We were lucky to catch up with Caitlin Whitmoyer recently and have shared our conversation below.

Alright, Caitlin thanks for taking the time to share your stories and insights with us today. Can you tell us the backstory behind how you came up with the idea?

I never imagined I’d start my own business. Much less two of them. And then consider how many more I may also start before I die.

Truthfully? Starting a business was convenient (hold the judgment) when I first made the jump. I had reached the top of my career mountain in education, and realized the top was a bit less fulfilling than I’d expected. Turns out I missed a few warning sings, which led me into a fiery pit of burnout. My husband was soaring at his current job, setting me free from the need to financially contribute – a privilege I’ll never take for granted. Still, I worked during my so-called sabbatical. I waitressed during the week, and completed my yoga teacher training on the weekends. Eventually, I started to want to use this knowledge I’d learned about burnout and wellness and infuse it back into education. I asked myself, “If I would stay in education – how would I show up? In what ways could I truly align my vision with my values, so I don’t end up where I just did?”

That’s how Thread Education was born (Thread – for short). The inspiration came from the Yoga Sutras of Patanjali, a required text I absorbed during my YTT. The word “sutra” means “to thread,” which conceived the idea for the name of my business – well, our business. A former colleague and I had actually talked about this for about a year. So really, I just came back and told her “I found the name!!”

Naming my first business wasn’t the convenient part. The fact that I had no children, and no responsibilities other than showing up for my shift at the restaurant seemed like the most (if not best) time of a person’s life one could launch into something like this.

Thread earned its first contract. Then second, then third. But it was not yet income-worthy. Business expenses? What are those? So, in the background, I was working a contract position as a wellness coach for EdWell, a non-profit centered on teacher wellbeing that eventually became absorbed by a university due to, well, the same reasons Thread wasn’t income worthy. Nonetheless, the job was aligned with where I saw my career heading.

So I welcomed my own clients – educators suffering from burnout who wanted to fix it, for good. I started to see how gifted I was at inspiring change, which gave my brain way more ego than it needed at the time. I started looking for creative ways to grow my business. “I’ll work as a medical sales rep for this company that actually values heatlhcare, as opposed to “sick care.” I’ll use their device with my clients, and essentially function as a holistic wellness coach that can provide both physical and mental/emotional support.” I thought the idea was revolutionary – and separated me from my market. But something was off.

I was ~9 months postpartum when I told my husband, “This isn’t it. I know I thought this path was going to be my new career, but something isn’t right. I’m not making the ROI, and I’m burned out. I’m right back where I started 2 years ago.”

It was that moment where the fog started to lift, and I was finally able to look at what my business was, or more importantly, how I was building it.

I had a big “aha moment” when I realized I had been winging things. I wasn’t plugged in to the business part of my business. My first-ever mentor recommended the book, “The e-myth” to my business parter and I. I’ll never forgetting reading this line:
‘The problem is not that the business owner doesn’t know their business. The problem is that they are working in their business, not on it.’ Woof. What was I doing? No, really… what was I doing? I panicked, but the universe came in strong with the rescue mission.

Mentorship changed my life. It got me to remember:
– What I was building was worthwhile, and it needed to be protected as such.
– My true skills, my values, and my vision all had a seat at the table. I had to let each of them lead, equally.

And to realize…
– Evolving is a natural, and painful, part of entrepreneurship. Your business will respond positively if you give it room to be messy every once in a while, and let it grow alongside you (while holding on tight to your heart and your vision).

Today, I provide executive mentorship to individuals with a background in education who are evolving, in their personal lives and growing their businesses. I co-own and operate Thread Education. I teach yoga weekly. I mom every day. And I am proud of this multi-passionate, tenacious woman who trusted herself. If I hadn’t, her wildest dreams would still be just that.

Caitlin, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I always knew I wanted to be a teacher – well at least ever since I had Ms. Clayton in second grade (shoutout Ms. C!) I guess you can say I was also always destined for leadership. From running my own lemonade stand every summer as a kid, being most likely to succeed in 8th grade (no pressure, right?) and accepting a role as an assistant principal after 2 years of classroom experience – I’ve always sought out positions where I see a problem + want to fix it. I believe good leaders have the vision for this.

So – the problem I first aimed to fix when founding Thread Education was the ginormous elephant in the room that no one seemed to want to talk about: teacher wellbeing and retention. Living in a far right state has amplified this mission, as Florida is ranked #50 in the nation, and the average teacher salary is $7k below the livable minimum wage. In order to disrupt these systems, I believe its important to empower the leaders in the field, who have the platform to shift the culture of their schools, and advocate for better working conditions, which include more opportunities for sustainable leadership, protected planning time, clear communication, and systems that don’t run schools into the ground.

Through Thread Education, I help school and district leaders reclaim their wellbeing, restore clarity, and take courageous action that transforms not just their school culture – but their personal lives, too. We (my brilliant co-founder and I) do this through executive coaching, strategic consulting, and professional development rooted in real research and lived experience.

But that’s only half the story.

The second business I founded + run – Hand & Health Wellness – was born from the moment I walked away from traditional leadership and realized I could bring my passion for transformation outside the system. That’s where I support current and former educators in building aligned, integrity-driven businesses, or pivoting into careers that match their values, energy, and goals.

What sets me apart is simple: I’ve lived (and continue to live) what I teach. I’ve burned out in roles I thought were “dream jobs.” I’ve coached leaders through massive career transitions, supported schools through cultural revolutions, and built two businesses from the ground up while building my family, conceiving our first son in the same month Thread Ed. was birthed. I’m not here to hand people a rigid playbook. I help them build their own, rooted in nervous system-led strategy, wellness, and freedom.

I’m most proud of the ripple effect. When a leader sets boundaries, builds confidence, and reclaims their joy… everyone around them benefits.

At the end of the day, I want people to know this: you don’t have to choose between your mission and your wellbeing. You can lead and feel human. You can grow and feel grounded. And you don’t have to do it alone (nor should you try to!)

Can you share a story from your journey that illustrates your resilience?

Resilience, to me, isn’t just about pushing through – it’s about surrendering what no longer serves you so you can make space for what’s truly meant for you.

One of the clearest examples of this in my life was our journey to conceive our son. It took two years: two years of hope, grief, tests, and trying. And in that time, I realized the biggest work wasn’t external. It was internal.

I had to release a lot of old beliefs, pressure, perfectionism, and control. The same things I now help my clients release as they build careers and businesses aligned with who they really are.

The turning point came when I shifted my belief that this baby would only arrive on my timeline. I started to believe (deeply) that he already existed. Just like the businesses, breakthroughs, and transformations I see in my clients every day… he already existed, just in another dimension of time.

Acupuncture helped. So did my brilliant life coach (who deserves her own spotlight – shoutout to Hillary Talbott-Roland, owner of Art of Acupuncture). But the real shift was when I made space – emotionally, mentally, spiritually – for him to arrive.

And he did! In the middle of a category 4 hurricane. A true Florida man!

This experience cracked me open. It taught me the power of preparation, of faith, and of clearing the path. And it’s why I now teach others how to create space – not just in their schedules, but in their systems, nervous systems, and beliefs. THIS is what creates the opportunity for a person to call in what they’re meant to create next.

And in my opinion, that’s resilience: not forcing something into place, but clearing out what’s blocking it from flowing in.

Any advice for growing your clientele? What’s been most effective for you?

Integrity and authenticity. People can sniff desperation and insincerity from a mile away—and although I try to assume positive intent when I receive cold messages on LinkedIn, many of them come across as transactional or disconnected from who I am.

The most effective strategy I’ve used is actually not trying to “sell” at all. Instead, I focus on building real relationships, being of service, and sharing my journey openly- especially the messy, behind-the-scenes parts. When people feel seen, understood, and respected, they naturally lean in.

That said, I don’t shy away from selling. In fact, my conviction in what I offer has been a massive lever for my business growth. I believe deeply in the transformation I help my clients create – and that belief shows up in how I talk about it. Sales, for me, isn’t pressure. It’s service with clarity. And that level of certainty is often what inspires people to say yes.

Aligned clients don’t need to be convinced. They need to be invited into a conversation that feels human. And that only happens when your brand and your outreach are rooted in values, not just outcomes.

Contact Info:

• Website: https://www.handinhealthwellness.com
• Instagram: hand_in_health.wellness
• Linkedin: https://www.linkedin.com/in/caitlin-whitmoyer-m-ed-331087b0/

Image Credits

Jordan Torelli Photography