Supportive Coaching Program
Guidance for the Woman You’re Becoming
You don’t have to navigate this part of your life alone. Whether you’re just beginning to explore your feminine self or trying to take your next meaningful step, Annaliese provides a private, supportive space to talk openly and move forward at your own pace.
Maybe you’ve carried this part of yourself quietly for years. Maybe you’re ready to express her, but you’re unsure how to begin or who you can trust.
Annaliese’s private coaching gives you a safe space to be heard, supported, and guided with care — from navigating relationships and finding community to building confidence in your feminine presentation.
Why Coaching?
1. Explore Your Feminine Identity
Get support with the early steps of feminine expression, especially if you are not fully out or are unsure where to begin.
2. Build Confidence and Self-Trust
Develop practices that help you feel more grounded, feminine, and confident in who you are becoming.
3. Plan Your Next Steps
Work through relationships, family dynamics, living situations, and practical decisions with steady guidance.
4. Integrate Your Feminine Self
Create a realistic plan for expressing yourself more fully in your work, relationships, home, and everyday life.
“Before our outing, I was continually wavering on my transition. I didn’t think I could do it. However, with Annaliese's supernova-bright personality, impossibly inspiring positivity and incredible sense of personal style, she changed my life in one afternoon! It’s not just because of the clothes she helped me find, those were great, don’t get me wrong. It’s the way she helped me find Caragh for the first time that still makes me cry when I think about it."
—CARAGH
Annaliese understands that this journey is deeply personal. Whether you have always known there was a woman within you or are just beginning to explore that part of yourself, she offers a safe, supportive space to be seen, heard, and guided with care.
With experience supporting the LGBTQIA+ community since 2002 and trans women since 2016, Annaliese brings both expertise and heart to every client relationship. Her work is centered on helping you build confidence, self-love, and a more authentic expression of who you are.
Interview With Therapist Dr. Z & Annaliese Cherry
Coaching Testimonial
I reached out to Annaliese after reading about her in the Huffington Post
The article mentioned how she lovingly coached Caragh out of the closet. I too was isolated deeply in the closet, and at my age, wondering if transitioning was even feasible. Complicating the situation, my partner knows I am trans, is unsupportive, and does not want me to transition.
Annaliese became the supportive friend I needed to move forward. She helped envision a future me I’d like to become. Most importantly she helped with the confidence to try.
We begin with her sending clothing and a wig ideas, then moving into her coaching program. Since working with Annaliese, I joined a Transgender support group, consulted a lawyer for a fair relationship resolution, sought help from my coworkers, and now actively planning a new life in a transgender friendly state. It’s never too late to become who you want to be!
Thank You Annaliese!
Stefanie. XOXO
" Annaliese has an extraordinary ability to listen deeply and empathetically. She creates a safe space where I feel comfortable sharing my goals, challenges, and aspirations. Her encouragement is always unwavering, and her belief in my potential gave me the confidence to push past my limits."
-Finley
"Annaliese truly made me feel like the person I am, Being mature (over 50) I thought my time had passed to be able to express who I really am! After my initial consult with Annaliese, I felt comfortable to plan some time with her. I cannot express how liberating it was to have someone to guide me and support me as I go on this journey. Thank you Annaliese for your kindness and empathy."
—MARNIE
What You'll Receive...
1. Receive support and ideas to nurture your femme self when you’re not fully out
Allow yourself the pleasure and ritual of feminizing. Step in further into the women you are with customized hair, makeup, and clothing selected just for you.
2. Tap into your feminine intuition and the feminine divine
Awaken and activate your inner feminine essence with meditative self-care practices to elevate you and align with your soul's deepest desire.
3. Navigating personal or family relationships as you come into your true self
I help navigate your personal relationships, and organizing next steps—like new living situations, complete with decoration of your new space!
4. Fully stepping into you!
Guiding you through the integration of your fem self in work, relationships, and family.