Should I Stay or Should I Go?

By Micah Rosenbloom

As we approach the end of COVID, many who experimented with life in the Hudson Valley or Tahoe, or those new urbanists who flocked to cities like Miami or Austin, or back home to the midwest, will have some decisions to make.

Primarily, should I stay or should I go?

Over my professional career, I’ve moved from LA > Boston > NYC > SF > NYC and brought a family along on several of those journeys. Recently some friends have asked for my POV/tips on relocation, and I thought they might be useful to a wider audience.

If you’re “testing” a new city, prepare to fail. Go in with the intent to stay. People want to know that you’re there for the long haul and are reluctant to build real relationships if you signal a short-term mindset.

The 1st year is new and exciting — a bit of a honeymoon phase.

The 2nd is the homesick phase, where you start comparing everything to “back home.”

The 3rd is sort of when you figure out if the new place is your “forever home.”

Join FB groups/forums and talk to people who have moved to your target locale. Also, spend time in the place, walking around neighborhoods. Don’t be shy — talk to people! A couple of conversations will tell you more than hours on Zillow!

I recently moved 7 blocks in NYC, and despite being less than a mile away, there are many differences. Renting gives you time to do real reconnaissance.

Florida winters are amazing, as is September in the Catskills. But living a full year in a place is a sum of all the good and bad of the seasons, including ice storms, hurricanes, and the disruptions they cause — caveat emptor.

Facetime with managers, coffees with peers, and other F2F contact is essential, especially early in one’s career. Is trading this access for better amenities the right tradeoff at this moment?

There’s a lot of buzz re: “the future of work,” and some big companies are testing it out, but don’t be surprised if the conventional wisdom boomerangs at some companies.

Tell them why you’re thinking of moving. Be mindful of how they’ll receive time zone issues, their perception of your new locale, etc.

Moving is going to make your tax situation more complex. It’s likely nothing you can’t handle, but you might want to budget a bit extra to account for having “nexus” in two or more states.

We can all learn and grow as individuals and professionals by experiencing new geographies. Our new reality has afforded many knowledge workers a new level of geographic freedom. Take advantage, but do it with eyes wide open!

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