Trying to figure me out

[haha]

These guys are all clones, it's sad.

You say that because you do not really know them and don't want to know them. They likely return the feeling.

But Yalies are no more clones than Poles or Czechs are. Outsiders often feel superior, but may not be.

Ha

 

[plex]

I'm a bit younger (it is probably going to take me just as long though, if not longer, I probably have more debt because of professional school), and have dealt with the same exact sort of issues. The culture at my last workplace was a bit more inclined towards saving rather than spending...they ran regularly instead of going to the bars, which is another way to relieve some of the high stress of heavy work hours. When they asked about finances, since they all seemed to be fairly well balanced, I was just honest about it, and showed them a retirement prediction spreadsheet I use, though I waited awhile to feel them out before I did that. One of them really likes talking about the economy, so it is one of the main things we talk about.

From the boss discussion, he was probably trying to get to know you or size you up for sure. Either way, you just have to try to keep the conversation friendly by talking about his past. The pointed questions are really hard to avoid, so you just have to answer them and move on. Whatever you do, just keep concentrating on keeping the job, it's fun planning things out, but it is really secondary to improving your income. That is something I keep trying to get myself to work on as well, since I plan things out way too far ahead sometimes.

 

[freebird5825]

Now, something VERY interesting happened a while back. I was at lunch with my manager, who is also a friend. During our meal, he eventually asked about a property I purchased in a subtle way. We began talking about it, but I kept it vague as he began asking some financial questions. He's a smart guy and he pieced my finances together together in his mind from our conversation, also given that I don't spend like colleagues and splurge like others in the office - he turned away staring into space and said 'that's a lot of money.' Very awkward, yet, I looked him directly into the eyes and said 'it is.'

Friendliness or fishing expedition?
Either way, I think you handled it just fine.
My 2 cents...Manager or friend or both, he should not be asking you detailed financial questions unless you two are going to be formal partners in a business. It is rude to do that in any culture.
I have been on the receiving end of this type of inquisition myself, but for a different reason. It had to do with life insurance amounts.
My usual response was something along the lines of "It makes me very uncomfortable to discuss my personal finances.
I was raised not to talk about money in public." All BS of course, but the inquisitor didn't know that.
All I know is it short circuited the nosy questions every time.
I call this being creative, some would call it lying. Just as long as I was consistent with my answers, and polite but sparing with my words, it worked.