Taking the Next Step - Goals and Challenges

I know its a cliche but I love a fresh start. I love being able to begin again, I love starting over. I love a challenge, I love setting goals.

I love taking the next step. In stilettos, naturally.

It doesn't seem like that long ago when I would go to the mall and avoid glancing over at the lingerie sections of a department store lest someone figure out my secret. I am not sure when I found the courage to do so, or where that bravery came from, but one day I bought a pair of panties and never looked back. I never thought I would do anything more fearless than that, but fast forward a decade (or two) and, well, here I am.

I look at my photos and I look at my wardrobe and it all looks so easy. These days I never think twice about walking across a parking lot to a salon for a makeover. Strutting through the mall in four inch heels? Easy peasy. Bra fitting? No problem.

But what's next? Ten years ago if I looked at what my life is like today I would have thought I wouldn't want anything more. As I become more confident and comfortable living a double life (if you will) and having two gender identities, I've wanted to do more "everyday" things. At one time going out en femme meant visiting a LGBTQ+ bar or a drag show. Then progressing to a coffee shop owned by a trans woman. Soon I was attending support groups for transgender women. Going out en femme meant going to places where a girl like me wasn't unusual. But after limiting myself to these types of places for a while I began to grow restless. I wanted something new. My confidence grew, I was comfortable being out in the real world, and I wanted to experience more than what I had already done.

I started to list all the places I would go if I were brave. Shopping at the mall, getting a makeover, that cute store in Minneapolis that sold amazing dresses, having coffee, going out to dinner. And then one day in June... I just did it. The first time I went out en femme during the day was an experience I will never forget. Too excited to sleep, I woke up early and got dressed. I wore a cute pastel tank top, a black cardigan, a skirt with a floral pattern, black stockings, and black stilettos. As nervous as I was, my eyeliner looked amazing despite my trembling hand.

Before I had a chance to talk myself out of it, I was in my car and on my way to a coffee shop. I drove about twenty miles away from where I lived to hopefully avoid anyone I knew. I parked my car and walked about two blocks to get my coffee. I will never forget the sensation of my heels on the sidewalk, the wind through my long, black hair, the rising sun warming my body. It was a new day... in more than one way.

I took a deep breath and walked through the door of the cafe. The baristas smiled at me... and it was sincere. I ordered my coffee, gave my name(!), and waited with the other early risers for my latte. After getting my coffee, I realized I had accomplished something amazing. Yes, this was something I did many times in male mode, but this.... this was different. It was a high heeled step into another world.

Bursting with pride and confidence and acceptance, I walked into the small upscale grocery store next door to the cafe. My heels clicking on the floor, the clerks looking at me (but not staring at me), and everyone (including me) just going about their day. It was bliss. I had been so afraid to do this, but strolling through the produce section of a grocery store on a Friday morning felt like a new beginning. I was afraid of people staring, rude comments, pointing, harassment, and worse. But it was a beautiful morning.

Bolstered by the uneventful moments, I decided to make my early morning coffee run into a day of running errands. By the time my day was over, I had visited two malls, two large department stores, more coffee shops (not that I needed more caffeine) and had lunch. I returned home just... glowing. I felt like I had climbed a mountain. I had crossed so many things off of my wish list that day but as the days and weeks passed, I dreamed up more things I wanted to do. And eventually, one by one, I crossed those off my list. Museums, plays, lingerie shopping, dinner at expensive restaurant, Pride festivals, photo shoots...

But as the new year settles in, I am started to daydream once again. What's next? What is left on my wish list? I would love to be a bridesmaid at a wedding. I would love to attend a fancy gala. I would love to fly and travel en femme.

These days I feel I have the confidence to go anywhere en femme. The goals listed above are things I'll do, but just haven't gotten around to doing. These dreams feel... easy. But I love a challenge. I love to push myself in many aspect of my life, and half of my life is the life I have en femme. The idea of going through airport security and hopping on a plane and going to a new city feels like a breeze compared to other goals I have, namely my immediate family knowing me. All of me. Both of me. I have come out to my mom and siblings, but that was years ago. I wasn't who I am then. It's true you can only come out once, but as my gender identity evolves and as I understand myself (and herself) better, perhaps coming out again is the next challenge.

What are your goals for this year?

Love, Hannah


  • Shawna

    Hi, Hannah! It's like you've been reading my mind! Although there are many things yet to scratch off my major "to do" list, my main goal (for 2020 and beyond) is to enjoy being a woman! The biggest step for me so far this year, has been to join several woman's groups on Meetup. NOT LGBTQ groups, but groups started by women for women…social, professional, etc. And guess what? ALL have welcomed and accepted me without reservation, and now (like you) I'm able to begin to feel FREE about who I am!


  • Kevin

    Amazing! This was the boost I needed, this is the life I’ll be living soon! Thank you!!

  • Jayne

    I too have advanced my enfemme lifestyle to the point that I just naturally get up every morning, get dressed and go about my normal daily routine. I go shopping, out for lunch, to the salon to get my nails done. A Body Revive treatment starts the spa.
    I think about how great I look in a skirt, blouse, and heels. Love it when the cashier greets me as:
    “How are you today Ma’am?” I is sooo fun living as a girl. My life with my wife has never been better. We now do everything together. We are best girl friends.
    Love all your blog comments.

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