I Don’t Want To: Interview with Leadership Coach Jennifer Heslop

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Jennifer Heslop
The "I Don’t Want To" planner was designed by a leadership coach named Jennifer Heslop



“Damn It! I Don’t Want To! The No Bullsh-t Organizational Planner You Need” is a new organizational planner by Jennifer Heslop that was designed after a quarantine spent journaling. Jennifer hails from New York but currently lives in Florida. Her thirty-day motivational, inspirational, planner encourages readers to take a good hard look at themselves so no one avoids doing what they need to. The planner includes motivational quotes from members of the arts, entertainment, sports and business industries, which aim to increase self-reflection and self-actualization.

Jennifer is the founder of JSH Coaching, a company offering both individual and group leadership coaching, life coaching and business consulting. She believes that intermittent personal and business inventory is the foundation for growth, innovation and success; she has also developed powerful tools to reveal areas that hinder or support the advancement of a leader and the leader’s business. The planner is available for purchase on Amazon.com.

Jennifer recently discussed the planner via an exclusive interview.

Meagan Meehan (MM): When did you first realize that you wanted to be a life coach and how would you describe your style of advice?

Jennifer Heslop (JH): I’ve always given advice. Even at a young age, other kids, older kids would ask advice. As an early teen, I became aware of my ability to make people speak with me openly when I met a boxer in Trinidad and I asked him questions about his career.  I remember that he seemed to really enjoy the exchange. At that time, I thought that journalism would be my career choice. My professional career began in media, arts and entertainment and then I became a career advisor at a trade school in NYC.  My job entailed resume and portfolio critiquing and finding employment for the students, but it was during the one-on-one moments with the students, where I made the most impact. Those moments, where the students were vulnerable and really needed guidance, not only for their career but often about their personal lives, mental and emotional health, in those moments I got to really help. That’s when I started claiming the title “Coach”. My style of advice is holistic.  As a Leadership Life Coach, I don’t believe who we are in our personal lives can always be separated from our professional lives. We bring ALL of ourselves to every situation, so while coaching I may take into account many factors including how your day is going, the health of your significant relationships, your mental programming around accomplishment and success, your history of following through and even your physical well-being.  The whole of you matters.

MM: What gave you the idea to create a planner?

JH: Well… I’m human, so even though I’m a coach, I’m constantly self-assessing and one day I just really had to pay attention to the fact that I was comfortable ignoring my bills. I mean, piles of bills. I would just ignore them.  At that time in my life, I was a freelancer, not working consistently and when money came in, I had to prioritize so I would just ignore the bills.  One day it just occurred to me that it wasn’t about the bills, I looked at my behavior and then started looking at where else in my life I was avoiding taking action. The “Damn It! I Don’t Want To!” planner is a tool of accountability. It will require you to look at your 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.

Jennifer HeslopMM: How did you find all the fun quotes?

JH: I am personally motivated by athletes, watching documentaries about them, and reading articles about them. I’m so curious about their process, their focus and their insatiable drive. So, when I began writing the planner, I sought motivational and inspirational quotes from business leaders, athletes, artists, philosophers, thought leaders.

MM: What is your favorite part of the planner?

JH: The quotes…the quotes still motivate and inspire me to action.

MM: What inspired the aesthetics of the planner?

JH: I wanted the planner to look and feel like a book. A book you would want to read and write notes in, take on vacation with you, on long trips. A book you would keep coming back to once completed, to see how much you’ve accomplished.

MM: How did Covid impact your career?

JH: Four years ago, I moved from my hometown NYC to Miami and had to re-establish myself and my business. I had just made traction and then Covid hit and suddenly networking, business, everything stopped. Recognizing that the entire planet has been experiencing the same thing at the same time means that we are not as separated as it would seem. 2020 proved our basic similarities globally. Subsequently, I have widened my network, offering my services to people, not just in my state or country but worldwide.  Utilizing video platforms like Zoom, is also an amazing asset and advantage.

MM: What steps do you think everyone can take to make their lives happier and more time-functional?

JH: I’m big on assessments and evaluations, in both personal life and professional life. The road to happiness begins with self-accountability. Often, we predicate our happiness on our relationships, our environment, or social context but once you look at and recognize who you really are, inside and out, strengths, weaknesses, positive and negative aspects, then you become in charge of your own happiness. Being more time functional can be accomplished first by planning. Being the architect of your own happiness via self-accountability means taking charge of your life- getting clear about what you want, making a decision to get what you want and planning how to make it happen. To execute a plan requires being organized and committed.  My most basic but essential tool to remaining organized and time functional is my Google Calendar! I put everything in my daily and monthly calendar including appointments, meetings, lunch breaks, gym time, when I have to drop off and pick up my kid from school, when to post to social media, date night… I mean EVERYTHING. It helps me look at my life and my time in a holistic way.

Jennifer HeslopMM: What has been the best thing about working in the mental wellness industry so far?

JH: It’s a gift to be able to guide and support my clients to their highest potential so there is nothing like witnessing them get out of their own way to experience growth and ultimately success.

MM: What projects are coming up for you soon and is there anything else that you would like to discuss?

JH: Along with offering individual and group coaching packages and the “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 15.  I love leading the workshop because I guide and offer support through dialogue and because the group is small, each participant can learn from, feel affirmed and motivated by the others.

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To buy the planner, see here. To learn more about Jennifer, visit her official website.