We recently connected with Ashlee Nicholas and have shared our conversation below.
Ashlee, first a big thank you for taking the time to share your thoughts and insights with us today. I’m sure many of our readers will benefit from your wisdom, and one of the areas where we think your insight might be most helpful is related to imposter syndrome. Imposter syndrome is holding so many people back from reaching their true and highest potential and so we’d love to hear about your journey and how you overcame imposter syndrome.
When imposter syndrome showed up for me, it was during the second month of running the Quit Teaching Club. A ton of new people started joining all at once, and instead of feeling excited, I felt this sudden anxiety. I remember thinking, “Why are they listening to me?” Even though I had left teaching myself, found a job I truly love, and had already spent years helping teachers and paras transition into new careers, it still made me question whether I was qualified enough.
I had to intentionally shift my mindset. I reminded myself that I’m not just qualified on paper — I’m good at the things that matter most in this work. I’m good at connecting with people, helping them feel supported, and guiding them through a process I understand personally.
Someone I admire once said that if you have knowledge that can change people’s lives, you have a moral obligation to share it. That idea has stuck with me. It helped me see that this work isn’t about being perfect or having every answer. It’s about showing up for people who are scared, overwhelmed, and trying to figure out what’s next. It’s about using my experience to make their path a little easier.
Once I started viewing what I do as something I’m meant to share, the imposter syndrome lost a lot of its power. I still have moments of doubt, but now I remind myself: I’m here to help, and that’s enough.
Thanks, so before we move on maybe you can share a bit more about yourself?
The Quit Teaching Club is a one-stop space for educators who want community, emotional support, and clear guidance through the entire process of leaving the classroom. It’s the place I wish I had when I was a special education teacher and a mom trying to figure out how to build a new career. Inside the club, I help educators work through their limiting beliefs, choose job titles that fit their experience, write resumes that actually open doors, search for jobs, prepare for interviews, and eventually learn how to thrive once they transition into a new role.
What motivates me is remembering how overwhelmed, stressed, and confused I felt during my own job search. I don’t want anyone else to walk that road alone. I get to be their guide, their support, and their hype girl while they rebuild their confidence and imagine a future that actually feels good. I’m not changing lives — I’m helping people step into the lives they were meant to live, and there is something incredibly beautiful about that.
What makes The Quit Teaching Club special is that it’s not just another “coach” handing out a $500 PDF and disappearing. I’m actually teaching educators real, practical skills that help them help themselves. I’m in the trenches with them — answering questions, celebrating wins, and reminding them of their strength when they forget it. My members tell me all the time that what they value most is the moral support, the honesty, and the feeling of having someone in their corner who genuinely cares.
I’m most proud of the way this work helps people heal. I’ve watched burnt-out, discouraged, and even physically sick educators find new careers that reignite something inside them. Seeing hope return to someone who thought they were out of options never gets old.
This entire journey was unplanned. I posted about my experience leaving teaching one day, and suddenly my inbox was full of educators asking for help. It felt like a calling I didn’t expect — one that I’m grateful I listened to.
Right now, we’re expanding quickly. We’re building out a full library of Sprint Trainings, and by the time this article goes live, we’ll have launched our very own Job Board where we share openings that are a great fit for educators. In the coming months, I see the Quit Teaching Club growing with more members, changing more lives, and continuing to be a safe, empowering place for educators who are ready for a new chapter — and ready to believe in themselves again.
There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
Looking back, the three qualities that made the biggest difference in my journey were authenticity, compassion, and my lived experience as an educator who went through this transition myself.
Authenticity matters because I’ve always believed in telling the truth, even when it’s uncomfortable. I ask people their minimum salary requirement, and if it’s not realistic for the roles I can help them with, I tell them that upfront. I think people appreciate that level of honesty — it builds trust. It shows them that I’m not here to sell a dream; I’m here to guide them through a real process. If someone wants to develop authenticity, my advice is to stop trying to present a “perfect” version of yourself. Say the things you actually mean. Be transparent. People connect with real far more than they connect with polished.
Compassion has been just as important, because this process is emotional. Leaving education isn’t just switching careers — it’s grieving an identity, facing fear, and picturing a completely different future. My compassion helps me understand the layers of what people are going through, especially when they resist the changes they know they need to make. If someone wants to build compassion, my advice is simple: actually listen. Pause before you respond. Try to understand what someone is feeling, not just what they’re saying. Compassion starts with slowing down enough to truly see people.
And honestly, my lived experience has been one of my greatest strengths. I’ve been exactly where my members are — overwhelmed, guilty, unsure, stressed, hopeful, scared, all of it. I know what this transition feels like in your body. I know the guilt educators carry, and how heavy the decision is. Because I’ve lived it, I can guide people through it in a way that’s grounded and real. For anyone who wants to develop this kind of knowledge, my advice is to lean into your own story. Your experience — even the hard parts — can become something powerful when you use it to help someone else.
If I’ve learned anything, it’s that you don’t need to be perfect to make an impact. You just need to be real, compassionate, and willing to use what you’ve lived through to help the next person up the mountain.
What has been your biggest area of growth or improvement in the past 12 months?
Over the past 12 months, my biggest area of growth has been learning how to take care of myself instead of automatically putting everyone else first. I’m a deeply empathetic, compassionate, giving person, and for most of my life that meant I poured into everyone around me while ignoring my own needs. This year, I finally started turning some of that energy inward.
I’ve been focusing on my physical health, but even more importantly, I’ve been doing a lot of mindset work. I’ve been learning how to believe in myself, how to slow down, how to show myself the same love and encouragement I give to everyone else. I’ve had to practice letting myself be human, trusting my intuition, and showing up authentically — not just for my community, but for myself.
It hasn’t been easy, but it’s been transformational. I’m finally learning that taking care of myself isn’t selfish; it’s necessary if I want to keep helping others in a meaningful, sustainable way.
Contact Info:
- Website: https://www.skool.com/the-teacher-transition-club-6451/about
- Other: TikTok: @quitteachingclub
Image Credits
None, but I would like to add that I have built this business from my car and my local coffee shop – which is why I chose these images. 🙂
so if you or someone you know deserves recognition please let us know here.
