The Emotional Rollercoaster of Selling Your First Home

When the realtor emailed to tell us we received our first offer on our condo, I cried. And not because I was happy (though I was). I cried because it was the first time it really sank in that Illinois was no longer "home," and that our beloved space would soon be occupied by someone else.

After I posted my moving vlog, someone left a comment saying that I seemed very sad, and they hoped that there was something for me to look forward to in Portland. I was sort of taken aback, for Portland was something we’d dreamed about and talked about ad nauseam for years. But that doesn’t erase the history we have in Illinois, the place we spent the vast majority of our lives thus far, the place where we created a home together filled with countless memories and stories. New beginnings, even the happiest ones, are not possible without the end of something else, so of course I was going to be sad. The more places I go and experience and love, the more places I leave little pieces of my heart behind.

Almost as soon as I came to accept that the condo would soon be someone else’s, that first offer on the condo fell through due to the buyer’s financing. And then I was sad (and stressed) for an entirely different reason.

But within two days we had a second offer. There were less emotions the second time around—perhaps because I’d started to learn that the process of selling real estate is uncertain and complicated and NOT EASY, and I wasn’t going to allow myself feel excited until the deal was set in stone.

And I basically held my breath for the entire month of the closing process. At one point, we were sure the deal was going to fall through. Even our lawyer and realtor were breaking out the nails for the coffin. Basically, the buyer’s inspector had given him incorrect information about electrical codes, and the buyer was demanding that we do a complete re-wiring of the unit and threatening to break the contract over it. Which is ridiculous, because 1) the whole building is wired the same way—and had never had an issue, and 2) the inspector had used building codes that didn’t apply to our pre-1970s building. Luckily we had a great team working for us and our lawyer fought back hard to make the buyer understand that his demands were completely out of line. And he eventually cooled his jets, and the condo closed on October 29th after a few days of Mark dealing with hundreds of emails and overnighting paperwork from Oregon to Illinois.

Oh, and wire-transferring a decent chunk of money to our bank. Because, yes, we had to pay our bank in order to “sell” our condo.

(Caution: You’re now entering the mildly bitter portion of my emotional rollercoaster of selling our first home.)



We purchased our condo in April of 2008, at 25 and 26 years old (five months before our wedding), after years of hearing from older, well-meaning relatives that renting is “throwing money away” (I’d now like to send those relatives an invoice for the money we paid the bank, tbh). We thought it was smart, we thought we were being responsible and “adult” in settling down for a while. We thought prices from the housing bubble had come down.

And then fall of 2008 happened. It’s a classic tale of bad timing. The financial crisis and subsequent recession took the value of our $147,000 condo and stomped on it. At the lowest point—I want to say it was somewhere in 2010 or 2011—it wasn’t even hitting $95,000 according to Zillow. In that time we both lost our jobs in the building industry (but, luckily, not at the same time). Whereas we’d originally planned on being in the condo for 4-5 years and then think about moving west, we could only focus on present circumstances and hope that the value of our condo would rise again someday.

And it did—slowly, but not entirely. Our sale price was much less than what we bought it for, and effectively turned all those mortgage payments into rent. Mark did the math, and what we paid over 7+ years in the condo equated to about $600/month in rent—which is probably close to half the typical rent for 2BR units in Oak Park. It could have been a lot worse though, like it has been for many other people. So I guess there’s one silver lining. {Correction: Apparently I don't listen when it comes to math/numbers, because Mark has corrected me and told me that the $$$ we lost ends up more than average rents in Oak Park. Numbers are confusing.}

I’m being too harsh because the honest truth is we LOVED our condo and LOVED living in Oak Park (again let me refer you to my moving vlog and my #caitiwalksoakpark hashtag). It was home. In the weeks leading up to our move to Portland, I wished so many times that I could pick up the entire town and just make it a new neighborhood of Portland. Being an owner came with its own benefits as well—mainly the lack of a landlord to be accountable to and the ability to make the space truly yours (except for doormats; upon moving in we were quickly emailed by the condo association and told that doormats were strictly VERBOTEN and a fire hazard. Insert eyeroll emoji).



However, seven years of ownership has been a learning experience. I can fairly confidently say that I will never again buy a condo as a real estate investment. Maybe we’ll live in a condo later in life when downsizing as empty nesters or retirees, but the next place we purchase will be a home and will be someplace we intend to stay indefinitely. If and when we have children heading out on their own, I will not demonize renting as “throwing money away,” but as an option that allows you freedom and flexibility before you’re ready to commit to somewhere for the long haul. I’m not convinced of the idea of real estate as a worthy investment, particularly in the form of a condo. Not in the world I came of age in.

Another lesson has been to have so much more compassion for all parties involved in a real estate transaction. I've witnessed so many friends who are first-time homebuyers complain about sellers being such assholes for turning down offers and not coming down enough on their sale price. If those sellers are anything like us, sometimes you CAN'T go any lower without being underwater. Not everyone is trying to make a profit off of you; some people are just trying to make a hit hurt less. You have no idea what someone else's story is.

But we are onto a new chapter now. We are condo-free and mortgage-free, having returned to life as renters in Portland. I’m not sure what our future in real estate holds, particularly in this area. The Portland housing market is insane, with average housing prices around $350k+ for a small (and often less than pristine condition) bungalow. We’re still being told by relatives to keep our eyes open for good real estate deals to jump on, but honestly, that’s the farthest thing from my mind. $350k is well out of our range anyways, and we have to re-build our entire down payment after not making it back in the condo sale.

For now, the flexibility to choose a place to live within walking distance to downtown, to explore different neighborhoods, and to not be tied to any one location is worth being a renter to me. I no longer look at it as throwing money away but buying freedom. I think attitudes towards owning real estate have grown more skeptical among young people who experienced the recession—or it has just become a completely unachievable goal for many in our current world—but Mark and I had to live it to learn it.