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Every month I review my goals and reflect on my progress, practices, and mindset. Looking back, I note that in 7 of the 9 last months, I was pretty disappointed in myself. There were always lots that wasn't going to plan. Everything always took longer to finish than I’d expected.
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But I also do a quarterly review. I ask myself ~the same questions as in the monthly reflections, but over a longer time horizon. Looking back now, I see that in 3 of the 4 last quarters, I’d been thrilled (and surprised) by how much I’d achieved and how well things were going!
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Many rightly asked: so why do the monthly reviews? Unfortunately, they also yield useful insights! e.g. I might reflect that I'm spending too much time on "duty," and I'll plan some changes to try in the next month. I think it's the evaluative, KPI-ish stance I need to drop.
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It might be a manifestation of the human tendency to overestimate how much we can accomplish in the short term and underestimate how much we can accomplish in the long term with consistent effort. Usually I see it in the context of 1 vs 5 years, maybe it's timescale independent.
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Often for me an interval is disappointing wrt goals set specifically for it, but bright wrt to the total sum done one interval below. I think the trick is forcing the same questions(/goals?) for both intervals, so the successes reinforce and cancel out failures/disappointments
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Do you find the monthly evals demotivating and will you focus more on the quarterly? Or are the monthly evals a crucial recalibration that helps you meet your quarterlies? If you think the recalibration is crucial, do you think doing failed wekly evals lead to successful monthly?
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In this context: Imagine a time traveling PM who thanks to dark magic(TM) could give you 100% accurate timelines about all your plans. Spot check: knowing what you already know about your past plans, how would you receive his predictions - actually - truths? A thought experiment.