On Your Mind | Wendy Cole | Transition Mentor


Transformation begins when we challenge our beliefs and courageously align with our authentic selves. Hear Wendy Cole, a transition mentor, as she shares stories of life-altering transitions, drawing from her own. As a born transgender, Wendy entered a world where societal norms clashed with her inner truth. Learn about the internal conflicts she had to face, and how her beliefs shifted to help her pursue her authenticity. She highlights the key elements of personal growth, including spotlighting the significance of challenging limiting beliefs, practicing mindfulness, and experiencing real-life situations. What she learned the most, however, was the importance of going through life’s transitions with courage and grace. Tune in now and give your authentic self a chance.

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Wendy Cole – Transition Mentor

Wendy Cole knew from childhood that she was a girl but yielded to family and societal expectations to fit in. At age 67, Wendy changed her life with her transition. Beginning in January 2015, she focused internally on accepting who she was, confronting fears, doubts, and anxieties that held her back for decades. She took the leap of faith to find freedom and joy in being herself. By 2015, Wendy was living as a woman. She had her long-awaited surgery at NYU Medical in 2017.

Knowing who you are and not being who you are is the starting point of every transitional situation. You know who you truly are in every aspect but the outside is what matters. That is what people see. Taking that first transitional step can be terrifying. It’s the stress of the journey, of the mental weight, and of worrying about the outside world. The physical transition is the easiest part. It’s getting through the mental transition that holds us back.

As a transition mentor, Wendy Cole helps her clients identify, explore, and eliminate the stress of facing life’s changes. Since 2017, Wendy has guided others through transitions. Her life experiences are the tools she uses. She believes in the mind’s powers. She practices mindfulness, shifting her beliefs, and energy work to support herself going forward, making profound changes in her life and health, and finding joy in being.

Wendy, welcome. Thank you for joining me.

Thank you, Timothy. It’s great being here.

I was hoping you could start us off by telling us a little bit about how you got into the work you do and what drives your passion for it.

I got into this work through my transformational changes, which I started in 2015. I found by 2018 that I enjoyed helping other people go through the same process. I was born transgender. My whole mindset from childhood all the way through was formed with the belief that I couldn’t do anything about it. I was told by age ten that I needed to repress everything I felt. Otherwise, I would be committed and fixed. Those were the exact words from my parents after five psychiatrist visits.

In 1970, I was told something similar by a psychiatrist. As a result, I also discovered at the same time that doing what I felt I needed to do, changing my gender and sex, would have left me with no means of living within society. I repressed that until late 2014 or early 2015 when I discovered that how I was born was categorized initially as a psychological condition with no treatment and no cure had been changed in 2012. It was changed to a medical condition that you’re born with and it’s treatable by hormone replacement therapy and any necessary surgeries.

That started my journey in 2015. I found a therapist that I connected with. I spent the first six months of 2015 working on changing my mindset. I had been repressing myself and everything for decades. I needed to change my beliefs in what was possible for me, align myself with my inner being, and get to a point where I could do this and not be afraid to do it.

When I started living as Wendy in July 2015, I never looked back. I have never been so happy and fulfilled. It made such a huge difference in my life and my personality. I became very social. Everything changed for me. It’s been a wonderful journey and experience. I practiced mindfulness, a lot of different types of meditation, and visioning. I would form a vision of small things that I knew I needed to do.

One of the first times I went to therapy myself, I made a decision on the way that I was going to stop for coffee at a Dunkin’ Donuts. I was going to walk in and stand in line with other people, be seen, and be me. The first time I tried it, I couldn’t do it. I walked into therapy. I said to Stephanie, my therapist, “I failed.” She looked at me and said, “No, you didn’t. You’ll do it when you’re ready.” That hit me.

Another thing that I learned along the way is I will do whatever I need to do or want to do when I’m ready. It’s like learning to accept the word failure, and not let it drive your everyday thoughts like, “I’ll do what I need to do when I’m ready.” I went through surgery in 2017. I started working with other people who also wanted to go through the same process at NYU Medical Center. I loved talking with people and helping people through this process.

I found that I could make a significant difference for them by helping them change their mindset. The thoughts and the emotions that we have all combined to form our beliefs. It’s our beliefs that will either propel us forward or block us and become limiting beliefs or they’ll mask what possibilities we have. That’s how I got into doing this coaching work, working with people in transition. I’ve also expanded into working with anyone facing significant life changes who could use some guidance and help.

The thoughts and emotions that we have all combine to form our beliefs. It's our beliefs that will either propel us forward or block us. Share on X

The core of what you have to do for any significant life change is going to contain some tools or characteristics that are going to be applicable across the board to other significant life changes. What have you found are some of the most significant tools or pieces that you’ve learned along the way to help you grow into comfort with who you are in this new transition?

If I were to single out one that was extremely helpful for me, it was my ability to envision what it might be like to do what I needed to do. How would I feel walking into a supermarket as a woman? What senses would I have? How concerned would I be about other people? What would I do? What would the sound of my shoes on the pavement be when walking into the store? The feeling of the air blowing around my body and legs, what would that feel like? If I was wearing a skirt or a dress, what would that be like?

I was meditating on that and focusing on that vision. The majority of the time, those thoughts and emotions that I would develop as I’ve worked on that vision would be supportive and help me with that process. When it came time to do it, I could reach back inside my mind and pull up those emotions, which triggered the feelings in my body. I could open the car door, get out, walk in, do what I needed to do, not be afraid, and have a positive experience from it. The vast majority of the time, the experience was far better than what I had imagined.

That’s a deep truth. We almost always overpredict the negative.

I found that I have a lot of automatic negative thoughts. Through my meditations, I learned how to quiet those, block them, and substitute more supportive thoughts. When I first started, this was terrifying, especially since I’d repressed it for so long so many decades. The second tool that I found that I liked was journaling.

The one thing that I found that was most helpful from that, and probably the most powerful, was I would sit at the computer. I’m not big on handwriting. I would sit at the computer and type. I didn’t worry about spelling, punctuation, or grammar. I poured my soul out into the document. The key to making journaling worthwhile for me, and I’ve found it’s similar for other people that I’ve worked with, is to go back after 3, 4, or 5 days and read what I wrote. A lot of times, it was horrifying. I can’t believe I thought that. I don’t want to feel like that anymore. I would find myself being, at times, horrified by how I felt and what I was thinking.

The other benefit there is you get to see the shift that’s happened. If you don’t go back and reread it, it slips your awareness.

I have talked to so many people who tell me that they enjoy journaling. I’ve asked them the question, “Do you go back and look at it within a short period and think about how you felt then, how you feel now, or how you would like to feel now?” For the most part, the answers I get are, “No, I never thought of looking back at it.” If you don’t look back at it, you’re losing out on the benefit.

There are some benefits to journaling. If people do it, then it must have some benefit. What you’re talking about is a well-known benefit to reading and rereading until there’s a part of the mind that is going to naturally start to integrate things and catch things that the ego would have me forget.

It’s the power of being able to shift your thoughts. We all tell ourselves a story every day about what we’re doing, what is possible for us, and all of that. I’ve found that a very powerful tool is to rewrite your story and you can rewrite it in stages. “I’ll never be able to do that. It’s impossible and I’m going to fail at it.” That might be a story that you would tell yourself when you wake up in the morning and think about what you would like to do.

I would start by saying something a little different. “I’m curious, how would it feel if I tried to do this?” Be curious about it first because you can’t tell yourself something that you don’t believe. Ease into the whole process and do it step-by-step. Soon, you can fairly rapidly shift what you’re thinking and shift your beliefs as a result. It’s our thoughts and our emotions combined to form our beliefs. That’s what I found through everything that I’ve been through.

If we don’t learn to question them and start actively working to change them, they solidify and strengthen. Our sense of self strengthens. I mentioned the word ego. My ego doesn’t want to change. My ego believes it is who I am. Unless we do a process like what you’re suggesting, go back, reread, and question, “Do I like that? Do I want to stay that way,” unless I’m actively engaging in a process that helps me change my thoughts, beliefs, and emotions, they get more solidified and rigid over time, rather than flexible and growing. The ego doesn’t want to grow.

I’ve also found that the mind wants to keep us safe and change is at best, risky.

To some part of the mind. There’s another part of the mind that can learn to enjoy the poster you have on the wall behind you. There’s another part of your mind that knows that’s the only thing that leads to growth.

Personal growth is phenomenal through this. I have gotten to the point where I look for it. I look for change and doing new things and new experiences. Through new experiences, I gain more insights into myself, my thoughts and beliefs, and the world around me. Our minds form our reality. My reality, I’m sure, is somewhat different from yours and most other people. We have a lot of commonalities in there but our beliefs, thoughts, and everything that we experience throughout our daily lives form our reality.

The other thing that I’ve learned along the way is that the human mind, how it connects with our bodies is through neuropeptides, hormones, and other chemicals that our thoughts and emotions trigger the production of those. Every emotion has a chemical signature in our body. That’s how we know that we have anxiety or depression. Our body receives signals from our mind through these chemical processes. Those chemicals are quite powerful and highly addictive. People can become addicted to the chemicals produced by anxiety.

On Your Mind | Wendy Cole | Transition Mentor

Transition Mentor: Every emotion has a chemical signature in our body. That’s how we know that we have anxiety or depression. Our body receives signals from our mind through these chemical processes.


You also mentioned the idea of fear and safety. I’ve given a number of talks about the idea that most of us have an addiction we’re not aware of and that is we’re addicted to the familiar. If I have been through it before and I survived, that means it’s safe. If it’s familiar to me, it’s safe. Even if the experience of it is mildly too severely unpleasant, if I survive it, it’s safe enough. I’d like to pose a question to you that comes to me. What would you say were the greatest hurdles or roadblocks for you making progress in this transition? Were they internal or external?

Internal, and that’s where I did the majority of my work. What I found with the external is when things changed in 2012, it made it possible for me to find a therapist who could help me begin this process of changing myself. Before it became a recognized medical condition or condition that you’re born with, the last time I’d ever talked to a doctor about it, I found myself in a situation where I was being told that I was a freak and that I should move to New York City and do things that they did.

What I discovered then was the predominant feeling of the medical and the majority of the therapeutic world was this was not treatable and there was no cure. I could have done it in 1970. I’ve talked to others along the way who also considered it in the ‘70s, the ‘80s, and even the ‘90s, and opted and chose to keep repressing and not do anything about it because we could no longer be part of society.

Once the change happened in 2012, WPATH put standards out for medical care and therapeutic care. Once that came out, that removed a lot of barriers. I could get therapy and legally get hormone replacement therapy. I talked to my psychiatrist at the time because what I had done in my defense was I would go to a psychiatrist. I’d tell him I’d have anxiety, depression, and all kinds of other things. I would blame it on work, family, or anything like that. I wouldn’t tell him the underlying cause. I never would reveal that again, not after what I was told in 1970.

I was prescribed all these meds which didn’t help. I was living in a fog. It was dulling the senses. It wasn’t addressing what I needed. I went into my therapist’s insistence in early February of 2015. I went to my psychiatrist and I told him. He wanted me to go to Johns Hopkins immediately. I knew that Johns Hopkins at one point was the Founder of the surgery for changing one’s sex. I’m going, “This is good.” I went home. I got online and found out at the time, this was in 2015, that they had stopped doing that. It was conversion therapy. My psychiatrist wanted me to go to conversion therapy, which I don’t believe in and I don’t believe it would work.

It essentially is saying they think they have a therapy that can change who you are or how you feel about yourself so that you no longer want to have the transition.

When I told my therapist that, she said, “You’re not seeing him again.” She had worked with a lovely man in Princeton, New Jersey in the hospital ward. She said, “He’s now in private practice. He’s near where you live. Go see him.” I did. In my first session with him, he said, “You don’t need all these meds. You’re on hormone replacement therapy?” I said, “Yes.” He said, “Great. I can take you off of three of these right away, and we’ll phase you down and off the others.” He said, “Come back in 2 or 3 weeks and we’ll discuss how you’re feeling.”

The first time he saw me, I was in my male facsimile mode. The second time he saw me, I walked in as Wendy. I found out from my therapist about a year later that the two of them, my psychiatrist and she, had a discussion that he couldn’t get over the personality change I had experienced in that short time. Seriously, it was like the skies opened up. I was no longer in a fog. Everything started to feel right and I started to see, “I can do this.”

I no longer had the fears. A lot of the mental work that I was doing to align myself internally with who I am and dispel all those beliefs that I had from decades of repression started to evaporate. By the time I reached June of 2015, I couldn’t have been happier, more excited, and curious as to what and where this was going to lead. I had already decided there were no guarantees in life. The only thing I could do was take that leap of faith and go forward. I didn’t have any idea where it would lead me or what it would lead me to but I knew that that was what I needed to do.

On Your Mind | Wendy Cole | Transition Mentor

Transition Mentor: There were no guarantees in life. The only thing I could do was take that leap of faith and go forward.


The greatest roadblocks, barriers, and hurdles were internal.

With the external changes in the medical community and therapy, all that flowed very nicely for me. In terms of society as a whole, I came to a realization fairly quickly that my only goal was I wanted to blend into everyday life as any other woman. Nothing special. I wasn’t going to try to be out there as a model or anything like that, just did what I needed to do. When it came to how it was viewed in public, I came to the understanding that gender is assigned by someone seeing you for the first time within a matter of seconds. It’s almost subconscious, if not subconscious. It’s on visual cues.

It was up to me not to upset that gender assignment in public if I wanted to blend in. I came to the realization fairly quickly that to do that, I didn’t need to be perfect. I did a lot of research on gender behavior, gender cues, mannerisms, behaviors, and all of that. I started working on myself to practice those to be able to display them in public comfortably and as naturally as possible. I very became self-aware and found that self-acceptance also started to build. I didn’t know so much before I went full-time in July 2015 but after that, I began to have self-love before I hated my life. I hated who I was. I was so distraught with that, and then it was different.

When you talk about working with others in transition, you mention mindfulness and journaling. Are there other tools and processes that you find useful in working with people to get through transitions?

One of the things I work with them on closely is challenging their limiting beliefs and helping them shift those beliefs. For some people, it works well with meditations. I find a lot of positives through the journaling aspects of it, going through processes to shift the mindset, recognizing what your limiting beliefs are, starting to question them, why you believe in such and such, and why you believe that is limiting you. The other thing is practicing life situations. Have you ever been out and gone grocery shopping as yourself?

I found that was extremely helpful to me personally. I would give myself life tests. On my way to therapy as Wendy, I would stop for coffee. I would go to a grocery store, pharmacy, and various public situations or simply go for a walk through a busy town where I would see people and go window shopping. I might do that for 1 hour or 2 every day that I went to therapy.

What that built up in me was a life experience that said, “This is possible.” That’s very helpful because most people, when they start this process, are terrified. I have met people who have changed their legal identity and names and are going to work as themselves, yet they’re still afraid. The reason that I believe they’re still afraid is they haven’t done the work that they needed to do internally.

On their limiting beliefs.

I’ve met people who the only place they’ll go when they go out to be social is a gay bar. I don’t have those limitations. I’ve never experienced them because I stopped having those beliefs. I found that there was no need for them. As a result, when I’m working with somebody trying to help them through this when I was doing this in person in the town that I lived in when I first started it, I would take people out for their first experiences. I would go out with them and show them that there was nothing to be afraid of.

Many times, people like myself don’t understand the little social cues. I was walking down a path, a walking trail going into town where I lived with someone and it was her first time out. We’re walking down this trail and she keeps seeing women jogging by us in the opposite direction. She turns, looks at me, and says, “Why are those people laughing at me?” I looked at her and said, “Nobody’s laughing at you. That is the way women acknowledge other women. When they see you, they smile and nod their heads. That’s a way of saying, ‘Hi. How are you?’ It’s a female thing. Guys don’t necessarily do that.” “I didn’t know that.”

The other thing that I try to do with people is go through all the subtleties of mannerisms, behaviors, and speech patterns and how people interact with you. It’s very different as opposed to interactions with a male. Male-to-male interaction is different than female-to-female. That’s something, especially if you haven’t been highly observant of it, you won’t know. That leads to more fear coming up.

What’s the timeframe that you talk to people about to be patient with themselves for X number of months or years as they’re trying to learn all those complex things?

One of the things that I’ve experienced within the community is there’s a belief that this takes a long time and it’s very difficult. My response to that is, “If that’s what you believe, then it will. It doesn’t have to.” You can get to a point where you can get by with this in a very short period. It depends on how much work you want to do internally.

On Your Mind | Wendy Cole | Transition Mentor

Transition Mentor: You can get to a point where you can get by with this in a short period of time. It depends on how much work you want to do internally.


I always want someone to have a therapist. That to me is key. I see the role of the therapist in this process of helping the person with who they are and helping them unpack the baggage and everything that they are carrying with them from their previous life. I see my role as helping them go from now and go forward and find joy that they never knew possible. How fast you go, that’s up to you.

Last 2022, I took one person through the whole thing. By our sixth session together, she had changed her driver’s license and her legal name and was living full-time. What’s the difference between her and some of the others that I’ve worked with? She was ready. She knew what she needed. In our first session, she opened up staring down and not looking at the camera. She said, “I am scared. I’m tired of living a lie. I have no clue what I’m doing.”

I looked at her and said, “Good. That’s why you’re here. Let’s get to work.” We started. She made rapid progress. I had her journaling. She wasn’t big on typing or writing. She had her way of doing it. She did these videos and we started going through everything each week. When she came into our sixth session, she said, “I found it was very easy. I went and changed my driver’s license. Everything’s done.”

We made a list of all the other things that she needed to go and change. It took me six months to change everything but the initial things were fairly easy to do and fast. She was living as herself within six weeks. I’ve had others that take as much as 6 or 7 months. That’s okay. That’s their process and how they’re doing it. They do it when they’re ready.

Do you do a significant amount of this virtually?

Yeah, it’s all Zoom. The majority of the people that I see and have seen over the years are all over the country.

Let me ask you to get centered, take a breath, and think about what we’ve talked about so far. Is there something that you want to go back and highlight or something we haven’t even mentioned yet that you want to get in this interview?

One of the things that I believe is that it’s never too late for any life change. Often, I’ll have somebody say to me, “I’m in my 50s or 60s.” I did this. I started this at 67. I had surgery at 69 and I’ve never looked back. I am so glad I did this regardless of my age. I’m 75 in 2023 and I’m nowhere near done yet. This has changed my entire mindset and self-image, and how I feel about myself.

It's never too late for any life change. Share on X

There are days when I have things that are not quite right and beliefs that I am working with but it gets easier the more you do it. We have thousands of thoughts going through our minds every day. It’s the ability to learn to use the tools and things that work for you that will help you manage those beliefs and thoughts and help propel you forward. You can have an exciting life regardless of your age.

If people want to reach out to you and connect with you, what’s the best way for them to do that?

WendyColeGTM.net/Connect. That’s my website. There’s a way to subscribe to my newsletter. They can send me a short message and even schedule some time to have a conversation. I don’t try to sell my services. They speak for themselves and that’s it.

Thank you so much for taking the time to share with us. Good luck with the book project.

Thank you. Timothy.

Take care.

You too, as well.


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About Wendy Cole

On Your Mind | Wendy Cole | Transition MentorAs a Transition Mentor, Wendy Cole helps her clients identify, explore, and eliminate the stress of facing life’s changes. Since 2017, Wendy has guided others through transitions. Her life experiences are the tools she uses. She believes in the mind’s powers; she practices mindfulness, shifting her beliefs and energy to support herself going forward, making profound changes in her life, and health, and finding joy in being.

Knowing who you are, and not BEING who you are: this is the starting point of every Transitional situation. You KNOW who you truly are, in every aspect, but the outside is what matters. That is what people see. Taking that first transitional step is TERRIFYING. It’s the stress: the stress of the journey, the stress of the mental weight, the stress of worrying about the outside world… The physical transition is the easiest part; it’s getting through the mental transition that holds us back.

Knowing from childhood she was a girl, Wendy yielded to familial and societal expectations to fit in. At age 67, Wendy changed her life with her transition. Beginning in January 2015 she focused internally: accepting who she really was, confronting fears, doubts, and anxieties that held her back for decades. She took the leap of faith to find freedom and joy in being herself. By July 2015, Wendy was living as a woman. She had her long-awaited surgery at NYU Medical in 2017. Wendy knows that focusing inwardly to find freedom and joy will benefit the rest of your life.


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