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What Issues Should I Consider Before I Retire?

Updated: Jun 5, 2023

This checklist covers 32 of the most important planning issues to identify and consider for a client who is about to retire. It’s structured as follows:

  • Cash Flow Issues

  • Health Insurance Issues

  • Asset & Debt Issues

  • Tax Planning Issues

  • Long-Term Planning Issues

  • Other Issues

Planning for retirement involves careful consideration of various aspects, from financial matters to healthcare and estate planning. In this article, we'll walk you through a comprehensive retirement planning checklist covering 32 important issues to identify before you retire. By addressing these areas, you can achieve a well-rounded plan that ensures financial security and peace of mind during your golden years.

  1. Cash Flow Issues: Evaluate how your cash flow needs will change upon retirement and develop a new income and expense plan. Consider factors such as pension options, Social Security benefits, employer benefits, and access to penalty-free 401(k) withdrawals.

  2. Health Insurance Issues: Understand the eligibility age for Medicare and explore exemptions or premium assistance tax credits if you're enrolled in the health insurance marketplace. Determine whether you need to change your employer-sponsored health insurance upon turning 65 and assess the need for additional coverage like vision, dental, or long-term care insurance.

  3. Asset and Debt Issues: Review your assets and debt situation, including stock options, annuities, illiquid assets, and loans from employer retirement plans. Determine your risk tolerance and the need for an exit strategy or succession plan if you're a business owner.

  4. Tax Planning: Consider strategies to optimize tax efficiency, such as Roth conversions to reduce required minimum distributions (RMDs) and deferring conversions until you're in a lower tax bracket. Understand estate tax implications if your estate may exceed the federal gift tax exclusion amount. Evaluate charitable giving strategies and update your estate plan and account beneficiaries as necessary.

  5. Long-Term Planning: Assess the need for long-term care insurance or self-insurance strategies. Review unused vacation days and explore state-specific considerations that may impact your retirement plan. Stay open to adapting your plan as circumstances change.

Retirement planning involves meticulous attention to detail across various domains, ranging from financial considerations to healthcare and estate planning. By following this comprehensive checklist, you can ensure that you've covered crucial aspects of retirement preparation. Remember, working with a qualified financial planner can provide valuable guidance and expertise to help you navigate the complexities of retirement planning effectively. Start early, stay informed, and embrace the possibilities that retirement brings for a fulfilling and financially secure future.

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