We caught up with the brilliant and insightful Jill Monson a few weeks ago and have shared our conversation below.

Hi Jill, thanks for joining us today. Let’s kick things off with your mission – what is it and what’s the story behind why it’s your mission?

After owning a previous company for a decade and letting it run me into the ground, both emotionally and physically, I made the decision to shift gears and pursue a career in non-profit fundraising and donor relations, an area close to my heart. However, my health continued to deteriorate; by early 2020, I weighed 330 pounds.

While I was out delivering food (always a girl with a side hustle) I fell and tore my Achilles tendon, requiring surgery and extensive physical therapy. Things took a critical turn when a routine check-up with the surgeon revealed the possibility of a blood clot. I was off to the hospital to get checked and I was not thrilled, for many reasons, the biggest being there was this icky virus thing going around that was killing people.

I ended up being admitted and was told that Saturday that I had a full left leg blood clot and a “butterfly” clot branching into both lungs, and that if I wasn’t at the hospital… I would have been DEAD BY MONDAY!

Yet even this profound wake-up call didn’t immediately push me to make significant changes.

I returned to work, happy to do so in a role that aligned with my passion, however I continued to find a lack of supportive leadership. Don’t get me wrong, the health insurance was a wonderful benefit but ultimately, despite my dedication and passion, after facing unfounded accusations of aggression and hostility, I realized I couldn’t compromise who I was any longer.

With uncertainty looming, I resolved to DESIGN the life I wanted. That’s when I founded POP!more, driven by a mission to empower others to embrace their true selves. Through personalized coaching, I help people of all backgrounds, ages, and stages, cultivate confidence and celebrate their unique strengths. Whether introverted or extroverted, regardless if they’re tall or short, big or small, everyone deserves to thrive and find fulfillment. Together, we celebrate personal growth, acceptance, and the joy of being authentically oneself.

My goal is to foster a community where self-acceptance and mutual respect reign, where every achievement, no matter how small, is cherished. At POP!more, we champion the idea that every individual is PERFECTLY IMPERFECT!

Jill, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’m someone who is very proud of my “reputation”. I am known for being genuine, loyal, & having zest for life. I’m a natural born connector (some call it my superpower). I have been told people leave conversations with me feeling better than when they arrived, which is deeply fulfilling for me.

Before founding POP!more, I successfully ran Inspired Marketing, an award-winning agency specializing in full-service marketing and event planning across diverse industries such as home improvement, finance, education, and more.

Currently, alongside POP!more, I serve as part-time Associate Director of Marketing at Chikmedia, where I continue to indulge my passion for marketing and events. My career spans roles in non-profits, hospitality, and even as a radio personality at stations across New England.

Community engagement is vital to me, reflecting my commitment to causes like early education, domestic violence awareness (as a thriver), food security, and health and wellness. I also was an original board member and served as co-Vice President of the Young Professional Society of Greater Springfield, underscoring my dedication to community leadership.

My educational journey began unconventionally, skipping my senior year of high school to earn an associate degree in Communications, followed by degrees in Communication and Media Studies and an MBA in Entrepreneurial Thinking and Innovative Practices. I’ve also pursued ongoing learning through certifications and courses in major gift fundraising and leadership development.

Recognition has been humbling, including accolades like the Ad Club of Western MA Creative Award and BusinessWest 40 Under 40. However, my most cherished awards are the Better Business Bureau Marketplace Ethics Award and Western MA Women’s Magazine honors for event planning excellence.

Beyond my career, my greatest joy is my family life with my wife Jen and our three rescue pets. Together, we cherish moments dancing in the kitchen, enjoying movies, and spending time with our nephews. When I’m not coaching or speaking, you’ll find me on our porch with a coffee and a good book.

As for POP!more, I describe it as confidence coaching and training… done differently! This disruptive model of one-to-one and group coaching, training, and speaking means there’s no fluff, no deep breathing, & no B.S. The focus instead is on practical, actionable steps that empower clients to discover their authentic selves and cultivate lasting confidence. This personalized, transformative approach helps individuals enhance communication, interpersonal skills, and overall fulfillment.

Why did I name the company POP!more? It reflects my belief that everyone deserves to confidently embrace who they are and live their fullest life. It’s about empowering others to show up authentically and POP!more in every aspect of their personal and professional journey.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

There have been numerous lessons I’ve had to unlearn, but two interconnected ones stand out: the need to control everything and the desire for universal approval.

I’ve always been a planner at heart. I believed I could orchestrate outcomes, from dinner plans to client responses to weather conditions for events. This need for control traces back to my upbringing with divorced parents and a feeling of powerlessness, which fueled my craving for stability through meticulous planning. When my mother battled cancer during my young adulthood, the uncertainty deepened my reliance on control as a coping mechanism.

Similarly, being raised by a single mother who I felt prioritized being liked by everyone instilled in me a deep-seated desire for universal approval. Moving frequently during my school years forced me to adapt and mold myself to fit in, intensifying my need for acceptance.

These struggles with control and approval manifested in an eating disorder that plagued me for years. I sacrificed my well-being to conform and gain acceptance, using food as a crutch when faced with rejection.

Through therapy, the support of loved ones, and personal growth, I’ve started to unlearn these lessons. I now embrace the mantra that I can only manage my own actions (“keeping my side of the street clean”), and I’ve come to accept that “not everyone is going to like you,” as my dad wisely put it (or as I like to say “what other people think about me is none of my business”).

I recognize I am still a work-in-progress but these revelations have allowed me to focus on self-acceptance and personal growth, both personally and professionally. And as I would tell a client, just by practicing these new habits, I’ve already won!

Any stories or insights that might help us understand how you’ve built such a strong reputation?

Authenticity is at the core of my reputation. I am unabashedly myself, knowing that I won’t resonate with everyone (I’m certainly not everyone’s cup of tea, and honestly that’s because I’m more of a latte) and that’s perfectly okay. I show up consistently, deliver on my promises, work hard, and face challenges head on. I acknowledge my imperfections while leveraging my strengths, I’m not afraid to fall down and get back up, dust myself off and try again.

Whether in business or personal interactions, my approach to building relationships is rooted in empathy and transparency. I strive to foster a genuine connection with those around me. I prioritize authenticity, which builds trust and respect. I believe living authentically is the cornerstone of my reputation, defining how I engage with others and leaving a lasting impression in my market.

Contact Info:

• Website: https://www.popmorenow.com
• Instagram: https://www.instagram.com/jillmonson_popmore
• Facebook: https://www.facebook.com/popmorenow
• Linkedin: https://www.linkedin.com/in/jillmonson

Image Credits

Chris Marion Photography
Hillary Lynn Photography