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Ready to Retire? Make Sure You’ve Hit These 9 Financial Milestones

July 24, 2025 By Catherine Reed Leave a Comment

Ready to Retire Make Sure You've Hit These 9 Financial Milestones

Retirement is a significant life event that many look forward to, but it comes with its own challenges, especially financially. Being ready to retire isn’t just about reaching a certain age; it involves meeting key financial milestones that ensure you can enjoy your golden years without financial worry. Here, we explore nine essential financial milestones to achieve before you decide you’re ready to retire. These goals will help you assess your readiness and ensure a solid financial foundation for the next phase of your life.

1. Debt-Free Living

Debt-Free Living

One of the most crucial financial milestones before retirement is eliminating high-interest debt, particularly credit card debt and personal loans. Carrying debt into retirement can significantly strain your finances, as fixed retirement income might not cover debt repayment and living expenses. Ideally, your mortgage should also be paid off, allowing you to live more freely without the burden of monthly loan payments. This milestone ensures that your retirement savings and income are devoted to your living expenses and enjoyment rather than paying off debts.

2. Building Adequate Retirement Savings

Adequate Retirement Savings

Ensuring you have enough saved to cover your retirement years is critical. Financial experts often recommend having at least 10-12 times your final pre-retirement salary saved. This should ideally be a mix of retirement accounts like 401(k)s, IRAs, and other savings or investment accounts.  If you haven’t already figured out how much money you need in retirement, assume at a minimum that you’ll need 75% of your current salary.  Next assume you can withdraw 4% from your nest egg per year.  Then compare the two figures.  This should tell you if you’ve got enough saved.

3. Healthcare Planning

Healthcare Planning

Healthcare costs in retirement can be significant. Having a comprehensive healthcare plan, including Medicare and supplemental insurance, is crucial. Consider the costs of long-term care insurance, which can cover expenses not included in regular health insurance. Being prepared for unforeseen health issues by having this coverage in place can prevent significant financial strain later.

4. A Tested Retirement Budget

A Tested Retirement Budget

Before you retire, test out a retirement budget. Try living on your expected retirement income for several months while still working. This will help you adjust your spending habits and ensure your budget is realistic based on your retirement income. This trial period can reveal unexpected costs and help you refine your budget before you fully commit to retiring.  Remember, nothing says you have to stop working in retirement – you can always work on smaller projects to bring in money or take a part time job.

5. Diverse Income Streams

Diverse Income Streams

Relying solely on savings or Social Security can be risky. Having multiple income streams can provide extra security. Consider rental properties, bond payments, dividends from investments, or a part-time job if you want to keep working. This diversification helps buffer against poor market performance that could affect your primary retirement funds.  A good place to start is by finding dividend stocks with an AI generated list.  Or, if you want an old fashioned human curated list, a good place to start would be the dividend aristocrats – or companies that have consistently raised their dividends for decades (here).

6. Updated Estate Plan

Updated Estate Plan

An updated estate plan is vital as you approach retirement. This includes having a will (or revising your current one), designating powers of attorney, and potentially creating trusts. These documents should be reviewed and updated to reflect your current wishes and ensure your assets are distributed according to your plans without legal complications.

7. Long-Term Investment Strategy

Long-Term Investment Strategy

Having a long-term investment strategy that shifts from accumulation to income generation is crucial. This strategy should be less about aggressive growth and more about preserving capital and generating a steady income. A financial advisor can help, but there are plenty of DIY tools available as well.  Most of the major brokerages like Schwab or Fidelity offer these kinds of tools – check your portfolio check up section.

8. Social Security Strategy

Social Security Strategy

Deciding when to start taking Social Security benefits is a significant decision. Although you can begin collecting benefits at age 62, delaying benefits until your full retirement age or even age 70 can significantly increase your monthly payments. Evaluate your health, financial needs, marital status and life expectancy to make an informed decision that maximizes your benefits.  Schwab has a good basic overview of factors pertinent in deciding when to take Social Security, here.

9. A Plan for Leisure and Lifestyle Goals

A Plan for Leisure and Lifestyle Goals

A major factor many retirees face when they first begin retirement is cognitive decline and associated mental health issues such as depression and anxiety.  However, research shows that an active lifestyle including maintaining hobbies and building or maintaining strong interpersonal relationships can reverse this decline (per Forbes).  Whether it’s traveling, hobbies, or spending time with family, make sure you plan how you want to spend your time. This includes budgeting for activities you enjoy and considering any potential costs associated with these pursuits.

These Financial Milestones Could Mean You’re Ready to Retire

These Financial Milestones Could Mean You’re Ready to Retire

Achieving these financial milestones can make the difference between a stressful retirement and a fulfilling and secure one. Being ready to retire means more than just stopping work; it involves meticulous planning and preparation to ensure your retirement years are as enjoyable as possible. Each milestone is a step toward creating a stable and rewarding retirement experience, giving you the peace of mind to fully enjoy this new chapter of your life.

Read More:

12 Cities You Wouldn’t Believe Are Retirement Paradises

5 Facts to Keep in Mind About Estate Planning

Catherine Reed
Catherine Reed

Catherine is a tech-savvy writer who has focused on the personal finance space for more than eight years. She has a Bachelor’s in Information Technology and enjoys showcasing how tech can simplify everyday personal finance tasks like budgeting, spending tracking, and planning for the future. Additionally, she’s explored the ins and outs of the world of side hustles and loves to share what she’s learned along the way. When she’s not working, you can find her relaxing at home in the Pacific Northwest with her two cats or enjoying a cup of coffee at her neighborhood cafe.

Filed Under: Retirement, ShareMe Tagged With: financial milestones, financial planning, ready to retire, Retirement, retirement income, retirement planning

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