Mid-Year Planning

I just read MacSparky’s post on mid-year planning.
I prefer to do quarterly planning (as MacSparky also says in this post). I feel like Monthly plans are too short and yearly plans are too long. Too much happens in a year for a yearly plan to stay on track. A month usually isn’t long enough to finish a substantial project. Quarterly is the sweet spot for me.

I also do weekly reviews and plans to make sure I stay on track with my current quarterly goals. I manage all of this using notes in Obsidian and projects in Things. Things Someday is useful for parking ideas I’m not ready to work on in the current quarter. In the last month of the quarter, I will start reviewing my Someday tasks and projects in Things and deciding if any of them should make it onto my next quarter’s plan. By the time the next quarter begins (tomorrow in this case), my quarterly plan is pretty full and tonight I will do another review and add/remove items as the quarter is set to begin.

How do others manage their longer term planning and goals?

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Sorry in advance, I suspect this is tangential… but I have been thinking about this a lot lately.

Specifically, I’ve been wrestling with the notion of “arbitrary” calendrical review horizons. My projects never fall neatly in weeks, months, quarters, or what have you. I sometimes work on weekends. I sometimes need to drop everything and prioritize a new project completely for a few days.

Yet, most productivity systems and philosophies emphasize the role of the calendar. Getting Things Done has a weekly review. Scrum features daily and weekly cycles. Bullet Journaling uses “weekly spreads.”

I imagine many of these conventions come from their basis in the office world, where 9–5 Monday–Friday is technically a thing. Still, I’m curious about alternative frameworks for productivity-over-time.

Basecamp’s Shape Up is based on six-week cycles. But that’s the only example I’ve come across where the structure isn’t rooted in some convenient calendar-based rule, and it’s still based on weeks.

I guess I’m looking for ways to make the time horizon fit the goals, instead of making the goals fit the time horizon.

(Neat topic!)

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More powerful still is the whole apparatus of annual / quarterly commercial, financial, and regulatory reporting cycles. For publicly-traded companies at least, the five day workweek matters less than the demands of the Security and Exchange Commission’s calendar of filing deadlines. The non-public companies and non-profits that swim in their wake end up adopting that annual / quarterly calendar by default.

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The job I get paid for is M - F, but even at work projects often don’t fit into the quarterly boundaries either. It is arbitrary, but I think of it more in terms of having a regular high level review and goals beyond the day to day task management that I’m usually focused on. On my Q2 plan I have an item marked with (will continue into Q3), knowing in advance it wouldn’t be done on June 30th.

If I have an item that keeps getting pushed forward to the next quarter and never gets completed, that is also a trigger for me to question if I am really committed to it. I’m looking at an item right now that I spent zero time on in Q2. This tells me I don’t really want to do it. I’ve had 90 days to get started on it and always found some excuse not to. I will not be adding it to my Q3 plan. Having these moments of brutal honesty is also important.

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