Reflection can certainly be a good thing, but it can also become obsessive if you spend too much time on it. So here are some thoughts if you find yourself spiraling into endless reflection. I try to tell myself these things to mixed results.
Timebox It
As Parkinson's Law notes, "work expands to fill the time available," likewise reflecting on the year's events could take a whole year to process, particularly if you are like me and think about the same pieces over and over again. Set a block of time around the activity and try to limit yourself to that box. If you find yourself daydreaming into the joys of last summer or why you didn't get your TPS report turned in on time that once, remind yourself that there is a time and place to be going through and processing the year. Once your time is up, wrap up the activity.
You can only learn so much looking backwards. You need to look forwards and sideways as well. So if you spend more than, say, four hours reviewing the previous year (and I mean your activities, not your accounting), you are probably in overkill land. Start with a one or two hour limit and go from there, but try to knock it out in one sitting. You don't want to leave some of the items unresolved to tempt you to daydream and work on (repeatedly) in between sessions.
Put an Objective On It
Why are you doing this? To improve yourself? Set a concrete goal for what you want to accomplish by reviewing the year and you can make it more productive. Maybe you want to generate an action plan to address a specific skill gap in the new year. Perhaps you want to sit down and benchmark progress against your goals and year-over-year improvement in various areas (this is what I will do in my year in review post coming soon). Whatever the reason, setting a specific reason for the activity helps focus on a goal instead of random reflection and wandering.
Future-Test It
Pro-tip: You are not going to relive last March 12. Or May 19, June 28, or October 1st either. So the only point of thinking of things that happened on those days is to improve yourself moving forward. Ask yourself, "will this help me be or do better next year?" and if not, move on to something else. Spending excessive time on history without a forward-looking approach to it will just frustrate you and waste time. Spin everything towards future goals as opposed to maintaining a backwards-focus and you can leverage those memories for your own benefit.
Forget About It
At some point, you're just wasting time. Stop what you're doing and start making future plans. Knock something off your to do list. Build something. Write something. Or go spend some quality time with your family. Whatever it is, doing things now are more important than reviewing the past for inordinate amounts of time. Enjoy yourself. Accomplish something. It is never too late to start on that.
Conclusion
Reflecting on your year (or even farther back) is fine and natural at this point of the year, but if you put a goal around it like any sort of productivity exercise, you can limit its ability to be destructive or counterproductive. I hope you have a happy holiday season and I'll catch you soon for the year in review.
