Moving cross-country is an unusual experience often preceded, in my experience, by a certain measure of regret.

I’ve done this three times, for varying values of “cross” country. After college, in upstate New York, I moved to Washington, DC. After 7 years there, my then-wife and I moved to Denver. We only stayed for 8 months, then moved to Chicago. We’ve since split, and now, after three and a half years here, I’m headed to Seattle.

I’ve learned something from all of these moves, but looking back on it now, I’ve mostly learned the same lesson multiple times.

As we prepared to move to Denver, I learned not to take my own city for granted. From the time we learned that Denver was a possibility to the moment we got keys to an apartment there, less than two months passed. In those two months, we scrambled to see the sights we hadn’t, to see the friends with whom we’d been losing touch, and to re-visit favorite restaurants.

I took full advantage of Denver, in part because I had just learned the importance of doing so, and in part because we knew we might only be there for about six months. That possibility came to be, so I’m thankful that I had the good sense to get out of the house nearly every weekend we were there, to explore hiking trails and breweries and winding mountain roads.

I swore I wouldn’t make the mistake again, and moved to Chicago with a list of recommendations from friends, just as I had in Denver. I swore that I would stick to the list, and make sure that I saw and did and experienced this city. I planned to be here longer than six months, but still, I didn’t want to have the experience I had in DC, where I realize that I’ve been somewhere for years and still hadn’t touched major areas and attractions of the city.

And yet, here I am. I have three more days left in Chicago, and once again, I am regretting my failure to fully experience this city in the past three years.

Don’t get me wrong, I’ve done a lot here. My list of recommendations from friends took me to a lot of interesting places, though many that I probably would have found on my own. It also included a lot of places that, if I’m being perfectly honest with myself, were probably never going to see my face walk through the door, simply because they weren’t my kind of places—though one could argue that I’ve just offered a perfectly good reason for why I certainly should have visited those places. But I digress.

I drove back to my apartment tonight after dropping our dog off with my ex for the last time, and realized how much of this city I still haven’t seen much. We are creatures of habit, and I more than most. I rarely make it up to the north neighborhoods, and have seen precious little of the enormous south side of the city. I’ve been to our beaches maybe three times, and I’m not sure I can name more than once that I’ve been in any of our parks (though I did make good use of the Lakefront Trail with my bike). I’ve been to a public library here exactly once.

Half of me wants to stop being negative, and remember all the things I did do—all the nights spent with friends at the homebrew club, all the pizzerias and bars and breweries that I did check out, all the bands I saw play live.

The other half wants to wallow in this regret and hold the lesson close, lest I forget it again.