Chris Wiegman Chris Wiegman

Could this be failure?

It’s funny how quickly life can change sometimes.

A month ago we started the long process of the paperwork to move to Portugal.

Today we’re talking about moving back to Chicago, at least for a little while.

At one point, about 2-3 years ago I said that if I was still writing WordPress code in a year, after trying to move on to other projects for quite some time, I will have failed in my career. A year after that I was actually writing more WordPress code than when I said it and realized it was time to change things so I went back into management (back as in I did it before my development career, but had not since).

Long before that I said that if I ever lived in Chicago again I would consider that a personal failure yet, here we are. With luck it would be on our terms and we would move well into the city. It would also, we hope, only be for a few years as we simply want to be there for our parents while they’re still with us.

Ironically, perhaps, we moved to Florida as, at the time, both of our parents spent 6 months of the year there so it made a lot of sense to be closer to family then. Today that is no longer the case and we have grown to the point where we’re not just uncomfortable in Florida but I actively hate it.

On the other hand I so do miss a real city. We thought that would be what we got when we moved to Austin but it wasn’t. Austin turned out to be akin to a Chicago suburb like Naperville or Schaumburg that thought it was Chicago itself. I’ve never been comfortable in any suburb we’ve lived in and neither Austin nor Sarasota are exceptions.

I guess that’s not entirely true. Our one criteria in moving to Florida was a walking neighborhood and we bought our house sight-unseen to get that. For the first few years that was wonderful. Now I don’t feel safe going into any of the places we can walk to.

Chicago could be that walking neighborhood again, albeit with winter this time (something I look forward to but Joy dreads). We could use our time here to travel to Portugal and elsewhere a bit more and work on a permanent move when we’re ready. I like to think we could both be happy doing it that way.

I just can’t shake the fact that I always viewed living in Chicago as failure. I know it’s irrational but there were a lot of reasons for it and that, combined with a few other things, still has me wondering if this would be the right move or not.

Could Chicago be failure? I don’t know… but I think we may find out in the coming months.