Here’s the pattern I see over and over:

• Stay mostly in stocks until retirement
• Then sell a big chunk, trigger a large capital gains bill
• Move the proceeds into bonds that throw off fully taxable income or low‑yield munis

You end up paying a lot of tax for the privilege of owning assets that may not even keep up with inflation after tax.

Here’s how I actually think about building income for people in or near retirement:

1. Focus on risk first, not “income” labels

The goal is a lower‑volatility portfolio so sequence‑of‑returns risk is manageable. Many income‑oriented assets happen to be lower volatility, but the real engine is rebalancing between uncorrelated asset classes. Some months your “income” might simply be trimming stocks back to target.

2. Make your income tax-free

There are many ways to do this. Real estate and infrastructure investments can use depreciation to shield distributions from taxes. Securitizing affordable housing loans takes those muni yields to double digits. Pairing taxable credit with tax-aware hedge funds can create a powerful tax shield for income (or even Roth conversions).

3. Be surgical with big, one‑off purchases

When someone wants to fund a large purchase, we don’t blow up the plan and sell a pile of appreciated assets all at once. We look at box spread loans against the portfolio for cheap, tax-deductible financing which we can roll forward or pay off at any time.

4. Overall tax-aware portfolio design

When your stocks are harvesting 10% - 20% capital losses, your hedge fund allocation is realizing 30% ordinary deduction, and your real estate is passing hundreds of thousands of passive losses to you, you can dramatically reduce the drag taxes have on income, withdrawals, and rebalancing.

If you’re within 5–10 years of retirement, have $5M+ of investable assets, and want your income plan to be built this way instead of “sell stocks, buy bonds, hope for 4%,” you can book a call using the link on the home page.