3 Ways To Know If You’re Going To Be A Successful Entrepreneur Over 50

These are probably not what you were thinking

When you think of being a successful entrepreneur over 50, you’re mind probably goes from zero to one hundred. Being a successful entrepreneur either means you’re Warren Buffet or Elon Musk.

Images of home improvements, vacations, and new cool gadgets and toys spring to mind. But those monumental achievements of those entrepreneur outliers are the extreme end of business success and may have NOTHING to do with your journey as an entrepreneur over 50.

People over 50 dipping their toes in the world of entrepreneurship often forget this. I know I did. Instead of focusing on my small wins, I would beat myself up and let negative thinking hold me back. I would give up if my business idea didn’t reap tens of thousands of dollars in the first six months.

That’s my Lizard Brain — the survival part of my brain that distorts my thinking — taking over my thinking, poisoning my thoughts, and holding me back. I need to calm that Lizard.

Whenever I would hit obstacles in my new business idea, a cascade of Automatic Negative Thoughts (ANTs) would plunge me into a dark hole of deep sadness or anxiety that would take me days or weeks to climb out of.

The ANTs come from my Lizard Brain. It’s all seeming a bit creepy.

I would always be the head organizer of my pity party and would convince myself that I wasn’t cut out to be an entrepreneur. Little did I know there was an in-between worth striving for, The gap — that gigantic gap — between zero and millions of dollars.

And in that gigantic space, there’s room for an unlimited number of businesses for an entrepreneur over 50. There’s never been a better time to become an entrepreneur over 50. But what will make you successful? Well, that’s a good question.

Sticky fingers

I was so excited to drive an ice cream truck when I was younger. Looking back, I realize I gained a ton of entrepreneurial experience running my own retail business selling ice cream and snacks.

I would get up at the crack of dawn on spring and summer mornings and drive my Jack ‘n Jill ice cream truck down to near the shipyards in Northeast Philadelphia. I would join a bunch of other drivers each morning to clean our trucks and refill our summer booty.

It was all manual labor. The days were long, hot, and sweaty. I earned my money in coins and dollar bills. There were piles of money to count each night.

I had no social life and my hands were always sticky. Despite washing and washing my hands at the end of each day, there was always a light stickiness to my touch.

I would be physically spent each day and hit the sack early to be able to make that early morning call back at the headquarters for more truck washing and restocking the pushups, ice cream sandwiches, and soft pretzels.

I learned to work through the physical challenges of what it took to run my own mobile ice cream business. Those early lessons of being a young entrepreneur — hard work, creative marketing, thinking on my feet, and forming great relationships — were programmed into my young brain.

How to be a successful entrepreneur over 50

Your prior experience with being an entrepreneur can certainly help you with executing your new business idea as an entrepreneur over 50.

Besides running a mobile ice cream business, I also had numerous other business ventures that provide me the foundation I need now to be a successful entrepreneur over 50.

It’s my wisdom and insight that are now among my entrepreneurial superpowers. I used to spend a lot of time on the task-focused logistics of a new business idea — websites, marketing plans, social media ad campaigns— but now can really focus on creative idea development, branding, and relationship building.

And passion.

As an entrepreneur over 50, I have mastered inspiration and motivation if I’m passionate about something.

Being an entrepreneur at any age requires long hours of thinking and planning. Without passion for what you’re doing — you’re doomed. That’s why most new business ideas fail and why most entrepreneurs over 50 don’t get past the thinking and planning stage.

So what does it take to be a successful entrepreneur over 50?

1. The work is the win

It’s a concept that’s taken me a long time to fully understand and grasp. I didn’t always realize that the successful path for an entrepreneur is to find something you love doing.

Sure, I’ve run a bunch of businesses by myself but never stuck with most of them because I didn’t LOVE what I was doing. I’d like some of the stuff I was doing, but learned that it takes a lot longer to make a million dollars than I expected.

So the work needs to be the reward. If you don’t love what you’re thinking about doing, then you need to find something else.

2. Hyper-motivated thinking

To be a successful entrepreneur over 50, you need to maximize your power of positive thinking. Ever think about your thinking? The way you perceive, interpret and process things — especially when you’re challenged.

Having a growth mindset is crucial to being a successful entrepreneur over 50. There’s a lot in the business world that’s changing in a short period of time. What it takes to be a successful entrepreneur is also changing. There are new AI (Artificial Intelligence) and VA (Virtual Assistant) tools to help you with repetitive tasks that previously would have exhausted you as an entrepreneur.

You can lean into learning new ways of working smarter as well as incredibly powerful ways to reach people and build community.

Your mind works overtime when you’re passionate about your new business idea. You go to sleep thinking about your new thing. When you get ideas, you run and grab a notepad to get it down on paper.

Because you’re so obsessed with helping people and developing your new business idea into a money-maker.

When you fall in love with your craft and business pursuits, you’re able to give it your best.

3. In it for the long haul

It’s hard to compete and defeat someone that thinks about their craft 24/7. It’s also hard to beat someone who gets so much joy out of what they do.

If you love what you do and you’re ready to stick with it for the long haul — you’re setting yourself up for success.

Regardless of your challenges and stresses, if you get joy out of the new thing you want to do, it’s a win for you. Period.

Don’t let your negative thinking hold you back any longer.

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