Robert Bennett, CFP

Robert Bennett, CFP I am a CFP® professional who helps families and professionals make smarter decisions with their wealth.

With a focus on clarity, discipline, and long-term strategy, I guide clients through retirement planning, investment management, and wealth transfer.

01/05/2026

Why is January an important month for your RMD strategy?

Most retirees treat Required Minimum Distributions (RMDs) like a year-end chore. They wait until December, scramble to calculate the amount, and then take a lump sum.

If you’re 73 or older, waiting until December could be the least tax-efficient way to handle your retirement accounts.

Here is why you should look at your RMDs this week:

1. Avoid the "Market Timing" Trap - If you wait until December to take your RMD, you are forced to sell regardless of where the market is. By planning now, you can set up automated monthly or quarterly distributions. This "dollar-cost averaging" approach protects you from being forced to sell at a market low just to meet a deadline.

2. The QCD Advantage (Qualified Charitable Distributions) - If you are charitably inclined, the "First Dollars Out" rule is critical. The IRS considers the first money leaving your IRA as your RMD. If you want to use a QCD to send money directly to a charity tax-free, it’s much cleaner to do it at the start of the year before you accidentally trigger a taxable distribution. This helps to manage your AGI.

3. Clarity on Your 2026 Tax Bracket - Calculating your RMD now gives you a clear picture of your "floor" income for the year. Once you know your RMD, you can make better decisions about: Roth conversions, tax-loss harvesting, and withholding adjustments to avoid underpayment penalties

4. The "Secure 2.0" Buffer - The rules have changed significantly over the last few years (like the shift to age 73 for RMDs). Checking in now ensures you aren't following outdated advice or missing a deadline that carries a 25% penalty.

Don't let the IRS dictate your December. Use this week to calculate your 2026 requirement (based on your Dec 31, 2025 balances) and decide if a monthly or early-year distribution fits your cash flow better.

Do you prefer taking your RMD in one lump sum or spreading it out over the year? Discuss in the comments.

Send a message to learn more

12/08/2025

I see smart people telling me they want to do a Roth Conversion.

They make too much money to contribute directly to a Roth IRA, so they try the "Backdoor Roth" strategy.

They plan to put money from their bank account into their Traditional IRA and immediately convert it to their Roth, thinking it will be tax-free.

First you need to ask yourself... Do you have any IRAs that have pre-tax dollars? ANY. IRA. SIMPLE? SEP? Traditional? Rollover from an old job?

If so, you might want to rethink the backdoor Roth idea.

Think of all your IRA money as a cup of black coffee.

This represents all the pre-tax money you have saved or rolled into an IRA over the years.

Now, you pour in some cream. This represents the $7,000 after-tax contribution you want to make to convert into a Roth.

Once you pour the cream in the coffee, try taking just the cream out.

You can't.

It's mixed. If you try to spoon it out, you will get mostly coffee (taxable assets) and only a small amount of cream (after-tax assets).

Let's say the mixture is 93% coffee and 7% cream. Even though you put in after-tax dollars (money you already paid tax on), 93% of that conversion is taxable in the year you make it.

Even worse? Most of the cream (your tax-free basis) is left stuck in the cup of coffee.

The Solution? Pour the cream into an empty cup.

Before you contribute, move your old IRA money into your current 401(k). Once the IRA bucket is empty (no pre-tax in any IRA), you can add your cream and convert it tax-free.

12/04/2025

Estate planning often gets overlooked because many believe it's only for people with millions of dollars. The truth is, it's for anyone who wants clarity, control, and less chaos for their family.

If you own a home, have children, a bank account, or even a car, an estate plan keeps decisions out of strangers hands and puts them in yours.

A will prevents guesswork.

A healthcare directive protects your wishes.

Beneficiary designations move assets smoothly.

A simple trust can avoid probate headaches.

Power of Attorney gives someone you trust the ability to act for you if you cannot.

You do not need millions for those tools to matter.

If you want to make sure what you built (no matter the value) ends up where you want it, start the conversation now. Estate planning is not about how much you have. It is about protecting what matters to you.

12/03/2025

Retirement sounds simple on paper. You stop working, use the money you've saved, and enjoy life. The reality gets messy fast if you are not careful.

That's where I step in.

Turning a portfolio into reliable income that lasts. Pensions are not what they used to be and Social Security rarely covers the whole picture.

Tax efficiency that keeps more money in your pocket each year. Withdrawals and RMDs are not something to guess on.

Investment management built for stability, not adrenaline. A downturn hurts more when you are no longer earning a paycheck.

Estate and legacy planning so assets transfer cleanly to the next generation without confusion or chaos.

Simplifying accounts, statements, and decisions. No retiree needs financial clutter.

Retirement should feel secure, organized, and calm. If you are retired or getting close, a conversation could save you from costly mistakes later.

Send a message if you want your money working with a plan, not guesswork.

12/02/2025

The end of the year is when small financial tasks either get handled or forgotten. Handle them now.

Review your portfolio for losses you can harvest. If something is down and no longer fits your plan, take the loss and use it to offset gains.

Check your retirement contributions. Make sure your 401k/403B/457, IRA, and HSA are funded the way you intended. If you expect to owe taxes, increasing contributions can help.

Consolidate old accounts. Stray investment accounts and outdated insurance policies add risk and confusion. Clean them up before the year ends.

Verify your tax withholding and estimated payments. If your income changed this year, make adjustments now to avoid a surprise come tax season.

Finalize charitable giving. If giving is part of your plan, do it with a strategy. A donor advised fund or direct gifts can reduce taxes if done before year end.

Simple steps, real value. Most people skip them. If you want help tightening things up before the calendar flips, I am here to help.

Send a message to learn more

11/25/2025

Too many people think someone is managing the assets in their 401k.

They’re usually wrong.

Your company selects the plan. Your employer picks the lineup. But the day you enroll, nobody is sitting behind the scenes adjusting your risk, rebalancing you, or making sure your portfolio fits your actual life.

You pick a few funds... forget about it then ten years go by. Retirement gets close and the cracks show.

I see it all the time with people who have five hundred thousand dollars or more in their plan. They’ve done the hard part by saving, but they’re flying blind on the strategy.

Common issues
• Portfolios that haven’t been rebalanced in years
• Target date funds that don’t match their goals or risk
• Concentration they never noticed inside their fund choices
• Old 401ks sitting untouched for a decade
• Believing HR is “watching it” when that isn’t how it works

The 401k is often someone’s biggest asset. It deserves more attention than a once-a-year login and a hope that everything is on track.

If you’re not sure what your allocation actually looks like, how much risk you’re taking, or whether you’re set up for retirement, it’s worth reviewing before the market decides for you.

If you want a clear, no-nonsense breakdown of how yours is positioned, send me a message. I’ll walk through your plan options and show you what’s working and what’s not, so you can make smarter decisions with real numbers behind them.

Your money is already working hard. Make sure the strategy is doing the same.

Send a message to learn more

11/24/2025

Thanksgiving always brings out the same question.

“How are things going?”

Most people answer with “Good” which is basically the adult version of “6 7.” Nobody knows what it actually means.

Not clear. Not confident. I see the same thing with people and their finances.

They work hard, they save, they invest… but if you pressed them on taxes, retirement income, risk, or how everything fits together, the answer gets fuzzy fast.

This time of year is when people slow down long enough to realize they want more clarity.

If you’re heading into the holidays with that “6 7” feeling about your financial picture, fix it. You don’t have to overhaul your entire life. You just need a real plan that matches where you’re trying to go.

11/14/2025

Why do I always look over my plan for the next day before I go to bed?

The answer is simple. I would rather start the morning prepared than spend the day reacting.

Too many people react to their finances rather than prepare.

They work hard, save what they can, build a solid income, yet still feel like their money is scattered and running in different directions.

Life moves too fast to rely on guesswork and your finances are no different.

When I sit down with clients, the goal is straightforward. Create structure and bring every account into one view. Line up what they want long term with what they actually own. Remove anything that drains time, cash flow, or attention.

Once everything is organized, the pressure drops fast.

You know what to save, where it should go, and what truly matters.

A little clarity today prevents a lot of stress tomorrow.

If your financial picture feels disjointed, it can be fixed faster than you think.

10/30/2025

Most investors think they’re diversified. They might not be.

Owning 10 funds sounds safe until you look under the hood and realize 8 of them own the same top 10 stocks.

Apple, Microsoft, Amazon… again and again and again.

That’s not diversification; it’s duplication.

True diversification isn’t about how many funds you own. It’s about how those funds behave when the market changes.

If everything in your portfolio moves in the same direction at the same time, you’re not diversified; you’re concentrated in disguise.

A proper plan should balance growth, income, and risk across different asset classes, styles, and correlations, not just fund names.

I see it all the time where portfolios that look diversified on paper but crumble when volatility hits.

If you’re not sure how exposed your portfolio really is, it’s worth a second look.

10/27/2025

Complexity in your portfolio often hides in plain sight.

Multiple accounts, multiple managers, multiple layers of fees.

What feels “diversified” can actually be disorganized.

Simplifying doesn’t mean giving up sophistication, it means bringing everything under a coordinated plan built around you.

The wealthiest families I work with all have one thing in common: clarity over every dollar.

10/24/2025

Most people spend more time planning their vacations than planning their retirement.

Retirement is supposed to be freedom; freedom from work, freedom to choose how you spend your time, and freedom from financial stress.

Yet for many, it turns into uncertainty about income, taxes, and market risk.

A well-built retirement plan is more than a pile of investments. It’s a coordinated strategy for income, growth, and protection.

That means knowing where your retirement income will come from (and how much of it is reliable).

It also means managing investments to generate growth without taking on unnecessary risk while controlling taxes so you keep more of what you earn.

If you’re nearing retirement or already in it, the right plan can make the difference between hoping your money lasts and knowing it will.

Let’s make sure you have a plan that gives you confidence for the decades ahead.

10/20/2025

If you’ve ever switched jobs, chances are you left behind a 401(k). It happens more often than you think.

The problem is, many of those accounts end up forgotten or mismanaged.

I’ve seen people with multiple 401(k)s scattered across old employers, each invested differently, with no real strategy tying it all together.

When you leave a job, you generally have four main choices with your 401(k):

Leave it where it is. It could make sense, but not always.

Roll it into your new employer’s plan.

Roll it into an IRA. More flexibility and control.

Cash it out. Usually the worst option.

The right move depends on your broader financial plan, taxes, and investment strategy. It’s not a one-size-fits-all answer.

If you’re changing jobs or still have an old 401(k) sitting with a past employer, now is the time to make sure it’s working as hard as you are.

This is something I help clients navigate every day.

If you want clarity on the best option for your situation, let’s have a conversation.

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Stratford, CT

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