Checklists for the things you don’t do every day.

Open enrollment opens. Compare before you are auto-renewed into last year’s plan.

• Choosing a Health Insurance Plan During Open Enrollment
• Understanding and Choosing Employer Benefits During Open Enrollment

Before the first hard freeze across most of the country.

• Preparing Backyard Chickens for Winter
• Winterizing Your Home

Election Day. Registration cutoffs land weeks earlier in many states.

• Registering to Vote and Confirming Ballot Eligibility
• Volunteering as a Poll Watcher or Election Observer

Thanksgiving. The bird order and the guest count are the two things with real lead time.

• Deep-Freezing and Thawing a Holiday Turkey Safely
• Hosting a Thanksgiving Dinner From Scratch

Winter travel season opens.

• Ice Fishing Safety Checklist
• Planning a Backcountry Ski Touring Trip
• Winter Cold-Weather Camping Checklist

The holidays. Schedules and venues fill from here.

• Co-Parenting Through the Holidays After a Divorce
• Planning a Holiday Gathering for a Large Family
• Planning a Holiday Office Party as the Organizer
• and 1 more

The tax year closes. Trades must settle and contributions must post before this.

• Maxing Out Employer 401(k) Matching Before Year End
• Negotiating a Year-End Bonus or Raise Conversation
• Preparing a Year-End Self-Assessment for Performance Reviews
• and 1 more

The coldest stretch of the year. Storms, outages, and frozen pipes cluster here.

• Planning a Ski or Snowboard Trip
• Preparing Your Home for a Winter Storm

Federal returns are due.

• Evaluating a Side Hustle or Freelance Income for Taxes
• Filing for a Tax Extension

June through October is when most weddings happen, as a guest or in the party.

• Attending a Wedding as a Guest
• Planning a Wedding Engagement Party

Atlantic hurricane season begins.

• Making a Hurricane Evacuation Plan for Your Household
• Preparing for a Hurricane or Major Storm

The busiest travel weeks of the year.

• Planning a Fall Foliage Road Trip
• Preparing Your Car for Winter Road Trips

The school year starts.

• Choosing a Tutor for Your Child
• Preparing for an Adult Night Class or Community College Course
• Preparing Your Child for Standardized College Entrance Tests
• and 1 more