When the End Feels Heavier Than the Beginning

By Jason R. Roske

It has been a while since I last wrote an update in this series. Since then, we’ve gone from planning the Celebration of Life to actually holding it, resolved the lawsuit, and uncovered a few new hurdles that reminded me just how unpredictable this role can be.

At the beginning of the process, I thought the hardest work would come early: organizing paperwork, making big decisions, selling property, and getting the estate moving in the right direction. Now that the estate is nearly complete, I expected to feel lighter. Instead, I find myself learning that the end carries its own kind of weight.

Part of me simply wants this process to be finished. It reminds me of when Stacey was pregnant with Will — the excitement and anticipation were real, but by eight and a half months we were both just ready for him to arrive. That’s how this feels now. I’m grateful to have carried the responsibility, but I’m also just ready for it to be done.

The Celebration of Life

We held the Celebration of Life at Grand Street Café, one of his favorite places. The setting was perfect: elegant but comfortable, with food that sparked conversations and laughter at the tables. Sharing a meal together felt fitting, because so much of his life was about bringing people together across different worlds.

What struck me most was the range of people who came. His bridge partners. Colleagues from the antiques community. Friends from his years in the hairdressing world. Family. Supporters of the organizations he cared about, including the Heartland Men’s Chorus and KC Pet Project.

Representatives from both organizations spoke. Their remarks were heartfelt but also revealing. Heartland, being a gay men’s chorus, spoke about the ongoing struggles they face in today’s political climate. For some in the audience, those words resonated deeply. For others, particularly his more conservative friends, the response was rolling eyes and quiet comments.

It wasn’t surprising. It reminded me how unusual his life really was. Because he worked for himself, he was never confined to one professional or social circle. His friendships stretched across divides. Political, cultural, and generational. That was one of his gifts. And it showed at the Celebration of Life. For a few hours, people who might never sit in the same room otherwise shared a table, a story, and a plate of food.

Small Things That Add Up

Being an executor is full of lessons you don’t expect. Some are big and dramatic. Others are small, but they pile up in ways that matter.

One example: the estate account. I assumed I’d be able to get a debit card tied to the account for day-to-day expenses. That would have made it simple to cover costs directly on behalf of the estate without carrying checks everywhere. But the bank told me they don’t issue debit cards for estate accounts. They explained that some attorneys object to the practice, so as a blanket rule, it’s not allowed.

That left me with two choices: either keep a checkbook with me at all times or pay out of pocket for certain expenses and request reimbursement. I chose the latter, since carrying checks around wasn’t practical. It wasn’t a hardship, but it was another example of how the simplest things can become unnecessarily complicated.

It’s one more reminder for anyone stepping into this role: don’t assume even the basic financial tools will work the way you expect.

The Lawsuit

The lawsuit that arose earlier in the process has now been settled. I’m grateful for that, though it left a bad taste.

The issue itself was frustrating enough. A contract signed with his conservator before he died, which became void upon his passing. We went another direction for liquidation, and the company involved chose to file suit for damages. What made it even more uncomfortable was that those same people also turned out to be beneficiaries of the estate.

It wasn’t more complicated, legally speaking, but it was certainly messier. “Icky” might be the best word for it.

The good news is that it’s resolved. But the lesson for me is that executors can’t always count on goodwill, even when they expect it. Sometimes doing what seems legally correct and straightforward still lands you in conflict.

Delays and Frustrations

Not everything has moved smoothly since then. Some tasks that I thought would be simple have stretched on far longer than expected.

Arranging for his burial with his parents has been difficult. I’ve had a hard time reaching the cemetery, and progress has been slower than I imagined. The monument company is also taking much longer than I would have believed. What I thought might take weeks has stretched into months, with little clarity on when it will be finished.

If he were my family, I think this would feel different. It might already be done, simply because the urgency would be personal. But as an executor, it feels more like a task than a calling. I care about seeing it through, yet I also don’t carry the same weight of obligation that his family might. That’s a strange place to sit. Caring deeply and not caring in the same breath. It’s similar to the Celebration of Life. I wanted it to go well, and I’m glad it did, but it was also one more responsibility to complete.

And then there are the attorney delays. Early in the process, the attorneys were given a full packet of documents, including a list of debts and bills. For reasons I don’t understand, several creditors were never contacted. Seven months later, notices of death are just now being sent out with timelines for submitting claims.

That means closing the estate will be pushed back yet again, at least another month, and with it comes additional attorney fees and costs. It is disappointing, and it underscores the theme that keeps running through this experience: everything takes longer than you expect.

“Nothing is as great, or as terrible, as it seems in the moment.”

I remind myself of this often. The tasks that feel endless now will eventually resolve. But in the thick of it, time feels distorted.

The Tax Question

Another wrinkle has come up involving taxes. His life partner, Christy, passed away last year. As part of that, he inherited a 401(k). He chose to take the full distribution. Now that amount is being treated as income instead of an inheritance.

I don’t know why, and I need to clarify it with the attorney. It’s a significant sum, and if it truly counts as income, the estate owes tax on it. But it feels like it should be handled as an inheritance, not income. For now, it’s an unresolved question, and one more layer of complexity in a process already full of them.

Closing Thought

At this stage, I thought things would be winding down. Instead, I’m reminded again and again that nothing about being an executor is straightforward. Each time I cross something off the list, another detail surfaces.

What I didn’t anticipate are the tears that come at unexpected moments. They don’t show up when I’m buried in paperwork or on the phone with attorneys. They appear when I least expect them.

Like when I reviewed the draft of the final settlement and realized we are actually close to the end.

Like at the Celebration of Life, when a beautiful bouquet of flowers was delivered to the café. We already had flowers at the event, but something about that thoughtful arrangement arriving struck a chord.

And especially when I stood up to thank people for their support. I managed to get through most of the room, but when I turned to thank Stacey for everything she has carried with me through this process, that’s when my voice broke.

Those are the moments that remind me this isn’t just paperwork, contracts, or checklists. It’s the work of love, loss, and legacy.

The Celebration of Life offered comfort. The lawsuit is behind us. But delays, bills, and tax questions are still in front of me. This role continues to stretch longer and weigh heavier than I expected — even as the end comes into view.

Next in the Series

In the next post, I’ll share what it feels like to carry this role when it refuses to end neatly, and why executors often find that the final stretch is the hardest one of all.