There’s Always Something: Progress, Setbacks, and Strange Emotions in the Executor Journey
By Jason R. Roske
Owner, KC Auction & Appraisal Company
There’s always something. That phrase has become my quiet mantra as I move through the role of executor—equal parts observation, warning, and acceptance.
Just when I think a task is complete, another issue pops up. Just when things feel like they’re settling, a deadline shifts or a document gets delayed. And even the big, seemingly satisfying moments—closing on a property, launching an auction—are often accompanied by unexpected emotion, bureaucracy, or plain old exhaustion.
Being the executor of a friend’s estate is one of the most complex roles I’ve ever taken on. It’s not just about getting things done. It’s about making decisions, fielding questions, adapting to surprises, and carrying forward someone else’s life and wishes with care—even when the process doesn’t seem to care much about you.
Here’s a look at where things stand right now.
The Second House: Almost Closed—But Not Quite
After weeks of effort, I signed the seller’s side of the paperwork for the second house on Wednesday. The buyers were ready, everything was lined up… and then, nothing.
It’s now Friday afternoon, and the sale still hasn’t closed or funded. Not because of anything the buyers did, but because the underwriter raised last-minute questions about the HOA’s master policy. They’ve had a month to ask these questions, and they wait until the buyers are at the table to ask them.
Even if those get resolved soon, we’ve now missed the 3 p.m. wire transfer deadline. So the earliest the funding could happen is Monday. Until then, it’s just… stuck.
And that brings a whole new set of worries.
If the delay stretches too far, will we have to redo documents that are already signed? Will settlement figures change, throwing off final calculations or taxes? Could utility prorations become a problem if we slip into another billing cycle?
I’ve sold real estate before, and I know how fast things can get complicated when the timeline shifts. That’s what keeps replaying in the back of my mind: we were ready. The buyers were ready. But until it funds, none of that counts.
Everyone wants it to be done—the agents want their commissions, the buyers want their new home, and I want to close a door to a chapter in this journey—but for now, it’s one more thing on hold.
We’ll see what next week brings.
The Truist Saga: A Masterclass in Bureaucracy
If you’ve been following along, you already know I’ve been trying to work with Truist Bank to manage the mortgage on the second house. And when I say “work with,” I mean I’ve been chasing them, emailing them, calling them—for over a month—with almost no response.
Let me be clear: they’ve never once initiated contact with me. Not a phone call. Not a helpful email. Only form letters about the account being in default, despite the fact that I sent them a full set of documents—including two death certificates, the will, letters testamentary, and the non-probate transfer of the home.
Now, weeks later, they’ve told me I need to submit two more notarized forms before they can authorize access. Meanwhile, the title company for the closing was able to get the exact payoff amount and escrow figures—information I still haven’t been allowed to see.
They won’t even update who the escrow check is made out to, or where it’s sent, until I jump through the next round of hoops.
And just to put the cherry on top: today, I saw that Truist is hosting a professional golf tournament—the Truist Championship. Rory McIlroy won the event last year.
I had never even heard of Truist before this experience. They don’t have a single branch in Kansas City. And yet, somehow, they’ve become a central fixture in my life as an executor.
Funny how that works. Or doesn’t.
The Main House: Listed and Looking Good
The primary house officially hit the MLS this morning.
I’ve been mowing like crazy the past few weeks—rain or shine—to keep the curb appeal fresh and welcoming. The grass has been growing faster than the snow fell this winter, and that’s saying something. I want the house to look its best because I know first impressions matter.
The “Coming Soon” listing generated early buzz, and now that it’s live, I’m hopeful we’ll see showings pick up quickly. Maybe even a bidding war this weekend if things go well.
Getting this house to market feels like progress I can actually see. And it helps make the day-to-day work feel like it’s adding up to something.
The Estate Auction: More Than a Catalog
This week, I also launched the online auction for the personal property from the estate.
Normally, writing auction descriptions is a routine part of my work. But this time, it wasn’t just about categories or dollar values. This was a reflection of my friend’s life—his decades of buying, selling, collecting, and curating.
As I scrolled through the photos and wrote about the items, I could see his story. His taste, his eccentricity, his passion. Each object had a connection, a moment, a meaning.
It made me pause. And it reminded me that this work isn’t just about liquidation. It’s about translation—turning a life into something others can see, appreciate, and carry forward.
When Loss Meets Anger
While reviewing photos for the auction, I came across a picture of my friend from an event last year. He was wearing his gold bracelet, a diamond ring, and a nice watch—all of which are now gone.
Not lost. Not misplaced. Stolen.
By people who knew him. People who had access while he was still alive.
It was a gut punch.
I’ve tried to approach this process with patience and professionalism. But that moment hit hard. There’s a deep sense of violation in knowing that someone took advantage of him, and that there’s no way to undo it now.
Let this serve as a warning: If you’re caring for someone nearing the end of life—or handling their estate—document the valuables early. Don’t assume everyone around them has good intentions. Be proactive. Be cautious. The regret of discovering theft after the fact doesn’t come with a fix.
The Recognition I Didn’t Expect
Something unexpected has happened over the past few weeks. People have started asking me about the executor process.
Some are just beginning their own journey. Others have been through it before. A few are watching from the sidelines, curious about what really happens behind the scenes.
They’ve shared stories, asked questions, and even thanked me for writing about all of this. It’s been a surprising and humbling experience.
And honestly, it’s one of the reasons I started documenting this journey in the first place. Most people only go through this role once in their lives. If my experience can help them feel less overwhelmed—or less alone—then this effort is worth it.
There’s Still a Lot to Do
One property is nearly sold. The other is on the market. The auction is live.
But there’s still plenty of work ahead—more paperwork, more communication, and almost certainly, more surprises.
Still, this week feels like a turning point. And even if no one throws a celebration or pours a toast, I know we’re getting closer to the finish line.
