One key point of clarification that would be helpful in considering US tax questions:
The 37% rate only applies to the top tax bracket on ordinary taxable income. For lower income levels, the percentage ranges from 10% to 37% across 7 income brackets. And that only applies to short term gains.
Long term gains are taxed under the capital gains provisions at 0%, 15%, or 20% depending on your income levels and whether you are single, married, etc.
True, I just used the 37% as a default, but Charlie doesn't seem like the millionaire type. At any rate, it's a placeholder percentage, but what stays the same is the variation between short/long term gains which naturally incentivizes inaction.