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Dear Employee #4,
I think no. Unless the two of you work so well together that it's actually pure fun.
I realize this brings up a whole host of issues about who should take the job and why, but I think it's a risk if you both do. What happens if you don't perform well? What if he feels he needs to fire you? What if he's crazy jealous of the guy who always flirts with you at the office? I think it's too much overlap.
Plus, think of all those hours you will be putting in. You'll be working together around the clock in a very stressful environment where people can be very cranky and high strung. I think the situation is a set-up for little tiffs and ill feelings. I can imagine lots of arguments and tantrums brewing.
In Silicon Valley you can surely find another start up that would meet your needs and interests. As I understand it, there is an enormous people shortage and start ups are just dying to hire people. If I were you, I'd find another opportunity, and then be sure to carve out some time to spend with your boyfriend outside of work.
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Dear Employee #4,
I say take it. I think the advantages outweigh the negatives. You'll get to know him better. You'll find out how much time you can really spend with each other before popping hives. You'll keep him on an even shorter leash.
There's more. Your lives can become more efficient. You can exchange feedback over coffee and the Sunday paper. No more wasted time asking him how his day went. You can brainstorm while having sex, especially if you keep a white board above the bed. Conferences and retreats would double as vacations. Since you already spend all day with him, your nights and weekends will free up and you can see all those neglected friends again.
...And if it all fails, I'm sure you're both smart enough to figure out if that really means the merger should be put off.
Or are you?
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May 8, 2000