Lessons in Progress: What I’ve Learned So Far as an Executor

By Jason R. Roske
Owner, KC Auction & Appraisal Company

When you step into the role of executor, it’s not just a title—it’s like adding a part-time job to your full-time life.

It’s a job that shows up in your inbox, your weekends, your evenings, and your thoughts. Some days, it feels manageable. Other days, it’s overwhelming. And through it all, there’s no one path, no checklist that works perfectly. You have to move forward with imperfect information and make the best decision you can in each moment.

In this post, I’m stepping back to share what I’ve learned so far—not as a legal guide, but as someone living it, one choice at a time.

Momentum Creates Momentum

One of the biggest lessons has been the value of movement. Once you start ticking items off the list, even small ones, it creates energy for the next step. Progress isn’t passive—it demands motion.

This past weekend, Stacey and I tackled the yardwork and deep cleaning at the main estate house ourselves. We could have hired someone, but we decided to keep the momentum going.

Clearing fallen branches, hauling them to the Missouri Organic Yard Waste Recycling center (a fantastic Jackson County, Missouri resource with free Saturday drop-offs), mowing the long-neglected lawn, scrubbing the kitchen and bathrooms—each task made the house feel a little less heavy, a little more alive.

When we finished, driving up to the house didn’t feel sad or daunting anymore. It felt like progress—a home beginning to transition to its next chapter.

Everything is Negotiable—And It Should Be

Another critical lesson: don’t accept every number at face value.

From real estate commissions to utility bills, negotiation isn’t only allowed—it’s often expected.

When listing the second property, the buyer’s agent only charged a 1% commission, which significantly improved the estate’s net proceeds.
On the main house, one agent offered a reduced commission of 2% instead of the traditional 3%—saving thousands for the estate.
After a toilet at the second house ran non-stop for a week and triggered a massive water bill, I called the city and calmly explained the situation. By identifying myself as the executor and noting that the house was vacant, the water department immediately offered to file a leak adjustment claim.

Even unexpected moments—like the discovery of termites at the second house—were a negotiation opportunity. I chose to treat the home right away, despite its “as-is” status. The pest company even agreed to bill us at closing rather than asking for immediate payment. In the end, the buyers made no further repair requests. Whether that was because we addressed the termites early or not, I’ll never know—but it felt like the right decision to protect the estate.

Lesson learned: Everything—from agent commissions to pest control to utility bills—is negotiable when you’re representing an estate. You just have to ask.

Choosing How to Spend Time, Money, and Energy

Managing an estate forces you to constantly weigh time vs. money vs. energy.

We chose to do the yard work ourselves. The money we “earned” by doing it—what we would have paid contractors—was still meaningful, even at our personal hourly rates.

But more importantly, it gave us emotional benefits:

Seeing the home regain dignity with our own hands
Maintaining momentum instead of getting bogged down in scheduling contractors
Feeling personally connected to the work we were doing for the estate

There’s great satisfaction in watching a property shift from neglected to show-worthy because of your direct effort. That was worth far more than the dollars saved.

Still, I recognize that not every project should be DIY. Sometimes, spending money to protect your energy and focus is the smarter choice. Part of the job is knowing which is which—and forgiving yourself when you get it wrong.

The Emotional Toll of Emptiness

After the estate sale and the first deep cleaning, walking through the main house hit me harder than I expected.

The furnishings were gone. The pictures, paintings, and artifacts that once made it a home were stripped away. What was left was harder to see: deferred maintenance, stains, nicotine residue, dirt tucked into forgotten corners.

It’s one thing to sort through memories. It’s another to walk through an empty shell of a life you knew so well.

Emptiness reveals truths you didn’t notice before. Some you expect. Some you don’t. And all of them are part of saying goodbye.

Ongoing Progress and Closing the Second House

There’s good news, too. Regular progress is being made. The second house is under contract and moving steadily toward closing.

That progress—however incremental—helps me stay grounded. It reminds me that even though the process feels endless some days, we are moving forward. The hard work, the decisions, the attention to detail—it’s all building toward resolution.

Responsibility Beyond Payment

One of the biggest internal shifts I’ve noticed is how differently I think about every decision now.

Being an executor isn’t just about finishing tasks. It’s about caring for the financial health of the estate—as if it were your own.

Yes, I’ll be compensated for my work as executor. But that’s not what drives me. I feel a true fiduciary responsibility—to honor my friend’s trust, to manage the estate’s resources wisely, and to protect the bottom line even when it might be easier to let something slide.

It’s the same approach I bring to KC Auction & Appraisal Company. Every auction we manage, every client we represent—I don’t just think about what benefits me. I think about what best serves the client, even if it means a little less in my own pocket.

When you’re entrusted with someone else’s legacy, you owe them more than just effort. You owe them stewardship.

The Unexpected Impact

One of the most humbling parts of this journey has been the responses from others.

People are reading these posts. They’re reaching out. They’re telling me that what I’m writing resonates with their own experiences—grief, loss, estate management, unexpected responsibility.

Just this morning, I received a text from a friend and beneficiary of the estate:

“Hi Jason, I want to tell you how comforting your blog has been. My cousin just passed away unexpectedly, and I have been in CA with her adult kids dealing with grief and paperwork and preparations. Never easy.”

It’s a reminder that while this has often felt isolating, none of us are truly alone in this.

Looking Ahead

There’s still a lot left to do—preparing the main house for listing, final distributions, endless paperwork—but today, it feels a little lighter. A little clearer.

If you’re walking this path too: trust your instincts, ask for help when you need it, and remember that forward motion—even small steps—matters more than you realize.

Next up:
In the coming posts, I’ll talk about preparing the main home for sale—and what it feels like to finally let go.