To be loved by so many people who do not truly know one's real, authentic self can actually be a very lonely feeling. All of us crave the experience of being truly known for all of our foibles and strengths, and perhaps Winehouse was frustrated by people not seeing or hearing the "real" her. The loneliness that can come from this complex dynamic may have exacerbated her desire to use substances as a way of escaping the pain derived from that sense of loneliness.
To deal with her addiction, Winehouse reportedly tried in-patient rehab several times (even though in her hit song, "Rehab," she said "No, no, no"). So, what went wrong?
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Well, addiction happens to be exceedingly difficult to treat and devastatingly subject to relapse. So, in a certain sense, Winehouse was just like the millions of other non-celebrity addicts who don't benefit from rehab, and are more likely to relapse. However, there is another component to consider, both for celebrities and non-celebrities: enabling.
The Role Of Others And Enabling
Enabling occurs when those around the addict continue to engage in behavior that either encourages or fails to discourage the use of drugs and alcohol. Enabling can take many forms: giving the addict money, allowing access to a place to stay, a car, family, children, or other resources. It can be in the form of failing to create boundaries or consequences when the addict exhibits bad behavior.
To be clear, those around the addict are not responsible for the addict's behavior. However, they are responsible for their own behavior and should seek to minimize, and ultimately eliminate, enabling.
In Winehouse's case, it's easy to see how that enabling behavior was rampant. There were so many people whose lives depended on Winehouse, the singer, continuing to function and perform as an artist. If Amy Winehouse, the person, abandoned the music scene and truly committed to recovery, many would've surely lost their jobs. It probably would've taken years to treat her accordingly.
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If she made it past that recovery hurdle, it would also mean she would have to seriously overhaul her whole life. She would have to surround herself with sober friends and employees and stay out of the partying scene. Her brand, image and demeanor would've been significantly shifted as a sober Amy Winehouse. I fear that, as a result, some of the people in her inner circle enabled her. They did not encourage her to go to rehab, they didn’t draw boundaries for her poor behavior, and they didn’t provide consequences for her using. Instead, they attempted to prop her up so she could continue being Amy Winehouse, the singer. Amy Winehouse and Blake Fielder-Civil: A Relationship Timeline