5 Financial Planning Questions to Ask in Your 50s

Turning 50 is a big milestone – one that comes with more birthday cards about creaky knees than you’d like. But it’s also the perfect time to check in on your finances.

You’re close enough to retirement for it to feel real but still far enough away to make meaningful moves.

So, where should you start? With the right questions.

Key Takeaways:

• Know your retirement number – how much you’ll need to retire comfortably.
• Rethink your investments – make sure they match your retirement timeline.
• Plan for healthcare costs – Medicare doesn’t cover everything.
• Decide when to claim Social Security – timing matters.

1. Am I on track to reach my retirement savings goal?

Let’s cut to the chase: Do you know how much you’ll need to retire comfortably – and are you on track to get there?

If you don’t have a specific number, now’s the time to figure it out. A common rule of thumb is that you’ll need about 70–80% of your pre-retirement income annually (Learn more about creating an income stream here).

But everyone’s retirement looks different. Want to travel? Help your kids buy a home? Those dreams come with a price tag.

Pro tip: To create a personalized goal, use a retirement calculator or, better yet, meet with a financial adviser to crunch the numbers. And if you’re behind? Don’t panic. Your 50s are prime time to catch up, thanks to higher contribution limits for 401(k)s and IRAs.

Here’s how it works in 2025:

• 401(k) Contributions: You can contribute up to $23,500. But if you’re 50 or older, you get a “catch-up” bonus of $7,500, raising your total limit to $31,000.
• IRA Contributions: You can put in up to $7,000, plus an extra $1,000 catch-up contribution if you’re over 50 – for a total of $8,000.

Plus, there’s more good news for those nearing retirement:
SECURE 2.0 Rule: If you’re between 60 and 63, your 401(k) catch-up limit jumps to $11,250, giving you even more room to save.

Taking advantage of these higher limits can give your retirement savings a powerful boost – especially with the tax benefits they offer.

2. Should I adjust my investment strategy?

Your 50s aren’t the time to gamble with your retirement savings, but that doesn’t mean you should hide everything under the mattress either.

Here’s the balance to strike:

• Growth for tomorrow: You still need your money to grow to outpace inflation.
• Protection for today: But you also want to shield some of it from market swings.

This could mean shifting more toward bonds and dividend-paying stocks for your retirement timeline.

Pro tip: Now’s a great time to rebalance your portfolio and ensure it matches your goals and risk tolerance.

3. How will I cover healthcare in retirement?

No one likes to think about healthcare expenses – until they arrive with a giant bill attached. On average, a 65-year-old couple may need over $315,000 for healthcare in retirement.

Remember: Medicare doesn’t cover everything, such as dental, vision, hearing aids and most long-term care.

The good news? You can plan for it.

• Contribute to an HSA (Health Savings Account) if you have one. It’s a triple tax-advantaged way to save for healthcare. (But wait! There's more reasons for having an HSA in retirement.)
• Review your insurance options. This includes disability insurance if you’re still working and long-term care insurance, which is often cheaper if purchased in your 50s.

4. When should I claim Social Security?

Social Security can feel like a puzzle – lots of pieces, and the picture changes depending on when you claim.

Here’s what you need to know:

• Wait until 70: Your monthly benefit grows by about 8% annually after full retirement age (typically 67).
• Claim early at 62: You’ll receive less, but you’ll start sooner – sometimes useful if you retire early or need the income.

Pro tip: Run the numbers based on your expected lifespan and other retirement income. If you’re married, consider how your decision will impact spousal benefits.

5. What’s my plan for debt and taxes?

Debt and taxes don’t magically disappear in retirement. In fact, they can take a bigger bite out of your savings.

Your 50s are a smart time to explore ways to manage both.

Tackle Debt:

• Consider the benefits of paying off your mortgage before retirement. A lower monthly budget could give you more financial freedom later.
• Focus on eliminating high-interest debt, like credit cards or personal loans, which can drain your savings.

Plan for Taxes in Retirement:

• Estimate your tax bracket in retirement and determine if a Roth conversion makes sense. Paying taxes now could help you enjoy tax-free withdrawals later.
• Look into tax-advantaged accounts like IRAs, 401(k)s, and HSAs to maximize savings and reduce taxable income.
• Be strategic with withdrawals. Know which accounts to tap first to minimize your tax bill over time.

Taking these steps now can help you enter retirement with more financial flexibility—and fewer surprises from Uncle Sam.

The Bottom Line

Your 50s are a financial sweet spot. By asking these questions and acting on the answers, you’ll be setting yourself up for the retirement you want.

So, what’s your first move? A retirement review with a financial adviser could be a great place to start. After all, the best time to plan for retirement is yesterday. The second-best time? Right now. 

Schedule your free retirement review today!