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Retirement planning guide

A simple plan for the people you love and the life you've built.

Retirement isn't a single decision — it's how Social Security, savings, life insurance, long-term care, and taxes all fit together. This guide walks you through each piece in plain English so you can sit down with Michael already knowing the right questions to ask.

The roadmap

The 5 steps every family needs to walk through.

Most people are doing 2 or 3 of these well. The trouble is almost always in the ones they haven't thought about yet.

Step 01

Know your number

Add up what you actually need each month in retirement — mortgage or rent, groceries, utilities, insurance, gas, and a little fun money. That number, not a generic target, is what your plan has to produce.

Use the prep checklist below

Step 02

Lock in guaranteed income for the essentials

Social Security plus a properly structured annuity can cover the must-pay bills for life, so a bad year in the market never threatens the lights, the mortgage, or the groceries.

How annuities work

Step 03

Protect the house and the spouse

Make sure that if something happens to you, the mortgage gets paid, your spouse keeps their income, and the kids' plans don't fall apart. The right life insurance turns a worst-case day into a survivable one.

See life insurance

Step 04

Plan for health and long-term care

Medicare doesn't cover long-term care, and 7 in 10 people over 65 will need some. A plan now keeps the cost — and the caregiving — from landing on your spouse and kids.

Long-term care options

Step 05

Coordinate Social Security and taxes

When you and your spouse claim, which accounts you draw from first, and how you handle Roth conversions can mean tens of thousands of dollars over a retirement. We map it out together.

Ask Michael a question
Real family scenarios

You'll probably see your own family in one of these.

Composite examples drawn from real households Michael has worked with. Names and details changed for privacy.

The Andersons — 58 & 56

$420k in a 401(k), 9 years left on the mortgage, two kids out of college. Tom is a project manager, Lisa works part-time at the school.

The worry

They were saving hard but had no idea what their actual monthly retirement paycheck would look like — and Tom's 20-year term policy expires in 4 years, right as he plans to retire.

The plan

We mapped a $4,800/month income floor using Social Security at 67 plus a fixed annuity, kept a smaller permanent life policy on Tom so Lisa never has to sell the house, and re-routed extra savings into a Roth.

Maria — 62, recently widowed

Inherited a $300k IRA, a paid-off house, and her husband's small pension survivor benefit. Two grown kids, three grandkids.

The worry

She was terrified of outliving the money and didn't know whether to claim Social Security now at 62 or wait. A neighbor told her to put it all in the market.

The plan

We delayed her Social Security to 67 (a ~32% bigger check for life), used part of the IRA for guaranteed income to bridge those years, and put a long-term care plan in place so the kids never have to choose between her and their own families.

The Patels — 49 & 47

Two kids, ages 12 and 9. $185k in retirement accounts, a 28-year mortgage, both parents working full-time.

The worry

Plenty of time — but only if nothing goes wrong. They had no life insurance beyond a small work policy and no plan for college costs alongside retirement.

The plan

Affordable 25-year term policies on both parents (under $90/month combined) so the mortgage and kids are protected, plus a clear savings split so retirement and college both stay on track.

Avoid these

The 5 most expensive retirement mistakes we see.

Each of these is fixable — but only before they happen. A 30-minute conversation now can be worth tens of thousands of dollars later.

Talk it through with Michael
1

Claiming Social Security at 62 by default

Every year you wait between 62 and 70 grows your check for life. For many couples, the right claiming order is worth $50,000–$150,000 over retirement.

2

Assuming Medicare covers long-term care

It doesn't. Medicare covers short rehab stays — not ongoing help with bathing, dressing, or memory care, which can run $6,000–$10,000 a month.

3

Hanging on to a 30-year-old term policy that's about to expire

If your term is ending in the next 5–10 years and the mortgage or a spouse still depends on your income, you have options now that you won't have once it lapses.

4

Treating the 401(k) as the whole plan

A 401(k) is an account, not a paycheck. Without a plan to convert it into reliable monthly income, a bad market in your first few retirement years can permanently shrink it.

5

Naming the wrong (or no) beneficiaries

Beneficiary forms override your will. An ex-spouse, a deceased parent, or a blank line can send your retirement money to the wrong place — we check this in every review.

When to call

If any of these sound like you, it's time for a conversation.

You're within 5–10 years of retirement and want to stress-test the plan

Your kids are finishing college and you can finally accelerate retirement saving

You received an inheritance, sold a business, or had a windfall

You changed jobs at 55+ and have a 401(k) to roll over

A spouse's health changed and long-term care is suddenly real

Your term life insurance ends in the next 5–10 years

You just got married, divorced, remarried, or lost a spouse

Prepare for your meeting

A little prep makes a big difference.

You don't need every item below to start the conversation, but the more you bring, the more useful the meeting will be.

Questions to think about

How do I turn my 401(k) and savings into a paycheck I won't outlive?

When should my spouse and I claim Social Security to get the most out of it?

Do I still need life insurance once the kids are grown and the mortgage is smaller?

How much could long-term care cost my family — and how do I protect against it?

Am I saving in the right accounts for the tax bracket I'll be in later?

What documents and account info should I gather before we sit down?

Documents to gather

Recent 401(k), 403(b), IRA, and brokerage statements

Social Security estimate for you and your spouse (ssa.gov)

Mortgage balance, other debts, and average monthly household expenses

Current life insurance and any long-term care policy details

Beneficiary designations on retirement accounts and insurance

A short list of the goals that matter most — kids, home, travel, legacy

The Account Showdown

Two accounts. Same dollars in. Which would you pick?

11 quick rounds. Pick a winner each round. We'll keep score and reveal what each account actually is — with real-life scenarios.

11 quick roundsReal-life scenariosYour tally vs the real tally
Play the Showdown