My Lease Is Up. Here's What I'm Actually Doing.

By Jay Kimbol · October 28, 2025 · More posts

I'm writing this from a furnished one-bedroom apartment in Indianapolis. Mass Ave, on the third floor, with a window that faces a brick wall about fifteen feet away and a radiator that turns on around 6am with a sound I am still adjusting to. I moved here on October 11. My Chicago apartment is sublet through January 31. After that, I either come home or I don't.

This is not the answer I expected to land on when I started writing about all this in June.

For anyone arriving fresh: I'm a remote IT support worker, $71k a year, living in Chicago for the last six years. My landlord raised my rent 22% in May. I started running cost-of-living math on every Midwest city with a pulse. I went to Austin for a long weekend in July to look at apartments and ended up writing a long post about Barton Springs and the heat. I wrote three more posts after that. Six months of spreadsheets and second-guessing. My friends got tired of hearing about it. My girlfriend, Diana, became a kind of involuntary expert in the cost-of-living index of cities she had no interest in moving to.

The lease was up September 30. I had to do something.

What I expected, somewhere in the back of my head, was that I'd either sign a new Chicago lease and admit defeat, or I'd commit to Austin and start the process of actually moving. Those were the two options I'd been treating as the binary the whole time. The math said Austin made sense. The emotional math said Chicago. Pick one.

What I actually did, and the part I'm still slightly embarrassed about, is I asked my employer if I could work remotely from somewhere else for a few months. Not to relocate, exactly. To trial it. To live in another city for a finite amount of time and find out what I don't know.

They said yes faster than I expected. My manager, who is one of those people who makes a decision in roughly three seconds and is usually right about it, said: "Sure. Just don't be in a different time zone." I'd been planning to negotiate. I had three counterarguments prepared. I didn't get to use any of them.

So in late August I started looking for a furnished short-term rental, and the question became which city. Austin was the obvious answer because I'd been writing about it for months. But Austin is also expensive enough that a three-month trial would have cost me thousands more than I'd save. The math on Austin only works at the long-term lease price. Short-term furnished in Austin runs $2,400+ a month. That's worse than my Chicago rent.

I started looking at the cities I'd written about in that post about the surprises. Cincinnati was tempting but I'd never been. Pittsburgh I'd been to once, briefly, and it rained the whole time. Memphis I want to visit but didn't feel ready to commit three months to without a scouting trip first. Indianapolis was the one that kept making sense the more I looked. Furnished apartments on Mass Ave or in Fountain Square were going for $1,650 to $1,850 a month, all-in including utilities and internet. I could keep my Chicago apartment under sublease (which I had to negotiate separately, and which is its own story I'll spare you), so my actual monthly housing cost during the trial would be about a $500/month premium over staying put, all things considered. Less than I'd been spending on the long weekend trips and "research" food I'd been claiming as part of this whole project.

The other thing about Indianapolis: it's a four-hour drive from Chicago. If something blew up — if I hated it, if Diana hated it, if I needed to be home for a weekend — I could get back. The Austin version of this trial would have required flights. That distance reset the calculus.

So I drove down on October 11 in a U-Haul I didn't need (one suitcase, my work laptop, my work monitor, a pillow I'm strangely attached to). I'd booked the apartment site-unseen because the photos looked fine and I didn't have time to do another scouting trip. I want to report that the apartment is fine. The radiator is loud. The kitchen is small. The neighborhood is more walkable than I expected and considerably more compact than Chicago, which feels small at first and then comfortable in a way I can't fully explain.

It's been seventeen days. I'm going to say things now that may not be true in three months. That's the entire point of doing this rather than committing.

What I've noticed so far that the spreadsheet didn't tell me:

The first week, I felt great. Everything was new. I walked everywhere. I ate at three different breakfast places I would now recommend to anyone. I sat in a coffee shop on Mass Ave for an entire Saturday afternoon and worked through my book backlog and felt like a person who had figured something out.

The second week, I had a pretty bad day where everything was just slightly the wrong shape. The grocery store I'd picked is fine but it isn't the Jewel I know. The bus map doesn't match the geography I have in my head. There's a guy at the coffee shop who's there every day at the same time as me, and we've achieved a kind of nodding equilibrium that wouldn't have been weird in Chicago because in Chicago it would have been three people I knew, layered, instead of one stranger I see daily. I missed Logan Square so hard for about a day and a half that I almost called Diana to come pick me up. Then I made spaghetti and watched a baseball game and got over it.

What I think I'm finding out, tentatively: it's not that Indianapolis is bad. It's not even that I miss Chicago, exactly. It's that I miss the specific ambient density of the friendships and routines I've built over six years, and that's a thing that doesn't transfer with a sublease. The people I count as my actual friends — the three of them I mentioned in the Austin post — aren't here. They're four hours away, and I love them, and four hours is far enough that I'm not going to see them this weekend or next.

This is, I want to be honest, an obvious thing that I should have known before I drove down here. The COL index does not include "the cumulative weight of friendships you have built over six years." It does not have a column for "the small reassuring routines that make a city feel like home rather than a place you are in." If it did, those numbers would dwarf rent, dwarf taxes, dwarf everything else.

I am also, strangely, finding that the math part — which was the entire reason I started this — is the part I now think about least. Money is real. The thousand-dollars-a-month difference is real. But it turns out it's not the variable I'm actually optimizing for, when I look up from the spreadsheet and notice what I'm doing with my evenings.

So here's where I am right now, with three months and a few days left on the trial.

I think I will probably go back to Chicago. I'm not sure. Diana is fine with either outcome but she's articulated, gently, that the friends thing is real and the cost of rebuilding a social life from zero in your mid-thirties is not a cost the calculator captures. I think she's right.

I think the value of this trial is going to turn out to be that I now have a clearer sense of what I'd be giving up if I left, and that sense is going to make signing a Chicago lease feel less like defeat. I'd been treating "stay" as the cowardly choice. After two and a half weeks here, "stay" doesn't feel cowardly. It feels like a thing I'd be choosing, with reasons.

The financial math will adjust. I've started a separate savings account specifically for housing. I'm putting $300 a month into it, which won't make me rich but is a meaningful change from the zero I was saving in 2024. The Chicago lease I'd be signing in February would be in a different neighborhood — Avondale or maybe Lincoln Square — for about $400/month less than my Logan Square place. That's $4,800 a year I wouldn't be saving by staying in Logan Square out of inertia. The trial taught me that I'm willing to move within Chicago even if I'm not willing to leave. That's a real result.

I want to be careful not to make this sound tidier than it is. I might love Indianapolis by January. I might decide the friends thing is solvable and fly home for one weekend a month and call that the deal. I might find that I've been romanticizing Chicago because I'm new in Indianapolis and homesickness is doing the thinking. There are versions of the next two months where I end up with the opposite conclusion from the one I just wrote, and I want that on the record now so future me can read it and not pretend they always knew.

What I think the broader lesson is, and the reason I keep writing about all this: the math is real. I want to repeat that. The math is real. What the math doesn't tell you is everything that doesn't go in a column. And the only honest way to find out which of those things matter is to actually live in the alternative city for long enough to feel them. Three months, maybe. Six months would be better. A vacation isn't enough.

If you're staring down the same kind of decision — lease ending, math saying go, gut saying stay — I'd say try a trial. Negotiate it with your employer if you can. Sublease your place if you have one. Rent furnished short-term in the city you're considering. Live there for a season, with the laundry and the bad days and the random Tuesday nights, and find out what your gut has been trying to tell you that the spreadsheet kept overruling.

It's not going to give you a clean answer. It's going to give you a more honest one. Those aren't the same thing. The clean answer is the one I started this looking for. The honest one is the one I'm probably going to land on.

I'll write again in February with what I decided.

Jay Kimbol is somewhere in Indianapolis right now, probably at a coffee shop on Mass Ave, doing his actual job and pretending he's not also writing this. The next post comes whenever he figures out what's next, no earlier.