Why Success Doesn’t Always Feel… Successful

Unnerving Success Man Repeller


oward the end of 2017, as the publication of my first book loomed, I experienced a growing sense of anxiety and self-doubt about what I felt should have been the greatest success of my career so far. I’d loved the grind of writing the book — of researching, interviewing, drafting and redrafting. But the sprint to the finish felt more like a nervous crawl.

Every friend I saw asked me how my book was going. Every new person I met congratulated me on the nearing milestone. I’d smile and say what I was supposed to, then privately labor over edits to the final draft, questioning the phrasing of my sentences and triple-checking my research.

After more than two years of work, I was terrified of exposing myself to critics. The imposter syndrome was so crippling that I got myself back into therapy two months before my publish date. I could tell others were expecting me to be having… well, a much better time. But their expectations also made me feel guilty and confused about what I wasn’t feeling: competent, excited or worthy.

Unnerving Success Man Repeller

Success rarely feels like people think it will, says Majo Molfino, a women’s leadership expert and career coach. It is often defined by the world, using external characteristics. “These definitions are often drawn up by families, friends, partners, schools, universities, workplaces, religions, and the greater media and pop culture,” she says.

Rebekah Montgomery, PhD, a licensed clinical psychologist in private practice in Washington, D.C., says we’re often expecting these external definitions of success to have personal meaning. “We imagine that success is going to give us a particular internal emotional experience,” she explains. “It looks like ‘successful’ people feel so smart, capable and confident, or have it all together, and we imagine success will feel that way. But when we expect success to prove or shift something internally for us, it often disappoints.”

Buying into societal versions of success as a means to satisfaction is often a hollow road. “I see this so often — even in incredibly successful people who achieve accomplishment after accomplishment and still don’t feel good enough,” says Montgomery. “We are often taught we need to achieve things to have worth, so you think, Once I’ve achieved X, I’ll feel good enough; I’ll feel worthy. But when you don’t feel worthy after achieving X, you start to think, well, I guess that achievement wasn’t successful enough. Then, you’re constantly moving the bar — and minimizing successes once you get there.”

There are gender norms around success and work that have been slow to change.

Success may also feel deeply uncomfortable, especially for women. Montgomery says her male clients do not struggle with embracing success in the same way her female clients do. “Women are often socialized to not take up too much space, not be too loud, not be too braggadocious, because it’s unbecoming, conceited, unattractive, or threatening; there are gender norms around success and work that have been slow to change.”

These conflicting messages — to pursue success, but not too much of it — can lead us to undervalue our own voice and power. Women may be more prone to feeling like frauds as we climb ladders or acheive markers of success. According to a 2018 survey of 3,000 UK adults, roughly two-thirds of women claimed to have experienced imposter syndrome during the previous 12 months versus roughly half of men.

Diana Bilimoria, PhD, a professor of organizational behavior at Weatherhead School of Management at Case Western Reserve University, describes impostor syndrome as “a belief that one has fooled others about one’s own competence, and that an unmasking is imminent.” People with imposter syndrome tend to attribute successes to the right cocktail of external circumstances — a lucky break, networking with the right person, being in the right place at the right time — and failure to internal characteristics, like a lack of competence. “Previous research has shown that women are more likely than men to exhibit an internal attribution of lower performance, while men exhibit an external attribution of lower performance,” says Bilimoria. That means women are more likely to blame themselves instead of circumstances for failures, setbacks and struggles.

Unnerving Success Man Repeller

Montgomery’s also observed something else in women — the belief that with each success we earn in life, something is also taken away. “Many feel like success is going to come at a cost,” she says. “They think, will I lose connection or relationships? Will I be criticized or shamed? Will people be threatened by my success?” Women also tend to perceive going for higher-level positions as potentially harmful to their well-being. Research from and McKinsey shows that the pathway to success and C-suite positions “is more stressful for women,” says Molfino. “That’s real.”

The stress of success can prevent a woman from being fully “present for the journey” as they hit major milestones. Part of the solution, says Molfino, is redefining the peaks of the journey through experiences that feel the most personally satisfying. “When I work with a client, I often have them get sober about what success means to them, and not what it looks like to the world,” she says.

Whether that definition involves a book, a job promotion or a certain stride in mental health, it’s important to remember something we regularly get backwards. “Success does not prove our worth,” says Montgomery. “Believing, sharing, and expressing aspects of our worth lead to success.”

Looking back, my book was not a New York Times bestseller or a critically acclaimed work to add to the canon of American literature. But it did open the door to entirely new ways of thinking, allowing me to hear the stories of countless women and promote the self-awareness I needed to have my first healthy, long-term relationship. Had I taken the time to define success this way before it was published, I might have enjoyed the final leg of the journey.

Illustrations by Madeline Montoya.

Jenna Birch

Journalist, dating coach and author of The Love Gap.

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