Planning For 2023 Using Obsidian

The core shift behind a successful 2023 planning system is replacing rigid, short-term targets with flexible, measurable progress—and then backing that up with a monthly review loop that feeds a lightweight yearly template in Obsidian. Instead of chasing streaks that collapse after a missed day, the approach tracks habits by averages and long-term trajectory. That change matters because sustainable behavior rarely moves in a straight line; it fluctuates. By aiming for an average (like walking 10K steps per day) rather than “10K every day,” the plan tolerates low weeks early on while still rewarding steady improvement over time.

A second pillar steers goal-setting toward controllable inputs. Chasing outcomes such as subscriber counts or monthly views is treated as a poor target because those numbers depend on factors outside day-to-day control. The practical alternative is to commit to behaviors that drive results—upload frequency, content quality, thumbnails, and related craft decisions. In a job context, the same logic applies: promotion isn’t reliably controllable, but proactive work and taking initiative are. The system’s emphasis is less about predicting outcomes and more about building repeatable actions that can compound.

The third—and most operational—change is a monthly review habit that keeps priorities current. Each month’s note includes a “year’s goal” section, so the yearly plan doesn’t sit untouched until December. When someone is on track, the system keeps going; when progress stalls, it triggers questions like whether too much time is being spent on one thing or whether priorities need recalibration. This monthly cadence then supports a yearly review template that’s intentionally simple: reflection and resolution are the two main sections.

In Obsidian, the yearly note is generated using the Periodic Notes plugin with yearly notes enabled and stored under a dedicated folder (Journal/yearly). The yearly template is structured around headers for reflection and resolution, with reflection sections such as “what happened this year worth remembering,” “habits,” “relationships,” and “work.” Many of these sections are pre-linked to monthly notes, so the “best of the year” can be assembled by quickly checking each month and copying what stands out. Favorites and standout content—articles, tweets, YouTube videos, and other media—are tracked monthly and then surfaced in the yearly note.

Habits are handled through Obsidian tracking and queries. For numeric habits like weight, the system uses query blocks that can be filtered by start and end dates to produce graphs and summary statistics. For yes/no habits like meditation, it relies on frequency summaries. New habits are also logged throughout the year so the yearly resolution can select which ones to commit to.

Relationships are tracked via Monica CRM, used to log interactions and generate alerts when outreach hasn’t happened within a set timeframe. The yearly note then includes a short reflection on career progress and relationship-building, followed by a resolution section that stays intentionally small—typically a few bullet points and rarely more than three major goals—to avoid overwhelm and the common mistake of overestimating what can realistically be accomplished.