Back Bay Financial Planning & Investments

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

Last week I had the privilege of speaking at the Community Foundation of the Eastern Shore, joining Coastal Hospice for ...
06/03/2026

Last week I had the privilege of speaking at the Community Foundation of the Eastern Shore, joining Coastal Hospice for an event on charitable giving and tax planning.

The passage of the OBBBA has meaningfully changed the landscape in 2026 and the changes cut in two different directions depending on how much you give.

For standard deduction filers, there's genuinely good news. For the first time since the pandemic-era provisions expired, non-itemizers can deduct up to $1,000 (single) or $2,000 (married filing jointly) in cash gifts directly on their return, no Schedule A required. For a lot of households, that's a real, tangible tax benefit from giving that simply didn't exist last year. Keep track of all those cash gifts!

For larger givers, the picture is more nuanced. Itemizers now face a 0.5% of AGI floor before any charitable deduction kicks in, plus a 35% cap on the tax benefit for high-income donors. That doesn't mean giving is less worthwhile, it means it has to be more thoughtful. Strategies like qualified charitable distributions, donor-advised funds, bunching, appreciated securities, and for those with significant assets - charitable remainder and lead trusts become more important when the straightforward deduction is squeezed.

The CFES and Coastal Hospice put on a wonderful event, it was a great opportunity to dig into all of it. The work these organizations fund in this community is hard to put a number on, and that's kind of the point.

I've gotten a couple of questions about bonds lately. Yields have moved up, and when yields rise, the bonds you already ...
05/28/2026

I've gotten a couple of questions about bonds lately. Yields have moved up, and when yields rise, the bonds you already own fall in price so a lot of folks see red on their statements and wonder what's happening. Not the same volatility you see in stocks, but some volatility nonetheless. The last couple of years of bond returns have been pretty darn good.

Here's the part that gets lost. Without writing a dissertation on it, I think of mid- and long-term rates as a rough proxy for expected inflation plus expected economic growth. Both have been pushed higher by structural forces, the enormous AI capex buildout and a federal government issuing a lot of debt, not by a one-off shock. Oil, as a result of our recent conflict, has nudged inflation slightly higher as well.

The silver lining is the chart below: a bond's starting yield has historically been one of the best guides to the return it delivers over the next decade. Higher yields today have historically been associated with higher returns going forward. It's the same idea across asset classes, when prices fall, future return expectations rise.

For retirees, that's genuinely good news. A bond sleeve that's actually paying you again does more of the heavy lifting, which means you lean on your stocks a little less for the income and stability your plan needs.

Past performance is of course not indicative of future results, and the chart is illustrative, not a specific forecast.

Spent a few days in Leland, Michigan last week with a small group of RIA owners — no agenda other than working on our bu...
05/12/2026

Spent a few days in Leland, Michigan last week with a small group of RIA owners — no agenda other than working on our businesses together. It's a study group I've joined, and this was our annual time to get together in person.

I've always believed diverse perspectives sharpen me as both a practitioner and a business owner. I came away with great feedback on what we're building at Back Bay, and I like to think I gave some useful feedback in return.

One thing I've adjusted to as a new RIA owner: being a steward and fiduciary to clients isn't just about the planning and investing. It's about making sure the firm itself is built to serve them well for the long haul, a different kind of work you have to periodically step away for. Doing it on the heels of wrapping up our annual Spring reviews made for perfect timing.

And no, being out of state doesn't mean I started sleeping in. Early morning runs along Lake Leelanau were amazing. Cold air, cold water. Every morning, we jumped in to start the day. Wakes you right up.

Yesterday I got to spend the morning judging the second annual Salisbury University financial planning competition.Most ...
05/02/2026

Yesterday I got to spend the morning judging the second annual Salisbury University financial planning competition.

Most of you know I teach as an adjunct for the Perdue School’s financial planning program and serve on its advisory board. So getting to watch these students present is personal for me. The preparation, the presentation, the depth of knowledge - it keeps getting better every year. The full academic and professional community support has been awesome.

The future of financial planning locally and across the country being developed here on the Eastern Shore is in good hands. I’m just glad to play a small part in it.

Congratulations to all the winners - well deserved!

The market can feel confusing right now. Prices are up, headlines are noisy, and it's hard to know what to make of any o...
04/27/2026

The market can feel confusing right now. Prices are up, headlines are noisy, and it's hard to know what to make of any of it.

The reality is over time, stock prices follow earnings. Not the news cycle, not the sentiment on social media, not whatever the talking heads said this morning. If businesses make more money, they're worth more. It really is that simple, even when the short-term noise makes it feel anything but.

This chart shows that relationship going back to 2000. Notice how the two lines tend to find each other, even after dramatic separations. Right now, 12-month forward earnings growth sits at +31.3%, one of the stronger readings in the past two decades.

Markets are forward-looking. They're already trying to price in what comes next. The question isn't what the headlines say today. It's what earnings look like six to twelve months from now.

Earnings season is underway, and so far the results are holding up. Markets are reflecting that, even with everything else going on.

As if you needed another reason to anchor your portfolio in passive core holdings…New research from Morgan Stanley looke...
04/21/2026

As if you needed another reason to anchor your portfolio in passive core holdings…

New research from Morgan Stanley looked back at 44 years of U.S. public companies. Out of every 100, only 18 survived as independent, publicly traded firms. 43 were absorbed through mergers. 39 were delisted — 37 of those for cause. 8 of every 10 aren't even investable tickers today!

Bessembinder's research points in the same direction, and the odds are even worse. The simple truth is most individual equity bets don't pay off. The math isn't close. A handful of mega-winners carry the entire market's return, and the odds of picking them in advance are not in your favor. It's why we expect premium returns for investing in equities. Most fail.

The first step in retirement investing isn't finding the next great stock. It's avoiding the mistakes that don't need to be made.

Passive core holdings aren't settling for less, it's maximizing your odd's of winning.

A lot of people are worried that rising oil prices signal a recession. Historically, that concern is well-founded as mos...
04/14/2026

A lot of people are worried that rising oil prices signal a recession. Historically, that concern is well-founded as most major oil shocks have coincided with economic downturns, and the relationship isn't just correlation, there's causation. So, will this spike in oil prices be different?

I think there are good reasons the market has held up surprisingly well despite elevated geopolitical uncertainty and an oil supply shock. It's why I like this chart: energy simply represents a smaller share of consumer spending today than it did a decade ago, currently sitting around 3.6% of total personal consumption, compared to nearly 10% at the peak in the early 1980s.

That decline isn't an accident. The U.S. economy has become structurally less energy-intensive over time, more fuel-efficient vehicles, better home energy efficiency, and a shift toward a services-driven economy that just doesn't run on oil the way manufacturing did. Layer on top of that the U.S. shale revolution, which transformed America into one of the world's largest oil producers, and you have a fundamentally different market than the one that drove the recessions of 1973 and 1979.

I'll be the first to admit that noone loves paying $4 at the pump. But the transmission mechanism, the drag on consumer spending that historically turned oil shocks into recessions is weaker today than it was in the past.

In investing, it's important to remember this is what progress looks like. It isn't always linear or pretty, but over time humans adapt, innovate, and build resilience into systems that were once more fragile. The oil market of 2025 reflects fifty years of hard lessons. It's worth remembering how dynamic human innovation is and how that affects markets over time.

04/08/2026

It's almost the end of tax season — and many retirees over 65 are learning they may have been pushed over an IRMAA threshold.

IRMAA (Income-Related Monthly Adjustment Amount) means higher Medicare Part B and Part D premiums, but with a two-year lag: income from 2024 affects your 2026 premiums. You'll get reminded of this one again in the future. 😊

If you actually received the income that triggered it, the higher premium is usually manageable — IRMAA surcharges are generally less than 3% of the income that caused them.

What I see practitioners and individuals miss is on phantom income — Roth conversions, capital gain distributions, or asset sales that push you over a threshold without a corresponding cash benefit. These are the "self-inflicted" mistakes, and that's where proactive tax planning matters most.

IRMAA technically isn't a tax — it's a reduction of a Medicare subsidy. But it's a real cost in retirement, and understanding it is essential to making smart decisions about conversions, gain harvesting, and income timing.

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