Can I be double-taxed if my corporation sells its assets and then I take the money out personally?

Yes, this is the classic downside of an asset sale compared to a share sale, and it's a big part of why the choice between the two structures matters so much. When your corporation sells its assets, the corporation itself pays tax first, on its own gains — capital gains tax on goodwill, and often recapture taxed as income on depreciated equipment. Only after that does the remaining, already-taxed money sit inside the corporation, and when you then take it out personally, typically as a dividend, you pay a second layer of personal tax on that distribution.

This combined corporate-then-personal tax burden can end up higher than a straightforward personal sale of shares, where you'd pay tax only once, potentially sheltered in part by the capital gains exemption if your shares qualify. There are tools that soften this, most notably the corporation's capital dividend account, which lets the non-taxable portion of a capital gain flow out to you as a tax-free dividend, but this generally reduces rather than eliminates the double-tax effect.

Because the numbers here depend entirely on your corporation's actual gains, existing tax attributes, and personal situation, running the real comparison between an asset sale and a share sale with an accountant, before the deal is structured, is essential.