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Single Parenthood: Life Before Homeschooling. An Ambitious Single Mother’s Story

Updated: Jan 18, 2022

Life Before Homeschool and Full-Time Travel

"I went from serving cocktails in a casino to being served in cockpits."

How it Started

Prior to living in California where we launched our full-time travel lifestyle almost 5 years ago, I was a cocktail waitress, and I put myself through college while raising my son in St, Louis Missouri. It was hard, but it stretched me in a way that made me get used to operating through stressful situations and doing things alone. Eventually, I dropped out of college and ventured into entrepreneurship. In 2015, I moved to California to pursue a corporate job that allow me the flexibility to pick up my son from school every day, and I felt like I made it big! I went from working as a cocktail waitress at a casino to landing a job title such as an Account Executive. I had a car allowance, laptop, cell phone and I was able to work from home making appointments with small and big businesses to sell them media services.

The Adjustment Period

It took a while to get used to the high cost of living in California. The first couple of months, I lived with a roommate in California while my son stayed behind in our hometown (St. Louis) in the care of family. That was HARD for various reasons! I had never been so far from my child and I would take trips I couldn't afford to visit him, but I eventually brought him home two days before NYE that same year and it felt like another huge accomplishment. The transition was a dream come true for both of us, but adjusting came with a set of challenges.

While I away working in California, my son Carter, fell behind in St, Louis due to our family lacking basic resources and not being able to agree on whose turn it was to do X, Y, Z involving Carter. Therefore when my son was still in a brick-and-mortar school and was on the verge of failing the second grade in Missouri and California, I knew it wasn’t because his teachers weren't doing their job, because my son was not smart or because we didn't have enough support. Although it’s easy to pass the blame on teachers, institutions, lack of resources, or on kids with behavioral concerns, I could tell my son needed individual support based on my efforts and experience in his classroom.

Things got to the point where I took time off work to become more involved in my son’s education. I volunteered at his school during the day to help out in the classroom because I couldn't get my head wrapped around why he was having a hard time. He would excel when I was around and he was a very social kid that always looked forward to recess, after-school activities, and field trips. Occasionally he experienced bullying, but for the most part, kids loved him for being a nice socialite! He was the kid that everyone liked because he’d break up fights or defend other kids that were bullied. While trying to figure out why he wasn’t succeeding with reading, during this discovery period, I was feeling defeated and like my back was against the wall for other reasons.

An Emotional Suicide

"I wanted a break to mentally and financially be able to breathe!"

The cycle of waking up stressed and sleep-deprived was never-ending and it sucked to forcefully wake up with an alarm clock. I was tired of the same fire drill type of routine every day. I woke up tired, grumpy, and in a hurry to get my son and myself ready for the day. We’d rush out the door for me to take him to school and then I’d sit in rush hour traffic.

"All that rushing in the morning to sit in traffic!?"

I had a lifestyle that often left me drinking numerous Monster and Redbull Energy drinks daily. I was an Account Executive working in a career that I grew out of quickly and I was tired of telling friends and my son that I didn’t have enough time to do leisure activities. I was frustrated that I couldn't afford to volunteer more or travel to visit family across the country because I couldn’t get enough days off in a row.

My passion and gift with public speaking are what led me to build a speaking and life coaching business in California and it was something that kept my sanity even though I wasn’t making a lot of money yet.

When my passion started profiting, things got a little more tricky because I needed more helping hands. My family was distant whether they were 2 or 2,000 miles away so I had no help with child support, transportation for my son from after-school activities, or help with my son while I did coaching calls or went to speaking gigs. The result was that my son came with me to all my gigs and he had to sit beside me quietly while I did coaching calls. We were both doing the best that we could in school, work, and business, but my credit cards were often almost maxed out and the cycle of not being able to consistently afford a babysitter or tutoring for my son after school continued.

( Speaking Competitions In Alameda California - Carter goes to work with mommy)

(Home - My apartment’s home theatre at San Marco Villa’s)

Keeping Up With The Joneses Got Old!

I was tired of trying to keep up with a full lifestyle that did not serve my family entirely. I was trying to keep up with what looked like success on the outside while living with the reality that I was drowning financially and feeling like a failure on the inside despite all the fancy things my credit score enabled me to look like I could afford. Regardless of the praise from my peers for the fancy two-bedroom apartment with resort amenities on-site, my nice car, or my job title, I eventually felt like I was an imposter knowing that my son needed me and I was still working a corporate job that made me feel like I was never going to reach my highest potential. At the end of the day, I was grateful that I was in a better situation than cocktailing, but my monthly take-home pay in the bay was only enough to cover my bills and leave me with $300 left to save or spend on Misc household stuff. It was as if I was more determined to satisfy my ego and prove to others that I could afford things than do what I needed to do for my mental health and my family’s legacy.

Something HAD to change!

"I felt trapped."

Life felt like I was slowly dying inside daily and feeling unfulfilled with the way things were. I had to do something different quickly or surrender to drowning in more debt. While I was stressing and holding on to a fancy apartment and a BMW, I was feeling guilty because I knew my son needed me and that I was not in the career field that I needed to be in that could provide me with the lifestyle I needed. Everything is expensive in the San Francisco Bay area and I thought about living somewhere cheaper, but I didn’t feel comfortable having a child and living with a roommate or living somewhere unsafe to save $500 and downgrade to a one-bedroom.

Leaving My Job

"I feel like I’m living in a fancy box that I can’t even enjoy because I’m too busy trying to keep up with it."

I no longer wanted to ask for my boss’s permission to take personal time off to do things like pick my son up from school if he was sick, volunteer in the classroom, or travel. I didn’t want to fight with my alarm clock every morning or keep slamming energy drinks and coffee in order to stay awake. I was fed up with making the minimum payment on my credit card bills and paying a fortune in interest every month. I was also tired of other people’s opinions about how I should get a man, put my son on ADHD meds, or move back to St. Louis where we were even more miserable.

My coaching business started picking up more and I ended up leaving my job and working for Uber and Lyft during the day while I continued to build up my coaching business. I felt more in control of my schedule but I still did not make enough money for me to get out of debt. My expenses were high and my son was still on the verge of failing. All I wanted was to travel freely and show my son that there was more to life than being too busy to do the things we love and spend time with loved ones without worrying about what to do next.

I wrote a Facebook post.

"All I want to do is travel the world with my son and explore hidden gems with him someday."

Someone commented on the post and said, “What’s stopping you?”. The question really made me think! The answer was my belief system, the emotional value I placed on material things, and the fear of looking like a failure. I also didn’t want to apply for another job just to keep dulling myself down instead of reaching my full potential with public speaking and coaching. At the end of the day, whether people thought I was very successful or struggling…I owed 15k in consumer debt that no one else was responsible for but me. Therefore I had to come to the understanding that other people’s opinions of me don’t pay my bills.

A Recurring Thought

"If I didn’t have to pay rent, I can pay off my credit cards in 2-3 months."

Still feeling the pressures of my son’s academic experience being rocky, I felt like I was failing him and I began considering homeschooling. Prior to a google search to research homeschool, I felt stuck because I didn’t know any parents or friends that homeschooled. I had a talk with my son that night and asked him how he felt about it. I was pleased that he had a great attitude towards the idea of being homeschooled and traveling and it felt like I had the green light to unroll him out of his school. We ended up trying Connections Academy for our online school of choice.

Carter’s Last Day Of School

I reassured him that it didn’t mean he wouldn't be able to see his classmates again and that I’d get him a cell phone so that he could keep in touch via Facetime. We also agreed that we'd come back to his school and our old neighborhood for playdates. All of his friends were happy for him and wished they could be homeschooled as well.

(We had a popsicle after school party on Carter’s last day of school)

Our first day of homeschooling in 2017

It was only after I enrolled my son in an online school that I got to know and understand how my son learns and performs best. Once I found the alternative to traditional education, I gained time back. We were able to avoid the weekly morning fire drill, traffic, and the homework that we normally are given on top of daily classwork. We wore our Pj’s all day on the first day of school and this became a weekly trend.

(Our first homeschool field trip - Lake Tahoe)

When we started doing more outdoor activities during the week, I found out that Carter desired to be outdoors more than sitting inside all day. He loved our mini road trips and flourished better with hands-on experiences. These outdoor experiences led to us having a conversation about traveling full-time while he's homeschooled and he loved the idea.

A month later, I ended my apartment lease, got rid of everything, and purchased two one-way tickets for Thailand. Read more here

Fast forward To Van Life

We wanted a slower pace of travel, but didn't want to settle back down. I had the idea of buying an old school conversion van that I remembered seeing as a child and use it to help alleviate the rental car costs and give us a comfortable place to rest and camp in between our Airbnb reservations. 30 days into our travels, we realized how genius it was to have our camper van because it made travelling full time a lot more simple. Read more here

Not only did we not have to our suitcases back up again or be part time travel agents scowering the internet for cheap deals, Van life lead us to exploring the outdoors more and seeing the world on foot unlike when we would flight and uber hop weekly.

Over the years, I have been able to witness my son do well and grow inside of his online education and adventures around the world. I've been able to get to know my child in a way that was missing when we were stuck under a roof trying to keep up with what looked like success to most people. I have also been able to grow my business without the weight of expenses that come from being stationary. We found true limitless success and a way of learning and achieving that works for us. Overall, I see that society needs to normalize it being ok to homeschool in an unconventional way because everyone does not learn the same way and families have different financial situations.


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786 views2 comments


Loved reading this! I’m a single parent and currently work remote but would love to travel more with my girls and have been on the fence of getting an RV or purchasing a small/tiny home. Have also considered home schooling even though school hasn’t been an issue w the exception of attendance (during travel) . I think my biggest concern is traveling solo as a single parent. Once I get over that mentally I’m sure things will fall into place.


Terrific blog post! You’ve come so far! Very inspirational!! Best wishes!!

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