In this interview, communications strategist, performer, and educator Karen Louisa Gross shares how community has shaped every stage of her entrepreneurial journey, why success is something we each have the power to define for ourselves, and how embracing an unconventional path can become your greatest strength. She reflects on the realities of creative entrepreneurship, the lessons she’s learned about leadership and financial discipline, and why vulnerability, connection, and giving yourself permission to live life on your own terms are at the heart of building a meaningful legacy.
The Right Community Gives You Courage to Dream Bigger
How has community been a part of your journey as you have grown and established your business and your leadership?
Community is everything. Although I tend to work alone in my business, I feel deeply nourished by community because you cannot grow without support. You can’t grow without mentorship, and you can’t grow without other people who are in the struggle with you.
Years ago, that looked like going to open mic nights with other songwriters, people who were also figuring out how to write songs and navigate the music world and the business. You connect with people, and you find people to collaborate with. As I focused more on women’s creative entrepreneurship, I realized we have so much to learn from one another. I am constantly learning how to be a better, more successful creative entrepreneur myself.
During the 2021 lockdown, I launched the She Rocked It media and mentorship platform to help women connect, share how to build their dream creative businesses, and learn from one another’s journeys, not just the successes, but the struggles of how we actually got there. The road to realizing your dreams is fascinating for every woman.
Being a creative can be a roller coaster, honestly. We have a lot to learn from each other as we ride the waves, support one another, and cheer each other on to keep going and fight the good fight. We are intentionally, proactively creating our lives, not just being creative in our work. I actually came up with the whole vision for She Rocked It during lockdown while participating in a mastermind program for entrepreneurs. Within that community, I found the vision and the courage to build it. If I had been by myself, I wouldn’t have had the accountability, the resources, or the sounding boards to even conceive it. Community holds me accountable. If I verbalize a goal to others, I know I have to do it.
Success Begins When You Choose Your Own Definition of Happiness
What does your dream life look like? And are you living it?
First, there’s that lightning-bolt moment when you realize, “Wait, I have the agency to design my own life.” That is a huge realization, because it’s easy to find yourself on a path you didn’t consciously choose, one dictated by a series of “I have to do this, I have to get a full-time job, I have to get married, I have to have kids.”
I’ve bucked a lot of those expectations in my life. I’m 46, I’ve never been married, and I don’t have kids although I’m a proud auntie and cat mom. There is absolutely no judgment in that. I love women who choose kids, pets, traditional partnerships, or no partnerships at all. Every woman should have the opportunity and the agency to choose what her dream life looks like. I may at some point decide to do a 180-turn, get married, and have a family. Our vision of happiness can evolve over the years. It isn’t a static thing.
Calling myself a creative entrepreneur for nearly 13 years feels like a dream come true. I dreamed for a long time of running my own business. I am deeply grateful to be a multi-hyphenate entrepreneur and to be able to make a living through combining my passions for communication, music, and mentorship. I am proud to have collaborated on communications with some of the nation’s most influential leaders and organizations, and to have spoken at top global conferences including the International Association of Business Communicators and the Professional Speechwriters Association. I’m honored and humbled to be a respected voice in the communications field, known for my signature Communication That Sings™ approach that inspires, informs, and activates audiences.
Also, I genuinely love my clients. Of course, I have financial goals, and those are very important to me. But ultimately, success looks like waking up and loving what I’m doing that day, and loving who I’m doing it with.
One thing I am actively working toward is getting back on stage more and exercising that part of myself. After the lockdown and COVID, I retreated a bit from the stage. So stay tuned for more of that. I’m also sharing my voice more visibly and vulnerably on social media and Substack. Success is always evolving. As an entrepreneur, I am constantly writing down what it looks like. It’s a process of constant introspection, and then trying to outwardly make it happen.
The Daily Practices That Keep Creativity and Confidence Alive
What are some of the habits that allow you to reach that definition of success?
I am constantly reflecting on and refining my habits. Eight years ago, I moved from New York City to the country. I am originally from Bucks County, Pennsylvania; I ran away from the country years ago to live in Philadelphia and New York, but I eventually rediscovered the beauty of nature. One habit that has remained consistent for the past several years is connecting with the outdoors. Nature is a great teacher and very grounding. I find a lot of inner peace and learn so much just by walking outside.
I also view meditation as my little cheat code. I tell my students at Temple University that before you go on stage or before you face a big morning, you should get on an app and meditate. It completely changes how you show up. As a singer, it gets you into your body and helps you control your breath. I highly recommend even just a little bit of meditation alongside connecting with nature; I need that green space, fresh air, and wildlife to put me in a better headspace. It truly helps my mental and physical well-being.
Additionally, though I am not traditionally a gym girl, I recently started strength training with a personal trainer at a gym called The Edge. Now that I’m 46, I know I need to keep my body strong. Strength training is a great teacher because it pushes you physically in the exact same way that leadership pushes you, or the way working hard on a project pushes you. When you have to endure physical discomfort, it builds the discipline you need to tackle the less glamorous parts of entrepreneurship. You just have to fight through it and show up. Ultimately, I feel more energetic and vibrant after a good workout.
Finally, I focus on fueling my body positively, but without getting obsessive. I don’t like to obsess over numbers and weight, been there and done that. Taking good care of your physical well-being is an important habit that I’m still actively cultivating this year.
Why Community Helps Women Break Free from Feeling Stuck
What is it that holds women back from taking opportunities that might lead them to a life they love?
Unfortunately, women can easily get stuck. I meet too many women who say, “I just don’t like where I am, but I don’t know how to get my foot out of the mud.” That is exactly why I created She Rocked It, and why platforms like Habituelle are so important. When women see the stories you are presenting, they learn what is possible. If women are isolated and don’t find these platforms or hear these stories, they may not even know that other roads exist.
I fundamentally believe that when women gather in community, share the same rooms, let their hair down, and speak candidly about their journeys, that is when we open doors for one another. Isolation makes gaining momentum a lot harder. We need more spaces like this, especially in-real-life events.
I recently attended an event in Philadelphia hosted by the Committee of 70 celebrating women in public leadership. Looking at the panel of women judges, activists, government officials, and TV personalities gave everyone a jolt of inspiration. Even if you didn’t see yourself exactly in their shoes, it gave you hope.
The truth of the matter is, there is still a significant gap in women’s leadership. I’m a member of The Forum of Executive Women in Philadelphia, and their annual reports consistently show a major gap in the number of women occupying executive roles.
I think another thing holding women back is the idea that leadership has to look a certain way. I show up as a creative, and I own that style of leadership. Did I ever think a singer would be in The Forum of Executive Women? No. But leadership can take unique forms. It doesn’t always have to be a power suit, which stems from a traditionally masculine mold of leadership.
Women should get comfortable with redefining leadership. When I see women rocking their own cool style and energy, I see a new definition of leadership emerging. We can take that leap, get out of our stuck places, and redefine leadership, not just superficially, but fundamentally. Maybe leadership is about listening more than talking. Maybe it’s about compassion. Maybe it’s about reading the room just as much as you read the data. You can do both, but as women, we bring essential soft skills to the table that are vital to good leadership.
Financial Discipline Is Just as Important as Creative Vision
What is a hard lesson that you’ve had to learn so far on your journey?
One incredibly hard lesson has been cash flow management. As an entrepreneur, when you don’t have a steady paycheck, you have to view money differently. You have to have discipline.
As a creative, I love to buy cool equipment and hire talented people to collaborate with me, but you have to be careful with your cash flow. You also have to remember to set aside enough money for taxes. I am 13 years into entrepreneurship, and I’ll be honest: last year was my biggest year in business yet. My accountant warned me, but when that tax bill arrived, I was shocked. You have to tuck that money for taxes aside, and not touch it. I try to instill this financial order in my students from the very beginning. And if finances aren’t your strength, get someone to help you. I told my accountant that he needs to be like my personal trainer going forward; we need quarterly meetings to ensure I am entirely on track so I never find myself freaking out again.
You need to be self-aware enough to know your strengths and weaknesses as a business owner. If your strength lies in being the creative visionary, the person on stage, and the one helping clients, then try to get support managing the dollars so you don’t put yourself in a tight spot. Entrepreneurs can blow through capital quickly, so you also have to be careful with credit cards and loans, because you still have to pay the piper back.
Ultimately, you have to do the soul-searching to know if you are comfortable with the entrepreneurial ride which can ebb and flow. Some people prefer a steady, reliable paycheck every two weeks. If that’s you, that is completely fine, just know that about yourself.
Giving Others Permission to Build a Life That Feels Authentic
What is the legacy that you hope to leave behind?
I hope that by showing up as my unapologetic, creative, unconventional self, I give someone else permission to do the same. I want people to look at my journey and say, “She figured out a way to live a creative life sustainably and on her own terms; maybe I can create a life that feels good and share my voice, too.”
Vulnerability has been a throughline in my career. One of my most rewarding creative experiences was writing a very honest column about my life for my college newspaper. Now, I write the She Rocked It Substack, where I share candidly about being a creative, unconventional Gen X woman navigating aging and other realities of the mid-40s.
Ultimately, “Communication That Sings” has to start with me. If I can raise my voice honestly and impactfully, I hope it helps my clients, my students, and others to do the same. I have to walk the talk. Whether it’s through singing or writing, if I show up as a real, flesh-and-blood, warts-and-all person, I give others permission to be real, too.
This current chapter of teaching at a university and supporting younger people as they navigate their paths has felt deeply moving in terms of legacy. If I can help a student feel more confident in their life path, that is a success. Even if they come out of my class realizing entrepreneurship isn’t for them, that is still a great, valuable lesson.
Most of all, I want to make it fun for students to think about their futures. There is so much heaviness, pressure, and uncertainty in the world right now for young people trying to plan out their lives. If I can give them some good news and say, “Hey, you can be proactive about creating a life for yourself. It won’t always be easy, and there will be struggles, but that is what community is for—we will figure it out together.” I am still figuring it out every single year, but we can do it together and build something cool.
About Karen Louisa Gross
Whether she’s onstage sharing her own voice, or behind the scenes helping leaders share theirs, Karen Louisa Gross is guided by one principle: Communication That Sings™. As an in-demand performer and communications professional for over two decades, Karen is an established expert on connecting with audiences in ways that resonate, activate, inform, and inspire. Since 2013, she has served as a trusted communications consultant for C-suite executives, founders, entrepreneurs, media personalities, and leading organizations across industries. Drawing on her background as a journalist, speechwriter, publicist, and performer, she helps clients develop thought leadership, strengthen internal and external communications, and deliver high-stakes presentations with clarity and confidence.
Beyond consulting, Karen is an accomplished keynote speaker, emcee, and vocalist with more than 20 years of onstage experience at premier venues, theaters, and events. She is a member of the Professional Speechwriters Association and the International Association of Business Communicators, and has been a featured speaker at both organizations’ global conferences. Karen is deeply committed to mentoring others on creative entrepreneurship. She serves as an adjunct faculty member at Temple University’s Klein College of Media and Communication, where she teaches media entrepreneurship and guides students in aligning their creativity with their careers. For more information or to collaborate with Karen, visit communicationthatsings.com.
Habituelle is proud to partner with the Fitler Club on The Stories—a shared commitment to elevating the voices of women leaders and creating space for the conversations, connections, and stories that inspire meaningful change.
