Blog
The Talley Perspective
Straightforward thinking on taxes, retirement, investment decisions, and building a financial life that actually works.
Featured / Tax Planning
Is an S Corp Worth It in Tennessee?
The S corp advice you've heard was probably written for another state. In Tennessee the payroll-tax savings are real, the excise tax quietly offsets them, and the answer lives in a band with a bottom and a top.
All Articles
Use these as decision support, not market noise.
Browse by planning area
Retirement decisions
Income, timing, taxes, healthcare, and market risk near retirement.
Browse by planning area
Tax-aware planning
Roth conversions, RMDs, entity choices, and tax timing questions.
Browse by planning area
Investment questions
Portfolio decisions connected to actual goals rather than market noise.
Browse by planning area
Business owner planning
Owner compensation, business cash flow, taxes, and personal planning overlap.
Tax Planning
Should a Business Owner Take the Tax Deduction or Go Roth?
A deduction isn't automatically a win. For a surprising number of business owners, taking it is the expensive choice, and the trajectory of your wealth is what tells you which side you're on.
Tax Planning
Should I Buy a Truck in December to Lower My Taxes?
The write-off is real. The math almost never is. What a $90,000 truck actually does to your taxes, and what to buy instead if the deduction is the thing you're after.
Tax Planning
Can I Really Put My Kids on the Payroll?
Paying your kids through the business is one of the few internet tax ideas that's actually real. The savings are smaller than the videos promise, bigger than most owners realize, and the best part isn't the taxes at all.
Tax Planning
Why Doesn't My CPA Help Me Lower My Taxes?
If your CPA files a clean return every year and has never once suggested a strategy, there's a reason. It's not laziness. It's the lens the job puts on them.
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.
Investing Behavior
Should I Pay Off the Mortgage or Invest? The Math Is Simple Until It Isn't
The rule is interest rate arbitrage, and most of the time it holds. Here is where it breaks, and the couch analogy that explains why debt sometimes buys you more than it costs.
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.
Business Owner Planning
Cash Is Piling Up in the Business Account. What Should I Do With It?
The hoarding instinct is right early and expensive later. Here is how to calculate the reserve you can actually justify, and what one owner's idle cash was costing every month.
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.
Tax Planning
Should I Do Roth Conversions? The Question Is Dosage
Most people who do Roth conversions do not do enough of them. Here is a plain-English way to think about the right dose, and the short window where it tends to matter most.
Tax Planning
The Widow's Tax: Why Couples Plan Together for the Day Only One of Them Is Here
After the first spouse passes, the survivor is often pushed onto higher single-filer brackets on nearly the same income. Here is what that is, why it happens, and why couples tend to plan for it now, together, with more warmth than worry.
Investing Behavior
The Market Dropped. Should I Change My Plan?
When the headlines get loud and your account is down, the instinct is to do something. Here is a plain-English look at why a good plan is built to survive exactly these stretches, and why zooming out is usually the wisest move you can make.
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.
Estate and Legacy
Inherited an IRA? The 10-Year Rule and the Beneficiary-Designation Trap
An inherited IRA is a tax bill on a timer. Here is why planning unequal withdrawals around your own higher and lower income years usually beats both a lump in year ten and ten equal installments, and the quiet trap that a beneficiary form can override your will.
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
Moving to Tennessee for the Taxes: What a Retiree Actually Saves
Everyone moving here has heard that Tennessee has no income tax. That part is true. Counting what it is actually worth means looking at what your old state was already doing, and at one year that matters more than the rate.
Financial Planning
CFP vs CPA: Which One Does Your Situation Need?
The comparison most people are really making is CFP versus CPA. Here is what each one is licensed to do, where the EA and CFA fit, and how to read the rest of the letters on a business card.
Tax Planning
Year-Round Tax Planning in Johnson City
Filing records decisions after they are final. Planning happens while you can still change them. Who around here actually needs the second service, and what it looks like in practice.
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.
Business Owner Planning
When Should You Upgrade Your Business Tax Strategy?
The tax playbook for a thriving business is never the same as the one you started with.
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.
Tax Planning
Should I Elect S-Corp Status?
The S-Corp question is not just entity trivia. It is a question about owner pay, payroll taxes, Tennessee rules, cash flow, and whether the added complexity is actually worth it.
Tax Planning
The Roth Conversion Checkbox Problem
Most people doing Roth conversions are barely doing them. The box feels checked. The lifetime math says otherwise.
Tax Planning
The Tax Strategy Gap
Many people with meaningful tax bills cannot name the strategy behind them. Here is what that gap looks like and why closing it matters.
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.
Tax Planning
What Real Tax Planning Looks Like
Tax planning is not just March paperwork. Real planning coordinates income, investments, Roth conversions, and timing before the tax year is over.
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.
Tax Planning
Tax Planning for High-Income W-2 Earners
High-income W-2 earners still have meaningful tax-planning options. Here are the moves most worth reviewing before year-end.
More resources
Different formats for different questions.
Planning tools
Use the calculators and visual tools when you want to see the concept, not only read about it.
ExploreLearning Center
Short answer-first explainers for retirement, tax, investing, and planning questions.
ExploreRetirement guide
A practical framework for retirement timing, taxes, income, and market risk.
Explore