How a Wendy’s Frosty Melted My Misconceptions About Guilt and Shame
I used to think guilt was useless. Then a 12-hour road trip and a Wendy’s Frosty changed everything.
Driving is like mental fasting — it clears my thoughts and makes room for inspiration. Last week, I hit the road on a 12-hour journey to Cleveland for a real estate mastermind reunion, not realizing I was also embarking on a profound exploration of my long-held beliefs.
The Seeds of Doubt
As the miles rolled by, my mind wandered to a concept I’d long clung to but was beginning to question: the idea that “guilt is a worthless emotion.” In my younger years, influenced by Buddhist teachings about attachment and living in the present, I’d dismissed guilt as a useless relic of the past. But was I missing something crucial?
A Cinematic Revelation
Little did I know, this road trip would challenge everything I thought I understood about guilt, shame, and the path to true empathy.”
As I neared Chicago, a conversation from an Apple TV crime drama began replaying itself in my mind. In “Presumed Innocent,” Jake Gyllenhaal’s character, Rusty Sabich, is a former attorney (and borderline psychopath) on trial for the murder of an ex-lover. At one point in the show, his old boss, a former district attorney now representing Sabich, makes a poignant statement:
“You know, in 40 years, I have seen a lot of guilt & shame in this business. Shame is something that you put on yourself. It’s self-absorbed, self-centered. Guilt is more about owning and feeling the pain you cause others. I don’t doubt that you feel shame.”
These words echoed in my mind, challenging my long-held beliefs about guilt and shame. Could there be value in guilt that I’d been overlooking?
The Frosty Awakening
After a pleasant evening catching up with friends, I offered a ride back to the hotel to a friend who had flown in from Chicago. He is an identical twin, originally from Pakistan, but he’s spent much of his life in America. He was hungry, it was late, and practically nothing was open, so he asked me to pull into Wendy’s.
While I wasn’t particularly craving fast food, my friend’s hospitality and generosity (like many Muslim families) is legendary, and this was no different. For the second time that evening, he showed me kindness by offering to buy me dinner.
“Sure,” I chimed in. “I’ll have a Frosty.”
“What’s a Frosty?” he asked.
“Get out of here,” I replied, astonished. “Are you serious? You’ve really never heard of a Frosty?”
“I wasn’t born here!” he protested with a broad smile.
“Dude, you’ve lived here for more than twenty years.” I shook my head in disbelief. “You can’t play that card anymore.”
“So what is it?” he asked again, still laughing.
“It’s like a shake — more like a chocolate malt. All the real Wendy’s connoisseurs dip their French fries in the Frosty. It’s the basis of all fast food in America: salty, sweet, fatty.”
“Oh! My wife’s been trying to get me to try ice cream and French fries. This must be what she’s talking about.”
This comment brought the car to a screeching halt. I turned to face him. “Wait — your pregnant wife has been asking you to try this and you haven’t? You’re not even a little curious why she might like it?”
“No,” he replied, completely unaware of how casually dismissive he sounded.
“Dude, you’re about to have a child. And you don’t care why your wife likes things? What about your kid? If you don’t develop empathy, like yesterday, your family is facing some serious problems.”
In that moment, I saw a mirror of my past self — someone so caught up in their own world that they couldn’t see the simple desires and needs of their partner. This wasn’t just about a Frosty; it was about the myriad small ways we can be blind to the experiences of those closest to us.
The Mirror of Empathy
As we pulled out of the drive-thru (he loved Frosties and French fries, by the way), my friend described a narcissistic business partner who drove him crazy. He detailed the challenges of working with someone manipulative, only focused on their own interests and desires. He wasn’t making the connection to his own life.
“I heard a saying the other day,” I told him. “Be thankful for your triggers, for they reveal where you are not free.” I eased the car into an empty space in front of the hotel and shifted into park. “Your narcissistic friend is like a funhouse mirror — reflecting your own lack of empathy back at you in an exaggerated way.”
The Bell Curve of Emotions
“Our emotions exist on a bell curve,” I continued. “Depending on our circumstances, awareness and stage in life, they can swing to extremes. Your business partner is a cautionary tale, showing you what happens when empathy is absent in relationships. This can happen when we spend too much time in our head and too little in our hearts. Heads are notoriously lacking in empathy where our hearts feel others’ lived experiences. Life was giving you a chance to feel that.”
The Narcissism Connection
My mind flashed back to Gyllenhaal’s character. By some estimates, 1% of the world’s population — almost 80 million people — may have conditions such as Narcissistic Personality Disorder, Antisocial Personality Disorder, or psychopathy. These disorders are all associated with a lack of empathy, which made me start to wonder:
“Had my own ego, much like the narcissism I saw in others, kept me from feeling empathy and guilt when I was younger?” Maybe I’d been mistakenly using Buddhist concepts of mindfulness to explain away my inability to differentiate between these emotions, which had prevented me from recognizing the impact of my actions.
The Emotional Blind Spot
This realization led me to reflect on my own emotional landscape. I’d always prided myself on being self-aware, but was I really? Had I been confusing different emotional states, mistaking one for another, and in the process, missing crucial signals that could have guided me towards more empathetic behavior?
The Therapy Revelation
It was during this introspection that I remembered a conversation I’d had with my friend earlier that evening about my experience with EMDR therapy. I shared how, before therapy, I couldn’t distinguish between the fearful, worried voice in my head and the nurturing, supportive one.
As I recounted this to my friend, a new parallel struck me: just as I had once struggled to differentiate between these internal voices, I had also been unable to distinguish the fine line between shame and guilt. This confusion didn’t just lead me astray — it nearly led me to destruction, causing deep hurt to my family and the people I loved.
The inability to separate these emotions — fear from support, shame from guilt — had created a blind spot in my emotional intelligence. It was this blind spot that had allowed me to justify actions that, in hindsight, lacked empathy and consideration for others.
The High-Stakes Gamble
That night, as I lay in bed, I began to think about all the times where I, as a driven entrepreneur, had missed opportunities to show empathy to my family.
Years ago, as my wife’s due date approached, we faced a stark reality: we lacked adequate health insurance for the impending hospital costs. This financial pressure led me to a decision that, in hindsight, revealed my lack of empathy and foresight.
As I drove to the casino, I didn’t once think about what it must be like for her — sitting at home alone, a week away from giving birth, caring for our first child, and wondering what would happen if her water broke while I was away with the car. No, I was imagining myself walking into that hospital, peeling off hundred-dollar bills from a banded roll like Tony Montana. That was my perspective — me, the hero, saving the day.
Over the next few nights, I won two out of the four tournaments — double the money we needed for the hospital costs. No guilt, no shame, only good vibes. Winning cures everything, or so I thought.
The Echo Chamber
But in reality, my high-stakes echo chambers and emotional mufflers kept me from feeling the fear and anxiety I was causing my wife. My echo chamber consisted of poker buddies and entrepreneurial friends who valued risk-taking and reward above all else. I had gone all in, bet on myself, and won big. It was what we all prized. There was no one to tell me what an asshole I had been.
The Emotional Mufflers
Then there were the emotional mufflers. In our Evangelical circles, men were taught from a young age to be saviors, while women had little liberty to speak the truth of their lived experiences. Calling out their husbands or questioning his leadership was tantamount to questioning God’s hierarchical order. Consequently, I never knew how scared she truly was, and I would soon be ashamed at what I found out.
The Dark Night of the Soul
Later in life, I was “lucky” enough to lose it all — everything but her and the kids, that is. During that Dark Night of the Soul, she finally told me how she had really felt throughout our marriage. This time, without the high-stakes echo chambers and emotional mufflers, those once “worthless” feelings of shame and guilt came flooding back, but I couldn’t yet tell the difference.
The Shame Spiral
First came deep shame because my ego was wounded. I had always seen myself as the hero, the good guy, the protector. But, how could the actions of a hero terrify his family? How could a “good guy” gamble his family’s future without consulting them about their needs and wants? How could a protector rig up a tightrope, strap his family to his back, and march forward with no net?
The Sculpting of the Soul
In those moments, I couldn’t tell the difference between guilt and shame. When you’re first starting out with spiritual work — it’s a bit like sculpting. At first, you’re knocking off big, obvious chunks, making significant changes quickly. But as you go deeper, the work requires finer tools, more precision, and a keener awareness of subtle differences. Back then, those granular distinctions between guilt and shame were lost on me; they felt like the same overwhelming weight. It wasn’t until years later that I began to understand how crucial those small differences really are.
The Popcorn Ceiling Epiphany
One night, I was two years into a ground-up remodel of our home, determined to make amends and rebuild our world with everyone’s needs and desires in mind.
While scraping popcorn texture off our basement ceiling, I started reflecting on what I valued most. All I truly wanted was to see my wife and children in an environment where they received the support, nourishment, and resources necessary to thrive and achieve their fullest potential. What I was feeling wasn’t shame, it was the feeling of remorse for having missed the mark on what I claimed to hold most dear. This realization was my first step in distinguishing between the paralyzing nature of shame and the constructive potential of guilt.
Brené Brown says this:
…guilt is adaptive and helpful — it’s holding something we’ve done or failed to do up against our values and feeling psychological discomfort.
I had been mistaken about guilt. It wasn’t just an emotion dragging me into the past; it was much more than that. Guilt acted as a trigger in the present, reminding me of past choices that conflicted with my current values. When those memories resurfaced, they created a disconnect — a sense of guilt that could either paralyze me like quicksand, pulling me back into the past, or fuel me to make better choices moving forward. If I allowed that guilt to consume me, it would indeed be worthless. But if I used it as a catalyst to build a life more empathetic to my wife and kids, that guilt became invaluable.
The Road Back
As I crossed the border back into Iowa, I revisited that scene in “Presumed Innocent” about the self-absorption of shame and the accountability of guilt.
Maybe it’s natural, as we progress on the spiritual path, to feel more shame than guilt at first. Initially, much of our identity is tied up in false notions of self, deeply connected to the ego. When those layers are exposed to contradictions, we feel ashamed, as if we’ve been caught pretending to be something we’re not. But as we continue to shed those layers and identify less with the ego, there’s less to be ashamed of because we start to recognize who we truly are. What remains are the memories of past choices and the opportunity to keep doing the Work — living in a way that aligns our actions with our values, reducing our own suffering and that of those around us.
The Golden Opportunity
As I pulled into my driveway, I realized: guilt isn’t just about acknowledging the pain we’ve caused others; it’s about taking responsibility and using that awareness to grow. Shame may be self-absorbed, but guilt, when properly harnessed, is the key to accountability and real change. It’s what allows us to evolve from ego-driven beings to individuals capable of empathy, compassion, and connection. And that, I realized, is the real work of a lifetime.
A Final Thought: The Chagrin Factor: I shared this idea about guilt versus shame with a friend, and they offered an interesting perspective. They prefer to use the word “chagrin” when apologizing for something they did. It’s a subtle but meaningful distinction: Shame is toxic, guilt brings awareness, and chagrin? Well, chagrin is simply recognizing an “oops” moment and moving on with grace.
