On this episode of Simply Money, Bob and Brian tackle a question that hits differently when you’ve built real wealth: if the market dropped 20% tomorrow, what would you actually do? They walk through the emotional and mathematical realities of managing a $2–10 million portfolio, why risk tolerance and plan design don’t always align, and how shifting from accumulation to preservation changes everything. You’ll also hear strategies around sequence of returns risk, separating income streams from piles of money, and why diversification today may mean more than just a 60/40 portfolio. Plus, the guys explain why bonds weren’t the “safe haven” many expected in 2022, how to think strategically about 401(k) contributions across pre-tax, Roth, and after-tax buckets, and answer listener questions on retirement withdrawals, dividend income, and spending in early retirement.