2B Bolder Podcast : Career Visibility Strategies & Leadership Stories from Women in Business, Tech & Sports

#126 Deb Boulanger Insights: From Corporate Success to Entrepreneurial Success

• Debra Boulanger, Featured Guest • Season 6 • Episode 126

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Stepping away from the corporate world into entrepreneurship isn't just about changing careers, it's about transforming your identity, mindset, and relationship with work. In this candid conversation with Deb Boulanger, CEO of Life After Corporate, we explore the often challenging but deeply rewarding journey that high-achieving women navigate when launching their own businesses.

Deb shares her personal transition story, from teaching to corporate leadership to founding her own company, revealing that the entrepreneurial path proved more difficult than anticipated. She explains how the identity shift from having preset calendars and clear expectations to designing your own business requires mastering not just strategy, but your internal dialogue. We dig into the psychological barriers that hold women back—particularly around pricing and self-worth—uncovering the startling reality that women entrepreneurs earn just 30 cents to the dollar compared to their male counterparts.

Financial considerations take center stage as Deb recommends having at least a year's cushion before making the leap, while noting that expenses typically decrease after leaving corporate life. For women caught between staying in corporate or launching a business, she emphasizes the importance of making a clear decision rather than vacillating, as "the universe can't deliver on a split desire."

The conversation moves beyond the misleading image of entrepreneurship portrayed on social media to address practical matters like work-life "blend," the critical importance of networking, and how to approach business development. Deb's advice culminates in encouraging women to trust their intuition, what she calls "the niggle" and to price based on the transformation they deliver rather than trying to be merely affordable.

Whether you're contemplating leaving corporate, have recently been laid off, or are already building your business, this episode offers honest insights to help you navigate your journey with greater confidence and clarity. Ready to be bolder in your career? This conversation will show you how.


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Deb Boulanger's Career Tips for Women Transcript

The 2B Bolder Podcast provides first-hand access to some amazing women. Guests will include women from leading enterprise companies to startups, women execs, coders, account execs, engineers, doctors, and innovators.



Mary Killelea (Host): Hi there, my name is Mary Killelea. Welcome to the 2B Bolder podcast, providing career insights for the next generation of women in business and tech. 2B Bolder was created out of my love for technology and marketing, my desire to bring together like-minded women, and my hope to be a great role model and source of inspiration for my two girls and other young women like you. Encouraging you guys to show up and to be bolder and to know that anything you guys dream of, it's totally possible. So sit back, relax, and enjoy the conversation.

Hey there. Today we're going to talk about a hot topic for many women that are transitioning from corporate leadership to successful entrepreneurship with my guest today, Deb Boulanger. Deb is an inspiring business mentor, thought leader, and speaker who has dedicated her career to helping high achieving women confidently step into entrepreneurship. As a CEO of Life After Corporate and the host of the Life After Corporate podcast, Deb is a powerhouse when it comes to guiding women through the often daunting shift from a corporate career to a thriving coaching or consulting business. With over 25 years of corporate leadership experience, managing multi-million dollar business lines, Deb knows firsthand what it takes to navigate career transitions, build sustainable businesses, and breakthrough mindset blocks that hold so many women back. Her nonsense strategic approach has helped countless women turn their expertise into profitable businesses. And today, she's here to share her wisdom with all of us. And I'm thrilled to have her here. Thank you so much for being here, Deb.

Deb Boulanger (Guest): Mary, it's my pleasure. I'm excited for the conversation.

Mary Killelea: Okay, so we had a chance to talk a couple of times the other day and I was like, okay, this woman and I have just such good synergies together. So, I'm excited. Tell everyone kind of your journey in the corporate world. They have that background understanding of the roles that you had and how you got there.

Deb Boulanger: Yeah, so I mean my beginning was really as an educator. I have a degree in elementary school education. And after teaching in the 80s for four years and getting such poor pay that I was waitressing four nights a week, I decided to get a job in business. I started in sales. And because I'm a problem solver and pattern identifier, I would always spot these challenges that we were having cuz as a really fast growing startup, I worked for Gartner back in the day and I would then say, "Hey, you know, we have this challenge and I'd like to go solve it." And the leaders in the company always said yes. So I went from sales to marketing communications. I hit my first glass ceiling, left for seven years, came back as a VP of product development and kind of the rest is history from there. My pattern recognition served me well in market research and product development and then I was developing all and testing all of these concepts for these business units only to see these ideas really fly off the shelf as new programs that the company was launching. And that's when I said, "Hey, I want to own one of these." And when I decided that my corporate career was complete, there was nowhere else I wanted to go, I decided, well, I know how to do this. If I can do it for the company, I can do it for myself. And lo and behold, I launched my own business. And it was so much harder than I thought.

Mary Killelea: So, you mentioned it was harder than you thought. Let's talk about some of the lessons that you learned.

Deb Boulanger: So getting the inspiration to launch my business was truly the easy part. The harder part of it all was dialing in who I am now? And it's such a huge identity shift when you're used to having your calendar set up for you. You get into the office at 8:00 in the morning and you have about a half hour of getting your act together and then boom, your day is taken off. Like your day is predetermined for you and so are your goals. And so are your expectations. And now suddenly you find yourself sitting at your desk with a lot of ideas, not sure where to focus first and no real discipline around your calendar because the priorities haven't been established yet. And so for me, I started my business not as a business launch and growth expert. I started my business as a life reinvention coach because that's what I was going through at that point in time. And so I was newly minted, new certification. I felt like the newbie on the block, not completely sure of what I was doing or how I was going to get clients. What I learned those first couple years is that when we make this transition from corporate leader to business owner, it's not your latest credential that you're bringing to the market. It's the complete compilation of your lifetime of experience, including other things that you did before you even got to corporate. So, I mentioned teaching and teaching other people. When I discover a path or I have a framework or a template, my next desire is who can I teach this to so that they can have this experience too. So it was everything. It was the teaching, it was the personal development that I had gone through and breaking through psychological barriers. It was the frameworks that I had developed when I was at Gartner on how to launch things, how to do market research, how to test the market and bring high demand services that people wanted to sell, people wanted to buy that were easy to sell.

Mary Killelea: Everything that you just said resonates so strongly with me because I am going through that transition right now. So I'm like check check and we're talking. I'm like okay, I got to book an appointment. What do you tell the women because there's so many women that work for Corporate and their title is their identity. How do you help them detach from that? I mean, you talk about looking at the full picture, but I know there's so much more to it than that.

Deb Boulanger: Yeah. And it's more of how do they integrate with that and not detach from it. So when we are in the corporate world and when we have achieved great things and for some of them they always had that ideal like I want to be in the sea suite or I want to be a senior executive for me I didn't really have that direction all I knew was I love to solve problems and I like to achieve things and I liked recognition so that was and I was slight slightly insecure so that's a perfect recipe for corporate success Right? So you work hard to get the recognition. You happen to be smart, but you don't know it. All of those things. And so you don't leave that achievement behind. Like I am proud of the work that I did when I was in corporate. I am proud of the level of success that I achieved. I never imagined that that would be my path when I was getting my degree in education.

Deb Boulanger: So I think you don't throw that away. It's just that you add you round it out. You round it out with bigger leaps and moving through impostor syndrome in a new way, taking bigger risks. So, in some ways, yes, you're leaving the title behind and you are a beginner, which is really hard for accomplished women to tackle. It's like, wait a minute, I knew everything. I had it locked and loaded. I knew how to manage internal politics. I knew how to be successful. And now suddenly here I am and I don't have a clue. I think the hardest piece is not letting go of the title but to embrace the beginner's mind of oh I'm I do need to learn new things. I am new to this and it feels a little uncertain and insecure.

Mary Kilelea: And how do you stay resilient during that moment if you know stepping off the ledge and being uncomfortable because I know there is growth in that. I mean everyone says it and I believe in it but your resilience is required.

Deb Boulanger: Yes. Now more than ever. I mean we're recording this podcast at a very strange time in history and a very challenging time for women everywhere. And so whether you're still in corporate or you're making this leap, resilience is the number one attribute that you need to embody. And for me, it was a journey of faith because I felt called to do this. It wasn't an idea that I incubated in a vacuum. It was something that I felt called to help other women like oh wow I kind of created this level of awareness about this stage of life I am in right now and how my needs have changed my desires have changed and what I want and my life has changed. I can share this with other people. And so it came from a desire to to share and to help others along the way. And I have felt that responsibility, but it is a calling. And in our corporate swag, we have resilience revolutionary, you know, printed on the sleeves of our sweatshirts because resilience is key.

Mary Killelea: Yeah, absolutely. So, let's talk about life after corporate. Appropriate name. Give us an overview of your company. who you serve, the things that you offer, and and we'll start there.

Deb Boulanger: Yeah. When I first started it, I took everybody. It's like, if you want to launch your business, I can help you. As long as it's a service-based business. And what I learned along the way is the way I think, the way I operate, and where I've come from, how I speak, and how fast I move resonates most strongly with other corporate women. So, I work only with corporate women leaders. When I first got started, most of them were in their 50s, some in their 60s. Now, I'm finding younger and younger leaders coming to the entrepreneurship table in their early 40s or some in their late 30s. And it doesn't matter where you are in your corporate journey. It matters that you've had that corporate experience because you'll resonate with how I teach, how we operate inside our programs, which are the launch lab if you're just getting started and the reliable revenue mastermind if you're looking to scale up revenues to mid 6 figures. And so I learned early on that it's a journey everyone takes because you'll kiss some frogs before you find your ideal clients, but that is also a key part of the journey.

Mary Killelea: Like I said before, I'm kind of your ideal client in the sense that I'm trying to get clarity. How do you help women get clarity when they're afraid of leaving money on the table or they see themselves being good at multiple things? You know, how do you work someone to feel secure in their clarity of choice if you will?

Deb Boulanger: Yeah, absolutely. So clarity is the very first step and like you just voiced there's a lot of things going on in your mind and so the first step is learning how to master what's going on in your mind. Literally it's not a business skill. It's about let's get clear on what that internal talk track is. The very first thing that you do in the launch lab is identify your self-sabotage pattern because if anything's going to take you down, let's call it out front so that we're aware of it. Right? And a lot of that is happening right now. And it happens to women before they take the leap. Like what happens if I'm not successful? What happens? I may have had conversations with women who said, "I'm so afraid to leave my corporate job. I don't want to be homeless. I don't want to live in a box under a bridge." Well, that's not likely to happen. That's a fear-based response. So, in order for you to take powerful action, we need to get fear in its place, and you need to take control.

Mary Killelea: That's such good advice. What financially do you advise someone? You know, like there's obviously some situations where you get severance, which is wonderful, I think, because I'm just not about entitlement. So, I think things like that are truly gifts. I guess what's your recommendation for someone with me?

Deb Boulanger: Yeah, and it varies. You know, there's no one solid path to replacing your corporate salary. I would say make sure you have at least a cushion of a year. And what most people don't realize is once you leave your corporate job, your expenses go down, right? So you're not buying the clothes, you're not spending money on the gas. There's a lot of expenses you don't have. And there's also a lot of habits that we have when we have a big salary. We feel entitled to, you know, buy the designer bag. Like there's no need for that stuff right now. And so your expenses go down. So, the money you have tends to stretch longer. If you can also have another financial cushion, savings that you've set aside, a home equity line of credit, a partner who's willing to foot the bills while you ramp up your business, those are all great things to have in place until you feel like you have a solid footing and you've got this machine of sales and marketing going, at least for the time being, because everything changes, everything shifts. We want to be current to what's happening right now. but you do need that cushion and it takes a year or two to replace a corporate salary honestly depending on how much money you were making.

Mary Killelea: What do you tell the women who are recently kind of shell shocked because they were laid off and did not see it coming. What I find is people get stuck in that shell shock mode way too long.

Deb Boulanger: Yeah. And then there's this: maybe I'll hang out my shingle, maybe I should go look for another job. And there's this point of vacasillation and indecision. And what I always say is that the universe can't deliver on a split desire. It's you you have to decide are you all into the job search and then lean into that and who are you at this stage in your life? What does that ideal assignment look like to you? And or lean into the entrepreneurial journey. What is that vision for the change and transformation I want to bring to the world? What is the problem I solve? Who are the people I serve? And how do I package the price and message that and bring it to the world? And you need to be all in that place. If you're not passionate about entrepreneurship, it's probably not for you. It's not a fail safe if you can't get a job,

Mary Killelea: Right? No, That is such an excellent point because I think with you know, looking at your social scrolls, you know, everyone looks like they're doing so fantastic in their social entrepreneurship which they don't show any of the struggle or any of the real data around finances and all that. But that is such an important thing for women to realize that staying in corporate and transitioning to a different job is acceptable.

Deb Boulanger: Yeah, absolutely. And for some of my clients, that has meant a part-time opportunity that brings in a little financial relief while you're building your business on the side. And so, you're 50% in entrepreneurship, but you're also being an entrepreneur in that you've got a part-time job and your part-time client is actually the investor who's helping you invest and launch this business. So, it's really how you frame it in your mind. It's not that you've sold out. Many people feel shame about, oh, you know, my finances aren't where I need them to be. I'm feeling scared. I'm feeling like I need to get something. Well, get a half-time job. Get a part-time job if you can.

Mary Kilelea: What's one piece of career advice that you wish you would have received while you were in corporate and then now as you as a business owner?

Deb Boulanger: Wow. You know, I grew up in the corporate ranks when there wasn't a whole lot of support for women leaders. Like having that seat at the table was a struggle. And there were many young women who were in my office sitting in that chair across from my desk saying, "Deb how do I do it? How do I get to the next level in my career?" And you know, part of it in corporate life is that it's not safe to stand out. So how you succeed in corporate is by fitting in. And I think if I had my younger self, I wish someone had said, Deb, here's where your magic is. I wish someone would reflect back to me. It didn't happen until I was in my mid50s. And one of my leaders who I had a love/hate relationship with truthfully, but he said to me, he said, "Deb, you know, you have something really special that most people don't have." And he was someone who I really respected. He was a former consulting partner in a big consulting firm. And he said, "You have that ability to recognize patterns, knit together solutions, and bring them to market." And that is a rare skill. And I thought little of me with a degree in education from Leslie University and you know hearing from this guy who has a degree in rocket science from MIT saying I had something special. I really wish people had been more generous with their positive reflections as I was going up the ladder. But I think when you're trying to bring change and you get excited that sometimes you can threaten people internally and what they want to do is they want to keep you in the box and keep you small and keep you contained. And I think bosses and mentors who understand what your secret special sauce skills are and let you bring them to the table. Those are the ideal opportunities.

Mary Killelea: Oh 100%. As a corporate woman or as an entrepreneur and designing your own business, personal branding comes into play. What is your advice or philosophy around personal branding?

Deb Boulanger: You know, I think entrepreneurship and corporate leadership is about being a thought leader and I think really leaning in in these moments. And I think sometimes we're on the treadmill and we don't take time to really reflect on our own. But what is that impact that you want to make and what do you want to be known for? Again, in the launch lab, our very first step is what is your life experience? What were those high points? What were those low points? If you're to leave a legacy and you want to look back and be really proud of the change that you've brought in your lifetime, like what do you want that to be? I mean, for me, it's all about giving women a choice of how they earn a six-figure salary. If corporate is your jam and you thrive in that environment, you go, girl, get that seat at that table, rise up that corporate ladder, be a leader. And if that's not you, if that crushes your spirit or if you find that a toxic culture, then it's entrepreneurship. My whole mission is to close the revenue gap with women founders because what we've learned in these last few years is that women on average are earning 30 cents to the dollar compared to men in entrepreneurship. And that is all about the psychology of self-worth.

We'll be back after a quick break. Hey listeners, look, we all know that being a woman in a male-dominated tech industry is tough. You have to do everything the guides do but backwards and in order to heal. That's why I'm such a fan of the podcast Be the Way Forward from anab.org. Brenda Darden Wilkerson, the CEO of Anita Beam.org and host of Be the Way Forward, is having thought-provoking conversations with leaders from companies like Adobe, Slack, Google about fear, failure, and the faith to get back up again. That's right, not success, but the moment when everything went wrong and what they've learned from some of their worst mistakes. Because we can learn so much more from things that go wrong than from things that went right. Every episode is full of insights, tips, and actionable advice you can use in your own career. Sometimes you don't need your sheer heroes to teach you how to soar. You need them to teach you how to fall flat with grace. So listen to Be the Way Forward wherever you get your podcasts or watch at anab.org/mpodcast.

Mary Killelea: Oh, that's fascinating. So you're you're you're saying that women have a hard time pricing themselves appropriately or competitively.

Deb Boulanger: Yeah. And rightly so. Right. So we live in a culture that has conditioned us to be second or worth less, right? So we are of a lesser value. We are the caregivers. We're expected to do different things. We're feminine. We're emotional, but we're not seen as high-powered decision makers or change makers. And so that unconscious conditioning gets embedded in our psyche. And so when it comes to pricing your services, people are thinking, "Oh, well, I want to be affordable." And it's not about being affordable because you'll starve if you're not profitable. It's about pricing your services based on the transformation you deliver. And that's where, you know, there's a lot of unlearning that needs to take place from a conditioning perspective. And a lot of it happens in corporate, too. It's like we're not aware. You can't read the label from inside the jar, right? We're just conditioned to comply. And you know, I don't know if you ever had this experience, but I remember sitting in a colleague's office and he mentioned something about our 30% bonus. And I said, "30% bonus? Mine's only 25%." And I went to my boss and I said, "Can you explain this to me?" And it was, I didn't know that. We'll fix that right away.

Mary Killelea: Wow.

Deb Boulanger: You know, so it happens and you know, unless you're willing to come to terms with it and call it out and own your value and own your worth, entrepreneurship is a rough road.

Mary Killelea: So, let's talk about work-life balance because I think there's a fallacy that if you work for yourself, it looks like a 20-hour work week and we both know that's not true. So what is your perspective on work life balance for both Corporate because obviously you were very high in the ranks there and how you did that and then also what it looks like now as a businesswoman.

Deb Boulanger: I think, you know, it's a work life blend, right? I think balance is a fallacy. I think there are times in our lives where, you know, we need more downtime and there are times in our lives where we need to push the needle a little harder, a little further. Certainly when you're first starting out and you're building everything from scratch, your your technology, your marketing, your messaging, your assets, your marketing assets, your your product assets, then there's a lot of investment that goes in that. Also even as you're more mature, I mean my business is 11 years old now and we launched the launch lab 8 years ago. It's not a set it and forget it. You know, the market's changing, you're changing, your client's needs are changing. So, adapting there, it's a long way to say that it's important to have a strong set of priorities. And when you first get started, business development is 80% of your focus. If you find yourself in the trap of service delivery taking up 80% of your time, then once that engagement is done or once that cohort is complete, you're going to find yourself struggling because you haven't consistently built up that pipeline of new business coming in. So, it is a balance. I'm not a fan of overwork. I don't work all the time. I happen to love starting at 10:00 a.m. wrapping up my day at 5:00 p.m. and I love Saturdays and Sundays. So, my partner volunteers at a wildlife reserve and that gives me Saturday and Sunday mornings, which are late mornings, which is my most creative time. And I'm writing, I'm doing my newsletters, I'm planning, visioning, playing with IGBT, you know, all of these things. So, for me, that's my blend. And everyone else has a blend. If you're a mom and you have young kids and you're ending your day at 3:00 cuz you got school pickup and then you're working again from 8 to 10, then that's your blend. So, I think it's important to have a blend. But if it feels like you're heading to burnout, that's when we need to pause and take a look at, you know, how are you organizing your time? How are you prioritizing what's on your plate? Because we can only handle about three or four priorities at any given point in time.

Mary Killelea: I love this conversation. There's only a couple more topics I want to touch on due to time, but let's talk about networking because I think a thing that I've observed is a lot of these people who are surprised by the layoffs. They haven't made the investments to build the relationships or nurture or they only think their network should be within or they've only spent time within their circle within their office within their network within the corporate setting. What words of advice do you have for women on networking?

Deb Boulanger: Networking is super important and I didn't realize it when I was in corporate but it was the first thing I dove into in my entrepreneurial space and everything happens to me accidentally cuz I just have a nose for something and I try something out and then it works and it's just like oh in retrospect this is a great strategy. Let's rinse and repeat this. Networking is important. I happen to be a huge fan of Elevate Network. I'll give it a little plug. It's a great network of professional women leaders. It also has a great community of women entrepreneurs. In fact, I launched the luminary entrepreneurs roundtable in 2018. We started in New York and then co hit and we brought it globally and I did that for three and a half years. That was our lifeline. You know, your network, you know, you've heard it say your network is your net net worth. I know about that, but it is your lifeline. It's where you can go to the table, be somewhat vulnerable in a safe container with trusted relationships and ask for support and guidance. And I think that's not available to women. I think the coaching industry has changed. Now there's coaching available for people at lower levels. When I was a group vice president and I asked for some leadership coaching support, I was told that was only available to the C-suite. I think networks are super important. As an entrepreneur, your network is a great place to start. And then pretty soon, I want you to get in front of the room because the best way to build up a mailing list, a portfolio of connections, and reliable referrals, is to be the leader. And again, that was an accidental realization. It just happens to be. I love to lead. I love to be in charge. And so I would start things and I would start communities within these larger networks and then I would realize a year later that oh wow that was a six-figure lead stream for me. Maybe I should do more of that. Maybe I should join a couple of other communities. So networking is essential.

Mary Killelea: What does to be bolder mean to you?

Deb Boulanger: To be bolder means that you are willing to overcome your limiting beliefs and habits to do the thing that feels really uncomfortable. Your potential and the zone of all possibilities list exists outside of that comfort zone. And visibility is currency. And for many women leaders who are comfortable inside the confines of corporate, that level of visibility, whether it's speaking on stages, being on video, there's a level of discomfort there that you can't afford.

Mary Killelea: As we wrap up, do you have any closing thoughts for our listeners?

Deb Boulanger: Lean into the intuition. We have a saying in my circle that you trust the niggle. The niggle is that little thing inside that's like calling you forward and that you question. I remember when I first got the calling to launch my business, I was thinking, are you crazy? Do you know how much money I make? You know, this you're asking me to like to give it all up. So, it was a little dialogue that I was having back and forth with my higher self. Trust and niggle. And also, when it comes to launching your business, really lean into that transformation that you deliver. People don't buy services. People don't buy features. People buy the transformation that you're delivering and so price your services based on the value of that transformation. And if you're not sure how, we have some free resources on our website that'll help you get there.

Mary Killelea: And a great place to end. What is your website?

Deb Boulanger: It's lifecorporate.com.

Mary Killelea: Thank you so much for being here. It is just a pleasure to talk with you.

Deb Boulanger: Thank you so much, Mary. This is such a fun conversation.

Mary Killelea: Thanks for listening to the episode today. It was really fun chatting with my guest. If you liked our show, please like it and share it with your friends. If you want to learn what we're up to, please go check out our website at 2bBolder.com. That's the number 2, little bbolder.com.