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Category: Tax Planning

The Chicago Asset Manager’s Guide to Multi-Year Tax Strategy for High Earners

The Chicago Asset Manager’s Guide to Multi-Year Tax Strategy for High Earners For many high earners, tax planning feels compressed into the final weeks of the year. December arrives, your CPA reaches out about estimated taxes, and decisions get made quickly — charitable contributions, retirement contributions, or potential Roth conversions [...]

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Tax-Aware Investing vs. Traditional Portfolio Management: Which Approach Makes Sense for Your Wealth?

High-net-worth investors in Chicago are often given conflicting advice about portfolio construction. Some wealth management firms emphasize traditional, long-only investment strategies focused on pre-tax returns. Others highlight tax-aware investing approaches designed to manage taxes alongside market exposure. So which approach is better? The reality is that neither strategy is universally [...]

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