I never imagined that I would someday be homeschooling my children, but here I am. With the twists and turns my life and my family’s life has taken over the past few years, I now can’t imagine anything but homeschooling. In this article, I want to share with you the journey that led us here.

Putting the Cool In Homeschool

My first encounter with the philosophy of homeschooling occurred when I was in elementary school. I found out that my best friend’s older siblings were homeschooled off and on during middle school because they were worried about school violence. 

And that’s all I really knew about being homeschooled until I went to college. There, I became friends with one of my classmates, Nick. I thought he was a really cool guy, and then I found out he was homeschooled during high school. I was like, “Wait. Cool and homeschool? Together? Is that really possible?”

I came to find out that it was possible, and Nick seemed to have really enjoyed his time being homeschooled in high school. He said that he would get all of his schoolwork done in the first few hours of the day, and then he’d have the rest of the day to pursue his own interests. He could practice sports, play the piano, hang out with friends after they got done with public school, whatever. He had tons of freedom, and he loved it. The world was his oyster.

College > High School

I didn’t really think much more about Nick’s experience at the time, but looking back, I enjoyed college way more than high school for the same reasons Nick enjoyed being homeschooled during high school. In college, if I could study on my own instead of going to class, I did it in a heartbeat. I could usually learn the material much faster on my own, leaving me with free time to pursue my own goals and ambitions. Particularly, during my senior year, I had enough free time to start my first business.

Entrepreneurship > College

I had the time of my life building my business. From building the website to designing the logo, I was having a blast. In fact, I was having such a great time that any work not related to my business was becoming a chore: “Required attendance at class? Ugh. Shoot me now.” I’d just sit in the back, working on my business.

After getting accepted to graduate school, I found myself in a real pickle because I couldn’t imagine another 4 years filled with 60+ hours/week of required work. Thankfully, I was able to defer graduate school for a year, during which I tried out full-time entrepreneurship. And after tasting the freedom of entrepreneurship, there was no going back.

7 Reasons I Loved Entrepreneurship

There were many reasons I fell in love with being entrepreneur. Here are some of the major ones I discovered very early on:

1. I was in charge. There was no longer a teacher telling me what to do. I could do what I felt was best for me and my company all day long. 

2. Learning was more meaningful. In school, I’d learn things to pass exams. As an entrepreneur, I was learning things that could be immediately applied. I only learned what I needed to, and what I learned had a far greater impact than earning a higher grade.

3. Learning was more fun. While I did enjoy what I learned in my pre-med classes, I never found myself spending extra time studying an interesting topic. I’d master the material necessary to earn an A on a test. Between raising a family, preparing for medical school, and staying on top of my classes, there wasn’t time for learning for the sake of learning. As an entrepreneur, I rediscovered my natural love of learning (See "How to Make Your Own Homeschooling Board Game").

4. My efforts were rewarded fairly. In school, sometimes I would work extremely hard on something only to have a teacher not like it out of personal preference (think English class.

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5. I was able to work from home! Even just thinking about having to commute to a job makes me cringe. I didn’t even like having to walk across campus to my various classes. I love being able to eat breakfast with the kids, and then walk up to my room and get right to work. 

6. I was able to work hard and socialize hard. When I’m working, I’m working. It was the same in college. I never enjoyed studying with other people (it would just slow me down). I preferred to study hard and then socialize hard. Same is true now. I get my work done, and then I’m free to choose whether to go longboarding on my own, read a book, or go play tennis with a friend. I love this freedom.

7. I was able to be there for my growing family. After just a few months of testing out full-time entrepreneurship, my wife became pregnant with our second son, Will. Our first son, Joseph, still wasn’t sleeping through the night, and due to Lindsey’s intense morning sickness, I was tasked with taking care of Joseph most of the day and night. The flexibility of being able to increase or decrease my hours on a daily basis was a lifesaver.

I now realize that these benefits of entrepreneurship are exactly the same benefits my friend Nick got out of being homeschooled. Becoming an entrepreneur really opened up my mind to the benefits of alternative, flexible lifestyles. 

After about six months of full-time entrepreneurship, I started to realize the potential for living off of passive income. I started taking on fewer clients while building up the online courses I offered. Over time, I was able to cut my work hours down to just 1 hour per workday. This left me with a lot of free time, which I started using to study a variety of topics that interested me, including homeschooling.

What If We HOmeschooled?

In January of 2019 when Joseph was 3 years old, I realized that I might need to register him for pre-school if he was going to attend in the Fall. To my surprise, most of the nearby pre-schools were already completely booked. I thought to myself, “What if we just homeschooled him?” It was at this point that I first considered homeschooling as an option for our kids.

We did a lot of research. I read a variety of blog articles on the subject, read research articles, and we even met with a few different homeschooling families to hear their stories and perspectives. Along the way, I also thoroughly researched alternative styles of education such as Montessori and Sudbury schooling (See "Why Unschooling is Better for My Family Than Sudbury Schooling"). 

Will Our Kids Have Friends?

Through all of this investigation, my primary concern was whether our kids would be able to get enough socializing with kids their age if they were homeschooled. Several things helped ease my concerns.

The first thing that helped ease my concern was seeing the research that shows that homeschoolers are not socially disadvantaged. In a comprehensive study of all research done on homeschooling up to that point, “The authors found no indication that their homeschooling experience had disadvantaged them socially and suggested that it may have in fact contributed to a strong sense of independence and self-determination."¹

Even though the research suggested that homeschoolers are not socially disadvantaged, I still had my doubts. I grew up going to public school, where I made most of my friends. How will my kids make friends if they don’t go to public school? 

It helped for me to consider how I make friends as an adult. I simply participate in a variety of activities related to my interests and then I develop connections with people who are also participating (i.e. participating in a pick-up basketball group, starting up a yoga group, etc). This works well because we start from a place of common ground, allowing us to quickly form friendships. I’d much rather make friends in this context than revisiting public school where I had to sift through all the cliques to find a friend or two who were a good fit.