Bridging the Gap Between Work and Retirement: Financial Planning for the Transition Years

Learn how financial planning for the transition years can help balance income, lifestyle, and healthcare as you move toward retirement.

For many people, retirement is not a single event but a gradual process. This makes financial planning for the transition years an important step in preparing for the future. The years between full-time work and full retirement often include part-time employment, lifestyle adjustments, and evolving income sources. Taking time to plan can make these years more manageable.

Understanding Income Sources During the Transition

As you reduce or stop working, income may come from a mix of sources. Some individuals continue part-time work or consulting, while others begin drawing from pensions or Social Security. In certain cases, retirement account withdrawals may also start during this period.

Coordinating these sources can help create stability. For example, delaying Social Security may provide larger monthly benefits later, but it may also mean using other income sources in the short term. Evaluating your options can help you decide what fits best for your situation.

Considering Lifestyle Adjustments

Lifestyle choices often shift during the transition years. With more free time, you may want to travel, explore new hobbies, or spend additional time with family. These activities can affect your budget. At the same time, reduced work hours may lower commuting or professional expenses.

Creating a spending plan that reflects both the reduction in income and the increase in discretionary activities can help you balance resources with priorities. Reviewing housing costs and healthcare needs is also valuable during this stage.

Preparing for Healthcare Changes

Healthcare is a major consideration when bridging the gap between work and retirement. If you retire before Medicare eligibility begins, you may need to plan for private insurance or marketplace coverage. For those reaching age 65, decisions about Medicare Supplement and Advantage plans become important.

Evaluating costs and coverage now can help you avoid gaps in insurance and prepare for long-term needs. Including these expenses in your retirement budget supports a clearer view of your financial picture.

Managing Taxes During the Transition

The shift from earned income to retirement income changes your tax situation. Withdrawals from tax-deferred accounts such as traditional IRAs or 401(k)s are generally taxable, while Roth accounts may offer tax-free income. Social Security benefits may also be taxable depending on total income.

Strategic planning can help balance these factors. Some retirees consider partial Roth conversions during the transition years, which may reduce future Required Minimum Distributions and diversify tax treatment across accounts.

Reviewing Investments and Risk

During the transition years, your investment strategy should reflect both ongoing growth goals and the need for stability. Maintaining diversification across asset classes can help spread risk. While past performance is not indicative of future results, reviewing your portfolio’s allocations can help align it with your income needs and time horizon.

This is also a good stage to revisit your tolerance for market volatility. As withdrawals begin, market swings may affect both income and portfolio longevity. Adjusting allocations can help reduce potential strain.

Considering Estate and Legacy Planning

As you move closer to full retirement, estate planning becomes more relevant. Reviewing wills, trusts, and beneficiary designations ensures your intentions are clearly documented. Some choose to incorporate charitable giving or family support into their planning at this stage.

Legacy planning reflects not just financial numbers but also personal values, making it a key part of overall retirement preparation.

Building Flexibility Into Your Plan

The transition years bring change, and flexibility is essential. Health, markets, and family needs may shift over time. By reviewing your financial plan regularly, you can adjust gradually instead of making large, unexpected changes later.

Preparing for a New Life Stage

Financial planning for the transition years helps create a bridge between your working life and full retirement. By reviewing income, lifestyle, healthcare, taxes, investments, and estate matters, you can enter retirement with greater clarity.

At Milford Financial, we support clients in creating strategies that reflect both today’s needs and tomorrow’s possibilities. Contact our team today to schedule a conversation about your transition into retirement.

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Past performance is not indicative of future results. The material above has been provided for informational purposes only and is not intended as legal or investment advice or a recommendation of any particular security or strategy. The investment strategy and themes discussed herein may be unsuitable for investors depending on their specific investment objectives and financial situation. Information obtained from third-party sources is believed to be reliable though its accuracy is not guaranteed, and Milford Financial makes no representation or warranty as to the accuracy or completeness of the information, which should not be used as the basis of any investment decision. Information contained on third party websites that Milford Financial may link to are not reviewed in their entirety for accuracy and Milford Financial assumes no liability for the information contained on these websites. Opinions expressed in this commentary reflect subjective judgments of the author based on conditions at the time of writing and are subject to change without notice. No part of this material may be reproduced in any form, or referred to in any other publication, without express written permission from Milford Financial.

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