Jennifer S. Heslop of JSH Coaching: “Be flexible”

Be flexible– bend, don’t break. It begins with a deep belief that there is a way through, that there is a “light” at the end of the tunnel, that the outcome may not be as you imagined but could possibly be even better. In this interview series, we are exploring the subject of resilience among successful […]

Thrive Global invites voices from many spheres to share their perspectives on our Community platform. Community stories are not commissioned by our editorial team, and opinions expressed by Community contributors do not reflect the opinions of Thrive Global or its employees. More information on our Community guidelines is available here.

Be flexible– bend, don’t break. It begins with a deep belief that there is a way through, that there is a “light” at the end of the tunnel, that the outcome may not be as you imagined but could possibly be even better.


In this interview series, we are exploring the subject of resilience among successful leaders. Resilience is one characteristic that many successful leaders share in common, and in many cases, it is the most important trait necessary to survive and thrive in today’s complex market.

I had the pleasure of interviewing Leadership Life Coach Jennifer S. Heslop.

Leadership Coach Jennifer Heslop helps leaders strengthen themselves and their businesses by creating a safe and encouraging environment where they overcome emotional uncertainties to master their business and personal challenges.


Thank you so much for joining us! Our readers would love to get to know you a bit better. Can you tell us a bit about your backstory?

I am the daughter of 2 artistic parents from the Caribbean. My mother, a Trinidadian, was a dancer and my father, a Jamaican, was a singer when they met in Europe. I was born in Germany and lived in a few countries, always surrounded by creative, artistic people. We had moved to my mother’s birthplace, and when it became time to think about colleges my mom asked where I wanted to go. I said America, because my favorite cousin lived here. So I moved to New York City and did my last year of high school, graduated and went on to college.

My career experience has been a mix of freelancing and entrepreneurial pursuits, including working in radio, TV, at record labels and music clubs, becoming an amateur wedding photographer and starting my own PR company. One of my jobs was as a career advisor at a trade school and that put me on the course to really claiming my role as a Leadership Coach. It was here that I really began connecting with people on a deeper level, guiding and supporting them, not only through school and their career, but who they were and who they wanted to become.

While at the school, I founded motivateArt, a creative consulting agency focused on providing support for Artists. Looking back, I was always trying to combine the various business skills I had with the mentoring and coaching skills that are innate to me.

Fast forward, I moved to Miami 4 years ago and initially focused on finding my way in the arts industry here but because I’ve always stayed open to letting the opportunities guide me, I am now a Leadership Coach under my own company working with some of South Florida’s Non Profit Leaders.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

Most of my career was full of serendipitous moments that I just flowed with, landing positions that I wasn’t seeking.`TV Production manager, live music club PR, radio production are some of the positions I held. I wasn’t wandering through my career but I never had a strategy or plan in place. I was never looking for a specific outcome so I enjoyed the roles I held but didn’t take advantage of them or intentionally leverage them. As you get older you start respecting time a little more:) so I have become a much more conscientious participant in my career trajectory. I plan more, I set goals with timelines more, and I’m more self aware, facing my weaknesses and addressing them.

I was offered opportunities that I had no experience for and because I had no plan or goal, I even turned down opportunities because they required me to assume roles I never imagined for myself. At one of the radio stations I worked at, the program director came to me and asked whether I was interested in being on-air. At that time I was an intern. No program director of any radio station goes to an intern and asks if they’re interested in one of the most coveted roles on radio. I said no. It was just not anything I ever thought of doing. Now I look back, I recognize that sometimes people see in you what you never imagined and that maybe sometimes you’re supposed to say yes and just be guided somewhere new.

What do you think makes your organization stand out? Can you share a story?

My leadership coaching style is holistic and I’m also an empath which essentially means I hold space for all aspects of my clients’ lives, including their personal lives, health and environment. Some of my clients are super goal focused and want an accountability partner and a kick in the ass, so they tend to try to separate or compartmentalize aspects of themselves when coming to a coaching session but most of the time, I can feel their lack of energy or shifts in energy. If allowed, I’m going to ask about that. My intention is only to hold a mirror up to my client by acknowledging them wholly.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I’m a little poetic about that. I believe every person that is in my life has impacted my life, whether negatively or positively. I am here because of the experiences and relationships I’ve grown in. But my mother has been and remains the person that takes all of the credit. Everything she has done for me throughout my life has impacted how I see myself and my inner awareness and confidence but it’s her always telling me “hold your head up”, “when you shake someone’s hand, be firm and look them in their eyes”, “no one is better than you” and the one saying that I move with in every second of the day- “and Jennie don’t forget who you are”. I say the same words to my daughter as I watch her growing into who she’s going to be. I’m forever grateful for my mother.

Ok thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the trait of resilience. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

I define resilience as the ability to withstand. The ability to bend but not break. “The wind does not break the tree that bends” — Tanzanian proverb. This quote speaks to the flexibility necessary to be that type of person.

Resilient people accept the ebb and flow, the ups and downs of life. That life includes success and failure, birth and death (literally and figuratively) and even though in accepting that inevitability you will be tested in all ways, it’s just part of this living thing. I define that also as having grace.

A resilient person does not have a “victim mentality’’. Sometimes we think life is happening to us, instead of just happening and that type of mentality nurtures a defeatist attitude. You must accept that the journey is absolutely unpredictable. All the time. Once you can get to that place of acceptance, then you learn very quickly how to find solutions while mastering yourself and your responses to challenges.

Even though resilience requires a level of flexibility and acceptance it also requires preparedness as well. You must be willing to learn from your experiences. It’s one thing to be able to withstand challenges but you also must be able to really assess the challenge and what it took to overcome it and build upon that. That level of discernment is necessary to be able to withstand the next challenge.

When you think of resilience, which person comes to mind? Can you explain why you chose that person?

There are many people I admire who exhibit resilience but Boxer Mike Tyson comes to mind. Tyson has experienced a lot of the highs and lows of life publicly- great wealth, infamy, deaths, divorce, financial loss, celebrity, prison. He seems to have met all of his nine lives, evolving in unexpected ways but most of all, he appears self reflective and brutally honest and accepting about his past and his present.

Has there ever been a time that someone told you something was impossible, but you did it anyway? Can you share the story with us?

Oh, that has happened many times in my life. I remember I started as an intern at NYC radio stations WBLS/WLIB and then began working in the research department. One day I walked past the studio where shows were being done live and there was a female board operator there who I told I was interested in learning how to run the board. She became my mentor. Anyways, soon after I was offered the opportunity to run one of the weekend night shows on WBLS. WBLS is a FM station that was very popular in NYC. To run that show with as little experience as I had? Big big deal. My mentor told me I wasn’t ready. I ignored her, did the show and subsequently worked and traveled abroad as a board operator, for both WBLS and WLIB for 5 years.

A more profound experience was being told I would never have a child. I was an older mother, with PCOS (polycystic ovary syndrome) which means that infertility rates in women like me are high. I was told by a doctor, without having run any tests on me, but only hearing my age and my pcos diagnosis that “the train has left the station” and I would probably need IVF. I became pregnant 3 times after that prognosis. As I was having my second miscarriage at the hospital, a doctor told me that I should give up because of my age and the pcos, literally as I was miscarrying. Shortly after, I became pregnant again, naturally, with my daughter, who is now 7.

Did you have a time in your life where you had one of your greatest setbacks, but you bounced back from it stronger than ever? Can you share that story with us?

Like many, I’ve had financial setbacks, been unemployed for long periods but I’ve been blessed that I’ve always found a way through, around and out of those situations, always with the support of wonderful family and friends.

Did you have any experiences growing up that have contributed to building your resiliency? Can you share a story?

My parents and I lived in a few different countries including in Europe, the Caribbean and the US, which influenced who I am in so many ways. Even though I was a child, I was acutely aware of the newness of places and having to learn new people and them learn me. When you’re a child, it’s very rare that you get to have an opinion about what the adults, your parents, are doing. Not only did we live in several countries but we also moved many times in some of the countries. I guess I was forced to become flexible. As I got older, I was allowed to be privy to the plans to move but by then my ability to absorb and attune myself to new environments, people, cultures etc. was much stronger.

Resilience is like a muscle that can be strengthened. In your opinion, what are 5 steps that someone can take to become more resilient? Please share a story or an example for each.

Being resilient takes a certain mindset. The mindset includes being willing to

  1. Be flexible– bend, don’t break. It begins with a deep belief that there is a way through, that there is a “light” at the end of the tunnel, that the outcome may not be as you imagined but could possibly be even better.
  2. Be accountable– you must be able to look at challenges clearly without blaming anyone or any other circumstance. How you resolve a challenge is on you. No one else.
  3. Be accepting- Facing the reality of a situation, no matter how scary, allows you to find solutions quicker.
  4. Develop your self awareness– have a clear sense of your own potential, your strengths, weaknesses as well as your ability to withstand and to achieve.
  5. Cultivate a support system– no matter how resilient you become, there will be moments of doubt or exhaustion. Your support system should be there to remind you of your attributes, provide guidance when needed and offer an ear when you need to vent or talk things through. Your support system should also encourage the best for you and of you.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Currently, we live under and depend on a monetary system that also needs additional systems to be created for us to adhere to the system for it to work. We believe that the paper in our hands has value and we work to get more paper, die if we don’t have enough paper, can’t get healthcare without it, become homeless without it. The value of the paper shifts daily and with no effort or input by the civilians living under this system.

I would love to begin a community where we barter everything. Money as we know it could still exist but if money isn’t available to exchange we could place value on another thing, service, skill that someone is willing to exchange. It’s almost too simplistic to imagine it could work:)

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them 🙂

Russell Brand! I think he’s eccentric and wildly thoughtful, I absolutely love that about him. Like Mike Tyson, he is expressive about his childhood experiences, his addictions and now he is sharing his self awareness about his spiritual evolving. When you watch his video podcasts, he speaks fast, like his words spill out of his mouth at the speed that his mind thinks it, deducing and extrapolating, from social issues to human behaviors. He invites learned guests and I enjoy watching his openness to taking in new information and questioning. He is a “power to the people” type of man and the rebel in me respects his way of living out loud and on his own terms.

How can our readers follow you on social media?

Website- www.JenniferHeslop.com

Linkedin-https://www.linkedin.com/in/jenniferheslopmia/

[email protected]_s_heslop

Amazon link to Damn It! I Don’t Want To Planner- https://www.amazon.com/Damn-Dont-Want-Bullsh-t-Organizational/dp/B08R15HGLR/ref=sr_1_1?dchild=1&keywords=Damn+It+%21I+don%27t+want+to%21&qid=1626874029&s=books&sr=1-1

Shortened link to Damn It! I Don’t Want To Planner- https://bit.ly/DamnItTheWorkbook

Facebook-https://www.facebook.com/JenniferSHeslop

This was very inspiring. Thank you so much for joining us!

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

Resilience Does Not Equal Great Leadership

by Maribel P. Aleman, Aleman & Associates
LeaderSHIFT-with-Jennifer-Watson-LivingFearlessly-ThriveGlobal
Community//

Leader”SHIFT”

by Lisa McDonald
Community//

Barmes Founder Paul Barmes: To develop resilience, recognize the issue, choose what you are going to do, and act upon it”

by Tyler Gallagher
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.