How to Retire: The Ultimate Checklist for a Confident Plan

This article was published in the March 2025 issue of the Traverse City Business News, and can be read in its entirety below. Black Walnut Wealth Management contributes articles and is featured in various media outlets.

Retiring successfully means more than just stepping away from work—it’s about creating the lifestyle and legacy you envision for the next chapter of your life. For affluent families and high-net-worth individuals, retirement planning requires an extra step of careful strategy, tax-conscious moves, and thoughtful financial stewardship. Here’s your comprehensive checklist to help set your retirement up for success.

1. Create a Lifestyle Plan

Retirement isn’t just about the numbers; it’s about clarifying and mapping out how you want to spend your time. As someone with significant assets, your financial means often allow the pursuit of passions, extensive travel, and engaging in philanthropy, but it’s essential to be intentional about your lifestyle goals.

Start by setting personal goals: What do you want your retirement to look like? Consider your desires around travel, hobbies, volunteer work, and time spent with family. Also, plan for the transition itself, as many individuals struggle with the identity shift that comes when stepping away from a career. Working with a coach or mentor can be helpful in navigating this change. Staying engaged is equally important—maintaining social connections and having a sense of purpose can significantly enhance your overall satisfaction in retirement.

2. Develop a Tax-Efficient Withdrawal Strategy

As you craft your retirement plan, managing taxes is just as important as managing investments. Tax efficiency is even more vital in retirement, as the way and timing of your withdrawals can leave a big impact on your tax bill.

It’s important to review your retirement accounts and understand the tax implications of withdrawing from various sources, such as IRAs, 401(k)s, and taxable brokerage accounts. In retirement, drawing from these accounts strategically can help reduce taxes. Consider Roth conversions as well—converting traditional IRAs to Roth IRAs before or early in retirement can reduce taxes on required minimum distributions (RMDs) later on.

3. Prepare for Healthcare and Long-Term Care

Data confirms that high-net-worth individuals often enjoy longer lifespans, which also means more years of potential healthcare expenses. One option to consider is long-term care insurance. Even if you are self-insured and have enough personal savings and investments to cover potential medical costs, long-term care coverage can shield your assets while offering comfort knowing you will be cared for in your later years.

It’s also important to review Medicare options, as Medicare doesn’t cover all healthcare needs; supplemental plans can help fill in the gaps. If you prefer premium care, you should factor in the costs of concierge medical services or high-quality long-term care facilities. To confirm you have the right coverage, discuss healthcare and long-term care options with your advisor, who can help tailor a plan that meets your specific needs.

4. Plan for Legacy and Estate Needs

Estate planning is a critical component of any retirement plan to distribute your wealth according to your wishes, and for affluent individuals, it goes beyond just having a will. A comprehensive estate plan includes trusts, gifting strategies, and a tax-conscious legacy plan.

It’s wise to regularly update your beneficiaries and estate documents to reflect any life changes and current wishes. Trusts can be particularly useful for managing assets, reducing estate taxes, and aligning your wealth with your intentions.

5. Establish a Charitable Giving Strategy

If charitable giving is part of your retirement vision, now is an ideal time to plan for it in a way that’s both meaningful and tax-efficient. Donor-advised funds, charitable remainder trusts, and outright gifts are all strategies that can help increase your impact.

Donor-advised funds allow you to make a charitable contribution, receive an immediate tax deduction, and distribute funds to charities over time. Charitable remainder trusts can provide income for you or your beneficiaries, with the remainder going to charity after a set period. Additionally, annual gifting to family or charities can be a valuable part of your financial plan and estate strategy.

Start With a Plan

Partnering with experienced advisors before and during retirement allows you to make well-informed decisions that can greatly influence your financial well-being. Begin by consulting a fee-only CERTIFIED FINANCIAL PLANNER® professional, an advisor who is held to a fiduciary standard. A reliable professional, focused on your best interests, can help prepare your family for the many rewarding experiences that come with retirement.

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