Oliver Wealth Management’s Retirement Checklist

If you’re planning to retire, you have a lot to consider. The best strategy is to develop a retirement checklist. 

Retirement plans differ – there isn’t one template for everyone! Finances differ as well. But the process of preparation is generally the same. 

Many people have anxiety about finances in retirement. In fact, 40 percent of Americans fear they will run out of money in retirement. It’s important to allay this fear with a strategy that will provide you with a comfortable – and anxiety-free – retirement.

So, whether you have plans to spend time with your grandchildren or start a business in your newfound free time, there are 5 important steps to consider.

1. Decide What Retirement Looks Like for You 

Everyone’s picture of what retirement looks like is different. It’s time to create a realistic picture of what yours will be like. Start with an overview of your retirement goals. Do you want to travel? Relocate? Take classes? Start that business? Continue to work?

Who will be retiring with you? If a spouse, will your spouse also be retired? Will other family members be around? Who, and how often?

Also ask yourself where you envision living. (Retirement planning in Towson, MD is different than in other areas.) Will you be staying in your current house? Think about whether your current arrangements will work when you are older. If children have moved out, your current home may feel too large. Maintenance may become a chore you no longer want to do. Will you downsize in retirement? Move? 

If you plan to either downsize or move, get a good sense of how much real estate will cost you. Real estate prices are tremendously variable throughout the country – and overseas as well. Check out the picture for property and other taxes before making plans.


It’s never too early to start planning for the future. Contact Oliver Wealth Management to see how we can help. 


2. Create a New Budget for Retirement

Develop a working budget plan for your retirement years. Your expenditures in retirement will likely be roughly 80 percent of your expenditures before retirement. But this rule of thumb is only a guide, of course. If you move to an area with more affordable real estate and downsize, your costs could be less. Real estate accounts for about one-third of most retirees’ budgets. If you travel more extensively, your monthly costs could be more than they were before retirement.

Plan realistically for health care costs. You are likely to need more health care as you age, as older people are more likely to develop conditions that need care. Retirees spend, on average, nearly $6,000 per year for health care. Health care costs have also risen sharply in the past several decades, and that trend may continue. During the 2000-2018 period, for example, the costs of prescription drugs went up 188 percent, and the costs of Medicare coverage increased 195 percent. 

Also take into consideration that retirees’ life expectancy is longer now than it was years ago. Now, many people retiring at 65 have a life expectancy of 84 (men) and 86-½ (women). If you plan to retire at 66, that’s roughly two decades of retirement living. Your costs in all categories are highly unlikely to remain static during that time. It can be beneficial to work with a financial advisor to make sure your budgets are realistic over time.

3. Take a Look at Your Retirement Income

Anxiety about outliving retirement income is common enough that strategies have been developed to deal with it. One well-known method is the 4 percent rule, which was devised in the 1990s. Simply put, the 4 percent rule holds that if retirees withdraw 4 percent of their portfolio every year, their money will last 30 years. 

This rule, of course, is highly dependent on the expected span of your retirement. Thirty years may be sufficient. But if you retire earlier than your mid-60s, or you are expected to live longer than 30 years past retirement, it may be prudent to adjust the 4 percent rule accordingly.

Another thing to consider: If your retirement portfolio is in stocks, it is highly subject to stock market fluctuations. The stock market will inevitably experience down years. Over time, these are more than counterbalanced by up years. However, as people grow older, there is less time for any drops caused by bear markets to be made up. As a result, it’s prudent for older people to have proportionally more of their money invested with less risk to fluctuations. 

Rebalancing your portfolio and reviewing your financial plan every year is wise.

4. Review Income Streams

Along with knowing your plan and your budget in retirement, of course, you need to know your income streams. Is Social Security likely to be one? Access your expected benefits, if so. (Retirement planning for business owners and attorneys can propose different concerns.) Will you have income streams from tax-advantaged retirement accounts, such as 401(k)s and traditional Individual Retirement Accounts (IRAs)? You can start withdrawing from these when you’re 59-½, and you must start withdrawing at 70-½ or face tax penalties. Will you have a pension? An annuity?

Develop a working plan for what each income stream will be worth to you in retirement. Be sure to calculate when each income stream will become available.

5. Decide When to Retire 

The checklist steps above will help you plan for retirement before you retire. Developing your life goals and making sure that your budget and income track with the realistic achievement of them is crucial. 

Once you know your expected expenditures and have forecast the income you’re likely to have in retirement, you can decide when to retire. Some people decide to work longer than they’d initially planned, to make their income in retirement last longer. Others may find their initial plan realistic or even move up the date. This checklist gives you a blueprint for your financial life in retirement.