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Hey, it’s Jeffrey — back again!
Most financial experts recommend rebalancing your portfolio at least once a year. The idea is simple: over time, your winners grow, and your losers shrink, and your portfolio drifts away from the risk level you originally wanted. Rebalancing just means buying and selling to get back to your target.
Simple concept. But actually doing it? That's the tedious part. Logging in, doing the math, figuring out what to sell vs. what to buy, remembering which accounts to do it in so I don't trigger unnecessary taxes.
I've been putting this off for months. So I handed it to ChatGPT. I love using AI for tedious tasks, and this might be a new favorite.
The prompt:
Help me rebalance my portfolio. Here's what I have:
Current holdings:
[List each fund/investment, current value, and which account it's in — e.g., "VTSAX - $50,000 - Roth IRA"]
My target allocation:
[e.g., 60% US stocks, 20% international, 20% bonds]
New money to invest (optional): [$X or "none, just rebalancing"]
Please:
1. Show me how my current allocation compares to my target
2. Tell me exactly what to buy or sell to get back to target
3. If I should sell, tell me which account to do it in to minimize taxes
4. If I have new money, show me where to put it to help rebalance
Keep it simple and just give me the specific moves.
Tip: You don't have to type out all your holdings. Screenshot your portfolio from Fidelity, Schwab, Vanguard, Monarch, or wherever — ChatGPT can read it.
What I found: ChatGPT gave me the exact dollar amounts to buy and sell, told me which account to do it in, and even suggested how to use new contributions to rebalance without triggering taxes. A task I'd been avoiding for months, done in 30 seconds.
One note: LLMs have gotten better at math, but always double-check the numbers before making any trades. The output is a starting point, not a final answer.
Keep going? Once you've got your rebalance plan, try:
"How often should I actually rebalance?"
"Which account should I hold bonds in for the best tax efficiency?"
"How do I rebalance without selling anything?"
Reply and tell me how lopsided yours was.
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One quick note: This newsletter is for educational purposes only and does not constitute financial advice. I'm not a financial advisor — just someone sharing ideas and tools I've found useful. Use what works for you, skip what doesn't, and always do your own research. Some links may be affiliate links or sponsored content for which I may receive compensation.