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6 Ways the Drawdown Phase Catches New Retirees By Surprise

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Jeff Judge Managing Partner
Jeff is one of Chesapeake’s founding partners and a go-to advisor for professionals navigating complex transitions like retirement, business sales, or sudden windfalls. With nearly two decades of experience, he’s known for delivering calm, clear guidance when it matters most. Clients say working with him feels like talking to a longtime friend, if that friend happened to be an award-winning financial expert.
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Retirement planning Tax planning Estate planning Equity compensation Business exit planning Sudden wealth and windfall planning Behavioral finance Social Security Medicare Investment management Life insurance Financial planning for women in transition R.U.D.D.E.R. Method Federal employee and military benefits Charitable giving College planning Long-term care insurance Roth conversions High-net-worth financial planning Maryland tax and estate planning
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