Social Security & Pension Planning:

Q: When should I take Social Security?

It depends on your plan—not a rule of thumb. The first step is to discover your longevity estimate, and the probability you, and your spouse, will make it to certain ages.

Q: Should I delay Social Security, or take it early?

Most advisors, and retirement experts, suggest you delay Social Security. Many of your friends will tell you to take it early. We believe, before you take your Social Security, you need to learn the math, do the math, and follow the math – and often, you’ll be surprised at the best answer!

Q: How does my Social Security decision affect my spouse?

We believe what happens to the Survivor benefit is one of the most important factors for your Social Security decision. No matter who dies first, the smallest Social Security goes away—which means the bigger benefit is the one you need to optimize to help the surviving spouse.

Q: How is Social Security taxed?

Up to 85% of your Social Security can be taxable, depending on your total income. This can cause higher than expected marginal tax rates, often called the ‘Social Security Tax Torpedo.

Q: Can I change my decision later?

In theory, yes. Practically, no. We’ve helped hundreds of people file for Social Security and can only recall two individuals actually change their Social Security decision using either the ‘withdraw’ or ‘suspend’ rules.

Q: When should I start my pension?

Many people assume their only option is to start their pension the day they retire, or perhaps at their ‘normal retirement age.’ We help you get all your options and compare the value of different starting dates based on present value calculations and our proprietary ‘lifetime yield’ calculations.

Q: How is my pension taxed?

Pensions are taxed, fully, as ordinary income, although some pensions have a smaller amount of tax-free return of basis associated with contributions you made long ago.

Q: Can I change my pension later?

Generally, No. Your decision is permanent – at least every single one of the 100s of pensions we’ve seen is permanent after you take your first payment.

Q: Why get help with Pension Planning?

Because your HR department can’t give you advice, and your co-worker probably didn’t properly compare their options. Even if they didn’t, they don’t know the math of your situation. You’ve worked hard for your pension and you deserve to get the most out of it.

Getting These Important Decisions Right

There are a few decisions in retirement you don’t get to redo.

Social Security and your pension are two of them.

Once you choose:

When to start Social Security
How to take your pension
And which option you select

those decisions often stay with you for the rest of your life.

That’s what makes them feel different.

Not complicated.

Just… permanent.

Why Your Social Security and Pension Decisions Feel So Hard

Most people don’t struggle because they can’t understand the options.

They struggle because the decision isn’t just about one thing.

You’re not just deciding:

“When should I take Social Security?”

You’re also affecting:

How much income you’ll need from your investments
How your income is taxed
What your spouse would receive later
How confident you feel about the rest of your plan

Same thing with your pension.

It’s not just:

“Lump sum payout or monthly annuity?”

It’s:

How does this fit into my lifetime income needs?
What does this mean for my spouse?
How does this affect flexibility later?

Everything connects.

And that’s what makes it hard to feel confident you’re making the right choices.

The Social Security Question Most People Ask

Most people start with:

“When should I take my Social Security?”

But that’s not really the decision.

A better question is:
“What makes the most sense based on how my entire retirement plan works?”
Because the right answer isn’t the same for everyone.

It depends on:

Your life expectancy
Your income needs
Your retirement savings
Your other income sources
Your tax situation
Your goals as a couple

That’s why general rules can only take you so far.

Where Social Security and Pensions Fit into Your Retirement Plan

In the Retirement Master Plan process developed by our founder, Jeremy Keil, this fits into the second step, part of the “Make” decision—where your income actually comes from.

It’s how you turn:

Social Security
Your pension
And your investments

into a coordinated income plan.

If you’ve read Jeremy Keil’s book, Retire Today, this is one of the key moments in the process.

Because once these decisions are made, they shape how everything else works.

How We Help You Make Your Social Security and Pension Decisions

We don’t look at Social Security and your pension separately.

We help you see how they fit into your full plan.

Social Security: More Than a Start Date

We walk through:

What your benefit actually looks like over time
How it fits with your other income
How it affects your taxes
What it means for your spouse

So instead of guessing or following a rule, you can make a decision that fits your situation.

Your Pension: More Than a Single Choice

For many people, this is one of the biggest financial decisions they’ll make.

We help you compare:

Lump sum vs. monthly pension
Different starting dates so you get the best advantage of your pension rules
Different payout options (single life, joint, etc.)
How each option affects your income and flexibility

How Social Security and Pension Decisions Fit Into Your Retirement Plan

Most people look at Social Security and their pension as two separate decisions.

But once you start putting a plan together, you realize they’re connected.

The choice you make with your pension affects how much income you need from your investments.

When you start Social Security changes how long your investments need to carry the load.
And both decisions influence how your income is taxed over time.

That’s why we don’t look at your Social Security and pension decision in isolation.

We help you see how each choice fits into your overall plan—so you can make a decision that makes sense not just on its own, but as part of everything else.

Why Your Social Security and Pension Planning Matters

The difference between “good” and “better” decisions here can add up over time.

But what matters more is this:

You understand how your income works.

You’re not second-guessing.

You’re not wondering if you should have done something different.

You can move forward knowing your decisions fit your plan.

Where People Get Tripped Up With Their Social Security and Pension Decisions

Most mistakes don’t come from bad intentions.

They come from making these decisions in isolation.

We often see people:

Take Social Security based on a rule of thumb
Choose a pension option based on what their co-worker told them
Ignore how taxes affect the decision
Make one choice… without seeing how it affects the others

Making decisions based on myths and hearsay don’t always add up to the best outcome.

How Keil Financial Partners helps you plan your Social Security and Pension

We help you:

Understand your options clearly
See how each decision affects your full plan
Make a choice you feel confident about
Update your plan as your situation, markets and laws change

Our team has been helping retirees navigate decisions like these for over twenty years.

And what we see is consistent:

The people who feel best about retirement aren’t the ones with the most money.

They’re the ones with a clear plan.

Who Social Security and Pension Planning Is For

This type of retirement planning is typically a good fit if:

You want to retire within the next five years—even within the next 12 months.
You’ve built retirement savings of $500k–$5M+
You have a pension, 401(k), or both
You want to make informed decisions—not guesses

Most of the people we work with are thoughtful and analytical.

They’ve been successful in their careers.

They’re used to being the expert.

But retirement is different.

You only do it once.

You’ve never done it before.

And you want to get it right.

Social Security and Pension Planning (Based in Milwaukee, Working Nationwide)

If you’re trying to make these decisions, you’ll find plenty of general advice online.

But not much that applies directly to your situation.

Keil Financial Partners is based in the Milwaukee area, and we work with individuals and couples both locally and across the country who are:

Deciding when to take Social Security
Evaluating pension options
Coordinating these decisions with their retirement income
And trying to make sure everything works together

FAQ

Social Security Planning

When should I take Social Security?

Should I delay Social Security, or take it early?

How does my Social Security decision affect my spouse?

How is Social Security taxed?

Can I change my decision later?

Pension Planning

Should I take a lump sum payout or monthly pension annuity?

Many people do what feels best, or what their co-worker suggested. We believe you should get all the pension information, comparing different start dates and different ways to take the pension, as well as compare the value of the pension against the value of similar, commercially available options—only then can you tell the true value of each option and which option has hidden value.

When should I start my pension?

How is my pension taxed?

Can I change my pension later?

Why get help with Pension Planning?

A Simple Way to Get Started

You don’t have to guess your way through these decisions.

The first step is a conversation.

We’ll help you understand:

What your Social Security and pension options really look like
How they fit into your plan
What your next step should be

Most of these decisions don’t feel urgent—until your paycheck stops.

That’s usually when people wish they had a plan in place.

Schedule Intro Call

See How We Help You Retire