Ten Questions to Figure Out if Homeschooling is for Your Family

When my oldest son was 18 months old, I quit my job and started my own business. Entrepreneurship wasn’t even a goal until I had my son. But after a short 10 week maternity leave, I knew I would do whatever I had to do to create more time with my boy. So I did. 

I started my own law firm and worked from home. We took day trips to the children’s museums, met daddy for lunch, and played outside as much as we could. All of this was done in between court hearings, client meetings, and document drafting. I was juggling motherhood and business and finding success in both! I replaced my 9-5 income in my first full year of business. 

Two years after I started the business, my husband was able to quit his job and join me in practice (he’s also an attorney). At just about the same time, we welcomed our second son and our family of four was opened up to a new world of freedom. 

We made our own schedules, we brought our kids to the office with us, and we traveled a lot! It was glorious. And then Noah turned 5 and it was time to enroll him into kindergarten. We held off as much as we could. We decided to enroll him when he was 5 years, 9 months old instead of the year prior when he was 4.9. 

I had considered homeschooling in theory, but I hadn’t looked into it enough to really know what that would entail or how it would work for our entrepreneurial family. For some reason, I thought it would be harder instead of easier. I shared my thoughts with my husband and I told him this was something I wanted to consider in the future. Little did I know, the future was a mere 6 months away. 

In March of 2020, just like the rest of the world, my son’s school shut down. Here was my chance! The first Monday of the shut down I had created a name for our homeschool, created a daily schedule and planned out our first lessons! I felt like I was made for this and my kids (6 and 2) were actually loving it. They loved “Mommy Teacher” and all of the crafts and hands on learning we were doing. That lasted a week and then distance learning entered the picture. 

In hindsight, we should have just un-enrolled him when distance learning began, but everything was so up in the air and no one knew when the school’s were going to reopen. And I think that’s why it didn’t even cross our minds. My son hated distance learning. He hated sitting at the computer for hours each day and he hated the fact that, not only did he have to tune in to the virtual learning, but then he had more work to do once they logged off. 

We made it through that year by doing the bare minimum. And that was more than enough for me. When it was announced that the kids would be able to return to school the following year but would have to wear masks all day, my husband and I made the personal decision to officially pull him out.  

And we haven’t looked back! 

In that time, we’ve welcomed a third little boy, taken a lot more vacations, including a 32-day vacation, started a few more businesses and moved our family from Connecticut to Hawaii! 

Entrepreneurship made it possible, but homeschooling made us flexible. And that flexibility is priceless. 

Has it always been easy? No! But it’s always felt worth it! The benefits far outweigh any drawbacks or difficulties.  

We agree that homeschooling has added an extra layer of freedom, connection and possibility for our family. And that isn’t something that we are ready to give up. Even once the mask requirement was lifted, we knew that enrolling the kids into school was just not for our family.

If you’re wondering if homeschooling is the right fit for your family, I think it would be beneficial to ask yourself these questions: 

• Why do we want to homeschool?
• Why wouldn’t homeschooling be for us?
• How would homeschooling benefit our family?
• What would change/need to change if we started homeschooling?
• Are we able to endure/make those changes?
• What do I believe are the minimum requirements of homeschooling? 
• Have I done enough research to know the minimum requirements so I can make an informed decision?
• Will I look back and wish that we would have at least tried?
• Will homeschooling further any of our other goals and family values?
• What kind of support would I have if we chose to homeschool? 

I know that homeschooling isn’t for everyone, but for us, once we had a taste of it, there was no going back. 

If you want a more in depth-look at what I mean by each of these questions and how you can answer them, watch my YouTube Video linked below!