Story Time: Sometimes It Be That Way
A brutal lesson in ‘it’s not you, it's me' from that time I went on tour with Jewel.
And I'm sorry if my heart breaking ruined your day.
Oh well, sometimes it be that way.
- Jewel
I wasn’t always overweight. As a kid and teenager, I was more of a malnourished string bean—all elbows and knees with nothing to spare. Even now, if you examine my fluffiest parts (please don’t), you’ll notice my arms and legs are still slim. But in my mid-twenties, blockades of fat set up camp around my midsection, where they’ve been unlawfully squatting and taking over ever since.
Looking back at old photos, I’m struck by the irony: I spent years believing I was big and unattractive. But honestly? I was thin—and kind of cute! Yet the worse I thought I looked, the worse I treated myself, and the more weight I gained, creating a self-fulfilling prophecy. That toxic self-perception became the foundation for what has been a lifelong wrestling match with my weight.
For years, my ego—a masterful shame machine—has insisted that being fat has robbed me of opportunities, relationships, and far too much joy. While that narrative leans heavily on self-pity, there’s just enough truth to make it sting—especially in moments like fumbling with a seat belt extender on a plane or having to awkwardly dismount a roller coaster in front of a crowd because the harness refuses to click shut.
But few moments in my life left a scar quite like the time my insecurities about my weight turned a short tour with Alaskan poet and pop star Jewel into years of self-inflicted torment.
At the time, I’d just wrapped a TV show and, as is typical in Hollywood, found myself floundering between projects. I was desperately searching for work while spiraling with the eternal question, “What do I want to do with my life?”
One night, while sulking over my lack of direction and drowning my anxiety in Chinese takeout, I got an unexpected call from my friend David. He was at a noisy New York restaurant, working on a movie with director Brett Ratner.
“Are you still looking for work?” he asked.
“Yes, very much so,” I replied, trying not to sound too eager while dropping chow mein on my shirt.
“What do you think of Jewel?”
“The singer? I love her! Her Spirit album was part of the soundtrack that helped get me through the tumultuous months of filming Three Kings.”
“Great!” David said. “We’re here at dinner, and her assistant of 15 years is leaving and I’ve been singing your praises.”
Before I could even process the “we” he mentioned, a very familiar, childlike voice suddenly snatched the phone from him and began speaking excitedly.
“Hey, Bob! My assistant is leaving, and I have no idea what I’m going to do without him. But David swears you’re the perfect person to step in—he promised me you’re not a dud. Want to hit the road with me for a couple of days? We can sniff butts like horses and see if we like each other.”
Convinced I was being Punk’d, I tried to keep it together and answered, my voice only slightly overwhelmed, “I would love the opportunity! Just let me know when and where, and I’ll be there!”
Even 23 years later, two moments from that call are seared into my brain: “Don’t be a dud,” and how horses greet. I had to look up what she meant because, honestly, I wasn’t even sure I’d heard her correctly.
Turns out, horses have an incredible sense of smell. When they meet, they sniff each other until one asserts dominance—usually with a bite, a stomp, or a whinny. From what I’ve read, whichever demonstrates first tends to lock in that role for the rest of their relationship. Naturally, I overanalyzed it and couldn’t help but see the same dynamic in human relationships—but that’s a story for another day.
The next day, I got a call from her mom, Nedra, who was also running her company. She asked me a few general questions—mostly to make sure I wasn’t just some random fan who had infiltrated the inner circle—and confirmed my travel details. The plan was for me to spend a few days on the road with Jewel and her assistant to learn the lay of the land and, more accurately, sniff each other’s asses.
For the three days between that call and touching down in Indiana, I became a full-fledged Jewel aficionado. I listened to her albums on repeat, read her book of poetry, A Night Without Armor, and dove into her autobiographical short stories, Chasing Down the Dawn. Since the internet wasn’t the endless resource it is today, I had to work hard to cram as much Jewel knowledge as possible. The only other times in my life I’d studied this hard was for my high school economics final (to graduate) and when I got certified to teach aerobics.
The plan was for me to meet Jewel at her hotel when I arrived so we could ride to the venue together and get some quality face time. But thanks to a delayed flight, by the time I landed, she was already at the venue, on vocal rest, and still recovering from a broken collarbone.
Fortunately, her assistant was there to greet me, and he couldn’t have been kinder. He introduced me to the crew and gave me a backstage tour of the auditorium. He seemed almost as excited for me to be there as I was.
He admitted he’d been wanting to move on for a while but, out of love and loyalty to her, didn’t want to leave until he knew she had a solid replacement. Apparently, I was the first person they were both genuinely excited about. That was equal parts reassuring and unnerving—nothing creates performance anxiety quite like high expectations!
He also prepared me for meeting her, explaining that she could sometimes be “a bit like a cat” when meeting new people. I wanted to quip, “A cat? But I’ve spent the week preparing to meet a horse!”—but for once, I managed to keep my dumb jokes to myself. He continued, “Sometimes she’ll circle the room, sussing you out from a distance, and other times she’s all over you, on your lap like you’ve been best friends forever.” By the end of the trip, I understood exactly what he meant.
I met her briefly just before the show. She was gracious, kind, and eager to meet me. She couldn’t have been lovelier. When she learned I’d never seen her perform live, she immediately had them find me a seat in the audience so I could relax and enjoy the show.
It was her New Wild West Acoustic Tour, named after her song of the same name, and I was blown away. For two hours, she stood on stage with just her guitar and her arm in a sling, singing, yodeling, telling stories, and reinventing some of her most well-known songs. The audience was spellbound—you could hear a pin drop when she spoke. I was mesmerized and already pinching myself, imagining the new life I was about to step into.
After the show, I rode with her in the back of a van to the hotel. She was exhausted, and our interaction was brief. She decided it would be better if we rode together the next morning from Indiana to Kentucky for our official sniff test.
I spent the morning in my room preparing, but when I arrived in the lobby, her assistant informed me that she had some last-minute phone interviews to handle, and that we’d chat in her room once we got to the next hotel. I was a little disappointed—I’d already hyped myself up for the conversation—but I tried to be understanding.
I’ll take Big Boy Pants for $600, Alex!
Once we arrived in Kentucky, the assistant continued to take me under his wing as though I already had the job and showing me how things on the road were handled. He explained what would be expected of me, showed me how to work her humidifier, and gave me a crash course on how she liked her tea. He also reminded me, yet again, that she was really excited to have me there. But my confidence—what little I had—was quickly fading the longer it was taking for me to see her. As Brene Brown would say, “my never-good-enough shame gremlins” were wet, multiplying, and getting rowdy.
A new time was set to meet in her room, but just minutes before, I was informed that her touring band had flown in to surprise her and that our official sniff test was now moved to after the show. By now, my nervous system was short-circuiting. I’ve never been great at pumping myself up, and any enthusiasm I’d managed to muster for my two previous missed meet-ups had completely deflated. I’ll take a patch repair kit and air compressor for $300, Alex!
But then, without warning, I was told she wanted to talk to me in her dressing room while she got ready for the show. I had a feeling this was just to free up her evening for drinks with the band later, which suddenly made my presence feel like an inconvenience. But I reminded myself—I was here for a job, not a social call.
Still, I’ll take Confidence Destroyer for $800, Alex.
What came next was the ultimate boss move—and if it weren’t happening to me, I’d probably admire it. She sat with her back to me, facing the mirror, meticulously applying her makeup. Her questions were sharp and direct, her focus never breaking from her mascara and eye shadow. She rarely looked me in the eye, which only made the whole exchange feel even more like a calculated power play.
It’s worth noting that she’s stunning in person—captivating, even—but the lack of eye contact was a psychological mind game I was absolutely not prepared for.
Between questions, she spoke as if I already had the job, casually explaining the importance of her makeup brushes—a set gifted to her by the late, great Kevyn Aucoin, who had recently passed away. It was almost disarming—until she suddenly pivoted with a barrage of intimidating questions:
“What makes you think you could handle working with me?”
“Why do you think you’re up for the task?”
“Do you think you could keep up with me?”
“Why should I hire you?”
I was already off my game when I arrived, and the more she questioned me, the more I questioned myself. Who did I think I was, believing I could handle working for her? Suddenly, I was my teenage self, an outcast completely out of my depth. Running the life of an acclaimed pop star? Yeah, right.
All my preparation and goodwill? Gone. I stumbled over my words. I floundered. And for some reason, I kept bringing up my budding friendship with Lance Bass, as if knowing a boy band member somehow proved I belonged in her world and could be trusted around celebrities. Judging by her reaction—or lack thereof—she couldn’t have cared less.
She had undeniably bitten, stomped, and whinnied first, and I was ready to be sent out to pasture. Maybe my ass smelled? I still don’t know how this horse-sniffing metaphor works.
I’ll take the nerves of Peter Brady’s puberty voice for $1,000, Alex.
Our conversation lasted all of 20 minutes. She wrapped it up by saying we’d grab a drink after the show to finish our chat because she wanted to learn more about me.
By the time we met up after, her bandmates were in tow, her interest in me seemed to have faded, and I had officially run out of *NSYNC stories. As her assistant had warned, she bounced from lap to lap among her friends like a cat. I’m not sure she ever sat on her own cushion all night. She was comfortable, happy, and completely at ease—a rare and lovely glimpse into her personal world.
Her bandmates were sweet, but I couldn’t shake the feeling that one of these things was not like the others—and that thing was me. With so many personalities and conversations swirling around, she never really got the chance to learn more about me.
I was convinced I hadn’t lived up to the hype and that she would report back to David that I was, in fact, a dud.
I went to bed feeling defeated, convinced everything about our meeting had gone horribly wrong. So you can imagine my shock when I met her assistant in the lobby the next morning—and he was practically giddy.
“She really liked you!” he said. “She’s ready for you to do a trial run with her.”
Record scratch. What? How? Was she in the same interviews I was? Did I just win Jeopardy! by betting everything but my last dollar while everyone got the answer wrong?
He explained that I should head home, pack, and get my passport ready. Jewel had a few dates left on the tour before heading to London for a few weeks to work with Robbie Williams’ producer, Guy Chambers, on her next album—and she wanted me to go with her (for yet another round of ass-sniffing).
He was confident she’d made up her mind and that London was just a formality. I, on the other hand, was a mix of befuddled and excited as I headed back to Los Angeles.
Over the next week, her business manager and I emailed back and forth about my salary and my plans to relocate to San Diego, where she lived. My head was spinning with dreams of this new chapter. I was about to make more money than ever before, and I couldn’t stop fantasizing about what my new unexpected life in San Diego would look like.
As the dates for the London trip drew closer (we were supposed to travel between Thanksgiving and Christmas), the response time from her business manager became noticeably slower. The messaging shifted from “The job is yours to lose” to “We’ll need to get back to you.” Then, just a few days before I was supposed to leave for London, I received an email saying that Jewel had decided to go to London alone, “but not to worry, they planned to bring me on fresh at the beginning of the year when she gets back.”
I was disappointed but still optimistic. It made sense—we were deep in the holidays, and the timing felt right for a fresh start in January. I was sad to miss London but relieved to keep my Christmas plans intact.
Then, while in Monterey with my family over Christmas, I received the final email from her business manager. It was short and unusually impersonal compared to our previous correspondence:
“Jewel has decided to go in a different direction and doesn’t feel she needs an assistant at this time. She wants to finish work on her new album, and depending on your availability, we will circle back with you in the future if anything changes.”
I was crushed. The gremlins in my mind whispered in unison, “Of course she needs an assistant, Jewel doesn’t feel like she needs you at this time.” The wind was completely knocked out of my sails.
My ego, ever eager to drag me down a dark alley, piled on fast. I spiraled through my worst doubts and insecurities, replaying a highlight reel of every reason I’d failed. Being my own worst critic, I fixated on every dumb thing I’d said, berating myself for not having better answers.
Even worse, I couldn’t shake the nagging realization that I wasn’t competing against anyone else for the job—this was all mine to lose. I’d already started looking for places to live in San Diego, imagining my new life and the adventure ahead. In just two sentences, my entire future felt upended.
Then came the thought that delivered the final blow: I lost out because of my weight. Her question, “Do you think you could keep up with me?” played on an endless loop. To me, her unspoken answer was obvious: no, because if I couldn’t take care of myself, how could I take care of her?
There’s a stigma that overweight people are lazy and unmotivated. For years, I let my insecurities convince me that’s all anyone sees: someone who doesn’t care about themselves—so why would they believe I’d care about the job? Ironically, those same insecurities drove me to work twice as hard to prove I’m not lazy or incapable once I have the gig. But in interviews, I stammer, feel unworthy, and default to self-deprecation.
Usually, my ace in the hole is my personality. But with Jewel, I felt like I never got the chance to show it. I was sure she judged me without ever opening the book. It was the cruelest explanation—and the only one I could allow myself to believe for many years and haunted me in every job interview and honestly some dates I had over the following decade.
Some might wonder, “If this has plagued you for so long, why not just lose the weight?” To that, I always say: If it were that simple, I promise you, I would have done it by now.
I always point to Oprah Winfrey—someone who has struggled with her weight more publicly than anyone else and has access to every resource imaginable. If sheer willpower and resources were the answer, she could hire someone to follow her around and slap food out of her hand. And yet, she still struggles—just like the rest of us, because it just isn’t that simple.
In 2006, I took on a VP of Operations role at a production company, with the promise of a big raise if we hit specific goals. We not only hit them—we exceeded them. Two months later, when my raise still hadn’t come through, I finally worked up the nerve to ask the CFO about it. His response?
"Well, it doesn’t look like you’re starving."
He was fired for that comment—but not before trying to take us to court, where I had to testify that, yes, he had actually said that. Somewhere in a Los Angeles courthouse, there are official documents notarizing my fat shame as part of my career.
That experience sent me spiraling, replaying the same brutal tape in my head—validating what I had long suspected: “It’s obvious why Jewel didn’t hire you. I wouldn’t have either. You’re a slob who doesn’t deserve a seat at the table.” The great reminder that no one speaks to you as horrifically as you speak to yourself.
But then, in 2015, something unexpected happened. While listening to Howard Stern interview Jewel about her new memoir, she shared a story about how her mother had embezzled all of her money and swindled her out of her fortune.
I immediately drove to Barnes & Noble to pick up a copy of the book. Sure enough, as she tells the story, learning about her mother’s betrayal all unfolds while she’s preparing to record 0304 in London—the exact time I had been waiting to start the job.
It had nothing to do with me. Not a thing.
Hiring me had been the furthest thing from her mind. It wasn’t about my weight, my Lance Bass stories, my perceived inadequacies, or the idea that I was a dud. The email from her business manager had been short because they were in survival mode, and I had probably followed up one too many times. Jewel wasn’t judging me—she was buried under an avalanche of betrayal and chaos.
It was humbling to realize, years later, that I hadn’t even been a blip on her radar. And yet, I had let that experience define me—shaping how I carried myself, how hard I worked, and where I overcompensated.
Why? Because for all that time, what other choice did I have but to make it about me?
Insecurity has always hit me hardest in my career. Without a college degree, I constantly felt inadequate and overcompensated to prove I belonged. My weight wasn’t just a number or how my jeans fit—it carried emotional heaviness, too.
Dating in West Hollywood in the ’90s felt like being a cat staring longingly into a fish tank. I refused to bring that same energy into my career, so I made sure to show up, exert myself, get everything done, and be loved in the process. It was exhausting—but it worked. I’ve had a very good career.
I just wish I’d been kinder to myself along the way. That I’d allowed myself to enjoy the ride a little more. And that I could give my younger self the grace I’ve since learned to live with.
And the greatest takeaway from my brief fling with Jewel? It’s like going on a couple of great dates, sniffing each other’s asses, and just when you think things are going well—they ghost you. You’re left agonizing over what you could have possibly done wrong.
And oftentimes, the answer is simple: It has nothing to do with you. Sometimes it just be that way.
I love you and your stories. Keep 'em coming!!! What a great reminder to be kinder to ourselves and each other but I will admit that after reading the news this week about Jewel, I'm having a hard time not saying something snarky and rude about her. 🤪
Another touching story by Bob! Thank you so much for sharing so freely about your life experiences. Truly inspiring and there is no doubt hearing your stories will help people.