Coming Out, Getting Clear, and Living for Yourself with Diane Whiddon

Today, I’m talking with my dear friend, Diane Whiddon, about her coming out story. Diane has dedicated her life to inspiring entrepreneurs to listen to themselves and build the business they’ve always wanted. We’re diving into what motivates her to do the work she does, as well as taking a deeper look at who she was before stepping onto her purpose path and the rough road that brought her to where she is today. We’re pulling back the curtain on everything from an upbringing that taught her to mask and people please to discovering she’s a lesbian to the clarity and authenticity she pours into her life and business now.

What to Listen For:

  • Who was Diane Whiddon before?

I learned at a really young age to read the room and see what other people were doing, constantly like taking litmus tests of how do I need to be, how can I solve your needs and make you okay and support you emotionally, but then like what’s even safe for me to experience and express in this space?

  • Accomplishing a lot, and still feeling miserable
  • The series of events that lead to her dark night of the soul

I had gotten divorced, and I was running my website design company, which is how I got my start online. A couple of things happened. So one of the first things that happened, it’s so weird. Google changed their search results. So one of the things that happened was if you Googled website design for authors, I was number one or number two, like anywhere in the world.

So I had clients globally. I had clients in Hawaii and Canada, UK, and Vietnam, and Haiti. I had clients from all over, and then, overnight, all of that search engine traffic vanished, and it was localized. And so now if you searched website design for authors in Massachusetts, I was on like page five.

  • Realizing she needed to pivot
  • Getting out there and networking in real life triggered her trauma
  • Not knowing enough about healing and self-discovery to handle it well

I was thrust into this huge depression. I got extremely suicidal, and my dark night of the soul, I remember, I had this one moment where I was sitting on my couch and had been on my couch for three days. I had no idea what to do. I had no one to call to help me. I was totally alone and felt completely isolated.

My business is changing and kind of struggling. I don’t know what I’m going to do to survive and be okay. And I had this moment where I lived in downtown Denver. At that time, I lived on the 11th floor. And I had this beautiful balcony and I just, I was in this horrible place, and I was like, I could just end it right now. I could just run and jump off that balcony right now and just be done with this whole place.

  • The thought she had at that moment that changed everything
  • Understanding the relationship between accountability and freedom
  • The power of choosing to stay

“I’m choosing this. And that made me invested in a new way. And it was the beginning of me breaking that habit of pleasing everybody else and the winning strategy of pleasing everybody else and moving into a place of if I’m the only one here, I don’t live for me. What the heck do I want? What the heck is important to me?

  • How asking what she wanted started her on the process of reorienting
  • Examining the things she wanted and the stories she told herself about why she couldn’t have them
  • Taking a year off and reading books for healing
  • Realizing during this time that she’s gay

I didn’t know that I was gay because I didn’t know that I liked broccoli. I didn’t know that I liked the color blue.

I had no concept of who I was, and that’s one of the main fallouts of childhood trauma, or even being in an oppressed group that you learn that you are wrong. You’re wrong. Whatever you’re doing, whatever you’re saying, you are wrong. Particularly your happiness is wrong. Your satisfaction is wrong.

Your joy is wrong, but you are wrong. And so you learn to just deny every single impulse and pack yourself into this nice little presentable package that makes everybody else okay and makes everything shiny and puts everyone at ease. God forbid we have a gay person in the room because everybody freaks out.”

  • Putting herself back together and seeing how much of her life had been sacrificed to self-betrayal
  • Attending an inner child retreat

It just changed my whole life because I was like, wait a minute. I have a separate part of me that is running the show, and I have like a child, who’s a kid who never healed who’s like making all these decisions for me. Well, that would explain why I act like a complete idiot sometimes. That’s good for self-awareness. So, that was kind of the beginning for me. And, it was after that, that I know I started reaching out more and more to reading books then like reading books on healing.”

  • What opened up the flood gates of self-love and self-honoring for her
  • Examining what she really wanted and learning she’s gay
  • Realizing how much she’d been hurting herself up until that point
  • Growing up in the deep south, looking feminine and hearing every homophobic thing that people said
  • Defining her style as a gay woman
  • Exploring how she wanted to present herself in the world
  • How her work and business changed during this time

I realized I didn’t want to build websites anymore. I loved the marketing piece, and I loved working with clients and helping them contribute to the world and give their gifts and make more money and, and expand who they were. I loved that work, but just the website design model was too limiting.”

  • Shifting into coaching but still struggling with people-pleasing
  • The power in learning to say no and set boundaries
  • As she put more pieces of herself back together, she put more pieces of her business together
  • About her Get Clear program, a 6-week course designed specifically to get you in touch with what is most important to you and what you love about your work and guide you through a self-awareness process so you can get to know who you really are, what your gifts are and who needs it
  • Why you need to stop telling yourself you can’t
  • Leaving the adolescent male energy out of her coaching
  • What she wishes her younger self knew

I wish I knew I could trust life. That would have changed everything for me. For me, life itself was the enemy. It felt like every time I showed up as me, every time I was in my joy, every time I was doing something that felt good, it felt like life itself just beat me down, you know, um, you and I talked about the Dropkick.

It always felt like that to me. It felt like out of nowhere, life would just bam! And you know what, and that’s a trauma response. Learning that and understanding that and getting to a place where I can trust myself was a really big deal because it led to this greater understanding that you can trust life.

About Diane Whiddon:

Diane Whiddon has dedicated her life to inspiring entrepreneurs to listen to themselves and build the business they’ve always wanted. Motivated by her desire to break free of the traditional patriarchal business model that’s based on competition and lack she has become a student of clarity, intuitive marketing, and the sheer joy of running a business.

She got her start in the online world, building websites for writers and turned that into a web design agency with hundreds of clients that eventually launched her career as a marketing and brand consultant.

Today, her work includes her signature Get Clear course ( that teaches biz owners how to trust themselves enough to take more risks and have more fun with their businesses. She specializes in working with healers, intuitives, and creatives, but anyone who loves what they do can be transformed by her work.

The one thing she wants you to know is that, often, the best business coach for your business is you.

Website and social media links:

Read Diane’s free e-book, May You Shine


Access our free 8-part Journey Mapping™ sampler program and begin uncovering the purpose of your path at

Read my memoir, Unravel: Rising Up and Coming Back from a Season of Living that Damn Near Killed Me at