What I Learned From Growing Up in an Entrepreneurial Family

by Darcie
young girl with lemonade stand

The year I was born, my dad decided to pursue a new career.

He’d majored in education in college and planned on becoming a high school economics teacher. Instead, he’d ended up teaching a bunch of other subjects to elementary and junior high kids and hating every minute of it.

After 13 years, he had to face the reality that the job was making him physically sick and causing severe health problems. My mom said he had to make a change, or he may not live to see his daughters grow up.

A colleague started talking to him about his own investments and the process of investing, and my dad was intrigued and started to look into financial planning. He ended up taking a one-year sabbatical from teaching which convinced him that he wanted to stay in the industry. 

But with a family to support, he knew he also had to have an income. So he returned to teaching while he got licensed and got the business up and running. Five years later, he bid teaching good-bye and never looked back.

As a child, I was shielded from the stress that goes along with running a business. Now that I’m an adult and considering my own entrepreneurial venture, I talk more with my parents about their experiences and strive to internalize the lessons they share with me.

Here are five things I’ve learned from growing up in an entrepreneurial family.

You have to be committed to your mission.

When you are committing to a side hustle, as my dad did for five years, you can’t be lukewarm about it.

Owning a business requires mental toughness. There will be obstacles, and it will feel nearly impossible to overcome them. At some point, your passion for what you’re doing will be the only thing that pushes you forward.

My dad has attested to this fact. He’s told me about a hundred thousand hurdles he’s had to jump over during his 30-plus years in the industry.

“Every day there’s a new problem,” he says.

But his love for what he’s doing has sustained him.

“I love helping people,” he says. “When they reach their goals and are satisfied, it’s the best feeling in the world.”

You own the wins… and the losses.

When you work for a company, it’s easy to wish you were your own boss. Rules suck, and sometimes they seem arbitrary and counterproductive. I’ve had bosses who throw their power around, and I’ve been shamed for being assertive. It’s not a good feeling and makes me want to be my own boss even more.  But I have to remember that owning a business comes with an entirely different set of stressors.

As an entrepreneur, you don’t have a boss positioned above you, but you’ll still experience plenty of discord from people who don’t see things the same way. 

The upside is that much more is in your control. If you don’t like the way things are going, you make moves to change something.

My dad has told me about wins, like gaining huge accounts, and as well as major losses.

“Most days, there is something good that happens,” he says.

“But every day generally has some kind of hardship, too.”

At the end of the day, the buck always stops with you. If you’re the boss, you’ll get credit for the wins, but you’ll also have to take responsibility for the losses.

You have to be content with hard work.

Both of my parents tell me that there have been many obstacles along the road of getting their business up and and running. When my dad first started out, I was a newborn, and my mom was home with me full-time. My sister was a preschooler of about four-and-a-half years old. My parents had a mortgage to pay and were living solely off of their savings.

My dad’s parents constantly told him he was crazy.

They came from the Great Depression era and highly valued the stability of my dad’s job as a teacher.  

My mom, however, continued to encourage my dad. Her father was an insurance salesman with his own business, so my mom knew that it was possible to be successful working for yourself.

And so, my dad persisted. He continued teaching and also pursued his goal of becoming a financial adviser.

If you’ve ever worked more than one job at a time, you’ve gotten a glimpse at what it’s like to be a business owner. You don’t get to sleep in. You don’t get days off. You have to be ultra-focused. And you have to be okay getting your hands dirty. If this isn’t for you, don’t start your own business.

Your livelihood is always on the line.

Customer service is paramount as an entrepreneur. If you have an off day, it might cost you a client.

When you have your own business, you have to assume that you won’t get a warning or a second chance.

By nature my dad is a positive, extroverted person which makes him great in business. His clients love his friendly demeanor, patience, and unrelenting dedication to helping them achieve their goals. That doesn’t mean he can rest or put his guard down.

In every conversation with his clients, he’s earning their business because at any point a client can change his mind and move their money elsewhere. And he might not get a chance to convince the client otherwise.

You only make money when you’re working.

I can still remember the first time I learned that most people have to ask for time off. This blew my mind because we took vacations at will when I was growing up.

“I had to plan for that,” my dad says.

“I had to work double time before every vacation to make it happen.”

As an entrepreneur, if you want time off, you have to plan for the lost revenue. Your non-entrepreneur friends simply submit a request to their supervisor and then peace out. But as a business owner, there are no paid vacations.

“Here’s a tip from Grandpa Johnson,” he said, who was my maternal grandfather. “Always have an appointment scheduled for the day after you return. That way, there’s no easing back into work. You hit the ground running.”

Growing up in an entrepreneurial family has shown me that it’s very possible to have my own business – it doesn’t seem like an outlandish dream that I’ll never achieve.

But it’s also taught me that owning a business comes with a slew of challenges, and you have to be ready for them. Because if you’re not, it’s never going to work.


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