identity

Go Your Own Way

Are you a Fleetwood Mac fan? My mom is. I’m not. But I do appreciate their music.

You might know they have this great song “Go Your Own Way”. I think it’s about not committing to a relationship.

If I could
Maybe I'd give you my world
How can I
When you won't take it from me

You can go your own way
Go your own way
You can call it
Another lonely day
You can go your own way
Go your own way

Tell me why
Everything turned around
Packing up
Shacking up is all you want to do

Want to know what I hear? A love song to society. It’s pretty much how I feel about human beings sometimes. Well, most times.

It seems to me sometimes that people would rather keep picking habits that don’t serve them over ones that do. It seems they want the most for the least amount of work and effort involved.

They want it cheap, fast and easy.

But a life well-lived is none of those things. In fact, it takes incredible amounts of work and tenacity. It’s so much easier to swim with the stream and stay alongside the status quo. So that’s what most people do. That’s what we see all over social media. And most people seem to be ok with a life like that. But I HATE IT. And I think my people (you) do, too. We crave being different and unique and breaking out of molds and boxes.

It takes a lot of work to do that.

But YOU CAN do it. I know. I do it all the time and have been doing it my whole life, really.

When Dave Matthews was the band to follow back in the day, I intentionally didn’t buy a CD. Just one example of many.

And there have been many days, especially in the past six years or so, when I doubted why I lived my life like that and when or if it would ever pay off. I began to get really worried that living outside the lines was catching up to me and I was getting left behind. I was losing the game. I wouldn’t ever be successful. It seemed like the way to be successful and happy, no matter fake and weird it seemed, was to do what everyone else was doing. To just be “normal”.

But I trusted myself. I kept going my own way and doing things differently, in ways that felt right for me. The more I did this, the harder my life got. And if you’ve been following along with me this whole time, you’ve seen the process unfold because I’ve shared it.

And maybe now you’re seeing that…is has totally been the right path all along. Because my life is going the way I want it to, even if it’s nothing like what mainstream society does. And that’s my whole message to you: go your own way. Even if it’s hard. Even when it’s scary. Even when you totally doubt yourself (like I often do).

Because being yourself CAN and DOES pay off. Maybe not the way it does for people who follow the silly societal rules and trends, but do you even really want that for yourself? Maybe you do. In which case, you should probably stop reading.

But if you’re trying to be yourself and have always felt like that was weird or wrong, I’m here to tell you that it’s perfect the way it is. You just have to really believe in yourself and keep sticking to it, especially in the darkest deepest moments when you feel alone and hopeless. Because then you get to have the big breakthroughs that make it all worthwhile.

Like me and what I got invited to do next week, for example. On Wednesday, I’ll be in NYC interviewing author and entrepreneur, Randi Zuckerberg, who wrote “Pick Three: You can have it all (just not every day)”. Pretty cool opportunity, right?!

Totally. And I was invited to do this in my role as a Global Mentor for WeWork Labs. Also another very cool opportunity! And I got that opportunity from other cool things that have happened to me for the past ten years of being a coach and speaker and writer.

And you know what’s the coolest thing about all these experiences? I got chosen for the work I do as a coach. And I emerged from the profound societal stigma of my identity as a trans* person and have persevered to be successful in a career of my own choosing. I also overcame my own personal limitations and mindset to persevere no matter what. Because is it possible I’m being given opportunities simply because I’m trans*? Like being tokenized to make a person or organization look better because they’ve included me? Sure. It’s totally possible and maybe even likely.

But I’m over it. As long as I’m being given opportunities to be visible and inspire (Dillanspire) people, then I’ll take as many as possible for whatever reasons.

If you haven’t experienced stigmatization like this, maybe you don’t get the gravity of what I mean. But I bet you can relate to being or feeling limited by someone or something in your life and told what you should do or be. You may have even been rejected by people you love, like I have, for being yourself. Or you feel that rejection on a daily basis.

And I bet you can relate to how horrible it feels.

And how tempting it is to give up in moments like that.

But if you’ve felt that, then you know how awesome it feels to not give up and how it’s feels SO GOOD when you’ve stuck to your values and principles when you were tested.

And how great the victory feels when you’ve gone your own way and have proven to yourself that it can and does work. Having that experience is TRUE success, in my opinion.

I know Randi feels similarly because I’ve read her book. And while we’ll be talking about work/life balance, we’ll also discuss how hard she worked to achieve her own personal version of success on her own terms.

Which is something we share in common, despite how different our lives are. We’ve both gone our own way and we’re better, stronger people because of it.

I hope this inspired you today,

Dillan

Going Home for a Fresh Start

Last week I got a text from my friend.

“This might be something you want to do,” he said.

It was an opportunity to share a story on stage at WGBH: Stories from the Stage in Boston. I replied, “UM, YEAH!!!”

And so that’s what I did.

I left at 4:45am in the morning and drove back Home to Boston where I lived from 2006-2016 to tell a story on stage about coming back home to New Jersey this year and what it’s been like for me. I had less than a week to work out all the details and the hardest part was how to navigate the major point of why they invited me to share: because I’m transgender.

I struggled with it, wondering if I was being tokenized or provided an opportunity to share my story. After feeling a lot of feelings and almost not going at all and then processing since leaving the stage that evening, I’ve come to realize it’s always probably going to be a little bit of both moving forward. It comes with the territory of having a marginalized identity in a time of rapid cultural change. I’m choosing to embrace what feels uncomfortable about that and be grateful for what’s wonderful about it. Just surrendering to it being both/and, the Middle Way that Buddhism teaches me to embrace.

It’s the best way to be myself, which is the talk I walk for my readers and fans and followers and friends. I’ve been doing it since becoming a coach in 2009. After spending six years navigating my business “rebrand” by myself, I felt relieved to have words to share in ways I wanted to for the pre and post interviews at WGBH. And I told my story in a way that shared my experience and helped evolve our culture forward a few notches. At least I hope so.

I told a story of going back to a place I once worked and how it felt to be there among people who once knew me. It involved having a major panic attack and calling my mom and was full of really relatable themes and issues any person can relate to. I am really proud of that story and I hope I’m able to share it more widely soon.

Going back Home has been a deeply intuitive journey. I stopped trying to plan or strategize back in 2016 when my Vermont move showed me how wonderful it is when we let go and jump. I lost some of my joy and playful spirit when my sublet in Boston last June coincided with Jim’s sudden death. He was my therapist of ten years and my rock. The shock of that sent me reeling and I struggled to find my feet and know what to do next. I just kept following my gut and ended up right back where I left in 2006.

And wonderful things are happening from this fresh start. I’m reuniting with my mom and forging a wonderful relationship. I’m meeting new people and making new friends and catching up and building new relationships with people I knew before. I’m spending most of my time alone, actually, having become a bit of a hermit these past few years. I don’t mind it and actually prefer it. I’m consciously integrating past and current versions of me and it’s making my brain explode but it is an essential part of my journey so I can help others. I couldn’t have predicted this is how my life would go but as it all unfolds, it makes perfect sense.

I think it’s true for every person. We grow and evolve as much as we allow ourselves to do it. Most people limit themselves more than anything. There’s a safety in staying the same but we stay stagnant to the extent that we let fear ride shotgun.

I spoke to someone in Boston who was born and raised there and has been very successful with his business. “But I’m really bored,” he said. I could see why he said that and I’m anything but bored and actually sometimes crave the consistency other people, like this man, have in their lives. But that quality about me, my literal inability to sit still for any extended period of time, has made me who I am today. I’m constantly seeking and searching for what’s next or the newer version of myself. It’s a gift for the work I do, and I keep this in mind when it feels challenging. It seems to be why I’m here.

And that was the fresh start I shared in my story on stage. I talked about how I’ve had to continually find more patience with the things people do and say to me since I came out as transgender and how much I’ve grown up from that experience. I literally am not the same person from the inside-out. Changing on the outside generated a total transformation and fresh start on the inside. But it isn’t all unicorns and rainbows as it may sound in hindsight. It’s been a difficult adjustment. It’s tested me like nothing else. But from the past six years, I’ve learned the invaluable lesson that we always control our response to any situation, we get unlimited fresh starts to be our most compassionate and patient self.

I had to leave Home to become this version of myself and come back Home to apply it. And then go back Home to Boston for a brief stint to see if staying where I am in New Jersey is what I really need to do. It was so tempting, to be back in a place that was familiar and fun and full of things that would make my life much easier than it feels right now. Where I am living, I am really being a trailblazer and I feel self-conscious much of the time. Rural New Jersey isn’t the metropolis of queer-friendly Boston. But it isn’t all that bad, either. In fact, I’m finding surprises around every corner and in people I would have ruled out based on my own assumptions. Isn’t it funny how we can do that? The way we make reasons why we can’t find freedom anywhere we choose to feel it.

Often we’re the very reason why.

And then I look down and see the tattoo on my arm, scrawled in my own handwriting that says, “the true home is within.”

Know who you are.

Kanye West is making news from what he sees as his powerful self-expression.

It's confronting people and challenging them in many different ways.

I feel compassion for him. I wonder if he's actually doing ok. I wonder how much of what he's sharing comes from intentional choices to get media attention or because he's actually ignorant.

At a basic level, I do support his self-expression. I support him saying what he thinks is true and real. We all deserve that. But he's speaking from a position of power in our society, and incredible wealth and privilege at the moment. And with that platform comes responsibility.

People have strong feelings about what he's saying and doing.

It comes down to knowing who we are, not only for ourselves with our own opinions and perspectives but who we are in relation to all human beings. We don't exist as islands. We have impact. We all have relative privilege and disadvantage. Each and every one of us, some of us more than others.

I shared this sentiment on the two panels I sat on this month, once in Pittsburgh to an audience of tech/startup-minded individuals and last week in NYC to an audience of activists, social media marketers and all sorts of other people.

I am consciously positioning myself on those panels and outing myself as a #transgender person to share insights about privilege and power and identity development. I'm working to help the current social awareness of trans* people and what we can do or are capable of being and where we belong. I am also just sharing from the deep reservoir of information and knowledge I've acquired throughout my career.

Most people don't know who they are outside of what society has shaped them to be. Most people aren't given the tools to explore identity and know themselves as complex, dynamic beings capable of changing and evolving with each moment.

It's the work I've been doing for my entire career. It's the message I've been sharing since becoming a coach. It's starting to gain traction. The time is now for me to keep expressing myself and sharing this knowledge to help others. I know everyone won't agree with me and the ways I'm doing it and how and why.

It's why I support Kanye sharing his truths, even if I disagree with him.

Ultimately, we all deserve to say what we need to say.

When we can do it with integrity and from a place of deep introspection and awareness, we can be even more powerful. When we can do it from a place of love and wisdom and compassion, like I did several weeks ago, we have the opportunity to change lives for the better. We can empower ourselves to inspire others toward their own self-empowerment.

This happened for me several weeks ago at my talk in NYC and my schedule has been so packed I haven't even been able to share about that. Here's a small video that's a bite-sized recounting of that experience. And know I'm working hard to make it happen again and more often as much as possible.

When we know who we are, we are unlimited.