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Every issue, Frank Kestler of Rosemark Advisors answers a real question from an AMAC member, in plain English, with no sales pitch. Read the latest column, run your own numbers, or ask Frank something yourself.

Frank’s latest column

Your 401(k) Got You to Retirement. What Comes Next?

Frank Kestler, Rosemark Advisors AMAC Magazine · Vol. 20, Issue 5 3-minute read

“Frank, I’m retiring at the end of the year and have spent decades building my 401(k). What should I do with it? Should I roll it into an IRA?”

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This is one of the most common questions I hear from AMAC members. If you’re asking yourself the same thing, you’re not alone—and asking now already puts you ahead of most people. I think there’s a better question:

What do you need this money to do for you now?

During your working years, your 401(k)’s job was accumulation. In retirement, that job changes. Your savings may need to create income, keep growing, protect against market losses, address long-term-care concerns, or preserve assets for your family—often some combination of all five. That’s why there’s no cookie-cutter answer.

Start with what’s actually inside the account. Pre-tax 401(k) money can generally roll into a traditional IRA tax-deferred; Roth 401(k) money into a Roth IRA. Move pre-tax money into a Roth, though, and you create a taxable event. And a direct rollover to the new custodian can avoid the mandatory 20 percent withholding that applies when a distribution is paid to you first.

There’s more. Retirees who leave an employer during or after the year they turn 55 may qualify for an exception to the 10 percent early-distribution penalty on withdrawals from that plan—one a rollover could quietly eliminate. If your 401(k) holds highly appreciated company stock, rules around net unrealized appreciation are also worth reviewing first. Get it wrong, and you could overpay in taxes.

These are just a few reasons I tell retirees: Build the plan first, move the money second.

An IRA may offer more flexibility—part generating income, part staying invested for growth, part protected with a guaranteed return, part addressing long-term care, part diversified into alternatives.

The right answer often involves several strategies, each with a specific job. That is retirement planning.

Before you decide anything, sit with these: How much income will I need? How much risk am I comfortable taking? How much should be guaranteed? How will I address long-term care, taxes, and legacy?

If you don’t have confident answers yet, that’s normal.

At RoseMark Advisors, powered by AMAC, we start with one question: What does a confident retirement mean for you? From there, we help you work through income, taxes, risk, long-term care, and legacy—and build a plan around your answers, not ours.

You spent decades building your 401(k). Before you roll it over, it’s worth one honest conversation about what it needs to do for you now.

Frank Kestler
Financial Advisor, Rosemark Advisors

401(k) vs. Traditional IRA: What’s the Difference?

401(k): A retirement plan offered through an employer. Contributions are generally deducted from your paycheck, and some employers provide matching contributions. A 401(k) typically has higher contribution limits but fewer investment choices.

Traditional IRA: A retirement account you establish independently. It generally offers more investment choices, although contributions may not be tax-deductible depending on your income and workplace retirement coverage.

What They Share: Both can provide tax-deferred growth, and withdrawals are generally taxable in retirement. Both may also be subject to required minimum distributions.

Can You Have Both? Yes—but contributing to a workplace plan may affect whether your traditional IRA contribution is deductible.

This column is for general education only and is not individualized tax, legal, or investment advice.

Money tools

Run your own numbers

Two quick estimates: what your funds may be costing you in taxes, and what you must take out of your IRA this year.

What are your funds costing you in taxes?

Estimate the yearly tax on mutual fund distributions, even in years you don’t sell.

$10K$5M
How much do your funds pay out each year?

Not sure? Add up the dividends and capital gain distributions on last year’s 1099-DIV, then divide by your account value.

Your combined tax rate (federal + state)
Estimated tax this year
$7,000

on about $25,000 of distributions, without selling a single share.

Over 10 years at this pace$70,000
If the portfolio paid out just 1% a year$14,000

Want someone to look at your actual 1099s and options?

Book a free review

Illustration only. Assumes the account value and payout stay level and every distribution is taxed at the rate you chose; real results depend on qualified vs. ordinary dividends, short- vs. long-term gains, and your full tax picture. The 1% line is a hypothetical comparison, not a projection for any specific fund or ETF. Not tax advice.

Partner From Rosemark Advisors

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Frankly Financial is provided for general educational purposes and is not individualized investment, tax, or legal advice. Consult a qualified professional about your own situation.

The archive

Earlier Frankly Financial columns

Past questions from members, answered by Frank.

The Tax Bill You Never Saw Coming

Frank, I didn't sell any of the mutual funds in my taxable investment account last year, so why am I paying taxes?

Read column

“I’m in Great Health; Why Would I Need Long-Term Care Planning?”

Frank, I take care of myself; why would I ever need long-term care?

Read column

IRA Distribution Planning: Should You Wait for RMDs?

Frank, I am 65 and retired. When do I have to start taking required minimum distributions (RMDs) from my IRA—and should I just wait until then to start drawing money out?

Read column

Lifestyle vs. Legacy Assets: Spending with Intention in Retirement

How do I know which of my assets to spend first in retirement, and which are better to leave to my children?

Read column

Do I Really Need Long-Term Care Planning? - AMAC Magazine Exclusive

Many retirees mistakenly assume Medicare or Medicaid will cover long-term care. Discover smarter, tax-efficient strategies to protect your retirement.

Read column

The Hidden Advantages of Working with a Wealth Planner - AMAC Magazine Exclusive

Are your investments missing something? Discover how a comprehensive wealth planner can uncover tax-saving strategies that don’t show up on your statement.

Read column

Is Uncle Sam Taking More Than His Fair Share? How to Keep Your Retirement Savings Out of the IRS’s Hands

I’ve worked hard, saved diligently, and played by the rules! Now that it’s time to enjoy my retirement, I fear I’m handing over too much of my money to Uncle Sam. How can I withdraw my savings without getting slammed with taxes?

Read column
Frank Kestler
Meet your columnist

Frank Kestler

Financial Advisor, Rosemark Advisors

Frank answers AMAC members’ money questions in Frankly Financial, a column in AMAC Magazine.

Ask Frank a question

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