Your Retirement Planning Workbook: A Step-by-Step Checklist for Wisconsin Families
A retirement planning workbook turns a big, vague goal into a series of questions you can actually answer. Instead of wondering whether you have "enough," you write down what you spend, what income you can count on, what your investments may need to provide, and how taxes fit into each piece. The exercise often surfaces decisions that are easy to miss until a few years before retirement, when options are narrower.
Use the steps below as a retirement planning checklist. Work through them on paper or in a spreadsheet, then bring your answers to a planning conversation.
Start Here: A Complimentary Retirement Wealth and Tax Review
Once your workbook is filled in, the next step is testing it. Compound offers a complimentary, no-obligation wealth and tax review for people approaching or in retirement. It may include:
Income projections: Social Security, pensions, and portfolio withdrawals
Withdrawal order: which accounts to draw from first, and why taxes matter
Roth conversion considerations: whether lower-income years may create an opportunity
Investment allocation: whether your portfolio matches your timeline and spending needs
Request your retirement review.
Retirement Planning Workbook Step 1: Define What Retirement Looks Like
Write down when you would like to stop working full time, whether you plan part-time work or consulting, and where you plan to live. Note any big goals: travel, a lake home up north, helping children or grandchildren, or charitable giving. These choices drive every number that follows.
Step 2: Estimate Your Spending
Start with your current spending and adjust it. Some costs may fall, such as commuting and retirement contributions. Others may rise, such as travel and healthcare. Separate essential expenses (housing, food, insurance, taxes) from discretionary ones. This split helps later, because essential costs are often matched with more reliable income sources.
Step 3: List Every Income Source
Record each expected source of income and when it begins:
Social Security. You can claim as early as 62, and benefits increase for each year you delay up to age 70. Your statement at ssa.gov shows estimates at different ages. For married couples, claiming decisions can affect survivor benefits.
Pensions. Note payout options, such as single-life or joint-and-survivor, and whether there is a cost-of-living adjustment.
Rental or business income. Estimate what will continue and for how long.
Part-time work. Even modest earnings in early retirement can reduce how much you need to withdraw.
The gap between your spending and these sources is what your investments may need to cover.
Step 4: Inventory Your Investments and Accounts
List each account by tax type: taxable brokerage, tax-deferred (traditional 401(k), 403(b), 457, IRA), and tax-free (Roth). Include employer stock, deferred compensation, health savings accounts, and cash. Knowing the mix matters because each account type is taxed differently when you withdraw. Annual limits apply to contributions, so if you are still working, note whether you are using catch-up contributions available to older workers.
Step 5: Map Out Taxes in Retirement
Taxes rarely disappear in retirement. They change shape. Questions for this section of your retirement planning workbook:
Withdrawal order. Drawing from taxable, tax-deferred, and Roth accounts in a deliberate sequence may help manage lifetime taxes.
Roth conversions. Years between retirement and required distributions may offer a window to convert at lower rates. See our guide to converting pretax savings to Roth.
Required minimum distributions. Federal law requires withdrawals from most tax-deferred accounts beginning at an age set by statute, which has changed in recent years. Large balances can create larger required distributions later.
Medicare premiums. Higher income can increase Medicare Part B and Part D premiums, based on tax returns from two years earlier.
Coordinated tax planning and preparation can model these decisions across multiple years instead of one return at a time.
Step 6: Plan for Healthcare
If you retire before 65, note how you will cover health insurance until Medicare eligibility. After 65, compare Medicare options and supplemental coverage. It is also worth discussing long-term care: how it might be paid for and what role insurance, savings, or family support may play.
Step 7: Align Your Investment Strategy
Your portfolio in retirement has two jobs: fund near-term spending and keep growing for a retirement that may last decades. Many retirees hold a few years of planned withdrawals in more conservative investments, with the rest invested for long-term growth. Use the Compound calculator to see how a hypothetical portfolio may grow under different return and withdrawal assumptions. Results are hypothetical, but they can help you see how sensitive your plan is to spending and market conditions.
Step 8: Update Estate Documents and Beneficiaries
Review wills, trusts, powers of attorney, and healthcare directives with your estate attorney. Check beneficiary designations on every retirement account and insurance policy, since these generally override your will.
Retirement Planning in Wisconsin: Local Considerations
Retirement planning in Wisconsin has a few specific points worth reviewing. Wisconsin generally does not tax Social Security benefits, but other retirement income, such as IRA withdrawals and many pensions, may be subject to state income tax, and state rules can change. Property taxes are another meaningful line item for many Wisconsin homeowners. If you plan to split time between Wisconsin and a warmer state, residency rules can affect which state taxes your income. Our article on retirement planning in Wisconsin covers more of these considerations.
If you want a structured template for the rest of your finances, see our sample personal financial plan checklist.
How Compound Helps
Compound combines wealth management and investment management with tax planning, so retirement income, withdrawals, and taxes are planned together. We work with pre-retirees and retirees throughout Wisconsin, including Milwaukee, Madison, Green Bay, Appleton, Sheboygan, Wausau, and Eau Claire, as well as surrounding areas. If you are comparing options, read how to evaluate a financial advisor for retirees in Wisconsin.
Finished your workbook, or stuck on a step? Request a complimentary retirement wealth and tax review.
Frequently Asked Questions
What should be in a retirement planning workbook?
A retirement planning workbook typically covers your retirement goals, expected spending, income sources, account inventory, tax strategy, healthcare, investment allocation, and estate documents.
When should I start a retirement planning checklist?
Any time is useful, but ten years before retirement is a common point to get detailed. Many key decisions, like Roth conversions and Social Security timing, benefit from early planning.
Does Wisconsin tax retirement income?
Wisconsin generally does not tax Social Security benefits. Other retirement income, such as IRA withdrawals and many pensions, may be taxable at the state level. Rules can change, so confirm with a tax professional.
What is the best order to withdraw from retirement accounts?
There is no universal answer. The order depends on your tax bracket now and later, required distributions, Medicare premiums, and legacy goals. Modeling several scenarios can help.
How often should I update my retirement plan?
At least once a year, and after major events such as a job change, health change, inheritance, or significant market movement.
Compound is a registered investment adviser. Registration does not imply a certain level of skill or training. This article is for informational and educational purposes only and should not be construed as personalized investment, tax, or legal advice. Tax laws are complex and subject to change. Strategies discussed may not be suitable for everyone, and there is no guarantee that any strategy will achieve its objectives or reduce taxes. Calculator results are hypothetical, are not guarantees of future results, and do not reflect any actual investment. Investing involves risk, including possible loss of principal. Compound does not provide legal advice; please coordinate estate planning matters with an estate attorney. Please consult your tax, legal, and financial professionals before acting on any information in this article. For more information, see Compound's Form ADV, available at adviserinfo.sec.gov.
About Compound Wealth
Compound Wealth believes many financial decisions benefit from being evaluated together rather than independently. The firm integrates tax planning, wealth management, accounting, and business advisory services to help clients navigate financial complexity through a coordinated planning approach tailored to their evolving needs.
