In my experience, the years leading up to 60 are often one of the most important financial planning periods in a person’s life.
For many professionals, earnings are near their peak, retirement becomes more visible on the horizon, and financial complexity tends to increase all at once. Taxes, investments, retirement income planning, insurance, estate planning, and family considerations begin interacting more directly during this stage.
The decisions made in this window can have a meaningful long-term impact, which is why it can be helpful to periodically step back and revisit a few foundational questions.
1. What Is Your Retirement Income Goal — and Are You On Track?
Many people focus primarily on account balances rather than the actual income those assets may eventually need to generate.
A more comprehensive retirement analysis typically looks at projected spending needs, inflation, Social Security timing, pensions where applicable, taxes, healthcare costs, and how different accounts may be used over time.
The important question is not simply whether retirement accounts are growing. It is whether the overall plan supports the lifestyle and flexibility you hope to maintain.
2. What Happens if Markets Don’t Cooperate With Your Retirement Timing?
Annual One of the biggest risks approaching retirement is not necessarily long-term market performance, but poor market conditions occurring near the beginning of retirement withdrawals.
This is where income planning, cash reserves, portfolio structure, and withdrawal flexibility become especially important.
A thoughtful retirement plan should consider how the strategy may adapt during periods of market volatility rather than assuming markets will cooperate perfectly with the retirement timeline.
3. Are You Saving Beyond the 401(k)?
Maximizing a 401(k) is an important foundation, but for many high earners, contribution limits alone may not fully support long-term retirement goals.
As income rises, retirement planning often expands into taxable investment accounts, Roth strategies, deferred compensation plans, health savings accounts, and broader tax-efficient income planning.
The question is less about whether the 401(k) is maxed out and more about whether total savings and investment strategy are aligned with future goals.
4. When Did You Last Review Beneficiary Designations?
Retirement accounts and life insurance policies transfer according to beneficiary forms on file, not necessarily according to a will or trust.
Over time, beneficiary designations can become outdated as family structures, relationships, and intentions evolve.
This is one of the simplest planning reviews people can do, yet one of the most commonly overlooked.
5. Do You Have a Multi-Year Tax Strategy?
Many people think about taxes only during filing season. In reality, some of the most meaningful planning opportunities happen throughout the year and across multiple years.
For higher earners, this can include charitable giving strategies, Roth conversion analysis, investment tax management, retirement contribution decisions, and planning around future required minimum distributions.
Looking at taxes over a longer horizon often creates opportunities that are easy to miss when viewed one year at a time.
6. Is Your Insurance Coverage Still Appropriate?
Insurance needs often change significantly during peak earning years.
Coverage that once felt appropriate may no longer reflect current income, family responsibilities, debt levels, or long-term goals. This applies not only to life insurance, but also disability coverage, liability protection, and long-term care considerations.
Periodic reviews can help ensure coverage evolves alongside the rest of the financial plan.
7. Does Your Estate Plan Still Reflect Your Wishes and Current Situation?
Estate plans are rarely “set once and forget forever” documents.
Changes in family structure, asset levels, business ownership, or long-term intentions can all affect whether existing documents still accomplish what they were originally designed to do.
It is also important that estate documents, beneficiary designations, and account structures are coordinated together rather than reviewed independently.
Final Thoughts
None of these questions require a crisis to become relevant. More often, they simply reflect the reality that financial planning tends to become more valuable as life, family, and finances grow more complex over time.
A thoughtful financial plan is less about predicting the future perfectly and more about building flexibility, coordination, and clarity around the decisions that matter most.
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Bill McDonald, CFP®
Partner, Senior Wealth Manager | Tidewater Wealth Management