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My Journey from Corporate America to Entrepreneurship

“You spend your whole life stuck in the labyrinth, thinking about how you’ll escape it one day, and how awesome it will be, and imagining that future keeps you going, but you never do it. You just use the future to escape the present.”

— John Green

This is the story of my journey from Corporate America to entrepreneurship. A story that began long ago at the start of my career in 2014. I had just recently graduated from LSU in May 2014 with a bachelor’s degree in Marketing. I had always been passionate about all types of Marketing, so this was an easy choice for me.


Right out of the gates, I scored a job with a Fortune 250 Company. I was grateful to even have a job because I knew some of my other friends were not as lucky. The job market at that time was competitive and it was hard to find a job in the field you wanted to work. Some even were giving up and going back to school for graduate degrees, but not me.


I had scored an entrance into this Fortune 250 Company’s Marketing & Sales Program for Recent College Grads. It was a 3-year program where you got to learn everything from Sales to Event Marketing to Brand Marketing. My first role moved me to Pittsburgh, PA and was a Sales based job with light marketing. In this role, we were all in remote roles across the US, so the management side of things was pretty relaxed. From the perspective of first-time roles in the workplace, this job rocked! I had my territory to manage and challenges for sure, but I had a lot of freedom.


Within a year of grinding & working hard, I was promoted into the next role of the Program, Regional Market Manager. While this role was still mostly sales based, you got to experience more from the marketing and management side of things. This was super exciting to me. I had grown restless in my previous role and honestly felt I had learned as much as I could in that position.


In this new role, I managed a team of 4 people ranging in age from 21-65 years old. What a crash course I got in managing - it was terrifying! I still lived in Pittsburgh, as this was still a remote role, but I traveled constantly. My territory was spread out over 5 states and I had to visit my team members on a monthly basis. I was on the road a lot. I pretty much winged it for the first few months which was the way of the land as I knew it. As neglected as I felt during that time, it taught me a lot of valuable lessons. In my time as a manager, I learned so much from my team of 4. Through the good times and the bad times, I grew more in my career and as a person.


About a year after starting my management role, I started to wonder when I would actually start to work on a Corporate Marketing team. I was restless and ready to start putting my degree to good use in my career. Soon after, I completed the program early and was promoted to the Brand Marketing Team at Corporate. I had climbed the ladder and was ready to make it big!


Or, so I thought.


What a RUDE awakening Corporate America can be. Up until this point, I really had been my own boss. I was working out of my house and no day had been alike at this point. Cue two years later, when I’m sitting in my cubicle in an actual office headquarters. It was overwhelming, but still definitely exciting. I stayed in this role on the brand team for a little over two years.


Over my tenure at this company, many questionable situations arose, but I continued to persevere, because I had been brainwashed to believe that I had no other choice. I was also being told that my time was coming. I was promised a promotion, a raise, you name it, I was promised it. All this continued to do, was keep me at bay, for the time being.


Turns out, this was never coming. A common tactic I had learned was widely circulating around the workplace. The good ole “keep telling you what you want to hear, until you figure out… OH, right, nothing’s coming.”


Over the years, I had trained my brain to just keep sweeping things under the rug, because I needed this job. I truly believed that I wasn’t valuable to other companies and that to make it in my career, I had to be loyal to this job regardless of the way I was being treated.


The one thing I wish someone would have told me years earlier before I had to endure the continuous beat downs on my confidence, is this:


It is okay to leave.

The many promises and the love of my coworkers are why it took me so long to realize that one key statement. Unfortunately, all of my coworkers were in the same boat. We continued to allow this abuse to take place, because we genuinely believed that there was nothing better and most of us were expecting promised promotions.


After other questionable situations arose, I finally felt strong enough to leave my company home of 4+ years. I journeyed on to work for two more corporations where I gained even more marketing tools for my toolbox. One was heavy in digital marketing and publishing, while the other was highly consumer product marketing based. In each of these companies, I also saw questionable situations arise and saw the negative effects office politics had on my coworkers. While I enjoyed the professional experience I gained, it didn’t take long before I started to feel like maybe corporations were not for me.


I am a strong, independent, and genuine woman who speaks her mind. Respectfully, of course. However, this quality is not always fostered and encouraged in the workplace. I often felt as if I couldn’t speak freely and that is something I was on a mission to never feel again.


So, let’s circle back to that quote from the beginning of this blog:


“You spend your whole life stuck in the labyrinth, thinking about how you’ll escape it one day, and how awesome it will be, and imagining that future keeps you going, but you never do it. You just use the future to escape the present.” — John Green

“You spend your whole life stuck in the labyrinth, thinking about how you’ll escape it one day, and how awesome it will be, and imagining that future keeps you going, but you never do it. You just use the future to escape the present.” — John Green


I was stuck in what I thought my future HAD to be. I kept hoping that the next role or the next company would ultimately make me happy. I thought working myself to death would lead me to happiness and fulfillment. I kept using that future promotion and future raise as my motivator. Always hoping that one day I’d be happier. I was using the FUTURE to escape my present, my every day. I knew this wasn’t sustainable and I was miserable. My confidence had been shredded and that is why I began Cali Creates LLC and this website JessieCali.com.


I needed an outlet and I needed a BIG change in my life. So, after many great career experiences, I took a risk and chose to leave the Corporate America world. I had an entrepreneurial dream and a fierce passion to work independently and for myself.


JessieCali.com is the hub of my personal brand and portfolio. I’ve worked for 8+ years gaining invaluable experience in all facets of marketing. At my core, I truly love helping businesses make their Marketing dreams come true. It's a passion of mine. Now, as a full-time Marketing Consultant, I get to work on a variety of clients marketing projects with the freedom to create my own schedule. It really is the best of both worlds. If you need some Marketing help, schedule some time with me here.


This newfound freedom also gave me the time to build my other passion project: Cali Creates LLC.


It took me many moons to find what I consider my life calling to be. I found that I am most happy and fulfilled when I am helping others in their pursuits to happiness. My ultimate goal in life is to share my stories in an effort to help people and spread love. That is precisely why I launched my company, Cali Creates LLC.


Cali Creates LLC began as a blog in 2019 where I shared my stories in an effort to help others and to create a safe space for those also on their self improvement journeys. Since then, I expanded the original blog into a Life Coaching & Healthy Living organization. The expansion included the addition of the Cali Chats Healthy Living Podcast, Vlog, and more blog topics all with self improvement in mind. If any of this interests you, you can subscribe here to join me on the path to finding true happiness within your mind, body, and soul.


All that to be said, my company and my personal brand would not be possible without the experiences I gained while working in Corporate America. As a former full-time corporate employee and now as a full-time Marketing Consultant, I’d like to share some pieces of advice I wish had been shared with me when early on my career journey:


  • Do NOT make work your whole life.

    • You need to have a work-life balance so that you can avoid burnout and maintain a healthy lifestyle. Only you can decide what that looks like and it’s up to you to maintain boundaries within that work-life balance.

  • Find what you are passionate about and RUN towards it.

    • Work can be rewarding when you find something you are passionate about. Work can also be the medium that helps support your passion. So whether it is your passion or is the means of how you support your passion, run towards it with everything you have.

  • Be YOU always.

    • Do not ever change who you are for a job. Trust me, it’s not worth it and you will find somewhere that accepts you for you. So, when something feels a little off and uncomfortable, say goodbye and keep looking. Your worth matters.

  • Always challenge yourself to be better and know your worth.

    • Choose yourself everyday. Take risks and challenge yourself to be better. Take small steps to make big changes. Choose YOU.


Take it from me, don’t stay in a job that shatters your self confidence. It’s not worth it.


My journey and passion led me down the path to entrepreneurship. Your journey may take you somewhere completely different, but wherever it leads you, make sure to lead with passion.


If you feel compelled to reach out, I would love to hear from you and you can connect with me through the contact form at the bottom of the JessieCali.com home page.


Are you a business seeking Marketing help? Head on over to my Marketing Consulting page and schedule a meeting with me.


Lastly, are you looking to overall just feel happier? Hit this link to check out Cali Creates LLC to start your self improvement journey.


So that’s my story. I hope you enjoyed it and I also hope you learned something.


Thanks for reading!


Talk soon,







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Jessie Headshot 3.jpeg

Hi! My name is Jessie Cali.

Whether you're looking for Marketing help, reading through a blog, or generally just curious, I am so glad to have you here. I am a self-employed Marketing consultant and a healthy living advocate. Read more about my journey here.

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