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New Try to avoid reading in the subtext
When I read the exchange I just see a boss who is willing to cut you whatever slack you need, but also is feeling swamped. I wouldn't read anything negative into that.

However I would take that as an indication that you need to have effective backup. Give some careful thought to who you can bring up to speed on various parts of your job so that if the company was unexpectedly left without you, they would not be paralyzed. This will both leave you more able to take guilt-free vacations, and also be in a position to move onto any interesting projects that happen to come up.

Cheers,
Ben
"good ideas and bad code build communities, the other three combinations do not"
- [link|http://archives.real-time.com/pipermail/cocoon-devel/2000-October/003023.html|Stefano Mazzocchi]
New Seconded.
Get a backup. If not, either you'll feel too guilty to take a vacation, or you may have vacation requests denied.

Of course, you're boss should realize your value, and (in addition to paying you for it) ensure that there is always adequate coverage. Sometimes it takes a "disaster" to enlighten the boss.

Discuss it with the boss and see what happens. Becoming invaluable to the company never guarantees job security, just slavery.
[link|mailto:jbrabeck@attbi.com|Joe]
New And also ...
Give some careful thought to who you can bring up to speed on various parts of your job so that if the company was unexpectedly left without you, they would not be paralyzed.
As some wise[1] man once said:
Never become indispensible. They won't want to promote you and have to replace you.



[1] Cynical
===

Implicitly condoning stupidity since 2001.
     Boss wants me to work too damn much. - (inthane-chan) - (14)
         Heh.. not particularly perceptive kinda droid. - (Ashton)
         Dickensian - (rcareaga) - (7)
             Whoops, clarification. - (inthane-chan) - (1)
                 Forget what I said, then-- - (rcareaga)
             Time to make you envious - (pwhysall) - (4)
                 Re: Time to make you envious - (pwhysall) - (3)
                     Sounds like I'm somewhere in the middle. - (static)
                     Can I kick yer pasty British butt? ;) -NT - (inthane-chan) - (1)
                         Well, as for my part... Naah, what the heck. - (CRConrad)
         Try to avoid reading in the subtext - (ben_tilly) - (2)
             Seconded. - (jbrabeck)
             And also ... - (drewk)
         Re: Boss wants me to work too damn much. - (deSitter)
         Re: Boss wants me to work too damn much. - (rickw)

Non-migratory, just like coconuts.
42 ms