Growing up, my parents were always there for me. Sometimes, it would seem, more than I wanted, I was trying to be more independent. But if I needed them to help try and figure something out, they were really good at that and their advice was sound and coming from a place of love and a genuine desire to see me succeed.

I could always ask their opinion on something I was either undecided about, or just didn’t know the answer. Frankly, I wished I’d asked and listened to them more not less. I lost my dad when I was 28. My mom followed him 5 years later. I am blessed for every minute I had with them.

The last 33 years, I was married and my wife took over the role of confidant although I didn’t confide “everything” (I told no one about my gender struggles) Her judgment and advice were almost uncanny in it’s quality and accuracy. I learned that if she said; “buy,” you buy. If she said; “sell” then you sell. Essentially her instincts usually turned out to be right (but not always) She could also help me talk things through.

It will be a year ago in December that she left me to move to California. (It’s late October as I write this) I don’t blame her at all. My being transgender turned her world upside down and she had every right to seek a happy life if staying with me was unacceptable.

This has left me feeling rudderless at times. Coincidentally, the hands down most difficult part of my life, (something few people experience at all) gender transition, coincided with the one time in my life where I have had to make every decision on my own. I’m finding that I sure as hell don’t have all of the answers.

What I have in abundance are questions, lots of them, and nobody but yours truly to try and figure it out. I’m navigating a vast expanse of uncharted water in a small boat and feel like it’s talking on water!

In fairness, I have one of the finest gender therapists available anywhere and she has been a lifesaver. She does help with major issues, mostly in helping me see the answer, but I see her once a month.

I spent 54 years learning how to be a man. How to dress, how to act, social responsibilities and the like. I’ve spent the last 15 months trying to figure out how to live as a woman, all while having no job or safety net. It’s been like trying to iron a dress while you’re wearing it.

It’s not that there isn’t information available, it’s that there is way too MUCH information available! Once you get past the basics, and most of us do fairly soon, there are seemingly millions of nuances. Being essentially isolated in an apartment doesn’t help. I really need to find work. My challenge is that I’m uber-qualified in my field; radio broadcasting, but being transgender, I’m also considered high risk and despite the major broadcast groups having clear cut anti discrimination policies protecting gender identity and expression, they also don’t actually HIRE any people like me to protect.

Outside of that, I am a relative fish out of water and am trying to avoid landing in minimum wage poverty. I’ve had it too good for too long. Just not as a woman.

I’ve written thousands of radio commercials and won a cabinet full of awards for excellence. I’ve helped dozens of people get jobs by providing glowing references. I can sell just about anything. I’m just plain lousy at selling ME.

Deep down inside, I believe I know the answers. People tell me all the time what great advice I give. But when it comes to me, I lack self- confidence. I can cheerlead all day for you, I just don’t cheer for me. Just writing those words is pissing me off! Why can’t I cheer for me?

Am I not worthy?

Of course I am.

I do have confidence in my ability. I have a long track record of success and friends spread all across the country. I just need that co-pilot every once in a while to remind me of those things when I get down on myself.

Oh and to also warn: “Watch out for that cliff!” That too.

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