After 3 weeks in Illinois, I came back to Colorado this Sunday (Monday, technically, by the time our plane got a gate).
Trying to get back into work this week has been a struggle.
I’m doing much better at completing non-work tasks where I don’t have to think too much: dog walking, cleaning, and running various errands.
I’m just not feeling all that creative lately. So when I can’t focus, and don’t get enough stuff done, it’s hard not to feel frustrated.
With that in mind, this newsletter will dig into a subject I can talk about with ease.
In reflecting about my dad’s life, I’ve been thinking about the lessons he taught me about becoming a successful entrepreneur. 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’s what I’ve taken away from his experience and applied to my own entrepreneurial journey:
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.
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.
- On a related note, 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 Air Pods — 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. 😂
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 to hold yourself 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. Ultimately, it’s about finding the right balance for you.
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.
- On that note: 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.
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.
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.
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).
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 to land on the right solution. The path forward isn’t always clear but with the right attitude, you can do amazing things.
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.
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 for helping me to forge a path forward.
Until next time,
Maddy Osman, The Blogsmith