A Little Happier: Why Andy Warhol (and I) Want To Have a Boss–on Retainer.

I agree wholeheartedly with Andy Warhol. Sometimes I wish I had a boss who could tell me what to do, so I wouldn’t have to figure it out myself.

Often, for me, the toughest part is figuring out what to tell myself to do.

Here’s the actual quotation, from The Philosophy of Andy Warhol (From A to B and Back Again), a book I love and have re-read several times:

When I think about what sort of person I would most like to have on a retainer, I think it would be a boss. A boss who could tell me what to do, because that makes everything easy when you’re working.

Agree, disagree?


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  • Gretchen S.

    Radical Candor Episode 6: “One of the most common mistakes bosses make is thinking their job is to tell people what to do. But that doesn’t work”

    • gretchenrubin

      That’s why you want a boss ON RETAINER. only when you want one!

  • Mimi Gregor

    Ooof! That would not work for me. Perhaps it’s because, as a Questioner, I am not outwardly motivated. People telling me what to do chafes. I already know what I have to do. If I’m not doing it, it’s because either something else takes priority at that moment, or I don’t really want to do it, but it’s one of those things that I must do anyway… so I procrastinate. What I would rather have is an intern on retainer. I wouldn’t want them to do everything, because some things I just do better myself (or so I think), or it is too much bother to explain how I want it done. But for the mindless jobs or repetitive errands that take me away from things I would rather be doing… yeah… an intern.

  • I could definitely like having a boss on retainer! I’m home full time, and sometimes, because I have so MUCH freedom of choice with my time, I sometimes feel like I “should be” more productive. I’m an Upholder and I love making my daily list of things to do and love crossing things off, but I think a boss on retainer could really be cool on days I feel less peppy.

  • Lauren

    I wholeheartedly agree with this statement. I work at a job that gives me too much freedom, so I begin to “spin” in my head which results in no work being done.

    • Lauren

      P.S. Im an obliger (obviously). Wish I could have someone else write my to-do list! That would be a dream. haha

  • No thanks!. Like Mimi, I’m a questioner with significant rebel tendencies. I can work with a colleague or collaborator where we jointly decide, but I don’t like the authoritarian overtones of a boss. I actually did a blog post last week on this subject: https://curioussteph.com/2017/08/02/other-peoples-rulesneed-to-know/ Having been self employed for the past 16 years, it would be very difficult for me to go back to having a boss. Interesting question!

  • msps

    I’m with Mimi Gregor. Also a questioner, I have had more than enough of bosses telling me what to do, and more often than not not knowing themselves much of anything about how to do my jobs. This has abated somewhat since I became a lawyer because I value input and other perspectives; no one can think of everything relevant or useful in anything but the simplest tasks, and not always then. However, input and other perspectives do not correlate with a boss telling me what to do. I generally know what to do or can figure it out without someone telling me what to do.

    I like her idea of an intern, or an assistant. Someone who could take direction and execute well, that would be great

    • Cindy May

      Me too! An intern is definitely the way to go. I wish I could coerce my teenage niece into being my personal assistant, but not sure I could afford her rates and don’t want to be her social media fodder.

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