Headed to Milwaukee + the pros and cons of moving a lot

Ashley and I recently counted up how many times we’ve moved since we started dating. The number stands at 12. Somehow, we’ve managed to move more than once per year.

Move number 13 is about to happen. Hopefully it will be the last one for a long while.

We got a house in the Bay View neighborhood in Milwaukee. It’s walkable and bikable. It’s close to parks, Lake Michigan, and some awesome restaurants. We’re excited!

Yes, there is a long winter. Thankfully, I have firmly and irrevocably convinced myself that the winters here are not that bad. They actually have a lot of positives. Think of the community building aspects of a long winter, people!

A friend told me it’s cool to tuck your pants into your socks these days. I’m still determining if I’m cool enough to pull it off.

As the latest move approaches, I’ve been reflecting on the pros and cons of moving all the time.

Pros of moving all the time:

Experiencing new areas like a local as opposed to dipping in and out for a vacation.
Friends and family get really excited when you tell them you’re moving nearby.
Spending quality time living close to far-flung friends and family members, meeting their new babies, etc.

Baby Charlie checking out the BK apartment, showing no fear

Always fun running hills and getting views in SF with Tim.

Learning about different cultures.
Driving moves are a great excuse to visit friends who live along the route.
Improving your spatial awareness skills by figuring out how to best pack your stuff into every nook and cranny of a car.

Moving back to Wisconsin. This was more stable than it looks.

Establishing a wide network of new friends, professional connections, and pickup basketball enthusiasts.

Amazing guys trip that I never would have found out about were it not for pickup hoops in Chicago.

Learning you have awesome friends and family who will let you crash with them while you find a place.

An air mattress at Ashley’s brother’s place in SF. The inimitable Oslo was our suite mate.

Crashing at Casa de Ross while apartment hunting in Chicago.

Providing joy to neighbors and local moms hustling on the Facebook marketplace when you firesale all your stuff on the cheap because oh crap the move out date is approaching really fast.
Experiencing Prospect Park in Brooklyn during morning off-leash dog hours — this should be a bucket list item for all dog owners.

Sweating it out with some incredibly kind Mormon missionaries who helped us lift heavy things when they saw us struggling to get up to our second floor place in Studio City, CA.
Learning that, with enough determination and layers, you can go for walks in Chicago when it’s -50F

Brave Ashley at Navy Pier in -50F. The city had to light the train tracks on fire it was so cold. That’s frozen Lake Michigan behind her.

Living in a fun, new place is a great excuse for people to visit

Me and the dogs got to crash girl’s weekend NYC

Shoutout to mom for visiting the frigid Sheboygan woods and for helping us get our first dog, Oscar.

Cons of moving all the time:

Friends and family get sad when you tell them you’re up and leaving. You have to have fun yet also bittersweet goodbye events.

One of many goodbye dinners we’ve had over the years. Love these people!

Moving all the time makes it impossible to get rooted. You’re less likely to get involved with making a place better. Sheboygan was the place we lived the longest, so it was the hardest to leave. I still miss the woods near our house.

You tend to invest less in relationships once you know you’re going to move :(
It’s expensive!
You might end up in an ancient Brooklyn apartment building below a unit the landlords have neglected to maintain. The pipes could burst above you just as you’re sitting down to dinner, causing it rain from the ceiling. When you call your superintendent to help you’ll get his voicemail. Firefighters have to get involved.

Ashley, calm under pressure, figuring it all out.

The actual act of moving can be physically and mentally draining.
You have to switch pickup basketball games and lose a lot of those relationships

My LA pickup game was a fun one, this was my final day.

Those nights when you first get to a place or have just sold all your stuff and you have to sleep in a sleeping bag on the floor are fun in theory, less so in practice.
Having to part with a dope array of house plants that your wife worked super hard to cultivate. It’s also tough to cut books, furniture, and vinyl records you like.

A very good use of my college basketball per diem money.

Getting angry emails from your landlord in Israel because you didn’t clean your apartment before moving out. Remembering the awful state you left it in and feeling embarrassed years later when you marry someone who shows you how actual adults thoroughly clean a place out when they leave.
Your Craigslist roommates in Los Angeles might get really mad over small details regarding your move out, for seemingly no reason. Though in retrospect it was probably a lot of repressed anger coming out because you stunk the place up by slow cooking beef liver in the apartment every weekend.

Marrying Milwaukee?

If all these moves have taught me anything, it’s that nowhere is perfect. It’s all about making tradeoffs that fit your lifestyle. We are happy with our current tradeoffs.

I recently read a thought provoking essay called Marry Your City. The idea is that, like with marriage, truly committing to a place through thick and thin makes for a more rewarding experience over time as opposed to living a more itinerant, rootless existence.

Many people have a fear of civic commitment that is pretty comparable to a fear of marriage, and it’s a problem for individuals and for cities.

These same people want to live in a place and consume it, but leave as soon as it becomes an imposition on them. They want to enjoy the fruits of someone else’s civic effort, but never apply their own. They want to retain optionality, and so forgo the real benefits of stable commitment.

But cities needed committed citizens to both reach their full potential, and to recover from devastation.

This is another section I liked:

Committing to where you live, with the same level of deliberation, seriousness, and wise constraint as a marriage, unlocks a whole host of good things.

You can more confidently put down roots, knowing that you will be around to nurture and grow them over the long term. This means investing in local groups and nearby schools, caring for the public domain, planting trees, and more. You can’t learn the best way to do these things until you’ve been around for a while, iterating over time.
Daniel Golliher, “Marry Your City”

I love the idea of putting down long term roots and being a more engaged member of my local community. Someone has to advocate for the maintenance of basketball courts before they are all swept away in a pickle ball induced mania.

That said, I can’t commit to marrying Milwaukee quite yet, as much as I want to. We’ve been excited about a lot places before, and yet we always move. But I feel on the cusp of getting engaged to Milwaukee, which is still something! At the very least we are marrying Wisconsin. These out of state moves have got to end.

I’m really hoping lucky move number 13 is the one that sticks. Judging by how much fun we’ve been having in Milwaukee this summer, things are off to a good start!