If you're looking for a more interesting question to ask when catching up with someone other than "What's new?" or "What have you been up to?" then ask this one:
What has been the dominant theme of your conversations lately?
No, it's not quick or sexy, but it's important and very telling. For me, I've had a lot of conversations with people lately about their career plans, school plans, or life plans. They want to chat about whether they're making the right decision, how to not make a wrong decision, or they wonder if it's worth making a decision at all.
Some wonder if more school or the next job is the right decision. They're curious if they're stagnating where they are, left to flounder at a dead end job or in a master's program that may be no better than their undergrad one. They're curious if the opportunity cost is worth it, if they should be doing something else to get where they want to be.
I tell them not to worry about any of that and I instead ask if their life has a trajectory. To me, instead of planning out each step, it's better to know if your life is headed in a general direction (and what that direction is). It's the difference between a compass and a map.
A map plans out each step. Turn by turn directions will get you from point A to point B without missing a beat. No sightseeing. No pitstops. Go. Stop. Repeat.
A compass points you in the right direction (west), but doesn't tell you how to get there. It keeps you on track and you can check it when you think you may have gone off course. You have freedom to explore so as long as you are moving forward.
A plane from Nashville to Tulsa can get there a thousand different ways. The pilot is able to change altitudes to find smoother air or she can fly around a storm if need be. The plane is still getting to Tulsa.
You're the pilot of your life. Just know where you're headed and you can make all of the other decisions much more easily. Is grad school or a certain job right for you? It depends on where you want to end up. Define your trajectory and you'll be sure to choose wisely.
PS: I use this same compass/map analogy in my next book, due out in November. 50 Things Your Life Doesn't Need will help you to discover your life's passion and get rid of everything that stands in the way of it.