Yes, it’s a huge and dense topic because we all know Medicare has to be one of the most unnecessarily confusing things Americans are expected to figure out. And getting it right means understanding what impacts you, personally, this year.

You can do everything right, choose your Medicare coverage carefully, pay your premiums on time, and still get blindsided by something you didn’t know you even needed to ask.

Mark and I covered a lot of ground. We’re grateful so many people tuned in live. These were the four most urgent audience questions that I want to share with you.

1. Medigap is really important. What do you mean I can’t just switch Medigap policies?

First, a quick explanation because this is important. Original Medicare doesn’t pay for everything. You’re generally responsible for 20% of the cost of Medicare-covered Part B services, with no annual out-of-pocket limit under Original Medicare alone. That’s why so many people buy a Medicare Supplement policy, better known as Medigap, to help cover those costs.

Without Medigap, Original Medicare’s 20% has no ceiling. That means a serious illness could leave you with unlimited medical bills for Medicare’s 20% share. But with the right Medigap policy, that huge financial risk can disappear.

Someone in the room asked if her Medigap premiums could go up, and whether she could switch policies during open enrollment.

The short answer is yes, premiums can go up. But Mark explained Medicare’s annual open enrollment doesn’t just give you an automatic right to switch Medigap policies.

In many states, once you’re past your initial enrollment window, an insurance company can look at you differently. They’re able to pick apart your health history before agreeing to cover you. You might have to pay more. You could even be turned down.

Think about that. What if you suddenly developed a health problem, only to discover that changing your supplemental coverage isn’t the simple choice you assumed?

This is exactly the kind of thing you need to know before making your original Medicare decisions. My advice? Before choosing Medicare Advantage or Original Medicare, find out whether you can qualify for Medigap later because, by the time you need it most, the option might be off the table. And do not only choose based on TV ads promising no-cost coverage. That’s a trap!

2. What if I love Kaiser and don’t want to leave?

Another viewer asked a question I loved because it was so practical: If she wants to stay with Kaiser, does she have a choice?

Mark said that a lot depends on where you live. Kaiser offers Medicare Advantage plans in certain markets, and people may have options.

But here’s where I’d be careful. Just because a plan carries the same familiar name doesn’t mean every doctor, facility, or service is covered the same way.

I always say, start with the healthcare you actually need and want. This is highly personal. Then figure out which plan gives you access to it. Not the other way around.

3. I’m healthy. Why should I worry about prescription drug coverage?

An audience member shared that he has Original Medicare and a supplement. He’s not currently taking medications covered by his drug plan. That’s great, but I thought his question was especially important because he’s thinking ahead.

What happens if you do need an expensive prescription in February? Mark shared that you generally can’t just switch Part D plans in the middle of the year because your medication needs changed.

And if you skip Part D altogether without other qualifying prescription coverage, you could face a late-enrollment penalty later.

This is one of those situations where what looks like a smart way to save money today could cost you tomorrow. So the real answer is, even if you take no medications of any kind, compare Part D plans every year and keep qualifying drug coverage in place so you’re protected if your health changes.

4. Is Medicare Advantage always a bad idea?

Joining us live was a retired state employee whose former employer offers a Medicare Advantage plan. He shared that he can see doctors anywhere in the country.

Should he avoid it simply because it’s Medicare Advantage? Not at all! And I’m glad this question came up.

I’ve been pretty outspoken about how ‘salesy’ these Advantage plans are instead of educating people. For that reason alone, there are risks when you choose Medicare Advantage. What I worry about most are all the restrictions that can become painfully apparent when you get seriously sick.

But back to the question. Employer-sponsored retiree plans can be a different animal.

You still need to read through the fine print. Does nationwide access really mean any doctor? What about out-of-network charges and prior authorizations?

And I’d absolutely want this individual to find out if he gives up that employer retiree coverage, can he ever get it back? According to the Kaiser Family Foundation, nine out of 10 Medicare Advantage enrollees 65 and older don’t have a guaranteed right to buy Medigap later.

It’s what the media call, ‘The Medicare Advantage Trap’. Don’t throw away a potentially valuable benefit without knowing the answer.

Here’s What I Took Away From My Conversation With Mark

What bothers me about Medicare isn’t just how complicated it is. It’s that some of the most important consequences aren’t even known until years after you’ve made your decision.

We all know our health changes, our prescriptions change—and who here believes the insurance companies won’t change their plans?

The big problem is that your ability to snap your fingers and change coverage may be limited at a time when you need that flexibility most.

That’s why I wanted to chat with Mark. He’s spent years reporting on retirement and Medicare for publications including The New York Times, and he’s the author of Retirement Reboot. He’s one of those journalists who can explain complicated rules without making your eyes glaze over.

If you missed our conversation, you can watch it now while we’re in this open enrollment period until December 7. We got into a lot more than I could possibly cover here.

And I highly recommend subscribing to Mark’s RetirementRevised. He does terrific work keeping readers informed about the retirement decisions that really matter.

My biggest takeaway? Even if you love your current coverage and assume everything’s the same, take another look.

Because finding out what your plan doesn’t cover after you need it is a lousy way to learn about Medicare.

P.S. If you’re looking for a vetted, fee-only advisor who specializes in retirement planning, connect with us at Wealthramp.

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My media strategist Kelsey and I recently spent a few days in Manhattan. Since my MoneyTrack days on PBS, I’ve enjoyed collaborating with Wall Street journalists who share my mission to help people make better money decisions.

Kelsey lined up several meetings with some of the country’s top financial journalists and kept us moving. My job? Ask good questions, listen to what’s on their minds, answer their queries, and try not to make us late. (We gave NY cabs a good workout).

Our whirlwind included Barron’s, Bloomberg, CNN Business, and The New York Times, plus an interview with Paula Pant of Afford Anything. The Paula Pant interview was on-camera so, yes, I had the hair and makeup squad working overtime.

We squeezed in a dinner at Nobu and Bellinis at Cipriani, too. All business, of course.

But here’s why I’m sharing all this with you.

What Are People Most Worried About Right Now?

At Wealthramp, I’m hearing directly from people wrestling with the same issues financial journalists are investigating.

Inflation has stabilized for now at about 3.4% a year, but grocery and gas prices haven’t gone backward. AI has individuals with retirement plans worrying they have too much money invested in a handful of hyperscaler companies, through stocks and bonds inside their 401(k)s.

Then there’s the push to sprinkle new ‘private investments’ into those same workplace retirement plans. They can be complex, expensive, and difficult for even experts to value. Will they really benefit employees? We know they benefit the brokers selling them.

Which brings me to Ron Lieber at The New York Times.

America’s Top Financial Advisors? Says Who?

Ron and I spent time discussing how consumers choose financial advisors, which is something I care about deeply. It’s also the reason I created Wealthramp.

Our conversation followed the messy recent story involving Forbes and SHOOK Research, the firm behind Forbes’ advisor rankings.

Reports revealed a $6 million payment involving SHOOK’s founder and a former Forbes editor. Forbes suspended its rankings and related events for the remainder of 2026. Remember, Forbes is a 100-year-old respected financial publication.

Both organizations maintain the payment didn’t influence the rankings. Can you see my eyebrow raising?

The whole episode only reinforces what I’ve been saying for years. Why are we ranking advisors instead of carefully vetting them?

We rank restaurants, hotels, and college football teams. Fine. But financial advisors? The best advisor for whom? Ranking financial advisors is like ranking prescription eyeglasses. A thousand people can vote for the best pair in America, but what good are they if you can’t see through them? Your eyesight is unique.

A couple nearing retirement with $500,000 saved? A highly paid executive with stock options? A family running a successful jewelry store? A divorced mom trying to make her money last another 25 years?

They don’t need the same advice, much less the same advisor.

The Problem With Those “Best Advisor” Lists

No one even reports if a No.1 advisor in the US has conflicts of interest, or can know whether they have the expertise to help someone in your particular circumstances.

And here’s something I bet will surprise you. You probably assume those “Best Advisor” rankings are based on investment performance. They’re not. And they shouldn’t be.

That’s because performance shifts with the markets. Performance is fickle and past returns looking in the rear view mirror tell you very little about whether an advisor is right for you.

According to Forbes and SHOOK Research’s own 2026 methodology, rankings factor in how much money advisors manage, the revenue they generate, and how well they retain clients. More than 52,000 advisors were nominated.

My message to Ron was simple. Let’s stop ranking and instead start vetting. Consumers should screen out any advisors with red flags. Then screen in only the ones who fit your priorities.

The financial industry loves rankings, awards, and headlines that scream, “We’re number one.” But the people I talk with want to know whether they can retire, whether their savings will last, and whether they can trust the person advising them.

So the next time a financial advisor tells you they’ve been named one of America’s best, congratulate them. Then start asking the right questions.

Oh, but there’s one thing I can rank: The best Bellini in New York! It’s Cipriani! Hands down.

And I’m perfectly willing to conduct additional research. Andiamo!

P.S. You can always connect with a vetted, fee-only advisor at Wealthramp. Just take our 2-minute survey.

Here’s how they work: You’re placed in a fund with the year closest to when you’re expected to retire—2040, 2050, 2060—and the fund automatically decides how much of your money goes into stocks and bonds. As retirement approaches, it gradually changes that mix to become more conservative, following what’s called a glide path.

A target date fund as a retirement ‘tool’ can get the basic job done, especially for a young employee opening a first 401(k). But it was never built for precision, and precision matters much more as retirement gets closer. Think of this auto-pilot investment option as working like a basic butter knife. You’d never use it to cut into a steak because it’s not sharp.

And this isn’t some obscure little pocket in your retirement plan. Based on the latest plan data and analysis by Vanguard, more than 40 million Americans hold them in their 401(k)s, and probably don’t even remember choosing it because these funds are typically the automatic ‘default’ when employees are enrolled in workplace retirement plans. So there you are, and unless you ‘un-choose’ it, it’s part of your portfolio.

My concern now is that the investments inside these funds are changing automatically, too. Some target-date funds are starting to sneak in annuities and private investments. And this is adding higher fees, less transparency and potential restrictions on accessing your own money.

That’s what’s new, and it’s why I’m trying to get your attention.

How Target-Date Funds Took Over

Target-date mutual funds and collective investment trusts held approximately $5.3 trillion as of June 30, 2026. So today, roughly 85% of target-date assets are held inside workplace retirement plans. That’s according to Sway Research’s mid-2026 report.

Vanguard reports that 96% of the plans it administers offer target-date funds and approximately 84% of participants use them when offered.

But two funds aiming to target the same retirement year may be very different. At retirement, one major provider may hold approximately 40% in stocks, another 50% and another 55%. Some glide paths stop changing at retirement, while others continue changing for decades afterward.

The label tells you the year but doesn’t tell you how much risk you’re taking.

Now Meet the CIT

Employers have faced years of pressure to reduce 401(k) fees. That helped accelerate the movement from traditional mutual funds into collective investment trusts, or CITs, which can offer similar investments at a lower cost.

CITs now hold 55% of target-date assets, again according to Sway Research, overtaking mutual funds as the dominant vehicle. They are regulated, and employers remain responsible for selecting and monitoring them under ERISA. But CITs aren’t registered with the SEC and don’t have the same public disclosure, reporting and liquidity requirements as mutual funds.

Bloomberg recently reported that no one can say definitively how large the overall CIT market is or exactly how all its assets are allocated. That’s remarkable when trillions of dollars in retirement savings are involved.

This shift matters because CITs are expected to become a primary route for introducing annuities and private investments into target-date funds.

Annuities Are Already Moving In

More than a dozen target-date series now offer some form of guaranteed retirement income. Morningstar reports that assets in target-date funds with embedded annuities reached $44 billion in March 2026, up nearly 70% from $25 billion a year earlier.

BlackRock already offers LifePath Paycheck, Vanguard has announced lifetime-income target-date trusts, and Fidelity plans to introduce Freedom Lifetime in early 2027. Fidelity’s version will allow eligible participants to convert up to 25% of their target-date balance into guaranteed lifetime income.

An annuity may be appropriate for some retirees. But committing part of your savings to guaranteed income can involve costs, complicated terms and a loss of flexibility. That deserves an individual decision—not something that simply arrives inside a default investment.

Private Investments Are at the Gate

BlackRock and Great Gray Trust are developing a target-date solution that could allocate between 5% and 20% to private equity and private credit, depending on the participant’s age. Franklin Templeton has already introduced target-date products with smaller allocations to private real estate and private credit.

BlackRock estimates that private investments could add half a percentage point to annual returns and produce a retirement balance approximately 15% larger over 40 years. Those are projections from the company offering the product—not guaranteed results.

Private investments may provide diversification and higher returns. They can also bring higher fees, limited liquidity, infrequent valuations, difficult performance comparisons and less transparency than publicly traded stocks and bonds.

The Department of Labor has proposed a safe-harbor framework that could give plan sponsors greater legal protection when adding alternative assets to diversified retirement funds. It is only a proposed rule, but it could remove one of the largest barriers preventing employers from adopting them.

Why It Really Is a Trojan Horse

Target-date funds are the perfect delivery system because they’re already the automatic default for millions of workers. An employee could gain exposure to an annuity, private credit or private equity without ever affirmatively choosing it.

Jason Lilly, a CFA and financial adviser in the Wealthramp network, believes target-date funds can work well for younger investors because they provide diversification, rebalancing and oversight. His biggest concern is the glide path, which may move in the wrong direction for an individual client—especially near retirement, when control, liquidity and flexibility matter most.

Connect With a Vetted Advisor

What You Should Do

You don’t need to abandon your target-date fund tomorrow. You do need to look under the hood:

• Find out whether your fund is a mutual fund or a CIT.

• Check its stock-and-bond allocation, glide path and total fees.

• Ask your plan rep whether an annuity, private equity or private credit has been added.

• Within five to 10 years of retirement, treat any illiquid investment or annuity conversion as an individual decision—not autopilot.

Remember that a target-date fund, no matter what’s added to it, is still an investment product. It is not a retirement-income plan, and it was never built to know the difference between your situation and the next person who happens to share your birth year.

A default is only useful when you understand what it defaults you into. Right now, that default is becoming more complicated, less transparent and potentially harder to unwind—and most employees have no idea it’s happening.

P.S. Have you ever wondered what the alphabet soup of financial advisor credentials actually means? Here’s what you need to know about CFA, CPA, CFP, CIMA, and a host of other financial designations.

I was reminded of this just as I read about the awful case involving Siddharth Jawahar. The former investment adviser behind Swiftarc Capital pleaded guilty to wire fraud after stealing millions of dollars from clients. (Travis Kelce and several NBA players were named among the victims). Jawahar wasn’t paid commissions for selling products, but he could earn extra money when the investments he managed made money. For me, that’s a huge red flag, and if I saw that on an advisor’s SEC filings during my vetting process, they’d be rejected then and there. Those are called ‘performance fees,’ and that tells me this advisor is incentivized to take on more risk.

Jawahar was recently sentenced to 11 years in federal prison and ordered to pay $31.35 million in restitution. He raised more than $35 million from investors through Swiftarc, but only about $10 million was actually invested. The rest? Private jets, luxury apartments, and a very expensive lifestyle.

It never ceases to amaze me that these con artists operate this way in full light of day — soliciting investors, filing regulatory paperwork and running what looks like a legitimate advisory business — for years before anyone catches on. Research tracking Ponzi schemes prosecuted by the SEC found they run for roughly four years on average before collapsing. Even after regulators step in, victims often recover only a fraction of what they lost.

So does this undermine what I’ve been telling investors for years about seeking fee-only fiduciary advice? No. But it raises an important question: What protection does being fee-only and fiduciary actually give you?

I’ve been doing this for three decades. I’ve seen brokers who should have been held accountable for recommendations that hurt investors. And I’ve spent years working closely with fee-only fiduciary advisors. From personal experience, I will tell you there is a difference between those two groups, and prospective clients need to understand that the difference is already baked into the cake before you ever become a client.

Imagine this happened to you

Say you have $500,000 saved for retirement and a broker recommends putting $250,000 into an annuity. Later, you figure out the huge costs embedded right in the product, commissions (you pay) connected to the sale, and surrender charges that make it expensive or even impossible to access your own money for years. Now you’re asking: Why was this annuity recommended to me?

Someone will inevitably say, “But brokers have Regulation Best Interest now.”

Yes, but…

Reg BI requires brokers to consider risks, rewards and costs, and to have a reasonable basis for believing a recommendation is in the customer’s best interest. But Reg BI did not fundamentally change the burden an investor faces when seeking damages.

In the real world, if you bring a claim against your broker in FINRA arbitration, say for recommending that annuity without knowing all the facts, you’re the claimant. In most cases, it’s on you to prove by a preponderance of the evidence that you were financially harmed and that the brokerage advisor was responsible. Good luck with that—brokerage agreements commonly contain predispute arbitration provisions, meaning you’re usually not getting your proverbial day in court.

Reg BI changed the standard governing a broker’s recommendation. It did not flip the burden and require the brokerage firm to prove that its recommendation was appropriate simply because you challenged it.

That’s part of what’s baked into the cake. You’re choosing not only a financial advisor but the compensation structure, conflicts, legal obligations and dispute framework that come with that relationship. Please let that sink in.

Now change the relationship

With a fee-only fiduciary advisor, there’s no commission waiting on the other side of that annuity sale. The advisor also has a legal duty to act in your best interest. After 30 years watching advisors work under these different structures, I’ve seen that accountability matters. Advisors tend to be more careful about what they recommend, what they charge and the conflicts they avoid.

Does that guarantee a good advisor? Not even close.

And yet, a fiduciary can still be a dangerous crook

That’s the lesson from Jawahar. Fee-only isn’t a character reference, and fiduciary isn’t a background check. Someone determined to steal your money isn’t going to be stopped by a fiduciary oath.

And this is exactly why vetting matters so much.

At Wealthramp, we don’t take someone’s word for it because they say they’re a fiduciary or have CFP® after their name. We dig into how they’re paid, whether they sell products, their regulatory and complaint history, what their Form ADV tells us, and who actually holds the client’s money. Then I want to understand how they think. What would you do with a difficult client situation? What wouldn’t you do? Where does your expertise end? When would you bring in someone else?

You learn a lot about an advisor by asking questions that don’t have a checkbox answer.

The real protection is layers

While most of us will hopefully never encounter a Ponzi scheme, there are other things to watch out for. The perfectly legal investment that may be completely wrong for you. The annuity that locks up half your retirement savings when you need liquidity, the expensive investment you don’t understand, or the recommendation influenced by a commission, or the advice that comes without any context because context isn’t necessary in order to make a ‘sale.’

I don’t believe one label can protect you. You want layers: remove unnecessary financial conflicts, work with an advisor who accepts fiduciary accountability, independently vet the person behind the credentials, and keep your assets with a reputable independent custodian.

None of that guarantees you’ll never encounter a crook. But in my experience, I think the fiduciary legal standard difference matters.

P.S. For a primer on fiduciary advisors, check out the latest video in my “Decoding Financial Advisors” series on YouTube.

A lot as it turns out.

My expectations were out of whack with the reality of owning and managing a rental. Expenses I never anticipated. Tenants who were twice my age and seemed responsible simply stopped paying the rent. (One was an accountant!) Being a landlord required more time and attention than I expected. Things just got away from me fast.

And it happened in a housing market where I should have made a nice profit, yet I didn’t make a dime.

Great lesson. And I guess I’m glad I learned it first hand. Fast-forward to today and I see people making some of the same assumptions I did back then. Now I want to help them avoid it.

Imagine you buy a rental property to earn some passive income and enjoy the long-term asset appreciation. And say you find a great tenant who pays you $2,500 a month. It’s really easy to look at that rent check and think: Wonderful, I now have a dependable $30,000 a year coming in.

Then the tenant moves out and it takes six weeks to find another one. Meantime, an appliance needs replacing. Your insurance premium rises, property taxes go up, you realize you need more landscaping, and suddenly a big chunk of that $30,000 income has evaporated.

The rent is easy to see. What you actually keep after paying those expenses tells you whether you really have a good investment.

And this year, you have less room for math mistakes. Rental property investors bought 6% fewer homes in the first quarter than a year earlier, according to Redfin, putting purchases at their lowest level since 2020. Financing is still stubbornly expensive, too: the average 30-year fixed mortgage rate was 6.65% as of August 20.

You can absolutely build wealth owning rental property. I might have had a very different ending to my own story if I’d gone in knowing then what I know now.

So what should you know? I asked Dave Rowan, CFP®, MBA, a fee-only advisor in my Wealthramp network who works with clients considering real estate investments, to walk me through it.

Start With What You Want the Property to Do

There are several ways to profit. But long-term rentals are different from short-term rentals, which are different from a house flip. These are very different businesses. Before you start looking at properties, Dave says, get clear about what you’re trying to accomplish.

• Do you want to generate income now?

• Are you mostly interested in appreciation over the next 10 or 15 years?

• Are tax benefits part of the attraction?

• Do you want one property or eventually a larger portfolio of properties?

Dave recommends developing a “buy box” before you start shopping: the type of property you want, the numbers that have to work, how much you can spend on improvements and the locations you’ll consider.

Otherwise, it’s too easy to find a house you love and start bending the numbers to justify buying it. Been there.

Find a Vetted Advisor at Wealthramp

What Has to Go Right to Make Money?

A rental can make you money through rent, appreciation, tax benefits and the equity you build as the mortgage gets paid down. The important part is knowing which of those you’re counting on.

A property with even modest cash flow in a growing market might make sense if you’re investing for appreciation over 15 years. It could be a terrible choice if you need reliable income today.

Run several scenarios before you buy. What if rents stay flat? What if appreciation is slower than you expected? What if you have to sell sooner? And keep cash in reserve. If the AC quits in July, your tenant doesn’t care whether it’s a convenient month for you financially.

A property manager can help, but you’re still the owner.

“Hiring a great property manager can take a lot off your plate as a landlord,” Dave says. “However, you’ll still need to keep good books, make calls on repairs and improvements, and deal with added complexity on your tax return.”

The Myth About Rental Property Tax Breaks

Rental property often gets pitched as a two-for-one: make money on the property and get valuable tax breaks. But how much are those benefits actually worth to you?

Depreciation can be valuable, but taxes get complicated quickly. Rental real estate is generally treated as a passive activity for federal tax purposes, and rules can limit whether rental losses can offset other income. Your income, level of participation and individual tax situation all matter.

That’s why I wouldn’t buy a mediocre property because somebody told you the “tax write-offs are amazing.” Start with whether the property itself is a sound investment, then have a CPA explain what the tax benefits actually mean for you.

Explore a One-Time Financial Plan

Put the Property to the Test

“Real estate can be extremely rewarding in terms of cash flow, property appreciation, potential tax benefits and doing something entrepreneurial,” Dave told me. “However, investing in real estate well requires significant time and effort. It is definitely not a passive activity.”

And the math absolutely can work. Cleveland is one example of a market where relatively affordable home prices paired with solid rents can produce attractive gross rental yields. But gross yield is the headline number. What you keep after taxes, insurance, vacancies and upkeep is what counts.

Dave has seen people buy their first property and sell within a few years because they underestimated what they were taking on. He tells first-time investors to expect to look at a lot of properties, possibly in several locations, before making an offer.

When you find one you like, stress-test it. Assume everything doesn’t go exactly according to plan and run the numbers again.

That’s the part I skipped in Boulder all those years ago. I bought with expectations instead of enough experience. It was a great lesson, and I never forgot it.

Rental real estate can be a terrific way to build wealth when you buy the right property for the right reasons. Just do the math first.

P.S. Check out the latest episode in my “Decoding Financial Advisors” series, now on YouTube!

I care about that moment because it’s when the lightbulb goes on and you understand what good financial advice is supposed to look like. You can’t look at that relationship the same way again.

I’m sharing my backstory because there’s a pretty straight line from what I saw early in my career, to creating the weekly MoneyTrack TV series seen on PBS stations nationally, to eventually building Wealthramp.

Something I Couldn’t Unsee

Early in my career, I was smack in the middle of the aggressive sales culture that rules the brokerage industry. Some of the broker-advisors I managed were good people but already settled into a really bad system. They were trained enough to “sell” whatever the brokerage firm made commissions on, but not qualified to give financial advice – let alone offer tax planning or investment strategy.

The moment that changed my career was when I watched two advisors I managed push annuities onto a cognitively impaired man in his late 80s, then celebrate the big commissions they earned. And I was supposed to defend that behavior. I thought, “Oh no, what have I done?” And I remember thinking: this can’t be real, there has to be real financial advice out there.

MoneyTrack Changed Everything for Me

My next role gave me an insider’s look at how real advisors operate. These are independent advisors. When an advisor wasn’t selling a particular product where you are paying a big commission, I saw the difference. I met with thousands of highly qualified fiduciary, fee-only financial advisors and learned that there’s a lot more to becoming an exceptional financial advisor, and fee-only and fiduciary don’t always make somebody exceptional.

Fast forward to 2005. I decided to create the weekly MoneyTrack TV series to educate Americans about how to save, manage and invest better. We aired for three seasons on more than 250 PBS stations. I wanted a big audience to get realistic financial education but not turn it into a boring business show about Wall Street. It had to be personal finance. We featured real people, respected experts and a good dose of humor. My Labradoodle, Chloe, was running around on set. MoneyTrack became a huge part of my life and my story, and I’m proud to say I won two prestigious Gracie Awards.

And because that mission resonated with legendary investing experts like John Bogle, Jeremy Siegel, Ben Stein and, yes, Warren Buffett, they all agreed to appear on MoneyTrack. In fact, John Bogle became a regular guest, and I later interviewed him for the one-hour special An Evening with John Bogle where he explained the financial crisis of 2008.

Together, our message was consistent: people deserve better advice, not sales for insurance. They need full transparency. The fact is there are simply too few truly outstanding fee-only financial advisors. In my opinion, there are only about 5,000 financial advisors in America who I can call exceptional fiduciaries. That’s out of more than 350,000 financial advisors, including the brokers and insurance agents who call themselves advisors.

And that’s where MoneyTrack eventually turned into Wealthramp.

MoneyTrack could teach you what to look for, what questions to ask and how to protect yourself. But viewers kept telling me: the show couldn’t say which advisor to trust.

Even if I taught you every right vetting question to ask, how were you supposed to know who was actually great at what they did? And who would really understand you, instead of fitting you into the same system they use for everybody else?

So along came Wealthramp.

Most People Don’t Know What They’re Missing

Thanks to an industry built entirely around sales and marketing instead of financial advice, most people have never experienced truly outstanding financial advice. They don’t even know what it looks like.

Great advice goes much deeper than managing money because a great advisor understands what the money is supposed to do for you, what scares you, what matters to you, where you can afford to take risk and where you absolutely cannot. Two people with exactly the same amount of money can need completely different advice because they have completely different lives.

That’s why one-size-fits-all financial advice drives me crazy. One product can’t possibly know you. The best model portfolio still can’t know you. And a free oline retirement calculator looking at your age and account balance can’t know you.

The best advisors I’ve met start by listening to you. Sometimes great advice means telling someone to spend less. Sometimes it means telling someone who has spent a lifetime saving that they can finally spend more.

Why I Personally Vet Every Wealthramp Advisor

People sometimes ask why I’m so involved in the vetting. Why not screen for credentials, experience, fee-only status and a clean regulatory record and leave it at that?

Because that’s not enough for me. I want their backstory. Why did this person become an advisor? How do they actually work with clients? What happens when a client is scared, grieving or about to make a decision the advisor thinks is a mistake?

I’m listening for what doesn’t show up on a résumé. What would it actually feel like to work with this person? Will they really listen? Will they notice the details? Will they be there when life changes and the original plan no longer fits?

Ultimately, I’m asking one question: would I trust this advisor with someone I care about? If the answer isn’t an emphatic yes, they don’t belong in Wealthramp. After all, my name is on every advisor recommendation so it’s like someone’s hiring me directly.

This Is Why It’s So Personal

At this point in my own life, I understand what it feels like when the runway isn’t endless anymore. Life changes, decisions have consequences, and what mattered at 45 can look very different later.

I think everybody deserves an advisor who understands that—especially people who have worked for decades, saved diligently and built a good life, but not so much that a major mistake doesn’t matter. That’s who I’m thinking about when I interview an advisor.

I can’t make the entire financial services industry behave the way we all wish they would. But I can do my small part: help people understand what great financial advice should look and feel like, and find advisors who meet the standard I would want for myself and for the people I love.

And that’s how an educational TV series called MoneyTrack became Wealthramp. The mission never changed. It’s to help people understand what good financial advice really looks like, and make sure they can actually find it.

P.S. I’ve just created a new series, “Decoding Financial Advisors,” on YouTube. In every episode, I’ll explore different aspects of selecting the right financial advisor to meet your needs. I’d love for you to check out the first episode here and let me know what you think.

I’ve already written on one of the biggest misconceptions about S&P 500 index funds, which is that you can own 500 stocks and still not be as diversified as you think. Today just 10 big companies represent almost 40% of the traditional S&P 500.

This happens because your S&P 500 index fund is probably market-cap weighted, which means the bigger a company gets, the more of it you automatically own. So as the giant AI stocks have soared in value, they’ve become a bigger and bigger share of your fund, whether you want to make a bigger bet on AI or not.

I’m talking about all the big AI players like Nvidia, Microsoft, Alphabet, Amazon and Meta that have propelled to enormous valuations, and that’s been great for investors who own them. But you may look at those companies and think you own several very different businesses, not realizing a lot of their growth is increasingly tied to the same underlying story: massive spending on AI, data centers, chips and computing power, and a ton of borrowing to make these ginormous AI bets pay off.

If all that investment does keep paying off, it’s fantastic. But if expectations get ahead of reality, several of your biggest holdings could get hit at the same time.

None of this means you should dump your S&P 500 fund. These companies became such a huge part of the index because their values soared, and if they can keep outperforming, having more money in them can keep working in your favor. The problem isn’t concentration by itself. But if you don’t know what your holdings are, well . . .

Start by looking under the hood. Look at your S&P 500 fund, your growth funds and your tech funds and see how much overlap you actually have. Then, if you decide you’re not diversified, consider another approach.

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There’s another way to own the S&P 500

It’s called equal weight.

Instead of letting the biggest companies take up more and more of the index, an equal-weight fund gives every company roughly the same weight, about 0.2% when the fund rebalances. You still own Nvidia, Microsoft, Apple, Amazon and the rest of the giants. You just own a lot less of them and a lot more of the other companies in the index.

The Invesco S&P 500 Equal Weight ETF, ticker RSP, just crossed $100 billion in assets, 23 years after it launched. That doesn’t mean investors have discovered a “better” S&P 500, because there is no better version for everyone. But $100 billion is a pretty good indication that investors are paying attention to concentration risk.

So far in 2026, the equal-weight S&P 500 was up about 16.1% versus 13.5% for the traditional cap-weighted S&P 500. In other words, recently the rest of the S&P 500 has actually been outperforming the version dominated by those mega-cap giants.

Again, I’m not saying sell your existing index funds just because you’ve discovered AI creep in your portfolio. But do consider directing any new investment money differently.

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What do you gain, and what do you give up?

The obvious benefit of equal weight is less concentration. Instead of having close to 40% of your S&P 500 money riding on 10 companies, your money is spread much more evenly across all 500. The other 490 stocks suddenly have a much bigger opportunity to affect your returns.

There’s also a built-in discipline to equal weighting. The funds periodically rebalance, trimming stocks that have gotten bigger and adding to stocks that have gotten smaller. That sounds pretty appealing, but remember what it also means, that you’re deliberately trimming your winners.

If Nvidia, Microsoft and the other mega-cap companies keep outperforming, the traditional S&P 500 could continue to beat equal weight. A cap-weighted index lets its winners run and become bigger and bigger pieces of the portfolio. Equal weight keeps cutting those winners back down to size every time it rebalances.

Equal weight also gives you more exposure to the smaller companies within the S&P 500, and equal-weight funds generally cost more than the rock-bottom fees available on traditional S&P 500 index funds.

You don’t have to choose

This is the part I think investors sometimes miss. You don’t have to pick one version of the S&P 500 and declare it the winner. You can own some of each.

If you’ve built up a big position in a traditional S&P 500 fund and you’re uncomfortable with how concentrated it has become, adding some equal-weight exposure is one way to dial that concentration back without walking away from the S&P 500. But before you do that, look at your whole portfolio, because you may already own mid-cap, small-cap or international funds that give you plenty of diversification away from those giant U.S. companies.

Or you may discover exactly the opposite. You own an S&P 500 fund, a growth ETF and a technology ETF, and all three are loading you up on many of the same stocks. That’s why counting the number of funds you own is not the same thing as being diversified.

So don’t change your portfolio just because somebody tells you the S&P 500 is too concentrated. First figure out how concentrated you are, including how much AI creep has worked its way into funds you already own. Then decide whether you’re comfortable with it. If you’re not, equal weight is one way to do something about it.

P.S. Financial plans work best when they’re tailored to you. Connect with Wealthramp’s network of vetted, fiduciary advisors anytime.

One theme we talked about a lot was which investing strategy gives the greatest number of people the best chance of succeeding over a lifetime. We weren’t talking about which horse to bet on today, or which private equity fund manager might beat the S&P 500 next year. Bogle was interested in something much bigger: What can an ordinary investor do consistently for 20, 30 or 40 years that works? (You can watch our conversation below. You’ll have to excuse the video quality—it’s from 2009!)

One of his great investing lessons summed it up beautifully: “Time is your friend. Impulse is your enemy.” Bogle’s point was to take advantage of time and compounding and resist the temptation to react to whatever the market happens to be doing right now.

The more time I’ve spent hearing from individual investors, the more convinced I’ve become that one of the most brilliant investing strategies ever devised is also one of the simplest.

It’s called dollar-cost averaging, and there’s a pretty good chance you’re already doing it. If money comes out of your paycheck and goes into your 401(k) every two weeks, you’re dollar-cost averaging. You may also be doing it automatically in an IRA or brokerage account. Month after month, year after year, your money goes into the market without requiring you to decide whether today is the right day to invest.

I’ve always believed that’s incredibly powerful. But I’m the first to admit, looking at only the math, dollar-cost averaging isn’t the actual winner.

Why Investing a Lump Sum All at Once Makes More Money

Suppose you have $12,000 in cash ready to invest. You can invest it all now, or phase it in at $1,000 a month for the next year.

For illustration, let’s assume the market earns a smooth 8% over those 12 months. Invest $12,000 on Day 1 and you’d finish with about $12,960. Invest $1,000 a month while the rest waits in cash earning nothing, and you’d end up with roughly $12,500.

Vanguard’s research backs up the principle: lump-sum investing beats gradually phasing available cash into the market roughly two-thirds of the time. From 1976 through 2022, Vanguard found U.S. stocks outperformed cash 76% of the time.

But there’s a crucial distinction. This applies when you already have the $12,000. If you’re earning $1,000 of investable money each month and investing it immediately, you’re putting each new dollar to work as soon as it’s available.

So why am I such a fan of dollar-cost averaging when the math favors investing a lump sum? Because the math behind lump-sum investing assumes we’ll behave ourselves.

But Math Meets Real Life

Instead of $12,000, imagine you’ve inherited $500,000 and invest it all today. Three months later the market falls 25%, and you’re looking at a statement that’s down $125,000.

What are the odds you’ll calmly leave it alone? Let me show you.

DALBAR has studied investor behavior for more than 30 years. In 2024, the S&P 500 returned 25.02%, while DALBAR calculated that the average equity investor earned only 16.54%. That’s an 8.48 percentage-point gap. Investors withdrew money from equity funds throughout the year, with the largest outflows occurring shortly before a major market surge.

That’s the problem dollar-cost averaging is really good at solving.

Dollar Cost Averaging: The Real Advantage Factors in Your Behavior

Think about someone who’s been putting $500 into a 401(k) every two weeks for years. The market drops 25% and, yes, the account balance hurts. But the process doesn’t change. Another contribution goes in, and because stocks are cheaper, it buys more shares.

Dollar-cost averaging turns investing into something that can happen almost invisibly in the background of your life. You don’t have to decide whether this Tuesday is a good Tuesday to buy stocks or wait for the Fed, an election or the next inflation report to tell you it’s safe. If you have 20 or 30 years before you’ll need the money, lower prices mean your new contributions buy more shares.

That’s dollar cost averaging’s enormous psychological edge. It helps you keep doing the one thing long-term investors (and even the pro’s) don’t do well: stay invested.

Of course, automatic investing doesn’t mean you’ll never get anxious or need advice as life changes. This is where a good fee-only fiduciary advisor can make a real difference, helping you build a portfolio you can actually live with and stick with it when the market gets ugly.

Even Vanguard acknowledges this behavioral tradeoff. Its research says gradually investing a lump sum can make sense for highly loss-averse investors who might otherwise leave the money sitting entirely in cash. For that person, the math strategy that comes in second place could produce a better real-life result because it gets them invested and helps them stay there.

Yes, The Tortoise Still Wins

Dollar-cost averaging isn’t magic and it’s not even exciting. It can’t turn a bad investment into a good one or protect your existing portfolio when markets fall. That’s why it belongs inside a broadly diversified, low-cost portfolio appropriate for your goals and time horizon.

Think of the old tortoise and the hare. The hare is jumping around trying to hunt down the next great stock, moving into last year’s winning fund, raising cash because a correction is coming and figuring out when it’s safe to get back in. His problem is that he has to keep being right, as in, every time right.

The tortoise owns a diversified portfolio and just keeps building it.

So yes, if you hand me $500,000 today, tell me you’re comfortable with market risk and ask what history says, I’ll tell you to get the money invested. Lump sum wins the math most of the time.

But give me 30 or 40 years of bull markets, crashes, recessions, recoveries and scary headlines, and I’ll ask a different question: What strategy gives you the best chance of actually successfully staying invested through all of it?

That’s why, after all these years, I keep coming back to dollar-cost averaging. John Bogle had it right. Time is your friend. Impulse is your enemy.

P.S. I had a great conversation recently with Next Gen Personal Finance podcast about retirement risk, fiduciary advice, and a few of my favorite John Bogle stories. Check it out here.

All three involve a parent who died with assets left behind and adult siblings fighting over an inheritance that was unclear, felt unfair — or both.

The details are different, but the arguments sound remarkably similar. Why did she get more? Dad told me something completely different. Mom already gave him money years ago. Who gets the house? Was Dad really capable of making that decision by then?

These aren’t little disagreements that are going to blow over. The wounds are deep, and I honestly don’t know whether some of these sibling relationships will ever recover.

So if you have adult children, hear me on this: Don’t assume they’ll work it out after you’re gone.

Talking about money with your kids can be terribly awkward, especially if you’re considering leaving them different amounts. But leaving them to interpret your decisions later can be much worse.

Equal Can Get Complicated Fast

Two children? Fifty-fifty seems obvious. Three? One-third each. For plenty of families, that’s exactly right.

But life isn’t that neat. One child may be financially secure while another is struggling. You may have paid for one child’s graduate school or helped another buy a house. One may have spent years helping you while the others live across the country.

Imagine you have two children and $600,000 to leave them. One is financially secure. The other is a single parent who has struggled to save. The clean answer is $300,000 each.

But maybe $400,000 and $200,000 would give both children greater financial security. Now sit in the successful child’s chair: I worked hard and saved — and now I’m getting less because I succeeded?

There’s no formula for this. You need to know why you’re making the decision and be able to explain it. Here’s the disconnect: 97% of families say talking about estate planning is important, yet nearly half still haven’t had those critical conversations. That’s according to Fidelity’s research.

The “Daughter Tax”

There are some differences you shouldn’t ignore, though, and caregiving is a big one.

There’s even a name for the financial toll that so often falls on daughters: the “daughter tax.” It’s what can happen when one daughter becomes the default person taking Mom to appointments, handling emergencies, paying expenses and perhaps cutting back at work.

Then Mom dies and the will says everything gets divided equally.

Maybe that’s exactly what Mom wanted. But what if she repeatedly told her daughter, Don’t worry, I’ll take care of you. What if that daughter spent thousands of her own money assuming she’d eventually be reimbursed?

Now she’s saying, I gave up years of my life and spent my own money taking care of Mom. Her siblings are saying, The will says we split it equally.

You can see how fast this goes sideways.

Before Any Inheritance, There’s Mom and Dad

Here’s what I believe parents should stop and consider. Before spending too much time mentally dividing your assets among your kids, ask yourself: What if I need that money? Because this is where I see things falling apart.

What if you or your spouse will need in-home care? Assisted living or memory care costing $9,000 a month? A bathroom remodeled so you can stay in your house? Who is funding all this? Which assets will you use? Who takes over the finances if you can’t?

My friend Beth Pinsker, a CFP and MarketWatch columnist, wrote My Mother’s Money: A Guide to Financial Caregiving after managing her own mother’s finances and care. At one point, her mother’s caregivers cost about $12,000 a month. As Beth put it, “There’s not a lot of fortunes that will sustain $12,000 a month” just for caregiving.

There may be a lot less inheritance after you pay for your own care. There may be none. And that’s okay. It’s your money, and your care comes first.

And that’s actually the conversation I’d have with the kids: Here’s how Dad and I plan to pay for our care. Here’s who will handle the finances if one of us can’t. Here’s what we may need from you — and what we don’t.

Then update that conversation as life changes. Now everyone is used to talking about money, care and responsibilities before there’s a crisis. And if there is an inheritance someday, it’s what remains after you’ve taken care of yourselves.

Don’t Confuse Money With Love

To you, dividing what remains may be a financial decision. To your kids, it can feel like one final message from Mom or Dad.

“Sarah needs more help,” can be heard as “Mom loved Sarah more”. And sometimes the fight isn’t even about money. It’s Dad’s watch, Mom’s ring or the family house.

You don’t have to disclose your net worth or exactly what everyone will inherit. But if a decision could surprise somebody, explain it while you’re still here.

The Right Advisor Does More Than Manage Investments

A good fee-only financial advisor can be a neutral financial decision partner. Your advisor isn’t your attorney. But he or she can model what several years of care might cost, help you think through different choices without all the family emotion attached, and help you communicate what you’ve decided. Then your estate attorney can make sure it’s properly documented.

So don’t start with, What am I leaving my kids? Start with, How am I going to take care of myself? What do I want my kids to know? Who will do what if I need help? And what can I decide now so they aren’t left guessing later?

And whatever you ultimately leave them, try to leave one more thing intact: their relationship with each other.

I keep coming back to my three friends. To my friends who are parents with their own adult kids: Have these conversations now, while you can. Don’t leave your kids to guess what you meant later.

And to my friends who are the adult kids already in the middle of this: I hope when the money and the legal fights are over, you can find your way back to each other. Because that relationship may ultimately be worth far more than whatever you’re fighting over.

If you’d like to explore how a vetted, fiduciary advisor can help you navigate these financial decisions, you can access Wealthramp’s network anytime.

By cookie-cutter, I’m talking about financial guidance that’s designed to work reasonably well for lots of people rather than being tailored to one person. You can call it financial education. By design, it’s informational and intended to answer a general question, not account for your entire financial life.

You can find general answers to your money questions practically everywhere, usually for free: articles, TikTok (including mine!), YouTube videos. You’ve likely seen ads promoting free retirement calculators and super-low-fee robo-advisors.

But cookie-cutter guidance isn’t limited to online tools. You can also get it from representatives at banks, insurance companies, and discount brokerage firms who rely on standardized models and approved recommendations rather than advice built around your unique circumstances. Some are salaried, others are paid through commissions built into the investments they recommend, but the common thread is the same: the guidance is designed to fit lots of people, not you. (If you’ve been following Count Up for awhile, you already know this is one reason I recommend fee-only, fiduciary advisors instead).

I sound a little judgy, so I want to be fair and acknowledge there are plenty of situations where that kind of guidance is just what you need.

If you’ve never budgeted before, “save three to six months of expenses” is a perfectly good place to start. If you need a gut check rather than a financial plan, “100 minus your age” gives someone with no other information a rough stock allocation to react to. If you’re looking for one number to anchor a conversation, saving 15% for retirement or following the 4% rule gives you something to work with. In other words, it’s a starting point. It can be really useful.

And maybe your financial life really does look exactly like the assumptions behind the rule, perfectly steady income, straightforward finances, no pension, no business to sell, no complicated tax issues, no family money challenges, so the generic answer might end up being pretty close to the right one.

When Generic Stops Being Good Enough

The trouble starts when your life stops looking average, or you decide you really do need financial advice because now it’s serious, and generic won’t help and, in fact, could really harm you.

Maybe you’re planning to sell a business. Or you’ve inherited money, are getting divorced, have a pension, startup stock options, aging parents, or a child who needs lifelong financial support. Then suddenly, the one-size-fits-all advice you’ve relied on has no idea who you are or what you’re trying to accomplish.

The same thing happens when market conditions change. Bill Bengen developed the 4% withdrawal rule after studying some of the worst retirement periods in history. It was never intended to be a one-and-done prescription. He adjusted withdrawal strategies as his clients’ lives and market conditions changed.

I see lots of people treat it as if it’s the answer, and then get thrown for a loop when the stock market drops or the price of gas goes up.

Researchers like David Blanchett have shown that changing interest-rate assumptions alone can dramatically change the odds that a 4% withdrawal strategy succeeds. Michael Kitces has pointed out the opposite problem: for many retirees, following it too rigidly can leave hundreds of thousands of dollars unspent that could have been used to enjoy retirement.

Same rule. Different people. But totally different outcomes because rules of thumb can’t make judgments. They’re supposed to be used broadly, not for specific advice.

Advice is different because life is different. Markets change. Tax laws change. Families change. Health changes. Good financial advice takes those moving pieces into account. A rule of thumb deliberately ignores your circumstances so it can apply to millions of people. That’s not a flaw—it’s exactly what makes a guideline or rule useful. But it’s also why rules sometimes need to be broken to arrive at advice that’s truly personalized.

It’s the same limitation with most robo-advisors. They ask a handful of questions, sort you into an investment model, and generate recommendations based on broad assumptions. That’s useful technology, but it isn’t the same as sitting down with someone who’s looking at your entire financial life and knows you (and your habits).

Real fiduciary financial advice has to start with you—your taxes, your retirement income, your family, your health, your values, and the tradeoffs you’re constantly facing. This is judgment, not just formulas. Sometimes there just isn’t one right answer. There may be two or three paths. Good advice helps you understand those tradeoffs so you can make the decisions that are best for you.

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The Problem Isn’t the Rule. It’s the Context.

I’m a big fan of context. There’s no such thing as a good financial recommendation without understanding someone’s entire financial life. Vanguard attributes about half the value of good financial advice to something no online calculator, rule of thumb, or standardized recommendation can do: helping people avoid making potentially costly emotional decisions during difficult times.

So by all means, read the articles. Use the calculators and rules of thumb. I do. In fact, I create them myself in articles where I’m offering financial tips and best practices. Just don’t confuse useful financial information with personalized financial advice.

One is designed to give millions of people a good place to start. The other is designed to help you make the biggest financial decisions that happen throughout your life.

If you want to take the next step in getting personalized financial advice, check out my recent article on the three ways to work with a financial advisor.

I understand why they feel that way. We spend 30 or 40 years building retirement savings. We contribute to our 401(k)s, fund Roth IRAs, invest month after month, pay down debt and hope we’re doing enough. We become so focused on reaching our “retirement number,” or date, that we don’t spend much time thinking about what has to happen after we get there.

Besides that, the amount we think we might need keeps moving. Northwestern Mutual’s 2026 Planning & Progress Study found Americans now believe they need $1.46 million to retire comfortably—a 15% jump from the previous year’s estimate. That’s a good reminder that there really isn’t one magic number. How you manage your money after you retire is just as important as how much you’ve saved.

To me, retirement isn’t the end of financial planning. It’s the beginning of a completely different kind of financial planning.

I always like to say your money has multiple jobs. While you’re working, your portfolio has one job: grow . . . and keep on growing. Once you retire, it has a much tougher assignment. It has to generate income, keep pace with inflation, weather market downturns and hopefully last the rest of your life. In other words, your portfolio has to replace most of your old paycheck.

That’s why I believe the first five years of retirement are critically important. It’s when you’ll make some of the biggest financial decisions of your life, such as:

• How much can you safely spend?

• When should you claim Social Security?

• How much investment risk should you keep?

• How much flexibility should you build into your plan?

• And how often should you revisit your plan as life changes?

These are decisions you can’t afford to get wrong. We tend to think retirement spending is all about how much we can withdraw every year. But it’s not just about how much you withdraw. It’s about where you withdraw it from, which accounts, and when.

It’s not a small distinction, and it can make a huge difference to your chances of not running out of money.

What This Looks Like for Different People

Let’s say you retire just before the market drops 20%. You still need income, so every month you’re selling stocks that have fallen in value just to pay your bills. Those shares are gone. They won’t participate when the market eventually recovers.

Okay, now imagine someone else who retired with the exact same portfolio but had enough cash and high-quality bonds set aside to cover a few years of living expenses. Instead of selling stocks during the downturn, they leave their stock portfolio alone and give it time to recover.

Both retirees may experience the same market over the next 30 years. They may invest in the same market for 30 years and earn the same average return. Yet one could run out of money years sooner.

Let’s say the two people each retire with $750,000 and both plan to withdraw $40,000 a year. One retires into a strong market. The other retires just before a major downturn and keeps withdrawing the same amount because the bills don’t stop. By selling investments while prices are down, that retiree can permanently reduce the portfolio’s ability to recover. Years later, one retiree may still have a healthy nest egg while the other could be facing the very real possibility of running out of money.

That’s what financial planners call sequence of returns risk, and it’s one of the least understood risks in retirement. Morningstar’s retirement research underscores just how important those early years can be. Under its modeling assumptions, retirees who experienced positive investment returns during their first five years had only about a 4% probability of exhausting their portfolios.

Turning Knowledge Into a Plan

You can’t go back in a time machine and make that decision again. The lesson isn’t that you just have to cross your fingers and hope for a bull market once you retire. None of us controls that.

The lesson is to have a plan for where your retirement paycheck will come from if the market has other ideas. Having cash and high-quality bonds available for near-term income can allow you to leave your stock portfolio alone during a downturn instead of selling investments at exactly the wrong time.

That’s just one example of why the first five years matter so much. The decisions you make about when to claim Social Security, how to draw retirement income, manage taxes and balance investment risk all work together. And they aren’t one-and-done decisions. As your life changes, your plan should change with it.

That’s why I encourage people to sit down with an experienced, fee-only fiduciary advisor in my Wealthramp network before they retire. Not someone who’s trying to sell you a financial product, but someone who can help you build a clear roadmap for the next 20 or 30 years—and adjust it as life unfolds.

The people who seem most comfortable in retirement aren’t always the ones with the biggest portfolios. More often, they’re the ones who know they have a thoughtful plan—and someone they trust to help them make good decisions along the way.

Get those first five years right, and you give yourself something that’s hard to put a price on: confidence. Not confidence that nothing will ever change, but confidence that you’ll know how to respond when it does.

P.S. Every financial situation is different. Here’s how to tell whether you’re getting good advice.

Larry has never been afraid to challenge conventional thinking. Back in 2016, he even mounted a write-in campaign for president to draw attention to America’s long-term money problems.

The backdrop for our conversation was the latest Social Security Trustees Report. It projects if Congress does nothing, by 2032, continuing payroll tax revenue will cover only about 78% of scheduled benefits. That translates into an automatic, across-the-board benefit cut of roughly 22% unless Congress acts.

Larry doesn’t believe Congress will simply let that happen. He expects lawmakers to do what they’ve done before: wait until the pressure is unavoidable and then pass a series of smaller, politically acceptable fixes instead of one comprehensive solution.

In our conversation, Larry was every bit as passionate and opinionated as I expected. My role wasn’t to debate him. It was to ask the questions I hear every day from people who are retired, approaching retirement, or wondering whether Social Security will still be there for their children and grandchildren.

One message came through loud and clear. Larry believes Washington has spent decades postponing difficult decisions, leaving future lawmakers with fewer and more painful choices.

At one point, Larry didn’t mince words. He called Social Security a “government Ponzi scheme.” Not everyone would agree with that characterization, but it captures how strongly he believes the system is fundamentally broken, not merely underfunded.

When I asked who was to blame, Larry got a big laugh from me when he said, “Your grandparents screwed you!” But seriously, his point wasn’t really about grandparents. It was about generations of politicians from both parties choosing short-term political comfort over long-term fiscal responsibility.

Whether or not you agree with Larry’s conclusions, he makes it hard to ignore the broader lesson. The longer Congress waits to deal with Social Security’s funding challenges, the fewer good options remain.

So that’s Washington. What about us, personally?

If Larry is right, don’t expect Congress to suddenly unveil one bold, comprehensive solution. He believes lawmakers will continue reaching for what I’d call political band-aids. They’re smaller, more politically acceptable changes that buy time while avoiding the toughest decisions.

In practical terms, Larry says those band-aids could look something like this:

• Gradually increasing payroll taxes, potentially raising the combined employer and employee rate from today’s 12.4% to about 18.4%.

• Raising or eliminating the cap on wages subject to Social Security taxes so higher earners contribute more.

• Gradually increasing the full retirement age for younger workers while largely protecting today’s retirees.

• Slowing the growth of benefits for higher income retirees while preserving benefits for those who depend on Social Security the most.

• Most likely, adopting some combination of these changes rather than relying on one sweeping reform.

But here’s where Larry takes it a step further. He believes temporary fixes just delay a much bigger reckoning. He said the real solution is to scrap the Social Security system as we know it and build a new one from scratch.

Whether you agree with Larry or not, there’s no mistaking the urgency behind his message. In Larry’s mind, the best time to fix the system was years ago in order to avoid this crisis.

As for me, I mostly agree. At the same time, I have to remind myself we can’t control what Congress ultimately decides. We can control whether we’re financially prepared for whatever it decides. It’s smart to have a plan that doesn’t depend on Washington getting this right.

If there’s one thing I hope people took away from our conversation, it’s this: Worrying isn’t a strategy. Planning is.

P.S. If you’re looking for help with your own planning, check out Wealthramp’s network of vetted, fee-only advisors, many of whom specialize in navigating the complexities of retirement. The process is free and confidential, and we never sell your data.

I was just asked this question by a close friend who had inherited an IRA from a parent. She wanted to know, “Am I going to get hammered in taxes?”

It’s a smart question because it’s one of the biggest misconceptions about taxes.

Most people know inherited IRAs come with tax consequences. And because most non-spouse beneficiaries now have to empty an inherited IRA within 10 years, the question isn’t whether they’ll pay taxes. It’s when, and how much?

It’s so easy to get tripped up. You might assume that taking money out of an inherited IRA will push you into the next higher tax bracket, and then just like that… all of your income will now be taxed at that higher rate.

It doesn’t work like that. Federal income taxes are marginal. That’s the technical term, but the concept is pretty simple. Only those dollars that cross into the next tax bracket are taxed at the higher rate. Everything below that threshold continues to be taxed at the lower rates.

Think of it this way. If you’re standing at the shoreline and dip your big toe in the ocean, your whole body isn’t suddenly submerged. It’s just your toe that’s wet. That’s how tax brackets work.

If this sounds surprising, just know more than half of Americans didn’t understand how marginal tax rates work. According to the 2024 Tax Foundation survey, a third believed all of their income would be taxed at that higher rate. That’s the misconception that leads people to make expensive financial decisions.

Why Your Marginal Tax Rate Matters

It sounds like an in-the-weeds distinction but it’s not. Once you know only the dollars above the threshold are taxed at the higher rate, and the rest of your income doesn’t move up with them, it changes the way you think about tax planning.

I’ve seen people put off taking distributions they actually needed because they were afraid of moving into the next tax bracket. The irony is that waiting too long can leave them taking much larger withdrawals later in that 10-year window, potentially pushing them into a higher bracket than they would have reached by spreading those withdrawals out more thoughtfully.

The same misunderstanding shows up with Roth conversions. People sometimes avoid the conversion because they don’t want to pay taxes today, without realizing that paying a little tax now can sometimes save a great deal more later. The issue isn’t the event that triggers the next tax bracket—whether it’s inheriting an IRA, taking a retirement distribution, or doing a Roth conversion. The issue is understanding what actually happens when you get there.

That’s why I encourage people to stop worrying about “How do I avoid the next tax bracket?” The most useful question is, “How much room do I have left in my current tax bracket?”

Now you can start planning.

That simple shift in your mindset can change decisions you might otherwise make based on fear. Now you’re making decisions based on facts.

This is why I carefully vet independent, fee-only financial advisors for tax planning expertise in addition to their investment expertise. The best advisors don’t just react to a tax bill after the fact. They help clients make better decisions before the tax is ever triggered.

That’s the kind of planning lens Marianela Collado, CPA/PFS, CFP®, an advisor in Wealthramp’s network, is using. She reminds us, “Making money is great, but more important is how much of that money you keep.”

That’s exactly the point. Good tax planning isn’t as much about avoiding tax brackets as it is understanding how they work. Then you can use them to your advantage.

P.S. I spoke to AARP recently about the benefits of a one-time financial plan. Check it out here.

At the outset, I always ask the same question:

“What kind of financial advisor do you want to be?”

Most assume I’m asking what area of financial planning they want to specialize in. I’m not.

I’m asking whether they want to practice as a fiduciary—legally obligated to put their clients’ financial interests first—or under a different business model.

That’s usually the light bulb moment.

Like most consumers, many assume becoming a fiduciary requires another exam, another credential, or some complicated approval process. It seems logical. If you’re going to accept that level of legal responsibility, surely there must be another hurdle to clear.

There isn’t.

Being a fiduciary isn’t a badge or even a credential you earn. It’s a legal standard you choose. Every advisor entering this profession reaches the same fork in the road. They can build a career in the brokerage world, where compensation often comes from selling financial products, or they can choose the fee-only fiduciary model, where they’re legally obligated to act in their clients’ best financial interests 100% of the time.

Then there’s the hybrid, or fee-based, model. These advisors can wear both hats—sometimes acting as fiduciaries and other times acting as brokers selling commissioned products. The legal standard depends on which hat they’re wearing at the time.

To me, that’s like wearing a seatbelt only on certain roads. You’re either buckled in for the entire trip, or you’re not.

Would you knowingly choose an advisor who’s only legally obligated to put your interests first part of the time?

Back to the students.

I ask them one more question:

“Why would someone offering advice choose not to be a fiduciary?”

So far, not one has told me they would. But the students are the exception, not the rule because in the real world, the vast majority of financial advisors have chosen not to practice as fee-only advisors 100% of the time.

They all have the same opportunity. Yet out of roughly 834,000 financial professionals in the United States tracked by the U.S. Bureau of Labor Statistics, only a small minority operate as true fee-only fiduciaries. At the same time, most people who already have a financial advisor mistakenly believe their advisor is legally required to act in their best interests. And according to a recent CFP Board survey, 97% of Americans believe financial professionals should be required to put their clients first.

That’s an astonishing disconnect.

Consumers overwhelmingly believe fiduciary advice is the standard. Most already assume they have it. In reality, very few do.

I’m not telling you what to do with that information. But I do think you deserve to know it before deciding who you’ll trust with your financial future. If you want to see your options, you can browse Wealthramp’s network of fee-only, fiduciary advisors anytime.

I made my choice years ago.

P.S. We’re in the news! I spoke to the Wall Street Journal’s Buy Side about what consumers need to know about wrap fees. Check it out here.

I was there for the Morningstar Investment Conference. The sessions are always excellent, but for me the real value has always been the conversations in between—running into people I’ve only known through LinkedIn, grabbing coffee with colleagues I haven’t seen in twenty years, and being reminded why I love this work. (Hopefully I can meet members of Count Up’s Substack community in person one day, too).

That was true with Christine Benz, Morningstar’s Director of Personal Finance and Retirement Planning and host of The Long View podcast. We’ve moved in similar circles for years, but this was the first time we’d actually sat down together in over twenty years. (Christine frequently writes about the bucket strategy, a helpful framework for retirement planning).

Terry Savage joined us toward the end of our conversation. If you don’t know Terry, she’s a legend in the personal finance world and one of the smartest people I know. Definitely the smartest person in any room she walks into.

It struck all three of us that although we’d taken very different paths, we’d spent decades working toward the same mission: helping people make smarter financial decisions and connect with advice they can truly trust.

The next day I joined Terry on WGN Radio with host John Williams. (You can check it out here!) If you’ve ever listened to Terry and John together, you know they love to spar. John asks the questions listeners are actually thinking. Terry answers directly. I found myself right in the middle of it.

What I appreciated most was that John asked questions like: Who cares how a financial advisor gets paid? Why does fiduciary status matter? And does someone have to let an advisor manage their investments, or can they just get advice and handle their own investing?

We talked about how you don’t need a million-dollar portfolio to get outstanding advice. We talked about what great advice costs, what it looks like in real life. I’ve always felt a need to point out that mediocre advice can end up costing more through missed opportunities, unnecessary taxes, or cookie-cutter financial plans.

Then John opened the phone lines. Here’s where the karma comes in.

A handful of callers came on, and two simply wanted other listeners to know they’d found their advisor through Wealthramp and that it had been a game changer. I won’t pretend that didn’t make me proud.

On the way home, I found myself thinking less about the conference and more about Christine and Terry.

Three women with three different careers and three different platforms. Yet after all these years, we’d somehow ended up in exactly the same place.

We all believe people deserve better financial advice. We believe trust and ethics matter more than ever in the age of AI. And we believe that when people finally find the right advisor, it can genuinely change their lives.

Hearing those callers on WGN reminded me why that mission is worth fighting for.

That question has been on my mind ever since I recorded a podcast about how financial advisors are adopting AI to benefit themselves and hopefully, their clients. I joined Stanford University’s KZSU radio host Dave Levine and invited one of the fee-only fiduciary advisors in my Wealthramp network, Jeff George, CFA. Jeff’s the founder of his own advisory firm, Tao Financial in Orlando.

For a full hour we explored one of the hottest topics in financial services today: artificial intelligence and how financial advisors are already using it.

The timing was perfect. I’d just read about how JP Morgan is introducing AI agents to automate work, boost productivity, and let advisors and bankers serve significantly more clients. The story was all about how AI will help the bottom line. Nowhere did it mention how AI would help clients have better outcomes or improve client experiences.

Most people read that as a story about technology. I read it as a story about ethics.

The Promise and the Trap

For years, we’ve been told technology would democratize financial advice, lower costs, and improve access. In so many ways, it has. Today’s AI tools can analyze portfolios, run retirement projections, spot tax opportunities, summarize meetings, and process information faster than any human.

That part doesn’t worry me.

What concerns me is what comes next. A recent Schwab Advisor Services study (January 2026) found 63% of Registered Investment Advisors are already using AI — more than double the rate from three years ago. Most are using it for administrative tasks, note-taking, drafting communications, research, and meeting prep. Early adopters report meaningful time savings. But most are still just experimenting. Only about 1 in 10 financial advisory firms have policies in place to fully integrate AI into their overall strategy, according to the study.

The question isn’t whether advisors will use more AI. It’s how they use the efficiency it creates. Are they using their freed-up time to build deeper client relationships and deliver more thoughtful advice? Or are they hyper-focused on adding more clients and letting AI handle the volume?

The Human Element AI Cannot Replace

Most people who reach out to me aren’t suffering from a lack of information. If anything, there’s too much information. They’re wrestling with doubt. They’re coming to me every day asking:

• Can I retire?

• How much will I be able to withdraw every year from my savings?

• Will helping my adult child hurt my own future?

• Am I making big mistakes?

These questions are about money. But without context, the answers are worthless. Your family, your health, identity, purpose, and relationships are what drive your desired results. Two people with identical investment portfolios can need completely different advice because they’re solving different life problems.

Good financial advice has always depended on judgment, not just intelligence. AI is excellent at searching what’s already online and helping you ask better, more precise questions. What it cannot do is be the advice.

That distinction was at the heart of our conversation with Jeff George. We talked about how thoughtful advisors already use AI for meeting prep — pulling together portfolio updates, scenario modeling, and relevant research so the advisor walks in better prepared with deeper insights tailored to that client’s situation.

That’s not the same as applying judgment, empathy, and context. What turns good advice into great advice still comes from humans.

Used thoughtfully, AI is a powerful tool for a financial advisor. Used carelessly, it can create a false sense of confidence, encourage cookie-cutter recommendations, or tempt firms to prioritize efficiency, faster scaling, and generating more revenues over the quality of the client relationship.

As an individual, there are several key questions I advise people to now ask their advisor:

• What guardrails have you put in place to ensure AI augments rather than replaces personalized, fiduciary advice?

• How do you test AI outputs for accuracy, biases, or conflicts before they reach clients?

• Will AI help you serve me better — or simply allow you to serve more people with less attention per client?

• How do you define success for your clients, and whose interests come first when difficult tradeoffs arise?

The advisors who stand out won’t necessarily be the ones using the most advanced AI. They’ll be the ones who refuse to let technology erode the human relationship at the core of great advice. They will be more intentional adopters.

As someone who has spent decades building Wealthramp and putting up guardrails to connect people with outstanding vetted, fee-only fiduciary advisors, I believe this AI moment makes independent, conflict-free advice more valuable than ever.

I’ve never seen a more important moment to focus on whether the advisor’s values and ethics align with yours.

What do you think? Has AI changed how you interact with your advisor for better or worse? Drop a comment below. And if you found this useful, please share it with someone navigating their own financial journey.

If you’d like to explore Wealthramp’s network of vetted, fee-only, fiduciary advisors who can help you with everything from a one-time financial plan to long-range support, you can do so here.

The headlines are focused on valuations, growth projections, and whether these companies will ever live up to the enormous expectations investors are placing on them. That’s understandable. When trillion-dollar companies come to market, everyone wants to know whether they’re worth the price.

Millions of people probably think they’re sitting on the sidelines watching SpaceX, OpenAI, and Anthropic go public. But whether you like them or hate them, you’ll likely become an investor without having any say in the matter.

That’s right.

Because who will ultimately be buying all of these shares? The answer, at least in part, is most Americans who are saving for retirement through their index funds.

If you contribute to a 401(k), own an IRA, or invest through broad market index funds, there’s a good chance you’ll soon own pieces of these companies whether you make a conscious decision to buy them or not. That’s because the vast majority of retirement assets today are invested through index funds, target-date funds, and ETFs that automatically adjust their holdings as indexes change.

@wealthrampEveryone's asking "where should I put my money?" with trillion-dollar IPOs like SpaceX and OpenAI on the horizon — but that's the wrong question. The right question is: what job does this investment need to do? Stocks for growth, bonds for income and stability, cash for liquidity, international and private investments for diversification. Every dollar in your portfolio should have a purpose — if you can't explain its job, it might be time to fire it. #personalfinance #investingtips #portfoliostrategy #wealthbuilding #financialplanning

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Nasdaq recently revised its methodology to allow certain mega-cap IPOs to qualify for inclusion in the Nasdaq-100 after just 15 trading days. That means SpaceX could become eligible for inclusion as early as July. Once a company gets added to a major index, funds that track that index must buy shares in order to mirror its holdings.

This is one of the reasons indexing has been such a powerful investment strategy. Index funds don’t try to predict winning horses in the race – they simply invest all the horses in the race. And the approach has helped millions of investors build wealth through low costs, broad diversification, and disciplined investing.

But what so many people don’t realize is that indexing doesn’t ‘buy and hold.’ Your index fund does not stand still. The indexes themselves are constantly changing. New companies get let in. Others leave. In other words, your funds are buying and selling so as markets evolve, your retirement portfolio evolves in lockstep with them. And these are changes you might not know to pay attention to.

Find an Advisor

The next IPO wave is a perfect example.

When companies as large as SpaceX, OpenAI, and Anthropic are admitted into public indexes, retirement dollars become part of the buying force. Stock analysts estimate that SpaceX alone could attract billions of dollars in automated buys from index-tracking funds once it becomes eligible for inclusion.

None of this should be interpreted as a warning against innovation. Some of the greatest investments in history started out as exciting young companies with no profits but massive ambitions. Innovation drives economic growth, and long-term investors should benefit from that growth.

But investors should also remember what an IPO represents. Here’s what I keep thinking about.

For the venture capital firms, hedge funds, founders, insiders, and early employees, an IPO is the payoff. They’ve been waiting and holding shares for years while the company was still private. They’ve watched the valuation climb from millions to billions and, in these cases, from billions to trillions.

The challenge for you as someone saving for retirement in your index funds is that by the time a company reaches a trillion-dollar valuation and becomes large enough for index inclusion, many of those early-to-the-party investors have already enjoyed an extraordinary run up. But will the future returns justify the price that new investors, and your retirement account, are paying?

This is the conversation worth having with your advisor. Not whether SpaceX, OpenAI, or Anthropic are incredibly impressive companies. They clearly are.

That’s the trillion dollar question I suggest you consider right now.

P.S. If you’re ready for a financial checkup, get in touch here anytime. Our advisors are rigorously vetted, and we never sell your personal data.

We’re staring down a pipeline of potential trillion-dollar-scale IPOs like SpaceX and OpenAI. Expectations are high – really high. That has some seasoned investors wondering whether we’re flying too close to the sun.

The S&P 500 is up about 8% year-to-date, which feels really good on paper, but getting there has been a bumpy ride with plenty of volatility. Short-term interest rates are now likely to go up, not down. Then there’s inflation. At the time of this writing, prices on the things we use every day are rising at an annual inflation rate of 3.8%. The highest level we’ve seen in three years.

So yes, we all know the golden rule: ‘stay invested.’ But the real question everyone’s wrestling with is… invest where?

This is where having a network of more than 200 rigorously vetted, experienced fiduciary advisors comes in handy. Matt McKee, CFA, is one of them. He recently wrote on this topic explaining investment approaches in a fresh, understandable way.

As Matt puts it, after you’ve built the financial plan and figured out how much risk you’re really okay with, “now we have to put our money to work.”

Which brings us right back to the question: invest where?

There’s a good reason Matt, just like the other advisors I’ve vetted, doesn’t come out of the gate with stock picks, private investments, or even his latest ideas. Before recommending the investments, he has to know what role that investment is supposed to play in your portfolio.

He starts with purpose. What’s the job you need your investments to do? Because every investment should have a job.

A large U.S. stock fund has a job. An international stock fund has a job. Bonds have a job. And cash has a job.

As Matt points out, “We’re not choosing investments based on the gaudiest historical returns. We’re not chasing investment returns, either. We’re looking for the right tool for the right role inside a portfolio.” Too many investors focus on trailing returns. Matt says that’s a trap. Historical returns do matter, but they won’t tell you the whole story.

The best advisors aren’t trying to predict what happens next. They’re building portfolios designed to survive multiple versions of what happens next.

That’s one reason thoughtful advisors spend so much time evaluating how their clients’ investments interact with one another and pay close attention to taxes and fees.

The goal isn’t to own everything. It’s to own the right mix of assets that can help support the life you’re trying to build through different market environments.

What I appreciate most about Matt’s perspective is that it removes some of the mystery. There’s no secret sauce. No magic fund or perfect forecast. Just a disciplined process for deciding what belongs in a portfolio, why it belongs there, what it costs, and how it supports the life you’re trying to build.

What investing question trips you up most right now? Share it below. We’ll unpack it together.

Reach out to me anytime. And if you’d like to explore Wealthramp’s network of vetted, fee-only, fiduciary advisors who can help you with everything from a one-time financial plan to long-range support, you can do so here.

What I’ve come to realize is that most people have never gotten truly exceptional financial advice, let alone worked with an outstanding advisor. That’s why they often tell me, “I don’t know exactly what I want, but I know I want something better than what I have now.”

Why is finding great advice so messy? Let me assure you, it’s not you. It’s them. And by “them,” I mean the financial services industry.

This is a system largely designed as a sales business model, not an advice model. Still, truly excellent financial advice and exceptional financial advisors do exist. They’re just not in every strip mall down the street.

Many people have worked with the same advisor for years. Others have relied on the rep who works for their 401(k) plan, a broker, an insurance agent calling himself an advisor, a friend, or a family member for financial guidance. And many have just taken on all the financial planning and investment decisions themselves.

When I ask how the relationship with their advisor is going, the answers are quite revealing. The most common answer I get is: “Yeah, she’s okay…I think?” Or “We don’t really hear from him that much.”

Or if I ask what their advisor is actually doing to earn his fee, I get this: “He manages our investments but that’s about it.”

Just this week, someone told me, “The only time we really hear from him anymore is when he wants to sell us something.”

That’s the reality that’s been at the heart of my work for years. I admit it: I have a massively ambitious goal. I want to raise the bar and upgrade the quality of financial advice Americans are getting.

I’m doing this in two ways. First, I encourage people to raise their expectations. Exceptional advice exists. I want people to recognize good financial advice when they see it and understand that they don’t have to settle for an advisor who simply manages investments or checks-in once a year. It’s not about expecting your advisor to outperform the S&P stock index. It’s about your whole financial life. The planning that aligns with your investment strategy.

Second, I believe the industry itself must be held to a higher standard.

One of my biggest frustrations is that so many people operating under the title “financial advisor” are still working within a sales model, yet calling themselves “advisors.” They’re paid to recommend their products and services even if those recommendations aren’t the least expensive or in your best interest, yet consumers are often led to believe they’re receiving objective professional advice.

This is exactly why I keep getting asked: “Pam, how is anyone supposed to find a highly qualified fiduciary advisor – how can this be so messy?”

That’s why I’m pointing out the warning signs people should pay attention to. Not because I enjoy criticizing this industry, but because people deserve to know they have choices.

People deserve to know that financial services is an industry. Not a profession. There is no ‘high bar’ that advisors need to pass.

So who amongst all these advisors do act as professionals even when no one requires it? After more than 30 years covering this profession, providing advice, evaluating advisors, and building a network of more than 230 fee-only fiduciary advisors, my answer is always the same:

Not many.

There are roughly 300,000 to 330,000 people operating under some version of the title “financial advisor” in the US today. In my opinion, the number who are truly exceptional is fewer than 7,000.

That’s still a significant number of professionals, but it’s a very small community relative to the size of the industry.

What separates them?

Professionalism and running a fiduciary practice are the starting points.

These few advisors are the only ones who choose to operate as professionals in an industry that often doesn’t require it. Unlike doctors or lawyers, there is no universal professional standard. In many cases, someone can pass an exam, sell insurance or annuities, and legally call themselves a financial advisor.

The exceptional advisors choose a higher standard. They are students of their craft. They continue learning. They understand investments, but they also understand taxes, retirement income, estate planning, insurance, and the complex decisions families face throughout their lives.

I just had a conversation with a fee-only fiduciary advisor in my network, Jason Lilly, CFA about this. (A video of our chat will be out soon!) He explained that much of his work isn’t really about investments. It’s helping people make better decisions all the time.

That simple statement captures what I’ve observed among the best advisors I’ve met over the years. They listen before they recommend. They ask thoughtful questions. They connect dots. They identify blind spots. Most importantly, they create clarity.

You walk away with a much better understanding of your choices, your opportunities, and the decisions in front of you.

That’s what good financial advice looks like.

The best advisors help people make better decisions about their lives. They help clients avoid big expensive mistakes, think through important tradeoffs, and move forward with greater confidence.

Once you’ve experienced advice at that level, your expectations change forever.

Reach out to me anytime with questions. And if you’d like to explore Wealthramp’s network of vetted, fee-only, fiduciary advisors, you can do so here.

Now it’s about learning how to spend the money confidently after 40 years trying not to.

A million dollars still sounds like it’s enough to support a good lifestyle for the rest of your life, and it may be, but retirement math in 2026 looks very different than it did twenty years ago.

Morningstar’s latest research suggests roughly a 3.9% starting withdrawal rate for retirees seeking a high probability that their savings will last 30 years. That means someone with $1 million invested may realistically generate about $39,000 a year from the portfolio before Social Security.

Add another $35,000 to $45,000 from Social Security for a couple and suddenly the household may realistically be living on roughly $80,000 gross income before taxes.

Comfortable in some places. Tight in others depending on where you live, and how you live.

Now layer in inflation that averages 3% annually. I’m using 3% because it’s much closer to what many economists and retirement planners now view as a realistic long-term planning assumption.

Inflation erodes your money over time so a lifestyle costing $100,000 today could require roughly $135,000 in ten years.

This is where I see retirees often split into two camps.

One group becomes really anxious, almost paranoid about overspending. Every larger expense suddenly comes with huge consequences. They travel and spend but do it with a sense of constant worry.

The other group underspends almost reflexively. They hold back from experiences they could easily afford because they never developed real confidence about what was actually safe to spend. In other words, their retirement plan was never really a ‘spending plan.’

Many people I talk to share that they believed they already had a withdrawal plan because in 2018 they sat down with the guy at Fidelity who printed out a report with pie charts and projections, and confidently told them: “You’re going to be fine. You can retire.”

I’m going to say this very strongly and with a lot of confidence myself: this is one of the few moments in life where you truly need to sit down with a highly qualified, fee-only fiduciary advisor who specializes in retirement income planning. (You can always find one here).

Retirement today is too complex — inflation, taxes, healthcare costs, Social Security timing, withdrawal strategies, market volatility — and the stakes are simply too high to rely on old projections or assumptions, even for financially sophisticated people.

Frankly, I’m doing the same for myself. I know a lot about retirement planning after 30 years, but I’m going to be a lot more confident getting a pair of fresh eyes from an advisor — a peer who I know is highly qualified and won’t be afraid to tell me what I need to hear. In other words: an expert who’s objective.

I’ve also challenged my own thinking over the last few years about retirement itself. Why does retirement have to be one big ‘on’ or ‘off’ switch to work or not work?

I think the healthier model today is a dimmer switch approach. Flexibility and optionality become the real goal rather than unplug completely. Working because I want to means that even earning a small income dramatically reduces both financial and emotional pressure.

If that person with the $1 million portfolio earns even an extra $20,000 to $30,000 a year after taxes through part-time work, consulting, seasonal work, or remote work for a few additional years, it means they may only need to withdraw $10,000 to $15,000 a year from investments for a period of time instead of the full roughly $39,000.

Even just a couple of years of extra income adds up. That reduced pressure during the early retirement years while investments continue compounding can preserve tens of thousands, and sometimes substantially more, over someone’s lifetime.

Even more importantly, people feel less trapped. That’s why I think people should focus less on some mythical “perfect retirement number” and more on building a retirement plan that can evolve as life changes.

If you’d like to explore how a one-time financial plan can meet your needs, get started here.

I’d genuinely love to hear from you about this. What are you hoping retirement will actually feel like for you — security, freedom, purpose, flexibility, family time, something else entirely? Put your thoughts in the comments.