What Golf Teaches About Managing the Next Stage of Your Financial Life
โSuccess depends almost entirely on how effectively you manage the gameโs two ultimate adversaries: the course and yourself.โ
โ Jack Nicklaus
While Nicklaus was talking about golf, his point applies well to retirement planning. The front nine of your financial life was about saving, investing, and building wealth. As you make the turn toward retirement, the focus shifts from accumulating assets to using them to support the life you want.
Life and golf share the same truth: neither one unfolds exactly as planned. The key is developing a strategy with enough flexibility to spot opportunities, avoid hazards, and adjust to a few unexpected bounces along the way.
This guide outlines several areas to review as retirement approaches, including savings, healthcare, Social Security, taxes, retirement income, estate planning, and flexibility for the unexpected.
Know Your Yardage: Assessing Retirement Readiness
Before choosing a club, a golfer needs to know the distance to the target and the conditions affecting the shot. Retirement planning begins with a similar discipline: establishing a clear picture of where you are today and where you want to go.
Begin by taking an inventory of your financial life. Review your assets, liabilities, income sources, savings rate, spending habits, and expected retirement expenses. If you carry high-interest debt, consider directing excess cash to pay it down while your employment income is still steady.
Then define what retirement looks like to you. When do you want to retire? What will you spend? Which expenses are essential, and which are discretionary? Do you have any travel, charitable, family support, or legacy goals?
These answers matter because thereโs no universal definition of โenough.โ What you need to retire successfully depends on the lifestyle you want, the income your portfolio must produce, and the risks your plan may need to withstand.
From there, evaluate whether your investment strategy still aligns with your goals, time horizon, and expected income needs. Review your asset allocation, spending assumptions, and withdrawal needs. The portfolio that built wealth during your working years might not be the one best suited to support withdrawals.
Finally, revisit your estate plan. Retirement often coincides with changing family dynamics, charitable goals, and legacy considerations. Estate planning is about more than asset distribution at death; it can also help ensure the right people are able to make financial, legal, and healthcare decisions if youโre unable to.
Retirement Readiness Checklist:
- Understand your current financial position
- Define your retirement goals and desired lifestyle
- Estimate future expenses, income sources, and gaps
- Review asset allocation and risk tolerance
- Review your estate plan and beneficiary designations
Understanding the Rules of the Game
Golf isnโt about hitting the ball as far as possible; itโs about completing the round as effectively as possible. That requires more than just a good swing. You must know the rules, recognize opportunities, and understand how one decision affects the rest of the round. Retirement comes with its own set of rules, deadlines, and tradeoffs. Contribution limits, healthcare coverage, Social Security, Medicare, required distributions, and taxes all shape the decisions you make before and during retirement.
Maximizing Retirement Savings
The years leading up to retirement are often peak earning years, providing an opportunity to strengthen your balance sheet and accelerate retirement savings.
In 2026, individuals can contribute up to $7,500 to a traditional IRA or Roth IRA. Most workplace retirement plans, including 401(k)s, 403(b)s, governmental 457 plans, and the Thrift Savings Plan, allow contributions of up to $24,500, while SIMPLE plans allow contributions of $17,000.
Individuals aged 50 or older can also take advantage of catch-up contributions. The IRA catch-up contribution is $1,100 in 2026. For many workplace plans, individuals ages 50-59 or 64 or older can contribute an additional $8,000. For SIMPLE plans, the catch-up contribution is $4,000. Individuals ages 60-63 may qualify for an enhanced catch-up contribution of $11,250, or $5,250 for SIMPLE plans.
Beginning in 2026, employees whose prior-year wages exceeded the IRS threshold for high-income earners must make catch-up contributions on a Roth basis if their retirement plan offers Roth contributions. That means taxes are paid in the year contributions are made in exchange for potential tax-free withdrawals in the future.
Saving more is often beneficial, but where you save can matter just as much as how much you save.
Contributing enough to receive your full employer match is generally a good starting point. Beyond that, review your overall balance sheet; if a significant portion of your wealth is already concentrated in pre-tax accounts, it may be worth evaluating whether additional savings should be directed toward other accounts.
Roth assets can be particularly valuable, but timing matters: large Roth contributions or conversions may be less attractive when income is at its highest. For many people, the window between retirement and the start of Social Security or Required Minimum Distributions (RMDs) may offer a planning opportunity for Roth conversions, when taxable income is temporarily lower.
Planning for Healthcare
Healthcare is one of the largest expenses retirees face, so advance planning is essential.
If you expect to retire before age 65, one of the first questions should be how you’ll maintain health insurance coverage until Medicare eligibility begins. Potential options include:
- COBRA coverage
- Affordable Care Act (ACA) marketplace plans
- Retiree health benefits offered through your employer
- Coverage through a working spouseโs employer plan
Once eligible for Medicare, understanding enrollment deadlines and coverage options is critical; missing certain enrollment windows can result in late enrollment penalties that may continue for as long as you have Medicare coverage.
Medicare is divided into four parts:
- Part A: Hospital insurance
- Part B: Physician and outpatient services
- Part C (Medicare Advantage): A private plan option for receiving Medicare-covered benefits
- Part D: Prescription drug coverage
Many retirees ultimately choose between enrolling in a Medicare Advantage Plan or supplementing Medicare with a Medigap policy and Part D prescription coverage.
If you’re eligible to contribute to a Health Savings Account (HSA), it can be one of the most powerful tools available for covering future healthcare expenses. In 2026, contribution limits are $4,400 for individual coverage and $8,750 for family coverage, with an additional $1,000 catch-up contribution available beginning at age 55. HSAs offer potential tax advantages on contributions, growth, and qualified medical withdrawals, making them a uniquely flexible resource for healthcare planning.
Coordinating Social Security
Social Security is one of the few sources of guaranteed lifetime income available to most retirees.
Benefits can begin as early as age 62 but claiming before your Full Retirement Age (FRA) results in a permanently reduced monthly benefit. For individuals born in 1960 or later, FRA is 67. Delaying benefits beyond FRA increases your benefit until age 70, when delayed retirement credits stop accruing.
The best strategy for claiming isnโt necessarily the one with the largest monthly benefit. Itโs the one that fits your overall retirement income plan. Consider retirement timing, life expectancy, marital status, other income sources, taxes, and spending needs before deciding when to claim.
If you haven’t reviewed your estimated benefits recently, create a my Social Security account at ssa.gov. Your statement includes benefit estimates at different age milestones and is a useful starting point when evaluating retirement income needs.
Understanding Future Distribution Rules
Pre-tax retirement accounts are generally subject to Required Minimum Distributions (RMDs) beginning at a certain age based on the current IRS rules. Those distributions can increase taxable income, affect Medicare premiums, and potentially cause a larger portion of Social Security income to become taxable.ย
Retirement Rules Checklist:
- Maximize employer matching and evaluate catch-up contributions
- Determine the optimal account to direct extra savings
- Identify potential Roth conversion opportunities
- Develop a plan for healthcare coverage before and during Medicare
- Understand Medicare enrollment deadlines and projected healthcare costs
- Review your Social Security benefit estimate and evaluate claiming options
- Understand how Social Security, Medicare, taxes, and retirement withdrawals interact
Carrying a Complete Set: Building Flexibility Throughout Retirement
Golfers don’t carry a variety of clubs in their bags because they expect to use all of them on every hole. Different situations call for different tools. A driver may be perfect off the tee, but it’s useless in a greenside bunker.
Retirement planning benefits from the same flexible approach. The more options you have to generate income, manage taxes, access liquidity, and adapt to changing circumstances, the easier it can become to navigate the unexpected.
Build Multiple Tax Buckets
One way to create that flexibility is to hold assets across different types of accounts with different tax treatments.
Cash reserves provide liquidity for emergencies and near-term spending needs. Taxable brokerage accounts can provide access to funds before age 59ยฝ for early retirees and offer flexibility when managing taxable income on an ongoing basis. Traditional retirement accounts provide tax-deferred growth but generally create taxable income when funds are withdrawn. Roth accounts can provide tax-free qualified income later in retirement. Each tax bucket serves a different purpose.
No one knows what tax rates, healthcare costs, market conditions, or spending needs will look like in the future. Assets spread across multiple tax buckets may provide more options when conditions change.
Plan for the Unexpected
Most plans account for the fairway shots: housing, travel, hobbies, and everyday living expenses. Fewer plans account as carefully for the rough.
Long-term care needs, the loss of a loved one, market downturns, or higher-than-expected inflation can all send a well-planned round off course. These risks canโt be eliminated, but a thoughtful plan can account for them, building in enough margin so one stray shot doesnโt derail the round.
Retirement Flexibility Checklist:
- Build assets across multiple tax โbucketsโ
- Maintain adequate liquidity in cash accounts
- Develop flexible income & portfolio withdrawal strategies
- Plan for early retirement access
- Prepare for unexpected risks and expenses
Avoiding Penalty Strokes
A great shot can quickly be undone by a handful of penalty strokes. In our article, 5 Retirement Mistakes That Could Cost You Thousands, we explore several common pitfalls retirees face. Social Security, Medicare premiums, taxes, and portfolio withdrawals are interconnected. Overlooking the interaction between them can create consequences that compound over time.
Coordinate Guaranteed Sources of Income
When you claim Social Security can meaningfully impact lifetime income. Delaying benefits beyond full retirement age can increase your eventual monthly benefit until age 70, which can be especially valuable for someone with a longer life expectancy or a desire for more guaranteed income later in life.
But receiving the maximum benefit isnโt automatically the right answer. The broader question is how much of your spending need can be covered by guaranteed income sources and how much must come from your portfolio to pay the bills.
When deciding when to begin collecting, also weigh your other income sources, portfolio withdrawals, health and longevity expectations, and, for married couples, the potential income needs of the surviving spouse.
Pension elections, if available, call for a similar approach. A single-life option may provide more income while youโre living, while a joint-and-survivor option provides continued income to a spouse after death.
Medicare and IRMAA
Medicare premiums are income-dependent. Part B and Part D premiums may increase through the Income-Related Monthly Adjustment Amount (IRMAA), which is generally based on modified adjusted gross income reported on your tax return from two years earlier. As a result, large capital gains, Roth conversions, or retirement account withdrawals can affect more than just your tax bill; they may also affect future Medicare premium costs.
For 2026, the standard Medicare Part B premium is $202.90 per month. Part B IRMAA surcharges range from $81.20 to $487.00 per month. For Part D, the national base beneficiary premium is $38.99 per month, while actual plan premiums vary. Additional IRMAA surcharges range from $14.50 to $91 per month.
Taxes and RMDs
Large balances in pre-tax retirement accounts can eventually lead to significant Required Minimum Distributions (RMDs), creating taxable income whether you need the distribution or not. Failure to take the required amount each year may result in a 25% excise tax on the amount not distributed, or 10% if corrected within 2 years. That doesn’t mean everyone should aggressively convert pre-tax retirement assets to Roth accounts. Converting too much in any single year could result in higher taxable income, create an unexpectedly large tax bill, and potentially increase Medicare premiums in a future year. Instead, the years between retirement and the start of RMDs may present a period of temporarily lower taxable income when Roth conversions are worth evaluating.
Retirement Pitfalls Checklist:
- Evaluate Social Security timing based on lifetime income needs, longevity, and survivor considerations
- Compare pension options based on current income and survivor protection
- Identify potential IRMAA exposure before making large income-generating decisions
- Project future RMDs and their potential impact on taxes and Medicare premiums
- Evaluate Roth conversions across multiple tax years
The Value of Professional Advice
A good caddie does more than carry the bag. They know the course and understand the golfer.
They know when a pin is worth going after and when itโs better to aim for the middle of the green. They recognize hazards that may not be obvious, anticipate how conditions could affect the next shot, and place each decision within the context of the entire round. Thatโs a useful way to think about retirement planning advice.
The challenge in retirement planning is rarely a lack of information. There is no shortage of calculators, articles, projections, and opinions about the โrightโ strategy. The harder part is determining which decisions make sense for you and how those decisions affect one another.
A financial advisor can help bring those decisions together within the context of your goals, family, and resources. After all, retirement isnโt about hitting one perfect shot; itโs about managing the entire course.
If youโre approaching retirement, a CERTIFIED FINANCIAL PLANNERยฎ professional can evaluate your retirement readiness and develop a strategy tailored to the life youโve worked hard to build.
