Do You Have a Retirement Gap You’re Missing?

Most men in their fifties and sixties underestimate their retirement gap by a wide margin. It’s not because they’re bad with money or unwilling to prepare. It’s because they’ve never been shown a simple way to look at the numbers that actually matter.

If you’re feeling behind, confused, or unsure whether you’re going to be okay, you’re not alone. A lot of guys our age feel the same way. The good news is that clarity comes fast once you know what to look at. You can run your own numbers in about five minutes, and by the end of this article, you’ll know exactly how to do it.

And if you want a simpler way, I’ll give you a calculator that handles it for you. But let’s start with the foundation.

Most of us avoid the math because we expect it to be bad news. We put it off, not because we don’t care, but because we’re juggling careers, debt, aging parents, grown kids still needing support, and the general load of life.

Retirement planning often ends up on the “later” list.

There’s also a visibility problem. Most guys don’t really know where they stand. Yeah, they have a general idea, but not a clean picture they can point to and say, “This is my situation.”

You may even know guys who are doing great. 

They saved early, invested consistently, kept their lifestyle in check, and now they’re cruising toward retirement with confidence. If that’s you, then hat's off to you. Keep doing what you’re doing.

But for the rest of us, the ones feeling like the math may not be working, it’s time to get clear on what’s really happening.

And it’s not hard to see why things feel tighter today. We’re in a period where:

I'm not trying to sound all doom and gloom. Just to point out that this is the environment we’re planning inside of.

1. Your current monthly expenses

2. What those expenses might look like in retirement

3. Your Social Security estimate

4. Any pension or guaranteed income

5. The amount you’ve saved so far

6. The safe withdrawal rate you can apply to those savings

When you plug these pieces in, most guys discover their gap is somewhere between $1,500 and $2,500 per month. Not because they did anything wrong, but because life happened faster than their savings could keep up.

The gap is the part traditional retirement advice glosses over. You’ll hear talk about maxing out contributions and compounding returns, but almost nobody shows you how to measure the number you actually need to fix.

For decades, financial planners pushed the “4% rule.” The idea was simple: withdraw 4% from your portfolio each year, adjust for inflation, and your money should last 30 years.

That rule was built during a very different time. Back then:

Today, the safer withdrawal rate is closer to 3.3–3.5 percent.

That means if you retire with a million dollars — which used to be the American Dream number — your sustainable income from that portfolio isn’t $40,000 per year. It’s more like $33,000 to $35,000.

That’s a big difference. And it’s one of the reasons gaps are bigger than we expect.

There’s another factor that can make the gap even bigger, and it’s something most folks have never even heard of: sequence-of-returns risk.

Here’s the short version.

If the market drops early in your retirement — right when you start taking money out — it does far more damage than a market drop that happens later. You’re withdrawing funds from a shrinking account, which leaves less money to grow back when the market recovers.

And as we head into 2026, this risk matters more.

P/E ratios today are sitting at levels we’ve only seen a few times in history. Whenever valuations were this stretched in the past, a correction followed. Sometimes shallow. Sometimes not.

Chart from https://www.currentmarketvaluation.com/

I’m not predicting doom here. Markets can stay elevated longer than anyone expects. But if the market does revert to the mean — or even 150 percent of the mean — it would hit retirement portfolios hard.

And if that happened right when you retired or shortly after you started drawing down your accounts, it could make the gap wider very quickly.

I'm not trying to scare you here, just to make you aware of the possibilities.

And awareness gives you better options.

Here’s the truth most people won’t say out loud.

Saving more isn’t a bad idea. But when you’re in your fifties, saving alone usually isn’t enough to close a $1,500–$2,500 monthly gap.

Compounding works beautifully over thirty years. It doesn’t work as well over ten.

And if you had extra money lying around to invest every month, you’d probably already be doing it. So when financial gurus talk about “taking advantage of catch-up contributions,” that advice is great — for people who have thousands a month in discretionary income.

For the rest of us? It’s just a reminder of how far behind we feel.

So yes, save what you can. But don’t rely on saving alone to fix a problem that’s really about income.

This is the turning point.

For most of our lives, we were told to save as much as possible and let time do the work. And that works wonderfully when you’re 25 or 35. But at 55 or 60, time isn’t the tool it used to be.

So if you're behind the curve, it's time to stop focusing on saving more and start looking at earning more.

Not by working more hours… but by creating cash flow.

Because here’s the real goal at this stage in life:

That kind of income gives you stability today and security tomorrow.

You’re not just trying to build a massive portfolio anymore. Your job now is to build enough income to fill the gap. That requires a different strategy.

This is the shift from accumulation to income.
From hoping markets cooperate… to creating margin and control.
From fear… to clarity.

And once you start viewing your situation through that lens, the path forward is much easier to see.

Now let’s get practical.
Here’s how to calculate your gap in about five minutes:

1. Add up your current monthly expenses

2. Remove anything that won’t exist in retirement (commuting, certain insurance, work expenses)

3. Add anything that might increase (healthcare, travel, hobbies)

4. Check your Social Security estimate at SSA.gov

5. Add any pension or guaranteed income

6. Multiply your savings by 3.3% or 3.5% to find your safe annual withdrawal

7. Convert that to a monthly number and add it to Social Security

8. Subtract what you have coming in from what you need

That’s your gap.

If you don’t feel like doing all that manually, you can use the tool I built:

👉 Use the Retirement Gap Calculator here

It does all the math for you and gives you a clear picture in seconds.

Once you know your gap, something interesting happens.
You realize you don’t need a miracle — you need margin.

For most men, an extra $1,000 to $2,000 a month solves the problem. It closes the gap, accelerates debt payoff, lowers your monthly burn, and gives you room to invest more.

It’s also the number one way to create stability that carries into retirement.

This doesn’t mean getting a second job and losing your evenings. It means building a small engine of cash flow — something steady, simple, and sustainable — that follows you into your sixties and seventies.

That’s how you put the missing comma back in your portfolio.

You don’t fix retirement by ignoring it.
You fix it by seeing it clearly.

Once you know your retirement gap, you can build a real plan that fits your life and your goals. And that starts with a few simple numbers.

If you haven’t already, take a minute and run your numbers:

👉 Check your Retirement Gap here

It’s the fastest way to turn uncertainty into clarity.

And if you want more practical strategies on income, retirement planning, and building a better financial life for the next chapter, stick around. That’s what Missing Comma is all about.