How are you getting your face so smooth with no facial hair?

I bought a laser hair removal device on Amazon for about $300 that I can do at home daily and takes about 12 weeks to work

In the pictures I take, I have makeup on, so that hides my stubble a bit after shaving

Are you taking estrogen?

I am taking estrogen

Are your mom and dad supportive?

My dad doesn’t know and my mom is supportive now

At the start, she thought it was another one of my antics. I’m big into shenanigans and trying to stand out from other people.

I wonder if that characteristic of needing to play identity games not being like others might have always been a sign there’s something up with my identity.

How long have you felt like a woman?

Being attracted to all kinds of toys as a kid (legos, poly pockets, monster trucks),

Having an affinity for tights

Liking having my nails done

A heavy affinity for women and not a strong affinity for men

My sexual genesis and what kinds of things I was into

My sex life and details in that around how I could never seem to be aroused by traditional sex (jamming my cock into things)

Cross dressing for about 8 years

Not really understanding what it was about for me

Painting my house

Gender Unicorn test illuminating what kinds of characteristics go into the different identities

Just never really associating with being ‘man’ ‘manly’

I worked out a lot to try and get my body to a point of feeling good about myself

And could never really get there

I thought once I was big I’d feel different

Shadow work really illuminating for me that I had a problem with others judging people for their identities

Which indicates I have some kind of fundamental problem with my identity

Overall with shadow work coming to realizations around revenge and validation

Somehow I needed those things within myself

Why does Will need revenge on Will?

Why does Will need validation from Will?

I’m losing my sense of a need for external validation and revenge which is awesome

Indicating that I’ve found something hidden within me through the shadow work and all.

My therapist told me he’s not surprised

He saw so many signs

So that’s cool I can figure this out with him now too

Having Aunt Pam, my therapist, my life coach, my mom, my roommates, and my girlfriend.

I have all kinds of in-depth conversations about all kinds of things every day which lead me to realizations around my own identity and relationships.

The more I lean into it, am on hormones, dress the part, change my voice, etc.
The more I feel like it’s the right thing

So for years I’ve been feeling some kind of lack of fitting in, need for revenge, validation, and feminine something going on with me in my sex life.

I can’t say I knew I wanted to be a woman until just 6 months ago around the start of November when I was in Tennessee coming back to Minnesota.

That’s when I knew exactly what it was and then decided to talk to my physician about it and try to find HRT.

But for years I’ve not been happy with what I get no matter how hard I work towards it and didn’t know why

In addition to all these feminine-related activities happening throughout my life that were notable for me.

An obsession with feminine colors, feminine clothes, feminine things and feminine sex. All that stacked up was an indication there might be something feminine about me to figure out.

I worry about your safety

There’s not much I think I can do really.

I always look over my shoulder and watch my back.

I try to choose my locations wisely.

Like in Florida they passed a law about how transgender people have to go through a bunch of difficult obstacles to be who they want to be.

Where I’m at in the north US makes that much easier which I’m happy about.

I’m always interested in hearing people out, to be as safe as possible

Sometimes I think we find ourselves at a crossroads of self actualization and safety.

Those things can go together and I’ll try to find them together as much as possible.

If I life a safe life that lacks self actualization, I’ll feel the way I felt last November

Not having any sense of peace going to bed at night.

And feeling the weight of that lack of peace compounding over 8 years and what that does to my will to live.

The lightening, liberation, and freedom I feel now is great

I feel like I can see things differently now and that I’m so much more functional in my job, life, and relationships.

I choose safety all the time in life. Safety in investments, safety in experiences, and safety in relationships.

Here I’ve found myself backed against a wall the way I did in high school where I had to choose do I drop out and take the ‘unsafe’ route or do I do what people consider ‘safe’ by getting a GED, diploma, or degree.

I’m backed into a corner in a similar way, do I choose the ‘unsafe’ route of being transgender at a time when transgender women specifically have a hard time being accepted in society. Or do I choose the ‘safe’ route of being non-binary or not really fulfilling my identity in some way to avoid danger. That’s what I’ve done for a while, is put that question on the back burner and peruse some other ways to be happy.

It all comes back to identity for me and finding this thing I have to change to feel how I want to feel.

The outside world is now an increased threat to my safety.

But denying myself self-actualization turned me into a threat to my own safety.

My decision has been good to me and I hope it will continue to be.

Do you plan to tell your dad?

Yes, years ago he had mentioned he’d still love me if I was trans/gay/some sort of non-sys kind of person. Aunt Pam told me that support and understanding of trans people has really only advanced in a big way over the last 5 years, so what my dad said about 7 years ago might no longer apply, so not to write off his expected response.

I feel like I’m just not really ready to tell most of the Middleton family yet. Aunt Pam said Bob was surprisingly supportive of her being LGBTQ+. And this was a time tons of years ago. My therapist said my news might give Bob a heart attack, but maybe due to his reaction with Pam years ago, he might be supportive.

That would shock me, but people surprise me for the better sometimes, so that’s really neat and definitely possible.

I don’t really understand the line between transgender nad transsexual.

I think in culture at large, the line is blurry.

Transsexual could be a derogatory term in some circles.

I think there are a few perspectives and society hasn’t really picked up on either too strongly I think.

Transsexual relating to ‘Sex’ and physical characteristics and transgender being ‘gender’ a construct defined by humans to create gender norms, gender rules, and gender leadership.

I think to be transgender you don’t have to have any HRT or surgeries

And to be transsexual you would.

But I don’t really associate with either term to concretely. Doesn’t really matter to me.

Do you believe your transition will affect your work? Like client referral pipelines? Will people you know stop referring people to you?

I think some people will say less around me and some people will say more.

Some people will say the same.

Being a sys man, sexism, racism, homophobia, etc. are all things that others feel comfortable joking with me about. And I think that dissolves a bit.

I think the people who joked with me about those things will no longer do so.

I think they’ll feel that they’d get in trouble or push me away.

Jokes and inner thoughts I think are a strong way people bond with one another.

Losing access to people’s inner thoughts and jokes, I think will create a sense of loss of connection between people I used to be close to.

And that loss of intimate connection will result in less pipeline or client referrals.

I did think about that a lot. I work with people who have specifically highlighted me as being a white straight man. So I think if it’s been explicitly stated, then it will have some kind of impact.

I don’t think impacts like that matter. I think my thinking around scarcity came from a limited perspective of people. The gains I’ll get through self liberation and not being depressed for unknown reasons, will be a boost to my ability to get things done.

I’ve been learning through shadow work that scarcity around loss is a product of focusing on the wrong things in life.

It is an indication I’m concerned more about the future or not having something I cherish or something I believe I need to survive.

Like I was very scared about leaving my full time executive job for fear of losing opportunities and income.

But that income and opportunities was a limiting factor in my life.

The future of my career staying in that position would have put my life in a choke hold and I wouldn’t be able to grow into who I want to be.

I’m now making about $50k/year compared to $100k/year I had been making working for someone else.

But my life is so much better now. More peaceful, more control of my schedule, more control of my future.

Transitioning affecting my work will kill some pipeline, but that pipeline needs to die anyway. If I prevent myself from expressing myself or fulfilling myself to try to keep people who hate who I truly am around for money, I’m living life for all the wrong reasons.

I think the pipeline that dies can be recovered in other ways. And I don’t think as much of the pipeline will die as I think it will.

I’m getting a lot of referrals basically from myself and the content I create on YouTube. I don’t get a lot of views, but the people who do view it really need what I’m talking about.

I saw a podcast where someone was talking about how they didn’t know how to build something and her husband was like, “did you see if Will has a tutorial on that?”

I’ve never met these people, but apparently even though I have low subscribers and views, the views I do have mean a lot. People I don’t know talk about me in their homes as they build their WordPress sites and that’s really cool to me.

I love that feeling and it feels like I’m expanding my presence as a human/spirit/etc through that. Like my existence is bigger than my physical body.

That’s my main source of pipeline right now in combination with existing clients.

I’d like to expand to more spaces and get into more spiritual work.

Has your body been feeling ok on the estrogen?

Yeah, I feel great. I feel more slow with reflexes, muscle mass dropping, emotions are easier to feel, and more restful.

It’s so crazy to compare my experience in a male body for so long to what I feel now. It’s completely different.

I feel like most people wouldn’t have that perspective to experience multiple biologies. I don’t have uterus-related issues (like a menstrual cycle) which are in my mind the most painful and complicated physical ones for women.

But I can see colors and feel sensations and emotions completely differently. That feels really cool.