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Home » I’ve Worked at My Mother’s Business for Years Alongside My Sister
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I’ve Worked at My Mother’s Business for Years Alongside My Sister

EditorBy EditorFebruary 16, 2026No Comments4 Mins Read
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Working with my family full time was not something I had pictured for myself growing up. Even when I was given a chance to sit down and learn the family business full time, I told myself it would only be temporary.

I had plenty of peers who planned from the get-go to take over their parents’ companies, but not me. Still, my mother was determined to have me learn the ins and outs, no matter what I may end up doing in the future.

Now that I’ve been a full-time employee for seven years, I’ve learned the intricacies of our family business. It isn’t easy, but working with my family has made me appreciate everything I grew up with and the professional skills I’ve gained.

My mother is a businesswoman and my boss

My mom started the companies I now work for in her early 30s. Starting out as a real estate agent, she learned that many of the properties she listed had underground or basement heating oil tanks that needed to be removed and replaced. Instead of coordinating multiple contractors, she started her first company to become a one-stop shop for the entire project. As many of her clients now had new oil tanks, she also started a company to provide oil and service for their heating equipment. The one-stop shop got a bit bigger with the newest addition.

Since my mother has been an entrepreneur her entire life, it’s all my sister and I have ever known. There are many pictures of our mom on job sites while pregnant or with us in strollers, watching the excavators and trailers go by.

Teddy Rainville and sister as kids hanging off a truck

The author and his sister have been involved with the family business for years.

Courtesy of Teddy Rainville



Many of the people who worked in the office felt like family, as I grew up stopping in with my mom and dad after school so they could wrap up their days.

At home, at work, or anywhere we may go, Mom is the boss. I didn’t even know that HVAC and construction were male-dominated fields until my teens because every colleague she had did exactly what she said with little to no questioning.

My role at my family’s company grew over time

As a kid, I would help clean the offices on the weekends. When I was in college, I worked in the office during my summer break. I got to learn just how the daily operations I’d heard about and seen my entire life.

I started answering phones, sending out marketing mailers, and gradually taking on more of the responsibilities my older sister had handled years earlier.

After college, I started working full-time at my mother’s company as an office assistant. Now, I’m a coordinator for job sales, contract writing, bookkeeping, scheduling, and an ongoing list of administrative tasks that keep the businesses running.

Although I never pictured myself working here full time, I try to look on the bright side. I left college not wanting to pursue the degree I ended up with, but I’m still able to support myself and my loved ones while I determine the new path I want to take.

Working with my family isn’t always easy, but worth it

People often ask me if I enjoy working with my immediate family every day. I’d be lying if I said it didn’t have its benefits, like the job security and ease of taking time for family matters.

But it also, of course, comes with an array of challenges.

Having my older sister directly over me as the office manager means that when things get frustrating, she easily treats me like the baby brother. Stern though she may be, she’s always got the right answer and is sure I don’t make the same mistakes twice. Like our mother, she commands a room’s attention and reminds everyone exactly who’s in charge at that moment.

Sure, it is tough to ask my mom for time off without her prying into my personal life to find out why, but my family has always reinforced the value of hard work, dedication, and an unshakable work ethic. I’m learning from the best.

I will always appreciate how lucky I am

Being able to work with my family is one of the luckiest lots in life I could have pulled. The frustrations are real, and the challenges of a small (but mighty) set of family businesses are ever-present.

However, I can never deny the privilege of learning and growing with the ones I love. I’m not sure how long I’ll work in the family business, but I feel prepared for whatever path I may walk next — with a strong base of support behind me.



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