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Here in the Northern hemisphere, winter is drawing in. We’ve just turned the clocks back, and things are starting to get cozy and introspective, especially for us wool-gathering types. These are the days when self-care feels most natural.

In other words, this is a great time to start planning the year ahead. January is just too late! And we’re usually tired after the holidays.

Here’s a simplified version of how I build a year. You can further simplify by skipping anything you don’t need. Of course, add anything you feel is missing!

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Preparation is important. Safety first, meaning there will be no scolding from the Inner Critic. Illogically, comfort is also first, meaning I like to do my planning in pleasant surroundings, with a nice beverage and possibly snacks. (This year I went to Tartine in San Francisco’s Inner Sunset for a Tiger’s Eye, aka a chai latte with an espresso shot. It may or may not have been the whole secret to a successful planning sesh.)

Planning, like so much of self-care, is the opposite of a bubble bath. Planning is more like putting on the snow tires and checking the oil. Which is why you might want to do your planning while taking a bubble bath or drinking a glass of champagne, or doing it with your sparkly pens in a nice café.

Start with a review. This can get a little gnarly, especially when we look at regrets, missed goals, and the like. So get your inner critic set up with snacks, and put her in the corner. Then ask questions like:

  • How did last year go?
  • What was good?
  • What do I not want in 2020?
  • What did I learn?
  • What do I value?
  • What worked?
  • What didn’t work?
  • What do I regret?

This is the nitty-gritty part, but it’s not an action-taking part. This is just a letting yourself know the truth piece. (The truth is always a good starting place.)

I also look at the concluding year’s projects. What’s incomplete that I want to finish this year? What would I like to continue in the coming year? What do I just want to call time of death on?

A moment of satisfaction. If I did a reasonable job planning last year, and I checked in with my plan from time to time, then I will have completed projects and highlights to celebrate. I might put a spa day in the calendar right now. Or maybe I just sit there in that café and feel really pleased with myself. You celebrate any way you like!

Words of the year. I recall my word for the preceding year, and think about how it informed what I did. Then I choose one for the coming year, and I don’t tell anyone what it is until the end of the year.
(My words for 2019 were consolidate and refine.)

Plot out the big picture. I start with the fun stuff, like vacations and retreats. (This is also the self-care part!) Makes the work stuff easier to schedule. I put those trips and retreats on my working calendar, and I also block out a time to make bookings and pay deposits.

Then, set some goals. After I’ve had a good look at my triumphs and disappointments, I have a sense of what I’m ready to commit my time and attention to. (For sure, Junko Okamoto’s Astrid.)

Goals might be the sexy part of planning for you. Or maybe you’re disenchanted with goals these days, in which case you could look at a few big projects. It’s sort of the difference between process and product. You can experiment to find what works for you.

Whether you prefer goals, projects, or something else, I suggest limiting your targets. Fewer goals means easier goal management and greater chance of success.

What’s all this going to require of me? Probably a lot of consistent action, time, and attention. Plot out what that looks like so you can spot any obvious problems. If there’s something you know you’re not actually willing to do, that’s good information. There’s always more than one path to fulfillment.

Who can help? You know a lot of people, and some of them are highly skilled and would be thrilled to help you. I like to plan in solitude, and execute in community.

Update your plan. As we used to say in the project management world, “A plan is a picture of how it ain’t gonna go.”

There will always be surprises that we can’t plan for, but can only react to. Take a few minutes at the end of your process to book regular reviews—quarterly, monthly, or any rhythm that seems good. I like an hour-long mini-session every month.

Finally, summarize your year on a single page. I like to have something I can see on my phone. (I use the Notion app for this, and for everything else, by the way.)

My 2020 on one page looks like this:

  • 2019 word(s)
  • 2020 word(s)
  • 2019 highlights
  • 2019 regrets
  • Values
  • What am I saying “no” to?
  • 2020 vision: goals, milestones, events, aka what I am saying “yes” to
  • What’s required? What do I need to do in order to pull that off?
  • Who can help?

What about you? What do you think about when you plan your year? Pop your suggestions into the comments!


Editors’ note: Max isn’t tooting her own horn here, but we’d like to do it for her. We both are avid readers of Max’s delightful weekly emails. If you’d like a moment of laughter or flash of insight in your inbox every Tuesday, sign up here.—Kay and Ann


ILLUSTRATION: The Traveller’s Guide to Madeira and the West Indies (detail), Anonymous, 1815. British Library, Public Domain Mark 1.0.

About The Author

Max Daniels is a research-based life coach whose weekly emails make us laugh with recognition and rethink everything we thought we knew. Her new book is Meals at Mealtimes. What a concept!


  • Love it, love it, love it! This is gentle push I needed to get myself going today. Thank you for concrete & easy ideas & inspirations that I know are well within my grasp to achieve & accomplish if I just slow down & create the space for me to be present.

  • Right on time and right on the money! THANKS!

    May I also suggest, for the more visual/kinesthetic types: a vision board?
    Last January was my first ever vision board workshop, well equipped with snacks AND libations. I made one for 2019 and promptly buried it in the trunk of my car until a few weeks ago. Shocking to see how much of it came true regardless of it being out of sight and yet also satisfying because I must have really wanted those things to manifest.

  • “Plan in solitude and execute in community.” I love it.

  • Max you are a beacon of awesomeness. I’m definitely making a plan that includes what I will say no to. I’m getting better at it, but I still need lots of practice. I still undervalue my own time, or maybe it’s also the trap of “If want the job done right, do it yourself.” Probably and paradoxically both.
    The idea of a hard look at the year is a little scary, even though I know there’s a lot to celebrate.
    Thank you for this, and all of your cheerleading. I would have signed up for your newsletter ages ago, but I just didn’t know.
    I hope you have a joyous holiday season.
    Ps. How do you decide what your words will be? How many do you choose? As lover of the English language, I’m intrigued.

  • Thank you, Max. Lots to think about. 2019 was quite a year for me. Best self-care event: Shakerag Knitting weekend!!! And thanks Ann and Kay — I shared this morning’s letter with my husband. I keep telling him, it’s so much more than knitting. XOXO

    • You are absolutely right about the Knitter’s Weekend. Already looking forward to that little bit of heaven.

  • “Plan in solitude and execute in community” – thank you.

  • Max is the best! I love the idea of a Word of the year and using it to inform my actions and decisions. Thank you again for your continued guidance and wisdom!

  • This would have been really helpful for me thirty-five or forty years ago. Now, in retirement (but still very busy) I take a more casual approach, though I do still plan for the big things (like vacations!). My word of the year for 2019, which was never a secret, was “nevertheless.” It was a wonderful word to live by!

    • WHAT a good word! Love it.

  • Some of us are not planners, and really should not be. We may let Destiny or other intuitive elements guide us. However, activities like finding words for the year may support an interior search for our path. Thank goodness for a diversity of paths, and thank Max for thoughtful exercise ideas.

  • Wow. That was a really interesting read. Although from my own point of view most of it could have been written in a foreign language. I have such massive admiration for you people who can plan out a year (even roughly). I can’t even manage to make a plan for tomorrow – and if I did I don’t suppose I’d manage to stick to it lol. I will pass the link along to my sister in law though – she’s the planning type.

  • So many good ideas! I plan to add to my goals the things I will say “no” to – and, definitely a word for the year!

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