Jeremy Keil walks through three critical questions future retirees can answer before their paycheck stops

Most people spend decades preparing for retirement by focusing on one number:

How much have I saved?

But retirement isn’t really about the size of your portfolio.

It’s about whether you can turn that portfolio into reliable income that supports the life you want.

That transition—from saving money to living on it—is where retirement planning becomes real.

And if you’re retiring within the next 12 months, there are three questions you can answer before your paycheck stops.

Unfortunately, this is where many people start with the wrong approach.

Most retirees try building a budget from scratch. They estimate utilities, groceries, gas, dining out, subscriptions, and dozens of other categories.

The problem?

Those budgets are almost always wrong.

They tend to assume:

Instead of trying to build a perfect budget from zero, Jeremy recommends a simpler and often more accurate approach:

Look at what already happened.

Specifically:
What actually went into your checking account over the last 12–24 months?

Because in most households, what goes into checking eventually gets spent.

That “take-home pay” becomes a much better starting point for estimating retirement income needs.

But there are a few important adjustments.

Your paycheck today already has several things removed before it hits your checking account:

Once you retire:

That means your gross salary is not the same as your retirement income need.

Many find it valuable to separate out:

Retirement spending isn’t just monthly bills.

It’s the full picture.

Most people already have an answer to this question before they ever run the numbers.

And often, that decision is emotional.

Maybe a parent died young. Maybe a friend claimed at 62. Maybe someone simply wants to “get their money.”

But what if you about Social Security differently?

Not as an investment.

As insurance.

The official name of the program is Old-age, Survivors, and Disability Insurance. That framing matters.

Social Security exists to help:

In other words, Social Security is there to protect against things not going according to plan.

That’s why filing decisions shouldn’t be based only on “break-even” calculators.

The better question is:
What role does Social Security play in protecting your retirement?

One of the biggest mistakes retirees make is treating retirement like a light switch.

They assume:
Growth before retirement.
Income after retirement.

But markets don’t work on your timeline.

Jeremy shared a powerful example from 2020:
People planning to retire within a year stayed fully invested in stocks because markets had been performing well.

Then COVID hit.

Markets dropped sharply, and many panicked—selling near the bottom because they suddenly realized they needed that money soon.

The issue wasn’t just the market drop.

It was that their investments weren’t aligned with their time horizon.

Get your investments ready to retire three years before retirement.

Why?

Because roughly half of retirees stop working earlier than expected.

If your investments are prepared ahead of time:

But there’s balance here too.

Retirement doesn’t mean abandoning long-term growth entirely.

If retirement could last 25–30 years, some money still needs long-term growth potential.

The key is having:

Not all one or all the other.

Retirement isn’t just about stopping work.

It’s about replacing a paycheck with a plan.

And before your paycheck disappears, you should know:

Because when those three pieces work together, retirement becomes much more than a date on the calendar.

It becomes sustainable.

Don’t forget to leave a rating for the “Retire Today” podcast if you’ve been enjoying these episodes!

Subscribe to Retire Today to get new episodes every Wednesday.

Apple Podcasts: https://podcasts.apple.com/us/podcast/retire-today/id1488769337 

Spotify Podcasts: https://bit.ly/RetireTodaySpotify

About the Author:

Jeremy Keil, CFP®, CFA is a retirement financial advisor with Keil Financial Partners, author of Retire Today: Create Your Retirement Income Plan in 5 Simple Steps, and host of the Retirement Today blog and podcast, as well as the Mr. Retirement YouTube channel.

Jeremy is a contributor to Kiplinger and is frequently cited in publications like the Wall Street Journal and New York Times.

Additional Links:

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 https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.

The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.

Additional Important Disclosures