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Retirement isn’t a one-time event—it’s a multi-decade journey. And like any journey, you need to stop regularly to check the map and make sure you’re still on the right path. Scheduling a semi-annual or annual retirement checkup is one of the best ways to confirm your plan is working for you, not just on paper, but in real life.
Whether you retired five years ago or just recently stepped away from full-time work, your financial life continues to evolve. Markets shift. Tax laws change. Healthcare costs rise. Personal goals shift with age. Regularly reviewing your plan once or twice a year keeps you ahead of these changes so you can adjust early and avoid bigger problems later.
Why Annual or Semi-Annual Retirement Checkups Matter More Than Ever
A retirement checkup is more than a quick look at your account balances. It’s about understanding how real-world events—like inflation, market performance, and Required Minimum Distribution (RMD) rules—affect your ability to maintain the lifestyle you’ve worked so hard to build.
As you move through your 60s, 70s, and beyond, financial decisions carry more weight. Withdrawing too much during a down market can permanently shrink your savings. Failing to adjust for inflation or taxes can quietly erode your purchasing power. Annual or semi-annual checkups give you the chance to catch these issues early and make small course corrections before they grow into costly mistakes.
What’s Included in a Retirement Checkup?
A proper retirement checkup should cover every major part of your financial life—not just portfolio performance. Key areas to review include:
1. A Financial Reassessment of Spending and Income Sources
At the heart of every review is a reassessment of your spending patterns and income sources. Are you spending more or less than expected? Have healthcare or travel costs changed? Are you still drawing from the most tax-efficient accounts?
Looking at these questions once or twice a year can uncover blind spots. For instance, if your spending has dipped but markets have recovered, it might make sense to reduce withdrawals temporarily and let your investments continue growing.
2. Inflation and Cost-of-Living Adjustments
Inflation has hit retirees harder than most, especially in areas like healthcare, food, and insurance. An annual or semi-annual checkup helps you measure how inflation is affecting your real-world budget.
Small adjustments—such as updating your withdrawal strategy or slightly shifting your asset allocation—can help protect your income against rising costs, especially if you don’t have guaranteed income streams like pensions or annuities.
3. RMD Rule Changes and Tax Planning Updates
The rules for Required Minimum Distributions have changed in recent years and will likely continue to do so. A consistent review schedule ensures you’re taking the correct RMDs and doing so in the most tax-efficient way.
For example, if you’re approaching age 73, planning ahead can help you avoid unnecessary taxes. Strategies like Roth conversions, Qualified Charitable Distributions (QCDs), or changing the order of withdrawals can all be part of your annual or semi-annual review.
The Power of Sticking to a Yearly Review Schedule
A once-a-year or semi-annual checkup gives you a natural opportunity to realign your plan. It’s also an ideal time to revisit estate documents, beneficiary designations, and healthcare directives. Even if your personal life hasn’t changed, laws and markets may have shifted underneath you.
A 2025 study from the Financial Times found that retirees who conducted regular financial reviews were far more likely to sustain their income for 25-plus years—especially during periods of rising healthcare costs and inflation.
More importantly, regular checkups bring peace of mind. Knowing that your plan has been reviewed and updated removes the emotional guesswork from your financial decisions.
Real-Life Example: How One Couple Stayed on Track with Annual Checkups
Karen and David retired at 65 with $3.2 million in savings. They followed a 4 percent withdrawal plan, but after five years, inflation had jumped, and their travel and healthcare costs were higher than expected.
During their annual retirement checkup, their advisor noticed they were withdrawing slightly more than planned, partly due to rising insurance premiums and generous gifts to their grandchildren.
By reassessing their plan, the advisor helped them:
- Reduce unnecessary portfolio risk
- Switch the order of withdrawals to lower taxes
- Set up a flexible withdrawal range based on market performance
- Adjust their gifting strategy to be more tax-efficient
The result? They stayed on track without feeling restricted. Annual reviews gave them clarity, control, and confidence that their money would last.
What Happens If You Skip Regular Retirement Reviews?
Without annual or semi-annual reviews, small missteps can compound for years. Common risks include:
- Overspending during market downturns can drain your savings faster than expected
- Ignoring updated tax laws, leading to higher RMD taxes or Medicare premium surcharges
- Missing opportunities for Roth conversions or charitable giving strategies
- Falling behind inflation, especially with fixed-income or low-growth portfolios
The danger isn’t one bad year—it’s the slow buildup of uncorrected mistakes over time.
How a Fiduciary Advisor Helps Keep You on Track Year After Year
You don’t have to manage every moving part yourself. Most retirees prefer to delegate this process to a fiduciary advisor who can review all the pieces—investments, taxes, estate plans, healthcare, and income strategy—and make sure they fit together.
At Haywood Wealth Management, our retirement reviews include:
- A detailed reassessment of income, spending, and taxes
- Ongoing inflation and cost-of-living impact analysis
- Updated withdrawal strategies
- Tax planning ahead of RMD milestones
- Portfolio rebalancing and risk adjustment
We also coordinate with your CPA, estate attorney, or insurance specialist when needed. It’s a team-based approach designed to protect your income, minimize taxes, and keep your plan aligned as life changes.
When to Schedule Your Retirement Checkups
If it’s been more than a year since your last review, schedule one now. Even if things feel steady, a quiet drift off course can happen easily in retirement. And the sooner it’s spotted, the easier it is to fix.
The best times to schedule a retirement checkup include:
- Annually, around the same time each year (or every six months for complex portfolios)
- After major market volatility or inflation spikes
- Before turning 73 to plan for RMDs
- After a significant life event like downsizing, a family inheritance, or health changes
Think of it like a routine physical for your finances. It’s not about fixing big problems—it’s about keeping your plan strong, sustainable, and aligned with your goals.
Ready to Review Your Retirement Plan?
An annual retirement checkup isn’t about drastic changes. It’s about staying proactive and fine-tuning as life evolves. Meeting once or twice a year keeps your plan working for you—so your money continues to support the life you want, year after year.
At Haywood Wealth Management, we specialize in retirement income planning for high-net-worth families and individuals. Every plan is customized to your goals, values, and changing needs—not a one-size-fits-all model.
Let’s make sure your next chapter is just as well-planned as the first.
👉 Schedule Your Retirement Pathfinder Analysis to get expert guidance and a plan designed to support the life you’ve worked so hard to create.
Your legacy matters. Let’s make sure it’s protected, personalized, and built to last.
