Dinner at the boss’s


Ever wonder what your boss’s digs look like? I do. Not all the time though, that’d be a little weird and a whole lot of creepy.

But seriously, haven’t you ever wondered if your boss lives in a pimped-out mansion or a one-bedroom apartment with 18 kids and a pet rat named Christopher? More importantly, haven’t you ever wondered what your life would be like if you continued down the same road and became an exec like your boss, what your paycheck would be like (read: haven’t you ever wondered if you’re going to end up living in a cardboard box behind a dive bar in a cold, cold city where no one knows your name since salary is such a taboo topic and you’ll never really know if you’ve made it until… well, you make it?)?

I have and let me just say… this man does not live in a cardboard box. A few weeks ago, my boss (well, I guess we should call him “my old boss” after that 30 minute surprise earlier this month) invited the team to his digs in the heart of San Francisco for a team bonding session/last hurrah over dinner.

I thought, “Cool. This’ll be fun. Maybe I’ll bake some cookies or make a tiramisu for dessert.”

Silly me.

I’m not in college anymore. This isn’t a last-minute dorm room potluck where you  bring burnt Tollhouse cookies while your roommates run to Walgreens to pick up a few bottles of Coke and a bag of red Solo cups. This is a grown-up shindig with people over the age of 22. This is a classy, working-person’s dinner party.


This is a catered dinner party at $70 a pop (and expensed by the company). No burnt cookies required.


The food was phenomenal (just look at the pictures: slow-roasted tri-tip, white bean salad, mac & cheese, quiche and cheesecake with caramel sauce), the company was great and the main attraction (the house) was amazing. 

The house was deceptively huge. It never ended. There were stairs that went up, stairs that went down, rooms just for guests, playrooms just for the kids, a bedroom for the au-pair (yes, the au-pair!), closets for shoes, bathrooms and master bathrooms, a huge kitchen, a patio and a backyard… all in San Francisco. If Mary Poppins ever owned a house that matched her magical bag, this was it.

Like I said, I think it’s safe to say that old boss doesn’t live in a cardboard box behind a dive bar in the city.

I guess now all I need to do is go to an Ivy League grad school, work hard, kick ass, be brilliant and move up the corporate ladder at the speed of light.

No big, right?


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