Alain Guillot

Life, Leadership, and Money Matters

The Retirement Planning Checklist: Are You Really Ready?

The Retirement Planning Checklist: Are You Really Ready?

Retirement isn’t just about having a pile of savings—it’s about making sure your money works for the lifestyle you want. Have you thought about how much you’ll actually need? What about taxes, healthcare, or unexpected expenses? Many people assume they’re set, only to realize later they missed some key details.

Are Your Retirement Savings on Track?

The biggest question most people have is: “Do I have enough?” There’s no magic number, but you do need a plan. A common rule of thumb when it comes to financial planning for retirement is that you’ll need about 70-80% of your pre-retirement income per year, but this depends on your lifestyle, debt, and goals.

Instead of guessing, run the numbers:

  • Total retirement savings – How much have you saved across all accounts, including pensions, 401(k)s, IRAs, and personal savings?
  • Expected income – Will you have Social Security, rental income, or other reliable sources?
  • Monthly expenses – Factor in housing, food, transportation, entertainment, and travel.
  • Healthcare costs – Medicare won’t cover everything, so budget for premiums, out-of-pocket expenses, and potential long-term care.

If there’s a gap between what you need and what you have, it’s better to spot it now while you still have time to adjust.

Have You Eliminated or Managed Debt?

Debt can be a serious drain on retirement savings, especially if you’re still carrying a mortgage, credit card balances, or personal loans. Ideally, you’ll enter retirement as debt-free as possible, but if that’s not realistic, the key is managing it wisely.

Prioritize high-interest debt first, as it eats into your savings faster. If you still have a mortgage, consider whether downsizing or refinancing makes sense. Even small changes—like paying off car loans early or consolidating debt for a lower interest rate—can make a big difference in how long your money lasts.

Do You Have a Plan for Healthcare Costs?

Healthcare is one of the biggest financial surprises for retirees. Even if you’re eligible for Medicare at 65, it doesn’t cover everything. You may still need:

  • A Medicare supplement plan (Medigap) or Medicare Advantage to cover out-of-pocket costs.
  • Long-term care insurance, which can protect you from the high costs of assisted living or nursing care.
  • A Health Savings Account (HSA) if you’re still working—it’s one of the best tax-advantaged ways to save for medical expenses in retirement.

It’s also smart to plan for unexpected health issues. A sudden diagnosis or injury can quickly derail retirement savings if you’re not prepared.

Will Your Income Keep Up With Inflation?

One mistake retirees make is underestimating the impact of inflation. The money you need today won’t stretch as far in 10 or 20 years. If you’re relying solely on savings, that purchasing power could shrink faster than expected.

A smart approach is to keep part of your portfolio in growth investments, like stocks or dividend-paying funds, even in retirement. Many retirees make the mistake of shifting everything to bonds or cash, which may not keep pace with inflation. Balance is key—your money needs to last, but it also needs to grow.

Do You Have a Tax Strategy?

Taxes don’t disappear when you retire, and without a plan, they can take a big bite out of your savings. Withdrawals from traditional 401(k)s and IRAs are taxed as ordinary income, while Social Security may also be taxable depending on your income level.

Consider these strategies to keep more of your money:

  • Withdraw from taxable accounts first – This lets tax-deferred accounts grow longer.
  • Use Roth IRAs – Qualified withdrawals are tax-free.
  • Convert some retirement savings to Roth accounts – Doing this before retiring can reduce taxes later.
  • Plan Required Minimum Distributions (RMDs) – Once you turn 73, the IRS requires you to start withdrawing from certain accounts, so plan ahead to avoid a big tax hit.

A financial planner can help you make the most of tax-efficient withdrawal strategies.

Is Your Estate Plan in Order?

Even if you think you’re covered, double-check that everything is legally in place. Estate planning isn’t just for the ultra-wealthy—it ensures your assets go where you want and helps prevent headaches for your loved ones.

Key things to review:

  • Your will – Make sure it’s updated and reflects your current wishes.
  • Beneficiary designations – Retirement accounts, life insurance policies, and even bank accounts need named beneficiaries.
  • A power of attorney and healthcare directive – These documents protect you if you become unable to make decisions.
  • Trusts – If you have complex assets, a trust can help minimize taxes and make asset distribution easier.

These details can make a big difference in ensuring your wealth is transferred smoothly and efficiently.

Do You Have a Backup Plan?

Even the best-laid plans can hit unexpected roadblocks. Markets fluctuate, emergencies happen, and retirement dreams sometimes change. A strong backup plan gives you peace of mind.

Think about:

  • Having at least 1-2 years’ worth of living expenses in easily accessible cash.
  • Keeping some part-time or freelance work options open if needed.
  • Building a flexible budget that can adjust if necessary.

Flexibility is key—you want to enjoy retirement without financial stress.

Feeling Ready? Double-Check These Final Steps

Before officially retiring, take a moment to run through everything:

  • Are your income sources stable and diversified?
  • Have you tested your retirement budget by living on it for a few months?
  • Is your investment strategy balanced between security and growth?
  • Do you have a solid healthcare and insurance plan?
  • Is your estate plan complete and up to date?

If you can confidently say yes, you’re in great shape for retirement. If not, there’s still time to fine-tune your plan and make adjustments. The goal isn’t just to retire—it’s to retire with confidence, knowing your future is secure.