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Community Highlights: Meet Jennifer S. Heslop

Today we’d like to introduce you to Jennifer S. Heslop.

Hi Jennifer S., we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
I am a daughter to artistic parents. My mother was a dancer and nurse and my father, a singer. They traveled, performed and lived in many countries, had me in one of those countries. Always surrounded by unique people, landed in the US, attended my last year of high school in Brooklyn, NYC and then went on to graduate from college.

Wanting to work in the media, arts and entertainment industries was innate for me. They were the people that I was most comfortable with so I pursued working in radio, TV, record labels, clubs. I performed poetry, designed jewelry and T-shirts, sang on stage and wrote published articles.

After a bad work situation, I was a little traumatized and I decided to go back to school for sound engineering.

It was during this moment in my life that I felt the first calling to support others.

I was older than some of the students and one of only two women in the class. I would hang out with the students and just listen to their perspective on life, what they wanted, the city, their neighborhood, I was moved by their naiveness, their frustration, their anger, their hopelessness and hopefulness. Experiencing them inspired me to go and speak to the director to see if there were any positions available. Even though there was already someone in the Student Advisor position who was not showing up for the students, I wanted that position if it became available. I had no experience but I knew that it was what I should be doing.

I didn’t get it. I went back to TV production, a gig ended and while looking for another job, I saw an ad online for Career Advisor position at a school teaching makeup and hairstyling. I wrote a heartfelt bad a*s cover letter, expressing how much I wanted to guide their students. I had an interview and got the job.

I worked at the school for four years, advising young adults on the pursuit and protocol of a career and more than that, I would tell them who and what I saw in them. Really honest conversations with amazing human beings that I still hear from. They remind me of things I’ve said that have impacted their lives. I’m lucky to still receive affirmations. While working at the school, I also started my own consulting agency, motivateArt, focused on providing business support and guidance to artists and creatives.

Fast forward to moving to Miami four years ago. A NYC friend shared the contact info for one of his friends here in Miami and said I should call. I did and he referred me to a few of his connects in the media and art spaces. There were more referrals from the referrals:) Strangers who shared with me so quickly. Some having never even met me in person shared contacts with me. It was serendipitous when I met members of the Radical Partners team and then joined as one of their Leadership Coaches. Radical Partners is a game-changing social impact accelerator based in Miami that is run by a team of awe-inspiring women. Working with Radical partners has allowed me the opportunity to sit with South Florida’s quiet yet powerful and progressive social justice activists and nonprofit organizations. To be able to support and hold space for people who are fighting to protect and uplift the rights and humanity in others? It gives me great pleasure 🙂 . I’m a Certified Leadership Life Coach and under my company (JSH Coaching), I offer individual coaching, group coaching, workshops and products.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
It hasn’t been a smooth ride. I don’t even think that’s possible in life. And even though I believe in following the signs and opportunities that show up, it doesn’t mean they all turned out in my favor or were easy.

With any new job, career or industry you move into (or new State), first, there’s the time it takes to connect with people. In new spaces, there’s always an awkward trial period. People are checking you out, or not. You’re checking people out. Does the job/career/industry fit you and vice versus? Once you connect, then there’s the proving your value, then there’s the eventual acceleration that has to happen otherwise you will be overlooked or undervalued.

For most of my adult life, I’ve been a freelancer and an entrepreneur. “Smooth road” doesn’t even apply to that type of lifestyle! But because I’ve chosen that lifestyle, I am accustomed to the ebbs and flows. The goal is to learn from every experience and to get back up better.

I’m a mom as well and the stakes get higher when you are responsible for someone else. It has been challenging to continue to accomplish my goals at the speed that I would of, had I been childless. My daughter doesn’t understand when I’m on my computer working, from morning till evening, and sometimes I feel a twinge of guilt. However, I know my investment in her is the most important and I invest in my goals as well.

Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
I have had an extensive career in various roles and capacities and so my own experience in business guides some of my coaching but if I’m honest? I’m turned on by people who have an insatiable desire to accomplish their goals. I believe that those types of people, whether they know it or not, are trying to reach their highest potential. And I believe that potential exists in every single person. There’s a level of reciprocity that occurs with everyone I’ve coached. As we work together, I am fueled and motivated by their progress as well. I do more as I support others in doing more.

As a Leadership Coach, I truly enjoy helping leaders strengthen their businesses by helping them strengthen themselves. I find creative solutions to their organizational problems and I also create an encouraging environment where I guide and support them in overcoming emotional uncertainties to master their business and personal challenges.

What sets me apart is my ability to hear what’s not being said. My leadership coaching style is holistic which essentially means I hold space for all aspects of my client’s lives, including their personal lives, health and environment. If allowed, I’m going to ask about that, if it comes up that it may be the elephant in the room holding you back from success. My intention is only to hold a mirror up to my client by acknowledging them wholly.

I’m also a rider, your cheerleader. You want it? Let’s get it.

Brandwise? When starting motivateArt, my consulting agency, I reflected on all of the jobs I’d had up to that point. They were all support roles. I enjoyed paying attention to the detail, to the undertones. I enjoyed working on the bigger picture and working towards the bigger picture being a success. Where at one point I thought cheerleading so hard for others might have been a weakness, I recognized that its my superpower. Being of service to someone else, holding space for others, is my Super Power. So I’ve been consistent throughout my career and becoming a Leadership Coach is aligned with my role as a support and guide.

I’m a Leadership Life Coach and I offer individual coaching, group coaching, and workshops.

I also designed a 30-Day accountability workbook and planner titled “Damn It! I Don’t Want To! The No Bullsh-t Planner You need.” The Damn It! I Don’t Want To! planner is a tool of accountability. It will require you to look at your own behavior, the things you’re avoiding, the things you want to do and you will have to look at the things you don’t want to do, over and over again until you deal with it or deal with why you are avoiding it. It’s a unique system that encourages honesty and accountability.

The Workbook/Planner is available on Amazon.

Along with “Damn It! I Don’t Want To! The No Bullsh-t Organizational Planner You Need”, I’ve also developed the “Damn It! I Don’t Want To! Workshop to accompany the book. The workshop, held monthly, is interactive and intimate in the sense that I prefer to engage with a small group of participants, a maximum of 20. Information and tickets are available on Eventbrite.

How do you define success?
Success, for me, is getting back up when you’ve fallen. It’s continually training your mind and training your will.

Success is going after something and being dogged about it until YOU say it’s done and not allowing any person, place or thing to decide when you’re done.

Success is being an individual and being considered a freak by a world full of conformists.

Success is being authentic, seeking that authenticity from yourself and just walking in that sh*t, head up.

Success is doing the work because concerted effort always yields results. Success is doing this life thing, aging thing, full of unknowns thing, with grace.

Success for me is continually growing and evolving, being flexible and open to changing.

Contact Info:

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