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Straightforward thinking on taxes, retirement, investment decisions, and building a financial life that actually works.
Retirement Planning Articles
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Retirement Planning
What Happens to Company Stock in My 401(k) When I Retire?
Company stock inside a workplace plan follows a different set of tax rules than everything else in the account, and those rules only stay available if you handle the stock before you move the account.
Retirement Planning
Can I Take Money Out of My 401(k) at 55 Without the Penalty?
Often yes, thanks to a provision usually called the rule of 55. The two things people get backwards are which account it applies to, and how easy it is to cancel by accident.
Retirement Planning
What will my life actually look like when I retire?
The math matters, and it's only half the plan. The other half is what your days are actually for once the career chapter closes.
Retirement Planning
Am I Behind? Behind on What, and Compared to Whom?
The question has two holes in it. Until you say what you are behind on and who you are measuring against, there is nothing there to answer. Here is how to turn the feeling into arithmetic.
Retirement Planning
Turning Your Savings Into a Retirement Paycheck: A Simple Way to Think About Running Out
The question we hear most is "will I run out of money?" Here is a plain-English way we help people turn a lifetime of savings into a paycheck that can weather a bad market.
Retirement Planning
Social Security: When Should I Claim, and Will It Even Be There?
Two fears usually ride together here: that the program will vanish, and that you will pick the wrong year to turn it on. Here is the straight answer to the first, and a plain way to think about the second.
Retirement Planning
Health Insurance If You Retire Before 65: The Bridge to Medicare and the Subsidy Cliff
For a lot of people the real thing standing between them and retiring is not the portfolio. It is health insurance before Medicare kicks in. Here is how that gap works, and why the premium is partly a planning decision.
Retirement Planning
Pension: Lump Sum or Monthly Payments? How to Think About a One-Way Decision
It is one of the biggest financial decisions many people ever make, it usually cannot be undone, and the internet is full of confident answers that ignore your actual life. Here is a plain way to think it through.
Retirement Planning
Which Account Do I Spend First in Retirement? Withdrawal Order in Plain English
There is a famous rule of thumb for which account to draw from first. It is a fine starting point and a poor finish line. Here is why the order depends on you, and the house rules worth knowing.
Business Owner Planning
How Do I Get Wealth Out of My Business (and Into Retirement)?
For a lot of successful owners the business is the retirement account, but the wealth is trapped inside it. Here is a plain-English way to think about moving wealth out of the business and framing the sale as your retirement event.
Retirement Planning
Is the Annuity or Whole-Life Policy I Was Sold Actually Right for Me? An Honest Second Opinion
An honest second opinion. Some of these products do a real job well. Many were sold for the commission and duplicate a job your plan already covers. Here is how to read what you actually own.
Retirement Planning
Can I Afford to Spend More in Retirement? The Upper Guardrail
For a lot of careful savers the real risk is not running out. It is passing away with far more than you needed, having skipped things you could easily have afforded. Here is the case for an upper guardrail.
Tax Planning
Do I Pay State Taxes on Retirement Income in Tennessee?
The short answer is no. The useful answer is knowing where taxes still show up for a Tennessee retiree, and why the missing state layer makes the remaining planning even more valuable.
Retirement Planning
What should I do with my 401(k) when I retire?
Rolling to an IRA or staying in the plan is the part everyone asks about, and it is usually the least important of the three decisions hiding inside this question. Here is how to take them one at a time.
Financial Planning
Should I Get a Second Opinion on My Retirement Plan?
When it is worth getting, what an honest one covers, and the one test that separates a real review from a sales pitch: it has to be able to end with stay where you are.
Retirement Planning
The Five Years Before Retirement: What Has to Happen, and In What Order?
The five years before the last paycheck decide more than the thirty before them. Here is what has to happen in that window, in order, and what an advisor is actually for during it.
Retirement Planning
Health Insurance Options Before Age 65
If you want to retire before Medicare, health insurance is usually the first real obstacle. Here are the main options and the planning traps that matter.
Retirement Planning
What's Your Retirement Number Based On?
Most people approaching retirement have a number in mind. Almost none of them have a plan that produced it.
Retirement Planning
The Retirement Risk Nobody Talks About
Retirement risk is not only market decline. Sequence, timing, withdrawals, and tax decisions can reshape the plan just as much.
Retirement Planning
What Changes as Financial Independence Gets Closer
As financial independence gets closer, growth stops being the only goal. Coordination, tax timing, and risk control start to matter more.
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