I Gave AI a $2 Million Financial Problem. Here’s What It Missed.
I recently gave AI a hypothetical planning problem. A 58-year-old has $2 million invested, including $900,000 in one highly appreciated stock. They want to retire at 60, help their children buy homes, and give more to charity, but they’re worried about the tax bill if they sell. AI recommended donating some shares, selling the rest gradually, harvesting losses, and diversifying. That’s a pretty good answer. It’s also premature.
Before answering, I’d want to know much more. What’s the cost basis? How much do they spend? Is the other $1.1 million enough to support retirement? And most importantly, which goal matters most? AI only knows the version of your life you put into the prompt, and most people don’t know which details are important enough to include. Family dynamics, health, past experiences, and personal values never appear on an account statement, but they shape what the right decision is.
On speed and information, AI wins easily. But information isn’t the same thing as a decision. The best approach is probably a good advisor using AI: better information combined with human judgment and accountability. If you’d like help connecting the numbers to what matters most to you, Get in Touch — Sound Investment Strategies | Fee‑Only Advisors
