We caught up with the brilliant and insightful Jamessina Hille a few weeks ago and have shared our conversation below.
Jamessina, looking forward to hearing all of your stories today. Let’s go back in time to when you were an intern or apprentice – what’s an interesting story you can share from that stage of your career?
I was the first intern of the Youth Football Department of The National Football League in the early 2000s. The offices at that time started on the 12th floor and ended on the 17th, which we insiders called ‘The Field of Dreams’. It was here the Youth Football Department called home and was where the Commissioner’s office was located with a spiral floating glass staircase, a large board room, and a receptionist area filled with Super Bowl trophies and championship rings. Commissioner Tagliabue was at the helm at the time, and set a strategic initiative of serving 10 million youth by 2010. The Youth Football Department was in its early prime, even having hosted Snoop Dogg in a meeting with the Commissioner and Ridell to discuss helmet design improvement for our young athletes.
My first boss was the Senior Director of Youth Football, who taught me real quick how to operate in ‘the real world’ and provided life and work lessons that I return to quite often after 22 years. A few weeks into my role, I had an idea, and walked to his office door to share it with him, where he was sitting quietly, heads down at a notepad. I began with a bubbly, “Scott, I have the best idea for the upcoming event, and I’d love to brainstorm with you…” He looked up at me standing in the threshold of his office and said, ‘I am busy. If you cannot tell me in 30 seconds what your objective is, please schedule time with me instead.’ Ah, that response shook me, yet back at my desk I crafted a memo that identified the problem, a possible solution, and the requirements needed to bring it to life. He taught me the value of a well constructed idea, how to engage leadership with the right business acumen, and to deliver my best work every time.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
Until a few years back, I was a shiny, happy, stiletto wearing professional, checking boxes off of my success list in pursuit of an executive title. A daughter of entrepreneurs, I was raised to be a corporate woman, to pursue achievement, and go after what I wanted with fervor. I painstakingly created an identity to fit the role, complete with a signature pencil skirt and popped collar. I took great care in listening and learning from my predominantly male sphere of influence, as they took me along with them on the mission to achieve quotas, build the brand, and launch the idea. I got married, landed my dream job, had two children, moved to a beautiful coastal town, received the coveted Vice President title – and then I broke.
Sitting around a dinner table with dear friends, sober, relaxed, and happy, I suddenly grabbed my chest in agony. My heart felt as though it would burst, shooting pain through my shoulder initiating thoughts of the attorney who had our will on file in NY. After hours in the emergency room, I was sent home as a healthy individual who was experiencing deep stress induced anxiety. It was my third episode in three years – it was time to make a dramatic change.
There was a deep fissure in my being- cracking my finely tuned facade in half, unveiling the rigid, burnt out, unhappy woman who realized the pursuit of a plan created 20 years ago no longer serves her. I had not felt like myself in a long time, but hid behind being busy so as to avoid the pain of not knowing who I was anymore, or what I was passionate about. I felt as though I had missed out on being fully present for my family, prioritizing climbing the ladder rather than enjoying what I was building.
My overachieving, breadwinning girlfriends felt the same, I learned. They, too had experienced panic attacks, stress induced ER visits, or depression. The demands of realizing the coveted duality of successful executive and doting mother/wife/partner/homemaker was hurting us mentally and physically. This had been stirring for years inside and is now a five alarm fire, causing women to silently quit or be part of the great breakup. The vision we had been promised had been achieved, our wins celebrated in a personal imaginary trophy room. However, how could our male champions along the way even begin to express what it would be like for us to create and sustain humans and a home while sprinting towards the corner office?
The few women I worked for were on their own mission to achieve, earn, and climb while figuring out the formula for success. It wasn’t that they failed to mention this unsettled crack in our facade, rather they were trying to keep pace and keep face for their own pursuits to break the glass ceiling.
Even now with the shattered glass, there is not a clear answer, nor much change in industries, to support biological women and the pursuit of a dual role as executive and mother.
So I set out to heal my spirit, heal my marriage, and ensure that I did not end up a wealthy, lonely woman whose loved ones would enjoy the life I created without me. I decided it was time to burn the success list, and rekindle what I truly desired at this phase of my life. And it must include space to thrive in my career while devoting time and energy to bring back that passionate, breathless girl who went after what she wanted- and enjoyed it.
So, I wrote it all down- in notebooks on a plane, in my notes app, transcribed from voice memos- and penned “Burn the Success List: A Love Letter to Overachieving Corporate Women.”

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
My worth is not based on my attainment of career milestones.
The adrenaline rush of winning can sustain you for a while. The gratification and accolades of achieving a target, or closing the deal, or the full bonus payout keep you pushing harder and further to build more wealth and create a lifestyle we are supposed to covet. We begin to feel a bit alien at home as our stress level heightens with the self-inflicted demands of our career pursuits and we admittedly find ourselves at the laptop or office later that usual. We find it hard to relax, rest, or play. Always on, the moments of rest leave us feeling guilty that we aren’t producing.
How ridiculous this sounds, and yet, we find ourselves reaching for the space in between our neck and shoulder as our bodies resort to pain to alert us that something is not okay.
Seven years ago I was asked to guest lecture at the College of Charleston for the MBA program incoming cohort on ‘career envisioning.’ My impressive resume and journey to become a female marketing leader in enterprise technology was something to talk about. Instead – I taught the class to unlearn the lessons we’ve all been told.
Get the degree, get the job, get married, buy the house, have the baby, get the promotion, go on the vacation, the success list goes on and on. And we check off each box with a smile.
This list is not the important one. Yes, it is tied to dreams we once had as we prepared for what we would do with our life and talents. Yes, it is how we earn our living and sustain a life for those we love. So do what we need to do, but burn that success list.
Instead, create a mental inventory of the moments that are emblazoned in your mind, give you a rush, warms your heart so it feels that it may burst, and perhaps bring a tear to your eye. The sweet pouty mouth of your newborn in your arms, the quiet dinner in the kitchen by candlelight with the one you love, birds chirping in the spring in the backyard, the glow of the full moon through your bedroom window, riding a wave in the ocean, the sun on your face, your own laughter, a walk with your best girlfriend, your mom at the kitchen table, your favorite song.
Instead, start your day with something just for you, connecting with yourself deeply. Stretching, walking, meditating, warm tea and a book, a sweaty workout, a swim, a simple moment of gratitude – ‘I am everything I need.’
Instead, give a closer look to how to work smarter, automate or delegate, or both, and draw a fat black marker line in your planner when work will be done each day. Unlearn the stress inducing, mind numbing roadmap of ‘wins.’ Trust that you will still win, you will still achieve. But with a full heart, a passion for getting back to those you love, and an evolved realization that we are masterful at living this beautiful gift of life.
By teaching, I was learning. I wanted to embody the beautiful life I was lecturing. And every day, I’m getting better at it.

How’d you build such a strong reputation within your market?
I am a creator, a collaborator, and believe in creating mutual beneficial outcomes. I ask for the best possible work from my team members, and they in return expect that from me. A reputation is the average impression your peers, colleagues, and community have of you. A good one requires consistency and honesty- and requires being visible to your desired market, creating value and sparking ideas. I put myself in many different environments with different humans for the purpose of simply connecting.
I am not pursuing perfection, rather I believe that my value is in delivering a personalized experience no matter how many people are in the room. One reputation can carry you across markets. Your network becomes your champion.
Contact Info:
- Website: https://www.burnthesuccesslist.com
- Instagram: iamjamessina
- Linkedin: https://www.linkedin.com/in/jamessinahille

Image Credits
Erin Turner

