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Creating Retirement Income From Your Portfolio

Creating Retirement Income From Your Portfolio
Key Takeaways:
  • Your portfolio only has to cover the gap. Add up what you spend, subtract the income that shows up on its own like Social Security, a pension, or rent, and what’s left is the job your investments actually need to do.
  • You don’t need high-yield holdings to get paid. Interest and dividends cover part of it. Planned sales and rebalancing turn growth into spendable cash for the rest, without bending the whole portfolio out of shape to chase income.
  • Where you pull from changes what you keep. The same withdrawal can leave you with very different money after taxes depending on whether it comes from a taxable account, a traditional IRA, or a Roth.

Table of Contents

Saving for retirement and living off that money are two different jobs. For decades the account just had to grow. Now it has to hand you something like a paycheck every month and still be there in twenty years.

The average American has about $547,840 in retirement savings,1 and how you draw that down matters nearly as much as how much you saved.

This is about that second job: turning the balance into a steady paycheck. It picks up after you’ve sorted out whether you can retire and roughly what you’ll spend. From there, the work is getting money out of your accounts and into your life, month after month, without the well running dry.

Estimate the Income Gap After Social Security and Pensions

This piece picks up after you’ve confirmed you can retire and you have a rough number for what retirement will cost. From here, one figure runs everything: the gap between your yearly spending and the income that shows up on its own.

Add up your dependable income, Social Security, a pension, maybe rent or an annuity payment, and subtract it from what you plan to spend. Whatever’s left is what the portfolio has to produce. Say you’ll spend $150,000 a year and $80,000 arrives from those dependable sources; the portfolio is on the hook for about $70,000, and often more in the early years, before every check has started.

Build a Portfolio That Can Support Regular Withdrawals

The mix that got you here may not be the mix that pays you. You still need growth for the years ahead, but the money you’ll spend soon needs somewhere steadier to sit, so a bad market doesn’t force your hand the month a bill comes due.

The fix is to decide two things: how your returns turn into cash, and which holdings cover which stretch of time. Get that right and the portfolio can fund today’s withdrawals, dodge selling at the worst moment, and still keep pace with prices down the road.

Generate Cash Flow Through a Total-Return Approach

“Total return” just means you live off everything the portfolio earns, not only the interest and dividends it pays out. Interest, dividends, a maturing bond, some cash on hand, and the occasional sale of something that’s gone up all count toward your paycheck.

That flexibility matters. In a year when dividends and interest cover only part of the gap, you can sell an appreciated stock fund or trim a winner instead of reaching for holdings that pay more. Chase yield and you usually buy trouble along with it: shakier bonds, concentrated bets, dividends that can get cut.

Yield isn’t the enemy. It’s one input among several. A broad mix you turn into cash on a schedule beats a portfolio contorted to throw off income.

Give Each Part of the Portfolio a Job

Every slice of the account should have a role. Once it does, you can look at any upcoming withdrawal and know exactly where the cash is coming from and what gets to stay invested.

A setup that works often looks like this:

  • A cash reserve for the next year or two. Cash, money market funds, short-term bonds, and maturing holdings, enough to cover a good stretch of upcoming withdrawals. This is the bucket you actually spend from, so a sharp drop in stocks never forces a bad sale.
  • A stability layer. High-quality bonds to smooth out the ride and cover withdrawals past that first reserve, sized to your timeline.
  • The growth engine. Stocks and similar holdings you won’t touch for years. They have time to recover from downturns and to outrun rising prices, which is what protects you late in a long retirement.
  • Spread it around. Across companies, sectors, bond issuers, and maturities. No single holding should carry an entire role by itself.
  • Match the risk to how much you lean on the account. If most of your income comes from this portfolio and little of your spending can flex, you can carry less risk than someone with a pension and a loose budget. That’s a matter of capacity, which isn’t the same as your gut tolerance for market swings.

Decide Which Accounts Will Fund the Income

Raising the cash is only half the job. Pull the same amount from three different accounts and you can end up with three different tax bills, which means three different amounts left to actually spend.

So the question isn’t just how much, it’s from where. This is the part that turns a plan into a routine, so you’re paying bills on autopilot instead of making a fresh call every month.

Pull From Your Accounts in a Tax-Aware Order

You’ve likely seen the classic sequence already: spend from cash and taxable accounts first, traditional retirement accounts next, Roth last. That order is a fine default. The value is in knowing when to bend it, because each account type gives you a different lever.

Keep these in view as you decide where this year’s money comes from:

  • Taxable accounts. You’re taxed only on the gain when you sell,2 and the interest and dividends are usually adding to your income already, so these often go first.
  • Traditional IRAs and 401(k)s. Withdrawals are ordinary income, and putting them off just grows a bigger required distribution later on.3
  • Roth accounts. Qualified withdrawals are tax-free,4 so save them for a high-income year, a big purchase, or a legacy.
  • Blend the accounts and time it across years. Pulling measured amounts from more than one account type usually beats a rigid order. Line withdrawals up with your brackets, Roth conversions, required distributions, how much of your Social Security gets taxed,5 and your Medicare premiums,6 and treat a low-income year early in retirement as prime time for a conversion.

Set Up a Reliable Way to Receive the Income

Once you know how much and from where, automate the delivery. A monthly or quarterly transfer into checking can feel a lot like the paycheck you used to get, and a cash-management account can hold enough for regular bills and near-term buys.

How often you pay yourself is mostly about what keeps budgeting simple. Monthly mirrors a paycheck and suits steady spending, while quarterly means fewer transactions and a bit more to manage between deposits. Either way, set the transfer off the after-tax figure, since federal tax generally has to be paid as the income comes in, through withholding or estimated payments. Don’t mistake a gross withdrawal for spendable money.7

Between transfers, interest, maturing bonds, planned sales, and rebalancing refill the cash. Check your deposits against what you’re actually spending once or twice a year, so a shortfall or an oversized withdrawal gets caught before it throws off the income you’re living on.

Keep the Income Plan on Track as Retirement Develops

Your first withdrawal number gives you a frame. Life won’t follow the projection, though. Markets move, prices climb, and health or family can change what you need or how hard the account has to work.

Rebalancing and taking income can be the same move. When one slice of the portfolio runs ahead, selling part of it to fund your withdrawal does two jobs at once: it raises the cash you need and nudges the mix back toward target. Refilling the cash reserve by trimming whatever has grown too large means the income you take and the rebalancing you’d do anyway tend to happen together, instead of becoming a separate chore that gets skipped.

Declines hit harder once you’re withdrawing, because selling shares while they’re down locks in the loss and leaves less to recover. That’s the cash reserve’s whole purpose. During a long slump you spend from cash and short-term bonds instead of selling stocks, which buys your growth holdings time to come back. If it drags on, trimming flexible spending like travel or gifts takes pressure off before the essential bills feel it.

Guardrails give you preset points for when to raise, hold, or cut withdrawals, so the call isn’t driven by nerves. Review the whole plan at least once a year, and any time something big shifts: health, housing, taxes, family, or outside income. Reset the withdrawal off today’s balance and today’s costs rather than dragging an old projection along.

Creating Retirement Income From Your Portfolio FAQs

1. How do I decide how much to pull from my portfolio each year?

Start with the gap between your spending and your dependable income; that’s your baseline. From there, let three things set the exact amount: your cash reserve, which accounts you draw from, and how flexible your spending is.

2. Is it better to live on dividends and interest or sell investments?

Usually both. Let interest and dividends cover part of the gap, and fill the rest with planned sales and rebalancing. That way you’re not rebuilding the whole portfolio around high-yield holdings just to avoid selling anything.

3. How much cash should I hold for retirement income?

Enough to cover upcoming withdrawals and any known short-term costs without selling growth holdings in a weak market. The right cushion depends on your outside income, how flexible your spending is, your bond holdings, and how comfortable you are refilling it.

4. Which retirement account should I withdraw from first?

The one that funds this year’s needs while keeping your tax bill reasonable now and later. Taxable, traditional, and Roth can all play a part, and a blend often works better than following one fixed order.

5. How can I avoid selling investments during a market downturn?

Keep your upcoming withdrawals in cash, short-term bonds, or maturing fixed income, so you’re spending from the calm part of the portfolio. Then refill that reserve once markets recover, through rebalancing or planned sales, so the buffer is back before the next drop.

6. How often should I adjust my portfolio withdrawals?

At least once a year, plus any time something major changes. Look at what you actually spent, your taxes, your returns, your reserve level, and your outside income, then make a measured tweak when the numbers ask for one.

Get Help Creating a Coordinated Retirement Income Strategy

A good income plan starts with the gap, sets a withdrawal you can sustain, and splits the portfolio between money you’ll spend soon and money that keeps growing. Then it lines up which accounts feed the cash, so what lands in checking actually supports the life you want once taxes are paid.

We can model your spending, stress-test your withdrawal rate against rough markets and a long life, and organize the portfolio around both near-term income and future growth. From there we set up a distribution process that fits your bills, your reserve, and the schedule you like.

We’ll also coordinate those withdrawals with your tax picture, keep an eye on how it’s tracking, and suggest measured changes as markets and your circumstances shift. To see how a coordinated approach could support your retirement, schedule a complimentary consultation with our team.

Resources:

1) Empower Average Retirement Savings by Age

2) Capital Gains and Losses

3) IRA Distributions

4) Designated Roth Accounts

5) Taxes on Social Security Benefits

6) Medicare Costs

7) Tax Withholding

Christina Norwood, Operations Manager at Oak Street Advisors

Christina Norwood​

Operations Manager

Born and raised in Maryland, I moved to South Carolina in 2023 and joined Oak Street Advisors’ Myrtle Beach office in 2024 as the firm’s Operations Manager.  I’ve worked in the financial services industry most of my career, including ten years for a large brokerage firm and the last two years as a Client Relations Specialist at a similarly sized RIA. 

I enjoy working hand-in-hand with our clients on all administrative and operational needs. Client satisfaction and planning efficiency are my top priorities, and I take pride in providing proactive service to every client household at Oak Street Advisors.
 
While not in the office, I enjoy quality time with my family, walking my rescue dog, Auggie, on the beach, cooking, and exploring South Carolina.

Ryan Coope

Ryan Cooper

Fiduciary Financial Advisor

​I joined Oak Street Advisors’ Myrtle Beach office in 2021. I currently serve as a fiduciary financial advisor and associate financial planner. I hold the Series 65 and am working toward obtaining my CERTIFIED FINANCIAL PLANNER™ certification. 

I strive to provide clients diligent and proactive service while assisting the team with planning, investment strategies, and recommendations.

While not in the office, I enjoy running, golfing, fishing, going to the beach with my wife Natalie and our son Bennett, and watching my beloved Green Bay Packers play (I even own stock in the team!).

Bryan Taylor, CFP®, Owner and President of Oak Street Advisors

BRYAN TAYLOR, CFP®

Owner & President  | Fiduciary Financial Advisor

I graduated from Clemson University and began my financial planning career shortly after with a small advisory firm on the ground floor — learning the basics of financial and tax planning and running a financial advising business.

At the same time, I enrolled in the University of Georgia Terry College of Business’ Executive Program in Financial Planning and completed the coursework at nights and on weekends. Soon after, I completed my CFP® certification and joined the family business.

A year after I joined the firm, we opened our second location in Mt. Pleasant, SC where I reside with my family. Over the next 10+ years I cherished the opportunity to learn and grow the family business with my father. We worked hard to build the firm into what it is today — something we’re both proud to say we accomplished together.

Today, I serve in a Senior Advisor and Planner role, working together with our team on all financial plans and strategies. By collaborating we provide fiduciary financial and tax planning and asset management to our clients within a fee-only business model — which reflects our commitment to putting our clients’ interests above the next dollar.

When I’m away from the office, I enjoy playing golf, boating, pulling for the Clemson Tigers, and relaxing on the beach with my wife, Laura, and daughters Riley and Ramsey.

Links:
NAPFA – National Association of Personal Financial Advisors
CERTIFIED FINANCIAL PLANNER® professional
LinkedIn
Fee Only Network