Figuring out when to retire is one of the biggest decisions people make. Engaging with trusted professionals can help you make the best decision for your circumstances. To be sure you’re fully prepared, an aptly-titled article from Kiplinger recommends “The Six People You Need to Talk to Before Retiring—and the Best Questions to Ask.”

A financial planner will help clarify long-term wishes and goals. By working with a financial advisor early on, you’ll have someone to develop a plan for the lifestyle you want in retirement and understand how to get there. When you’re closer to retirement, they’ll help button down your plan and help you make realistic decisions.

An experienced estate planning attorney will ensure that your estate is prepared correctly and your legal affairs are in order, with protection in place if you become incapacitated and after you’ve passed. Even if you don’t expect to leave significant assets to heirs, your family will appreciate your having an estate plan so they aren’t faced with the stressful challenges and costly problems occurring when there is no will. The estate planning attorney will discuss whether you need a trust to protect assets and smoothly transfer assets to beneficiaries.

You’ll also want Power of Attorney and Health Care Proxy documents created specifically to your wishes. These documents allow a person you choose to take care of financial and health matters if you cannot speak on your own behalf. Talk with the estate planning attorney about ensuring that assets are distributed according to your wishes and minimizing estate taxes for heirs.

An insurance broker will help with risk management before and after retirement. They can help with the options for Medicare and health insurance coverage, which can be overwhelming once you leave an employer’s plan. Talk with an insurance agent about long-term care costs and what policies are available. You may need to purchase a hybrid life insurance plan to obtain long-term care insurance. However, long-term care costs are exorbitant, so you should have an LTC policy if possible.

Most people don’t know about working with a senior living advisor. However, they can be invaluable to enhancing the quality of your life in retirement. They help people identify a wide variety of tools and services. For instance, many new tech tools are making it safer for seniors to stay in their homes, local services through various agencies and longevity care options to explore.

Social Security advisors add another layer of knowledge to retirement planning. A Social Security advisor will help determine the best time to take benefits based on your financial situation. There’s more than your age to consider. Death of a spouse, divorce, chronic conditions and disability should be considered when deciding on the best time to take benefits.

Retirees need to have a CPA on their team as well. Balancing withdrawals from tax-advantaged accounts like IRAs or pensions, Social Security benefits, and withdrawals from investment accounts must be planned with taxes in mind. A CPA will help you create a plan for cash flow in retirement.

Americans don’t like to talk about death or money. However, when preparing for retirement, these subjects must be discussed to create a good plan. When you’ve identified your team, don’t hold back. The more information you share with them, the better they can help prepare for an enjoyable retirement.

Reference: Kiplinger (Feb. 27, 2025) “The Six People You Need to Talk to Before Retiring—and the Best Questions to Ask”