My Quarterly and Yearly Planning Routine (Loose, Dreamy, and Done Together)
Part 5, the final post in the My imPERFECT Planning Routine series. New here? Start with the overview of the whole system.
Quick note: this post contains affiliate links. Full details in the My Tools section at the bottom.
Here's the truth about planning six months ahead: I don't really know what life is going to look like that far out. Neither do you. No one does.
For a long time I thought that meant long-term planning wasn't for me. If I couldn't lay out a detailed plan, why bother? But it turns out the problem was the plan itself, not the planning. Quarterly and yearly planning doesn't have to be rigid. It took me SO long to realize that. Mine is the loosest layer of my entire “planning” routine, but I actually think it’s the most important one.
The rhythm: four times a year, scheduled in advance
My husband and I do three quarterly check-ins a year, plus one bigger session at the end of the year that doubles as both the annual check-in and the fourth quarterly. Four check-ins total.
And here's the mechanism that keeps this ritual alive: at that year-end session, we schedule all of next year's sessions. We stay flexible on the actual day, life happens, but the targets exist on the calendar all year long. We never have to remember to do quarterly planning, because past us already made the appointment. It's the same simple trick as the rest of my routine, applied to the biggest layer: lower the friction of coming back.
We use the Hustle Sanely goal setting method for all of these sessions. It gives the conversation just enough structure without turning it into a dry business meeting.
Goals and habits are the anchor
Even at this zoomed-out level, goals and habits are still the spine. The quarterly session is where the yearly vision gets stepped down into something a season can actually hold, and where we look honestly at how the last quarter's goals went.
This is the layer that feeds everything below it. The quarterly goals become monthly focuses, the monthly focuses become weekly plans, and by the time any of it reaches my planner, a big scary goal has become a small doable task. I walked through a full example of that laddering in the monthly post.
Everything else is “pie in the sky”
Beyond goals and habits, the rest of the check-ins are intentionally dreamy. Things we want to do. Things we hope for. Things we are absolutely not holding ourselves to too tightly.
Real examples from our pages: building our house. Savings goals. Salary and work goals. The kind of things that we don’t have total control over, but our actions can be a major determining factor.
And when a dream sits quarter after quarter? We reevaluate against our current situation and adjust. Sometimes that means breaking it into something smaller, sometimes that means shifting the timeline, and sometimes that means dropping it all together. It just depends.
Stub out what you already know
The one concrete thing I do at this level: stubbing out known events. Specific dates that already exist, rough timing for things we want to make happen. Vacations, big family stuff, work seasons.
I'm not making a detailed plan for six months from now. I'm just placing flags so future me can be prepared and isn't surprised. When the monthly trigger list scan happens later, those flags are already standing there waiting.
Why we do it together
This is the only layer of my routine that's shared, and it started simply: we both value improvement as people. The conversation about what we want the next season to look like was already happening informally, and over time it just became more structured until it turned into a standing ritual.
Doing it together means we zoom out as a team. We get on the same page about what the next season is for, dream a little without the pressure of making it perfect, and walk away pointed in the same direction. The goals that come out of these sessions aren't mine or his, they're ours, and that changes how the whole year underneath them feels.
A loose vision with some dates on it
That's really the whole philosophy of this layer: A loose vision with some rough dates on it, and that's enough.
Enough to keep the daily, weekly, and monthly plans pointed somewhere. Loose enough to survive contact with real life. And scheduled just firmly enough that we never skip it.
The whole series
This wraps the My imPERFECT Planning Routine series. The full system, layer by layer:
The overview: how the four layers work with the grain of time. [link: https://imperfectplans.com/imperfect-blog/my-imperfect-planning-routine] Daily: three check-ins and the one evening habit I never skip. [link: https://imperfectplans.com/imperfect-blog/daily-planning-routine] Weekly: my six-step reset, where everything comes together. [link: https://www.imperfectplans.com/imperfect-blog/weekly-planning-routine] Monthly: the trigger list that cures the blank page. [link: https://imperfectplans.com/imperfect-blog/monthly-planning-routine]
And if you want to try a quarterly reset yourself, The Imperfect Practice Kit includes The Quarterly Reset page, a simple one-page version of exactly this session.
Or start smaller: the Imperfect Practice Sheet is my free one-page weekly sheet, the entry point to the whole system. Grab it free here.
My Tools
Everything that shows up in this routine, all in one place:
The planner: Laurel Denise Anne, my daily driver. Code IMPERFECT10 for 10% off. [link: https://tidd.ly/3IyLSgc]
The goal planner: Peacefully Productive planner from Hustle Sanely, the method behind our quarterly and yearly sessions. Code SARAH86. [link: https://hustlesanely.com?bg_ref=PNiiHLyeg4]
The printables: The Imperfect Practice Kit, 7 pages including The Quarterly Reset. [link to shop]
The freebie: The Imperfect Practice Sheet. [link to signup]
Disclosure: Some of the links above are affiliate or referral links, which means I may earn a small commission if you shop through them, at no extra cost to you. I only share tools I genuinely use in my own routine. Thanks for supporting Imperfectly Planned!
