My Journey from Employee to Entrepreneur

My Journey from Employee to Entrepreneur: The Long and Winding Road

Sometimes, people find their path in life early on. The dreams they held as a child come to fruition in young adulthood. This wasn’t the case for me and I struggled well into my late twenties. I want to share my journey from employee to entrepreneur with you in hopes that you can learn from what I experienced and have a more direct path to the life and lifestyle you want and deserve.

My journey from employee to entrepreneur was a long and winding road. My parents divorced when I was three years old, so it was just my mother and I while I was growing up. I learned at an early age that we would never have enough money to cover our expenses. My mother was ill on a regular basis and during those times I took over with the cooking, grocery shopping, cleaning and getting myself off to school each day.

I used to ask her for money and she would always give me a nickel or a dime. I would hide these coins in the bottom of a drawer and then use them when we didn’t have money left for food. In the late sixties and early seventies, two or three dollars bought the two of us enough food for a week.

By the age of ten or eleven, I had learned to offer my services to the neighbors for all kinds of odd jobs. These included doing their laundry, babysitting, and going to the grocery store to do their shopping. I could earn a few dollars every week this way and the money made a huge difference for us.

The summer when I turned twelve, a series of circumstances took us from southern California to Miami, Florida. My mother got a job as a caretaker for a large house that was going to be sold eventually to make room to build five smaller homes. This property was huge and I planted a vegetable garden right away.

As I was busy with my vegetables, I met the family next door. There was a boy my age, Junior, two younger brothers, Larry and Tory, and a little sister not yet old enough for school named Daphne.

It was Tory and I who became fast friends. He didn’t get an allowance either, so we began doing all kinds of things to earn money. We mowed lawns, cleaned out garages, collected empty bottles to return to the store for the nickel deposit, and raised hamsters to sell to the local pet store. It was fun to earn money in this way, but soon I longed to have a real job.

That opportunity presented itself when the Tucker family moved in across the street. Mr. Tucker was going to be the manager of the new Uncle John’s Pancake House just a few blocks away. I introduced myself to him and his family and asked him for a job.

He asked me how old I was and I told him I had just turned fourteen that summer. He said I could work as a hostess on Saturdays and Sundays for a total of eight hours each week. The pay was $1.25 an hour and I started right away.

I can remember when he handed me my first paycheck a couple of weeks later. Although I had grossed ten dollars, my check was for $8.33 after taxes were taken out. One of the waitresses explained it to me so I would understand how it worked.

One Sunday afternoon, a waitress named Doris asked me to take an order from a couple who had been waiting because we were so busy.

“I don’t know how to do that,” I told her. I was used to seating people, bringing them water, asking if they wanted coffee, tea, or something else to drink, and that was all. Sometimes I also helped the busboy clean the table after they left.

She tore off a ticket from her book and handed it to me, along with a pen.
“You ask them what they want, write it down, stick the check on an empty hook in the kitchen window, and stand there until the cook gives you their food. Can you do that?”

I nodded that I could and took their order. Then I delivered it to their table as carefully as possible. I made sure to take good care of them while they ate, asking if they wanted more coffee or anything else and removing their plates when they were done.

When the couple finished eating and got up to pay, I thanked them for eating at our restaurant and they smiled at me. I began cleaning the table and picked up the two quarters they had left as a tip. I took it over to Doris and handed it to her.

“What’s this, the tip?” I nodded.” That’s your money, Connie. Put it in your pocket and get back to work.”
I did as she told me, and in that moment I had a new goal: I now wanted to be a waitress instead of a hostess.

That week at school seemed to take forever to come to an end. On Friday evening, I walked across the street and knocked on the door where the Tuckers lived.

Mrs. Tucker answered and I could see their little ones stretched out on the floor watching television in the living room. The Flintstones were on and I had forgotten that I liked to watch that show. She motioned to her husband and Mr. Tucker came to the door.

“Hi, Mr. Tucker. I wanted to tell you I don’t want to be a hostess anymore.”
“I’m sorry to hear that, Connie. You’re a good worker and I’m sorry to lose you.”
“Oh, I’m not quitting. I want to be a waitress now. Doris had me take an order when she was busy and she told me I did a very good job.”
“Connie, you’re not old enough. And you don’t have the experience it takes when we get busy. Maybe in a year or so we can discuss this again.”

Not one to take no for an answer, I stood up as tall as I could and pleaded my case.

“Mr. Tucker, please give me a chance. Just give me three tables in the back. That’s half a regular waitress station. And just give me a few hours to show you what I can do. Please, please let me try. If I don’t do well, I promise I will be a hostess again and never ask you for another favor for the rest of my life.”

He glanced back at his wife and she was smiling and nodding. Then, looking down at my shoes I added…
“My mother and I need the money for groceries.”

“You drive a hard bargain, but I’ll take a chance on you. Come in a little early so we can fit you with a uniform.”

“Thank you!” I said, and walked confidently back home.

I didn’t tell my mother, because I thought it would be better if I told her after I did a good job and knew I could continue in my new position.

My next check was also for $8.33, but it didn’t matter. I had earned almost six dollars in tips and back then – this was 1970 – they were not taxed so it was pure profit.

For my mother’s birthday the following week, I bought her a purse and a pair of shoes that had been on sale at the shopping center, and then sat down and told her the story. She was proud of me and I knew that as long as I had a job we would never again go without food, clothing, or enough money to pay the rent.

My mother had always instilled in me the importance of getting an education so you could get a good job. Now that I had joined the work force, I was even more excited to follow this path.

There were more jobs over the years, mostly in restaurants but also odd jobs. One summer I scraped barnacles off of wooden boats for five dollars an hour. Once I turned eighteen, I worked as the manager of a coin laundry and got to do my laundry for free.

During my first year of college, I took a part-time job at a veterinary clinic. I loved animals and had always wanted to become a veterinarian. Two vets ran this clinic and I had ample opportunities to see what this work would be like. In less than a year, I determined that I could not bear the pain and suffering of the animals that were brought in and that I would be better off working in another area and having pets of my own instead was best.

By the time I graduated from college, I had decided that a career as an attorney would be right for me. I took a year off to work at the phone company and save some money. Then I applied for the following year and was accepted at a law school in New York City.

I was now married with two young stepchildren who lived with us part of the time and with their grandparents the rest of the time. My husband was a general contractor and took a job in the Middle East building part of the new airport in Teheran. The kids were excited to start the school year in Georgia with their grandparents. Off I went to New York to finally learn what was needed to become a lawyer. I was interested in real estate and decided to pursue that part of the law.

It was the returning students who were now working attorneys that convinced me this was not going to be the career I had thought it could be. They were guest speakers once a week and we could ask them questions. One man had now been a lawyer for ten years and still hadn’t been assigned to a case in a courtroom. He shared that he felt like a glorified law clerk with no future ahead.

Life intervened and I did not finish law school. My husband died after a 14-month battle with Leukemia, my step-kids were with me for a year and then decided to finish high school in Georgia with their grandparents. I moved back to California and was once again looking for a direction that would make my life more complete and satisfying.

I took jobs at two different banks and was held up at gunpoint twice. Then I worked as a claims adjuster for Liberty Mutual Insurance. I was a field adjuster, meaning that I had a company car and an expense account, but I couldn’t visualize a future in this business.

By this point, I was more than disillusioned with being an employee who was dependent upon being in the work force for my income. Also, I had learned that getting and keeping a job also depended on the number of people employed versus those looking for work at any given time. And even though I had a college degree, many times I was not the most desirable employee for a company for a variety of reasons. I was definitely ready for a change.

I went back to college and took some classes in computer programming and learned Fortran and Pascal. Even though I’m an introvert, I saw this work as being too solitary for me. A few months later, got my real estate license and went to work as an independent contractor – one step up from being an employee – for a company called Day Realty. I had wanted to specialize in real estate while I was contemplating a future as a lawyer, so this move made sense for me at the time.

It was now 1986 and I was a year past my thirtieth birthday. I was making money in real estate but something was missing with how I was feeling about my life and future. I needed something that would make me feel like I was helping others and real estate just wasn’t it.

On a chilly day in January, I walked almost three miles to the office to get some exercise and to think about my future. By the time I’d arrived, I had come to the conclusion that it was a career that I was lacking.

While becoming a veterinarian or an attorney hadn’t been right for me, I believed and prayed that somewhere there was a career that had my name and personality written all over it.

I entered the office and realized that the other real estate agents were gathered in the back. The television was on and it was then I remembered that the Space Shuttle Challenger was launching that morning from the coast of Cape Canaveral in Florida.

This television was small, so I pulled up a chair and sat behind the others so I wouldn’t block their view. They showed the crowd watching with great excitement and the news commentator moved in closer to show us the family of Christa McAuliffe, including her husband, parents, and two young children. She had been selected from more than 11,000 applicants to the NASA Teacher in Space Project and was scheduled to become the first teacher to fly in space.

As the world watched, the Space Shuttle Challenger broke apart 73 seconds into its flight, killing all seven crew members aboard. The spacecraft disintegrated 46,000 feet (14 km) above the Atlantic Ocean and the crowd in attendance, along with me and the others watching in my office, went silent.

The cameras panned over the crowd once more, and I saw the looks of horror on the faces of Christa Mc Auliffe’s parents. Then they showed the auditorium of the school where she was a social studies teacher, Concord High School in Concord, New Hampshire. The entire school had gathered that morning to watch one of their own make history, but not in this way. At that moment, I felt a connection with those students that I couldn’t quite explain.

Someone got up and turned off the television. One by one, we each got up and went back to our desks. It was eerily quiet in the office. I sat there for the longest time, tears flowing and hands folded, praying for the families of those lost in this unimaginable tragedy. But almost immediately, my mind went back to those students. I had wanted to be a teacher while I was in elementary school and even into junior high. But I had never mentioned this to anyone, not even my mother.

Within a year, I had enrolled in college for the Teacher Credentialing program and was working fifteen hours a week as an assistant at the local elementary school

For the next twenty years, I worked as a classroom teacher. I had fully intended to give up real estate for good once I earned my teaching credential, along with supplemental credentials in science and technology, but the teacher’s union had us go out on strike during my first year. We walked in front of the school each morning with our picket signs and I was grateful to be able to go into the real estate office in the afternoons. It was an excellent reminder to me that jobs do not represent the security that most of us thought we had.

Teaching had finally brought me the joy and satisfaction I was looking for in my life. I loved my students and their families and became close to many of them. This was my calling and I thanked God each day for His tender mercies.

I had continued to work in real estate for all of these years, both as a broker and a residential appraiser. I did this after school, on weekends, and during the times when school was not in session. Also, I had now survived cancer multiple times, including Stage 3 breast cancer that was now in remission. I was exhausted but needed to keep moving so I would earn enough money for my expenses, along with supplementing my mother’s meager Social Security check each month.

Over the years, teaching changed in many ways, but I kept telling myself the challenges would work themselves out over time and continue to benefit the students. They did not.

During the last five years I was in the classroom, the focus became exclusively on the testing that was done each year throughout the United States. The schools I taught at were all designated as being Title I schools, meaning that these schools are those that receive additional federal funding from the U.S. Department of Education due to the high percentage of low-income families they serve. About 43% of public schools currently qualify for Title I funding, with a total of 49,229 schools benefiting from this program.

Slowly, our curriculum was modified to only include language arts and mathematics. The administrators took away the social studies, health, and science. Art and music programs were cancelled and physical education was shortened to 25 minutes each day, the minimum time required by law.

One day, the principal came into my classroom and told me to turn off the computers. I pointed to the State Education Standards I had posted next to them, showing the Standards covered by the lessons I was teaching on the computers. She removed what I had posted and we could see her tearing the papers up as she left the classroom and walked down the ramp.

After school, I stopped in to her office to speak with her. I sat down across from her and she waited for me to speak first.

“I thought it was a federal requirement that we have at least one computer in each classroom. Has that changed?”

“No, Mrs. Green, it has not changed. But it does not mean you need to turn them on. Am I making myself clear?”

I nodded and got up to leave. As I walked back to my classroom, I thought about what this change to my teaching would mean. My students were poor and I believed the computer lessons I taught them were for vocational training more than for any other reason. I wanted them to be competitive in the job market when they were older.

On that day, part of me died inside.

A week later, I was part of a three-day in-service at school, where substitutes were brought in to cover your class while you received training with some of the other teachers. On the first day, we were asked to get into small groups and discuss the students we were teaching and our goals for their education. One person from each group then shared their ideas with the others.

Yes, I volunteered to share, and I discussed my goals and dreams for my 5th grade students that year, including science, computers, and technology.

A man from the Los Angeles School District was overseeing our training that day, and after I was finished speaking he came closer to me and said,

“Who exactly do you think you’re teaching?”

“I’m teaching the future leaders of our country and beyond. These will be the people whose ideas and understanding will make a difference for generations to come. They must have the knowledge and skills to take their place as leaders in our world.”

“No, you’re not. You are teaching people who will be lucky to get a job at minimum wage. They will need to read and write at a level that will allow them to be employed and follow directions. They must be obedient and know their place. Your job is to ready them for the real world, not a fantasy world.”

On that day, an even bigger part of me died inside.

I knew then, in the fall of 2004 that I had to make a plan to leave teaching. I had no idea what I would do next, as now I was getting closer to my 50th birthday. But I prayed an answer would come for me and that it would make sense as it unfolded.

In the spring of 2005, I woke up very early one morning and felt like something had shifted inside of me. The sounds of the birds coming from outside my window sounded more distinct and when I looked out the window the colors appeared brighter to me. All of my senses were enhanced, or so it seemed. My orange juice tickled my tongue and my skin was softer to the touch.

I began writing in my journal and I could feel that an answer to my prayers was closer than ever before.
Then, I started attending evening and weekend seminars whenever I could and reading books about people who had changed their lives in meaningful ways and had gone on to success. I met a couple who had left the corporate world behind. The husband had got his real estate license and I agreed to be a mentor to him in that area. The wife had learned about Day Trading in the Stock Market and was doing well. I too wanted to take the journey from employee to entrepreneur.

One evening, I attended an evening seminar on making money from home. This one was different from any I had been attending, in that the focus was on earning income on the internet. One of the speakers shared how he was creating one-page websites on a topic of interest to many people, and selling a simple solution. He gave a few examples and even showed us one of his websites.

My takeaway that evening was that I could help people by selling information I already knew about, specifically in the areas of real estate and education, and more generally in the areas I was interested and knowledgeable in like gardening and pet care. I would be an online entrepreneur, as many thousands of people all over the world were already doing as a business from home, or from wherever in the world they happened to be, with only a computer and an internet connection.

I made my plan to resign from teaching at the end of the school year, on June 30th of 2006. That was eight months away and I got busy right away.

My entrepreneurial journey continues to be both joyous and prosperous and I now live what I refer to as a “lifestyle by design” where I choose the hours I work, the people I interact with, and the topics I share with others. Along the way, I have also written more than twenty-five full-length books and become a bestselling USA Today and Wall Street Journal author.

Anyone can achieve what I have done, and you can modify it to suit your personality and life choices as you make the journey from employee to entrepreneur. Entrepreneurship is wide open to all who pursue it. Thank you for reading what I’m sharing with you here, and please reach out to me if you have questions or comments about anything I’ve discussed.

I’m Wall Street Journal and USA Today bestselling author, independent publisher, and serial entrepreneur Connie Ragen Green and would love to connect with you. Perhaps you’d be interested in being mentored by me in a safe and collaborative small group environment with my Monthly Mentoring Program.