1. What do you love about your job? Life gets so busy that it's easy to forget the answer to this question -- if there is one. If you do love your job, why? Could you love it more? Might you be able to spend more of your time on the work that's rewarding, less time on the stuff you hate? It's easy to get stuck in the rut where you think nothing can change, so what would happen if you stopped accepting some of the grunt work?
2. What do you hate about your job? Do you really need to do all the work you dislike, or has it become so routine that you (and your boss) have never questioned it? What would happen if you stopped doing it? Are you controlling this work or is it controlling you? I used to be maniacal about tracking business expenses; now I just look at the bottom line. Unless something is seriously wrong, I only need the summary, not the details.
3. What's next? Most people want to feel that they are growing, developing expertise, insight or experience. If you aren't, then you're stuck, and within the next year it's likely you'll get angry and frustrated. I recognize that this sounds like a horoscope, but every person I've ever interviewed who has changed jobs has commented that they should have done so earlier. They started looking only after they became fed up, and then the search proved agonizingly slow. Sometimes looking for a new position operates as a salutary reminder of what you like about the current one. Looking doesn't hurt, but getting stuck does.
4. What will you get better at? Even in the same job, there are skills and talents you can hone, either through external training, working with a mentor or by getting stretch assignments. So what do you want to do better? If the answer to that question is "nothing," then it's definitely time for a change! Some goals are endless; I'm the most organized person I know but I'd still like to be more systematic, less chaotic. I got better this year at building buffer time into my schedule -- time to recover from travel or to prepare for trips. But I'd still like a bedroom that wasn't littered with suitcases waiting to be unpacked.
5. What will you try for the first time? As much as I seek to be organized, I'm also conscious that you can be so organized that you never see or feel or do anything new. You know what works and you stick to it. But it's good for your brain and for your resilience to try something completely uncharacteristic - to (metaphorically) throw yourself off a cliff.
Last year, needing to do some research in Finland, instead of checking into a hotel I rented a room with a couple I'd never met. I figured I learn more if I met more people. For a seasoned hotel dweller, this felt positively dangerous, but I learned more with my hosts in a few days than I could have in a week of hotels.
You will probably have your own way of reviewing your working life, and most people like to complete the process by setting themselves goals and targets. My own experience is that, while those help, the review alone will re-orient your mind and your attitude. Maybe that's really what Labor Day is for.