Financial Planning Topics for Fall 2025
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Written by Ryan Stille

September 4, 2025

Fall is here so it’s time to kick off our second strategy session of the year. Two distinct meetings allow us to cover a broad range of financial and life planning topics. This results in easy flowing conversations that help our clients travel in the right direction.

It’s hard to eat the elephant in one meeting a year. Financial decisions can be overwhelming and we all need time to think through our options. By chunking out planning and strategy we’re able to manage expectations through a repeatable process. It’s a win-win as progress arrives in accumulating steps that add up.

Our mission is simple. Serve clients as they liked to be served so they can discover what exactly they want with their time and money. This sounds easier than it is in real life, so how do we pull this off?

Our client service calendar covers different themes each season. Here’s our fall topics.

  • Insurance: what do you own, who does it protect, and how long will it last? Three straightforward questions worth answering. As a reformed insurance salesperson, I no longer sell policies but happily pay premiums on my family’s coverage. Why? Insurance acts like bubble wrap around our financial plan; it keeps us antifragile regardless of how life plays out.
  • Taxes: rough out an estimate of your year-to-date earned income and compare it to where you ended last year. Are you withholding enough Federal income taxes to avoid underpayment penalties?
  • More Taxes: based on the exercise above, what’s your estimated adjusted gross income? What’s your estimated taxable income? The July tax bill has temporary and permanent provisions all taxpayers should be aware of. Your eligibility and participation are decided by your income.
  • Interest rates: what impact will a cut to interest rates have on your current debt structure and duration? Does it move the needle?
  • Ownership and beneficiary designations: who owns what and does it support what you want? Reviewing ownership and titling of accounts and property cuts surprises.
  • Estate documents: when was the last time you reviewed your legal documents? This is always a challenging conversation as no one wants to imagine themselves having to use their estate plan. Eventually we all will.

I can say the following with a high degree of confidence, having collaborated with people and their money for the past thirty years. Without prompting, investors will defer decisions and changes for as long as possible. This is human nature; our brains were designed for this sort of thing.

The art of planning takes practice, repetition, and mutual trust. Sure, investors can save money and do this on their own. However, in my experience, most are focusing their energy solely on investment decisions and frequently miss the softer shades of financial planning.  These investors tend to oversave and underspend, as their focus lies in account values as opposed to holistic planning. But remember, a portfolio isn’t a plan.

All this tends to create expensive outcomes in the long run. In retrospect, it makes the cost for ongoing advice and strategy seem quite reasonable. So, is it worth it? That’s an individual question based on the value of your time and money.

Investors should ask themselves, in their best judgement, will we add at least one percent to your annual returns through better investment choices and/or save you more than one percent in time, worry, and recordkeeping and/or save you more than one percent in costly behavioral mistakes we may convince you not to make?

It’s never close. The multiple of what we deliver exceeds what we charge by a significant margin. Ultimately though, it’s not our decision as it’s not our money. Investors need to figure out what’s best for themselves. Not by ignoring financial decisions today but by asking questions and continuing to learn as their wealth and complexity expands.

Not all financial planners/advisors are the same. You have choices—choose wisely.

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