Year End Edition! In mid-November! Hi Friendos, I looked at my calendar for the next several weeks and realized that between gearing up for next year’s tax season and some upcoming travel, this newsletter needs to start its year-end break a little on the early side. So today I bring you thoughts for year-end financial planning, holding the line on holiday gift spending, and how you can simultaneously get your 2025 taxes done, support a beautiful neighborhood food coop, and work with me!

Not Your Deductible, Not Your Co-Insurance. Just Your Co-Pay. Hi Friendos, Recently I had a minor ultrasound-guided procedure at a Manhattan location of Lenox Hill Radiology. I knew the procedure was fully covered by my insurance, because I checked on this in advance, but Lenox Hill’s admin errors led them to disagree. I arrived 15 minutes before my appointment time to check-in.

It is not the LLC structure itself that can offer tax savings, it is electing tax treatment as an S-Corp Hi Friendos, Last week I wrote about my top advice for people starting out with self-employment income. I claimed that most do not need to worry about forming an LLC, which takes some administrative doing and costs money to establish and maintain.

My Top Advice for People New to Self-Employment Income: Learn About Quarterly Estimated Taxes, Don’t Sweat the LLC Hi Friendos, People who are first starting with self-employment income run into all kinds of advice, good and bad. Typical advice includes “Choose the Right Business Structure.” People focus their energy on researching how to establish an LLC, something they can typically skip, and have nothing left in tank to learn about paying quarterly estimated taxes, which is a must.

Hi Friendos, Today I have cooperatives on my mind. I’ll bet you participate in the cooperative economy even if you don’t know it! Have you ever had medical treatment in a hospital? Visited someone in a long-term care facility? About one-third of medical laundry in the U.S. is cleaned by laundry cooperatives that are collectively owned by the hospitals they serve.

Planning my services for the 2025 tax season Hi Friendos, I cannot predict when the federal government shutdown will end, but I can say that you still are required to file your tax return on time! If you got an automatic extension on your 2024 tax return, the October 15th deadline is almost here. I am doing a little planning for the 2025 tax season.

Today is the Perfect Day to Give Money to a Food Bank Hi Friendos, Today I’d like to share a selection of recent news from around the country: Atlanta, Georgia: “Atlanta Food Bank braces for surge as shutdown threatens SNAP, federal supply.” “[D]uring the last major shutdown in 2019, they saw how quickly the need increased. But now, he said, they’re starting from a much higher baseline level of need.”

Saving, Spending and Counting up the Month Hi Friendos, A couple weeks ago I was talking to a neighbor about budgeting and FIRE. She was trying to figure out how much money their household actually spends each month but getting a bit stuck in the mud with accounting for certain medical spending. They put money into an FSA offered at her job, which covers some of their medical expenses, they have some out of pocket expenses that are partially reimbursed by their insurance company, and some things they pay for outright.

Social Security credits are more interesting and a lot more complicated than you might think Hi Friendos, Today’s topic is Social Security credits – how you earn them and what you get when you do. Earning one Social Security “credit” Earning a credit is like a pass/fail class, you either make it or you don’t. In 2025, “you receive 1 credit for each $1,810 of earnings, up to the maximum of 4 credits per year.” For millions of workers with W-2 private sector jobs, this statement is precisely correct.

In which I provide a tax reminder, a call for maintenance, and admit my time got derailed this week. Hi Friendos, A reminder! Tomorrow, September 15th, is the deadline for quarterly estimated tax payments. This week I am not sending a regular newsletter because I had a few things come up recently that took a lot more time than expected, crowding out my time for writing.

You Should Understand Your Largest Asset: Social Security Hi Friendos, The very first article I wrote for this website was called “You Should Understand Your Largest Expense.” I asserted that most people think their largest expense is housing, but in fact it is usually taxes. Well, it turns out that most Americans think their largest asset is their home or investment portfolio, but in fact it is usually…

It is a hassle to price shop a dentist but it’s worth it if you’ll stick around a while Hi Friendos, I’ve written quite a bit about my recent deep dive into dental insurance and today am going to wrap it up with a discussion of the cost of basic teeth cleanings. I know, not everyone has coverage for those…

Don’t feed the trolls. Tell Congress: no tax prep bridge trolls! Hi Friendos, Last week my business received a letter (my official LLC name is Levinson Lee Consulting and my registered “doing business as” name is Frequently Taxed Questions). I opened the letter and thought, “oh yeah, that thing I have to file every other year with New York State.”

Charity care and other strategies to reduce medical bills, and organizing paperwork for bills you do have to pay Hi Friendos, Last week I promised to discuss practical considerations for using FSAs and HSAs, and tracking medical expenses in general. Before I get to that, I want to talk about steps you can take to see if you even owe that money at all.

For tax purposes, a “Qualified Medical Expense” is mostly what you think, plus a bit more Being an adult in the U.S. means sometimes dealing with things that are both dull and important, like taxes and medical insurance. Today I focus on the intersection of these: what constitutes a “qualified medical expense” for tax purposes. You’ll want to understand what medical expenses count as “qualified” to take full advantage of possible itemized deductions or tax-favored health plans…

Pet Medicine is Also Cheaper Abroad? Hi Friendos, I’m taking a little time off this week, so today’s newsletter is short and sweet. You are surely familiar with the way pharmaceutical companies charge U.S. consumers more than for the exact same drug as what they charge people in other countries. They are milking us to increase their profits. Well...this might be true for pet medicine also.

I learned that a provider who “takes my insurance” may not be “in-network” Hi Friendos, Today I am sharing how I’ve ended up, over the last couple decades, paying a lot more for dental care than I needed to. I’ve always tried to be a careful steward of my money but my ignorance of how my insurance worked really cost me.

When you ask Cigna if your dentist is in-network and discover they hired George Orwell as a consultant Hi Friendos, As you know from prior newsletters, I’ve been learning a lot about health insurance this summer. Today I am writing about something that I’ve learned is not at all a new topic, but was new-to-me: in-network status for a medical provider or medical practice is not always a simple yes or no…

Come correct on money stuff when you get married Hi Friendos, This week, I wanted to think about a nice thing that is nice: when people are in love and want to get married. It’s so nice! I was thinking about this because of a recent “Tax Tip” newsletter I got from the IRS called “Tax checklist for newlyweds…

Your Dental Insurance Has an Annual Max: Get the Most Out of It Hi Friendos, This week I am here with two ideas to help you get the most out of dental insurance. Both involve understanding your annual coverage limit, assuming your policy has one. In the last 10+ years, I’ve had dental insurance from Delta Dental and Cigna, two of the largest players in the space.

Hi Friendos, I am happy to report that since I wrote last week’s very personal newsletter, it looks like we have some rays of sunshine breaking through the clouds. More upcoming tests and doctor visits will provide additional information. In the meantime, I have been giving myself a crash course on insurance and been learning a LOT. Is there any subject more boring, byzantine, and blood boiling than U.S.

Dear Friends, Today’s newsletter is personal and a bit of a rant. I promise, this is also a little bit about taxes. And social murder. And war. Please indulge me this week, I’m in a vulnerable place. ~~~ If you’ve been here for a while, you know that my husband has medullary thyroid cancer. Last year I wrote about our lab work adventures with Blue Cross Blue Shield of Massachusetts, our former insurer, where they routinely denied covered services and I continually had to submit appeals.

Hi Friendos, Today I am going to share a little tax “trick” that could help some people avoid an underpayment penalty if they did not make quarterly estimated payments on schedule. Maybe it will help you out. The scenario: You received some income where taxes were not withheld, like self-employment income or interest income. You didn’t pay quarterly estimated taxes…

Hi Friendos, Today’s topic is the backdoor Roth IRA. Before diving in, I have a couple of reminders: If you pay quarterly estimated taxes, remember that the June 16th deadline is coming up for Q2 2025. I wrote about estimated taxes in this article last year and this IRS FAQ page on estimated taxes is also very helpful. Next Saturday, June 14th, I am hosting my first monthly “Tax Me Anything,” a free session via Zoom on the second Saturday of every month, 11am-noon ET.

Hi Friendos, Today’s newsletter is all about IRA contributions. Back when I was in business school (20 years ago!) I gave a presentation to the Women in Business club called “Who is Roth and What is He Doing with My IRA?” I looked it over recently and was surprised at how few updates it would need to be current for 2025.