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.

Why You Should Prepare Earlier Than You Think

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.

1. Create a Written Retirement Plan

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

Putting this into a written retirement master plan turns scattered ideas into a coordinated strategy — and reveals gaps while you still have time to fix them.

2. Build a Lifetime Income Plan

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.

3. Make Your Retirement Plan Tax-Smart

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.

4. Plan Your Retirement Healthcare

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.

5. Create a Retirement Investment Plan

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.

The Bottom Line

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:

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.

Legal & Tax Disclosure

Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.

Advisor Disclosures

Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.

Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at htt...