John

Problem: John, a Google exec in his 50s, dreamed of more time for his passion, restoring planes, but felt trapped by stock concentration and job pressure.

Solution: We ran downside scenarios on his Google stock and mapped out how little income he’d need to maintain his goals, even if his $2M vanished.

Outcome: With renewed confidence, John diversified $500K, sold his Napa home, and moved closer to an airstrip in Utah, still working at Google, but ready to walk away on his terms.