Phase 1: Wire, Pause, and Meet Your CPA
Days 1–30 — Protect your money before making any decisionsProtect the funds
Wire proceeds to a high-yield savings account
Move 100% of sale proceeds to an FDIC-insured HYSA (Ally, Marcus, Discover — currently 4.5-5.2% APY) or TreasuryDirect.gov for 6-month T-bills. Do not wire to a brokerage account. Do not invest on Day 1.
Do this in Week 1
Set aside your tax reserve in a dedicated account
Estimate 28-35% of the gain and park it separately. On a $3M sale with $2.2M gain, that's $616K-$770K reserved. Don't touch it. This is the number one mistake sellers make — they see $3M and spend $500K before tax season.
Estimate 30% of gain
Do not sign any investment advisory agreements
Cold calls from advisors spike after business sale closings. If you met someone at the closing, wait 60 days. Legitimate fee-only advisors don't cold call — they get referred through NAPFA.org or your attorney/CPA network.
90-day cooling period
Meet your advisory team
Schedule your CPA meeting within 14 days of closing
Bring: sale agreement, all proceeds documentation, your last 3 years of business and personal tax returns. Leave with: estimated tax liability, quarterly estimated payment schedule, guidance on installment sale treatment if applicable. Cost: $500-$2,500 for a focused post-exit planning session.
→ Model your after-tax number
Engage an estate attorney for beneficiary review
Post-sale asset levels often exceed what your existing will/trust was drafted for. Priority: update all account beneficiary designations (these supersede your will). Secondary: review healthcare directive and POA for post-exit risk levels.
Complete by Day 30
"The sellers who tell me they wish they'd done one thing differently usually say: 'I should have calculated my net-after-tax number before I started spending.' The CPA meeting in Week 2 is the most important 90 minutes of your post-exit life."
— Michael Chen, CFP\u00AE, RetireStack Reviewer
Phase 2: Build Your Income Floor
Days 31–60 — Convert proceeds into predictable, tax-efficient lifetime income$600K
minimum for income floor
50–60%
of net proceeds to income floor
$3,900
monthly from $600K SPIA at 65
The Income Floor Strategy
Your income floor is guaranteed monthly income that covers your non-discretionary expenses — housing, food, healthcare, insurance — regardless of market conditions. Here's how to build it in 60 days.
1
Calculate your guaranteed income sources. Add up Social Security (use SSA.gov to get your estimate), pension income, rental income, and any other fixed streams. Subtract this from your annual expenses. The gap is what your income floor must cover.
2
Allocate 50-60% of net after-tax proceeds to the income floor. Most of this goes to a Single Premium Immediate Annuity (SPIA) at age 65+. At June 2026 rates, $600K converts to approximately $3,600-$3,900/month guaranteed for life — with no market risk, no fees, and a life insurance benefit.
3
Shop carriers — rates vary 15-30% between insurers. Use Blueprint Income or ImmediateAnnuities.com to compare. Don't accept the first quote. A $500K SPIA at 5.5% vs 6.5% is $500/month difference for life — $120,000+ over 20 years.
4
Fill the rest with a 60/40 diversified portfolio — low-cost index funds (FXAIX, VTI) and Treasury/bond ladder. Dollar-cost average over 6 months to reduce sequence-of-returns risk. Target: total income floor covers 100% of essential expenses.
Healthcare and insurance
Enroll in COBRA or ACA marketplace within 60 days
COBRA: up to 18 months of your former business coverage, $600-$1,800/month for family. ACA: subsidies available if income is below ~$150K; enroll at HealthCare.gov within 60 days of losing coverage. Do not go uninsured — a health event without coverage in your 50s-60s is a retirement-ender.
60-day enrollment window
Review life insurance and disability coverage needs
Post-exit, your life insurance needs change. If you have a surviving spouse, update beneficiary designations. If you have term life, review whether converting to whole/universal makes sense now that you have permanent income. If you don't have long-term care insurance, explore a hybrid policy (linked benefit) — typically $2,000-$4,000/year for $100K+ LTC benefit.
→ Project LTC costs
Phase 3: Choose Your Advisor and Plan Your First Year
Days 61–90 — Lock in your strategy, find your team, and set your 12-month planChoose your financial advisor
Interview 2-3 fee-only CFPs from NAPFA.org
Look for CFPs who specifically list "post-business-exit planning" or "divorce settlement" as a specialty — these are the advisors who understand that your money came from a concentrated liquidity event, not decades of accumulation. A flat-fee comprehensive plan ($3,000-$15,000) is far better than a 1% AUM model ($30,000/year on a $3M portfolio). Ask: "What's your planning fee, not your management fee?"
Day 60+ before signing
Consider Social Security timing with your advisor
If you're 62-67, Social Security claiming decisions are among the highest-leverage financial decisions left. Delaying from 62 to 70 increases your benefit by 76-84% — $1,800/month vs. $3,200/month at the same age. A $1,400/month difference for life is worth approximately $420,000 in present value at age 65. Don't make this decision without running the numbers with your advisor first.
→ Optimize SS timing
Set your first-year plan
Build a 12-month spending and deployment calendar
Work with your advisor or use RetireStack's post-sale bridge calculator to build a 12-month deployment calendar. Map: month-by-month investment deployment (6-12 month DCA schedule), quarterly estimated tax payments (due April, June, September, January), major decisions (SPIA purchase, real estate purchase, charitable giving strategy). The goal is to start Day 91 with a written, reviewed plan — not a pile of money and good intentions.
→ Run the Post-Sale Bridge Calculator
Set your post-exit daily structure
Business owners often don't realize how much structure their business provided. The first 90 days are the highest-risk period for reactive spending (the house renovation, the new car, the vacation that's "well deserved"). Set a daily routine: exercise, financial review, one meaningful conversation per day. The money decisions made in calm times beat the ones made in euphoria.
Celebrate, then get back to the plan
You executed one of the most complex financial transactions of your life. Take 2 weeks to decompress, travel, reconnect with family. But set a hard date to return to the plan — typically 30-45 days post-close. By Day 90 you should have: tax reserve set aside, income floor strategy defined, healthcare enrolled, estate plan updated, and a fee-only advisor engaged. That's the foundation everything else is built on.
Frequently Asked Questions
The 90-day rule refers to the critical window after closing where sellers should avoid major financial commitments. Wire your proceeds to a high-yield savings account (currently 4.5-5.2% APY) or buy 6-month T-bills. Do not sign investment advisory agreements, make major purchases, or commit to recurring expenses. Use the time to: (1) meet with a CPA within 2 weeks, (2) calculate your true net-after-tax number, (3) review your estate plan. This is the window where sellers most often make expensive mistakes — a $2M wire sent to an investment advisor who charges 1% AUM costs you $20,000/year for life.
Start with your gross sale price and subtract in order: (1) broker commissions (typically 8-12% for businesses under $10M), (2) legal and advisory fees ($5,000-$25,000), (3) federal capital gains tax on the gain (20% long-term rate + 3.8% NIIT), (4) state capital gains tax. For example, on a $3M sale with $2.2M gain in a 5% state: net = $3M - $300K (broker) - $15K (legal) - $524K (federal NIIT) - $110K (state) = $2.051M. Use the Business Sale Retirement Calculator to model your specific situation.
Wait until Month 3 (Days 60-90) before deploying to a SPIA. By then you'll have your net-after-tax number confirmed by your CPA, your guaranteed income floor calculated, and your true income gap identified. At June 2026 rates, a $600K SPIA purchased at age 65 generates approximately $3,600-$3,900/month guaranteed for life. Never buy a SPIA with funds you may need for liquidity in the next 24 months.
Three options: (1) COBRA — up to 18 months of your former business plan, $600-$1,800/month for family. (2) ACA marketplace — subsidies may make this cheaper between ages 50-64; enroll at HealthCare.gov within 60 days. (3) Spouse's employer plan — often most cost-effective if available. Do not go uninsured. A health event without coverage in the first 90 days can destroy your retirement plan before it starts.
Yes — but wait until Day 60 before signing anything. Interview 2-3 NAPFA.org fee-only CFPs who specialize in post-business-exit planning. Flat-fee engagements ($3,000-$15,000 for a full plan) are better than AUM models (1% = $30,000/year on a $3M portfolio). Avoid any advisor who cold calls you or claims to have a special product for business sellers within the first 90 days.
Every account beneficiary designation must be reviewed — these supersede your will. Update all bank and brokerage account beneficiaries to match your trust/will. Review life insurance beneficiaries. Consider a spousal lifetime access trust (SLAT) if you live in a high-estate-tax state. A simple will update runs $300-$800; a comprehensive post-exit estate plan with trust runs $2,000-$8,000. Do this in Month 2.