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The quarterly personal review

Kaitlyn Dineen · Feb 2026 · 3 min
The quarterly personal review

I was listening to the author of Essentialism on a podcast, and something stuck with me.

New Year's works as a reset not because it's magical, but because we pause. And if that pause is healthy once a year, we probably need it more often.

He talked about treating your personal life the way many companies treat strategy. A quarterly offsite. Time away from the noise to reflect, recalibrate, and make sure you're still pointed at the right North Star.

I've been doing some version of this for a year. It's quietly become one of the most grounding practices I have.

A living North Star document

I keep a living North Star document. I review it, edit it, question it. Not to optimize every moment, but to make sure I don't drift too far in the wrong direction while things are going well.

That last part matters. Drift doesn't usually happen during the hard seasons, when you're paying close attention. It happens when things are good and you stop checking the compass. You look up a year later somewhere you never chose to go.

The document is how I keep choosing on purpose.

Reflection is a leadership tool, not a luxury

There's a quiet bias in business culture that treats reflection as indulgent. Real operators execute. Thinkers journal.

I think that's backwards. The fastest way to waste a year is to run hard in a slightly wrong direction. A few hours of honest reflection per quarter is the cheapest course correction available, and most people skip it because it doesn't feel like work.

When I look back at a year, I try to sort it into three honest buckets. What to keep: fewer yeses, better yeses. What to leave: over-identifying with the outcome. What I loved: the rhythm of my real life, the morning drop-offs, the ordinary days.

Build the pause in

You don't need a mountain or a sabbatical. You need a recurring appointment with yourself and the honesty to keep it.

This is the same belief that runs through OMC. We build from possibility, not fear, and you can't tell which one is driving you if you never slow down enough to look. The pause is where you catch the fear before it makes the decision for you.

Put the quarterly review on the calendar. Treat your one life with at least the strategic care you'd give a business. Your North Star is worth checking more than once a year.

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