The Steward's Desk
Plain-language answers to the money questions people actually ask
Articles on the decisions I help clients make every week: retirement income, Social Security, taxes, investing, insurance, and what to do when life hands you something new. Each service page collects its related reading, or browse everything below.
All articles
Plain-language writing on retirement income, Social Security, taxes, investing, insurance, and estate planning. New pieces land here as I write them.
How much should you keep in an emergency fund?
How many months of spending you actually need, and what makes your number bigger or smaller.
How to save more without tracking every dollar
A goal-funding system that runs on automation instead of willpower and spreadsheets.
The behavior gap: why investors trail their own funds
Morningstar keeps finding that investors trail the very funds they own. Where the gap comes from, and what closes it.
Index funds vs. stock picking: what the evidence shows
What long-run evidence says about active picking, costs, and the odds you're accepting.
What order should you withdraw from retirement accounts?
Why the taxable-first default exists, when it costs you money, and how a tuned order works.
Sequence-of-returns risk: why the first years of retirement carry so much weight
Two retirees, same average return, different outcomes. Why the early years count double.
Tax planning vs. tax preparation: what's the difference?
Your CPA looks backward at last year. Planning looks ahead at the next twenty.
What is a Roth conversion, and when does it make sense?
Paying some tax now to skip more later: the mechanism, the window, and the side effects.
Term or whole life: which insurance fits your family?
An honest comparison of cost, duration, and cash value, with a verdict that depends on your situation.
Disability insurance: the coverage high earners skip
Your income supports everything else in the plan. What group coverage misses, and how to check yours.
Will versus trust: what each one actually does
What each document does, what probate really involves, and who needs which.
Why your beneficiary forms outrank your will
Five account types where a form on file, not your will, decides who inherits.
When should you claim Social Security?
Health, other income, and your spouse's benefit all move the answer. How to think it through.
How Social Security spousal benefits work
Claiming on a spouse's record, including after divorce: who qualifies and for how much.
How to cover health insurance before Medicare
COBRA, the marketplace, or a spouse's plan: how to bridge the years before 65.
How Medicare's IRMAA surcharge actually works
The two-year lookback that sets your premiums, and the planning levers that manage it.
How do RSUs work, and when are they taxed?
Vesting, taxes, and the sell-or-hold question, answered in plain terms.
What does a 529 cover, and what if it goes unused?
What counts as qualified, and the options if your child takes a different path.
Should you save for college or retirement first?
The order of operations when you can't fully fund both at once.
How does a donor-advised fund actually work?
Contribute now, grant over time: how DAFs work and when they're worth the setup.
What is a qualified charitable distribution?
Giving straight from your IRA after 70 1/2, and how it counts toward your RMD without counting as income.
When should you start planning your business exit?
What to start five years out, three years out, and in the final year before a sale.
What should you do after selling your business?
The identity shift, the cash question, and a calm order of operations for the proceeds.
What should you do in the first year after an inheritance?
Very little needs to happen right away. What can wait, and what actually has deadlines.
How does the inherited IRA 10-year rule work?
The clock, the exceptions, and why spreading withdrawals across the window is a tax decision.
Should you pay off your mortgage early?
The math view and the sleep view, both taken seriously.
Debt avalanche vs. snowball: which should you use?
One wins the arithmetic, the other wins follow-through. How to pick, or blend the two.
A quick, useful starting point
7 Financial blind spots of high earners
The checklist version of what these articles keep circling: the spots where careful, successful people still get surprised.
Reading is a good start. A conversation goes further.
If an article raised a question about your own situation, bring it to a short call. We'll look at your specifics together.
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Common questions
What do these articles cover?
The same topics I plan around with clients: retirement income, Social Security timing, tax planning, investing, insurance, estate basics, and situational ones like equity compensation, inheritances, and business exits. Every article aims at a question people actually type into a search bar, answered in plain language.
Who writes these articles?
I do. Jesse Plunkett, CEPA, CRPC, the advisor behind True Stewards Advisory. Each piece reflects how I actually plan with clients, not ghostwritten filler. You can read my background on the Meet Your Advisor page or look me up on 
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Is this personal financial advice?
No. Articles are educational and general by design. Your situation has specifics no article can see: your accounts, your taxes, your family, your timing. If something here raises a question about your own plan, a short call is the right place to take it.
Do you work with clients in my state?
Almost always. Everything is handled virtually, so where you live is rarely a barrier. The only exception is a handful of states where I'm not registered yet, and if that's you, I'll tell you on our first call.