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.