How This Executive Coach Is Cultivating The Next Generation Of Female Leaders

Eight years ago, Jennifer Macaluso-Gilmore felt like she’d been hit by a Mack truck. “I was laying in bed in the fetal position,” she says. “I was black and blue—on the inside.” Jen had been in a head on collision, but not with a vehicle. Her work life as a highly successful life coach who served over a thousand in-person clients through her classes and her personal life of juggling two kids and a husband with his own business had collided. 

“There’s only so much a human being can give,” says Macaluso-Gilmore. Her one-on-one coaching clients raved about the results she was able to help them achieve: everything from skyrocketing up the corporate ladder with better communication skills to boot to helping them find more happiness, start their dream business and create a healthy romantic partnership. She helped them juice every moment out of life. But her work now coupled with caring for her kids, left her cup empty. “So I took a break—a long break—and changed my focus for even greater impact,” she says. 

Here’s how Macaluso-Gilmore rebooted her one-to-one business—without scaling it—to redefine success for herself while having an even greater impact by supporting female leaders in the world.

Stephanie Burns: How did you get started?

Jennifer Macaluso-Gilmore: Despite having a degree from a reputable university, I graduated without the know-how to do all the things I most wanted in my life. None of my professors—or anyone else for that matter—had taught me about cultivating happiness, negotiating my worth in a job interview, communicating lovingly with a partner or protecting my mental, emotional and physical health. So I was basically a hot mess from my late teens to mid-twenties. I wasn’t successful in relationships, drank too much, and realized my job had nothing to do with my passion. I struggled each morning with waking up and feeling happy. I honestly wondered, “How did I get here?” The greatest indicator of our happiness in life is our relationships—especially our relationship with ourselves. I recognized that I didn’t have a good one so I started working on it.

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Burns: What did you do to build a better relationship with yourself?

Macaluso-Gilmore: I started to become the leader in my own life. I did therapy, I read hundreds of self improvement books, I got sober—and stayed that way for the past 25 years. In getting introspective and doing the work, I not only pulled my life together but realized I had a gift for helping others. One day, a friend came over for coffee and I ended up helping her with some dating issues she was having. By the time she left she felt so much clearer about how to take action in her relationship that she insisted I teach a course on personal development and help others. She wasn’t the first person to nudge me in that direction—she was one of many—so I finally decided to follow through. The first weekend, my class was $15 and three girlfriends showed up. The next weekend it was nine women. It just kept growing from there. After a month or so, a writer for The New Yorker emailed me after hearing about my classes to see if she could interview me and it felt like another nod I was onto something really needed. I know a lot of people say this, but for me it’s really true. I didn’t choose entrepreneurship, entrepreneurship chose me. 


Burns: What was it like at the height of your business?

Macaluso-Gilmore: By 2012, I had a thriving six-figure business where 98% of my clients came to me through past client referrals. I also had 18 one-on-one clients per week with a waitlist of thirty-two women hoping to work privately. I believe the demand wasn’t for what I was teaching as much as how I was teaching. After taking my classes many clients wanted individual time with me, but I was maxed out and I didn’t know how to scale a one-to-one business like this. I was at a breaking point.

Burns: What made you step away from it all?

Macaluso-Gilmore: An ongoing feeling of overwhelm and a lack of clarity regarding what I wanted to do next. I was burned out, had two kids to take care of, a home I was in charge of and a husband who also had a busy business. I planned to step away for six months and give myself the time I needed to recharge. But six months turned into years. When I relaunched my company the first time in 2016, it didn’t work because I wasn’t still clear what I wanted. When you work for someone else, you most likely get promoted to higher positions over time. When you have your own company, you have to be vigilant about giving yourself raises and knowing what the next level up looks like. My price points were off and I still wasn’t sure how to scale in a way that was manageable as well as fulfilling to me—so I could make an even greater impact. 

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I was headed down the same path as before when a business coach I was working with helped me have a lightbulb moment. This was a second time in my life when I realized I had to be better about leading within my own life. I realized that instead of spreading myself thin by working with as many people as possible, I could focus solely on coaching women in positions of leadership and let the lessons they learned trickle down. I would be helping women leaders and those they lead. So I shifted to entirely serving this clientele, reworked my offerings, saved my sanity and maintained my mission by creating more vision, kindness and empathy from the top down.

Burns: How can women take the first steps to becoming leaders in their own life, like you?

Macaluso-Gilmore: The secret is to consciously and intentionally design your own life. The more uncertainty there is outside our front door, the more certainty we need to create in our own lives. I encourage women to do this by setting aside some time to create a daily routine that allows them to up their game. What’s your official bedtime? When do you need to wake up? How can you plan out nutrient-dense meals? What time will you stop working each day? These are critical questions.

I also show my clients how to get organized by prioritizing their tasks into an ABC To Do List every day. A’s are things that are most urgent and must get done that day, B’s are things up next or within that week, and C’s are things that can honestly wait. It’s a very calming tool because people tend to get overwhelmed looking at their entire list. 

Finally, I ask my clients to identify the biggest stressor in their life and find a fix for it with self-care. That’s not going to Bloomingdale’s and buying $200 jeans. If you’re not sleeping well, for example, it might be getting 8 hours of sleep and setting up a routine before bedtime to help you decompress. You have to prioritize your time to have a better life. For me, it was being overworked and overwhelmed. So I found a business model that better suited me and my life since having kids.

Burns: What does being a leader in our own lives make possible?

Macaluso-Gilmore: When I look at the state of discord in our world right now, I think, “We are so much better than this.” We’re surrounded by many leaders yet very few great ones. Not many in power know how to effectively communicate with others, navigate challenges with emotional intelligence, prioritize the greater good or achieve a healthier, more fulfilling version of success. 

The way we get to being “better than this” is to start with ourselves. When you develop the skills to create more tranquility in your own life, relationships and home, then—and only then—are you able to change our world. You lead by example for all those around you and inspire your small corner of our world.

I’m on a mission to create more great leaders who embrace new definitions of success because they know it’s alright to dream big—and equally OK to dream something small or different. Through my work, I help give women permission to drown out the noise around them so that they can tune into their own voice to hear what success is for them. If you give yourself permission to get quiet, I hope you, too, hear your own voice sharing what success looks like for you.

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