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Planning for retirement shouldn’t feel like alchemy, but that’s how it looks when investors tell me they’re banking on 14% annual returns. If your retirement plan requires that kind of performance, what you have isn’t a plan - it’s a wish on a very expensive star.

The reality is simple: retirement planning is mostly about math and discipline. Investors need to understand their expected expenses, know their cash flow, and set goals grounded in reality. We’re not saying skip the cruise ship dream - we’re just saying don’t build your portfolio around lottery odds.

While we’re here, let’s get one thing straight: high yield doesn’t always mean high income. There’s a difference between building a portfolio that generates consistent income and one that looks impressive in a moment of market mania. Too often, investors grab the highest-yielding fund on the shelf, assuming that diversification and branding will save them from bad underlying assets. Spoiler: it won’t.

We prefer a more intentional approach. That means looking under the hood, being selective, and yes, sometimes accepting a slightly lower yield in exchange for dramatically reduced risk. In many cases, a mix of common equity and preferred shares (especially when thoughtfully chosen) can offer both stability and respectable income without the emotional rollercoaster.

This doesn’t mean running from the market. It means acknowledging that not every market environment is the same. When valuations are high, we tread more carefully. That doesn’t mean we stop investing - it means we prioritize quality, track records, and durability over hype. It’s not sexy, but it works.

Let’s also talk about the elephant in the SSA office: Social Security. Waiting longer can lead to significantly higher payouts, but it’s not always the right move. Sometimes it makes sense to file early - especially if health concerns, debt, or trust issues with the system factor into your decision. There’s no one-size-fits-all. There’s only what fits you.

Which brings us to the point: retirement success is rarely about finding one perfect investment. It’s about understanding your income needs, managing your risk, and making intentional decisions over time. That’s it. That’s the magic.

Retirement doesn’t require a $10 million portfolio. It requires a plan - ideally one you’re comfortable sticking to. That might mean cutting expenses, generating a bit of side income, or just dialing back lifestyle expectations. The earlier you do those things, the less pressure there is to take big swings with your investments.

You don’t need to win every trade. You just need to avoid the big mistakes and keep the income flowing. That’s how retirement works - not on vibes, but on structure.

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This article was compiled by my assistant. If there are any mistakes, blame him - I certainly will.

Disclosure: Currently no position in AGNC, DX, NLY, TWO or their preferred shares. I may frequently trade in the preferred shares of any mortgage REIT and occasionally in the common shares.