• Leily L Sanchez

Q & A Series: Shirell Gross, Esq.

The idea of changing careers after dedicating time to maturing one can be a daunting challenge, the prospect of which can be met with a lot of fear and uncertainty. But Shirell Gross, Esq. was able to overcome the fear of the unknown and thrive.



My first Q & A series guest is Shirell Gross, Esq. For this series opener, Shirell and I spoke about her career change process, her journey towards actualization, career advice for recent graduates and university students, her thoughts on the challenges facing career-oriented women, her inspirations, her upcoming book and the writing process, and her book recommendations and current reading.


About Shirell Gross, Esq.


Shirell Gross, Esq. is the founder and President of Measure of Ambition LLC. known as Shirell Speaks, a multi-service firm designed to challenge and empower through inspirational speaking, workshops, and coaching. The firm’s mission is to support, guide and encourage their clients to understand they have what it takes to reach their personal and professional goals. They work with corporations, organizations, associations, and individuals who are ready for an investment in a successful and fulfilling future.

After achieving significant success in her career in corporate law, she has embarked on a new chapter in her life: to pursue her passion for helping organizations and individuals as an inspirational speaker, life and professional coach through her company.



Shirell on Pursuing Law

On her website, Shirell Speaks, she writes that her ambition led her to be a first-generation college graduate and to eventually earn her Juris Doctorate from Hofstra University.

During our interview, she adds that she did not grow up knowing any lawyers and asserts that that should not discourage anyone else from considering a career in law. Opportunity can be found through LinkedIn and even by talking to people in the grocery store who might ultimately connect you with a lawyer that they know.

For recent graduates and those that have already started a career path, she offers this advice:

“If you want to be a lawyer regardless of where you are if you are in high school or college or even graduated from college, you should just do that. You don’t get an added benefit for having thought about it as a 9-year-old versus thinking about it as a 29-year-old. You just put your focus on that, and you get it done.”

Her final advice to students that are starting to explore pursuing law is to discover all the different areas in law and to be open to new experiences. She encourages students to learn about the different avenues available in law from different lawyers through networking.

Shirell on Career Changes and Pursuing Careers Different that your Degree

"I want people to understand that they can do more than one thing in their life. If they decide to pivot because they graduated and they went into another field, that is ok! It's not going to be the end of the world and it is far better to pivot than stay and do one thing just because people tell you that you're not able to do multiple things in life."

She goes on to say that part of the process in developing your career is to identify and write down what you like and what gets you excited. But equally important is to understand your dislikes and your strengths and weaknesses.

Shirell on the Process of Changing her Career


"It took a while, you know, it wasn't like I woke up the next day and said 'Oh! This is how I want to pivot my desire to help people.' ...You sometimes don't pivot because you are comfortable doing what you're doing, and you are fine, and you don't want to try anything new. All the fear and self-doubt kicks in so, it becomes a process."

The day that Shirell came to the realization it was time to pivot her passion for helping people into her new career was the day that she was invited to be a keynote speaker at a university event for graduate students.


"They were looking at me with this total glistening in their eyes because, in their mind, they were looking at and listening to this vice president in charge of the law department at this very large corporation. And I saw that excitement in their eyes, and I realized that I don't really have that same excitement anymore...and I wanted to experience what they were experiencing."

Shirell realized at that moment that she had allowed herself to stay in an environment where she was no longer growing and learning and limiting her view of what she could do and was capable of doing.

After this realization, it was time to find the core of her ambition and her reason for pursuing a career in law:

"The thing that I absolutely love and that is consistent with what I am doing now and what I did before is that I like helping people and that I like helping people get to where they want to be."

She clarifies that she really enjoyed practicing law but that she had simply reached a point where there was no more room to develop and grow in her career. She encourages college students, recent graduates, and working professionals to tap in with themselves frequently to identify the core of what they do so that if the desire to pivot does arise, you will be prepared to make the change.

Shirell on Innovative Thinking While Following an Organization's Lead


"The best way you can really make an impact is to focus on where you really want to make an impact. [Identify] what it is that you can really bring value impact to and learn about that...make it really specific."

She encourages working professionals, especially those early in their careers, to take advantage of the early stages of getting acquainted with a new organization. She asserts that the perfect time to identify if an organization is doing something dated is when you have an introduction to all the processes of the organization. Your advantage? You are coming into the organization with a fresh perspective, and you are not tied down to the day-to-day activities like other members of the company.


She adds that one thing to look out for when presenting a new idea is to work on the presentation. Sometimes, it is the way an idea is presented that kills the idea and not necessarily its content.


Her advice is to start by acknowledging how far this process has carried the organization and by declaring that you are proposing a change because you want to help people and to improve the organization. Remember that you are a problem-solver, not a critic.


"But then there are times when people are not open, and you just keep trying to be a problem-solver. ...At some point, you just have to say, 'who else can I speak to now within the organization?' Because you also can't fight for your growth. There are people who I know who graduated college, and they're in places where they can't do anything, and they wait, and they wait, and in a year or two, it's time to go! Don't feel bad!"

When contemplating moving on to another organization, Shirell says that the important thing to remember is that you tried and are now moving on to an organization where you can grow and be a problem-solver. You are free to choose an organization where you can be an innovative thinker.

Shirell on the Challenges Facing Women and Women of Color in Their Careers


During the interview, I pointed out that the challenge of implementing innovative thinking in a new workplace, along with an internalized paradigm of how women are supposed to be in the workforce, can hinder how women make career moves. We may also act in ways that don't align with how we truly want to act to advance our careers. So, to my female audience, Shirell says:


"The reality is that all women will continue to face challenges and women of color will continue to face even more challenges because the institution itself is designed for the institution to survive and in that [institution] you have individuals that play their part, and in order to effectively create change, you have to literally do things different than the way you do them. ...Many [organizations] are just not willing to do that. It takes bold moves in order to fundamentally change the culture of an organization."

However, despite this, Shirell offers a way that women can make the most out of environments where their contributions are not acknowledged or where they are not free to openly come as they are:


"What women and women of color need to always be focused on is to understand 'what specifically do you want to get out of this job?'...You have to develop relationships all across the organization because you need your name to come up often and with a lot of different people."

She encourages all women, especially individuals early in their career, to reach out to members of the organization to learn about them and their career path. And in terms of your career and skill development? Shirell says:


"You have to take on risky projects because people have to see that you can deliver on a project and deliver well. And often, you are not asked for those risky projects; we're just not. And that is why it is important to talk to a lot of people so that you can know what is coming down the pipeline."

She goes on to say that women need to ask for these opportunities and that there is no time to worry about how we are seen when we ask for these opportunities. She encourages everyone to interact in ways that allow us to perform and deliver in our careers with an ambitious and driven approach.

"There will be negative characteristics that will not always be spoken, that will be attributed to your behavior, and you just have to be crystal clear about what your behavior is and why you are engaging in a certain behavior. Because that behavior is a consistent trait that the organization needs in order to be successful."

She then shared an anecdote from her professional career when she was being assertive and forceful in order to advocate for a client. She was subsequently described as aggressive.

"There are times when people say things, and I would just ignore it because it is not worth it, but you don't ignore comments continuously because it's not going to help people figure out how to work with you. Because you teach people how to treat you."

Shirell points out, however, that if the judgments are about questions whether you have the right skills to complete a riskier project, ask yourself if those judgments are true. If those judgments are true, then get the skill! But, if the judgment is not true, which very rarely occurs:


"You just have to make sure that you have the right mentors, sponsors, people that you can ask for advice."

Shirell on Building Networks


She notes that young people build relationships in college and then don't continue to nurture them as they transition and settle into their careers.

"They start to socially live, and then you don't really hear from them until they start looking for a job because they are frustrated where they are...that is not how you do it. You have to maintain relationships for the long-term because you need people to bounce things off from."

She goes on to say that nurturing and caring for your network starts with checking-in and making sure that you are actively engaged in their careers as they were when you first reached out for help or advice. It can't be a one-way street.



Shirell Credits her Success to Two Dynamic Forces in her Life


In her journey to leading the law department in a large corporation and in her transition into a new phase in her career development, Shirell credits two forces in her life:


"I thank God, I really do. ...My mother was a 14-year old single mother who was assertive, ambitious. She was entering the 9th grade when she gave birth to me...and graduated on time. She knew, when I was in high school, that [...] she wanted me to go to college. Those two dynamic forces in my life made me literally who I am and who I have been throughout my career."

She credits these two forces for helping her be courageous in the face of fear so that she can develop and become the person she is today. She notes that when you are growing and developing your career, it has to be a scary process. The next steps should always be difficult. But finding that strength to challenge negative thoughts and apprehension will be your number one tool for your career development.


"You gotta have something that is your anchor. Something, your belief, your faith, your family. Something that is your anchor."

Shirell Speaks on Her Book and the Writing Process


Her book is scheduled for release in the first quarter of 2021. Her book will chronicle her experiences as she earned her degrees, started her career in law., and progressed to her senior position as a VP in corporate America. But her book will also address her journey to pivot her career to form her firm, Measure of Ambition LLC known as Shirell Speaks.


"The book really is going to be focused on how do we reset our own lives and move on from the fear of disappointment, fear of failures, fear of the unknown. ...The book will discuss specific strategies that I have done in my life to get me to be able to persevere and move forward."

Her motivation for writing the book is grounded in her observation in society:

"I find that we have a lot of information, but we have less action, and that is the problem."

She draws inspiration from Maslow's Hierarchy of Needs and the Theory of Self-Actualization, which is an intrinsic human desire to become everything that one is capable of becoming.

"A lot of the strategies [in the book], they're things that I use. ...As I was talking to the publisher, he asked, "What do you do? That's what people want to know."

Her book offers concrete strategies on how to manage your thoughts and your emotions based on her experiences and concepts that have proven to be effective.

Shirell Speaks on Social Comparison and Social Media


One of the critical components of her book is to create mindfulness about the behaviors in which we engage.

"It's not social media; social media is an avenue. ...We're seeing the good of social media with this pandemic. Social media hasn't done it; it's our use of social media. For the millennial generation, it's social comparison. ...Basing happiness and beliefs on something that isn't real."

To learn more about her strategies for overcoming social comparison in the age of social media, make sure to keep a lookout for her book!


And before the interview was over, I couldn't resist asking her what was on her nightstand and her book recommendations.

Shirell's Reading List


  1. Outliers by Malcolm Gladwell

  2. Crushing by T.D. Jakes

  3. Higher is Waiting by Tyler Perry

  4. Battlefield of the Mind by Joyce Meyer

  5. Emotional Intelligence 2.0 by Jean Greaves and Travis Bradberry

On Shirell's Nightstand:


  1. The Time is Now by Joan Chittister

  2. Range by David Epstein

  3. John Woman by Walter Mosley


For more information or to schedule an appointment with Shirell about her coaching services, visit her site Shirell Speaks. You can also follow her on her Instagram at Shirell Speaks or keep in touch on the Shirell Speaks Facebook page or follow or connect on her LinkedIn, make sure to reference this blog post to connect!