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how can I determine if the stock picks I have made over the years were overall better than just investing the same money in the SP500.

If you have made no additions or deductions from the account for the time period, the easy way is to divide the end of the month value of the account by the end of the month value one year ago. Then subtact 1 and multiply by 100 to get the percentage gain for your account.

Similar data for mutual funds is difficult. It is easy to get numbers for the change in share value. Yahoo finance plots do that in comparison mode with any other stock. But most would include dividends (or other distributions) paid in that period.

When you have a series of transactions, the calculation gets more complex. Then you need to do the calculations with groups of stocks or account for new money added or withdrawals.

The best way is to do the calculation for a series of years, plot it on semilog paper and use the slope of the line to estimate. Or use the compound interest formula to estimate your compound annual growth rate.
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