Got married

Within 30 days

• □ Update beneficiary designations on 401(k), IRA, life insurance, and bank accounts (POD designation).
• □ Decide on bank account structure (fully joint / fully separate / yours-mine-ours). See Money and Marriage.
• □ Review both credit reports together at annualcreditreport.com ↗.
• □ Update emergency contacts at employer and doctor.

Within 90 days

• □ Update health insurance (marriage is a qualifying life event).
• □ Add spouse to auto insurance.
• □ Review auto, renter, or homeowner insurance.
• □ If one spouse has significantly higher income, review tax withholding.
• □ Get a will if you have significant assets, a child, or a specific distribution preference.

Bitcoin holders

• □ Does your spouse know about your Bitcoin?
• □ Do they know how to access it if something happens to you?
• □ Is your inheritance plan documented? See Inheritance.

Had a baby

Before leaving the hospital

• □ Social Security number application (hospital usually provides form).

Within 30 days

• □ Add baby to health insurance. You have 30 days. Miss this window and you may have to wait until open enrollment 🔍 verify×DON'T TRUST, VERIFYClaim: Birth triggers a 30-60 day Special Enrollment Period for health insurance.Verify at: HealthCare.gov SEP ↗Employer plans vary. Check your specific plan..
• □ Update beneficiary designations.
• □ Get a will. A will specifies guardianship. Without it, courts decide.

Within 90 days

• □ Term life insurance review. 10x income rule of thumb.
• □ Disability insurance check. Your income just became more critical to protect.
• □ Open a 529 college savings account. Even $25/month at birth compounds to approximately $17,000 by age 18 at 7%.
• □ Update your emergency fund target. A baby changes monthly costs.

Changed jobs

Before your last day

• □ Download all pay stubs, W-2s, and tax documents.
• □ Get the summary plan description for your 401(k).
• □ Check your unvested 401(k) match. Leaving before vesting means leaving unvested employer contributions.
• □ Note your health insurance end date.

Within 30 days

• □ Roll over your old 401(k). Options: new employer plan, IRA at Fidelity, or leave it. Never cash it out. See 401(k) Rollover.
• □ COBRA or new employer health insurance decision. You have 60 days for COBRA election 🔍 verify×DON'T TRUST, VERIFYClaim: COBRA election window is 60 days from loss of coverage.Verify at: DOL COBRA ↗Standard federal rule; state mini-COBRA may differ..
• □ Update income withholding on W-4 at new employer.
• □ Enroll in new 401(k). If new employer has a match, do this day one.

Lost a parent

First week

• □ Locate the will and estate documents.
• □ Locate life insurance policies.
• □ Notify Social Security if parent received SS benefits.
• □ Secure the home and valuables.
• □ Do not immediately distribute assets. Wait for legal guidance.

Within 30 days

• □ Obtain multiple certified copies of the death certificate.
• □ Open probate if required (varies by state).
• □ File death claims on life insurance (30-60 day process).
• □ Notify all financial institutions.
• □ Inventory all accounts: bank, brokerage, retirement, digital.

Bitcoin-specific if parent held Bitcoin

• □ Is there a seed phrase in a safe or estate documents?
• □ Did they use a hardware wallet? Where is it?
• □ Did they leave instructions?
• □ If no seed phrase is found, the Bitcoin may be inaccessible. This is why inheritance planning matters.

Within 90 days

• □ Stepped-up basis opportunity. Inherited assets receive a stepped-up cost basis to fair market value at date of death.
• □ Required Minimum Distributions on inherited retirement accounts (SECURE Act 10-year rule for most non-spouse beneficiaries) 🔍 verify×DON'T TRUST, VERIFYClaim: SECURE Act imposes a 10-year distribution rule for most non-spouse inherited IRA beneficiaries.Verify at: IRS inherited IRA rules ↗Exceptions exist for spouses, minor children, disabled, chronically ill, and those within 10 years of decedent's age..
• □ Update your own estate documents.

Inherited money

After 90 days

• □ Determine the tax basis of inherited assets (stepped-up basis).
• □ Understand the source. IRA or 401(k) inheritance has different rules than regular investment account.
• □ Apply the order of operations. See What to Do With $X.
• □ If over $100,000, consult a fee-only fiduciary advisor at napfa.org ↗ before allocating.

Starting Medicare

6 months before you turn 65

• □ Research Medicare coverage options. Original Medicare vs Medicare Advantage. See Medicare Cost Estimator.
• □ Get your Medicare card. Enrollment begins 3 months before your 65th birthday.
• □ Note your employer coverage status. If you have employer coverage, Medicare rules differ.
• □ Part D drug coverage enrollment. Late enrollment penalty if you miss the window.

Starting a business

Before you start

• □ Business entity selection. Sole proprietor / LLC / S-Corp. Tax implications differ significantly. Consult a CPA.
• □ Separate business banking. Do not mix personal and business funds.
• □ EIN (Employer Identification Number). Free at irs.gov ↗.
• □ Business insurance. General liability at minimum. Professional liability if relevant.

First year

• □ Quarterly estimated tax payments. Self-employment tax is 15.3% on net earnings in addition to income tax 🔍 verify×DON'T TRUST, VERIFYClaim: SE tax is 15.3% (12.4% Social Security + 2.9% Medicare).Verify at: IRS SE tax ↗SS portion applies only up to annual wage base; Medicare has no cap.. Missing estimated payments triggers underpayment penalties.
• □ Solo 401(k) setup. Must be established by December 31. See Solo 401(k) Guide.
• □ HSA if you have a high-deductible plan.

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