The last five years before retirement are some of the most important in your financial life. This is the window when your portfolio may be near its peak, your income strategy starts to take shape, and the margin for error begins to narrow.

For many families, retirement is not just about leaving work. It’s about replacing a paycheck, managing taxes more carefully, planning for healthcare costs, and making sure your wealth continues to support the life you want to live. Thoughtful decisions now can make the transition smoother and give you more flexibility later.

At Astra, we help clients prepare for retirement as a full wealth transition. That means looking at investments, income, taxes, healthcare, estate planning, and family priorities as one connected plan.

Start With the Full Picture

Before making adjustments, take stock of where you are today and what retirement will need to support. That means more than reviewing account balances. It means understanding how your assets, cash flow, and goals fit together.

Start by identifying the income sources you expect to rely on in retirement, such as Social Security, pension payments, retirement account withdrawals, taxable investment income, annuities, or income from a business or real estate. Then compare those resources to the lifestyle you want to maintain, including travel, family support, philanthropy, second homes, healthcare, and the pace of spending you expect in the early years of retirement.

This is also the right time to pressure-test the plan. Would it still work if markets decline shortly before you retire? What if healthcare costs rise faster than expected? What if you decide to retire earlier than planned, or continue working in a reduced capacity? The goal is not to predict every outcome. It is to make sure your plan can hold up across a range of realistic scenarios.

Shift From Building Wealth to Turning It Into Income

As retirement gets closer, the conversation should start to change. For years, the focus may have been on growth and accumulation. In the final stretch, the focus should expand to include income design, downside protection, liquidity, and withdrawal planning.

That usually means reviewing whether your portfolio is positioned for the next phase of life. A strong pre-retirement plan should account for the order in which assets may be withdrawn, how much cash or short-term reserves to keep on hand, and how to reduce the risk of having to sell investments at the wrong time. For affluent households, this also may include planning around concentrated stock positions, deferred compensation, private investments, or the sale of a business.

Social Security decisions also matter here. Claiming at the wrong time can affect lifetime income, especially for married couples. The right strategy depends on your overall balance sheet, your other sources of income, your longevity assumptions, and whether survivor income is part of the plan.

Use the Final Years to Max Out Savings Opportunities

The years just before retirement are often your last opportunity to build assets in tax-advantaged accounts while you still have earned income. In 2026, the employee contribution limit for 401(k), 403(b), and similar workplace plans is $24,500. If you are age 50 or older, you can generally contribute an additional $8,000. If you are ages 60 through 63, a higher catch-up contribution of $11,250 may apply. For IRAs, the 2026 total contribution limit is $7,500, or $8,600 if you are age 50 or older.

If you are eligible for a Health Savings Account, that can also be an effective planning tool in the final working years. HSAs offer a rare triple tax benefit. Contributions may be deductible, growth can be tax-free, and withdrawals for qualified medical expenses are also tax-free. For clients preparing for retirement healthcare costs, that flexibility can be valuable.

Get Ahead of Taxes Before Retirement Starts

Taxes often become more important, not less, as retirement approaches. Many investors have built wealth across multiple account types over time, including taxable brokerage accounts, tax-deferred retirement accounts, and Roth assets. The way you draw from each of those buckets can have a meaningful effect on how much income you keep.

This is where planning ahead matters. In the years before retirement, it may make sense to explore Roth conversions, realize capital gains strategically, or begin shaping a withdrawal plan that avoids unnecessary tax spikes later. Coordinated withdrawals can also help manage bracket exposure over time, rather than leaving those decisions to chance from year to year.

Required minimum distributions should also be part of the conversation. Under current rules, many retirement account owners must begin taking RMDs at age 73, with the starting age rising to 75 for some younger retirees under SECURE 2.0. If those future withdrawals are likely to be large, it may make sense to plan around them before they begin.

For high-net-worth families, tax planning may go well beyond retirement accounts. It may include managing concentrated stock, deciding when to sell a business, coordinating charitable gifts, or reviewing how future distributions may affect heirs. Retirement is often when these decisions start to intersect, and they are best handled as part of one strategy.

Make Healthcare Part of the Plan

Healthcare is one of the largest expenses many retirees face, and it deserves more than a quick estimate. Medicare can help, but it does not eliminate premiums, deductibles, out-of-pocket costs, prescription expenses, or the possibility of long-term care needs.

In 2026, the standard Medicare Part B premium is $202.90 per month, and higher-income retirees may pay more based on income through IRMAA adjustments. That makes healthcare planning especially important for affluent households whose income may vary year to year due to Roth conversions, capital gains, or business events.

As retirement approaches, it is important to understand enrollment timing, estimate future healthcare costs realistically, and decide how those costs will be funded. A strong plan should also address the role of long-term care, whether through self-funding, insurance, or a combination of both.

Review Estate Planning and Family Priorities

Retirement planning is not only about income and investments. It is also a natural time to review how your broader wealth plan supports the people and priorities that matter most.

That may include updating wills, trusts, powers of attorney, healthcare directives, and beneficiary designations. It may also mean reviewing how assets are titled, whether your estate plan still reflects your intentions, and how wealth will be transferred across generations. For some families, this is also the right time to discuss gifting strategies, charitable giving, or how adult children may fit into long-term planning conversations.

These details are easy to postpone during working years. They become more important as retirement gets closer.

The Astra Approach

Retirement should not feel like a series of disconnected financial decisions. It should feel like a plan.

At Astra, we help clients bring the full picture together. We look at portfolio strategy, income planning, taxes, healthcare, estate considerations, and family goals in one place, with advice that is personal, practical, and built around your life. Our role is to simplify complexity, stay ahead of the details, and help you move into retirement with confidence.

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