How to Turn Your Portfolio Into Retirement Income (Without Guessing)

Author: Mike O'Shaughnessy

Feb 18 2026 21:00

Turning your investments into reliable retirement income requires a clear withdrawal strategy, smart Social Security timing, and thoughtful tax-efficient planning. Your plan should balance growth...

Turning your investments into reliable retirement income requires a clear withdrawal strategy, smart Social Security timing, and thoughtful tax-efficient planning. Your plan should balance growth and stability while reducing the risks that can derail long-term income. At Ascent Financial Group here in Richmond, Virginia, we help retirees across Central Virginia build coordinated strategies that make their money last.

Creating predictable retirement income doesn’t have to feel overwhelming. With the right structure—and a plan tailored to your goals—you can turn a lifetime of saving into a steady paycheck that supports your lifestyle for decades. Below, we break down the key concepts in simple, conversational language so you can move forward with confidence.

Building a Withdrawal Strategy That Works

Your withdrawal strategy determines how you take money out of your portfolio each year. A common starting point is the “4% rule,” which suggests withdrawing about 4% of your savings in the first year of retirement and adjusting for inflation over time. But this traditional approach may not fit every situation—especially for executives, entrepreneurs, or families managing complex financial lives here in Central Virginia.

The goal is simple: balance income with long-term sustainability. Your strategy should consider your lifestyle needs, market conditions, tax planning opportunities, and how much flexibility you want year to year.

Understanding Sequence of Returns Risk

Sequence of returns risk refers to the danger of experiencing poor market performance early in retirement. Even if long-term returns average out, the timing of bad years can significantly impact how long your money lasts—especially if you’re making withdrawals during downturns.

At Ascent Financial Group, we help clients in Richmond structure portfolios to weather different market environments. This might include having multiple “buckets” of money—some designed for stability, others for long-term growth—so you’re not forced to sell at the wrong time.

How Taxes Affect Your Retirement Income

Tax planning is one of the most overlooked parts of retirement income strategy. Every withdrawal—whether it’s from a brokerage account, traditional IRA, Roth IRA, or employer plan—comes with different tax implications. Coordinating your withdrawals year by year helps you keep more of what you’ve worked hard to earn.

To explore these strategies in more detail, visit our Tax Planning page.

Social Security Timing: When Should You Claim?

For many retirees, Social Security is a foundational income source. But deciding when to start claiming—whether at 62, full retirement age, or age 70—has a significant impact on your monthly benefit.

  • Claiming early gives you income sooner but permanently reduces benefits.
  • Waiting longer increases your benefit by roughly 8% per year between full retirement age and age 70.

We help clients across Central Virginia evaluate how Social Security fits into their broader retirement income plan—not just by itself, but alongside investment withdrawals, pensions, taxes, and spousal benefits.

Understanding Required Minimum Distributions (RMDs)

Once you reach the IRS-defined RMD age, you must begin withdrawing from traditional retirement accounts. These withdrawals count as taxable income, which can push you into a higher tax bracket if not planned for in advance.

A proactive plan ensures your RMDs don’t create unnecessary tax surprises—and helps you integrate these distributions into the rest of your retirement income strategy.

Roth Conversions: A Helpful Tool for Tax-Efficient Income

Roth conversions allow you to move money from a traditional IRA to a Roth IRA in exchange for paying taxes today. This strategy can reduce future taxable income, create more flexibility with RMDs, and provide tax-free withdrawals later in retirement.

For many Richmond-area retirees—especially those with fluctuating income or significant savings—well-timed conversions can be a powerful long-term planning tool.

Coordinated Planning Brings It All Together

Turning your savings into income takes more than investment management—it requires thoughtful coordination across taxes, Social Security, withdrawal strategies, and long-term cash flow planning. That’s the kind of integrated approach we take at Ascent Financial Group here in Richmond.

If you want to dive deeper into how these pieces fit together, explore our Retirement Income Planning resource.

Ready to Build a Retirement Income Plan That Works for You?

If you’re preparing for retirement in Richmond or anywhere in Central Virginia, we’d love to help you build a steady, tax-efficient income strategy that's tailored to your goals. Complete our right-fit questionnaire to see if you’re a good match for Ascent Financial Group.


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About the Author

Author

Together, Mike and Dustin are the dynamic duo of Ascent Financial—combining Dustin’s knack for cracking big financial puzzles (while juggling three energetic daughters) with Mike’s journey from corporate burnout to advisor, fueled by golf swings and guitar strings.


Together, they blend sharp strategy with a refreshingly human touch, making wealth management feel less like a boardroom briefing and more like a conversation with friends who’ve got your back.