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Sep 13 / Brian Grey

Eastbound and Back Around in 24 Hours!

One of the dynamics — among many — that come with working in a start-up environment is that you have to hustle, you have to be willing to operate with a sense of urgency that doesn’t typically exist when you’re working in a bigger company environment.  Now that said, let me say that you can take that mentality sometimes a bit too far — like when you hop on a plane in San Francisco on a Tuesday late afternoon, fly to New York, do a day of meetings on Wednesday, and then fly home that same Wednesday night.

Sometimes though you have to make trips like this.  So if you have to undertake this kind of gauntlet, here are a couple tips:

1) Eat and drink enough on the way out to NY so that you can avoid the lure of the “Open 24 Hours” Manhattan diner you walk to at 1:30 am where you down a milkshake that you justify drinking just because you order a vegetarian pasta dish (that’s of course loaded with some kind of cooking oil).  The benefit here is not just caloric.  Avoiding the diner lets you get an extra hour or two of sleep when you get to town which you will sorely need.

2) Schedule three, maybe four meetings — not five.  Given the logistics of getting around the City by taxi, the waiting time for meetings to start, the normal “how was your summer” chit chat, etc., when you get down to it, the human brain may only really have the capacity to focus on a couple meetings, especially when you’re working on three hours of sleep.

3) Set up a car service to get you to JFK for your flight back — don’t try to figure out for the first time how to navigate the NYC subway system to get from lower Manhattan to the airport.  This sounds like a great idea until you realize that JFK is like way far out in Queens and having to connect three times on “locals” means you’ve got a high probability of missing your flight.

4) Don’t make a trip like this in the middle of the week — all it does is mess up the rest of your week because you’ve basically just lost about a night’s worth of sleep.  Then again, if you like that “burning eyes” sensation in your late Friday afternoon meetings then maybe this mid-week New York trip is for you?

5) Be sure you travel with at least one if not two work colleagues so you can laugh and commiserate with them about how the idea of a trip like this sounded so much better the week before when it was being planned.

Actually, it’s trips like these that make for the lasting memories of trying to build something great as a start- up company.  But next time I can skip the milkshake — maybe!