Today we’d like to introduce you to Jill Monson

Hi Jill, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.

I skipped my senior year of high school with the perimeter that I had to attend a community college. My only life dream (mind you, I was only 17 years old but knew exactly what I wanted for my WHOLE life) was to work in radio. So when I started working at the college radio station, for the first time, I felt like I belonged.

Shortly after I weaseled my way into an internship at a commercial radio station. These were the “old days” when you didn’t need college credit and there really weren’t a lot of rules. This meant I filed and sorted quite a bit, but it also gave me exposure to the thing I loved most – the radio industry. Eventually I was there so much the boss gave me a few bucks an hour to run a syndicated show on Sunday morning. One day the DJ who was on after the recorded portion ended wasn’t going to be able to come in and I had my first chance to go on-air. And a star was born! Uhhh – totally kidding, rather a silly kids dream deepened and for many years to follow I would continue on my radio journey. First part-time overnight shift, the full-time overnights, and then I was given the chance to do the traffic reporting (literally drive around the city in a station wagon with a police scanner and report what was going on) for the morning show. I went on to do other shifts and moved to different markets, however I was also realizing the dream didn’t pay that well and so I also waited tables for many years. I also dabbled in sales and marketing while at my various stations.

In time I ended up back in the area I grew up in and stayed in the industry but shifted roles becoming the Marketing Director. I loved this position and would have continued but was given the opportunity to try the one on-air position I had never done – co-host of a morning show. As I reflect that was simultaneously one of my favorite and least favorite times in radio. I loved the work. I despised my co-host. He was from the deep south originally and let’s just say we had very differing opinions on what women should talk about and ultimately after a year (his contract was longer than mine) I was let go.

I had to grieve because the one thing I loved was no longer feasible. I also didn’t have a degree because even though I started college, I had dropped out to pursue radio. Now, never having been fired from anything, I faced a major life moment. I decided to go all in – I went back to college while working four part-time jobs and eventually at 30 years old, I graduated with my bachelor’s degree in communications and had saved enough money that as a single woman I bought a house.

But then what? I ended up going into retail management. Discovering quickly that was NOT my jam, I pivoted into a sales position for a coupon advertising mailer. I did well financially, I was promoted to manager, but ultimately, I wasn’t fulfilled. That was when my mother, who had already battled lung and brain cancer in her earlier years, passed away. She was only 55 years old and to say it shook me would be a complete understatement. I ended up deciding my legacy could not be 50% off dry cleaning and I resigned from selling coupons. I decided then that I wanted to open a marketing agency but I knew I also needed to be responsible. I chose to work for a client who owned a major roofing company as the Director of Marketing, with the understanding it was for one year while I grew my business.

And one year later, renting a desk in a friend’s office, I began Inspired Marketing as a full-time endeavor. The company grew over the years and was a successful and award-winning full-service marketing and event planning company. My team (and office) grew and we served a vast array of clients in lots of industries including home improvement, financial planning, higher education, IT, fuel services, firearm manufacturing, and more.

Sadly my health declined and the stress of the company was too much so I downsized. I continued in a consultative role for many years while also working full-time for MGM Springfield and then the American Cancer Society.

In 2020, after having a near death experience, I had another major life moment. I chose to take these past few years to assess and reflect and last year I began a new company called POP!more, which is confidence coaching, training, and speaking… done differently! Plus, as a way to continue with my passion for marketing and events, I joined Chikmedia as the part-time Associate Director of Marketing.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?

It has been the farthest thing from a smooth road, but today, I realize that every pothole on my road has made me a better me than I ever knew possible.

I think the biggest struggle was losing my Mom. I mentioned earlier that she passed rather young. She had been a single mom for many years and we were super close. Not having her left me feeling lost and truthfully, as someone who has always felt a bit “different”, not having the person who loved you unconditionally made me feel very lonely.

Additionally I have always struggled with confidence (and yes, I do realize the irony given my new company). I have been overweight most of my life. I was teased when I was younger, made poor decisions with relationships because I devalued myself and my body, and then felt it held me back professionally. Like it or not, there is a stigma that overweight professionals are not as – fill in the blank – as those who present more together. I believe I lost bids because when push came to shove, the contract went to the agency who had a leader who looked the part.

It is hard to point out specific struggles and also be brief. I can however share that I am a thriver (I use that instead of survivor) of domestic violence, I have nearly had to file bankruptcy, I was bullied to the extent of trauma by a former supervisor, and I struggle with an eating disorder. These are just a few examples of struggles but like the sign over my TV says, “When you stumble in life, make it part of your dance.” So I welcome and embrace each one as it comes.

Thanks for sharing that. So, maybe next you can tell us a bit more about your business?

I created POP!more, driven by a mission to empower others to embrace their true selves. POP!more is confidence coaching, training, and speaking… done differently! This disruptive model 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

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!

I considered what I am known for and what sets me apart from others and decided it easiest to share a few comments in the feedback from the most recent group I trained. Comments included:

* I never laughed so much during training. You keep me interested and engaged.
* I want to thank you for the wonderful time at the training. I usually don’t enjoy training, but I when I attend yours, it’s always a learning experience and I have a good time.
* I love Jill’s energy and positive aura.
* Jill is fun, real and makes learning exciting
* I love how Jill connects with everyone.
* You are amazing. Your training really makes us dig deep to understand ourselves and just makes me want to be a better person! Thank you for everything and your time!

Where do you see things going in the next 5-10 years?

In general the coaching industry saw a large growth spurt during and post COVID. I think in some cases there will be some thinning of the more “fly-by-night” companies, however I think overall the need for coaching specifically in the soft skills area is poised for significant growth and evolution.

Regarding shifts, changes, and trends, I think there will be a continued focus on mental health and that confidence coaching may become more integrated with overall mental wellness programs. One possibility is increased collaboration with therapists and mental health professionals.

As more companies recognize the value of employee confidence and resilience this industry may become a more critical component in professional development programs, aimed at enhancing workplace culture and productivity.

In addition, coaching that specifically addresses confidence issues faced by underrepresented groups may gain prominence. This shift will foster a more inclusive approach to personal and professional development.

Lastly, I expect to see more integration with technology with the use of apps and online increasing. Examples of this may include more virtual coaching applications, AI-driven assessments, and gamified learning experiences.

Contact Info:

• Website: https://www.popmorenow.com
• Instagram: https://www.instagram.com/jillmonson_popmore
• Facebook: https://www.facebook.com/popmorenow
• Other: https://www.chikmedia.us/

Image Credits

“chris marion — used Canvas Rebel Oct 2024” should be credited: Chris Marion Photography.

“College class — Canvas Rebel October 2024” should be credited: Western New England University course with Professor Brenda Garton-Sjoberg

“Speaking to youth — Canvas Rebel October 2024” should be credited: Ohana School of Performing Arts during ‘Beautiful Inside & Out’ kids summer camp