Guest post: How I manage up, working for Penelope

This is a guest post by Cassie Boorn. She works with me at Quistic. That’s a photo of Cassie and her son. And here’s another guest post she wrote, before we started working together. 

A few years ago I targeted Penelope as someone I want to work with. Then I spent a lot of time and energy getting her to hire me. You can probably tell from reading this blog that Penelope would be a difficult boss. I work hard figuring out how to make her like working with me. This is called managing up. And these are rules for managing up that I’ve learned from working with Penelope:

1. Show how you can improve the bottom line.
When I’m first getting to know Penelope I tell her she could make money if she did an online course. She says no and it would be too much work.

It takes two months to convince her to do a course, one week to convince her to publish the course on her blog, and one hour for her to realize this was the best idea ever and she is going to make so much money.

The way that I convinced her to do the course was by offering to handle all of the details. But I can’t. Penelope fires me 30 hours before the course starts. But she makes a lot of money, so she sends me a thank you note.

2. Don’t ask for favors. Earn them.
I have spent twelve months traveling back and forth to New York, and my life is falling apart. Penelope thinks I should move out of Peoria. I think my son will miss his father too much. I tell her I am staying in Peoria. She tells me to find a new job.

I call Penelope every day to tell her how much job-hunting makes me want to die. She tells me how it’s a good experience for me. I tell her how amazing my resume is, and she tells me that I am not special. She reminds me that while I have a well-written resume because she wrote it; I don’t actually have any skills.

I am standing in a hotel room the first time Penelope suggests we do a startup together. I am so happy that I dance around the room, but only in my mind. I appear calm because if I give her even one sign that I want to do a company she might take it back.

3. Push back on your boss when it’s really important.
I could spend my entire day thinking about ideas. Penelope tells me I can have any job I want, but whatever job I choose must have deliverables. We end up screaming at each other about how I don’t want deliverables and she reminds me that we are in a startup, so everyone has to do stuff they hate.

We decide I will do sales because I am good at coming up with ideas about what we could sell.

When Penelope hired me, she thought I was an ENTJ, like her. Had Penelope realized I was an ENTP, I wouldn’t have a job.

She says, “Did you see how much more money ENTJ’s make than everyone else?”

I say, “Yeah. I sent you that link.”

Penelope reminds me on a daily basis that she will never hire another ENTP.

I tell her that hurts my feelings.

She says it shouldn’t. She says I’m lucky she takes all this time to argue with me. She only does it with people she cares about.

4. If your boss gives you work you hate, hire someone to do it.
I tell her I am bad at details so we need to hire  someone to help me with details.

She says that I was terrible at managing the freelance designer, and the copywriter I was managing quit, so I can’t manage anyone else.

So, I hire my friend Katie to do all the details of my job. Now my career feels like my own little business. I tell Penelope that companies aren’t hiring lower level employees, so maybe this will be the new model. Instead of professionals hiring house cleaners or nannies to run their house, they will hire people to do the parts of their work they hate. Maybe this is how millennials do work/life balance.

Penelope tells me I’m a genius.

5. Pick a boss who treats people how you want to be treated.
I am sitting in Penelope’s hotel room while her son practices cello.

She sits on the floor in front of him. I have never seen her focus on anything so hard. She catches every move, and yells reminders at him: eyes on the bow, better bowing, remember to end with your bow down. I wonder if Penelope played cello. I wonder if she could play from the memory of watching her son.

He finishes the song, and she asks him to play the end again. The song ends with the bow down, but he had ended with the bow up. I wonder how she could remember all of the terms. He thinks the song ends with the bow up, so they get the sheet music out to find the answer. He’s not frustrated, but I would have thrown the cello at my mom twenty minutes ago.

After studying the music they conclude that the song ends with the bow down. He is happy she caught his mistake. Penelope sings the notes she wants him to play, “ba ba baba ba.” She has the song memorized.

He sits down to play and Penelope settles down to watch. I have never known someone so invested in the success of other people.

This is a guest post by Cassie Boorn

46 replies
  1. darja
    darja says:

    oh god. yesterday i wrote an email for penelope, still need to push send. but will she ever read it if i now say i am an ENTP?

    • Lucy Chen
      Lucy Chen says:

      Hi darja,
      I’ve sent Penelope a few emails about homeschooling, and she always not just read my email, but replied!! I was surprised by how approachable she was!

      • darja
        darja says:

        hey, nobody can be THAT perfect…not even penelope:))))
        thank you for the encouragement,
        but i may take a personality test again :)))
        hard years of stay-at-home-mom life might have changed the result :))

  2. beatrice
    beatrice says:

    You make a great team. We could all use that one person to balance us out who has our best interest at heart. Not easy to find, but when you do, hang onto it.

    Happy new year!

  3. Sheri Bruneau
    Sheri Bruneau says:

    What a great post Cassie! I especially like #2 – Don’t ask for favors. Earn them. Being an INTJ myself, that’s not surprising. Thanks for the read this morning!

  4. Patricia
    Patricia says:

    Uh…no thanks! I worked for a crazy lady a couple of years ago. Small company – but this lady lived large claiming she was raking in dough. She also drank like a fish and constantly screamed at everyone. Very stressed about success and money (and paradoxically very impressed with herself at the same time). Well, the great recession happened and turned out the money ran dry. A few of us were laid off (thank God), so now when looking for a job I specifically look for “high performers” and stay away! In fact, I look for less prestigious institutions…turns out they’re full of good people and sanity. I can’t be the only one who has figured this out…

    • Monica
      Monica says:

      I used to feel this way until I actually took that path and made the responsible choice for once.

      I took a marketing job at this very vanilla company in the financial sector after being told that I “attract insane bosses who offer me jobs and then turn out to be crazy.”

      My boss was a normal dude who was pretty smart but also less adventurous. It paid extremely well (probably more than I was actually worth) and was just as boring as I’d imagined. I quit after 9 months (in my head, I quit after 4).

      I’m still optimistic that there is a balance between “boring boss who doesn’t inspire me” and “interesting boss who makes everyone’s lives hell.” For me, right now, that balance is working on my own projects and building a team of interesting mentors who will send me freelance projects but don’t own me completely.

      That said, I think it’s great that Cassie and Penelope have a good relationship, and also, if you want your job to be exciting you will need to accept some level of drama. This is true of relationships too, for the most part. I have found many relationships where the drama (unproductive) fades into total trust and understanding (productive), and that is absolute magic! It takes a lot of work to get to that point, though. I would like to think I will experience that with a boss/mentor, someday.

      Like Cassie points out at the end, if you can get your ego out of the way and learn to accept criticism gracefully, you can learn so much. I think most people (including myself) have trouble with that and opt out of most of those potential work relationships. We all have our boundaries, and we all need to find people who will push us without steamrolling us. It comes down to finding the style that works and how much drama you are really willing to put up with on a daily basis. And then being extremely patient and trying and trying and trying to make it work.

      • Patricia
        Patricia says:

        Good point! You made me laugh…very true. It’s good to try, keep trying and try again. My point is that I’m not going to tolerate drama and abuse for the sake of being able to brag about my urban workin’ gal career. What I do now is by no means boring. Insanity is not synonymous with excitement. Drama…usually it’s just a sign of a mentally ill person running the place.
        You probably “attract insane bosses” because you’re nice and safe for them to beat up on (seriously, it’s not you with the problem – it’s them, stay nice!). I have not had that problem – one crazy boss was enough for me – but I do know many, many awesome people that fall into your category. Of course, you never know what the future holds…keep your fingers crossed that none of us end up with a loon again :)

  5. GenerationXpert
    GenerationXpert says:

    Interesting post. I connected with what you said about your feelings getting hurt.

    I also work with a boss with Aspergers. So often he’ll send an email letting me know EXACTLY what he’s thinking about something. And it’s usually a small thing that I don’t care about much, but I think to myself, “Why do you have to be a dick about it?” Seriously, I’d make the change or whatever if you just said, “Make this change.” I’m thinking maybe that’s my feelings being hurt.

    This is my 20th year I’ve been working after getting my undergrad. I’ve kind of given up on getting a boss who’s not a lunatic. I’ve just gotten really good at managing crazy. And building a little box in which I can put all the hurt feelings and douchey comments in and forget about them. Seems to be working. I got a big promotion last year.

  6. Grace Miles
    Grace Miles says:

    This is awesome in more ways than one, Cassie. I love the last point– it’s the golden rule with a twist.

    There have been studies suggesting that when you watch someone do a task, your brain experiences it firsthand as well, so it feels like you’re doing that task. Playing a string instrument like the cello is intricate, not even accounting for musicality, but I wonder if this means Penelope has been practicing the cello through Zehavi– so they should perform a duet sometime, maybe. It’s sweet how you noticed this connection.

  7. Larry Hochman
    Larry Hochman says:

    If you haven’t read The Fountainhead by Ayn Rand, this won’t mean anything to you. But Penelope reminds me of Howard Roarke. Precise, not particularly worried about please his subordinates, but they loved him for his congruence and the quality of the work he demanded and executed.

  8. Chris M.
    Chris M. says:

    What I didn’t like about this post is that it mimics Penelope’s writing style.

    Even I could write a guest post precisely like this, and get people to praise it, but it would be just a mechanic reproduction of something that is authentic with Penelope but to me sounds fake with another writer because it’s not using the author’s voice.

    • Julie the Wife
      Julie the Wife says:

      Actually, I know Cassie personally, and this is written exactly how Cassie talks. I’m sure working together also makes them write similarly, since they are writing to the same audience.

      • Penelope Trunk
        Penelope Trunk says:

        This is true, it’s how Cassie writes.

        An aside: When I was in graduate school for writing one week my peers surprised me in workshop by bringing in parodies of my writing. The experience of hearing everyone read their parody out loud has made me very aware – in a cringing sense – when someone is changing their writing to sound like me.


  9. Van
    Van says:

    It really feels like there is a huge amount of anger in this post. Which I can understand, given these anecdotes. Penelope is widely known for being batshit crazy. Just google David Dellifield for an example. One has to wonder, why does this writer keep working with her? Like the comment about the cello, I would have thrown something at her a long long time ago.

  10. Vicky
    Vicky says:

    5. Pick a boss who treats people how you want to be treated.

    Also applies to husbands, though most women don’t don’t feel they deserve that.

  11. Jennifa
    Jennifa says:

    Well two things about Cassie impress me here, one she knew what her strengths were and focused on them, second she knew when not to quit.

    Those two things are real tough ones for me to weed through, good for Cassie she was able to figure this out!

  12. Rachel C.
    Rachel C. says:

    Point 4 is absolutely the future of business. I’ve always been a big believer in working smarter and incedentally have become great at hiring outsource employees online. It’s definitely the only way for a working mom to survive.

    I’ve always been confused about Penelope’s identification as an ENTJ since she regularly mentions wishing never had to talk to others. I would have pegged her as an INTJ who likes to talk, like myself.

    • IMKenny
      IMKenny says:

      Penelope (like me) has Asperger’s syndrome and experiences social interaction differently to most people. Having seen her on YouTube, though, she is more outgoing than I am (I am INTx where x=borderline P/J), so I expect what you are seeing in Penelope is “extroverted Aspie” rather than “introverted neurotypical” (=NT).

      I have seen a few Aspies say that they are extroverts and like being with people but experience sensory overload in social interaction and need time out for that reason. This is not necessarily the same thing as the introvert’s need for time alone. For me, the introvert need for solitude and the Aspie need for relief from sensory overload are all blended together. As far as I am aware, one need arises from brain activity (introvert vs extrovert), the other need from sensory overload (Aspie versus NT). The introvert’s brain is already active in solitude, while the extrovert is just bored. The Aspie’s brain is overwhelmed by sensory complexity, while the NT is fine (relatively speaking).

  13. Derek
    Derek says:

    I ran across this site by accident, googling living simply (those kinds of ideas and looking for outdoor places to explore are my main reasons for getting on the net) and am a bit fascinated by the hunger of more more more, that this site seems to esteem
    This particular post horrified me a little, for (and because of) both participants. It seems to be a very complicated and demanding life and it’s hard for me to understand why people would choose it.
    Good luck and best wishes to you both!

    • Jennifa
      Jennifa says:

      Derek, I looked through your blog last night, and the pictures are all so dreamy, I still remember them this morning.

    • Helen
      Helen says:

      I’m with you, Derek! I come and read here every so often, as a view into a particular kind of bizarro- US – world, and it reminds me to be grateful for my own, non high-performing, ordinary-earning life.

  14. laura
    laura says:

    I really enjoyed this post. It confirmed that Penelope would never hire me as I am an INFJ but that is OK…..I learn so much from this blog.

    • Penelope Trunk
      Penelope Trunk says:

      Guess what? I needed a driver to take me and Zehavi to Chicago and back each week, and my assistant suggested her friend. And I said no way am I hiring an INFJ. And my assistant told me to just give it a shot.

      I complained. I said that INFJs never like their job and no one is ever good enough for an INFJ and we would argue.

      But it turns out that I like spending eight hours in the car with her. She is interesting. I like that she has opinions about everything. And I like that she doesn’t mind when I need quiet time. She’s reliable and smart and always interesting to talk to.

      So there you go: I hired an INFJ and I like it.


      • Laura
        Laura says:

        Good to hear!! Your respnse, Penelope, made me laugh. Nice to know INFJ’s are good for something….

        It also made me think of that Katie Perry song, “I kissed a girl and I liked it”. LOL

  15. Lucy Chen
    Lucy Chen says:

    No.5 is so so touching!

    But it makes me wonder about homeschooling. Do I have to be as good as Penelope to homeschool my children? Because I doubt I’d ever be as good…

  16. Latika
    Latika says:

    I guess you have a great experience working with the Penelopetrunk team Cassie. Congrats and best of luck for your future assignments.

  17. Katie
    Katie says:

    Why does one need to say ‘I can’t hire/or be friends with/or drive with/or talk to/etc an INFJ or ENTJ or whatever combo thereof ‘box you into a pre-packaged personality model’? That’s not how we are made. Interact with the person not their ‘personality letters’. No one is a one size fits all regardless of popular social/personality profile. Take a deep breath, quiet your heat, interact, trust your instincts and move on or forward. You can do it!

    • Jennifa
      Jennifa says:

      I have always assumed that was a little tongue in cheek humor there, not that PT would actually totally base hiring decisions on 4 letters. But maybe I am wrong.

  18. Jeni
    Jeni says:

    How is it that ENTJ’s are better than making money at INTJ’s? I believe that it’s true. I am an INTJ and have been broke all of my adult life. Do I change myself? Or is there no hope of changing because how can someone change their personality?

    • Penelope Trunk
      Penelope Trunk says:

      Jeni, your first instinct is right – you can’t change your personality. You can work on your weaknesses, but for the most part, people don’t want to work on their weaknesses. For example, an ENTJ makes more money than an INTJ because an ENTJ is good at selling ideas. INTJs can implement ideas better than an ENTJ, but selling is harder. That said, most INTJ hate doing sales and don’t want to work hard at being good at it. (Similarly, ENTJs hate worrying about peoples’ feelings and they tire of working hard at it.)


  19. Coach Oz
    Coach Oz says:

    Thanks for the guest article Cassie. I like your point one about showing how you can improve the bottom line. Very important to show during the interview if you want to get a job.

    Coach Oz

  20. Alan
    Alan says:

    You are going to hate this, and people are going to pile on me for this, but PLEASE don’t spell “every day” “everyday”.

    Please don’t. Jesus God Almighty please don’t. Please.

  21. Brittany
    Brittany says:

    I don’t really “get” this post. What about this partnership is a good thing? Though it sounds like you are happy… maybe that’s what is good. Some people need challenges to sort through to feel alive. Myself? I prefer my challenges in a different form, but hey, that’s just me. Cheers!

  22. noi that
    noi that says:

    I worked for a crazy lady a couple of years ago. Small company – but this lady lived large claiming she was raking in dough. She also drank like a fish and constantly screamed at everyone. Very stressed about success and money (and paradoxically very impressed with herself at the same time).

  23. Eric
    Eric says:

    I really don’t get that one I have to say.

    An entrepreneur who is hiring people to do the stuff they cannot do is understandable.

    An employee who does the same ? Err… I don’t follow.

    I am a Head of Department and I have the opportunity to hire someone to help me. But this position didn’t come up because I am bad at what I am doing but because the workload is becoming rather huge and there is a limited amount of hours in a day.

    So of course, since I have the opportunity to hire someone to help me, I will make sure that person is good where I’m weaker. But being weaker doesn’t mean not knowing how to do something and most important of all, this is a luxuary, a cherry on the pie and not the main reason for hiring.

    If the main reason for hiring is that I don’t know how to do a certain part of my job, I would be fired and replaced by someone better.

    I don’t mean to be rude but sounds like a waste of money to me.

    So no, an employee who’s hiring someone to do a part of his job he cannot do, I do not call that a “Genius”. I call that lazyness or being at the wrong position.

  24. Mia
    Mia says:

    I just randomly came across this article googling content on managing up and was captured by the narrative. This was so beautiful. Thank you for sharing.

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