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Ask a CEO Coach: Why Do My Wins Feel Fleeting While Losses Linger Forever?

5 April 2025
ask a ceo coach why do my wins feel fleeting while losses linger forever

What keeps you awake at night? The thrill of victory or the agony of defeat? Many of us, especially those in high-stakes environments like entrepreneurship, often find ourselves wrestling with the discrepancies between our wins and losses. Why is it that victories feel so fleeting while losses seem to cling to us like an unwelcome shadow?

It’s a common sentiment among leaders and entrepreneurs alike. For someone like Omid, a successful agency head in Atlanta, this question takes on a particularly personal weight. He shares the joy of industry recognition alongside the sting of lost opportunities, revealing a pressing dilemma: how do we transition from celebrating our wins to genuinely processing our losses without being consumed by them?

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The Weight of Loss vs. the Lightness of Victory

The Entrepreneurial Mindset

As an entrepreneur, the emotional landscape often feels like a roller coaster. When I first embarked on my journey, it was all about the adrenaline of launching something new, the thrill of overcoming challenges, and the anticipation of success. But with each win—each new client, each award—the high seemingly dissipated far quicker than the emotional toll of a setback. The truth is, while I might revel in accolades, I would find myself haunted by the ‘what could have been’ of lost pitches.

How Losses Resonate Deeply

There’s a unique pain associated with failure that can’t easily be shaken off. With Omid’s situation, he realized that despite his recognition as “Agency of the Year,” the feeling came and went within a day. Meanwhile, the sting of losing a hard-fought pitch lingered, feeding into a cycle of doubt and anxiety. These emotional scars led me to wonder if there was a way to recalibrate how I processed both victories and defeats.

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Balancing Wins and Losses: The Emotional Diet

Why Losses Linger

I’ve discovered that emotions, especially negative ones, have a tendency to weigh heavily on our mental health. Research suggests that losses can create a profound emotional impact because they often feel more significant than gains. The brain’s response favors survival strategies that make us more alert to dangers—a lost project is perceived as a danger, while a win, though sweet, is often not equipped with the same survival signal.

Harnessing the Value in Loss

Interestingly, there’s a flip side to the grimness of losing. Omid highlighted that the transient nature of his victories, while frustrating, serves to keep complacency at bay. The nagging fear of losing is a powerful motivator, urging us to keep improving, to keep innovating. I’ve come to realize that leveraging disappointments for growth can transform fears into fruitful lessons.

Rituals as a Path Forward

Creating a Time Box

Bill, my coach in this conversation, suggested an intriguing concept: time boxing emotions. Just like a seasoned athlete might process a loss in dedicated sprints of anger or frustration, I learned the importance of allotting specific periods for each emotion both after a victory and in the wake of a defeat. This isn’t just about feeling; it’s also about committing to a timeline for moving on.

SituationEmotionTime Allotted
WinningCelebration1-2 days
LosingGrieving/Processing20-30 minutes

Ritualize the Experience

Creating rituals around both wins and losses might seem trivial, yet it’s incredibly potent. Whether it’s shaking hands with my team in celebration or going for a short walk to process a loss, these small rituals anchor the emotional experience, allowing me to contextualize it properly. Omid’s reflection proposed a striking method of throwing rocks into a lake to symbolically cast away the negativity and anger connected to losses. It’s in these physical acts that I find a channel for release and rejuvenation.

Gaining Perspective

Understanding the Bigger Picture

While the day-to-day victories and losses can feel overwhelming, framing them within a larger narrative helps maintain perspective. For Omid, recognition is fleeting, and so is the health of any business. I’ve begun to remind myself that every loss is just a line item in the grand narrative of my journey. Re-framing these experiences as necessary growth steps moves them to the periphery rather than letting them dominate my emotional landscape.

Building a Support System

None of this happens in a vacuum. Having mentors, colleagues, and friends to confide in about successes and failures can help chart a more balanced emotional response. Conversations with fellow entrepreneurs often illuminate shared experiences and strategies for managing the emotional highs and lows. This community aspect fosters resilience, making the impact of losses less isolating.

The Art of Mindfulness

Practicing Mindfulness to Combat Negativity

One of the most effective tools I’ve embraced is mindfulness. By engaging in practices that ground me in the present, I can cultivate a healthier emotional response. Simple techniques, such as focused breathing or yoga, allow me to process feelings without being overwhelmed. When I can observe my emotions with curiosity rather than judgment, I bring clarity to what I feel rather than allowing fear to run rampant.

Accepting and Letting Go

Understanding that both victories and losses are transient is a powerful realization. Acceptance doesn’t mean defeat; rather, it means allowing myself the grace to feel and the strength to move forward. It’s reminding myself, as Bill wisely noted, that every experience leaves an imprint that shapes my path. Losses don’t have to define me anymore; they aren’t failures but rather opportunities for growth.

Sustaining Long-Term Success

Cultivating a Growth Mindset

Through all of this, I’ve realized the importance of fostering a growth mindset. Instead of dwelling on a lost pitch or the fleeting satisfaction of a win, my focus shifts toward continuous improvement and learning. Maintaining curiosity about experiences has enriched my journey as an entrepreneur, translating emotions into insights.

Sharing the Journey

As I navigate the highs and lows, I recognize that being open with my partners and employees is invaluable. Sharing my own triumphs and tribulations humanizes the experience of entrepreneurship. Instead of encouraging a culture of chasing accolades, I can foster an environment grounded in authenticity and support.

Conclusion: A Journey Worth Celebrating

At the intersection of victories and losses lies a nuanced dance of emotions that entrepreneurs like Omid and I must learn to navigate. Rather than allow losses to shroud my path and victories to slip through my fingers, I’m learning to embrace both with intention.

Ultimately, the goal is not merely survival in the world of entrepreneurship but thriving amidst its chaos. In understanding the nature of wins and losses, I create space for growth and resilience. Each loss can be an opportunity dressed in fearful garb, while every fleeting victory is a moment to be cherished, no matter how brief.

In this journey, I’m not only shaping my path but also fostering a culture among my team that values emotional processing as much as it does innovation and accomplishment. Because at the end of the day, it’s not just about the wins and losses it’s about how I show up for both. As I keep reflecting on these insights and rituals, I can take each day as it comes, armed with the knowledge that both wins and losses are an integral part of my entrepreneurial narrative.

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