I love picking out new a new planner. It’s one of my favorite traditions. Every year finding a fresh new planner to help me build the most wonderful new year feels like such a positive expression of hopefulness. Blank pages for a fresh start. What could be better? I keep all of my old planners from past years. I find it helpful when I need to figure out when to schedule an annual appointment or remember someone’s birthday.

I have a few “must haves” when looking for the perfect planner.

  • The cover must be durable. I carry most of my life in my handbag and I don’t want my planner to fall apart.
  • The planner must have a monthly page followed by weekly pages. I like being able to see the month “at a glance” and then be able to get more into detail such as listing flight confirmation numbers or hotel reservations on the weekly pages.
  • It must be cute.

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The first thing you need to determine when choosing a day planner is the size. Planners range in sizes from very small (pocket size) to very large (desk top size).

I always had normal 5×8 size planners in the past. They were easy to throw in my handbag, keep at my desk, or take with me to meetings. But when I started my current job, I did a lot of intensive travel planning in the beginning. That year, I ended up choosing the Jumbo Lilly Pulitzer Agenda to keep myself organized. Yes, it is very large (as its name implies). It’s about the size of a textbook. It was a bit too big to carry around in my handbag every day, but it was fine to carry to meetings and it fit perfectly in my backpack while traveling. Plus, it came with stickers. Everything is more fun with stickers.  It’s probably a bit extreme for most people, but it helped to have everything at my fingertips. I would recommend this size of planner to anyone who is a student, has a job that requires detailed notes in a calendar, or someone who plans lots of large projects at once, as it gives you quite a bit of room to write. Anyone else might want to stick to a smaller size.

Lilly Pulitzer Jumbo 18 Month Agenda

The second thing you need to determine when choosing your planner is 12 vs. 18 months.

When I purchased the Lilly Pulitzer Jumbo Agenda, I was coordinating multiple photo shoots at once, in different locations, several months in advance. I found that 18 month planners were ideal for me and my needs. I liked that I could start working on January/February details as soon as we got to them, instead of waiting until December to get a planner for the following year and fill in the information once the new one arrived. The only down side to 18 month planners is that I stop using the old one around August/September when I purchase my new one to cover the next 18 months. I just transfer any information past August/September from the old agenda to the new one when I get it.

Since I no longer do all of the in-depth travel planning and coordinating of the photo shoots like I used to, I went back to a 5×8 size planner this time. The 8 ¾ x 11 ¼ size of the Jumbo Lilly Pulitzer Agenda was just too large for my new role. However, I still decided to go with the 18 month planner again this year. Mostly because I like getting a new one in August instead of waiting until December.


I got this year’s planner (first picture) on Amazon.

I got the Lilly Pulitzer Jumbo Agenda I used to use (last picture) at Lilly Pulitzer.

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