Decide when recurring family care should become a paid role—and how to define pay, duties, records, benefits, and inheritance expectations before payments begin
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Employer stock inside a 401(k) deserves a separate review before rollover instructions make a possible NUA analysis unavailable.
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Private hiring can offer choice and continuity. Review the household’s screening, employment, insurance, supervision, access, and backup duties first.
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A concentrated stock position creates investment risk and a tax decision. Build a staged transition that measures both, rather than letting the gain prevent
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Decide whether help for an adult child is money you can permanently give away or a genuine loan your retirement plan expects to receive back.
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Map every equity award, retirement deadline, tax consequence, and owned-share decision before employment ends.
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Separate cash at closing from contingent earnout value, then test whether retirement still works if payments arrive late, shrink, or never arrive.
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Separate confidence in the business from the household’s dependence on a future exit, then decide which resources must stand on their own.
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A useful Roth conversion review begins early, updates as the year’s facts settle, and preserves time to coordinate any year-end decision.
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A higher-income working year may create a giving window. Test the charitable commitment, assets, tax year, and retirement liquidity before funding a donor
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Compare a Roth conversion across today’s joint-filer years and a surviving spouse’s possible single-filer years before deciding what belongs in the plan.
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After a business sale, turn usable proceeds into a repeatable household transfer system while keeping obligations and uncertain payments separate.
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