Caitlin's Corner

Are We 'Helicopter Financing'?

Last month I was tossing and turning after learning about an experience my daughter was having on her flag football team. I had shown up to help out at her practices and, for the first time, I saw how she was being treated by her all-male teammates. These are third and fourth grade boys- kids I know to be kind on their own. But together, they banded against her: picking on, criticizing, and effectively shutting her out.

It was one of those moments that tears your heart wide open. I’m not proud of the words I wanted to shout at those boys. But I watched my daughter handle it with grace, and I’m grateful I saw it firsthand so we could make space to talk more about it at home.

When we did, it struck me that as parents, we pour enormous energy into imagining worst-case scenarios, like accidents, illness, and dangers we desperately want to shield our kids from. But we spend far less time preparing them for the more common struggles they will almost certainly face: exclusion, criticism, failure, and sometimes even being the one who hurts others. I caught myself wishing I could whisk her away to a friendlier team, but the truth is: she’s guaranteed to face versions of this again and again- as a child, and as an adult.

And that truth made me realize that we do the exact same thing with our finances.

We burn mental energy on unlikely catastrophes:

Is it possible? Sure. But the odds are about as good as winning the Powerball several times.

What’s far more likely is this:

So rather than letting fear of the extreme steer our choices, we can plan around the scenarios that actually happen.

The best part is that when we have confidence in our plan, it doesn’t just allow us to protect against the hard times. It helps us make the most of the good times. Remember that hitting your financial goals is more likely than the world falling apart in your lifetime. So, when you reach your next milestone, how will you step into that new chapter?

🫶 P.S. If you'd like some help with your plan, or if you don't know where to start, book a free strategy session ​here​.

Q4 (Financial) House-Cleaning Tips

The fourth quarter is upon us! Here are some tips to help you get ahead of the end-of-year scramble:

👉 Check your retirement contributions Make sure you’re on track to max out (or at least capture your employer match) in your 401(k), IRA, or HSA before year-end.

👉 Use your FSA dollars Flexible Spending Accounts are often “use it or lose it.” Schedule doctor’s visits, stock up on prescriptions, or buy eligible health items before the deadline.

👉 Review tax strategies Consider ​Roth conversions​, charitable donations, or other year-end moves that could reduce your 2025 tax bill.

👉 Check beneficiary designations A quick but often-overlooked task. Make sure the right people are listed as beneficiaries on retirement accounts, life insurance, and investment accounts.

👉 Exercise some NQSO (Non-Qualified Stock Options) If your employer issues NQSOs, which are taxed as ordinary income when exercised, then having a better idea of your expected tax bracket will allow you to exercise just enough to stay within your target bracket.

👉 Plan year-end spending Map out holiday budgets and big expenses to avoid a debt hangover in January.

👉 Update your goals + 2026 vision It's not too early to reflect on your progress this year. What needs adjusting before 2026 sneaks up on you?

What I'm Reading

📕 A Helicopter Parent's Dream Come True​

Katherine Martinko hit home again when she sounded the alarm on these creepy Skecher shoes. I wonder if she knows how much of a parallel this parenting trap has with our financial tendencies.

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Nov. 5 - Open Enrollment Edition: Your Benefits Questions Answered​

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