Financial security in retirement doesn't happen by accident. It takes more than putting money into a savings account and picking out hobbies for later. Keep these six questions in your back pocket over the next few years as you start thinking seriously about what retirement looks like for you.
1. When should you retire?
Your age is only part of the answer. Your retirement fund matters more, and it's the part people tend to shortchange. Fidelity's savings benchmarks suggest aiming for about 10 times your salary by 67. Retire early, and that target climbs, closer to 12 times (Fidelity). Your birthday shouldn't be driving this decision. Where you land on that scale should.
2. Should you move?
Some people relocate after retiring to lower their cost of living, cut their tax bill, or be closer to family. A move can free up real money every month. It can also mean leaving behind the doctors you trust and a community you've spent decades building. Worth thinking through before you commit, not after the moving truck shows up.
3. When should you start using Social Security?
You can claim at 62. Your check will be permanently smaller for it. Research from the National Bureau of Economic Research found that more than 90% of workers between 45 and 62 would come out ahead over their lifetime by waiting until 70. Only around 10% of retirees actually do (NBER research, reported by The Motley Fool). Most states don't tax Social Security at all, only about 8 still do, so this is one area where you live can matter more than when you file (Kiplinger, 2026).
4. What does your portfolio look like?
Your allocation should shift as retirement gets closer, less appetite for risk, more emphasis on investments that can reliably supplement your income instead of chasing growth. And this isn't something you set once and forget. Revisit it as markets move and your timeline shortens.
5. Should you still have an emergency fund?
Yes. A roof repair. A car that finally gives out. A medical bill insurance doesn't fully cover. Even a well-built retirement plan can take a hit from something unexpected. On top of what you've set aside for future medical costs, keep an emergency fund going the same way you did during your working years.
6. Do you have an estate plan?
Net worth doesn't matter here. Naming beneficiaries and putting basic estate documents in place protects the people you leave behind, from unnecessary tax burdens and from having to guess what you would have wanted.
Where an advisor fits into this
Written out as a list, these six questions look tidy and separate. They aren't. Your Social Security timing affects your withdrawal strategy. Your withdrawal strategy affects your tax bill. Your tax bill affects whether moving actually saves you anything. A spreadsheet doesn't capture that interaction well on its own, and honestly, neither does a checklist.
LIMRA's 2026 Retirement Income Readiness Report backs this up: people working with a financial advisor are far more likely to feel prepared for retirement, 77%, against 47% of those without one. Only 40% of pre-retirees currently work with an advisor at all (LIMRA, 2026).
If you're looking for one, check a few things before you commit: whether they're a fiduciary, legally required to act in your interest rather than just recommend something suitable, whether their specialty actually fits your situation (pension decisions and 401(k) rollovers are a different skill set than general investment management), and how they get paid. I've gone into more detail on all three in a separate post on questions to ask before hiring a financial advisor. Same logic applies here.
Planning ahead protects the net worth you've already built and gives you a clearer picture of what's actually ahead. If you'd like to talk through where you stand on any of these six questions, or the pension and Social Security decisions tied to them, reach out. Let's build your retirement together. Visit pereirawm.com or call (877) 997-7113.
Sources: Fidelity, "Average Retirement Savings by Age" (fidelity.com); National Bureau of Economic Research findings as reported by The Motley Fool (fool.com); Kiplinger, "States That Tax Social Security Benefits" (kiplinger.com); LIMRA, "Retirement Income Readiness Report," 2026 (limra.com).
This information is not intended as tax or legal advice. Individuals should consult their own tax and legal professionals regarding their specific circumstances. Social Security claiming strategies should be evaluated based on an individual's unique circumstances. Claiming benefits later may not be appropriate for all individuals. Consult with your financial, tax, or legal professional before making decisions regarding Social Security benefits.