Baring it all, in business?

A few weeks ago, I received an email from a guy I went to high school with — you may remember him as the guy who wrote this email about me. To make a long story short, it’s a guy I had a massive crush on for years, but for some reason he was terrible to me.

Because of my A. faith in people and their ability to change, and 3. my wavering level of self-confidence, we have kept in touch over the years, though I haven’t seen him in about 10. A little more than a year ago, I stopped communicating with him because he often made me feel bad about myself.

He’s made it clear that he thinks my career is a joke, my life is boring, and he’s got no problem bragging to me about how great everything is for him.

Enter: the email. It was formally written, as he said he knows we’re “not on good terms,” but he was in a position to hire a writer and thought of me (not sure why, but whatevs). He described the project as lucrative.

He also said he hoped that this business deal would somehow mend our friendship, but if I told him to “fuck off,” then he would understand.

After thinking on it for a day, I replied to him, touching on only the business matter at hand. I’m always looking for more, new writing work, so if in fact his proposal was legit, then let’s play ball.

I heard from him a few days later, On Valentine’s Day, via text, saying he was still working out plans on the writing deal.

Then, he started sending me a variety of photos that I wasn’t really sure what I was looking at: various office pictures of some sort, of dogs under desks, people sleeping in weird places, and motivational sayings taped to a glass wall. I didn’t reply.

Then he asked me if I was single for Valentine’s Day, but I had fallen asleep.

When I woke up the next morning, he’d sent me another picture. It was one I’d sent him 10 years ago — a topless photo.

He’d sent a text along with it, “I’m single too, but I still have this to look at, get off to, and help me sleep.”

My stomach churned.

I remembered that I’d sent him the picture — not a smart move, but at least my face wasn’t in it — you could even see my dorm room behind my bare chest.

The picture, of course, made me mad. How many phones had he had since then, and he felt it necessary to save the picture on each phone? But the photo also made me very sad. It was a sign of my past — a time when I did a lot of things to either please people, or get their attention. And for years, I desperately wanted his attention.

I wrote him back and told him that all at once, I remembered why our friendship was over, and that I was no longer interested in the business deal.

I’ve been thinking a lot about my past lately (read last week’s column for further proof), and although I’m getting better at making sound decisions regarding my emotions, it will always be a working journey for me.

The fact of the matter is, as a dating columnist and blogger, there are a lot of people out there that know things about me, that they wouldn’t know otherwise. Most of the time, this doesn’t bother me at all — until I want to get a “serious” writing gig.

I get nervous when I make a pitch — afraid they’ll Google me and see the secrets I’ve shared, that Playboy audition, or my weaknesses in finding a decent man — I’m afraid they’ll judge me; box me in as a fluff writer and call it a day.

I will probably suffer from that battle until I find a job (or jobs) that celebrate the entire me. But that’s the struggle any creative finds himself in. Every blog, every article, poem, one-liner, painting, collection… it’s out there to be judged by those who know nothing of the sort.

That is the risk we take, in order to fulfill our passion.

While I’m not proud of that picture I took 10 years ago (it wasn’t my last, but let’s be real), I can only be proud of the moves I’m making today — the ones that don’t involve the toxic people, in life and in business.