You Get One Shot at Retirement Income: Jeremy Keil on the 5 Steps to Get It Right

About This Blog

You spent forty years learning how to save. Almost no one taught you what to do with the money once the paychecks stop. That gap is the reason so many people reach retirement with a healthy balance and still feel unsure every month. In this episode of Safe Money Radio, host Brett Blake sits down with Jeremy Keil, a CFP, CFA, and CKA who has spent more than twenty years helping people near retirement turn their savings into income. Keil is the author of Retire Today and the creator of the Mr. Retirement YouTube channel. Here is what he covered, in plain language, for anyone trying to turn a lifetime of saving into a paycheck that lasts.

Enough Income, Not Enough Money  

Most people walk into retirement solving the wrong problem. They ask, do I have enough money? Keil says the real question is, do I have enough income. That one change reframes every decision that follows.

He puts it in terms anyone can feel. You work for forty years and put money away every paycheck, roughly twenty-six times a year. That is about a thousand chances to practice saving. Then you retire, and you get one chance to turn all of it into income you cannot outlive. His advice is simple. Follow a process. Do not wing it. The five steps below are that process, and the order matters.

Step One: Know How Long Retirement Lasts  

The first step is to spend, and it has two parts. How much will you need, and how long will you need it. Most people get the second part wrong in both directions.

Ask a 55-year-old when they plan to retire, and they often say 65. Ask a 65-year-old when they actually retired, and the answer is often 62. People tend to leave work about three years earlier than they expected. On the other end, Keil says most people underestimate their own lifespan by four or five years. Put those two together, and the math gets dangerous. You build a plan that starts three years early and runs five years long, and those extra years can show up as zeros because no one planned for them. As Brett put it, the worst case is being healthy and happy and realizing you planned wrong, running out of money before you run out of life.

Step Two: Count What You Will Make  

Step two is 'MAKE.' Retiring does not mean you stop making money. Social Security, a pension, and other income sources keep paying. The two that matter most are Social Security and your pension because both are one-time, lifetime decisions you cannot easily undo.

Keil points to research from economist Larry Kotlikoff suggesting only about 4 percent of couples make the best possible Social Security claiming decision. On average, the people who miss the mark may leave around $180,000 of lifetime income on the table. His rule for getting it right is short. Learn the math, do the math, follow the math.

The piece most couples miss is the survivor benefit. When both spouses are alive, the combined benefit is roughly the same no matter who claims when. So Keil often has the higher earner wait and the lower earner claim earlier. While both are living, the couple collects about the same total. But when one spouse passes, the survivor keeps the larger of the two benefits, now 20 to 25 percent higher, for the rest of their life. It costs the couple nothing while both are alive, and it protects the one left behind. In his words, he has never met a widow who wished she had less Social Security income.

Step Three: Keep More of What You Saved  

Step three is keep. Most people look at last year's taxes or this year's taxes. Keil looks at the whole arc of retirement, projecting a tax picture 25 or 30 years out. The reason is that early retirement often brings low-tax years, which feel great but can be a missed chance. Traditional retirement accounts keep growing, and later on the tax rate on that money can climb.

A Roth conversion lets you control the year you pay the tax. Keil's guidance is that a conversion is not a yes-or-no question. The real question is how much and how long. He tells the story of a client at the bottom of the 24 percent tax bracket, for whom the smart move was converting $200,000 a year for three years to fill that bracket. Instead, after the first year she converted the remaining $400,000 all at once, pushing the money into the 32 and 35 percent brackets. That single misstep cost her about $23,000 in extra tax. The lesson is the golden rule of conversions. It is not about doing the whole account. It is about how much, and when.

Step Four: Match Your Money to When You Need It  

Step four is invest, and Keil says this is where most people wrongly start. Your investments exist to meet a need, and you cannot size the need until you have worked through spend, make, and keep.

He favors a bucket approach. Short-term money belongs in short-term holdings you can rely on. Long-term money belongs in long-term holdings built for return. You cannot control what the market does, but you can choose how much risk sits against each part of your timeline. Map out your short-term need and your long-term need, then match the money to the calendar. That is the whole idea.

Step Five: Leave Money, Not a Mess  

Step five is leave. Some people leave behind money. Some people leave behind a mess. Keil hopes you leave the money without the mess.

That means the estate documents, yes, but it also means stress-testing the first four steps. What if you live longer than expected? What if the market drops early? What if inflation runs hot or care costs rise? A good plan looks hard at what could knock it off course and builds in room to absorb the hit. Planning for the good case is easy. Planning for the years that do not go your way is what protects the people you love.

Not a Do-It-Yourself Decision  

Keil's closing thought ties the whole conversation together. You had a thousand chances to get saving right. You get one chance to turn it into income. That is not the place to guess. Follow a process, run the numbers before you make the calls you cannot take back, and get a licensed professional in your corner who does this work every day.

That is the spirit of this show. We spent 40 years teaching Americans how to fill the bucket. Nobody taught them how to turn on the tap without running it dry. This episode is one step toward turning it on with some confidence.

Want to take the next step?Run your own numbers with the free WIYN calculator at brettblake.annuity.com, which takes about three minutes. Ready to talk it through? Book a Retirement Clarity Session with Brett. Not a sales call. Not a slide deck. Your numbers, not ours.

Worry Less. Live Longer.

About the host

Brett A. Blake hosts Safe Money Radio and is the CEO of Annuity.com. He is 58, a Harvard MBA who will tell you the degree taught him almost nothing about retirement income. Before Annuity.com, he helped scale a business to nearly $1 billion in annual sales. He lives in Gilbert, Arizona with his wife Erin, and asks the questions every retiree would ask if they had access to the right rooms.

About the guest

Jeremy Keil is a CFP, CFA, and CKA and the founder of Keil Financial Partners near Milwaukee. Over more than twenty years he has helped hundreds of people near retirement turn their savings into income. He is the author of Retire Today: Create Your Retirement Master Plan in 5 Simple Steps, the host of the Retire Today podcast, and the creator of the Mr. Retirement YouTube channel.

Follow or Subscribe to Safe Money Radio Podcast on your favorite platforms

Website: safemoneyradio.com | YouTube: @SafeMoneyRadioPodcast | Facebook: Safe Money Radio | Instagram: @safemoneyradiopodcast | TikTok: @safemoneyradiopod | Twitter (X): @safemoney_radio

Follow Brett A. Blake

LinkedIn: @brettblake | Retirement tools: brettblake.annuity.com | Email: brett.blake@annuity.com

Follow Jeremy Keil (CFP, CFA, Author and Creator of Mr. Retirement)

LinkedIn: @mrretirement | Website: keilfp.com | YouTube: @MrRetirement

#RetirementIncome #GuaranteedIncome #SocialSecurity #RothConversion #RetirementStrategy #RetirementPlanning #SafeMoneyRadio #JeremyKeil #MrRetirement

DISCLAIMER:

Safe Money Radio is for educational purposes only and does not constitute investment, tax, or legal advice. Products discussed may not be appropriate for everyone. Always consult a licensed professional before making financial decisions. Product availability varies by state. Our Agents are licensed to sell insurance products, including annuity products that guarantee retirement income based on the financial strength of the insurance company providing the product. Annuities may not be suitable for everyone. Guarantees are not government-backed or provided by Annuity.com, Inc. Annuity.com, Inc. is a licensed insurance agency. National Producer Number (NPN): 21086345. Licensed in all states where required by law. Doing business in Florida and California as "Annuity.com Insurance Marketing," CA License No. 6013124. In New York, licensed as Annuity.com Insurance Solutions, License No. LA-1860109.