We idealize success and demonize failure.
People, sometimes, ask me how to stop obsessing over both, entering treatment distraught because they’ve failed to live up to some personal expectation or to satisfy someone else’s. I recently had a session with a client who told me that she was terrified of being boring and that her boyfriend would leave her as a result. In her mind, there were these glamorous, interesting people and, then, there was her.
The media (and, for the most part, each individual on Instagram) portrays certain lives in magical ways. It seems like the lucky ones have the perfect relationships, the ideal jobs, and the best friendships available. And in speaking with most of these folks, one’s conceptions of them are quickly confirmed. Thus, many begin therapy with the notion of their own ineptitude; somehow, they must have done something wrong. Yet, in stark contrast to the apparently countless happy people on Instagram, they compare their lives to illusions, dreaming up idyllic scenarios and visions of grace. Unbeknownst to them lies the truth of reality.
Most of us, especially when young, create and experience an all-encompassing sense of hope. We think of life mainly in terms of its potential good, ecstatically sharing our visions and plans for brighter days. For some, hope is the one and only thing carrying them through, while, for others, it’s precluding them from experiencing still unfelt joy. Hope is both wonderful and pathological. And it’s the latter incarnation that contributes to several forms of mental illness.
When my client told me that she considered herself to be boring, I couldn’t conjure up a more interesting person, not because she led a particularly exciting life, but because no one I met was more fascinating than her. She was insightful, curious, and optimistic; I’ve met plenty of people who didn’t even possess one of those traits. But, in her mind, she compared herself to carefully curated images of people who didn’t exist. During our dialogue, she became a little bit more desensitized to success, acknowledging its inability to radically alter one’s life. It’s nice, but life changing? I highly doubt it.
Personally, everything that I thought would drastically change my life’s trajectory only did so to some small extent. The things I thought would finally make me feel successful didn’t and, conversely, I eventually moved on from my various failures. The dread and sense of hopelessness that accompanied each evening before a big event eventually subsided. After a few of them, you realize that you won’t truly be happy after they’re over. The thought after each ends: on to the next one. However, and fortunately, failure works in much of the same way. Each time I didn’t receive something I desperately wanted, I found the resolve to move on. I felt certain of experiencing unending misery without each of those prizes, yet, somehow, my mind adapted, even to the point of being able to think about all of the things I would have missed out had my wishes been granted.
Envy, the desire to have the life that you don’t and someone else does, is based on a misconception stemming from black and white thinking: that your life is terrible and another’s is great. Much of our suffering originates in poor thinking. And looking back on my life, I can’t point to one personal moment or thing that significantly changed it. I recall losing people, but my failures rarely, if ever, defined me in the long-term. What seems so heartbreaking at first eventually transforms into a memory of something mundane. But I clearly remember the nights spent in agony and the sheer dread of fucking up an important moment. Those events came and went, and so did my fear, but I grew tired of causing myself unnecessary suffering. So, I began to envision my life without each one of them, asking myself: would it be markedly different if this or that didn’t happen? Usually, the answer is no.
Leon's Existential Cafe 
In my experience, the fear of being boring, framed in the way you described her, sounds like someone who is obsessed with the image they present to others. That obsession is just too familiar as narcissism, and this person would probably make a great narcissist, once she hit whatever level of success and joyous, non-boring, energy she views as rare or elite. As of now, she seems to be a bit deflated and obsessed about that feeling. She feels as if she lacks a certain spark or flare that others have, and she probably does. I mean, isn’t this the picture of an insecure person? Anti-social types like narcissists and histrionics do seem to have more fun. But you would think she would be glad that she wasn’t one. But the envy of seeing narcissists, who make everything look perfect, in a literal effort to make others jealous, and admiring the drama that the histrionic feeds on to literally make others feel bland, is not a good form of envy, not that any type of envy is good. But we do live in a culture where others are always seeking to make another envious, and greed us the best thing ever. Could she simply be an old school, sociopathic victim to our anti-social culture? I believe this person will find her anti-social, narcissistic knight and fall for him, and she’ll be coming to you with a much larger host of issues now that she followed her own disorder into a bad relationship, and still cant see that she did it on purpose.
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