What good mentoring looks like

This is a guest post from Cassie Boorn. She is 25 years old, and she is a social media specialist at a large public relations firm. She is also a single mom to a six-year-old son, and they live in a town in Illionois with a population of 2000.

I read Penelope’s blog posts about abuse and bulimia and failure and oral sex and I wondered if I could ever be that brave. I built my career by becoming friends with big bloggers, and I decided I wanted to make Penelope my friend.

So I hired her for a career coaching session because I knew if we talked on the phone she would remember me. After that I just kept emailing her links to stuff I thought she would like and pitching her for projects I was working on.

She hated all of the projects I pitched her.

Then I started sending her business ideas. I would send her an idea, we would get on the phone and she would tell me why my idea wouldn’t work, and then she’d end up giving me career advice.

Actually, she would just tell me I need to move out of my small town because I must be miserable there.

I was certain that I wasn’t miserable and because I make more than almost anyone in my town, and I work from home so I can be with my son.

Here is the part where I tell you why you need a career coach — it is impossible to recognize the difference between being comfortable and being stuck unless you have an outside perspective.

Here’s my day: I wake up and go right to the coffee pot while I tip-toe around the house trying not to wake my son. I brush my teeth, decide to not take a shower, put my hair in a ponytail, and walk to my office to start working. My son goes to school and then watches movies in his bedroom while I have conference calls. I tell him I will be done working at 4:30 but I don’t leave my office until 6:00. I think about what to make for dinner and pretend to be cleaning the
house but really just walk from room to room bored. We play a game, I give him a bath, tuck him in and grab a beer. I normally start working again or sit in front of the TV with more beer or sometimes I eat and eat and then throw up because bulimia doesn’t stop when you have kids.

I did this every single day and planned to until I was 36 and my son went to college.

Eventually I agreed with Penelope that I might need to move. Mostly out of fear of  telling her no. Penelope fixed my resume, and I looked at apartments in Chicago and started to realize how miserable I was and I got really sad at the life I had been living for the past two years.

Here is the part when I tell you about me being gay. I have known I was gay for a few years but was too scared to talk about it. I didn’t tell Penelope because I planned on moving and then meeting a girl and then I’d tell Penelope. I didn’t want to deal with it now.

Then I met a girl. I thought it would end quickly and life would go on but two weeks in I had put a bazillion miles on my car visiting her and wondering what I was going to do about moving.

I got a job offer and they told me I could work from home and I thought how perfect that would be because I could move to Peoria and my girlfriend and I could live together with her son and my son and OMG MY LIFE IS SO GOOD.

Except I didn’t tell Penelope any of this because I hadn’t actually told anyone I was gay, and I was too scared to tell Penelope I wasn’t moving, so I avoided the topic.

If you have read this blog for anytime at all you can imagine how well that went. Penelope called me every day to talk about moving. Every. Day.

One day I got enough courage to talk to her about the idea of me not moving and I said I might have a better plan than moving to Chicago. What if I found a place closer to home but bigger than where I currently live? What if I moved to Peoria?

Direct quote: “Do not tell me ever again that Peoria is a good alternative to Chicago. Not ever.” Then she asked if I was joking and I wondered how I was going to tell her because I wasn’t sure how she felt about gay people or gay marriage or any of that and I was afraid she would hate me.

Penelope called me at 6:30 in the morning one day with a solution, “I think you are a big-picture person and just scared of the details so I am going to help you.”

It was then, at 6:30 in the morning, that I realized she wasn’t going to give up on the idea of me moving. So I told her I fell in love.

She was so happy for me.

Then I told her I was gay.

All I could hear was screaming.

She was pissed. Livid. She had just spent six weeks calling me daily and worrying about getting me to Chicago while I had hidden something so big and so integral to who I was that she felt like every conversation we had up to that point felt like a lie. She was pissed that I had assumed she was so judgmental and hateful that she would care that I was gay.

This is the part where I give you career advice. You can’t hide who you are and make genuine connections at work. Eventually it comes out and you make everyone around you feel like they have been duped. If you want a great career you have to have a good network and you have to have good mentors and people can’t mentor you and be your network if they don’t know you.

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  1. christy
    christy says:

    Cassie, first congrats on finding love. I hope happiness comes next.

    I get the fear. Really.

    I have a giant crush on Penelope, which really got going when she tweeted something like, “I should be a lesbian so that I can have someone to give me fashion advice when I get dressed in the morning.”

    I responded something like, “Wouldn’t work if you were with me. Clothes are something you put on to avoid being arrested.”

    She followed me because of the reply.

    I’ve been saving pennies to afford career coaching from her. I respect her perspective. Good to know it works.

  2. Harriet May
    Harriet May says:

    That is so smart. I mean hiring Penelope, not not telling her you’re gay. I mean, I’m not gay so maybe I don’t know. I do know that my best friend from college is gay, and she told one of our mutual friends first and I was so pissed. I’m 25 too and lost and living at home and working for my dad and I hate it. I feel like I should be learning more about myself and my strengths and growing my network but I don’t feel like I’m doing any of that, so instead I’m taking free online courses on history and startups and hoping I get my American citizenship this month and feeling like poison but hoping it works all works out eventually.

  3. Erica Peters
    Erica Peters says:

    Please edit the last line. It should say something like: ” If you want a great career you have to have a good network and you have to have good mentors and people can’t mentor you and be your network if they don’t know who you really are.” Or something like that. But I want to know how Cassie ends that sentence.

  4. Elizabeth
    Elizabeth says:

    So I know this wasn’t meant to be a comedic blog post, but I laughed. I’ve only ever read Penelope’s blog, and I don’t know her or you, but I laughed at the scene I envisioned with her screaming at you on the phone. This post also validates my behavior of telling people all about my life (which is not nearly as interesting) even though it irks my less openly-sharing husband and friends. I can now say, “Well at least you can’t claim I ever lied to you or kept secrets.” Although I am sure some of them often wish I had…

    Good luck on your move. Go get what you want in life.

  5. Vigo
    Vigo says:

    Nothing like paying a psycho for career advice. You two idiots are perfect for each other — i know, why don’t you start a business together!

    • Kate
      Kate says:

      Indeedy. Nothing quite as sad and pathetic as someone who returns to a blog written by someone they claim is stupid.. to berate them. .and then berate more people they claim are stupid.

      I believe Mr Gump said “stoopid is as stoopid does.”

  6. Kate
    Kate says:

    Good for you! I wouldn’t worry about telling people you’re gay. Gay is easy. I speak from experience as a 20+ year bisexual. Us bisexuals are really weird, I actually lie and say I’m gay sometimes as its less confusing and therefore, not weird for people. So you’re good to go! Good luck in all you do =D

  7. My honest answer
    My honest answer says:

    Hands down the most sensible and informative thing I have read on this blog for months. Good luck with the move (if you decide to go for it), the relationship, and your job prospects. And thanks for sharing. It’s not as awful as you imagine, right?

  8. Irving Podolsky
    Irving Podolsky says:

    Dear Cassie,

    I think your story is incredibly touching, mostly because you have “come out” in so many more ways than your sexuality.

    I agree with your advice about being genuine at work, which I believe also applies to any sincere relationship.

    And yet, allowing personal exposure is a complex deal. Generally speaking, it’s productive. But there are people who would not respect your honesty nor protect your vulnerability, or even want to understand it.

    I think we know who those fearful people are and just how much we can rock their world with honesty before it gets ugly.

    I for one must learn to respect my friends and family (at least to some degree) who align with the other political party and are fearful of gay marriages and pensions for teachers and firefighters, and health care for all, and the list goes on.

    You see, it’s not THEIR opinion of me that’s in jeopardy. It’s my opinion of THEM. So rather than challenging their beliefs that could quickly build resentments, I choose to avoid certain subjects.

    Is this dishonest? To some degree.

    Is it practical? TO some degree.

    Is it something I feel comfortable about?


    So Cassie, I’m with you. I’m not gay, but I AM a screaming liberal. And lots of times I have to keep that closeted up! (I’m just glad I live in LA!)


    • thatgirl
      thatgirl says:

      I agree with most of what you’re saying, but the nuance here is that Cassie and Penelope are talking about their mentoring relationship here, rather than a workplace (the absence of which makes any oversharing pretty moot).

      In a one-on-one, mentoring relationship, particularly when one is looking for guidance on the intersection of their life and their life’s work, personal details do make all the difference to the quality of the potential advice!

  9. she wins
    she wins says:

    How much does your past play a role in who you are today and what you share with mentors? Where do you draw the line? Do they need to know that you are intermittently suicidal and have a history of heroine abuse? Or is that TMI? I honestly have no idea how I hold it together, working in a cubicle with people that never really say or do anything controversial at all. Your blog content is amazingly honest. I cannot relate to the way they were raised, their life experiences, and am not able to share my stories of growing up b/c they are so extreme in comparison.

  10. TD
    TD says:

    A great mentor sounds like a wise, accepting and really motivated friend, at least in this story. I suppose the best thing a mentor can do is reveal our blind spots and show us other possibilities. Amazing post.

  11. Robin
    Robin says:

    Hi Cassie,

    You sound like a smart woman. I’d like to echo all the positive things people have said to you already, but add one thing: It is way to early to live with your girlfriend, especially with kids. You should move NEAR her and develop your relationship before you live together. Good luck in Peoria.

  12. Caryn
    Caryn says:

    You’re brave and strong and I’m so thrilled things are going well for you. Best of luck with fixing those things that need fixing as well.

  13. Evy MacPhee
    Evy MacPhee says:

    This is timely for me.

    I am 65 and mostly considering how to live the rest of my life.

    I have been hiding for the last six years. I am considering that possibility of not continuing to hide, on a selective basis.

    Evil people sometimes have children. I am one of those children. I make a conscious effort to be a good person. However, the first 19 years of my life and particularly the first 12 years of my life have the footprints of that evil all over them usually called “extreme sadistic child abuse” or something like that by professionals.

    I do have friends, not nearby, but good friends.

    This blog post made me think. I am not sure what my thinking will be later. I am thinking.

    Congratulations on coming out!

    Congratulations on finding someone to love!

    Luck and abundant blessings upon you both and your children.

  14. Miss Britt
    Miss Britt says:

    I love this post for all of the previously stated reasons, which generally means I just wouldn’t comment, but it was too good not to add my pithy “me too”.

  15. Rich
    Rich says:

    Unlike so many that have posted on this site, this post makes no sense to me…
    It seems like a list of problems where you engaged a professional career coach and then basically jerked them around. Perhaps more importantly, I don’t know how you could read P. Trunk and think that she would care whether or not you were gay.
    And you aren’t moving because you are gay, you are moving and abandoning the right career decision for love. Thousands of people do it every year. Just look at the factories on the river in Peoria, a lot of them work there.

    This is the part where I tell you to stop congratulating yourself for discovering that being honest with the people that can help you is a breakthrough.

    • Passingby
      Passingby says:

      Agree with Rich.
      And this is the part where I tell you to develop your own writing style. This post seem written by the owner of the blog.

  16. @BarbaraJones
    @BarbaraJones says:

    Cassie I’m sure this was not easy for you to write i adore you and I’m so very proud of you and happy for you and all the other ‘for you’s I can think of. You deserve so much happiness and I’m glad to be your friend! Xoxo

  17. Ruth Zive
    Ruth Zive says:

    Great post and congrats!

    I’m not gay, and I’m usually practicing Ashtanga yoga at 6:30 am, and I did get an office away from home so that I wouldn’t have to feel guilty when my kids spent far too much time on their computers and televisions…


    I want Penelope to be my mentor. I think I might sign up. This was a great endorsement.

  18. Jill
    Jill says:

    Cassie–good job, lady.

    And, come on…Peoria stinks (sorry, Peorians) but I am so glad you unboxed yourself out of that corner.

    You made me a fan today and I’ll keep reading.

  19. Mark W.
    Mark W. says:

    I can “see” it now … Penelope going ape sh*t and bouncing off the walls when you told her you were gay. It’s no surprise to me. She has written on previous posts her disdain for secrets. It’s a secret that would matter in her advice to you. There used to be a tagline to this blog that went as follows – advice at the intersection of career and life (or something very close to that). I can’t imagine her giving you advice about your career without it including life advice. The advice on both fronts is intertwined and inseparable. While I was reading this post about your mentoring with Penelope, I thought of a lawyer-client relationship. The lawyer can only help the client to the extent the client is willing to be open, truthful, and willing to share all the details. I think the same can be said about a mentor-protege relationship. You reap what you sow.

  20. Abigail Gorton
    Abigail Gorton says:

    Funny… Just today I was talking to my gay, married, friend, bookkeeper and referral partner (get it? She ticks all those boxes in my life and my business). She wears a wedding ring but said how she hates when anyone asks what her husband does. That she doesn’t want to get into a whole coming out speech in what for other people would just be a casual enquiry near the start of a business relationship. I asked what else she expects us to ask and assume? If gay people are 3% to 5% of the population, then it’s 95% plus likely she would have a husband rather than a wife. Even in San Francisco, where we live. Maybe the answer is a knowing smile and the statement “Well my SPOUSE is a ______” because, yes, people do build relationships as they trust each other with the truth.

    • Michelle
      Michelle says:

      Abigail I’v answered the question that way – “My partner / spouse (insert her classicly feminine name here) works…..” for almost two decades. It works well for all involved. In the 1990’s I made sure to keep the conversation moving, to give people time to let the information sink in. Post- “Will and Grace,” and “Ellen,” that’s rarely necessary.

      I hated “having to come out” especially whenmore likely than not the woman who asked me the question would resent me for her feeling uncomfortable with the answer. And it was – is – always straight women who ask me personal questions within the first few hours at a new job.

      I’m glad I stuck it out: for the sanity saver of being true to my self; for loving and in being in good company with the company I keep; and for the priceless capacity to suss out my true north, one awkward moment at a time. Totally worth it.

  21. Alexis
    Alexis says:

    Does it seem strange that Penelope was so intent on your moving to a big city, when she herself lives in a small farming town?

    • Sara
      Sara says:

      I think that would only be strange if Penelope had never lived in a big city herself. It was only after spending years in NYC, moving to smaller (but still city) Madison, and then falling in love did Penelope actually move to her small town. When reading this post I was thinking about that progression, and how easy it is to be overcome by fear even when we technically know the other person would understand (aka moving/staying in small city for love) because they had done it themself.

  22. Matthew Egan
    Matthew Egan says:

    I really really loved this post. I’m reminded of something that Elizabeth Warren said during the DNC and I think it applies here. She was going on about how the system is rigged and ordinary people were setup to fail. This is an excellent example of how that simply is not the case, gay, straight, or otherwise.

    All we have to fear is the fear, truly, the fear of sharing, the fear of being judged, the fear of failing. There isn’t actually a Boogy Man out there trying manipulating things, but creating the fear of that allows a lot of people to make a lot of money.

    It reminds me of a Scott Stratten quote, he said “There are more people selling the dream than there are pursuing it.” That applies here as well, don’t let your fear stop you from pursuing your dream, and ignore the haters…

    …just like Penelope does.

  23. Rachel Gross
    Rachel Gross says:

    Great post Cassie! I try so hard to keep my cards close to my chest, and my last job review showed it. My boss told me I did a great job at my J.O.B. but I didn’t get involved with the culture and community of my office. In order to turn around my reputation I spent last winter bringing in baked goods weekly (I mostly work with young male surfers). It paid off, I am part of the crew (as the sole female) and while I may not be invited to every party I am invited to lunch and people are interested in me and my life.

  24. Andrea
    Andrea says:

    Pfffft of course Penelope isn’t homophobic. She’s far too interested in the vagaries of human sexuality to get all knee-jerk about that. She also knows that the “straight” world is not as homogeneous (if you’ll forgive the term) as it seems…And she’s also tried sex with ladies. Well, lady.

  25. cj renzi
    cj renzi says:

    Now that is a Brave New Post. Holy cripes, that ought to get people to show up as themselves if they were not before reading it. May much good come to you from making such a valuable and authentic post. Oh, and there was some very good, subtle humor in there too. Well done!

  26. Laura
    Laura says:

    1. I can relate to Penelope’s reaction. My best guy friend in high school told me he was gay after we graduated. I was pissed, mostly because I thought we were both going to get married (to other people, not each other) and raise our children together, and the fact that he had no intention of doing that and never let on made me feel betrayed because we never kept secrets from each other. In retrospect, being gay in the 70’s wasn’t easy for anybody whether you were the person who was gay or the person who didn’t know what the hell to think.
    2. This is a really funny, touching and honest post. It made me happy for you that you fell in love, and I don’t even know you.
    3. Back off from the mentoring. You sound a little bit like Penelope in style and tone. Take her advce and run AWAY with it!

  27. Dusti Arab
    Dusti Arab says:

    Not going to lie, there isn’t much that’s funnier or more informative than Penelope ranting. A couple months ago, through a couple connections I somehow got her on the phone for an interview that quickly turned into the best career advice I’ve ever gotten.

    Penelope, I owe you a book. The Kickstarter to pay you to grill my ass over it starts Monday.

  28. Bethany
    Bethany says:

    Hi Cassie – I enjoyed your post and willingness to put yourself out there. Good luck in your new relationship and adventures. My only suggestion is that you should keep exploring and developing your business ideas. While they may not be exceptional yet – one day they will be. You’re clearly on a role with taking risks and living life so keep going. It will be interesting to see where you end up.

    Best of luck to you

  29. Zee Stylist
    Zee Stylist says:

    As soon as I read “guest post” I became very skeptic but boy was I wrong. I’m also inclined to comment because it was a spectacular post. Took me on a journey.

    Love you Penelope!

  30. Liza
    Liza says:

    I am wondering why none of the commenters are concerned about your bulimia. I understand the support for a big change and moving, being gay… But bulimia is a serious issue.

    You practice bulimia for your own reasons, and I’m sure stress or vulnerability play a role in why you do so. If/when you move and get a different job, I hope you are able to seek the help you need to deal with this. Otherwise, it might get in the way of your happiness.

    We all want happiness, and yet, we all manage to get in our own way sometimes. :)

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