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. Heather Salvador
    Heather Salvador says:

    “Pissed…I had assumed she was so judgmental and hateful that she would care that I was gay”
    I am troubled by the exchange that unfolded when Cassie came out to Penelope. It reads as if Penelope was happy for Cassie until she found out that her love was for another woman and then accuses her of dishonesty and misjudging her. Penelope’s response says more about her own internal conflicts with honesty and relationship-gender bias than it says about how Cassie should approach her business relationships. Cassie was met with shame from Penelope about lying to her, as if she owed Penelope a level of honest that she had not given to another person in her lifetime. In reality, it is not dishonest to fail to change another person’s bias in case it has an impact on which emotion that person experiences. The fact that the gender of Cassie’s love interest changed from Penelope’s assumption of hetero instead of homosexual should have been of no consequence to the advice she had been giving. Coming out should never become a shaming experience for the (gay) person. Penelope needs to look inside and find out why she was triggered by Cassie’s experience instead of trying to force Cassie to stop “making her mad” by learning to be “honest” about personal matters that are unrelated to a business relationship.

  2. lipsome
    lipsome says:

    Yikes; slow down. I second the advice of an earlier poster who said to move near your new love. Please not in with them when kids are involved. At least until you know them much, much better.

  3. Dave
    Dave says:

    Cassie, great post. One thing you don’t lack is confidence. Convincing Penelope that Peoria is a fine career alternative to Chicago would be akin to goading Rush Limbaugh into endorsing Barack Obama!

    Give ’em hell, Cassie!

  4. mf
    mf says:

    One might question the wisdom of a bulimic selecting a mentor who has a history of builimia, not to mention open hostility towards “fat” people.

  5. Amanda
    Amanda says:

    This is a great story and a gorgeous post starting with the adorable picture of you top and center. Thank you for sharing your story.

    I’m just wondering how many career coaches and possible mentors you spoke with before you found Penelope? And once you spoke with Penelope how did you know she was the right mentor for you? I’m asking because I’ve spoken with career coaches before and although the advice was ok, I never felt a connection.

    Additionally I’m asking because I don’t give myself away in one conversation. I’m a very private person and as an INFP I don’t do well with sharing feelings. Should I be giving the mentors I’ve spoken with more of a chance or should I be looking for one who I immediately click with?

    Now that I feel like I’m writing into a love advice column I’ll end it there. Thanks again for the wonderful post and good luck to you!

    • Cassie Boorn
      Cassie Boorn says:


      I have worked with a number of mentors and career coaches both in paid capacity “I hired them to coach me” and unpaid capacity, “we were friends or colleagues and they organically became my mentors.”

      I would start by establishing a mentoring relationship with someone you know personally and feel comfortable with. If you have a colleague or supervisor or even a friend that works in a another field but might be more senior than you. If you are comfortable talking to them about personal issues they could be great professional mentors. The least awkward way to do that is simply to set up a monthly lunch date and say you would love to chat about career/business stuff once a month in a mentorship type way.

      Once you identify what skills you are lacking or what parts of your career you need to focus on, I would suggest hiring a coach that can help you with those skills.

      I am generally uncomfortable with people who have really strong personalities and are outspoken. One of the reasons I have always wanted to work with Penelope is to help me learn to be comfortable around people who make me nervous. Once you have a good foundation of self-knowledge you can pick coaches and mentors that will help you get where you need to go.

      Hope that helps!

  6. Karen
    Karen says:

    Cassie — Congrats on “coming out.” Congrats on “coming out” on Penelope’s blog too. We all have something to come out about, I think. This is the joy I get from reading Penelope’s blog. She is so “out” about Asperger’s. Strangely, I am more fascinated by the fact that you are a single mother at 25 than a gay woman. As a married mother of one (with a hubby who is a supportive father), I applaud your personal strength for that! You just mentored this old lady with that one personal fact about your life.

  7. for give me
    for give me says:

    You know I have a best friend who was a great worker who lost her job. Because of her personal life outside of work ….which isn’t fair …she was my best worker .we worked in a school cafe and served over 400 students a day for lunch ….but my boss heard that her and her husband lived their lives as I guess you would say swingers they both had other partners …im not saying tis right .but it had nothing to do with her job performance…..but my boss fired her to get rid of her because of her personal life style……same as some people do if your gay……so people dont tell their gay or swingers ect…….thanks ……just saying

    • for give me
      for give me says:

      I forgot to say ….I was her boss we worked together but I left to advance my career and it was my boss over me who fired her …if I never left that job we both would still be working together today …….just saying

  8. Marci
    Marci says:

    Cassie, Malleri sent m this,what a great story. Let me know what you decide to do. Hope things go well with you and hope to see you soon. Miss the holidays with everyone you are like my 4th daughter Love Marci

  9. Spekkio
    Spekkio says:

    “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.”

    This sounds great in theory, but I worry about it in execution. Discrimination based on sexual orientation is legal in much of the United States. The common wisdom is that illegal forms of discrimination (age, gender, religion, disability, etc) still happen every day. And it’s also widely believed that filing discrimination complaints / lawsuits is almost always a waste of time and money since Corporate America has learned by now how to cover their tracks.

    In other words, just pulling a scenario out of thin air: a 55-year-old male with all the right qualifications and experience can be turned down not because of age, but because of his “salary requirements.” (Never mind that he didn’t give any requirements because his unemployment compensation has run out, his savings have run out, and he’s rather desperate for work.)

    I will admit to being an anxious and fearful person, but when I hear people tell me (or others in general) to “be themselves” and “be honest with others” and other such…well, it all sounds like heroic nonsense to me. It sounds like the pablum we load children’s minds up with – things like “hard work,” “dedication,” and “playing by the rules.”

  10. Denise
    Denise says:

    Great story and I absolutely agree a good mentor and supportive network is so important, as is being honest with them. However, I wouldn’t be OK with anyone screaming at me. There are ways to communicate your point with impact without doing that.

  11. Kashif S. Malik
    Kashif S. Malik says:

    Pardon me, but is it just me who feels that the post is rather shallow and a ploy at mentoring how-to; or, one’s sexual orientation is a peripheral issue when it comes to mentorship?

  12. merle
    merle says:

    Glad you shared your experience- I think you were fine on your own without someone telling you what to do, or how to live– listen to yourself… somehow this always works, and you end up on the right path–
    mine has always been, as I call it… Adventure Inspired.. from meeting my hubby, to coming up with my olovesm bag company..
    Good luck, sounds like your doing great, and things are working out–way 2 go!!

    • merle
      merle says:

      Opps, I did not mean being mentored was a bad thing, in fact, I need a business mentor!! But I think in your case.. it sounded like you knew what you needed to do.. and guess maybe the mentor was the one to help you move forward to do it… OK… what do I know.. I am learning everyday and loving it!!

  13. Person
    Person says:

    I know this might be odd to respond to an old post, but how do you let your personality, or who you are, show at work without offending people? I’m not the “right” kind of woman (introverted and tough, as opposed to extroverted, smiley, and fuzzy) and always find myself censoring and withholding myself out of fear I will piss someone off. Yet, on the flipside of that, I’ve heard in nearly any environment I’m in, that people don’t really know me, or that they feel I don’t have a “personality.”

    Is there a “right” way to express your personality?

  14. meredith
    meredith says:

    Where is the part where Cassie suggests to Penelope that she create online courses? finally Penelope agrees; she makes triple digit income and only gives Cassie Boorn a thank you note??? Does not sound good…Can we say A-hole?

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