By Josh Katzowitz, WCI Content Director

The richest among us still believe they have money problems. The most financially literate people we know still question themselves. The most confident investors that surround us still wonder if they’re making the right moves.

I question myself and sometimes struggle with financial decisions. I’m sure you do, too. I bet even WCI founder Jim Dahle and Warren Buffett and Paul Merriman and probably even Taylor Larimore do as well. I know financial journalist/podcaster Paula Pant does.

And I talked to plenty of people at WCICON24 (which you can watch in our Continuing Financial Education 2024 course) who told me about their biggest financial worries and struggles. With the exception of Pant, who was more than happy to talk on the record, I’ve kept the responses anonymous so the attendees could speak freely about what they worry about when it comes to their money. Maybe you can relate, as well.

The Biggest Struggle in Your Financial Life

Pant runs the Afford Anything empire, and if you listen to her podcast or if you take any of her courses, you know she’s a highly competent and highly skilled financial expert and communicator. But she’s also made mistakes, and her business is probably still affected by her past decisions and because those struggles continue into today.

As she told me when I asked about her biggest struggles in the financial realm:

“It was a reluctance to hire within my company as fast as I could have,” said Pant, one of the WCION24 keynote speakers. “We have a few employees, but I tend to be slow to hire. The responsibility of knowing that somebody’s health insurance and retirement benefits depends on my business doing well, that’s daunting. My business grows more slowly than it needs to because I drag my feet for far too long for hiring and leveling up.”

Here’s how other WCICON24 attendees answered (and remember WCICON25 will be here before you know it; make sure to register for what is sure to be the best conference yet).

• “We’re looking to generate more wealth so we can create more impact. I have a business, and growing that and scaling that is relatively new. I didn’t go to business school. That’s the biggest challenge. There are definitely moments where I don’t know what I’m doing. I want to help as many people as possible. How can I make that happen? There are times I can fool myself into thinking I’m a failure. But we’re lucky that we don’t really have that much to worry about.”
• “I own a condo in Hawaii. In part, I wanted it as a second home, and in part, I wanted it as a business investment for a short-term vacation rental. It’s more of an ethnic or cultural thing. In order to rent it out to people who want to be there, I have to pay for a country club (membership). I don’t see myself as a country club person. I am a very down-to-earth person who’s not into exclusivity. Yet, I have to shell out the money for that. It’s more of a moral dilemma than it is a financial dilemma. But I do still have to shell out the money.”
• “Balancing spending and saving. Sometimes I think we spend too much but we’re also meeting all of our savings goals. But we could always be saving and investing more. How much is enough?”
• “We are at the age where we’re transitioning to working less and looking to retirement. We really have to shift our mindset. I have to learn a new set of skills instead of learning to save everything. How does this math work, especially because my husband is nine years older than I am? We have different outlooks for retirement. He’s like, ‘I’m kinda done,’ but I could keep going. It’s a new mindset and a new skill set.”
• “Getting my kids through college and maybe graduate school. In an ideal world, it would be us getting the kids through college debt-free and graduate school debt-free or with minimal debt—just enough for them to understand and appreciate what it’s like to have debt and how difficult it can be to pay down in your early career years.”
• “We have all these goals, and unless you win the lottery, these goals won’t happen overnight. You have to work toward it. It feels good, the idea of being financially literate or becoming a millionaire, neither of which I am. And yet, my goal isn’t to wish life away. But it’s to enjoy the present moment and not get ahead of myself while still focusing on the future.”
• “I’ve fired two financial advisors because they gave me bad advice, and I started to do it on my own. Then, I gave myself bad advice. So, I have some catching up to do. To be where I want to be, I have to make some changes.”
  
• “We are debt-free, and once I became debt-free, I went part-time. I’m the sole breadwinner for a family of four; my husband is a stay-at-home dad. I don’t really consider myself a super saver, but I still have issues with letting go and spending money on things that my mom or other people during my upbringing would say are not necessary. My mom always said, never pay someone to do something you could do yourself. That applies to lots and lots of things. When we do stuff, like even coming to this conference, I have trouble spending money.”
• “I think we’re doing pretty good. But one of the things I wish is that we could save more. One of the things I’ve noted over the last several years is that our fixed costs keep going up and up. That makes it harder to save. Before we had kids, I was able to save a lot. Now, I have three kids: 5, 4, and 2.”
• “Most of what we’ve done feels very boring. All the investment stuff I’ve done in my life is boring and simple. It’s finding the balance of being safe and simple but being a little more aggressive and leveling up. We’re very happy, but we won’t be able to live a different way or be more charitable if we don’t level up. If we keep doing the same things, we’ll never be able to donate $100,000 to a charity. If we expand and find new opportunities, maybe there is a little risk but maybe there’s a lot of upside.”
• “Two-fold. I have loans. I took out a ton of private loans, because my family had no money. Then, I defaulted on a loan getting out of college. There’s a big burden on people who were told to go to college. They were overqualified for jobs and positions while they were transitioning to grad school. I was making no money, and I had nobody in finance to advise me. I defaulted on a loan. It’s not because I didn’t want to pay it, but there was no way to pay. This knock on my record hit me credit score-wise; it hit me lending-wise. The biggest financial burden is an emotional one, which is to think that something is wrong with you personally. Having to overcome that emotional burden allows me to address that nobody teaches you finances when you’re 21 and your family isn’t over there and there’s no money to support you. You did all the things the American dream told you to do. But people take hits on their credit financially, and no one is talking about it.”

More information here:

Your Biggest Money Mistakes

What We Learned Financially from Our Parents and How We’re Passing It on to the Next Generation

4 Frugal Things I’ve Done Lately

Money Song of the Week

I’m not much of a country music guy, and I’m not much of a boat guy either. But I found myself in both realms at the same time recently, and sometimes, two things you don’t much care about combine together to form the perfect little moment.

While the WCI staff was on its retreat to Lake Powell in southern Utah, a bunch of us were out exploring a slot canyon that you can only access via watercraft. On the way back to our temporary residence as dusk grew darker, Chris Janson’s Buy Me a Boat began blasting through the boat’s speakers. I looked at Jim Dahle, who was driving; he looked at me, who was just riding. And we both said at just about the same time, “Money song of the week.”

So, here it is.

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Not shockingly, the 2015 tune is about buying a boat. As far as I can tell, it’s as simple as that.

As Janson sings,

“I wish I had a rich uncle that’d kick the bucket/And that I was sitting on a pile like Warren Buffett/I know everybody says/Money can’t buy happiness . . .

But it could buy me a boat, it could buy me a truck to pull it/It could buy me a Yeti 110 iced down with some silver bullets/Yeah, and I know what they say/Money can’t buy everything/Well, maybe so/But it could buy me a boat.”

I imagine Janson now has made enough money to comfortably buy a boat (even if it’s not always the wisest financial decision), because the song managed to get him a major label record deal. Which is nice, because Janson said the guy in the song is actually him.

“A lot of times, we sit down and try to write a song for someone else, or even me, or whoever it might be . . . But this time, we just sat down to write something that was fun, that we both felt was cool, and we both had Yeti coolers outside in our trucks,” Janson told The Boot. “I’m sort of an outdoorsy, hunter-fisher guy, and [co-songwriter Chris DuBois] is, too. Everything just sort of naturally fit: The Powerball lotto, everybody’s doing that. We just picked little things from life and put it in a song. The ‘redneck, white trash, blue collar’ stuff, that’s really true to life for me. That’s exactly how I grew up, so it’s a real biopic song for me.”

The song isn’t necessarily meant for a dude like me, but next time I’m on the water, I’d be happy to listen to some more country music and drink a couple of Coors Lights. Or maybe give me some yacht rook and an Old Fashioned. Drink enough of those, and I’m sure I could become a boat guy after all.

More information here:

Every Money Song of the Week Ever Published

Tweet of the Week

It’s certainly a fine line to walk between taking care of your patients and taking care of yourself. But yes, maybe taking care of your employer shouldn’t even be in the equation.

What’s your own money struggle right now? Is there a way to fix it? How are you solving your financial issues? Comment below!

[Editor’s Note: For comments, complaints, suggestions, or plaudits, email Josh Katzowitz at [email protected].]