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The Courage to Become | Jessica Rockowitz Fielder

The Courage to Become | Jessica Rockowitz Fielder

My name is Jessica Rockowitz, and I’m a mom of three – Hayley (13), Colin (4), and Graham (2). When people first meet me, I usually have one or both of my boys in tow. They’ll often ask if I have other children –  I’ve admittedly grown fond of the looks on their faces depicting sheer shock and sometimes horror when I inform them that I also have a teenager.

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“But you look far too young to have a teenager!” they exclaim, taken aback. I smile and nod, now accustomed to this song and dance – and so my story begins.

My path to motherhood was one that I unexpectedly embarked upon at the ripe age of 17. It wasn’t supposed to be this way. As a straight A student with dreams of an Ivy League school and a career in medicine, I was supposed to spend my junior year of high school studying for the SATs and flipping through college guide books – not scrambling for extra money so I could scour eBay listings for gently used baby items because I could barely afford to put gas in my car.  

When I was about six months pregnant, my mom told me about a young parent program that her friend had heard about on the radio. The program was through a traditional four-year college that had about six spots for young, unmarried parents to live on campus with their children. The program also included room and board, a meal plan, and childcare for a very discounted rate. There was a catch, though – the program was located across the country from my mom and sister, who were a big part of my support system at the time. I was afraid that I’d be unable to raise my daughter without them, but I also knew this was our best shot at the life I envisioned for us. As silly as it sounds, I had dreams of a house with a playscape, Disney World vacations, and overnight camp. When Hayley was just shy of nine months old, I loaded her and our giant suitcase onto the plane to embark on what would be a truly life changing journey for us.

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I wish I could detail everything that happened during those years at college, but that would be a novel in and of itself. I graduated college with a 3.9 and a BS degree in Biotechnology, accepting a research position at Harvard University for that coming fall. My daughter was almost six at the time and truly thriving, and I was getting married that winter.

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I remember that the week I graduated college, I cut my Food Stamps card into tiny pieces, so proud that I would be able to stand on my own two feet. We signed the lease on a gorgeous apartment right outside of Boston in a safe, beautiful school district. We were financially and emotionally thriving – life was good, and we were happy.

Despite this, something gnawed at me and continuously stirred this feeling in my heart that I was unfulfilled. I beat myself up about this on a regular basis. What was wrong with me? Why wasn’t I satisfied with this beautiful life that I had worked so hard to create? I was always taught that the path to success looked something like this: attend the best college you can get into, land a great job, and work hard to climb up the career ladder. This was the linear path that I was on, so why was I so unhappy? I loved working with people and making a difference in their lives. In my current research position, this component of my passion was really lacking. On top of my work, I had been mentoring other teen parents and young moms for years, and it was a huge passion of mine. I told my husband that I wanted to go back to school to be an OB/GYN physician and work with young moms to educate and empower them. Life had other plans, though, and I decided to switch my career path from medicine to nursing in order to have a more flexible lifestyle because we wanted to grow our family.

Like always, I did my due diligence. I researched the best programs in the United States because just as my family had taught me, I wanted to strive for the best. I was accepted into and attended an Ivy League BSN/MSN Nursing Program. I was so proud of myself for getting in and worked hard to graduate and land what was my dream job at a low income OB/GYN clinic in downtown Philadelphia. I absolutely loved my patients. I was now a mom of two, and the working mom juggle was real. Still, I felt like I had reached an important milestone in my career and figured that the journey could only go up from here.

After a few months, that familiar feeling began to gnaw at me again as something stirred inside me and whispered, you’re not happy here. I found myself in tears on a daily basis and having a tough time getting out of bed each morning. I loved my job and my patients, but I couldn’t shake this perpetual feeling that something wasn’t right. What was wrong with me? I began to think that I was lazy and broken, and I just couldn’t figure out why I was feeling this pull to be away from what I had once again worked so hard to achieve.

While I was working in Philadelphia, I had also begun to dabble in the world of freelance writing. I signed up for a platform where I could find paying clients and began to take a deep dive into this space. I landed my first client for essentially pennies but was so thrilled that someone was paying me to write! I had always dreamt of being a writer and getting into marketing, but I was told that the world didn’t need more of us. It wasn’t lucrative or secure, and after all, I had a child to raise. Everyone persuaded me in the direction of stability, which equated to science and medicine. This was a huge reason why I had embarked on the path that I was on.

Now expecting our third (and last!) child together, my husband and I sat down one night when the kids were asleep. To this day, he still knows my heart more than anyone else in the world and is truly my best friend. He sensed that I felt the calling to not only be home for both of our kids, but to see where this career in writing could take me. I made the terrifying decision to leave the nursing profession that summer, when I was about 2 months pregnant with my now 2 year old. I never looked back, and so began my journey into the world of entrepreneurship.

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As an adult and business owner who is constantly evolving and fine tuning my craft, I didn’t know what it meant to be an entrepreneur. From a young age, I was taught to work hard, go to college, and get a good paying job. There was no other path to success in life. It was no surprise that I felt completely broken when I didn’t fit that mold. I’d land amazing job after amazing job, only to feel empty several months into it, all passion and spark completely gone. I began to feel ashamed, and it took a huge toll on my self worth.

Now that I’m an adult, I realize all my feelings and emotions were due to the fact that quite simply, I was never meant to work for someone else. Knowing what I know now, I truly think sometimes that we are born as entrepreneurs but depending on the environment we grow up in, we don’t ever get the opportunity to realize it. Did you know that many intelligent, hard working entrepreneurs make some of the worst employees? We are the ones who have trouble with things like following authority and staying on task. I spent so much of my adult life believing that something was wrong with me, when really, I just wasn’t on the right path for me.

The most ironic part of this is that I work harder now for myself and my clients than I have in my entire life. I work more hours per week than my husband, and I love every crazy minute of it. This is what I was meant to do, but nobody had ever opened my eyes to the fact that there is an alternative to the traditional mindset of college and the corporate world.

I had always dreamt of being a writer and working in advertising and marketing, but I didn’t know what that looked like. When I left nursing, it was almost like the finality of the decision weighed heavily on my shoulders. I had just worked so hard and had gone into deep student debt for a degree I didn’t love. What did that say about me as a person? Where would I go from here?

Many people ask me how I got started in marketing since I don’t have a background in it. I was a marketing minor in college, but everything I learned then is obsolete now because of the rise of social media and digital marketing. The foundation remains the same, but the logistics are so different. When I first began freelance writing, a small start-up reached out to me and asked me to run their social media. Their premise was a safe, COPPA compliant social network for children. They offered me the position because in their words, “I was a good writer and also a mom, so I knew their audience.” Thinking that it could be a great opportunity, I took it. This was the tiny stepping stone that I needed to open bigger and better doors for myself. I was in the right place at the right time, and though the start-up ultimately failed, I then moved on to bigger and better clients who taught me even more about the incredible world of content strategy and social media marketing.

Today, I have my own digital media agency and work with clients that I love and admire. I have also recently gotten into photography and launched my own photography business that I think really compliments my agency and has sparked this newfound passion that I never knew existed. I’m so excited to see where it takes me.

I dedicate at least one hour per day to education, where I listen to podcasts, read articles, and improve my overall knowledge so I can best serve my clients and continue to grow. I have huge plans for my future and where I envision myself. Sometimes I find myself daydreaming about it, and it takes me back to those days where I thought that the only correct path in life was to choose a career from a handbook and spend your life inside that box. There’s nothing wrong with this, of course. As one of my close friends once told me, she watched her father own his own business and never have any boundaries, so she knew she wanted a position that she could walk away from at 5PM. There is so much happiness on both sides – it’s just about finding which side speaks to you, your passions, and your priorities.  

Being a former teen parent, this transformation into who I am as a business owner and entrepreneur goes hand-in-hand with my transformation as a mother. I was so young when I had my daughter, and motherhood was not something I was welcomed into with open arms by those around me. In a way, I felt like I didn’t have permission to be happy and fulfilled in this role. I was supposed to struggle. It was supposed to be difficult. It wasn’t until I gave myself permission to be who I was – to leave a job that I had worked hard for, to have my second and third children – that I had the courage to really become the career woman and mom that I always felt I was meant to be, on my own terms.

I’m motivated each and every day by my family and by my desire to bring something unique and different to the world. I thrive on watching business owners reach their goals and fulfill their dreams. Being the one to help them get there is the most incredible and rewarding feeling that is almost indescribable. I no longer dread Mondays. In fact, I welcome them each week as I dive into my day’s work, able to drop it at a moment’s notice for a sick child or a school function. This is the life I dreamt of – and I’m living it.

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I can’t sit here and pretend that it’s perfect, of course. I always joke that I have the best and worst of both worlds. It’s very true that I don’t have any boundaries. I work in early morning hours, late night hours, and on weekends. I work at nap time, bed time, and am guilty of using PBS Kids for a last minute sitter. Still, though, I wouldn’t change a thing. I have built this incredible lifestyle for myself, and I am so excited to see what’s next.

Here’s one thing I want young women everywhere to know –

there is no distinct path to success and happiness. It’s ok to be unsure about your future and what fuels you, even as an adult. It’s ok to feel fulfilled being a stay-at-home-mom, or not feel fulfilled as a stay-at-home-mom and know that you’re a better mom for your family when you work.

The path to joy is not linear, and you are not the victim of your own life.

If you want something, go out there and get it. There is enough for everyone, and don’t let any woman or person tear you down or talk you out of your dreams. Big risks can mean big failures, yes, but also big rewards – and is it ever a failure if we’re learning from it?

Essay by: Jessica Rockowitz Fielder

You can get in touch with Jessica here:

Jessica Rockowitz Photography  Media Agency  Facebook  Instagram


 Jessica captured this moment for us, and I love it! 

Jessica captured this moment for us, and I love it! 


Review of the week for, The Courage to Become

"I was glued to your book! My kids said, "Gosh Mom, that book must be really good, you haven't put it down since you got it!" I loved your book, it made me realize, I wasn't alone in many of my thoughts. Please, please write more books, blogs. Believe me, you have a gift that can help so many of us. You talk about what so many of us are afraid to talk about, but you do - and you have the solutions. You are a gift to all of us." -Maritza

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