October 2025 Quarterly Planning Spotlight

Welcome to the October edition of the financial planning spotlight! Topics top of mind this quarter are Health Insurance, End of Year Tax Planning, and Values Based Spending.

Health Insurance

As usual, health insurance is a sh*tshow. This year is no different. In fact, the government is basically shut down right now because of it.

I look at health insurance conversations differently than many financial planners. I focus on increasing peace of mind rather than merely lowering premiums or saving in an FSA or HSA for out of pocket costs.

Three aspects I talk about with clients that have to do with peace of mind:

1.        Being able to get care when you need it. This means you need to have doctors and a network that can see you. You need to be familiar with the system. Don’t discount how important it is to stick with providers you like and can get an appointment with. Even if it costs more money. Change is hard. Don’t do it if you don’t have to.

2.        Unpredictable costs suck. I used to be on a High Deductible Health Plan (HDHP). I hated it because I was always weighing whether it was worth going to the doctor and paying some stupid amount out of pocket (and it was never the same it seemed from one visit to another). Now I have an HMO and I know how much visits will cost. Is it the most optimal financially? I’m not sure, but it feels really good to have predictability.

3.        Picking a plan that works for YOU. If you have coverage through an employer, you likely only have a few choices. If you don’t, we are lucky enough to live in a time where it’s possible to get insurance through an exchange under the Affordable Care Act. However, picking a plan can be daunting even if you’ve done it a hundred times before. Look at three numbers to compare plans. 1) The cost of just the premiums and no care. 2) The total cost of premiums plus out of pocket maximums if sh*t hit the fan. 3) The estimated costs under each plan for your particular medical needs. <— This one is the hardest to figure out but it can be the most important to try. I have a spreadsheet for this comparison of course.

Mistakes with health insurance can derail your financial plan. It’s worth spending some time making this choice and getting help if you need it.

End of Year Tax Planning

I’m always asking for pay stubs. I know. Here are the items I’m looking at when I do Q4 tax projections:

1.        How does your withholding compare to what your estimated taxes are. You DON’T want surprises next spring. There is still time to withhold extra for the rest of the year or update your W4 to withhold less. This year was especially tricky because tax law changed mid-year.

2.        Where are you at with regards to retirement plan contributions? Are you on track to max out before the end of the year and may miss out on matching? Does it make sense to update your split of Traditional v. Roth contributions? Are there other retirement plan considerations we need to address before December 31?

3.        What is going on with your investment accounts that will affect your taxes? Taxable brokerage investment accounts can produce income in the form of interest and dividends, as well as generate gains and losses. This includes accounts that hold vested RSU shares and ESPP shares. There may be changes we can make before the end of the year that can help mitigate some of these impacts.  

Values Based Spending

As we go into the holiday season, it’s important to talk about spending. I recently read “The Art of Spending Money” by Morgan Housel. It wasn’t great, but I got two important insights while reading it.

1.        Everyone should be spending money according to what is important to THEM. No one else. Not me, not their friends, not their family, not their co-workers. This is REALLY hard to do.

2.        There is deep tension between the you of today, and the you of tomorrow, when it comes to spending money. It’s not enough to simply say “Live for today” or “Save for the future”. We do not know how long we will live. Instead, seek to “minimize future regret”. This is hard because the things you will regret will change over time. But it’s worth trying to do because it can help you spend your money in a way that is meaningful to YOU.

Please reach out with questions or book time with me if I can help with your financial planning or investment management needs!