More About Caitlin
Caitlin here.
You’re gonna wanna pour yourself a cup of your favorite bevie, maybe even light a candle to get the vibes going and prepare yourself… to quote the great Mary Oliver… for my one, wild and precious life (story).
An ‘assertive’ beginning
I was born sunny side up and with a face presentation. I was born looking up and out – a combination so rare, only 2.5% of the population is born this way. This was to pave the way for my mindset moving forward. At 5 years old, my Kindergarten teacher could sense my innate assertiveness was perfect for the business world as was shared on my report card.
1990
2002
A ‘clueless’ childhood
Although born ‘face first,’ I started to develop low self esteem, a poor self concept and a lack of self worth. This was a result of a very difficult and challenging childhood, particularly a tumultuous dynamic with my father. (We all do the best we can.) I entered high school with a negative self-view that must have been felt by my peers because I was voted the ‘class clueless’ superlative. And yes, I embarrassingly had to stand in front of the whole senior class to accept my ‘award.’ Know what else was embarrassing? Those pencil thin early 00’s brows.
An ‘enlightening’ young adulthood
After high school I attended Salve Regina University and dropped out after a year and a half. Although academically adept, my unhealed trauma prevented me from being able to succeed at the time. This prompted me to begin my healing journey. I started reading self-help books, developing my spirituality and went to wilderness therapy (my parents forced me, but secretly I liked it) and traditional therapy. I attended a 3 year program at the University of Spiritual Healing and Sufism where I learned how to work 1:1 with clients for the first time and guide them through a transformation. My talent for facilitating powerful and rapid change within others was immediately apparent. Although being the youngest in the class at age 21, where many people were double my age, the teacher pulled me aside and boldly said, “Caitlin, you are the best in the class. If you choose to do something with this, you will go far.” This was honestly the first time in my life I felt good at something and acknowledged for it. During this period I also moved to Boulder, Colorado to attend Naropa University to study early childhood education and psychology.
2006
2009
The professional nanny & teacher era
Interestingly, I never finished the early childhood education program at Naropa University (college just wasn’t my path), yet I was still hired by Naropa as a Teaching Assistant for the Body Mind Centering class. I was also hired by Jarrow Montessori and quickly became the in demand substitute teacher, co-lead preschool teacher for their summer program and was offered a full-time primary teaching position. During this time I was also a ‘professional nanny.’ Basically, Mary Poppin’s had nothin’ on me. Here I am in Chennai, India, where I spent time teaching English as a volunteer.
The wakeup call in jail
Although I had already done a lot of self-work, I still had more to go to reach a solid baseline as I continued to struggle with my self-esteem and self-worth. I hadn’t quite found my life path yet. I was working with children, and although I was really good at it and loved it, I knew I was destined for something beyond what I was currently doing. I was teaching and working as a nanny for a high-powered family that I felt intimidated by due to my poor self-concept. The mother had similar qualities to my dad which caused me to feel anxious and fearful in her presence. I would get paid via direct deposit and I began to notice that my pay was often off (hours, days, bonuses and a raise weren’t accounted for). I lacked the skills and self-worth to be able to have a clear, direct conversation regarding money. I felt terrified to address the topic and simply put, I just didn’t know how. (Which sounds so silly to me a decade+ later, but that’s where I was at at the time.)
So instead, I did something that would forever change the trajectory of my life. I acted passive aggressively and essentially “paid myself” by using a credit card that had my name on it but was linked to the family’s account. This card was meant to buy household items and things for the children. The family found out and called the cops on me. I was arrested and confronted with a 2 year jail sentence.
The blessing:
While at the jail that day, I had one of the biggest epiphanies of my life: I heard an internal voice that said, “Caitlin, how long do you plan on keeping yourself in jail?” The external jail I was sitting in was mirroring the internal jail I was keeping myself in by falsely believing I had very little worth and thus not much to offer this world.
I realized I was done playing small. I got the message from the Universe loud and clear.
I didn’t end up having to go to jail and instead completely transformed my entire life. From that moment on, my purpose became extremely clear to me. It was evident why everything leading up to this point had to happen – the challenges in my upbringing, the childhood bullying, the never having enough money because I didn’t feel worthy of it, the feeling like a loser because I couldn’t just “get it together,” the list goes on.
Living out my life purpose:
I knew in my bones that if I could get to the root of my emotional challenges, heal myself (ongoing process, but we can get to solid baselines), upgrade my mindset and fully express my capability, then I could help others do the same. Now here we are.
2012
2013
CWC is born
In January 2013 I launched a very simple website and a Facebook business page announcing I am a Life Coach now. Caitlin Winkley Coaching is born. You’re a whattya… is what I would typically hear back then as life coaching was unheard of and not part of our mainstream culture yet. It took me a couple months to land my first client from posting an ad on Craigslist. I know… 1. I’ve obviously been dating myself this entire time, and 2. Craigslist wasn’t weird back then, ok?
I meet my mentor
I went to a self-help conference called, “I Can Do It,” put on by the mother of self-help herself, world-renowned Louise Hay. One of the speakers at the conference was a woman named Heather Dane who had a background in being a corporate executive as well as a life and health coach. I was enamored by the way she conducted herself on stage with power and mastery of subject matter while maintaining warmth and openness. I lined up to meet her after she gave her talk and asked for her business card. I called the number on the card a couple weeks later, and to my surprise Heather answered! She remembered who I was (& my hat because it turned out she loves hats) at the conference. She said she had a waitlist and was not taking on any new clients, but she saw something in me and wanted to take me under her wing.
Heather was the first person I told, outside of my family, about getting arrested. I told her I was struggling with being a life coach while having a criminal record… that once people found out, I’d be blacklisted or something of the sort. What Heather told me next shook me to my core. “Caitlin, you’ve got it all wrong. Almost going to jail is what qualifies you to be a life coach.” WOW. I had never thought about it like this prior. She was saying how could I possibly help guide others through a life transformation if I hadn’t even experienced my own.
She then told me to tell the public about being arrested. To fully own it. To share the lessons gleaned, and integrated, that then allow me to show up as a more refined version of self. With her encouragement, shaky hands and all, I wrote a blog post about it. No exaggeration, overnight, my little coaching business doubled.
2014
2016
CWC goes full-time
Within 3.5 years I was able to quit all side hustles and take CWC full-time. I swiftly built an engaged, loyal social media following who would purchase my programs and experience life-altering results. Referrals began pouring in and people were finding their way to my work in all sorts of creative ways. My books started filling as CWC was becoming popular and sought after. I began noticing the types of people who were attracted to my work tended to be high performers who wanted support with their career in addition to their personal lives. I began to naturally shift more towards working with leaders.

Next Level Life Coach Training is born
Back in 2018, I received a message that would change the trajectory of my career. An avid follower of my work asked, “how’d you do it, Caitlin?” What she meant was, how’d you build a successful life coaching business, attract an engaged audience, create powerful transformations, feel comfortable sharing yourself and your teachings publicly and charge luxury rates that sell out.
Right then, I got an idea. As an innovative thinker, entrepreneur and businesswoman, I knew what I had to do. I turned to Google and started researching life coach trainings, contacted my attorney for certification advice and began feverishly writing down everything I knew about how I ‘did it’.
What I realized is there were 3 key components that were factors to my success — 1. doing profound self work, 2. knowing how to effectively coach others and, 3. knowing how to powerfully lead and build a business. I also realized there were no other life coach trainings on the market that were comprised of these 3 elements. Of course I had to create one. Next Level Life Coach Training (formerly Soulshine) was born. I did this in conjunction with the coaching and other services I was already offering by bringing on a team.
I ran my first round of training and it instantly sold out. It continued to take off and secure a top spot in the market boasting impressive personal and professional transformations. Next Level Life Coach Training was voted as #1 of the 10 Best Life Coach Certifications That can Change Your Life in 2022 by Listly. In 2024 I decided to pivot the life coach training from b2c to b2b and now offer the Certification within organizations.
2018
2024
The pivot to organizations
After coaching leaders, business owners and corporate emerging talent for many years on their personal and professional lives, it made sense at this point in my career to pivot from b2c to b2b. I wanted to support my new direction by attending a leading business grad school for executive leadership. I chose Cornell. I love integrating the ‘pragmatic’ and the ‘higher self’ into my body of work. My clients find knowing how to navigate life and work from a blend of both energies to be extremely potent and effective.
The eagle has landed
Started from the bottom now we here. If you’re not a Drake fan (I like Kendrick too, btw), what I’m trying to say is… here I am at the helm of CWC, so proud of what I’ve created, the body of work I produce, the team I’ve built and the grit, courage, determination and cultivation of self-belief it took to get here. If you’ve made it this far, thank you so much for traveling along on the journey with me. Now, I must ask, will you and your organization be next to transform? You know the drill. Contact us. We can’t wait to work with you!