working 15 hour days for myself, sitting down at a desk on my computer, having my 20, you know, bullet point checklist every day. And that actually became so overwhelming and so constrictive and I definitely reached burnout working for myself. And now I much more even writing my latest, I was able to carve out entire days, even weeks just to that. And maybe checking email once a day at the end of the day and realizing what is actually urgent and what isn't and time blocking and having the deep creative flow that I think corporate world does not really honor. Like we're constantly switching our attention so much. So just going deeper into how I'm managing my calendar and my schedule and my works, trying not to have meetings on Mondays and Fridays. Like I realized I can create the rules of my own business and I had a level of doubt of if that would actually work because I had only seen that more corporate way work for me when I was at Goldman. So naturally, okay, that's what I had seen, that's what I tried to do. But I'm sure as you've built your business too, it's like, oh, okay. Part of the point of being here is that we can do it differently and we can create a different lifestyle and have flexibility. And I've been actually pretty nomadic the last few years. So I've just got back from a couple months in Santa Monica and. Right. I'm in Michigan now for my book launch events. I'm moving to Texas next month where my fiance is. But it's like this level of flexibility and I think that was something that I did not have at all when I was leaving thing totally.
Danielle Peazer
I think you can really create for yourself the choice. One thing you mentioned that I think is interesting is life first versus business first. And I actually think that's so hard for people to do in reality because a lot of people find it really challenging to say no to the money. So they find it really challenging to cap out on the number of clients that they take when something lucrative lands on their desk. They might say yes to it. And you know, there's nothing wrong with that at all. But I think it takes. Takes a lot to be really intentional about your yeses and your nose. And it takes a lot to leave money on the table in favor of a life first business approach. Do you agree? And then how do you navigate that?
Lindsay McMillan
I Totally agree. And I've definitely taken on projects that in hindsight I'm like, oh, I did this kind of more out of fear or out of not. Not even that wanting money isn't a bad thing or anything. But like, that was the motivator versus, hey, this is super aligned with my vision. And so what I try to do and kind of like connect with what my higher sel. Sounds a little woo woo, I guess. But more into that meditation of where do I see the vision for my life going and what is that future self? What are the projects she is doing and is she. How much of. Is she writing and making money from her own books versus hosting? For example, I'm a breathwork instructor now, so I lead breath work. I'm like, oh, that might be a part that I get to lean into more, but projects that I'm probably scaling down. Ghostwriting. Ghostwriting is very lucrative. I've done it. I'm doing a project or two now. It's not where my future of my life or business wants to go, but it is hard to leave that on the table sometimes. And I look at it, I guess, as a bridge where I don't. I try not to judge myself. I'm like, oh, I'm taken on a project that doesn't actually feel great. The great thing with them, they have a, like a finish line. It's not committing to anything for multi years. And then they can be this bridge where they're giving me more of that financial security as I'm able to play around and keep some of that flow and spark and curiosity around some of these more sacred parts of my life and business with the writing, with meditations, with breath work, rather than coming, oh, I need to make all my money from my royalties and from leading breath work workshops. Like that would not be fun at all. So I think there's a level of that bridge and then hopefully we outgrow it. But I do. I. I've gotten to the point where now I cannot. I get excited in a conversation with a potential client and now I say, okay, I'm gonna sleep on this. Let's reconnect next week. And I just give myself more time because it pretty quickly will surface if it's something that I'm genuinely excited about or if it's something that, hey, it could. I could do it. But my time is, you know, valuable and I need to honor that and not overwhelm myself.
Danielle Peazer
Yeah, I really, really like that approach. I love that simple thing of like this exciting. But I'm going to sleep on it. Just having that little pause to step back and think about, does it align with my core values? Is this really helping me move forward? And maybe it's a bridge or maybe it's, you have the luxury of saying no for that project. But I think that is something that is incredibly important when you're designing a really intentional life. I'm assuming, too, a lot of your career coaching clients start in a their own version of like, this is a good job, but it's not the right job or it's not the right career for me. What do you tell someone who isn't necessarily miserable, but just knows, this is not my path, this is not what I'm lit up by, this is not what I want to be doing?
Lindsay McMillan
Yes, you're absolutely right. I think that's the most common type of client that I work with because. And some of them also don't know exactly what they do want to do. Right? So for me, it was like, okay, I know I want to write books and a way that's. That makes it easier. But then there's a lot of this, hey, I'm on, I'm in a good job. I should be really grateful. My resume looks great, but I'm just not feeling excited and I'm just feeling in this kind of existential, is this going to be my next 30 years? Am I ever. Am I just going to be a cog in the wheel? And I think that I say to people, like, if the Plan B is too good, you'll never actually reach the Plan A. And I think I see a lot of people who do do get stuck and stagnant. And look, everyone's on their own path. I think people come to the realization on their own timeline. But I think the clients I work with are very awakened, if you will. They know that this is a path that they want to get off sooner rather than later. And so it's helping them understand what the Plan A is. And looking at people like you, maybe I can be a role model for some people. I say, you know, make a list of who are people who are living even you don't have to know them personally, but they're living a life and a career that you would love to be in, you know, in five years. And we kind of start there. Because what is the Plan A? Because Plan B can be safe, it can be comfortable. There's a lot of privilege with it. I'm not saying it's a bad path at all. Right. But for many of us, especially Those drawn to more entrepreneurial paths. There is this level of creation and spark that we just feel dulled and made small and constricted within that corporate environment. And I think it's then, okay, identifying dreaming big and not running to, oh, well, this is why that couldn't work out, or this is why I wouldn't be able to monetize that. There's. So as you and I can both be examples of, there are so many ways that we can carve our own path, and I think it's giving permission to really connect with that plan.
Danielle Peazer
A and do you normally tell people to come up with a timeline and a plan of doing it? What. What do you normally tell them when it comes to taking action?
Lindsay McMillan
Yeah, I mean, I think my whole style is this really interesting blend of the creative and spiritual with the practical. Because I didn't just. People look at my story like, oh, she just followed her heart. It's like, well, no, I actually had a very pragmatic plan with all of this and it didn't just, you know, happen overnight. So there's definitely that practical. I usually go to that second, though. I think getting to what vision is and getting to what are the micro steps you can take first and then, okay, yes, within six to 12 months, maybe this is leading to, you know, you quitting your job or a bigger pivot. But I like to say, how can you make the most of that in between? And you don't have to overachieve at your corporate job so much. Like, if you don't want to be there in three years, then be good enough. Be pretty good. You're pretty good. It's going to be like, the people I work with and us, right? Like, we're already going to overachieve, but you don't need to expend 110% like we've been conditioned to. You can save 10, 20, 30% for yourself. And so coming up with, again, what are those micro moves you can make, be it something just for your passion or something that can start making money and you can have this test ground in between. And I think that then helps determine the timeline for when the bigger leap. Also, when some people start doing that, they don't even actually want to leave their corporate job because they're like, oh, now I just feel like the balance is there. So of course, it depends with everyone. But I do think that being able to get really specific and dialed in on a couple of small things you can do with in the next one to two months and then say, okay, how are we feeling with the bigger timeline?
Danielle Peazer
I love that so much. I think that's such good advice. So for you, I'm so curious what, what does your next five years look like?
Lindsay McMillan
Oh my goodness. Natalie. Asking the tough questions. It's so funny because. So I have my third book launch that's coming out this July, July 1st, and I'm just gearing up for all of that and I do feel like it's kind of this. It's really cool how much has happened in the last three years because you and I can probably both be maybe hard on ourselves. Somet in life or business or it doesn't feel like a lot happens all at once. But then looking back I'm like three years ago I was literally just quitting Goldman. I hadn't even had a first book come out. My first book came out, my second one and on my third one. So books are going to be continue to be a staple, I guess of my life and career. I have my first poetry book that's going to be coming out in the fall. All about love and self discovery in New York city in your 20s, which I look at my books as time capsules of my life. So continuing to write and I guess document my life through fiction, through poetry, that's always going to be there. And then I think really dialing in with the coaching side of things, with just the speaking side of things and with being unapologetically me. I think I had this fear for a long time that I was going to become unhirable, that I was like that the path I was on wasn't going to work and so I was going to have to go backwards. And so I found that I was making myself small in how I showed up online or in what I said in interviews or in offerings that I put out because I had this fear that Goldman or like whatever company that I might need to work for would see that. I've also had consulting clients tell me that they think that I'm too vocal about my own books or my own brand. And it's like that to me is just an indicator that we're not an aligned partnership. So for me, the next five years is truly stepping into my own voice. I think I've done a great job at it through my books, but I've been a little bit shy on truly just showing up as me and trusting myself and not feeling like I need to be this people pleaser. I think that's a big thing that I'm unwinding from and really building that community online, that's I think what I'm most excited about.
Danielle Peazer
I love that V. I'm so excited. So tell us all about your third book. I have a copy on my desk. I'm so excited to dive into it. Tell us all about it.
Lindsay McMillan
Yes, it's an. It's a great summer read. I think. It's called Summer on Lilac island and it is set on Mackinac island in my home state of Michigan. So I don't know if you've heard of Mackinac island or ever been, but I highly recommend putting it on your bucket list. It's a wonderful place to set a story. It's this little island in northern Michigan and there are no cars allowed on the island. It's only horses and buckies and, and boats, bicycles. So it's literally like a step back in time and there are only 500 year round residents and then kind of becomes more of a tourist town. But this, it's a mother daughter story. It's a multi generational family story about Gigi, this late 20s woman who has run away from her hometown as a teenager, was kind of the black sheep of the island, very rebellious, and then is plunked back for the summer because she's run out of money and has been job hopping around the country and has to reconnect with her mom. Mom. They have an estranged relationship and then her hometown. So it's kind of giving Gilmore Girls vibes a little bit of Pride and Prejudice too because the mom and daughter play matchmaker for each other. And like my divorced mom and I have kind of evolved from mother daughter to friends over the years and we've played matchmaker for each other a little bit. So loosely inspired. But really it's probably the book that's least like my own life. And I feel like as I grow as an author, I'm just able to activate my imagination more and create these worlds. And I write it not just from the daughter's perspective. Like my first two books have been much more voices that are similar to mine. And then the main character in this book is. But then I also write the mother's perspective, the grandmother's perspective, these other women on the island. So it becomes more of this mosaic of women. And I'm also meeting with, even tomorrow I'm meeting with a screenwriter. I have the Hollywood agent side of things too to explore turning it into a TV show. So I think that would be on the vision board too. Like super early obviously, but something like a Virgin River, Gilmore Girls, Sweet Magnolia, Heart of Dixie. I think it would fall into that realm.
Danielle Peazer
Oh, I'm so excited for you. I'm manifesting that that would be absolutely incredible. So we'll leave the links for the books below and I'm sure they can just search on Amazon or anywhere they get books to grab it as well. I am so excited for you. I'm wishing you the best of luck and thank you for having this conversation. It was so different and refreshing.
Lindsay McMillan
Thank you so much Natalie. I really appreciate your support and look to you as a beautiful example as well that I can learn from and certainly do so really appreciate it and thanks for having me.
Danielle Peazer
Thank you. Wait, wait wait. Before you go, I would love to.
Lindsay McMillan
Send you my 7 figure CEO operating system completely free as a gift. All you've got to do is leave us a review on this podcast because it really supports the growth of this show. This is my digital masterclass where I'll show you what my freedom based daily, weekly and monthly schedule looks like as an eight figure CEO, mama and high performer and I'll walk you through some step by step how to create this for yourself. It includes a full video training from me and a plug and play spreadsheet to literally create your own operating system. It's one of our best trainings and it's worth $1,997. But I will unlock access for you for free when you leave us a review. I know, wild right? All you have to do is leave your review on the podcast, take a screenshot of it and then head over to bossbab.comreview to upload it and then you'll get instant access to the seven figure CEO operating system. Again, head over to BossBabe. Com review to upload your screenshot and get access. We are so so grateful for all of your support and can't wait to hear how the podcast has supported you.
Host: Natalie Ellis
Guest: Lindsay McMillan, Former VP at Goldman Sachs and Published Author
Release Date: July 24, 2025
Podcast: The BossBabe Podcast
Natalie Ellis opens the episode with a personal update, sharing that her UK trip was cut short due to the challenges of traveling internationally while being in her third trimester of pregnancy, coupled with managing a toddler in scorching heat without air conditioning. She expresses relief and anticipation for a more manageable final trip before her baby arrives, hinting at a potential California getaway. Transitioning into the episode's theme, Natalie introduces Lindsay McMillan, highlighting her remarkable journey from a high-powered VP at Goldman Sachs to a successful romance novelist.
Lindsay McMillan joins the conversation, bringing a unique perspective as someone who transitioned from the structured world of Wall Street to the creative realm of writing. With six years in finance and a rapid ascent to VP by age 28, Lindsay's decision to pivot was driven by passion rather than burnout, setting the stage for a deep dive into career transformation.
Danielle Peazer introduces a compelling statistic: “47% of Americans who quit their jobs during the 'Great Resignation' did so to pursue a passion rather than due to workplace toxicity or burnout” [02:49]. Lindsay echoes this sentiment, explaining her departure from Goldman Sachs wasn't an escape but a pursuit of a lifelong dream. “I was running towards a dream,” Lindsay states [02:49], emphasizing that her move was fueled by a desire to follow what truly ignited her passion, rather than fleeing a negative work environment.
Lindsay delves into her time at Goldman Sachs, describing how she maintained a balance between her demanding corporate role and her aspiration to become a published author. She shares her strategy of carving out early morning hours for writing, which not only provided personal fulfillment but also enhanced her productivity at work. “I would write for a few hours and then I would come in. Paradoxically, I feel like I did so much better at work on those days because I was doing something for myself” [08:01]. This disciplined approach allowed her to thrive professionally while nurturing her creative side.
A significant concern for many contemplating a similar leap is financial stability. Lindsay addresses this by outlining her “portfolio career” approach [12:32]. She diversified her income streams through book royalties, coaching services, speaking engagements, and consulting projects. “I had been saving a ton of my salary and living below my means... this gave me a year that I didn't actually have to have that pressure so much of immediately making money” [12:32]. Additionally, securing her second book deal before quitting provided a safety net, transforming her dream into a viable career path.
Lindsay discusses the flexibility and challenges of managing multiple roles. Her income isn't solely reliant on book sales; instead, she leverages various platforms to sustain her entrepreneurial ventures. “Books are one pillar of the Lindsay brand, and I also do consulting projects...” [12:32]. This diversification not only mitigates financial risks but also allows her to explore different facets of her professional interests, fostering a sustainable and fulfilling career.
When asked about any regrets, Lindsay is candid in her response. “I've never regretted it for a second,” she affirms [18:26]. While she occasionally misses the camaraderie and structure of corporate life, she remains steadfast in her decision. However, she reflects on the potential benefits of long-term consulting roles, highlighting the value of sustained collaboration and community.
Lindsay emphasizes the importance of aligning one’s business model with personal values. She contrasts the high-pressure, scaling-focused mindset often prevalent in entrepreneurship with her philosophy of “life first versus business first” [22:27]. By setting boundaries and being intentional about project selection, she ensures her ventures remain aligned with her vision and personal well-being. “I'm more creative when I'm able to be in teams and solving business problems” [12:32], Lindsay notes, underscoring the synergy between her corporate experiences and entrepreneurial pursuits.
Lindsay offers practical advice for listeners contemplating a career shift. She encourages starting with “micro steps” [27:33], such as gradually pursuing passions alongside current roles to test viability before making a full leap. “Make a list of people who are living a life and a career that you would love to be in... start there” [25:43]. This approach minimizes risks and allows for a smoother transition, ensuring that the shift aligns with long-term personal and professional goals.
Looking ahead, Lindsay shares her excitement for her upcoming projects, including her third novel, “Summer on Lilac Island” [31:18]. Set in Michigan’s picturesque Mackinac Island, the book explores multi-generational family dynamics and personal growth. She also plans to expand her coaching and speaking engagements, aiming to build a robust online community that reflects her authentic self.
This episode of the BossBabe Podcast offers an inspiring narrative of courage and passion. Lindsay McMillan’s journey from a high-stakes corporate role to a fulfilling creative career underscores the importance of following one’s true calling. Her practical strategies for financial stability, work-life balance, and sustainable entrepreneurship provide valuable insights for ambitious women seeking to build a Freedom-Based Business™. Whether you're contemplating a career pivot or striving to integrate passion into your professional life, Lindsay’s story serves as a motivating blueprint for achieving both success and personal fulfillment.