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Blog // Thoughts
March 22, 2019

Yearly Planning For 2019/20

Every March, I sit down to plan the coming year. This is how I’m doing my annual planning for 2019 and early 2020.

It’s still cool in Tokyo but the winter chill has gone and as long as you stay in the sunshine you can feel some warmth in the air. I should’ve been paying attention to the beauty around me, but I was still thinking about a recent poll I’d run on Twitter. It seems about two-thirds of my followers have no process for planning their year.

Why I Plan My Year in March

This week I’ve been doing my own annual planning exercise. I do it in March because this is tax time here in Japan and a lot of calendars, mine included, run from April to March.

I already have a theme, which I set at the start of the year, and I’ve had a few months to reflect on what that theme means. It’s already helped me to shape the editorial calendar for my blog and my content strategy for other platforms, especially the new podcast.

Trying to produce everything at once – an annual plan, a content strategy, an editorial calendar and an annual theme – is pretty overwhelming. Breaking those up a little turns them into rolling processes that feed into each other. Right now, my year looks like this:

Winter/end of year: Annual theme and editorial plan
Spring/start of year: Annual planning and business strategy
Summer/holidays: Long-term dreams and big picture
Autumn/mid-year: Evaluation and self-reflection

The Plan Is Surprisingly Simple

How I do my annual planning and think about my business strategy have changed over the years, as I’ve moved from country to country and as my ideas about creative processes and personal productivity have changed and developed. Having a good annual plan is no guarantee of success, but in the years when I haven’t planned, the wheels have always, one way or another, fallen off.

Calling it a plan might even be a little misleading since it’s far less detailed than you might imagine. It’s more like giving myself permission to daydream a little in between the things I do in the day.

The thing about being in a creative business is that the work evolves.
A lot of business advice, like “start with a goal and work backwards to a plan”, doesn’t work, because you often don’t know what the thing you’re making will be until you start to make it.

So much of the plan is thinking about placeholders, or windows in time, to help make the work possible. This thing needs photos, so when and how will I get to the location to capture the images? This thing needs to be printed, so when and how will I learn the steps involved in making the prints, and where will the money for that come from? This thing needs some audio, so when I can get into the studio, and how can other things be managed or put on hold while I’m there?

The core of the plan is always surprisingly simple and involves one big goal for the year. A couple of years back it was just “have a viable online store”. One of the best ones, from over a decade ago, was “have a well-read blog”.

These goals were effective because they drove a lot of smaller projects throughout the year, giving them clarity and focus.

The worst plans, the ones that have always failed me, have been those tied to obvious metrics, like a certain amount of money, or number of readers or products sold. I’ve learnt not to even think about those anymore. My muse cannot be summoned with promises of expensive gifts.

Breaking the Annual Plan into Seasons

In recent years, I’ve used quarters, seasons in fact, to shape my plans.
This is a lesson from Tara Gentile’s very good small business course on CreativeLive. For each quarter, have one clear theme, and 2 or 3 small projects that help to create that goal.

A couple of years back, this strategy worked really well. Last year it didn’t. I slacked off and didn’t stick to the ideas I had. This year, I’m doing it again – lesson learned, year of conviction and all that.

For spring, I’m going with “trade negotiations”, which is a phrase that always makes me laugh, as it recalls the worst plot points of the Star Wars saga. I’m going to be refreshing my online store. It’s important – but something I don’t want to get too worked up about. There are three small projects, a couple of new products, and a whole process of reviewing what’s available from the store, including rewriting descriptions, standardising the product images and so on.

All of this is happening with a bigger re-negotiation of why I’m online. It’s something you may have noticed in my recent pieces on Digital Minimalism and the This Week I Quit series. I even summed up the direction in this comment on Twitter:

Getting Down into the Quantum Realm

This year, I’m doing something new. I’m going down to the micro level in thinking about each day and what fills it. This is the first time I’ve done this since 2014, when I wrote about “work blocks,” where I codified this in detail. In recent years, writing has come back to the centre of my creative practice. Health has become a greater priority. And I find myself wanting to spend less and less time in front of a screen and more time working with physical things. So, a rough map of my day for the coming year looks like this:

  • 6.50 Rise and breakfast
  • 7.50 Write
  • 9.50 Exercise
  • 12.00 Lunch
  • 12.50 Studio and workshop
  • 16.50 Downtime and relaxation
  • 17.20 Cooking
  • 19.00 Dinner
  • 20.00 High-quality leisure
  • 22.00 Bath and bedtime routine
  • 23.00 Sleep
  • I’m also looking at my daily themes, which are single phrases that guide each day of the week and help me plan my week, something I adopted after being inspired by Mike Vardy. These themes help to group activities and also contain distractions. So, I check emails only twice a week, on my “crafting order” days, Monday and Friday. And, I group together “learning” activities on Tuesdays, which includes weekly Japanese lessons and often end with me watching a score of how-to videos, making notes and deciding on things I want to try soon.

    But, like any productivity-oriented thing, they can get restrictive. After a while, the daily schedule becomes filled with the same small number of activities. And everything becomes a chore with no room to play. Then your inner child, the creative sprite that brings disruption, joy and surprise to your life, goes into hiding.

    I started the week going through a thesaurus, finding alternative words for the daily themes I use: order, learning, self, making, family and future. And I ended the week making a little deck of cards, a set of prompts, to use during the year. For each theme there are 12 cards, with the theme on one side and an alternative definition on the other. At the start of each week, I’ll flip cards and redefine each theme for that week in a new way. So “learning” might become wisdom or insight, which hopefully will push me to be less stale about the shape each day can take.

    The Planning Is not the Goal

    It’s easy to get obsessed about this stuff. Planning can take over the mind. We start to imagine we’ve already done all the stuff we’ve planned to achieve. And in a weird way, that can rob us of energy and motivation.

    The best plans are like airplane wings: light and flexible enough to adapt to whatever the coming year throws at us, but strong and stable enough to keep us on course. The right combination of the two ensures that we can take off and land successfully, day after day, week after week.

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