11 Entrepreneurship Lessons I Learned From My Dad

7 min read
By: Maddy Osman

2019 has been a rough year.

There have been so many high highs and so many low lows.

Specifically, I’m talking about achieving major life milestones like buying a house. Then contending with all the stresses that come with this new responsibility — including weeks of long nights to get in move-in ready.

Then, there’s the excitement of planning a future with the love of my life. But the sadness that my dad won’t be there to celebrate with me.

He died two weeks ago. It was unexpected and I still don’t think that I’ve fully accepted it.

To stay busy, I made myself responsible for a number of important action items that needed to be taken care of before his wake. I had many opportunities to reflect on his life and my own while organizing photos for a slideshow, writing his obituary, and delivering the eulogy at his funeral.

Writing the obituary, eulogy, and now this article has definitely been a cathartic process.

Not only was my dad a great man — he was my business mentor.

I always felt confident charging forward with my freelance business knowing that I could get advice from someone who had my best interests at heart.

In reflecting about my dad’s life, I’ve been thinking about the entrepreneurship lessons he taught me that have helped me to find success.

He built a company, Independent Systems, that kept him quite busy. Eventually, he grew it into an asset that he sold to fund his retirement.

Here are the entrepreneurship lessons that I’ve taken away from his experience and applied to my own entrepreneurial journey:

#1: It starts with a good education.

My dad came from nothing. He didn’t have support at home from his parents.

He quit high school because he didn’t feel like he fit in. But education was absolutely important to him. He got his GED, joined the Navy, then went to community college to learn more about programming (an entirely new field at the time).

Later in life, during his first marriage, he completed a bachelor’s degree at Elmhurst College.

Even with the odds against him, he pushed through and prospered. I worked hard in college to try to be worthy of the gift of education that my parents graciously bestowed upon me.

You’ve got to learn the rules before you can break them. An education provides a solid foundation from which to build your own business. It can also be the proxy by which you meet connections that help your business grow.

#2: You must justify your offering ASAP or pivot.

My dad was a hustler from the very start.

In the Navy, he made extra bones lending cash with interest. My mom recently told me about some of his other hustles: selling coconuts in Miami and launching a biorhythm measurement company in the 70s.

To be sure, not all of my dad’s business ideas panned out but that was OK with him.

He was always excited about the possibilities and gave himself the opportunity to explore his passions. If he couldn’t quickly justify the time and money he put into these various ventures, he just pivoted to the next idea.

#3: Always be curious.

The world moves fast. My dad helped me to see that your professional life can be multi-faceted.

You don’t have to stay with one company, forever. In fact, for your sanity, you’d be better off exploring new ideas as they inspire you.

As the world changed, so too did technology — and my dad did a great job of keeping up. One of the last gifts his kids pitched in to get him were AirPods — I’m not even fancy enough for those!

One of my favorite stories about him, though, was when I was back in elementary school and he had just gotten a shiny new DVD player. He taught me how to use it… then promptly purged those same instructions from his brain to make space for more important things.

I had to turn the device on for my parents whenever they wanted to use it. 😂

#4: You can enjoy flexibility so long as you don’t take complete advantage of it.

Being the boss is hard, if only because you have yourself to hold you accountable for getting stuff done.

My dad loved to travel and we took many family trips around North America and Europe. But my dad never left the house without his computer and access to the Internet.

Don’t get me wrong — he absolutely made time to enjoy whatever exotic locale we were visiting. But he also knew that getting up early to log a few work hours or catching up on the weekends meant that he’d be in a better headspace to enjoy his time off.

All I’m really trying to say is that in a regular job, your boss manages you. As an entrepreneur, you have to become the boss of yourself. And it’s really hard.
It’s a lot easier to tell yourself “I can do whatever I want and worry about growing my business tomorrow” but if you let yourself fall into that mindset over the long term, you’re going to have problems.
You always have to think about “What can I move my business forward today?” and commit to whatever that answer is.
So relating it back to this idea of enjoying flexibility without taking advantage of it… it means that I can work wherever I want around the globe. I can travel to see my mom or friends in other states really whenever I want — that’s my prerogative as an entrepreneur who doesn’t have a boss who has to approve my time off.
All that said, I can’t just travel and goof off the whole time — I have a business to run. I still need some semblance of a schedule during the day — but I can enjoy the flexibility of being able to work remote when my workday is over.

Ultimately, it’s about finding the right balance for you and the needs of your business.

#5: Anything worth having is worth working hard for.

My parents valued two things more than anything else: travel and education.

They made sacrifices to ensure that their daughters could benefit from both, which meant that they didn’t have a lot of extra money to spend on more frivolous things. But if we wanted something, they gave us a path to earning it ourselves.

I developed expensive taste as a young child, obsessed with horseback riding. To earn my horseback riding lessons, I cleaned my dad’s office once a week. It absolutely taught me the value of money and prioritizing spending on the things that truly made me happy.

#6: Your business can be a vehicle to teach your kids important life lessons.

I’m Exhibit A, the case in point.

I learned so much from observing how my dad ran his business and hope to share that with you, too.

#7: Your business can also provide an opportunity to share the wealth with the people you care about.

In his final years as the owner/operator of Independent Systems, my dad brought on my step-brother, J.P., to run the sales department.

It was thanks in part to J.P.’s connections that my dad was able to sell the company and share the proceeds of the sale with his only son. This was a great pleasure to my father, who only ever wanted the best for his family and the people he cared about.

After all, the business was a means to an end for creating a better life than the one he was born into.

#8: The customer is always right.

When my dad came to visit me in Denver just a few months back, we were chatting about one of my newsletters and he had misunderstood something I’d written that was vague and negative.

He thought it was about a client but it was actually about a business I’d interacted with as a consumer. Regardless, the conversation reinforced one of the things he considered as important for running a business: always treating clients in the highest regard.

It costs nothing to hold yourself to high standards and be professional regardless of what life throws at you.

#9: Treat your employees/contractors well.

I had the opportunity to meet one of my dad’s past employees at his wake and could tell how genuinely sad he was about the news of my dad’s passing.

But this wasn’t the first employee of my dad’s that I’ve met or interacted with.

When I was just starting middle school, I’d bike home and would often make a stop at my dad’s office. Shooting the shit with his employees, I uncovered a passion for learning about computers.

At the time, this involved learning CSS/HTML and how to use Photoshop. This eventually led to an awesome college job and a marketable skill that helped me feel confident in taking my freelance business full-time.

It all started in my dad’s office, developing a love for creation, surrounded by professionals who found joy in the work environment my father created (and who didn’t mind putting up with the boss’s kid).

#10: Don’t be afraid to get your hands dirty to get to the bottom of an issue.

A true DIYer, my dad wore many hats in his business. He had a knack for always finding the right approach to solve whatever issue was currently plaguing him and didn’t mind if it took long hours of research to land on the solution.

The path forward isn’t always clear but with the right attitude, you can do amazing things.

#11: Don’t sweat the small stuff or past mistakes.

In business and otherwise, my dad wasn’t one to get caught up in problems that he couldn’t change.

He knew that life is too short to get caught up in worry. So don’t let yourself get caught up in regret over the past — use it to forge a path forward to a beautiful future.

Final thoughts: 11 entrepreneurship lessons I learned from my dad

It’s hard to really comprehend how different life will be without having my dad here to help guide me. I absolutely took advantage of learning from his savvy business acumen during his life, calling him whenever I needed his advice for everything from client issues to tax questions.

My mom keeps saying that she’s looking for a sign from him that’s he’s passed peacefully on to the other side. I’m not sure if or when she will get it. But I can see my dad in each and every one of you who has taken the time to share their condolences, their experiences, and their support during this difficult time.

Thank you.


Maddy Osman

The Blogsmith

Maddy Osman is the author of Writing for Humans and Robots: The New Rules of Content Style. She's a digital native with a decade-long devotion to creating engaging, accessible, and relevant content. Her efforts have earned her a spot in BuzzSumo’s Top 100 Content Marketers and The Write Life’s 100 Best Websites for Writers. She has spoken for audiences at WordCamp US, SearchCon, and Denver Startup Week.

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Your dad was an amazing man, and he raised an amazing daughter! Great post and really appreciate you sharing some of his wisdom with us. Sending you positive vibes from the East coast, and thinking of you and your family.