The Ups and Downs of Working in a Family Business | TrueToast Magazine

The Ups and Downs of Working in a Family Business

Family Business Upsides

Even as a child, I was nearly positive that I didn’t want to inherit my dad’s automotive and equipment leasing business.

I also knew, even then, that my dad would never want to retire. Sure enough, he’s now in his 60s and has no plans to retire anytime soon. That means his company keeps chugging along, as I learn how to manage working in the family business.

My Dad, The Restless Entrepreneur

When his business was in its infancy, my dad worked long hours, often not returning home until 10 p.m. on weeknights, and then leaving for work by 8 a.m. the following morning. When I reached elementary school age, he would drive me to school before heading to the office.

While his business has garnered him a great deal of personal and financial success, I witnessed first-hand the toll that the automotive and finance “game” took on him emotionally.

Joining the Family Business
via Steven Van Loy

These stresses he encountered deterred me from wanting to join the family business. At age ten, I told my dad that I didn’t want to do what he does.

I didn’t want to listen to angry, spoiled customers. I didn’t want to walk in the door at 10 p.m. And I really didn’t want to be mentally checked out of every family meal because I was so concerned with what was happening at the office. None of this was intentional on my dad’s part; however, I never thought it was what I wanted for myself.

But life has a funny way of changing your perspective.

Inheriting an Entrepreneurial Mindset

At 28 years old, I’ve found myself completely unsure of what my next career move will be. My Bachelor’s degree is in Communications and Media Studies, and my Master’s degree is in Public Communications. I’ve written, blogged, and managed several social media pages, both for pay and not for pay. I’ve held two separate jobs “in the field” and neither has worked out as I envisioned — though I still freelance on a pretty regular basis. And, I always have loved writing — otherwise, you wouldn’t be reading this.

But as it stands right now, I can’t solely freelance (as much as I may want to). I need a way to pay the bills.

Joining the Family Automotive Business

Finding My Place in the Family Business

I quickly realized that I needed money to make my entrepreneurial dreams a reality. This realization led me to a desk job at the one place I swore I’d never work: my dad’s business.

And despite my background, I’m not managing Facebook and Instagram pages there.

I’m answering the phone. I’m listening to customers beg and plead angrily for an audience with my dad. I’m filing and researching new technology to utilize in the office. I’m creating Excel spreadsheets and typing contracts. I’m out all day on the road, assisting with delivering new cars and bringing old cars to body shops. And, I’m often working on my freelance and unpaid community projects, waiting for something to do.

If you think that sounds all bad, it’s not. Though, there are a few drawbacks to working in the family biz.

Finding My Place

Downsides to Working in the Family Business

As one could imagine, there are a few drawbacks to working with your family. I have seen first-hand the toll that the demands of business ownership has taken on my dad, and at times it can be difficult to manage it all. Below are some of the main cons of working in the good ol’ family business:

My dad is also my boss.

And if you think he’s easy to work for, you’d be very wrong indeed. I learned very early on that showing up late to work was not an option. But I’ve also seen a different side of my dad that I don’t see at home.

I’ve filled the role of the in-house “IT Person.”

While my dad is far more tech-savvy than most Baby Boomers generally are (cue the texts from Mom and Dad jokes here), it’s become part of my job to utilize my prowess as a Digital Native. I’ve kind of given up on getting my dad to use social media to its full potential… but, I’m working on him allowing me to, at the very least, utilize Wix for a new business website!

The schedule changes constantly.

Which doesn’t have anything to do with my dad per se; it’s the nature of his business. And it’s part of why I never wanted to enter it in the first place. We could be on the road, delivering cars to one location, and have to turn around and go in an entirely different direction as a result of one phone call.

You have to watch the person you love the most get hurt.

Customers routinely speak to my dad as though they are the only customers that he has. As though they are the only people who could possibly matter. As though he has not worked hard enough at his job for them, when I know full well that he has (and more). And there is nothing that I can do about it, except watch.

There is such a thing as too much “togetherness.”

If you know me at all, you know that there is no one in this world who I love and admire more than my dad. But, we are such similar people that when we do argue, the argument tends to… how do I put this?… last a long time. And I currently spend more time with my dad than I do with anyone else, as I live at home. You could see why, on occasion, a break is necessary!

The Upsides: How Working with Family Can Be a Rewarding Experience

Of course, working in the family business is not all negatives. There are some very real benefits to working with family, being in an understanding environment, and more. These are my favorite things about working in my dad’s company:

While the schedule changes, it’s flexible.

I can go to appointments during the day that I had a very difficult time scheduling on a full-time, non-family business, work schedule. While I’m not sure if every family business runs that way, I know it’s a great benefit for me at present.

I get to feel as though I’m contributing.

My parents have been more than generous by allowing me to continue to live at home, rent-free, for the past five years. That doesn’t mean I don’t foot my other bills, but not having to worry about rent or utilities or cable is most definitely a load off my mind. And while my dad pays me to work, the knowledge that I’m helping him contribute to our household by working means more to me than any paycheck could.

When there’s nothing to do, I get to do what I want to do.

I may or may not be writing this from my desk… in between phone calls… nothing else need be said, right?

I’m free to stay as long as I want or need to.

My dad isn’t kicking me out of my desk anytime soon. Which is great news, considering I am still weighing my options and deciding what it is I truly want to do. I get to have a flexible schedule, and earn some money as well as employee benefits like health insurance, all in the understanding that this arrangement isn’t meant to last forever.

But, most importantly…

I have gained an even deeper appreciation of what my dad does, and how hard he works. I understand why he often seems spacey when not at the office. I thought I had a solid understanding of what it takes for him to operate his business, but as it turns out, I had no idea. And while there is indeed such a thing as too much “togetherness,” I get to spend time with my favorite person in the world that I’d never get to spend otherwise. And while that time mostly includes work, it includes checking baseball scores all day long, too.


Do you work in a family business? We would love to hear about your experience! Tell us your story and tips in the comments below!

The Ups and Downs of Working in a Family Business | TrueToast Magazine

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