GENERATIONAL TENSIONS

My Boomer Coworker Was A Complex Person

She was also a stark reminder to me that not every individual “represents” their generation as a whole

We’ve all seen people get insulted or disparaged because of their age. Whether it’s older people, younger people, or middle-aged people: Ageism is a multidirectional problem. And, unfortunately, it only appears to be intensifying with each new decade.

As an older Millennial of the “Xennial” microgeneration, I used to harbor a lot more sour sentiments toward older folks back when I was in my teens and twenties. Growing older myself, I’ve come to appreciate much of the wisdom and levity offered by Baby Boomers, Traditionalists (aka “The Silent Generation”), and GI-Gens (aka “The Greatest Generation”).

Not to mention guidance from GenXers — the younger half of whom, generationally speaking, I view as “big brothers” and “big sisters” of sorts.

But I also have always endured — and still continue to endure — my share of anti-youth ageism inflicted upon me by others. I realize that a lot of this is a by-product of stereotypes and prejudicial assumptions.

People don’t know what they don’t know. Until they finally realize where they’ve gone wrong, that is.

Yet, it’s still imperative that we don’t let any of it go unchecked. Prejudice morphing into casual bigotry morphing into actionable discrimination is what causes so many people to be mistreated in this world. It fuels anger, resentment, and toxicity.

As I look back on a short-lived experience with one of my former coworkers, Lillian — such a dynamic becomes much more crystallized, in my mind.

First Impressions

It was January of 2010. I was working as an assistant to an Independent Medicare Broker named Lloyd in Chatsworth, California. At this point, I’d only been Lloyd’s employee for a few months. But I was very quickly seeing firsthand what a miserable person he was.

During the first year I worked for Lloyd, he employed both me and a woman named Sarah out of his home office. Sarah was a plucky blonde British immigrant who had an agile sense of humor. She was a divorced mom to two teenaged girls, and her job under Lloyd’s employment was a part-time gig to supplement her income. Sarah’s regular day job was as a veterinary assistant in Studio City.

I, meanwhile, had been working half-days for Lloyd. That meant that I’d spent the most time on the phone, cold-calling potential clients and trying to get them to try out Lloyd’s governmentally-subsidized brokerage services (yes, I was one of those annoying telemarketers — except, unlike many of them, our product was legitimate).

For the first few months I’d worked there, Lloyd was very happy with my performance (and Sarah’s). Then, he decided he no longer wanted to pay for leads of upcoming Medicare recipients who’d filled out interest cards. Instead, apparently to save money, he decided to rely on a generic phone log containing the personal information of everyone in the Los Angeles area who was about to turn 65.

Thus, it was much harder for Sarah and myself to entice new clients on Lloyd’s behalf via telephone. But, since Lloyd had such a high opinion of himself and his own past record individually netting new clients, he suddenly seemed to feel we weren’t trying hard enough.

He wanted to make more money — which I could understand.

He felt the need to spend less time cold-calling strangers so he could keep better tabs on his wife, Judi, who was deteriorating quickly from Alzheimer’s Disease. I could also understand that.

So, one day when Lloyd drove to the bus stop to pick me up, I saw an older woman in the front seat of his car. He didn’t even formally introduce me to her, as I got into the backseat. Lloyd just started yammering about other things, as he drove us to his house.

This was Lillian. He’d hired her to share phone duties with me and Sarah — because, again, we apparently weren’t performing up to his lofty expectations.

As I would later learn, Lillian had recently acquired Lloyd as her own broker. A retiree who’d turned 65 just one year earlier, Lillian had approached Lloyd — on her own — asking him if he might have any part-time work for her.

Lillian was part of the “Silent Nester” microgeneration — people born on the cusp of the Traditionalist (“Silent Generation”) and Leaper (Baby Boomer) cohorts.

Over the next few days, Lillian and I chatted cordially. I made a conscious effort to be friendly and upbeat toward her. In this first week or two of being my coworker there, Lillian had displayed no initial signs that she’d come to be a problematic person.

That would soon change.

‘Boom’-ing Into Our Workplace

Little by little, I began to notice idiosyncrasies and underlying tensions amidst Lillian’s behavior.

Some were just minor annoyances — such as her tendency to hum the song “Sunshine Day” (from The Brady Bunch). Constantly!

There was the time Lillian had prepared Lloyd and Judi some lamb chops for dinner, which she’d brought for them from her home in some Tupperware. Despite her rice-based side dish appearing rather sloppy and unappetizing, I complimented Lillian on how thoughtful that was of her — and how amazing the meat cutlets looked.

“Oh, I love lamb chops!” I said, excitedly.

“Who said you could have any?” Judi ribbed me back, playfully — as she’d been like a surrogate Jewish grandmother to me before her Alzheimer’s got really bad.

Was Lillian simply trying to do something gracious for Judi and Lloyd? Or was she, in a very subtle way, trying to “outshine” me and Sarah?

Lillian and I even had some nice conversations about common ways in which we approached life. I was telling her, once, how I always made a regular trip to the grocery store on Thursdays or Fridays in anticipation for the weekend. She expressed how she did the exact same thing.

“That way, I’ll have everything I need for the weekend,” Lillian told me, affirming what I myself had just shared with her.

But then, her speech and interpersonal expectations became more overt.

Lillian might make a passing remark to me about “someone your age” (referring to our four-decade age difference). Or she’d crack rather low-hanging “jokes” about supposed generalized inadequacies of men.

Another time, as she was leaving: It was darker than usual, outside. She asked me, politely enough:

“Walk me out?”

I escorted Lillian to her car. At the time, I’d silently assumed it was just a strange request of entitlement on her part. I figured she expected to be treated with “chivalry” (a philosophy I reject) by me — due to me being much younger and a male person.

It wasn’t until years later when it occurred to me: Perhaps she was nervous about walking alone to her car, as a woman, after the sun had set? Even though it was only a few feet away from Lloyd’s front porch.

Or, she was worried about being spotted, as a Black person, walking alone in a predominantly-White suburban neighborhood? Lillian may have been nervous that a racist “Karen” or “Kyle” might approach her, demanding to know what “right” she had to be there.

So, when I accompanied her (even for a relatively short stroll), Lillian could have been securing her personal safety by relying on my white privilege and/or male privilege in that momentary scenario.

Crossed Signals

But what soon became very clear was that Lillian resented how Lloyd viewed me as the “lead agent” between her, Sarah, and myself.

As brokerage assistants, each of us was assigned a tickler file where we could store notes or follow-up reminders. At one point, I suggested to Lillian that she mark down the information of people who decline our offer so we could check back with them during the next Annual Enrollment Period (when all Medicare recipients have a window within which they can switch providers).

I made this suggestion because I’d witnessed Lillian crossing off names from the cold-call list after receiving a rejection from them.

“They’re gone. Out of my life!” she insisted, glibly.

This irked me, because I knew that Lloyd was paying good money for these leads (even as generic as they were). I didn’t want to see those resources go to waste. So, when I advised Lillian to jot down the phone numbers and file them away for the following year, she rebuffed my technique.

“You do it your way, I’ll do it mine,” she said, crisply.

On another occasion, when Lillian needed to check with Lloyd to make sure a time slot in his schedule was still open for meeting with a new potential client — she barged RIGHT INTO the bathroom, notebook in hand, while Lloyd was in there.

Sarah, who happened to be sitting next to me as we jointly observed Lillian do this, turned to me and silently mouthed the words:

“What? The? Fuck?”

For my part, I was simply flabbergasted and speechless that Lillian would do that. Fortunately, Lloyd must not have been in a compromising position, as we didn’t hear him yelling at Lillian.

There was usually no hesitation from Lloyd when someone sparked his short fuse. Such was the case during a training session, where Lloyd demonstrated phone techniques for me, Sarah, and Lillian while we all sat around his and Judi’s dining room table. At one point, Lloyd and Lillian got into an argument about a detail related to AARP (of which Lillian was a member).

Lloyd was never one to cave in when he felt confident he was right about something. I can’t remember the exact detail about which they disagreed, but I do remember that it turned out Lillian was right (which Lloyd discovered, later on).

But in that heated moment, Lloyd barked at her, irritated:

“No it doesn’t, Lillian!”

To which Lillian spat back, with sassy indignation:

“Yes it does, Lloyd!”

And she lilted his name with a hard-“L” from her tongue, audibly.

This exchange made it obvious to Sarah and myself that Lloyd was growing more and more fed up with Lillian as the weeks passed.

She “Takes Her Check and Leaves”

The last straw from both Lloyd and Lillian arrived when Lillian tried to throw me under the bus to him, in private.

It started one afternoon while Lloyd was out in the field. Sarah, Judi, Lillian, and myself were all gathered in Lloyd and Judi’s kitchen. We were helping Judi try to locate a utensil she needed for making a recipe.

Lillian looked in one cupboard and was able to find it for Judi. The spot to which the utensil had been relocated was obvious, in hindsight. I wished I’d thought of it.

“I might have looked there,” I said to Judi, giddily, “but I guess I was self-conscious that you might think I was snooping around your kitchen.”

This is why I’m not a stand-up comedian. I was trying to be lightly self-deprecating, poking fun at my own lack of foresight. But Lillian interpreted my comment as a personal attack on her, individually.

“I was trying to be helpful!” she insisted, defensively.

“Oh, you definitely were,” I tried to reassure her. “I just wish I’d thought resourcefully enough to look for it, there.”

“Then don’t be accusing people of snooping around in other people’s homes,” Lillian retorted, bitterly. And she flounced out of the room.

The next day, Lillian and I were in one of the offices while Lloyd was filling us in on the agenda for the next couple of days. He made it a point to tell us how much he appreciated our teamwork.

“I do my best,” said Lillian. And, with a side-glance at me, she added, “I just go out of my way to never make anything personal.”

“Well, I hope I’ve never come off as personally attacking anyone,” I said.

“Well, you do,” Lillian pouted at me.

Lloyd spoke up. “I’ve never seen Anthony do anything like that, either,” he gently told Lillian.

So I admitted to my poorly-conceived joking. I told Lloyd — in front of Lillian — about my botched attempt to be lighthearted, the previous day. How it seemed as though Lillian thought I was accusing her personally of “snooping”…even though that was the last thing I’d intended to suggest.

And, in front of Lloyd, I apologized to Lillian. I told her I felt bad if my words came off that way.

“Well, you just need to be careful what you say to people,” Lillian lectured me. She looked at Lloyd. “And Sarah agrees with me, on that!” she added.

Now I felt really awful that it appeared I’d hurt Lillian so deeply. And, on top of that, I was hearing that Sarah apparently shared Lillian’s discomfort with me.

Hours later, Lillian had just left for the day. Sarah arrived for her shift. As soon as Sarah arrived in the office, I began babbling…

“Sarah, I just want you to know that I’m truly sorry if my joking was inappropriate, yesterday. I never intended to offend anyone. I just felt slightly inadequate that I was having trouble helping Judi.”

With a blank stare, Sarah asked me, “Anthony, what are you talking about?”

Now I was the one taken aback. “Well, earlier, Lillian told Lloyd how hurt she was when I’d made that joke, the other day, about how I didn’t want to ‘snoop’ in their kitchen. She thought I was talking about her. And she told us that you agreed with her…”

Sarah’s jaw dropped. She looked as though she’d just been slapped across the face.

“I said NO SUCH THING!” she gaped, clearly gobsmacked at hearing how Lillian was trying to put words into her mouth.

“Oh. Well, she told me and Lloyd that you were just as offended by me as she was,” I explained, meekly.

An appalled gaze overtook Sarah’s face. “That liar!” she exclaimed, realizing what Lillian had been trying to do. “I never had any conversation like that with her! Anthony, I want you to know — I’ve never felt that way about you. How dare she pull me into her attempt to manipulate Lloyd!”

“Well, that’s what she said,” I shrugged. Now I was becoming pissed off at Lillian’s antics.

“That’s it. I want nothing more to do with that woman!” Sarah insisted. “I refuse to work any shifts with her, from now on! If there’s one thing I cannot tolerate, it’s people making up stories about me at my workplace!”

When Lloyd arrived home that evening, Sarah and I told him what Lillian had been saying.

The next day, we learned that Lillian would no longer be working with us.

According to Lloyd: That morning, he’d spoken with Lillian about her behavior. He’d told her that we all wanted her to be a part of our team — but things would need to change if she still wanted to work there. He demanded that she needed to have respect for both me and Sarah. He also made it clear he expected Lillian to take my advice more seriously.

“Well, maybe I should just take my last check, and go,” said Lillian, standoffish in the face of Lloyd confronting her.

“We want you here, Lillian,” he’d told us he’d reiterated to her.

“Maybe I should take my check and go,” she’d repeated.

So Lloyd wrote her out her final paycheck, and Lillian left.

By the time Lloyd relayed this account for Sarah and myself, it was done.

Introspection & Indignation

Lloyd later told me that he theorized Lillian had a chip on her shoulder because she probably resented “some young kid” (me!) — from her perspective — telling her what to do at her job.

I suspect Lloyd was onto something, there.

As the oldest of the Baby Boomer generation, Lillian possessed all of the silent rage that’s radiated by people who believe ageism can only work in one direction — emanating from younger people, directed against older people.

In this case, she probably already had me pegged as an Entitled Millennial White Guy who seemed (to her) to act like a know-it-all. The insinuation, here, was that I should be willing to absorb all of her “wisdom” like a sponge, based solely on her more extensive life experience.

She couldn’t fathom that maybe I’d developed some good ideas of my own. To Lillian, my communication style was microaggressive — reminding her of the racist and sexist behavior she’d undoubtedly confronted from others throughout her life.

Lillian had no way of knowing that a lot of my awkwardness could be attributed to the fact that I’m autistic. But, then again, autism wasn’t something that was talked about — or even considered, really — throughout the 1950s and 1960s.

Racial justice, yes.

Women’s suffrage, yes.

But any of Lillian’s involvement with the Civil Rights Movement was unlikely to have dealt pointedly with ableism (people with “hidden” disabilities) or genderism (sexual orientation or traditional gender roles).

In her mind, if there was going to be any ageism inflicted during our working relationship — it would be from me, toward her.

A young White arrogant whippersnapper attacking the wiser Black elder woman.

I believe that’s the narrative from which Lillian was operating. And some of it may have been valid.

Her experiences with misogyny and white supremacy made her inherently cautious and suspicious when around me. To a degree, I can sympathize with Lillian’s hesitance in that regard.

But she was cheating herself out of a potential genuine friendship by being unwilling to see past my birthyear and neurodivergence.

After Lillian quit, Lloyd told me she’d called me “a liar.” At one point, she’d complained how I never talked to her on nights when she drove me home. In reality, I had felt shy and skittish, not wanting to say “the wrong thing” to her (especially when she was being generous enough to give me a ride home). From my perspective, it felt as though Lillian wasn’t talking to me. I’d told Lloyd exactly that, in defense of myself.

When Lloyd brought that up to Lillian — that’s when she’d accused me of “lying.”

In reality, I suspect Lillian just thought it was stupid and lazy of me to have never learned how to drive — much the way my dad’s big sister, Eileen, seemed to insinuate when she’d visited our family, last autumn.

Then, Lloyd used the N-word to berate Lillian for trying to pit us all against one another (referring to her as a “dumb ******”). Of course, he never would have said that to Lillian’s face. But the fact that he had the gall to say that about her, once she’d quit, was appalling.

In hindsight, this experience taught me how it’s important to proactively express empathy while also standing up for oneself. It reminds me that I’m much better off without either Lillian or Lloyd in my life.

Age itself doesn’t necessarily equal wisdom.

And certainly not good judgment.

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