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The 5-Year Countdown to Retirement

  • Writer: Luke Lloyd
    Luke Lloyd
  • Aug 21
  • 5 min read

Updated: 5 days ago

The 5-Year Countdown to Retirement

Retirement can feel like a distant finish line—until suddenly, it isn’t.

If you’re within five years of retirement, the game changes. You’re no longer just trying to accumulate as much money as possible. You’re preparing to turn your investments, Social Security, pensions, and other resources into a reliable income stream that may need to last 20, 30, or even 40 years.

The final five years before retirement are some of the most important years for financial planning.

Here are five areas to focus on.

1. Stress-Test Your Retirement Plan

Knowing your account balances is not the same as knowing whether you can retire.

You need to understand how your assets, expected spending, inflation, taxes, investment returns, and longevity interact.

Ask yourself:

  • How much will I actually need to spend each year?

  • What happens if the market falls 20% shortly after I retire?

  • How much guaranteed income will I have?

  • How long could my money realistically last?

  • What happens if I live into my 90s?

A retirement plan should be tested against multiple scenarios—not just the assumption that markets will deliver average returns every year.

2. Start Thinking About Income, Not Just Growth

During your working years, the primary question is often:

“How much can I accumulate?”

As retirement approaches, the question becomes:

“How do I turn what I’ve accumulated into sustainable income?”

This is where distribution planning becomes critical.

You may have money in a 401(k), Traditional IRA, Roth IRA, brokerage account, bank accounts, real estate, pensions, and Social Security.

The order in which you use those assets can have a significant impact on your lifetime taxes and the longevity of your portfolio.

Retirement isn’t simply an investment problem. It’s an income and tax-planning problem.

3. Get Serious About Taxes Before You Retire

One of the biggest mistakes people make is waiting until retirement to start thinking about taxes.

Your final working years may provide an important planning window.

Depending on your circumstances, strategies such as Roth conversions, charitable giving, tax-loss harvesting, capital-gains planning, or strategically managing retirement contributions may help improve your long-term tax picture.

The goal isn’t necessarily to pay the least amount of tax this year.

The goal is to manage your lifetime tax bill.

A decision that creates a little more taxable income today could potentially save significantly more in future years.

4. Protect Against the Risks You Can’t Afford

Five years before retirement is also a good time to review your insurance and risk management.

Consider:

  • Life insurance

  • Disability coverage

  • Long-term care

  • Umbrella liability coverage

  • Property and casualty insurance

  • Health insurance and Medicare planning

When you’re working, a large portion of your financial plan may be supported by your future earning ability.

Once you retire, that changes.

Your portfolio becomes a much larger part of your financial safety net.

Protecting what you’ve built becomes just as important as growing it.

5. Build a Retirement Lifestyle—Not Just a Retirement Number

Here’s the part that often gets overlooked.

People spend decades asking:

“How much do I need to retire?”

But a better question is:

“What do I actually want my retirement to look like?”

Do you want to travel?

Spend more time with family?

Start a business?

Move?

Buy a second home?

Golf three days a week?

Volunteer?

Help your children or grandchildren?

Retirement planning isn’t just about determining whether you have enough money. It’s about determining what you’re trying to accomplish with that money.

Your Five-Year Countdown Starts Now

If retirement is five years away, you don’t need to panic.

But you should have a plan.

The closer you get to retirement, the more important it becomes to coordinate your investments, taxes, Social Security, insurance, estate plan, and income strategy.

Don’t wait until your last day of work to start planning for your first day of retirement.

The best retirement plans aren’t built when you retire.

They’re built years before you retire.

Dream Bigger. Sleep Better.

Click here to schedule a meeting — I’m here to help you take the next step toward financial freedom.

Colin Symons, CIO Lloyd Financial Group

Jobless Claims were 206K vs. exp 210K, while Continuing Claims were 1.799M vs. prev. 1.777M. Not a big deal, but nervous markets sold off a bit on the slight strength. It is a nice trend lower in Continuing Claims, though.

Philly Fed Manufacturing was 47.4 vs exp. 25, with Employment and Prices Paid improving, though demand fell.

Japan’s Consumer Core Inflation rose to 1.8% Y/Y vs. prev. 1.6%, raising expectations of a rate hike.

Bitcoin rose above its 200DMA for the first time since 2025. It’s rallied from below 64K to almost 78K this week in part on the liquidation of $2.7B in shorts.

Broadcom (AVGO) was flat after announcing a $60B debt raise for AI chip financing. I mention it because that’s a change from the automatic declines we had been seeing on these announcements.

Walmart (WMT) was -9% after missing sales estimates and citing modest growth for next quarter.

OpEx (monthly Options Expiration) today should help the market start moving more freely. We also have S&P PMI.

Bottom line: Dollar weakness continues on Treasury plans

Click here to schedule a meeting — I’m here to help you take the next step toward financial freedom.

Disclosures/Regulation:

This content is intended to provide general information about Lloyd Financial. It is not intended to offer or deliver investment advice in any way. Information regarding investment services are provided solely to gain an understanding of our investment philosophy, our strategies and to be able to contact us for further information.

All information has been obtained from sources believed to be reliable, but its accuracy is not guaranteed. There is no representation or warranty as to the current accuracy, reliability or completeness of, nor liability for, decisions based on such information and it should not be relied on as such.

The views expressed in this commentary are subject to change based on market and other conditions. These documents may contain certain statements that may be deemed forward‐looking statements. Please note that any such statements are not guarantees of any future performance and actual results or developments may differ materially from those projected. Any projections, market outlooks, or estimates are based upon certain assumptions and should not be construed as indicative of actual events that will occur.

Past performance is no guarantee of future returns.

Different types of investments involve varying degrees of risk. Therefore, it should not be assumed that future performance of any specific investment or investment strategy will be profitable

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