Planning guides
Guides to the decisions that shape a retirement
Each guide opens with the short answer, shows the arithmetic, and cites the primary source. Figures are current for 2026.
Tax Planning
Brackets, deductions, the 0% gains line, and the order in which accounts are drawn down.
Tax Planning · 8 min readThe 0% Capital Gains Bracket in 2026: Where It Ends and How Gains Stack on TopIn 2026, long-term gains are taxed at 0% up to $98,900 of taxable income for joint filers ($49,450 single). How the stacking works, with worked examples.
Tax Planning · 8 min readThe $11,250 Super Catch-Up: How Ages 60 to 63 Get the Largest 401(k) Allowance in 2026The 2026 401(k) limit is $24,500. Savers who turn 60 to 63 this year can add an $11,250 catch-up, for $35,750. The table, the Roth rule, a worked example.
Tax Planning · 8 min readWhere the 12% Bracket Ends in 2026: $100,800 for Married Couples Filing JointlyFor 2026, the 12% bracket for joint filers ends at $100,800 of taxable income, about $133,000 gross. How to measure the room below it, with worked math.
Tax Planning · 9 min readThe 2026 Standard Deduction for Retired Couples: $32,200 and the Layers Above ItThe 2026 standard deduction for joint filers is $32,200, and up to $47,500 for a couple both 65 or older. How it sits beneath the 10% and 12% brackets.
Tax Planning · 9 min readThe $6,000 Senior Deduction: What It Is Worth, Where It Phases Out, and What It Leaves AloneThe $6,000 senior deduction (2025 to 2028) lowers taxable income at 65+, but Social Security is taxed as before. Phase-out math and three worked examples.
Tax Planning · 9 min readStep-Up in Basis: What Resets at Death, What Does Not, and Why the Difference MattersInherited assets take a cost basis equal to their value at death, but IRAs never step up and gifts keep the giver's basis. The rules and a worked example.
Tax Planning · 9 min readTax Withdrawal Sequencing: Why the Order You Draw Down Accounts Is a Tax DecisionWhich account funds retirement spending can move the same dollar from a 12% to a 22%+ rate. 2026 brackets, the tax torpedo, QCDs and a worked example.
Tax Planning · 6 min readDo Taxes Really Get Simpler in Retirement?Many households expect an easier tax picture once the paycheck stops. For those who saved well in pre-tax accounts, the opposite is often true.
Tax Planning · 7 min readThe Window Before Required WithdrawalsBetween the last paycheck and age 73, much of a household's taxable income is chosen, not imposed. The four decisions in that window, and how we sequence them.Tax Planning · 7 min readWhen Avoiding a Tax Bill Costs More Than the TaxOn a $500,000 long-term gain, the 2026 federal tax is a known number. The risk in one stock is not. The math, the middle paths, and when holding is right.RMDs
Required distributions, the first-year deadlines, inherited accounts, and charitable moves.
RMDs · 8 min readYour First RMD Has Two Deadlines: How the April 1 Delay Works, and When It Costs MoreTurning 73 in 2026? The first RMD is due December 31, 2026 or, once, April 1, 2027. Delaying puts two RMDs in one tax year. Worked numbers for both paths.
RMDs · 9 min readThe Inherited IRA 10-Year Rule: Who Is on the Clock, and How the Withdrawals Can Be PacedMost non-spouse heirs must empty an inherited IRA by the end of year 10, and many owe annual RMDs since 2025. Who is covered and a worked example.
RMDs · 8 min readThe Missed RMD Penalty: What It Costs and How to Correct ItMissing a required minimum distribution triggers a 25% excise tax on the shortfall, cut to 10% if corrected in time. How the deadlines and Form 5329 work.
RMDs · 11 min readQualified Charitable Distributions in 2026: How Up to $111,000 Can Satisfy an RMD Without Adding to IncomeA qualified charitable distribution of up to $111,000 in 2026 can satisfy an RMD without adding to taxable income. The rules, the math and the pitfalls.
RMDs · 10 min readRequired Minimum Distributions in 2026: Starting Ages, the Calculation and the Account RulesRequired minimum distributions in 2026: when they start (73 or 75), how each amount is figured, which accounts can be combined, the penalty, and QCDs.
RMDs · 10 min readRoth 401(k)s No Longer Have RMDs: What Changed and the Five-Year Clock That Still MattersSince 2024, Roth 401(k)s have no lifetime RMDs. How they compare with a Roth IRA now, the five-year clock a rollover can reset, and 2026 limits.Roth Conversions
When conversions pay off, how to time them, and the five-year clocks.
Roth Conversions · 11 min readRoth Conversions: When They Pay Off, and How to Size and Time ThemWhen a Roth conversion pays off: the tax-rate test, the pre-RMD window, 2026 brackets and IRMAA cliffs, heirs, and a worked example of sizing a conversion.
Roth Conversions · 12 min readThe Two Roth Five-Year Clocks: What Each One Governs and When It Stops MatteringRoth IRAs run two five-year clocks: one per person for tax-free earnings, one per conversion for the 10% penalty. What each governs, with a worked example.Medicare
Part B costs, the IRMAA surcharge cliffs, and the enrollment window.
Medicare · 9 min readThe IRMAA Cliff: One Dollar Over $218,000 Can Add About $2,300 a Year to a Couple’s Medicare PremiumsThe IRMAA cliff: one dollar over $218,000 of joint MAGI adds about $2,300 to a couple's 2026 Medicare premiums. The math, the tiers and the look-back.
Medicare · 11 min readMedicare’s 7-Month Enrollment Window: The Dates, the Exceptions and the Lifetime Part B PenaltyMedicare's 7-month window surrounds your 65th birthday. Miss it without qualifying coverage and Part B costs 10% more per year of delay, for life.
Medicare · 12 min readMedicare and IRMAA in 2026: The Four Parts, the Income Tiers and the Two-Year Look-BackMedicare's four parts in 2026, the IRMAA tiers that raise Part B and D premiums above $109,000 or $218,000 of income, and how the two-year look-back works.
Medicare · 9 min readMedicare Part B Costs in 2026: The $202.90 Premium, the $283 Deductible and What Reaches Your CheckMedicare Part B costs $202.90 a month in 2026, up $17.90, with a $283 deductible. What that does to a 2.8% COLA, who is protected, and who pays more.Income Planning
How much is enough, withdrawal rates, and early access to retirement accounts.
Income Planning · 8 min readIs the 4% Rule Dead? Why the 2026 Research Lands Between 3.9% and 4.7%Is the 4% rule dead? Morningstar says 3.9% for 2026 retirees; Bengen's update says 4.7%. Why they differ, a worked example, and what moves the rate.
Income Planning · 8 min readHow Much Do You Need to Retire? The ×25 Estimate, Built From the Right InputA first-pass retirement number: 25 times the spending your portfolio must cover. The research range (×21.3 to ×25.6), a worked example, and its limits.
Income Planning · 11 min readRetirement Income and Withdrawal Rates: From One Number to a Coordinated PlanWhat the 2026 research says about safe withdrawal rates, why the first years matter most, and how we coordinate income with taxes and Social Security.
Income Planning · 10 min readThe Rule of 55: Penalty-Free 401(k) Withdrawals After Leaving Work at 55Leave an employer in or after the year you turn 55 and its 401(k) avoids the 10% early-withdrawal tax. What qualifies, the rollover trap, an example.
Income Planning · 7 min readCan We Retire at 65? The Five Decisions That Answer ItRetiring at 65 turns on five decisions, not the balance: coverage until Medicare, when to claim, which account first, flexible spending, the first five years.
Income Planning · 6 min readThe Two Halves of a Retirement PaycheckFixed bills deserve income that arrives on a schedule. How we match reliable income to the bills, let the rest flex, and where alternative income fits.
Income Planning · 5 min readWhen Inflation Comes Back: What a Century of Data Says About Your Retirement PlanInflation ran above 5% in 26 of the last 112 years. What a century of data says about inflation and retirement, and how a plan can prepare.
Income Planning · 5 min readWhen the Fed Pauses: Cash, Bonds, and the Rate You Lock InFive of the last six Fed pauses ended in cuts, yet long rates fell after only half. What that means for cash, bonds and the rate you lock in.Family Wealth
Preparing the people who will inherit, not just the documents.
Family Wealth · 6 min readIs Your Family Ready for What You Leave Them?The documents are the manageable part of passing on wealth. Most of what goes wrong traces back to preparation and conversation, not tax structure.
Family Wealth · 7 min readThe Documents That Override Your WillRetirement accounts, life insurance, and transfer-on-death accounts pass by the form, not the will. What the courts decided, and how we keep forms aligned.Life Transitions
The first year after a death, a divorce, or a retirement date: what changes, and in what order.
Life Transitions · 6 min readDividing Retirement Accounts in a DivorceA 401(k), a pension, and an IRA each split under a different rule than the house. Moved the right way, the split is not taxed. Moved the wrong way, it is.
Life Transitions · 7 min readThe First Year After a Spouse Dies: What Can Wait, and What CannotMost decisions after a spouse dies can wait a year. The last joint return cannot: what the year of death allows, what filing single changes, and the real dates.Portfolio Structure
Concentration, diversification, and what each holding is for.
Portfolio Structure · 6 min readHow Many Funds Does a Portfolio Need?Fourteen funds can still be one bet. What diversification actually spreads, the top-ten test you can run on a statement, and how we think about structure.Portfolio Structure · 7 min readWhat a Concentrated Stock Position Is ForAbout 4 in 100 companies produced all of the stock market's net gains from 1926 to 2016. What a large position in one stock is for, and how to size it.
Portfolio Structure · 6 min readOil in a Portfolio: 125 Years of Booms, Busts, and What They TeachOil has made and erased fortunes for 125 years. What the price history says about owning it, how it moves with inflation and stocks, and how to size it.Equity Compensation
RSUs, options, and the tax mechanics of a paycheck paid in stock.
Equity Compensation · 21 min readApple ESPP: Lookback, Taxes, and When to SellApple's ESPP: the six-month lookback, purchase dates against the blackout calendar, the 2026 tax on each kind of sale, and California vs Texas.
Equity Compensation · 19 min readApple RSUs: Vesting, Blackouts, and the Tax at Each VestApple RSUs: what the filed award agreement says about leaving, leave and death, the 22% withholding gap at vest, blackouts, and California vs Texas.
Equity Compensation · 19 min readESPP: Sell Right Away or Hold? The 2026 Tax RulesSelling ESPP shares at purchase locks in the discount; a qualifying disposition saves less tax than expected. Four-exit table, 1099-B trap, California.
Equity Compensation · 18 min readGoogle GSUs: Vesting, Withholding and What to Do at VestGoogle GSUs: vesting set by your grant, Class C shares delivered net of 22% and 10.23% withholding, the tax gap that leaves, and what to do at each vest.
Equity Compensation · 21 min readMeta RSU Vesting Schedule, Refreshers and Tax at Each VestMeta RSUs vest 1/16th a quarter on Feb, May, Aug and Nov 15, just before trading closes. Refreshers, the tax at each vest, layoffs, leaving California.
Equity Compensation · 18 min readMeta vs Tesla Equity Compensation: How to Compare the OffersMeta and Tesla equity side by side: RSU vesting, ESPP, 401(k) match, trading windows, hedging bans, and a Menlo Park vs Austin after-tax example.Equity Compensation · 18 min readNVIDIA ESPP: The 24-Month Lookback, Reset and TaxesNVIDIA's ESPP runs 24-month offerings with a lookback and a reset. The purchase price, the $25,000 cap, the tax on selling, and the closed-window rule.
Equity Compensation · 15 min readNVIDIA RSUs: Vesting, Leaving, and the Tax at Each VestHow NVIDIA RSUs vest, what happens if you leave or die, what 22% and 10.23% withholding miss, the 1099-B basis trap, and selling inside closed windows.
Equity Compensation · 19 min readRSU Withholding: Why 22% Falls Short in 2026RSUs are wages at vest, withheld at a flat 22% while 2026 brackets run to 37%. The California layer, sell-to-cover, the 1099-B trap and the safe harbors.
Equity Compensation · 17 min readTesla ESPP: Lookback, Offering Periods and When to SellTesla's ESPP buys at 85% of the lower of two prices six months apart. The lookback, the $25,000 cap, qualifying dates by lot, and California vs Texas tax.Equity Compensation · 20 min readAT&T RSU Vesting, Performance Shares and the SPDPHow AT&T RSUs and performance shares vest, what retirement does to each, and how the Stock Purchase and Deferral Plan’s 20% match works, from the filings.
Equity Compensation · 22 min readChevron RSUs and Performance Shares: Vesting and LeavingHow Chevron RSUs, performance shares and legacy options vest, the 55-and-10 and points rules when you leave or retire, and the tax at each vest.
Equity Compensation · 15 min readExxonMobil Restricted Stock: Vesting, Retirement and TaxExxonMobil restricted stock vests 50% at 3 years and 50% at 7, keeps releasing after retirement, and is forfeited before 65 unless retention is approved.Equity Compensation · 24 min readLockheed Martin RSUs: The 3-Year Cliff and Retirement RulesHow Lockheed Martin RSUs, PSUs and LTIP vest, the 55-with-10 retirement test as filed, layoff vs. leaving, 37% withholding, the DMICP and the 1099-B trap.
Equity Compensation · 14 min readRule 10b5-1 Plans for Employees, Not Just ExecutivesWhat a Rule 10b5-1 plan is, the SEC's 2022 cooling-off and overlap rules, what Nvidia, Apple, Alphabet and Meta policies add, and a setup checklist.
Equity Compensation · 12 min readThe 83(b) Election: The 30-Day Deadline and When to FileAn 83(b) election taxes restricted stock or early-exercised options at grant, not at vest. The 30-day deadline has no extension. How to file, when not to.
Equity Compensation · 19 min readCalifornia to Texas Before a Liquidity Event: The Tax RulesCalifornia keeps taxing equity earned there after you move to Texas: RSUs by workdays grant to vest, NSOs to exercise. Residency, timing, a worked example.
Equity Compensation · 15 min readDiversifying Concentrated Stock After an IPOCheck your insider trading policy first. Then compare staged sales, exchange funds, prepaid forwards, collars, charitable gifts and direct indexing.
Equity Compensation · 17 min readIPO Lockup Expiration: What to Do Before ReleaseAn IPO lockup is a contract, usually 90 to 180 days, set out in the prospectus. How to read yours, why release is not an open window, and what to prepare.
Equity Compensation · 12 min readExercising ISOs Before an IPO: AMT in 20262026 AMT: a $140,200 joint exemption phased out from $1,000,000 at 50 cents per dollar. A worked ISO exercise, the credit, and the California layer.
Equity Compensation · 13 min readPre-IPO Stock Options: ISOs vs NSOsHow ISOs and NSOs are taxed at grant, exercise and sale, the $100,000 ISO limit, the exercise window after leaving, and the California layer.
Equity Compensation · 12 min readQSBS and California: The Exclusion California Doesn't FollowSection 1202 can exclude up to $15M of gain federally; California doesn't conform. The 2025 tiers, and why late-stage employee stock rarely qualifies.
Equity Compensation · 14 min readCompany Tender Offer: Should I Sell? A Decision WorksheetA tender offer stays open at least 20 business days. How the buyer, price and each lot's tax character shape the call, plus a how-much-to-sell worksheet.
Equity Compensation · 12 min readSpaceX Lockup Expiration Dates: The SPCX Release CalendarSpaceX lockup expiration comes in stages: up to 7% on Oct 9 and Oct 24, 28% after Q3 results, the rest Dec 8, 2026. Every date, and what to do before each.Business Owners
The decisions that exist only before a sale, and the plan for the proceeds.
Real Estate
Rental property exits, depreciation recapture, and the step-up at death.
Private Markets
What accredited means, and how a private investment earns a place.
Working With Us
How our fee is set, what fee-only means, and who watches the whole picture.
Working With Us · 6 min readWhat Fee-Only Means, and What It Does NotFee-only means paid by the client and by no one else. What the term covers, what it leaves out, how our fee is disclosed, and five questions to ask any advisor.
Working With Us · 6 min readWho Watches the Whole Picture?A CPA, an estate attorney, maybe an advisor. Each was hired for a part. Three situations where the decisions fall between them, and what coordination is.
Social Security
Claiming ages, spousal and survivor rules, and how the benefit interacts with taxes.