The 10 decisions that matter most in the final stretch to retirement

By Amanda Stilwell
Founder and Senior Wealth Advisor
Clarity Financial Solutions

 

The five years before retirement may be the most important of your financial life.

For many professionals, retirement planning has been a decades-long journey of saving, investing and preparing for the future. But as retirement draws closer, the focus begins to shift. It’s no longer just about building wealth- it is about strategic decisions to use and preserve what you have saved.

The final five years before retirement are often when the biggest financial opportunities—and if overlooked, can be some of the costliest mistakes—occur. Decisions about taxes, Social Security, healthcare and income planning can have lasting effects on how comfortably you live for the next 20 or 30 years.

If you’re approaching retirement, here are 10 decisions worth making before you hand in your retirement notice.

1. Know Your Retirement Number

Retirement isn’t about losing or replacing your paycheck—it’s about the income needed to fund your lifestyle.

Estimate what you’ll actually spend each month, including housing, healthcare, travel and everyday living expenses. The biggest number to know is, out of your retirement savings, how much of it is yours and how much of it belongs to Uncle Sam. Many people discover they either need less than expected—or considerably more.

2. Decide When You’ll Claim Social Security

Claiming Social Security is one of the most important retirement decisions you’ll make.

While benefits can begin at age 62, delaying benefits may increase your monthly income depending on your circumstances. Factors like life expectancy, marital status and other retirement income should all be considered before making a decision.

The Social Security Administration offers calculators and planning tools at:
https://www.ssa.gov/benefits/retirement/

3. Create a Retirement Income Plan
Accumulating savings is only half the equation.

Before retiring, determine where your income will come from each month, including:

• Social Security
• Employer retirement plans
• IRAs
• Taxable investment accounts
• Pension income, if applicable

Having a written withdrawal strategy can help provide consistency while reducing unnecessary taxes and surcharges, like Medicare premiums, which are based on income.

4. Review Your Tax Strategy

Many retirees assume they’ll be in a lower tax bracket when they stop working.

That’s not always true.

Retirement account withdrawals, Social Security benefits, investment income and Required Minimum Distributions (RMDs) can all affect your tax bill. Reviewing tax strategies before retirement may create opportunities that disappear once you’re retired.

5. Prepare for Healthcare Costs

Healthcare is often one of retirement’s largest expenses.

If you plan to retire before age 65, you’ll also need a strategy for health insurance before Medicare begins.

Review:

• Medicare enrollment timelines
• Health Savings Accounts (HSAs)
• Long-term care planning
• Estimated out-of-pocket expenses

6. Stress-Test Your Investment Portfolio

The years immediately before and after retirement can be especially sensitive to market volatility.

Now is a good time to evaluate whether your investment allocation still aligns with your timeline, income needs and risk tolerance—not simply your growth objectives.

7. Review Your Estate Plan

Your estate documents should reflect your current life—not the one you had 20 years ago.

Review:

• Revocable or Irrevocable trusts vs. a will
• Powers of attorney
• Healthcare directives
• Beneficiary designations

Even small updates can help ensure your wishes are carried out efficiently.

8. Think About Taxes Before You Retire

Some tax-planning opportunities are easier to implement while you’re still working.

Depending on your situation, strategies such as Roth conversions or coordinating retirement account withdrawals may help improve long-term tax efficiency.

The IRS provides retirement planning guidance at:
https://www.irs.gov/retirement-plans

9. Plan for Life Beyond Your Career

Retirement isn’t just a financial transition—it’s a personal one.

Many new retirees underestimate how much their routines, social connections and sense of purpose change after leaving the workforce. Consider how you’ll spend your time, stay active and remain connected to your community.

10. Meet With Your Financial Team

The closer retirement gets, the more important coordination becomes.

Your financial advisor, CPA and estate planning attorney each bring different expertise. Reviewing your plan together before retirement can help identify gaps and ensure your investment, tax and estate strategies are working toward the same goals.

The Bottom Line

Most retirement mistakes don’t happen because people failed to save enough. They happen because important decisions were delayed or made without understanding how one choice affects another.

The final stretch before retirement is an opportunity—not just to prepare financially, but to build confidence for what’s ahead. Taking the time now to review your income plan, tax strategy, healthcare and long-term goals can help turn years of saving into a retirement that’s both financially secure and personally fulfilling.

 

About Clarity Financial Solutions

Clarity Financial Solutions provides personalized financial guidance focused on retirement strategies, wealth preservation and insurance planning. By simplifying complex financial concepts, the firm helps clients make informed decisions aligned with their long-term goals.

Clarity Financial Solutions is a dba of The Wealth Boutique, a registered investment advisor with the Securities and Exchange Commission. The Wealth Boutique and each of the DBAs are not under common ownership. All financial planning and advisory services are provided by The Wealth Boutique. All investments involve risk and unless otherwise stated, are not guaranteed. Be sure to consult with a tax professional before implementing any investment strategy.