Financial Education & Training to Improve Your Retirement
Follow the blog for our latest thoughts on the stock market, investing, and financial planning issues impacting our clients. You’ll find a ton of great articles on option trading, covered calls, income investing, and more.
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Covered Call Pros and Cons
Covered calls can be a powerful way to earn extra income from stocks you already own. Like any strategy, they come with trade-offs. Before diving into how they work, it…
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How to Protect Gains with Options
Most investors are happy with unrealized gains, but there’s always a risk of loss until they sell. Fortunately, there are a couple of options strategies that you can use to…
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Covered Call Mistakes That Can Hurt Your Portfolio
Covered calls are often promoted as a practical way to create additional income from a stock portfolio. When used correctly, they can help investors generate steady cash flow, lower the…
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Covered Calls and Risk: Building Income While Protecting Your Portfolio
Covered calls have become a go-to strategy for investors seeking additional portfolio income, particularly those preparing for or living in retirement. The strategy is often viewed as conservative compared to…
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The Impact of Dividends on Covered Calls
Dividend-paying stocks remain a cornerstone of income-focused portfolios in 2026. Roughly 75–80% of large-cap companies in the S&P 500 still pay dividends, along with a majority of mid-cap firms. For…
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Calls vs. Puts for Retirement Income: What Actually Matters
When most investors first explore options for income, the question is often: should you use calls or puts? But framing it this way can actually lead you in the wrong…
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Conservative Option Strategies That Can Boost Retirement Income
Option trading often carries a reputation for being risky. In reality, the risk depends far more on how the strategies are used than on the tools themselves. The same is…
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2026: February and March Recap
A Note to Our Readers: The post below was originally written as personal monthly letters to our Charter Asset Management clients from our CEO, Jesse Anderson. We have modified them slightly to…
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Retirement Reality: The Shift from Accumulation to Cash Flow
The security of a steady paycheck is something most people take for granted during their working years. Every two weeks, income shows up, bills get paid, and life moves forward…
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Fixed Income vs. Financial Control: Retirement on Your Terms
Does retirement signal the end of financial control? Too often, it feels that way. Many retirees find themselves shifting from a lifetime of earning and accumulating to a phase defined…