5 Annual Appointments to Automate Right Now

You'll feel so much better once you do this

Let me be honest: even as someone who helps people organize their entire lives, I still dread scheduling annual appointments - there's something about scheduling a dental exam that makes my brain immediately want to reorganize my sock drawer instead.

But here's what I've learned after years of either completely forgetting these appointments or stress-scheduling them at the last minute: the dread comes from having to think about it over and over again. The solution isn't to get better at remembering—it's to stop having to remember at all.

Let’s Master Adulting Together

Today we're setting up systems so these five essential appointments happen automatically, with minimal mental energy.

1. Annual Physical (+ Eye Exam)

The move: Book next year's appointment before you leave your current one. Seriously, don't even put your shoes back on.

Automation tips:

• Schedule your physical for the same month every year (birthday month works great)

• Ask your doctor's office to automatically book you for next year

• If they don't offer auto-booking, set a calendar reminder 2 months before you're due to call and schedule

• Tack your eye exam onto the same month—many insurance plans cover annual vision checks

Pro tip: Put the doctor's office phone number right in your calendar reminder. No excuses about not having the number handy.

2. Dental Cleaning

The move: Most dental offices will automatically schedule your next cleaning at checkout. If yours doesn't, ask them to call you in 5 months to book your next appointment.

Automation tips:

• Try to book both cleanings for the year at once (January and July works well)

• If they can't book that far out, set a calendar reminder to call and schedule

• Set up text reminders through your dentist's app if they have one

• Schedule the same day of the week and time—make it a pattern your brain recognizes

Real talk: The hygienist isn't judging your flossing habits as much as you think. But they will judge you if you show up every three years with a mouthful of problems that could've been prevented.

3. OBGYN Appointment

The move: Gynecological care isn't optional, even when everything feels fine. Especially when everything feels fine.

Automation tips:

• Find out how often you need to schedule health screenings based on your age and medical practice

• Use your phone's health app to track when you're due for your next appointment

• Many practices will send automatic reminders—sign up for all of them

Reminder: Preventive care catches problems before they become expensive, scary problems. Future you will thank present you.

4. Tax Prep and Review

The move: If you're still doing your own taxes with free software and your financial situation is anything beyond "one W-2 and a savings account," it may be time to get some support.

Automation tips:

• Find a tax preparer and book your appointment for the same time every February

• Set up a folder in your email for tax documents—forward everything there as it arrives

• Create a yearly calendar reminder to gather documents in January

• Ask your preparer about quarterly check-ins if your income varies

True Story: Good tax prep pays for itself. Spare yourself the last minute scramble and bake this into your schedule early.

5. Car Maintenance

The move: Your car manual tells you exactly when to service your vehicle. Follow those recommendations, not the "I'll deal with it when something breaks" method.

Automation tips:

• Many dealerships and auto shops offer maintenance packages—pay upfront, show up on schedule

• Set phone reminders based on mileage AND time (whichever comes first)

• Find a shop that sends reminder texts or emails

• Schedule seasonal maintenance (oil change in spring, winterization in fall)

Reality check: Car repairs cost more than car maintenance. Always. The $100 oil change prevents the $3,000 engine replacement.

Try this: Pick just one of these five appointments and take the first step toward scheduling it. Maybe that's looking up the phone number, or checking your calendar for availability, or simply deciding which one feels most urgent.

💬 READER PROMPT: Did I miss anything crucial? Let me know in the comments below!

Reading: Unreasonable Hospitality by Will Guidara - such an inspiring read on the human desire to be taken care of and the power of hospitality.

Summer Salad: Jordan made this peach and burrata salad and it tasted like summer!

Fewer Better Faves: oh no, another white blouse I want but don’t need, the comfy jeans I’m wearing on repeat, and smitten with this jelly nail polish trend!

1:1 Business Mentoring: No-fluff strategy and support to help you tackle your large and small goals. Get support here

My Signature Online Course: Learn how to edit, organize, and elevate your home like a pro. To the course

Curated Product Recs: My fewer better faves for your home, life, and wardrobe. To the recs

I Wrote Some Books: Actionable strategies to clear clutter, get organized, & elevate your home and life. To the books

Order LifeStyled now from your favorite bookshop! bookshop | target | amazon | barnes and noble | signed copies - now available in the UK, Australia, and New Zealand