Retire Today

Jeremy Keil explains the 5 steps you can take if you are planning to retire in 2026 or 2027. If you’ve been planning to retire in 2026 or 2027, it might feel like you still have plenty of time. But in reality, retirement has a way of showing up earlier than expected — and when it does, the people who feel the most confident are the ones who prepared well in advance. In this episode of Retire Today, I walk through five things you should do before you quit working if retirement is anywhere on your near-term horizon. These steps aren’t about picking a perfect retirement date. They’re about being ready — even if your plans change. Why You Should Prepare Earlier Than You Think Two important statistics shape this entire conversation. First, the stock market is historically up about 70% of the time in any given year. That also means it’s down about 30% of the time. If you’re retiring soon, there’s a real chance that your account balances could be lower at retirement than they are today. Second, most Americans retire about three years earlier than they expect. Health changes, job shifts, burnout, or family needs often move retirement forward — whether planned or not. That’s why I encourage people to prepare for retirement three years ahead of time, even if they believe they’ll work longer. Planning early gives you flexibility. Waiting too long removes it. 1. Create a Written Retirement Plan The first and most important step is to put your plan in writing. Many people have a retirement date in mind, but when asked how everything will actually work, they don’t have clear answers. A written plan forces clarity. This is where the 5-Step Retirement Plan comes in: SPENDMAKEKEEPINVESTLEAVE Writing this down helps turn vague ideas into an actionable roadmap — and exposes gaps before they become problems. 2. Build a Lifetime Income Plan Retirement isn’t about having a big account balance — it’s about knowing where your income will come from every month. Before you retire, you should know: At a minimum, you should map out the first 12 months of retirement income in detail. That includes Social Security, pensions, savings, brokerage accounts, and retirement accounts — and the tax rules that apply to each one. Surprises here are costly. Planning removes them. 3. Make Your Retirement Plan Tax-Smart Many people assume their taxes will automatically go down in retirement. Sometimes that’s true — but not always. Pensions, Social Security, required minimum distributions, and investment income can push retirees into higher tax brackets than expected. The key is understanding when you’ll have flexibility and using it intentionally. Retirement often creates opportunities to: Taxes don’t disappear in retirement — they change. Planning ahead helps you adapt. 4. Plan Your Retirement Healthcare Healthcare is one of the biggest unknowns in retirement. Before you retire, you should know: Options may include employer coverage through a spouse, COBRA, retiree health plans, ACA plans, or Medicare — and each comes with different costs and rules. Healthcare planning isn’t just about insurance. It’s about understanding how medical costs interact with your tax plan and your income strategy. 5. Create a Retirement Investment Plan Retirement changes your investment timeline. You’re no longer investing only for growth — you’re investing for income and stability, too. That means separating your money into: Short-term fundsLong-term investments Money you’ll need soon shouldn’t be exposed to short-term market swings. At the same time, money you won’t need for many years still needs growth to keep up with inflation. The right investment plan balances both — and helps prevent panic decisions when markets get volatile. The Bottom Line If you’re planning to retire in 2026 or 2027, now is the time to prepare. Not because something bad will happen — but because preparation gives you options. Retirement doesn’t have to be so...

Jeremy Keil weighs the opportunities and risks associated with giving your money away to your kids and charity. Most retirees I talk with don’t worry about whether they can give money away. They worry about whether they should. When you’ve worked hard, saved diligently, and reached a point where you have more than you need, a new question quietly creeps in: What’s the purpose of the extra? In this episode of Retire Today, I walk through what I see every day in real retirement plans — the good, the bad, and the unintended consequences of giving money to kids and to charity. Because while giving can be deeply meaningful, it can also backfire if it’s not done intentionally. Giving to Kids: Blessing or Burden? When it comes to kids, I hear two very common philosophies. One group says, “I’m not trying to leave money to my kids. If there’s something left, that’s fine.” The other says, “I worked hard for this money, and I want to make sure it helps my family.” Both sound reasonable. But what actually happens is often more complicated. In practice, most giving to kids happens by default, not by design — through inheritance. The problem is timing. If you pass away in your 80s or 90s, your kids are likely in their late 50s or 60s. Statistically, that’s when incomes and net worth tend to be the highest. In other words, that may be the moment they need your money the least. I’ve also seen well-intentioned gifts create unintended pressure. Large down payments on homes can raise a child’s lifestyle without raising their income — leading to higher expenses, more stress, and sometimes less financial stability. Giving feels generous, but it can quietly shift responsibility away from your kids and onto you. A better rule of thumb? Give in ways that remove a burden, not create one. Education costs, health care needs, or meaningful experiences often help without inflating expectations or expenses. Experiences, especially shared ones, tend to create far more joy — for you and for them — than writing a check and hoping it helps. Giving to Charity: Now, Later, or Both? Charitable giving tends to be more intentional, but still incomplete. Many people plan to leave money to charity someday, yet never think through what that looks like or how it fits into their broader retirement plan. Others give modest amounts each year but leave significant sums later — without ever telling the charities involved. What I’ve seen repeatedly is this: When people give with intention, their stress goes down and their satisfaction goes up. In fact, people who have clarity around where their money will go often feel lighter — as if a quiet financial worry has been resolved. When charities know they’re part of your long-term plan, relationships deepen. You stay informed, feel more connected, and often find joy in seeing the impact of your giving while you’re still here. There’s also strong evidence that giving makes people happier. Whether happier people give more, or giving makes people happier, may be up for debate — but in practice, generosity consistently shows up alongside fulfillment. The Bigger Question Isn’t “How Much?” Most people ask me, “How much can I give?” That’s usually the wrong question. The better questions are: Should I give?When should I give?How do I give in a way that actually helps? Giving later through inheritance is easy. Giving earlier — thoughtfully and intentionally — is far more impactful. You get to see the benefit, adjust if needed, and align your money with what matters most to you. In retirement, money isn’t just about security. It’s about purpose. When giving is done well, it doesn’t create regret — it creates meaning. Don’t forget to leave a rating for the “Retire Today” podcast if you’ve been enjoying these episodes! Subscribe to Retire Today to get new episodes every Wednesday. Apple Podcasts: https://podcasts.apple.com/us/podcast/retire-today/id1488769337 Spotify Podcasts:...

Jeremy Keil explains the top 3 tax efficient strategies for charitable giving in 2025. Most people give to charity because it’s meaningful to them — not because of the tax break. And that’s the right mindset. But if you’re already giving, it makes sense to be intentional and structure that giving in a way that helps you keep more of your hard-earned money. In this episode of Retire Today, I walk through the top three charitable giving strategies for 2025, especially in light of new tax rules taking effect in 2026 and important changes already happening this year. With only a limited window left before year-end, now is the time to understand your options. The key is planning — not reacting in April. Why 2025 Is a Unique Giving Year Late in the year, you usually have a clear picture of your income and tax bracket. That makes it the perfect time to decide when and how to give. With upcoming changes like: 0.5% AGI floorcap on the value of deductionsSALT deduction limit 2025 offers an opportunity to be proactive instead of passive. Depending on your income, it may make sense to pull future giving forward — or delay certain gifts until next year. But that decision should be made intentionally, not by default. Strategy #1: Bunch Your Charitable Deductions Bunching means combining multiple years of charitable giving into a single tax year to exceed the standard deduction and unlock itemized deductions. For example, if you normally give $10,000 per year to charity but don’t itemize, you may get no tax benefit at all. But by contributing two to four years of giving in one year, you may be able to itemize and deduct the full amount. The most effective way to do this is through a donor-advised fund (DAF). A DAF lets you: nowlater This separates the timing of your tax deduction from the timing of your charitable gifts — a powerful planning tool when income fluctuates. Strategy #2: Donate Appreciated Investments Instead of Cash One of the most tax-efficient ways to give is donating long-term appreciated investments from a taxable brokerage account. When you sell an investment that has gone up in value, you owe capital gains tax. When you donate that same investment directly to charity (or to a donor-advised fund), you: This strategy is especially effective after strong market years like 2023, 2024, and 2025, when many investors are sitting on significant unrealized gains. To qualify, the investment must be held for more than one year (long-term capital gain). Many custodians automatically select the most tax-efficient shares when processing these donations, making the strategy easier to implement than most people expect. Strategy #3: Use Qualified Charitable Distributions (QCDs) For those age 70½ or older, Qualified Charitable Distributions are often the most powerful giving strategy available. A QCD allows you to send money directly from your traditional IRA to a qualified charity. That money: Many retirees make the mistake of taking IRA withdrawals, depositing the money into checking, and then writing checks to charity. That approach often increases taxable income, affects Social Security taxation, and can raise Medicare premiums — even if a charitable deduction is available. QCDs avoid those issues entirely by keeping the income off your tax return in the first place. Even if you’re not yet subject to RMDs, starting QCDs early can still make sense if part of your regular spending includes charitable giving. Putting It All Together These three strategies often work best in combination: But none of this should be done blindly. The right approach depends on: The most important step is projecting your tax situation before the year ends and making decisions on purpose — not by default. Don’t forget to leave a rating for the “Retire Today” podcast if you’ve been enjoying these episodes! Subscribe to Retire Today to get new episodes every Wednesday. Apple Podcasts:...

Jeremy Keil explores 7 money moves you can consider before the new year to lower your taxes and keep more of your money in retirement. Every December, people scramble to finish holiday shopping, travel plans, and year-end tasks. But one of the most important deadlines — your December 31st tax deadline — often gets overlooked until it’s too late. And once the calendar flips to January 1st, many of the smartest tax moves disappear. In this episode of Retire Today, I walk through seven year-end tax steps you should consider to make sure April brings fewer surprises and more savings. With new tax laws taking effect, the stock market sitting near all-time highs, and contribution limits shifting in the coming years, this is the perfect moment to take control of your finances. 1. Manage Your Tax Bracket Before the Year Ends Your income may fluctuate from year to year — especially in retirement. Some retirees have unusually high-income years due to bonuses, pension payouts, early retirement packages, stock vesting, or unexpected distributions. Others have abnormally low-income years. If you’re experiencing a higher income year, now is the time to pull deductions forward. Charitable giving, donor-advised fund contributions, and other deductible expenses can help lower your taxable income. If you’re in a lower income year, you might choose to accelerate income instead — such as doing a Roth conversion or taking extra withdrawals at a better tax rate. Year-end planning starts with projecting your tax return and understanding which direction to go. 2. Harvest Capital Losses — and Sometimes Gains Even in years when the market is high overall, you may still have individual positions sitting at a loss. Harvesting those losses can offset gains or reduce taxes now or in the future. On the flip side, some retirees find themselves in the 0% long-term capital gains bracket, which creates the perfect opportunity to harvest capital gains on purpose. When you’re in a low tax bracket and gains cost nothing, you can reset your cost basis without additional tax. This is one of the most underused year-end strategies — especially when markets have been climbing. 3. Review Mutual Fund Capital Gain Distributions Many mutual funds issue their capital gain distributions in December. You may not receive the money in cash, but it still counts as taxable income. Look up the estimated year-end distributions from your fund companies and double-check your brokerage account. Mutual fund distributions have surprised many retirees — and they can lead to unnecessary underpayment penalties if tax withholding isn’t adjusted in time. 4. Get Your Tax Withholding Correct Years ago, tax underpayment penalties weren’t a big deal. But with high interest rates today, penalties now operate more like expensive interest charges for not paying taxes in the proper quarterly schedule. If you expect to owe money for 2025, you may want to adjust withholding from your paycheck, pension, Social Security, or IRA distributions. For retirees over 59½, using IRA withholding is one of the easiest ways to catch up — and it is treated as if it was paid evenly all year. To avoid penalties, don’t wait until spring. Make corrections before December 31st. 5. Use Qualified Charitable Distributions (QCDs) If you’re age 70½ or older, QCDs allow you to donate directly from your traditional IRA to charity tax-free. This is often better than taking withdrawals and giving afterward — especially if you use the standard deduction. Even if you’re not yet required to take RMDs, QCDs can reduce your future RMD burden and help you give in a more tax-efficient way. With 2025 bringing updated QCD limits and ongoing rule changes, it’s smart to review your giving strategy now. 6. Make Annual Exclusion Gifts Before Year-End In 2025, the annual exclusion gift limit is $19,000 per person — and it remains the same for 2026. If you’re planning to help your children or grandchildren,...

Dale Hall of the Society of Actuaries explains how to project your longevity and why informed life expectancy matters for retirement planning.

Author Beth Pinsker shares her experience overcoming the challenges of financial caregiving based on her book “My Mother’s Money.”

Jeremy Keil dives into the details of estate planning, what people often miss and how to leave a legacy that lasts.

Paul Merriman shares what his 60+ years of investment experience says about fees, behavior, and building a plan you can actually stick to.

Author Jillian Johnsrud explains how mini retirements help people retire often in this week’s episode of “Retire Today” with Jeremy Keil.

Jeremy Keil compares long-term care insurance to self-funding long-term care through the lens of 3 clarifying questions.

Rona Guymon and Jeremy Keil discuss how the recent economic changes have affected retirement plans and strategies.

Kanwal Sarai of “Simply Investing” explains his 12 rules for dividend investing and how this strategy could be used in retirement planning.

Andrew Motiwalla explains how to prepare for long-term travel and how to incorporate travel into your retirement plan.

Discover how step 5 of building your retirement master plan can help you leave a lasting legacy while avoiding the big 3 retirement risks.

Learn the number 1 investing mistake people make in retirement and how to build a retirement investment plan.

Learn how to keep more of your retirement income through tax planning in step 3 of the 5 step retirement plan.

Learn how to maximize your Social Security and pension benefits in your retirement income plan.

Order your copy of Jeremy Keil’s new book “Retire Today” available now.

Jeremy Keil explains step 1 of the 5 step retirement plan: retirement spending. When it comes to retirement planning, one of the biggest questions people ask is: Where do I start? The truth is, before you think about investments, taxes, or even when to claim Social Security, you need to figure out one thing—how much you’re going to spend in retirement. This is what I call Step One in creating your retirement master plan, which I’ve outlined in my book Retire Today. While many people assume retirement planning begins with assets and income, I believe it begins with spending. After all, if you don’t know what you’ll spend, how can you know how much income you’ll need? Why Many Budgets Fail When I sit down with people, their first instinct is often to start building a retirement budget. They think they need to track every coffee, grocery run, and gas fill-up to get an accurate picture. But here’s the problem—budgets are almost always wrong. People underestimate their spending, forget about irregular costs, and end up thousands of dollars off the mark. I’ve seen it happen time and again. Instead of building from the ground up, there’s a simpler formula that works nearly every time: Income – Savings = Spending. Whatever comes from your paycheck into your checking account typically gets spent—unless you’re intentionally saving it. By starting here, you can find your true monthly lifestyle amount without overcomplicating things. The Story of Thomas Take Thomas, for example. He had what I thought was the best budget I’d ever seen—two years of detailed expense tracking. Every expense logged, every penny accounted for. He proudly told me he spent $7,000 per month. When we broke it down, though, we realized he didn’t need years of tracking to figure this out. His income was $104,000 per year. He saved $20,000 into investments. That left $84,000 for spending—or $7,000 per month. Exactly what his “perfect” budget said, but it took him two years to arrive at something the formula showed in minutes. Don’t Confuse Saving with Growing One caution I often give people is not to confuse saving with growing. If you’re putting $500 into savings every paycheck, but pulling it out later for property taxes or vacations, that’s not saving—it’s managing cash flow. True saving means money you set aside for the long-term, not just for short-term annual expenses. This distinction matters because when you’re projecting retirement spending, you need to know what’s truly ongoing versus what’s temporary or irregular. The Costs People Forget Even when people nail down their monthly lifestyle amount, I often see them forget two of the biggest retirement costs: Health Insurance – Before 65, you’ll likely pay much more out of pocket than once Medicare kicks in. A good rule of thumb is budgeting around $1,000 per person per month, but this varies widely. Taxes – Many retirees underestimate taxes, or treat them like a fixed bill. But taxes are flexible—you can plan, shift, and smooth them over time. That’s why I recommend using tax planning software or working with a planner who can show you different strategies. Don’t Forget the “Non-Lifetime” Expenses Your monthly lifestyle spending is the foundation, but retirement also comes with non-lifetime expenses—costs that won’t last forever, but you should still plan for. These often include: Paying off a mortgage (which eventually goes away). Buying a new car (which will likely happen more than once if you retire in your 60s). Home renovations and repairs (you’ll notice more when you’re home full-time). Big trips and family events. If you don’t plan for these, they’ll sneak up and throw your retirement plan off track. Why Step One Matters Most Retirement is not about hitting a magic savings number—it’s about matching your income to your lifestyle. Step one is figuring out your lifestyle amount: how much you nee...

Jeremy Keil explains why personalized longevity estimates are the most important number in your retirement planning.