Jeremy Keil explains the 5 steps you can take if you are planning to retire in 2026 or 2027.

If you’ve been planning to retire in 2026 or 2027, it might feel like you still have plenty of time. But in reality, retirement has a way of showing up earlier than expected — and when it does, the people who feel the most confident are the ones who prepared well in advance.

In this episode of Retire Today, I walk through five things you should do before you quit working if retirement is anywhere on your near-term horizon. These steps aren’t about picking a perfect retirement date. They’re about being ready — even if your plans change.

Two important statistics shape this entire conversation.

First, the stock market is historically up about 70% of the time in any given year. That also means it’s down about 30% of the time. If you’re retiring soon, there’s a real chance that your account balances could be lower at retirement than they are today.

Second, most Americans retire about three years earlier than they expect. Health changes, job shifts, burnout, or family needs often move retirement forward — whether planned or not.

That’s why I encourage people to prepare for retirement three years ahead of time, even if they believe they’ll work longer. Planning early gives you flexibility. Waiting too long removes it.

The first and most important step is to put your plan in writing.

Many people have a retirement date in mind, but when asked how everything will actually work, they don’t have clear answers. A written plan forces clarity.

This is where the 5-Step Retirement Plan comes in:

• What you’ll SPEND
• What you’ll MAKE
• What you’ll KEEP after taxes
• How you’ll INVEST
• What you’ll LEAVE behind

Writing this down helps turn vague ideas into an actionable roadmap — and exposes gaps before they become problems.

Retirement isn’t about having a big account balance — it’s about knowing where your income will come from every month.

Before you retire, you should know:

• How much income you need
• Where that income will come from
• Which accounts you’ll use first
• How taxes affect each withdrawal

At a minimum, you should map out the first 12 months of retirement income in detail. That includes Social Security, pensions, savings, brokerage accounts, and retirement accounts — and the tax rules that apply to each one.

Surprises here are costly. Planning removes them.

Many people assume their taxes will automatically go down in retirement. Sometimes that’s true — but not always.

Pensions, Social Security, required minimum distributions, and investment income can push retirees into higher tax brackets than expected. The key is understanding when you’ll have flexibility and using it intentionally.

Retirement often creates opportunities to:

• Shift income between tax years
• Take advantage of lower tax brackets
• Manage Roth conversions strategically
• Plan around healthcare subsidies

Taxes don’t disappear in retirement — they change. Planning ahead helps you adapt.

Healthcare is one of the biggest unknowns in retirement.

Before you retire, you should know:

• What coverage you’ll use immediately
• What it will cost
• How that coverage changes over time
• When Medicare becomes part of the picture

Options may include employer coverage through a spouse, COBRA, retiree health plans, ACA plans, or Medicare — and each comes with different costs and rules.

Healthcare planning isn’t just about insurance. It’s about understanding how medical costs interact with your tax plan and your income strategy.

Retirement changes your investment timeline. You’re no longer investing only for growth — you’re investing for income and stability, too.

That means separating your money into:

• Short-term funds for near-term spending
• Long-term investments for growth over decades

Money you’ll need soon shouldn’t be exposed to short-term market swings. At the same time, money you won’t need for many years still needs growth to keep up with inflation.

The right investment plan balances both — and helps prevent panic decisions when markets get volatile.

If you’re planning to retire in 2026 or 2027, now is the time to prepare. Not because something bad will happen — but because preparation gives you options.

Retirement doesn’t have to be so stressful. With a written plan, a clear income strategy, smart tax planning, healthcare clarity, and a thoughtful investment approach, you can step into retirement with confidence — whenever it arrives.

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About the Author:

Jeremy Keil, CFP®, CFA® is a financial advisor in Milwaukee, WI, author of the bestseller Retire Today: Create Your Retirement Master Plan in 5 Simple Steps and host of both the Retire Today Podcast and Mr. Retirement YouTube channel

Additional Links:

• Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
• Create your retirement master plan in 5 simple steps: www.5StepRetirementPlan.com 

Connect With Jeremy Keil:

• Keil Financial Partners
• LinkedIn: Jeremy Keil
• Facebook: Jeremy Keil
• LinkedIn: Keil Financial Partners
• YouTube: Mr. Retirement
• Book an Intro Call with Jeremy’s Team

Media Disclosures:

Disclosures

This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.

The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past performance is no guarantee of future results.

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