Business Exit Planning: Selling Your Company Before You Retire
Selling your business in your 60s: valuation, asset vs stock sale taxes, installment notes and Medicare premiums, QSBS, ESOPs, health cover to 65, and a $4M S-corp worked example.
Financial Education
Guides for self-directed investors near or in retirement: Social Security, withdrawals, RMDs and Roth conversions, Medicare, long-term care, and your estate. Every guide cites its sources and uses current figures.
Start here. The decisions that matter most in the years before and after retirement, in roughly the order you will face them.
The 25x rule, safe withdrawal rates for a 30- or 35-year retirement, and how Social Security and pensions shrink the number you need.
How much claiming at 62, 67 or 70 changes your check, honest break-even math, survivor benefits, the earnings test and taxes.
Taxable, tax-deferred and Roth: the order to withdraw in, and when breaking it for Roth conversions, IRMAA and the 0% gains rate saves tax.
How to convert in the low-tax years between retirement and RMD age: how much each year with 2026 brackets, paying the tax, IRMAA, the five-year rules and heirs.
When to enroll, Medigap versus Medicare Advantage, and the income-based premium surcharges that catch retirees by surprise.
What care costs, the odds you'll need it, what Medicare and Medicaid pay, and how to choose between insurance and self-funding.
How each asset reaches your heirs, with a worked example of a couple's estate, 2026 federal and state estate taxes, beneficiary mistakes, trusts for grandchildren and an executor's first 90 days.
Who must empty an inherited IRA in 10 years, when annual RMDs apply under the final IRS rules, how inherited Roths differ, and how to plan your beneficiaries.
The annual exclusion, the $15 million exemption, 529 superfunding, paying tuition directly, and why some assets are better left than given.
Retirement and tax first, then investing, the home, insurance and the rest of the library.
Selling your business in your 60s: valuation, asset vs stock sale taxes, installment notes and Medicare premiums, QSBS, ESOPs, health cover to 65, and a $4M S-corp worked example.
How 401(k) loans work after 55: the $50,000 and 50% limits, what happens if you default or retire with a balance, the double-tax myth, and better ways to raise cash.
What each annuity type does, costs and hides: SPIAs, QLACs (2026 limit), MYGAs vs. CDs, index caps, variable fees, taxes, how sellers are paid, and a $300K example at 67.
Who qualifies on an ex's record, what you get at each age from 62, the 2-year rule, deemed filing, remarriage, survivor benefits after an ex dies, and how to apply.
What a widow or widower gets at each age, the survivor age table, the limit when a spouse claimed early, switching benefits, and a checklist for the first weeks.
Direct vs. 60-day rollovers, what you give up (rule of 55, creditor protection, the still-working RMD delay), RMD years, Roth and after-tax money, and when NUA on company stock pays.
How to judge a pension buyout: the return the annuity implies, PBGC protection, survivor options, inflation, and rollover taxes.
Selling the house in retirement: the $250K/$500K capital gains exclusion, moving costs, renting, aging in place and 2026 reverse mortgage limits.
Understand the key differences, tax implications, and strategies to help you choose the right IRA for your retirement goals.
How retirees fund a roof, a car, travel, gifts and IRMAA years from a cash bucket, and time IRA withdrawals so lumpy bills don't raise taxes or Medicare premiums.
2026 limits, catch-ups from 50 and the larger catch-up at 60 to 63, the Roth catch-up rule, and whether to fund a 401(k) or an IRA first.
The benchmarks that matter near retirement, how Social Security and pensions change your target, and what to do if you are behind.
How a rental sale is taxed in 2026 (recapture, capital gains, NIIT, IRMAA), vacation-home and passive-loss rules, and when to sell, 1031 exchange, sell in installments or hold for heirs' step-up.
How the 3.8% NIIT works: the $200,000 and $250,000 thresholds, what counts, why IRA withdrawals and Roth conversions can trigger it, and worked examples.
How Social Security, IRAs, pensions, annuities and dividends are taxed in 2026, the new senior deduction and IRMAA, a worked couple's return, and the levers that lower a retiree's tax bill.
How a DAF works for retirees: what to give, 2026 deduction limits and the new 0.5% floor, bunching past the 65+ standard deduction, DAF vs QCD vs private foundation, and a five-year example.
Give from your IRA at 70½ and up: how QCDs satisfy RMDs, stay out of taxable income, lower IRMAA, which charities qualify, and QCDs vs. appreciated stock.
The 0% capital-gains bracket, wash sales through an IRA, the $3,000 offset, carryforwards that die with you, and how harvested losses keep income under Medicare IRMAA tiers.
Learn how the Health Savings Account offers triple tax advantages and why experts call it the best retirement account available.
Medigap or Medicare Advantage at 65: 2026 costs side by side, networks and travel, Plan G vs. N, the six-month window, and why switching back later is hard.
Retired, widowed or divorced? How Form SSA-44 lowers your Medicare surcharge: what qualifies, what doesn't, the estimate, evidence and deadlines.
How to leave money to a child or grandchild on SSI and Medicaid: third-party vs first-party trusts, payback, what the trust can pay, IRAs under SECURE, ABLE accounts, and a $600,000 example.
IRS record-keeping periods, the records worth keeping for decades (basis, Form 8606, gift returns, pensions), a printable retention schedule, and the handover file your spouse or executor will need.
How a CRT turns low-basis stock or real estate into lifetime income: CRAT vs CRUT, the 10% and 5% tests, the deduction and its 30% AGI limit, payout taxes, and a $1.5M example.
A composite household, five calculators, and one honest verdict: what has to be true for a 60-year-old retirement to survive the bridge years before Medicare and Social Security.
Median net worth and retirement balances at every age from the Federal Reserve and Vanguard, the Fidelity multiples, and why Boomers, Gen X, Millennials, and Gen Z land where they do.
Fee-only vs fee-based, what a 1% fee really costs over 20 years, how to verify any advisor in 15 minutes, and the 10 questions to ask before you hire one.
Splitting a 401(k) by QDRO, IRAs, a pension and the house after 50, alimony and tax rules, Social Security, COBRA before Medicare, and a $2.4 million worked example.
How to provide for a second spouse and still leave your children an inheritance: QTIP trusts, 401(k) spousal consent, elective shares, IRAs, life insurance, the house, and a worked example.
Without a will an unmarried partner inherits nothing. Wills and trusts, beneficiary forms, titling, gift and estate tax without the marital deduction, inherited IRAs, Social Security and the house.
What belongs on a retiree balance sheet, gross vs. after-tax net worth, Federal Reserve medians by age, and the ratios that matter.
Leaving an adviser or taking over after a spouse: inventory, in-kind transfers, cutting costs, and a simple plan you can run yourself.
How compounding works on a large portfolio in the last working years and through retirement: the Rule of 72 on $1 million, what fees and inflation take, sequence risk and gifts to grandchildren.
Americans lost $8.6 billion to investment scams in 2025. Learn the 12 red flags, the math test that exposes fake returns, and how to verify any offer in 10 minutes.
Stock and bond ranges for the decade around retirement, with bucket strategies, sequence risk, glide paths, RMDs and rebalancing.
Investing an inheritance, rollover or home-sale proceeds: what the data says about investing at once vs. phasing in, and what matters more.
Why ETFs usually win in a taxable account and rarely matter in an IRA, how to move a portfolio from an adviser without a big tax bill, and taking RMDs in shares.
What AI tools can and cannot do for a self-directed investor: good uses, hallucination risk, privacy, and how to check an answer.
How a HECM works in 2026: who qualifies, what you can borrow by age, the real costs, the growing line of credit, the heirs' 95% rule, taxes and Medicaid, and when a HELOC is better.
The three housing choices retirees face, with carrying costs, the home sale exclusion, step-up at death and a worked example.
Survivor income, estate liquidity, term vs. permanent, and what to do with a policy you no longer need, including selling it.
One to two years of withdrawals, a reserve for big bills Medicare won't cover, where to hold it, and when to refill it.
When a loan beats selling shares or an IRA withdrawal, why a short bridge to the next tax year is the best debt a retiree can have, and the debts to clear or avoid.
Highest rate first saves the most, but near retirement the gap is small. Worked examples at 63 and 72, paying from savings or an IRA, and where the HELOC and mortgage fit.
Refinancing, a HELOC, insurance pricing and renting in a new city all still run on your credit. Keep old cards, freeze your files, and think twice about co-signing.
How the 50/30/20 split adapts to Social Security, pensions and withdrawals, how retirees really spend by age, and why guaranteed income covering essentials is the better test.
Free calculators for the same decisions, with the assumptions shown.
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