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Two Women, Two Paths: A Story About Money and Fear

Posted by Dan Ore on September 12, 2025
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[Note: if you like me and prefer to listen to things as a story in a podcast format here’s an AI audio version of this post: https://bit.ly/TwoWomenTwoPaths]

So let me tell you about these two women I know. Both live here in Orange County, actually just a few miles from each other. Their stories highlight something I've noticed and learned after 20 years in this business, it has nothing to do with how much money you have.

It's about what scares you enough to actually do something about it.

 

Monica, My Friend Who Actually Did It

I met Monica years ago when she was married to her husband. We were just acquittances , you know? Pleasant enough, but nothing more than that. After her divorce, though, we became actual friends.

We get along because Monica is just like me, she's a bit of a control freak, maybe even a little OCD about it. Everything has to be just so, organized, where she can see it and manage it herself.

While she was married, she always had this feeling in the back of her mind that her marriage wouldn’t last. She didn't want it to happen, but she wasn't stupid about it either. Smart woman.

So when the divorce actually went through, Monica did something that honestly surprised me. Instead of just living off the settlement or alimony, she took that money and started buying rental properties. She started with one property, then got another one, then another. Over the years she built up this little portfolio of rental properties, all in Orange County.

That’s where her OCD kicked in; everything had to be local. Everything had to be within driving distance so she could go check on her properties whenever she wanted, she didn’t want to rely on anyone else.

And look, she's done really well with it. More than 10 years later, she's got this stable income that supports her and her kids. Her house is paid off, she travels, stays in nice places, and drives nice cars. She's completely independent financially.

But here's what's interesting, we've talked about my approach, how I live where I want, and invest where the numbers make sense – as in out of state. She gets it. She understands the math. “Dani,” she's told me more than once, “I know your numbers are way better. I know I could make more money buying in Kansas City or Nashville instead of these expensive Orange County properties.”

 

But she just can't do it. Her personality won't let her. She needs to be able to drive to her properties, walk through them, and meet the contractors face to face. “I know it's not rational,” she says, “but that's just how I am.”

So Monica's successful, but she's leaving money on the table because of her need to control everything. That OCD thing that helps her in some ways also limits her in others.

Justine, The One Who's Still Thinking About It

Now Justine, she's a different story. She actually lives pretty close to Monica, maybe 3 or 4 miles away and they've got similar situations in a lot of ways, but Justine went a completely different direction.

Justine is also divorced and just like Monica, her house is also paid off. She has two teenagers who are about to graduate from high school. She's artistic and sells some of her art, which is nice for her.

She actually has access to more money than Monica ever did. When she was married, she and her husband started a company, and after the divorce, she still has partial ownership. This company gives her a monthly income, and every few years, she gets dividend checks that are pretty substantial. They provided her with new cars, home improvements, family trips, and, if she thought about it, they would provide a down payment on an investment property.

But here's the thing about Justine. While Monica's running around checking on her properties and managing her little real estate business, Justine's having coffee with her girlfriends multiple times a week.

And look, there's nothing wrong with that. Everyone's got their priorities. But Justine will be the first to tell you she's not financially savvy. “Dani, I don't know what I'm doing with money, and it kind of scares me,” she's said to me more than once.

She knows she needs to do something about her financial future and her kids' future, too. She's smart enough to realize that even though this company she has a stake in is doing well now, companies can struggle or fail. Nothing's guaranteed forever.

She's done some things for the kids, put some stuff in place for their future, their college education. But for herself? Really, nothing significant beyond having that paid-off house. And that house, while it's nice and all, isn't going to support the lifestyle she's accustomed to.

Justine's got time. She's not too late to the game. But, and here's the BIG but, she has to actually START. She has to admit to herself, maybe even say it out loud, “I am financially illiterate and it scares the hell out of me.”

 

That's the hardest part for a lot of people. Once you can say that, once you can drop the ego and face it head-on, then you can start learning. But Justine's still in that phase where she hopes everything will just work out somehow.

What's the Difference?

Why am I sharing these two stories? Well, these two women live practically next door to each other. They both went through divorces. They both have access to money. They both have kids to worry about. And they both have themselves to worry about as they get older.

But one of them saw the problem coming and got scared enough to do something about it. The other one probably sees the same problem but is avoiding dealing with it, hoping it'll work out.

And you know what? It probably will work out for Justine. She's not going to end up homeless or anything. But she's going to pay a price for that avoidance, maybe a big price. Can you really put a dollar amount on confidence and independence?

What Can You Learn From This?

Look, if you see yourself in either of these stories, here's what I think you should do.

First, just write down what you want. I don't care if it's on a napkin or the back of an envelope, or a text to yourself. “I want to own three rental properties in five years,” or whatever makes sense for you. The exact numbers don't matter. What matters is writing it down somewhere.

Second, if you feel like you don't know what you're doing financially, just say so. Drop the ego and face it head-on. When you say it out loud to people close to you, you'll be surprised how many of them feel exactly the same way. Even some people you think have it all figured out will tell you they're just as confused as you are.

Once you've done those two things, you're already halfway there. Because the opposite of not knowing is learning, and there's information everywhere these days. YouTube, podcasts, seminars, books. Start reading, start watching, start listening, start learning! And once you listened to a few podcasts or watched a few videos, start asking questions. There are no stupid questions, just the ones that don’t get asked, and trust me, if you are wondering, there are others around you that are wondering the same thing and glad you asked!

Maybe you don't have time, or maybe you need more than passive learning tools. That’s fine,  hire someone to teach you or work alongside with you. Think of it like getting a personal trainer, but for your money.

 

The Bottom Line

Both Monica and Justine are real women. I changed the names but they exist and they both live near my family. You probably know them or women just like them. Hell, you might BE one of them.

Monica deals with tenant problems and contractor headaches. Justine worries about her future and feels guilty about not taking action. Whichever path you choose you are going to have challenges.

But one of them sleeps better at night knowing she can take care of herself and her kids no matter what happens. The other one crosses her fingers and hopes for the best.

Which one sounds like you? AND more importantly which one do you want to be like?

On a more personal note, I want to share with you two things.

First, over the last 20 years, I have been personally assisting everyday people and couples, people no different than you, to invest in real estate and build an investment portfolio just like Monica did.

The second thing I want to mention is that while this story takes place in Orange County, California, and I am also a resident of Orange County, my focus is on out-of-state investing. I add out-of-state properties to my portfolio, and I have helped my clients acquire over 5,000 rental properties across the U.S.

Why am I telling you that? Because over the last two decades, I’ve created a great system and a process to help me and people like you to successfully invest in out-of-state, long-term rental properties.

So if you're reading this and thinking to yourself, buying local real estate is super expensive, or requires a lot of money up front, and the rent earnings don’t match the mortgage payments,  now you understand there is another alternative for you. And that is going out of state.

Going out of state and buying quality long-term rental properties does not require hundreds of thousands of dollars to get started. It doesn’t require traveling to these locations to purchase and maintain. I bought my first property sight unseen while living in a completely different country. But that’s a story for another day.

Bottom line, if you feel stuck, unfocused, and not sure how to start but know you need to start. You’re ready. Let’s talk.

I promise you I'm a terrible salesperson, and because of that, I won't be selling you anything, but I’m going to listen. And I’m going to see if I can help you and more importunately, if we are a good fit.

Not only will there be no sales, there will be no agenda, unless it’s your agenda.

I look forward to hearing from you, and I'm wishing you great success in your next step.

 


All the best, 
Dani
Dani Beit-Or
Simply Do It Investing
Tampa | Houston | Dallas | Nashville | St Louis | Kansas City | Birmingham | Chattanooga
For updates on properties, announcements and more on Telegramt.me/sdi_re

Podcast: Guided Real Estate Investing by Simply Do Itanchor.fm/simplydoit

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