Back Bay Financial Planning & Investments

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Back Bay Financial Planning & Investments Fee-Only, Fiduciary, Retirement & Tax Planning Expertise on the Eastern Shore of Maryland & Delaware

Last night, we hosted our first Annual Client Event at Plantation Lakes Golf Club and Country club in Millsboro. It was ...
10/30/2026

Last night, we hosted our first Annual Client Event at Plantation Lakes Golf Club and Country club in Millsboro. It was an amazing evening, and we were thrilled to have nearly half of the families we work with in attendance. It made for a full house and we wouldn't have it any other way.

The entire Back Bay team is incredibly grateful for the trust and confidence our clients have placed in us. Our goal remains to provide unreasonably good service and advice to the families who have trusted us to work alongside them.

Our mission isn’t done, and we’re hard at work to further improve what we deliver to our clients over the coming year. It was great spending the evening with each and every one of you.

10/26/2026

Going to do our best attempt at a halloween and financial services cross-post. Halloween is a lot more fun with kids running around all sugared up! (Pictures of the Back Bay kids coming later.) Until then....

Financial professionals can sometimes be dressed up as something other than someone who has your interests first all the time.

Our firm is intentionally set up as a fee-only registered investment adviser. What that really means to our clients is that from a regulatory standpoint we’re held as fiduciaries, and we don’t earn commissions on anything we recommend. Not just when we meet, but for the entire duration of our relationship. Initial recommendations, subsequent ones, all have to have your interest in mind first. 100% of the time. That’s the law.

Our industry has another standard, called “Best Interest.” And while the name sounds right, it only applies at the moment a recommendation is made, like when you buy a product. There’s no ongoing duty of care throughout your relationship, regardless of how long you own it. Some advisors can even switch between the two standards depending on what they’re doing for you. Same person, different costume. Unlike kids showing up to your door dressed up, you'd never know.

That may seem like a nuance between standards, but it’s not.

We believe financial planning is very much an ongoing process, not a one-time event. Your life is going to change. Your goals, your circumstances, it’s a bumpy road. Having a professional in your corner who by law has your interests first is, in our opinion, the way it should be. So we try to put our money where our mouth is.

It’s Halloween, but we’re not dressing up as something we’re not. Fiduciaries, all the time.

Have a safe and Happy Halloween - and don't overload on the candy!

10/19/2026

Year-end means harvest season. Not crops, tax harvesting. (Our Eastern Shore clients should appreciate that joke!) Most people are familiar with tax loss harvesting. Gain harvesting gets less attention, but for some of our clients it can be just as valuable.

For our clients with taxable accounts, good tax planning tells us when it makes sense to harvest gains and when to harvest losses.

Losses: Many bonds bought when rates were low are still sitting below what we paid. That window closes on its own. As bonds approach maturity they drift back toward par, and the loss shrinks. While it’s open, those losses can offset gains elsewhere. With equities having run the last few years, that’s especially useful when rebalancing. Harvesting bond losses lets us trim stocks with less of a tax bill. Where applicable, we're doing this.

Gains: This is the more enjoyable one. For clients in the 0% capital gains bracket, we can sell appreciated positions, owe no federal tax on the gain, and buy right back, since there’s no wash-sale rule on gains. That resets the cost basis higher, so the next sale, maybe years from now in a higher bracket, carries a smaller gain. And if the position drops, there’s now a loss to harvest that didn’t exist before. When we manage a sell-down of legacy positions or set a tax budget for a client, we do it with this in mind. This starts with good financial planning.

One caution for those of us in Maryland and Delaware: 0% federal isn’t 0% state. Both states tax capital gains as ordinary income, and realized gains still count toward things like IRMAA and Social Security taxation. We always run the numbers first, Federal and State.

None of this is flashy. It’s the low-hanging fruit of tax management, done every year, so clients keep more of what they earn. After-tax returns are what matter and what we pay attention to.

As always, this isn't specific tax advice and you SHOULD also talk to your tax professional about this.

On top of the beautiful weather and changing colors.....You are probably seeing the election signs. The commercials are ...
10/11/2026

On top of the beautiful weather and changing colors.....You are probably seeing the election signs. The commercials are starting. The promises and fear mongering are getting in full swing. You may have even heard these years are typically some of the worst for the market: Mid-term years. The congressional elections in the U.S. mid-way through an incumbent Presidential term.

Some of the reason mid-term years tend to be worse than others is the randomness of some financial crises just happening then (1974, 1998, 2002, 2010 to name a few).

Since 1950, the S&P 500’s average peak-to-trough drop in a mid-term year has been about 16–17%.

The reality is there is some seasonality to traders positioning for potential policy changes with a potential change in control of our legislative branches.

The good part of that seasonality is after the election is over, there isn’t any more election surprise... at least for another two years. So in a mid-term year, returns tend to be pretty strong in the 4th quarter. Why? We think because more certainty comes into the market.

So, while we understand that election time brings about questions on your money, your positioning, and if there is anything you should change - historically it’s been a pretty good time to stay invested. Despite the discomfort that comes from peak political season.

Of course this isn’t specific investment advice and our client portfolios are always uniquely invested to their specific goals. :) Past performance is never indicative of future results.

10/05/2026

October is a great time to talk about Qualified Charitable Distributions (QCDs). Someday we hope legislation will be passed making this tool available to all ages! But until then, for clients and those who are over 70.5 it remains the top tactic for charitable giving.

A QCD definitively makes a charitable gift a tax savings tool. The money goes from your IRA straight to the charity and never shows up in your income. Compare that to a regular cash gift, which relies on you itemizing your return (unless it's the new $1,000 single / $2,000 joint deduction for people taking the standard deduction) and is now subject to a 0.5% of AGI floor starting in 2026. So, it's the definitive way to make your dollars go farther. You can give up to $111,000 per person this way in 2026, and the limit is indexed each year for inflation - so 2027 will be higher.

Behind that it also satisfies all or a portion of your required minimum distribution once you've reached RMD age. That is a big deal if you have significant RMDs that may be pushing you over an IRMAA threshold or phasing out your enhanced senior deduction. Using a QCD can keep your AGI below some of these thresholds. That's the exact kind of thing we're working on with our clients right now.

Maybe most importantly - we recommend doing them around October. Why? Charities are busy. They are also usually understaffed or have significant volunteer staffs. So, we see that checks may sit around and go uncashed for over 60 days. What does that mean? At least at Schwab, a check that sits uncashed for 60 days gets voided and credited back to your IRA. If you did it in November or December, that can mean the gift lands in a different tax year, or doesn't count at all, and you find out when the 1099-R shows up. Bottom line - it creates problems. Part of what we do is make sure checks get cashed and give some room if one isn't - we can reissue the check while it's still the same tax year.

Managing the logistics is not only good planning but it makes your tax time a good bit simpler. If you're planning on a QCD this year, consider giving a little bit earlier than planned.

It's time for another post on..... bonds. Interest rates are the talk of financial TV and for good reason. We haven't se...
09/28/2026

It's time for another post on..... bonds. Interest rates are the talk of financial TV and for good reason. We haven't seen rates this high in nearly 20 years. For borrowers, it isn't good news. Coming off a decade of ultra-low rates, it's a bit of a culture shock. Many of our clients will tell you their first mortgage was in the teens. We're not there yet, but rates are moving that direction.

For investors, this is the land of opportunity. Bonds are the ballast in most portfolios, but they also generate returns and cash flow. What they return is a byproduct of the rate environment. A quick reminder: a bond fund's starting yield has historically been one of the best predictors of what it returns over the following years (see our chart). If rates go up, the price drops, but the fund reinvests at the higher rates. Over a period roughly equal to the fund's duration, those two tend to cancel out. Today, many high-quality bond funds have a yield to maturity of 6-7%. We pay close attention to our bond funds yields and how the managers position as rates change. They are doing what you'd expect. Locking in higher rates.

A lower-volatility return stream in the mid-to-high single digits is a huge win for retirees living off their portfolios. It's borderline equity-like returns without the volatility. It's also a buffer against rates rising further. One reason 2022 was so bad for bonds is that rates were still near the floor. There was almost no income to cushion the price drop. We've had several years of higher rates since then, and that extra income has softened the volatility this year. So bond prices might be down, but they are now just up a few percentage points or down ever so slightly. That can happen every so often. That's what is setting up the next few years of fixed income returns, which are starting to give equities a run for their money. It's only September, but this is something to look forward to in 2027 and the next few years.

Does life feel like it's speeding up? Or are you just seeing more in the rearview mirror? When I first saw this chart, i...
09/22/2026

Does life feel like it's speeding up? Or are you just seeing more in the rearview mirror? When I first saw this chart, it stopped me. Framing things we already know differently has that impact sometimes.

Our perspective of life changes with how much we've experienced. This has implications for financial planning. Specifically, how we prioritize goals as our perceptions change and our life experience grows.

One of the objectives of financial planning is helping people avoid the hidden cost of waiting or deferring major decisions. Put off that trip, that boat, that thing you've been "getting around to" for five years, and you haven't just lost five years. You've spent a bigger chunk of what's left than you would have if you'd done it now.
The math only gets worse the longer you wait. Call it the someday tax. It's the one bill that goes up the longer you avoid paying it. Kind of like compounding in reverse.

I see this play out with clients and my personal life all the time. It's a natural human behavior. The plan is never the problem. The permission to actually use the money on the stuff that matters before "later" quietly becomes "never" is what we're after.

Putting tactics into play that help you move those things forward is how we define financial planning success.

09/15/2026

Can it make sense to convert to a Roth one year, and contribute to a Traditional IRA the next? Isn't that counterintuitive?

If you got that advice from a financial advisor, you might feel that way. Though from a tactical standpoint it can be the exact right thing. Tax planning isn't a straight line.

You are paying the tax on assets when it makes sense to you. That might mean moving money to Roth (paying the tax) in year 1 of retirement, but picking up some part-time work in year 2 and deferring income to max out your enhanced senior deduction or avoid IRMAA. Kick the can down the road. People's retirement plans change all the time. Many people pick up part-time work or have some income suddenly. This can change the marginal rate a conversion gets taxed at. And the reality is, that can make a conversion no longer make sense.

I think one mistake people make in planning is wanting a straight line for the next 5 years. We're human, and it's natural to think in patterns or want a baseline for what the next few years look like. Though the more I work with clients, the less I think that's the optimal solution. These decisions are annual, and to treat it as anything differently probably leaves money on the table.

09/10/2026

I recently read Vanguard's latest research paper on "Transferring Wealth with Wisdom." The premise, if you haven't read it, is on the timing of receiving an inheritance and optimizing for its impact.

One of the main findings is there is usually a mismatch between when an inheritance actually lands and when someone's biggest capital need actually hits. An inheritance at anytime is never bad, but wouldn't you rather the timing actually fill a need, instead of just landing whenever it lands? I think most people genuinely want their money to make an impact. In their own lives, and in the lives of others where applicable. Reconciling the timing of the need with a gift is an easy way to make that happen.

A number that stuck out from the study is only 3% of inheritances transfer while the person giving them is still alive. Forget the tax benefits for a second, making a gift count starts with a conversation and matching it to the moment it'll matter most. That rarely happens.

I find my clients thinking more about this, and I'm having more conversations about it as well. I think it is a huge untapped financial planning opportunity for people to really make an impact with their money in their own family just by changing the conversation.

I think it is one of the better whitepapers I've seen this year for practitioners as well as clients. You can read it here:

Address

39682 Sunrise Court #303
Bethany Beach, DE
19930

Opening Hours

Monday 9am - 4pm
Tuesday 9am - 4pm
Wednesday 9am - 4pm
Thursday 9am - 4pm
Friday 9am - 4pm

Telephone

(302)3161820

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