3 people from different generations reveal their biggest money questions

What’s the money question that keeps you up at night?

You’re never too old to ask questions—or to learn new tricks. No matter what stage of financial life you find yourself in, there are bound to be aspects of money management that leave you scratching your head. But it pays to confront the unknown when it comes to your personal finances. The answers you seek may be simpler than you think. This week I asked members of three different generations to tell me their biggest money stumper.


“My girlfriend and I are about to move into our second New York City apartment. We’re upgrading size and amenities, which is great, but also rent, which is not so much. We’ll also be tenants to a couple not much older than us who are first-time homeowners. The whole thing has got me thinking, if we’re helping someone else pay their mortgage every month, what can and should we be doing to build a financial foundation for our own hypothetical future house? This feels like the natural, next big money goal to focus on. So what’s the smartest account to be saving in? How much is enough to save monthly and yearly for a down payment? And as my personal rent crosses the four-digit threshold for the first time, how much longer can I really afford to rent in this city?”

—Chantal Monroe, Queens, New York

Takeaway: If you’re living in an expensive city, planning to buy a house can be a tough ball to add to the daily juggle of making rent, saving for emergencies, and covering other costs like student loans. But a good way to start is by automatically siphoning a portion of each paycheck into a safe, interest-bearing account earmarked for your home sweet home-to-be. For weighing the rent vs. buy question, check out my calculator.

Gen X

“I am baffled by college financing questions. I’m sure there’s something I need to be doing for my four-month-old son, but I’m not sure what. Odds are he’ll want to go to college, and it’s going to be expensive. As amazing as I think he is, he’s probably not going to get a full ride somewhere. It wouldn’t be that hard to set aside $1,000 a year starting now, but if I wait, I feel like it will be impossible. So where to save? I know Florida has some programs that are set up for this, but I haven’t done anything about it—and I should.”

—Anthony Wilkins, Orlando, Fla.

Takeaway: Anxiety about paying for college begins early—in this case, at age four months! That’s good, because the sooner you start, the better. Set up a 529 college savings account with automatic deposits as soon as your kid is born. Most states have their own plan—including Florida.


“I’d like to have a better understanding of my investment portfolio. I meet with my advisor every quarter, and I’m happy with the level of fees I pay. But your risk changes as you get older. People in my generation should be invested in less risky areas because, let’s face it, we have less time to recoup any losses. I’d like to understand why a certain percentage of my money is in low-risk bonds, and how that percentage increases over time. That way, I could make sure that my portfolio is in balance with where I’m going in life.”

—Lisa Robinson, Davis, Calif.

Takeaway: Our financial needs change as we age, and there are always new questions that need answering. A low-fee financial advisor can help you reduce stress and avoid mistakes when it comes to your investment portfolio. Just make sure you’re comfortable with your level of knowledge about how your portfolio is set up for the long run.

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