MM: Thank you for joining me to co-author this blog conversation with and for trailblazers.
When I thought about who I wanted to interview for this week’s blog, you were the first person who came to mind because you embody so many qualities of a trailblazer. You go first to pave the way for others. You focus on the ripple effect of individual courage. And, you surround yourself with a powerful community.
MM: Tell us a little about yourself, why you started Insure Equality, and your vision for the organization.
ES: One of the ways I love to self-describe is “Big Sister Vibes”. When I was younger, I grew up in a poor and abusive household – a lot of pressure was put on me (and self-imposed) very early. I share all that to say, it’s important for me to call out inequity, to remove barriers for others, and to create community that benefits the masses.
I started IE with my co-founders because we all came together after experiencing our worst days in the insurance industry. That longing for help, for a community, for something more brought us together and gave us a “why.” The critical thing to remember is we love this industry. Not in the way that we’re loyal to a fault, but in the way that we recognize we can do better. We started it to make insurance a more welcoming place, and our vision this year is all about access and community. We’re creating conversations and using tech to help consumers and employees make value-based decisions about their insurance companies and employers.
MM: Based on your experience, what is one of the most important qualities that trailblazers can develop to make an even greater impact?
ES: I love this question because it assumes that we can keep working on it – and that we all have the opportunity to trailblaze. This assumption is empowering. We can all lead from where we are. I’m taking a moment to call that out because early in my career, I developed a terrible case of “I couldn’t-itis.” I didn’t believe in myself or my potential to make a change on my underwriting team, much less in my industry. I thought I was alone in how I felt and what I saw. II wasn’t and never was.
If I could distill all of this into a takeaway, it’s this: trust yourself. Know that up to this point, you’ve gotten through everything you’ve experienced and come out the other side, even if it didn’t go the way you thought it would or should. Have a short-term memory and celebrate the learning, not the loss.
MM: So often I work with women leaders who feel isolated, exhausted, and afraid to take up too much space because they experienced backlash for showing up as their full selves. How do you maintain your energy and motivation?
ES: Excuse me while I take a minute to say, “Yes, me too!” It is exhausting. I thought, eventually, the work would be exhilarating, or like other jobs I had; I’d hit a stride after six months. I didn’t. It was STILL just as hard. What I’d say is that you won’t. You won’t consistently maintain it, and the critical item to remember is that you don’t always have to be the one that holds it for you. It’s why community and cultivating it intentionally for yourself is so critical to your success.
I have a whole team of people I go to when my energy, motivation, and sanity are being questioned. I have my co-founders, my board, friends, family, and, most importantly, other entrepreneurs because they’re going through it too. If I can add more here, it’s that I tried to do it all myself at first. I continuously burnt out and lost sight of myself because I was pretending. You won’t attract the community you need when you’re not fully yourself, including the vulnerable mushy parts. Do the uncomfortable thing, and have a shoulder to lean on.
MM: What advice do you want to share with people who are facing obstacles in the insurance industry?
ES:Talk about it! This concept may seem obvious, but as a veteran in the industry, most of the time, when I asked someone to elaborate or talk about something they felt their voice didn’t matter. It does. Since we started in 2021, consumers have told us, “We’ve been waiting for someone to talk about this, but we didn’t know how to start the conversation.” Or, we hear employees say, “I wish you were here when I started in the industry a decade ago.”
Chances are, you’re not alone in how you feel and you have more power than you think. We have a spot for you to share whatever you want with us and remain anonymous. Whether you want a place to talk about it or to take our culture survey on our website, we have a way for you to get involved in the conversation and raise topics important to you.
MM: We know that we stand on the shoulders of trailblazers who have gone before us. Tell us about an influential trailblazer in your life and what you learned from them.
ES: I have so many, but one of my favorite ones to talk about are from my grandmother Dolly. Sadly, Dolly isn’t with us any longer, but she was blazing trails when it was dangerous for women to do it. She left an abusive relationship, started several companies, and was involved in local politics past retirement. My favorite Dolly story, however, is from early in her career. She went to Rockford Beauty School and rented a chair at a salon across the street from the local bar. The other hairdressers wouldn’t cut the hair of sex workers, but my grandmother said it was silly to discriminate. What made their hair unworthy of her? Their job? She made it clear that people were just that – people, and we should regard them with the dignity we all deserve.
Flipping the script. Elisa shared some questions for me to answer.
ES: What are the questions you wished people asked you about women’s rights and progress?
MM: I wish that people would ask me about feminism. It is evident that we need to talk about feminism because so many people want to move into a post-feminist era, blame feminists for progress, or want to be a feminist but call themselves something different. These strong reactions indicate that (mis)conceptions of feminism still polarize and confuse people. Feminism is gender theory and human rights theory in action.
A gender analysis asks us about the “who” by counting folks based on their gender identity. They check boxes. Great. Now we have numbers of who is where. How many people who identify as women, for example, serve in the U.S. Senate? Feminism asks the “which.” Which women were elected to the U.S. Senate? How do the rest of their identities intersect? Feminism also asks “why?” Why that number? That’s when we start to make changes. A gender analysis without feminism doesn’t get us anywhere.
ES: What’s a roadblock we can all work to remove for each other?
MM: Let’s talk about the patriarchy as a toxic system that affects all humans. I often start out conversations about the patriarchy saying that I’m not going to talk about anyone’s spouse, son, brother, uncle, or lovely next-door neighbor – not right away, at least. I talk about the patriarchy as the system that marks us when an adult declares a sex assignment at birth. The rest of our lives are influenced by that checked box. Recognizing this common system breaks down some of the us/them dichotomies.
In the United States, we pretend that power is invisible and we walk around with our eyes covered because people don’t want to feel uncomfortable about their unearned privilege, and they don’t want to discuss it because they fear that they might lose some of that power. That’s ok. That’s a necessary part of the conversation. If we know how much or how little privilege we each have under a patriarchal system, we can begin the process of bridging. Whereas, if we don’t discuss privilege, nothing changes. That’s the point of patriarchy’s nimbleness. It shifts so that we can’t dismantle it. I am all about keeping my eye on the patriarchy so that we can disrupt it. I’ll take my cue from you and say that I want to ensure equality by getting more women into the rooms where decisions are made.
ES: How do you remind yourself to operate with abundance?
MM: Oh, Elisa. That’s my daily intention and stretch. I was raised in an environment that was framed by victimhood. My father died unexpectedly when I was two. He was a victim of a gun crime during a robbery at a local restaurant. It was one of the first mass shootings in IL. I don’t remember the event, but what I do remember was growing up in a conservative, rural town surrounded by the widow and orphan narrative. I was not an orphan, but in that community, children without fathers were orphans. Yep. This is how I developed my gender lens at an early age. It’s my superpower.
I used to learn the gender roles at church and in the community, but they didn’t apply to my family so I began to see them as constructed rather than infallible. Anyway, I did not realize until I became an entrepreneur just how deeply my scarcity and victimhood permeated my identity. I had no idea that I thought I was not allowed to be financially successful. I didn’t realize that I self-sabotaged to stay in that victim lane even though I excelled in certain areas. Neither of my parents went to college. In fact, my mother took the GED to earn her high school diploma. So, while I broke lots of barriers for myself by earning a Ph.D, I also brought that lack mindset with me.
Today, I operate with abundance by meditating daily to suss out the fear of success still rumbling around in my brain and soul, leaning into what feels risky to develop self-trust, taking contrary action from my old M.O., reminding myself that I am worthy of being my full, feminist self, cultivating a fierce community of chosen family, and expecting that abundance in relationships, health, finances, happiness, and security is my norm.
ES: What’s a piece of advice you wish you believed sooner?
MM: I wish that I believed in my inner compass to make decisions for myself when I was in my 20’s. I wish that I knew that I was free. If I had known that truth, I would have disrupted expectations much earlier.