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The Boring Newsletter, 10/11/2026 🍂☕

What Could be Cozier than a Clipboard and a Checklist?

Hi Friendos,

Here in the Northeast, I think we’ve entered cozy season. To me, there’s nothing cozier than a clipboard, a checklist, and the warm security of finishing items on the list. I am all about organizing one’s personal finances to be boring, because to me, boring means no anxiety.

It’s been a while since I’ve written about my annual checklist, family finances binder (great to have no matter your household composition), or year-end financial planning. So if you’re new around here, I would recommend reading those newsletters.

It’s also been a while since I discussed medical insurance annual enrollment, and shared my story highlighting that you must save a copy of your benefit selections. You should also check your paystub after the elections are effective to make sure the withholding amounts are what you expect them to be.

This fall, my own financial to-do’s consist of the following:

  • [DONE] Review my investments to see if I need to rebalance my portfolio to remain in line with my desired asset allocation. If I only owned target date funds, I would not need to do this because the fund portfolio managers would do it for me.
  • [PENDING] Transition from two-factor authentication to passkeys and/or security hardware for my investment accounts.
  • [PENDING] Update photos of our home and belongings for insurance purposes, so we have some record of things in case of fire, flood, or other adverse event.

Now that I confessed my pending items to all of you, I have some accountability partners! I will give updates on these in the next month or two. 🤝

-Stephanie