The Toxic Triangle of Comparison, Guilt, and Judgment

Part 1: The Weight of Comparison

Comparison, guilt, and judgment are quiet yet powerful forces that subtly shape how we perceive ourselves and our roles as parents, partners, and professionals. Without even realizing it, we allow these feelings to seep into our daily lives, influencing our decisions, our sense of self-worth, and our ability to connect meaningfully with others. In this first part of the series, we'll delve into the unseen weight of comparison—the harmful expectations we place on ourselves, the societal standards that reinforce them, and how they steal our joy.

The Unseen Weight of "Should"

One summer afternoon, a conversation with my friend Sadie opened my eyes to the insidious nature of comparison. We were lounging by the pool, soaking in the sunshine, but Sadie wasn’t in a celebratory mood. It was her 36th birthday, yet she seemed weighed down by invisible burdens. I asked her what was wrong, and she replied, "I feel like I should have done more by now."

That simple phrase—"I should have done more"—captured the essence of what many of us experience: the constant pressure of not measuring up to some unspoken standard. We carry this weight of "should" around, letting it dictate how we view our achievements, our progress, and ultimately, our worth. But where does this pressure come from? And why do we allow it to have so much control over our happiness?

In Sadie's case, it wasn’t that she hadn’t accomplished great things; she had a fulfilling career, a loving family, and strong friendships. But the pervasive feeling that she hadn’t checked off all the right boxes by age 36 was stealing her joy. The "shoulds" of life—those arbitrary benchmarks we feel we must meet—often stem from societal expectations, social media highlight reels, or even our own comparisons to the lives of others.

Comparison Is the Thief of Joy

Teddy Roosevelt once said, "Comparison is the thief of joy." This quote holds true now more than ever, especially in our age of digital perfection. Social media has heightened our sense of comparison, allowing us to see curated, filtered snapshots of others’ lives and inevitably measure ourselves against them. We scroll through Instagram and Facebook, seeing photos of flawless homes, picture-perfect family vacations, and career milestones that make us wonder if we’re falling behind.

But here’s the thing: What we’re seeing is only the highlight reel, not the messy reality. We don’t see the struggles behind those perfect moments;the arguments, the failures, the missed opportunities. And yet, we compare ourselves, wondering why we don’t have it all together like everyone else seems to.

The result? We lose sight of our own journey. Instead of celebrating the unique path we’re on, we focus on what we lack. Comparison doesn’t just rob us of joy—it breeds guilt. We feel guilty for not achieving more, for not doing enough, for not being perfect. And from that guilt stems judgment—not only of ourselves but often of others, too.

The Cycle of Comparison, Guilt, and Judgment

Once comparison takes root, it begins to fuel a toxic cycle. We start by measuring ourselves against others, then feel inadequate or guilty for not measuring up. That guilt leads to self-judgment, where we critique our every move, decision, and achievement. And sometimes, we direct that judgment outward, criticizing others to feel better about our own perceived shortcomings.

This cycle can be especially damaging in parenting. The pressure to be the "perfect parent" is amplified by the constant flood of opinions, advice, and expectations that come from all sides. Should I be doing more for my child’s education? Should I be spending more quality time with them? Am I doing enough?

These questions aren’t inherently bad—self-reflection is important. But when they come from a place of comparison rather than genuine care, they only serve to make us feel inadequate. The truth is, there is no perfect way to parent. Each family is different, and what works for one child or household may not work for another.

The Problem with "Should"

"Should" is one of the most damaging words we can use with ourselves. It implies that there’s a universal standard we must live up to, a checklist of achievements or milestones that, if left incomplete, diminish our worth. But who defines these standards? Who decides what we "should" be doing by a certain age, in our careers, or as parents?

The truth is, much of what we believe we "should" be doing comes from external sources—societal expectations, cultural norms, or even the stories we tell ourselves based on what we observe around us. These pressures are often arbitrary and don’t reflect our true values or desires. Instead of focusing on what we "should" be doing, we need to start asking ourselves: What do I truly want? What brings me joy? What aligns with my values?

By shifting our mindset away from "should" and toward what feels right for us, we can begin to break free from the cycle of comparison and guilt. We can start to see our own progress and achievements for what they are, without measuring them against someone else’s journey.

Letting Go of Perfectionism

Perfectionism is often the byproduct of comparison. When we compare ourselves to others, we feel the need to be perfect—to live up to some ideal that doesn’t exist. But striving for perfection is exhausting, and it’s a goal that can never truly be reached.

Letting go of perfectionism means embracing imperfection and accepting that we are enough as we are. It means recognizing that life is messy, that we will make mistakes, and that those mistakes are part of the journey. When we stop striving for perfection, we allow ourselves to be more present, to appreciate the small victories, and to find joy in the moments that truly matter.

Choosing Joy Over Comparison

The first step to breaking free from the weight of comparison is to consciously choose joy. This means recognizing when we’re falling into the comparison trap and intentionally shifting our focus back to our own path. It means celebrating our achievements, no matter how small, and appreciating the unique journey we’re on.

When we let go of the "shoulds" and stop comparing ourselves to others, we open ourselves up to a deeper sense of fulfillment. We start to see our own lives for the rich, meaningful experiences they are, rather than constantly striving for something more. Joy comes not from measuring up to others but from living authentically, in alignment with our own values and desires.

In the next part of this series, we’ll dive deeper into how comparison affects our parenting styles, relationships, and even our leadership roles. By understanding how these unseen forces shape our actions, we can begin to make conscious choices that lead to healthier, more fulfilling lives.