The 10 Social Security Questions Your Financial Advisor Secretly Hopes You’ll Ask

Look, we need to talk about Social Security. I know, I know. You’d rather get a root canal while listening to elevator music. But here’s the thing: understanding these benefits could mean the difference between retiring comfortably and spending your golden years eating cereal for dinner. Not the good cereal either. The generic stuff.

So grab your reading glasses (or squint really hard) and let’s dive into the questions that actually matter when planning your retirement benefits. Your future self will thank you. Probably with a nice card. Maybe some cookies.

Why You Need Someone Who Speaks Fluent Government

Financial advisors are like translators for bureaucratic nonsense. You know those Social Security statements that read like they were written by robots having a bad day? Advisors decode that stuff for a living. They’re the heroes we need but don’t deserve.

A good advisor helps you navigate the maze of rules, regulations, and random requirements that make up our beloved Social Security system. They’ve seen it all: the good decisions, the face-palm moments, and everything in between. Think of them as your retirement GPS, except they won’t tell you to turn left into a lake.

Question 01: “So My Ex Is Actually Worth Something Now?”

Plot twist of the century: If you were married for at least 10 years, you might be able to collect benefits based on your ex-spouse’s work record. Yes, really. The divorce settlement that forgot to mention this little gem could actually help fund your retirement.

Here’s the kicker. You can collect these benefits even if your ex remarried someone else. Even better? They don’t even have to know about it. It’s like getting a secret bonus for surviving a decade of their questionable life choices. The government’s way of saying, “We get it. Here’s some compensation.”

Question 02: “Will Social Security Even Exist When I Retire?”

Ah, the million-dollar question. Or should I say, the 75-cents-on-the-dollar question? Current projections show the trust fund running low around 2035. But before you start stockpiling canned goods and learning to grow your own vegetables, remember this: benefits won’t disappear entirely.

We’re looking at roughly 75-80% of current benefit levels if nothing changes. It’s like ordering a large pizza and getting a medium instead. Not ideal, but you won’t starve. Smart money says Congress will eventually do something about it. Probably at the last possible second, because that’s their style.

Question 03: “Can I Work and Still Get My Check?”

Good news for workaholics and people who get bored easily: You can work while collecting Social Security. Bad news: If you’re under full retirement age and earn more than $22,320 in 2025, they’ll temporarily reduce your benefits.

Think of it as Social Security’s way of saying, “Pick a lane, buddy.” But here’s the secret: Once you hit full retirement age (67 for most folks), they recalculate and give back what they withheld. It’s like a forced savings account, except you can’t access it to buy that boat you’ve been eyeing.

Question 04: “What’s This COLA Thing? A Soft Drink?”

COLA stands for Cost-of-Living Adjustment, not your favorite fizzy beverage. It’s the government’s attempt to keep your Social Security payments somewhat aligned with inflation. The 2025 increase was 2.5%. Exciting stuff, right?

To put that in perspective, if you’re getting $2,000 a month, you’ll now get an extra $50. That’s almost enough for… well, not much these days. Maybe a tank of gas if you drive a really small car. Or a fancy coffee drink if you skip the extra shots and whipped cream.

Question 05: “What If I Want to Wait Past 70?”

You could wait past 70 to claim benefits, but why? That’s like leaving money on the table because you enjoy looking at empty tables. Your benefits stop growing at 70, so waiting longer just means missing out on checks for no good reason.

Unless you’re conducting some sort of social experiment or have a really weird bet going, take the money at 70. Your financial advisor will back me up on this. They might use fancier words and show you graphs, but the message is the same: Don’t be stubborn. Take the money.

Question 06: “How Do I Squeeze Every Penny Out of This System?”

The classic optimization question! The textbook answer is simple: Wait until 70. But life isn’t a textbook, and neither is your retirement plan. Maybe you need the money at 62. Maybe your health isn’t great. Maybe you want to travel while you can still remember where you parked at the airport.

This is where advisors earn their keep. They’ll run scenarios, crunch numbers, and help you figure out what makes sense for YOUR situation. Not your neighbor’s situation. Not what some guy on the internet said. Your actual, real-life circumstances.

Question 07: “They Tax My Benefits? Seriously?”

Welcome to America, where we tax your taxes! If your combined income exceeds certain thresholds, up to 85% of your Social Security becomes taxable. It’s like getting a gift and then being charged a gift-receiving fee.

The thresholds haven’t been adjusted for inflation since the Reagan administration, which means more people get caught in this trap every year. Your advisor can help you strategize around this, maybe by timing other income sources or doing some fancy footwork with retirement account withdrawals.

Question 08: “Do I Qualify? I Had Some… Interesting Jobs”

Most people qualify after working about 10 years in jobs where they paid Social Security taxes. Yes, even that summer you spent as a professional sand castle consultant counts (if you paid taxes on it). The system uses your highest 35 earning years to calculate benefits.

No 35 years of work? They’ll throw in some zeros, which is about as helpful as it sounds. This is why those gap years you spent “finding yourself” might cost you in retirement. But hey, at least you found yourself, right?

Question 09: “What About My Spouse? They Put Up With Me”

Your long-suffering spouse can receive up to 50% of your benefit amount. It’s the government’s acknowledgment that marriage is work, and somebody should get paid for it.

The rules get complicated when both spouses have work histories, there’s an age gap, or someone wants to claim early. This is prime advisor territory. They’ll figure out the optimal claiming strategy while you argue about whether to retire to Florida or Arizona.

Question 10: “When Should I Take the Plunge?”

The golden question! Claim at 62 and get about 70% of your full benefit. Wait until 70 and get 124%. It’s like choosing between a bird in the hand and 1.77 birds in the bush.

Your perfect claiming age depends on approximately 47 different factors, including your health, other income, whether you like your job, and your feelings about leaving money to heirs. An advisor will help you sort through all this without losing your mind.

The Bottom Line

Social Security is complicated enough to make your head spin, but it’s too important to ignore. Getting professional help isn’t admitting defeat; it’s admitting you have better things to do than decode government regulations.

Find yourself a good financial advisor who can translate this mess into actionable advice. They’ve seen every mistake in the book and can help you avoid them. Plus, they usually have good coffee in their offices. That alone might be worth the visit.

Remember, the goal isn’t to master every obscure Social Security rule. The goal is to retire without eating cat food or moving in with your kids. A good advisor helps you achieve that goal while maintaining your sanity. And possibly your sense of humor.