My husband and I have discussed turning his passion for woodworking into a full-time business countless times. But there just hasn’t been enough time in the day to plan it. Between five kids, his job as a middle-school math teacher and my writing career, we’ve often felt like we were on a nonstop hamster wheel. Having spare time was a luxury.

When our state shut down last spring, we suddenly had nothing but time. Though we were adjusting to working from home with kids, his virtual teaching hours were shorter than a typical school day, so he could devote more time to his side business. He finally got a real taste of what it could be like to work for himself, so we decided to take concrete steps toward becoming a full-time entrepreneurial family.

Here’s what we’re doing now to reach our financial goals.


I got a bit lax with our budget last year. After having my fifth baby and our home getting hit by a freak hailstorm (insurance covered a lot, but not all of the damage), we’ve been trying to keep up with extra expenses.

But trading my husband’s guaranteed paycheck for unpredictable freelance income meant it was time to focus. I’m back to watching our family’s expenses and have shaved off close to $2,000 a month so far. I got rid of subscriptions we can live without and cut back on our grocery bill.

Plus, without kids’ sports, church, weekends away, babysitters or dinners out, we also don’t need new clothes and shoes or convenience foods. I even decided to save my entire paycheck to see how long we could make it on one income, and to challenge myself to save even more money.

We also worked with our lender to lower the interest rate on our mortgage to free up more cash and are taking in a small monthly rent from my parents, who are living with us while they build their retirement home.


Cleaning up our budget has meant we can contribute to our “freelance fund,” money to help pad our income in the first few months while my husband builds his customer base. We’ve put away around six months of living costs.

Our accountant has been helpful in making sure we have a handle on our expenses, estimated tax payments and anticipated profits.


By far, the most terrifying part of going full-time freelance is losing my husband’s health insurance. Buying insurance for a family of seven is no small feat.

I researched health care for the self-employed and got quotes from a medical insurance agent. Taking a hard look at our costs was necessary for understanding our potential expenses. Replacing our current plan would cost about $2,000 a month. (On the bright side, health insurance premiums can be written off as a business tax expense.)

We added that cost, along with my husband’s retirement contributions, to the amount of income his side business would have to replace. And each month, we evaluate whether we hit that number.


While my husband is still employed, we're paying some startup expenses. He had already been building up his business for well over a decade, slowly adding tools as he could afford them, but there are still a few big purchases to make.

Rather than taking out a business loan, we’ve been reinvesting his profits into new tools, supplies and materials, as well as hiring a logo designer. I’m also helping him build a website, learn search engine optimization, run his Facebook page and maintain his LLC.


Having freelanced full-time for over a decade now, I know the importance of multiple revenue streams — after all, even regular clients can disappear. So we've monetized our hobby farm, where we raise and sell cows and harvest hay for local farmers.

In 2020, we doubled our livestock numbers and explored ways of increasing our margins, such as doing more of the labor ourselves and ensuring our cattle are pasture-raised (which can earn a higher price). That brought in a few thousand dollars’ profit — a good start. We have a plan to double our numbers again this year.


There are so many nuances that come with going out on your own: The emotional roller-coaster of working for yourself; adjusting to increased time together as a family; navigating marketing when all your family and friends are watching. So we are absorbing wisdom from family members who have recently opened businesses. My husband grew up on a second-generation family farm, the ultimate entrepreneurial enterprise, so you could say working for himself is sort of the family business.

We know there may never be a perfect time to make this leap, but we're listening to the people around us who have succeeded. Until it happens, we’re doing all that we can financially to make our entrepreneurial dream a reality.

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