2630 W. Bradley Place, Suite C Chicago, IL 60618
E-mail: pwa@keatinginc.com
Phone: 773-975-4020
Healthcare and Retirement Planning for the Costs You Can’t Predict

Healthcare and Retirement: Planning for the Costs You Can’t Predict

For many people approaching retirement, healthcare is the biggest unanswered question. You may feel confident about your savings and investments, yet uneasy about what medical costs might look like later in life.

That unease is justified. Healthcare expenses are one of the most common reasons retirement plans fall short—not because people ignore them entirely, but because they underestimate how much control early planning can provide.

Why Healthcare Feels So Uncertain

Unlike housing or daily living expenses, healthcare costs don’t follow a smooth path. They can remain manageable for years and then increase sharply due to one diagnosis, one injury, or one change in care needs.

Medicare provides an important foundation, but it does not eliminate risk. Premiums, deductibles, prescriptions, dental care, vision care, and long-term support services often come with significant out-of-pocket costs. For someone approaching retirement, these expenses may feel distant, but they become very real later on.

The mistake many pre-retirees make is assuming healthcare planning can wait until retirement begins. By then, options are often narrower and more expensive.

The Power of Planning Before Medicare Begins

The years leading up to retirement are the best time to make healthcare planning decisions calmly and strategically. This includes understanding how Medicare works, how supplemental coverage fits in, and how different choices affect long-term costs.

Health Savings Accounts, for those eligible, are especially valuable during this stage. When funded and invested properly, HSAs can become a dedicated healthcare reserve, providing tax-efficient support for medical expenses later in life. Too often, these accounts are used casually during working years instead of being preserved for retirement, when they are most powerful.

Planning ahead also allows you to model realistic healthcare costs rather than relying on averages that may not reflect your situation.

Long-Term Care: The Conversation Most People Avoid

Long-term care is one of the most emotionally difficult topics in retirement planning, which is why it’s often postponed. Yet avoiding the conversation doesn’t reduce the risk—it simply shifts the burden to future decisions made under stress.

Approaching retirement is the right time to explore options thoughtfully. Whether through insurance, hybrid solutions, or self-funding strategies, the key is intentionality. Even a partial plan can protect independence, reduce financial strain on family, and preserve more flexibility later in life.

Healthcare planning isn’t about predicting illness. It’s about ensuring that if care is needed, financial decisions don’t limit personal choices.

Call to Action: Take Control of the Unknown

Healthcare costs don’t have to be the wildcard in your retirement plan.

At Purposeful Wealth Advisors we help pre-retirees evaluate healthcare risks, integrate HSAs and Medicare planning, and prepare for long-term care in a way that aligns with personal values and financial realities.

Now is the time to plan—while you have options.
Schedule a pre-retirement healthcare planning session and gain clarity about one of retirement’s biggest uncertainties.

Clients may incur separate fees and expenses from custodians, insurance providers, or other third-party products referenced, which are independent of advisory fees charged by the firm.

Beth Kraszewski recipient of