In case you've never noticed, I rarely interview anyone for this column. Most of my sources are family and unsuspecting friends who complain that I make everyone look bad. But it is not true. It is true that they THINK I make them look bad, but in fact, I could rip them apart in my column, and I do not, in the spirit of being invited back for Thanksgiving and Birthdays.

Recently, I have taken up columnist tasks that require me to interview strangers. And, like the courtesy I give to my family, I do not trash the people I interview. But I am at my breaking point. Some people are so incredibly stupid about their career that I actually struggle to make them seem intelligent during the interview.

So here are two interviews from smart people who are career idiots. (But first, a caveat: I am making the people anonymous. Many readers generously send stories from the field. And really, I love to hear from readers. I learn a lot. So you should know that if I think you're an idiot and decide to write about it, I will at least disguise your identity.)

Career idiot number one: The Apprentice. Not all of them. Just the unlucky one I interviewed. He really did not have a career, which was, undoubtedly, the cause of his ridiculous antics on the TV show that eventually got him fired. But he decided to make a career out of getting fired by becoming a public speaker.

Here are things you need to become a public speaker:
1. Something to say. This guy had nothing. Except to tell me that he was available for speaking.
2. You need an ability to answer questions from the press so that your name gets in the paper and people recognize you and hire you as a speaker. He did not answer my questions, which were all softballs. And he even asked to see the notes I was writing so he could edit them. I laughed.

The lesson from this career idiot is that if you must be a poser, pose carefully. When you first start being something new, (for him, a public speaker) you need to pretend you are that person so people hire you as that person. But do some research before you start pretending. At least learn the basics of how to conduct yourself, and what people will ask of you.

Career idiot number two: The painter whose identity I probably don't even need to hide because you don't know him because he's never sold a painting.

He makes a lot of money as VP of Something Big at his tech company and he gave notice six months before his wife quit work to have a baby. He is starting a career as a painter. He has no idea how to get his art to the market, or how many pieces he'll have to sell to support his family. But he says he has to be true to himself, and painting is his dream.

He says he feels trapped at his current job. This is the picture he paints of trapped: He wanted to move across country, so his large and generous company let him set up remote office in his new home. He hates the long hours of his lucrative job, and his company would let him go part time, but he doesn't ask for that because he doesn't want to like his job. He fears that if he liked his job he wouldn't quit to do his art.

Here is the lesson from career idiot number two: Take a big-picture look at what you have. It might be a lot better than you realize. Remember the first time you woke up next to the love of your life, and up close, in the morning, their face looked splotched and scruffy and gross? Well jobs are like people; they never look great up close so you need to pay attention to the big picture. This guy's big picture is that he has a great job for supporting his new family and painting on the side, and if he's really an artistic genius then he can make a bundle painting and quit his job.

I hate to be a buzz kill here. I'm not saying that I don't like dreamers. I do. I like people who reach for careers that are fulfilling but difficult. But just because the odds of success are low doesn't mean you have to make them lower with poor planning.

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17 replies
  1. flykoo
    flykoo says:

    And how about a person, who really believe, that he (in this case it is my old friend) will be the President? Its funny, but I concider him not a dreamer, but a child, who think that he’ll have everything.

  2. Professional Resume Writer
    Professional Resume Writer says:

    Hi Penelope!

    Just found this post and have to comment on it. I’m definitely less the dreamer and more the realist.

    #2 If that were my husband, I’d kick his a@$! A new baby on the way and he decides to quit his job and follow his dream to paint? Then moonlight on weekends or something at a gallery (not that his new-mommy wife would appreciate his absence). Or go to part time and do paint with the other 20 hrs you would normally be working.

    I hear similar stories in my own business with folks who tried the dream and unfortunately it didn’t work out. So now, a year and a half to two years later, they are trying to get back into their old industries/jobs and THE COMPETITION IS TOUGH!

    Not saying to NOT go for your dream, just saying to do it when the timing is right… like after you’ve been laid off! :)

    Interesting post!

    Erin Kennedy
    Professional Resume Services

  3. Education Center
    Education Center says:

    weekends or something at a gallery (not that his new-mommy wife would appreciate his absence). Or go to part time and do paint with the other 20 hrs you would normally be working.

  4. Ancilla Tilia
    Ancilla Tilia says:

    Just found this post and have to comment on it. I’m definitely less the dreamer and more the realist.

    #2 If that were my husband, I’d kick his a@$! A new baby on the way and he decides to quit his job and follow his dream to paint? Then moonlight on weekends or something at a gallery (not that his new-mommy wife would appreciate his absence). Or go to part time and do paint with the other 20 hrs you would normally be working.

    I hear similar stories in my own business with folks who tried the dream and unfortunately it didn’t work out. So now, a year and a half to two years later, they are trying to get back into their old industries/jobs and THE COMPETITION IS TOUGH!

    Not saying to NOT go for your dream, just saying to do it when the timing is right – like after you’ve been laid off! :)

  5. Brad
    Brad says:

    The painter story is funny. I guess it was 2005 when he quit his job? Would he make the same move today? I wonder if he is still painting.

  6. Steve
    Steve says:

    Give the 1sgt guy a break. He’s a young apprentice who is trying to become the an alpha male, so he will blidly take on anything you can throw at him and try to blag his way through it.
    No 2 needs to communicate with his wife and then ask himself if he really needs to be painting or bringing up a family. you can paint when your retired not when your holding the baby.

    how about painting with used Dypers! You never know with the art world. Look @ tracy emmin

  7. Natalie Loopbaanadvies
    Natalie Loopbaanadvies says:

    What interesting stories you have here. I agree with Steve, be a little more kind to guy number 1 as he is just new to that work. Though he really needs to do a little research so as not to embarrass himself. As for guy number 2, he should at least be thankful that he has a job that could suffice to the needs of his family. Even though he has a job, he can still paint whenever he has some free time. Until he’s sure that he’d be able to sell his paintings, he should keep his job for a little while.

  8. Evan
    Evan says:

    These are indeed funny stories. You got to give these people some points for actually having the guts (or lack of other things) to want to take that risk. Sometimes, good things come out of taking such risks. Others have the planning capacity, the career savvy but never get where they want to be just because they never take that risk.

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