Goals life Planners

Planning Day

May 12, 2021

I loved the comment section yesterday. I think I feel convinced that a) those AGOLDE are fine if I want to try them (and I do); b) white denim shorts are a good idea; c) skorts & dresses are also a valid way to go and don’t need to be as fussy as I had imagined.

I WILL report back on summer wardrobe escapades.

But first I just want to discuss the concept of Planning Day and how I am obsessed with the idea. This came from listening to Lisa Woodruff’s Organize 365 podcast episode from yesterday. She offers her own guided planning day, in which you spend a dedicated ~5 hours sorting through life goals, priorities, and much more. In her case, her program is designed to be used with her custom planners which she sells.

I love this idea. Not specifically her sessions (though I am sure they are amazing and honestly I may pay for the recording just to see what it is like!). But just the concept of putting a PLANNING DAY on one’s calendar (in one’s planner . . . how meta) and dedicating an entire day or half day just to plan the next few months.

I have been thinking about Retreat Days and had a goal of building in one per Quintile. I am toying with the idea of making my Retreat Days into quasi-planning days, because honesty that had been part of the point anyway. BUT I don’t want to spend my entire Retreat Day planning, either. Here’s one potential Retreat Day schedule (we will ignore any COVID concerns, this is theoretical!):

5:00 usual AM stuff, workout, etc

9:00 go for a walk in a beautiful setting, spend time just thinking

10:00 massage + pedi

12:00 lunch somewhere nice

1:00 unrushed luxurious planning session (guided or not) ideally in a nice setting

6:00 home to be with family

pretty stack of planners

I am on call this week BUT not on nights/weekends. We have one more remote provider that covers ~6-8 weeks of nights/weekends throughout the year in exchange for coverage of his patients. IT IS GLORIOUS. It must be somewhat like this sometimes in places where there are fellows. If I were in private practice and in charge, I would have everyone chip in to hire a PA or NP that could cover calls at night (most do not require physician/specialist levels of knowledge and then a physician could be on backup). And that person would have zero daytime responsibilities or perhaps just some flexible project based work they could do whenever so it would be a pretty cushy job (after all, many nights would be 0 calls).

I am definitely in fantasy mode today but I guess there is nothing wrong with that! HAPPY WEDNESDAY. Does anyone currently engage in a planning day ritual? How often? What does it look like? What has it done for you? I want to know!


  • Reply gwinne May 12, 2021 at 7:46 am

    So this is super timely for me. I ordered a 90 day undated planner with some guiding questions to use May 15-Aug 15 (academic summer) as I am simultaneously starting this new season, entering post-vaccinated life, and starting a new phase of my career.

    I am taking a day next week to stare at a wall (almost literally) and then I’d like to spend a retreat day or two of planning (as much as I can while Tiny Boy is at school, so basically 9-2). cannot wait!!!!

  • Reply Sam May 12, 2021 at 8:01 am

    I loved seeing all the comments yesterday too! I’m also short, and just ordered shorts online that were longer and frumpier looking than I expected. I’ll go back through the comments this weekend to get some ideas of what else I can try.

  • Reply Marcia (OrganisingQueen) May 12, 2021 at 9:29 am

    I enjoyed last year’s quarterly planning so much (you know, once my 2020 plans mostly fell by the wayside) that I now do quarterly planning too. I don’t take a day but I probably use about 90 – 120 minutes (so one full “free” evening without coaching clients) and do my quarterly planning in all of my “roles” – wife, mother, coach, full time job, etc. I do recommend thinking time beforehand. I write out what I want to get from my session, and have the session about 3 – 7 days out, and then I turn off my phone, etc. so I can focus.

    It’s worked so well – I’ve done about 4 of them so far.

    So all that to say – definitely include some thinking time and actual planning time, and if things need to change, well, there’s my monthly review for that.

  • Reply Chelsea May 12, 2021 at 1:17 pm

    I very nearly signed up for the most recent Planning Day with Lisa Woodruff but decided at the last minute to wait for the work-focused planning day. I’m in the process of applying for a new role in my company that would involve a lot of long-range planning, and, if I get it, I think formally signing up for the Planning Day (though I might just watch the recordings) would be a good investment. Obviously planning is something can do on one’s own, but I always appreciate Lisa’s insights, and I think it would be very worth it at least once.

    • Reply Sarah Hart-Unger May 12, 2021 at 1:20 pm

      I agree! I honestly love her ideas and how she thinks about things.

    • Reply Sarah Hart-Unger May 12, 2021 at 1:53 pm

      And you just convinced me – bought work box, planner, and signed up for the work planning day (corporate) for June 4! Even if it’s just a one time thing I think it will be interesting and fun.

      (Lisa had previously gifted me access to the 100 day program but I bought all of the above myself)

  • Reply Emma May 12, 2021 at 2:31 pm

    I do about a half day at the beginning/end of each semester (I’m a professor, so Spring, Summer, Fall, although I guess technically these are trimesters) and find it essential. I also enjoy the Organize 365 planning days (I’ve done one work and one home) not so much to do the planning or learn how to plan but because it’s fun to hang out with a bunch of people who like planning! So I think you’ll have fun even though you already know how to plan!

  • Reply Brooke May 12, 2021 at 2:59 pm

    I did the Powersheet 6hr live session at the end of last year when they went virtual (it was previously is person and way cost prohibitive). I really enjoyed it and would do it again. Carving out dedicated time that was not in 1 hour chucks allowed me to get in the mindset I wanted to be in.

    • Reply Sarah Hart-Unger May 12, 2021 at 3:10 pm

      Oh that’s awesome! Love their stuff, I just find the design soooo pretty and fresh.

  • Reply Sunny May 12, 2021 at 3:53 pm

    I wanted to do quarterly retreat days but never made that happen especially after the pandemic. Some thing I’ve started doing is blocking out a monthly morning retreat. There are about 3,5 hours when both of my children are out of the house, twice a week, so I take that time once a month to do my monthly planning which takes probably 30 minutes to an hour, and then I do other things like take a walk, do yoga, take a nice relaxing bubble bath, eat lunch and watch a favorite show. I really look forward to that time and I’m glad I have it blocked off on my calendar as time off work.

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