How Jennifer Dutton Grew a Thriving EF Coaching Business on Top of 25 Years as an Occupational Therapist
- Sean G. McCormick
- Jul 2
- 12 min read
Thinking about leaving a stable career in education or therapy, but unsure whether your skills will carry over or whether the clients will actually come?
Jennifer Dutton knows that feeling well.
After more than 25 years as a school-based occupational therapist, Jennifer walked away from a secure leadership role without a clear plan, burned out from managing adults and drifting further and further from the work she loved most: helping students.
A single, unplanned coffee chat changed everything.
Jennifer got certified at EFCA and is now the founder of Connect 2 Learn, a thriving executive function coaching practice where she works with families and school districts all while continuing to practice as a licensed OT and staying fully in control of her own schedule.
In this interview, Jennifer shares how she pushed through the “crickets” stretch every new coach dreads, learned to recognize her own value and price accordingly, embraced the unknown, and built a practice that lets her be the driver of her own time.
If you prefer to watch the video interview, you can do that here.👇
What is Jennifer's Background?
Jennifer Dutton is the founder of Connect 2 Learn, where she helps students build the executive function skills they need to feel confident and capable — in school and in life.
Before launching her coaching practice, Jennifer spent more than 25 years as a school-based occupational therapist, including several years in a leadership role supporting OTs and other service providers across school districts.
She is a licensed occupational therapist, recently completed an ADHD certification for service providers, and is a certified Executive Function Coach through the Executive Function Coaching Academy.
Today she lives in “both worlds,” blending traditional OT work with executive function coaching for students and families, and partnering with school districts to support their staff.
You can learn more about Jennifer's practice at connect2learnllc.com
Here is the full interview👇
1. What were you doing professionally right before you started your EF coaching practice?
Prior to jumping into the certification course, I was a school-based occupational therapist for 25+ years.
Within those years, I also had the opportunity to step into a management position, where I supported occupational therapists and other service providers within school districts.
So I came into this work with a deep background not just in direct student support, but in the operational and business side of running services, too.
2. What made you decide to pivot from occupational therapy to executive function coaching?
Honestly, I really didn't have a clear direction when I left.
I left my position because I was truly burned out from managing adults and being so involved in the business side of the company.
I realized I had moved farther and farther away from my passion, which was working with students.
So I left without a true direction.
And the real turning point for me was an unplanned coffee chat with a fellow mom in my community whose background is in school psychology.
We had this really great, authentic conversation about executive function skills — what they mean for students, and how much they impact a child's success and their challenges in school.
From that conversation, I had some real aha moments:
Can I do this? Could I do this? I think I can.
And right in that same time frame is when I came across the Executive Function Coaching Academy.
3. You knew the security and predictability of the school system. What was the hardest part about stepping away from that?
The hardest part was exactly that — the predictability.
I came from a space where the day is planned and the targets are understood.
Whether I was working directly with students or leading a team, I knew what the goals were, I knew where I was going, and my day was set up for me. I
had an eight-to-five workday and I really knew what was going to happen.
Moving into a space with a lot of unknowns where I couldn't see the clear pathway can be pretty fearful.
A big shift for me was being okay with the unknown and embracing it — looking at it as this can be exciting.
Not knowing everything, not having all the answers, is okay, because it can open doors.
And it wasn't just me to consider.
I have a family and a partner, so this wasn't a situation where I could just do whatever I wanted whenever I wanted.
Making this kind of investment and going through the process really is a big step.
4. What drew you to the certification program specifically, and what shifted once you enrolled?
I've always had a lot of ideas.
I really enjoy generating them and I love the creative side of that.
But what drew me to the course was that it had very specific tools related to business development — looking at things as a business owner and getting clear on that side of things.
On top of that, there were tangible tools I could use the very next day, directly with students and directly with families.
That's what helped me move from idea-based thinking to action-plan thinking.
5. What did the timeline look like from your first “aha” moment to your first paying clients, including the quiet stretch in between?
The conversation that started it all happened in late summer.
I actually had the chance to work one-on-one with a student before I even had a solid name for the business or a website.
A few months later, I took the course.
Then I developed my website and my logo, and I'd say I launched about five or six months after that initial conversation — roughly a month after finishing the course.
And I thought people were going to be knocking down my door.
It was crickets.
That's when the fear sets in, the anxiety, the worry.
But I recognized that you just have to show up.
Show up every day, put in the work, and keep moving forward, even if it's a tiny step on a given day.
About three months in, it went from one or two students to five or six.
It was a slow build at the beginning.
And within one year, I had roughly eight to ten students a week — plus I'd started working directly with school districts, both through direct student work and by providing professional development to their staff.
6. What helped you go from crickets to a steady flow of students and even school district contracts?
It comes back to doing a little bit of work every day — and being willing to try all the things to fine-tune what actually works for marketing.
I'm in a small community and a small state, so I leaned into as many business networking opportunities as I could find.
I did formal outreach, signed up for networking luncheons, met with other small business owners, leaned on professionals in the marketing space, and even worked with someone to run Facebook and Instagram ads.
Here's what surprised me: the ads were the least helpful.
I don't think a single direct client came from them. They may have increased visibility, but that was it.
What actually drove clients was word of mouth and the close-knit community groups I'm part of on Facebook, along with local parent groups.
That's what created a steady flow of incoming students and families.
But the networking wasn't wasted — it helped me develop my elevator pitch, which is something Sean teaches in the course.
Getting clear on what I wanted to say meant I could take advantage of unexpected conversations in the community.
I'm at a soccer game or a basketball game, a conversation comes up about our kids and school, and I say, “Oh, hey — I do this.”
It might not be for that family, but they remember it, and they share it with a friend.
7. You talk about an “identity shift.” How did seeing yourself as an EF coach change the way you grew your practice?
It's so relatable for parents — and that makes it an easy conversation for everyone to have.
Every parent has experienced the student who calls because they forgot their computer at home, or whose homework sits on the table as they run out the door three out of five mornings.
The content is genuinely relatable for families.
So when I started introducing myself as someone who helps students with executive function skills at the soccer game or at the basketball game, it just landed differently.
Anyone with a kid is already thinking about how their child is doing in school.
When you shift your identity to “I'm an Executive Function Coach,” you start to share that and it's almost magnetic.
8. A lot of coaches doubt whether this can be financially viable. How did you build a practice that supports you even through slow seasons?
The first thing is really being sure that you recognize your value so that you price yourself correctly.
Sometimes people feel like, “Oh, I'm not providing anything that great, I'll charge X.”
You have to get comfortable being uncomfortable here.
Recognize the value you bring to students and the behind-the-scenes work you're doing, and make sure your rate reflects all of it and meets your financial needs.
It's okay to put yourself first when you make that decision, and to shift away from treating this like a hobby.
A lot of EF coaches come from education or from service-provider backgrounds — OT, speech-language pathology — and they have such a strong ability to connect with students.
Don't lose sight of that value.
I also built my rate to account for the fact that you need time off to recharge.
That might align with the school calendar — spring break, winter break — but you've built an hourly rate that supports that time off.
Be your own executive function coach: pay attention to the lulls, budget for them, and plan ahead. It's doable.
When Sean and I did our one-on-one coaching for that full year afterward, I set a specific financial goal — and I reached it.
In full disclosure, not every single month do I hit that number; there's some ebb and flow, because life is life for families and things change.
But I'm right there, consistently achieving it.
9. You now work in “both worlds” — OT and EF coaching. How do those two fit together?
I maintain my occupational therapy license in my state, so I've been able to keep doing more traditional OT work alongside my coaching.
I actually thought I was going to walk away from OT, because I absolutely love executive function coaching.
But you know what?
I can live in both worlds quite easily.
The two are so interconnected that it's been really nice to have both pieces as part of my week-to-week workload.
10. Beyond income, so much of this is about flexibility. How has your sense of ownership over your time changed?
In some ways I work a lot of hours a day — but I'm in full control of those hours.
I have these pockets of time during the day that I never had before, when my schedule was dictated by someone else.
I can take an exercise class from 10:15 to 11:15.
I can walk my dog at one o'clock because it's beautiful and sunny.
I can pop into the grocery store mid-week when it's quieter.
I don't take that gift for granted.
It's been really nice to be the driver of my own time rather than having it dictated for me.
I've even been able to keep dance as part of my life, which I love.
11. Executive function coaching has no preset curriculum the way teaching does. How has your confidence with challenging students evolved?
At first, I felt like students already knew what worked for them — they had their systems and I couldn't change them.
Families had a certain way of doing things, and maybe I could just help a little. I was more hesitant.
But as I grew into my identity as a coach, my confidence grew with it.
I recognized that I could not only provide usable tools and strategies, but also understand each student's unique challenges and their unique gifts — and create a customized approach that's actually meaningful to them.
A huge part of that is buy-in.
The student has to feel that these tools will benefit them and help them feel better about their life as a student.
Once I recognized that, the work really took off.
I don't have to walk in with a stack of lesson plans and feel like I have to fill the time.
It can be more authentic, at the student's pace, and customized to their needs.
12. What would you say to an OT — or any licensed professional — who feels buried in paperwork and wonders if there's something more?
I'd tell them to reflect on what they're already doing for their students, patients, or clients — and to recognize that it is easily transferable to the world of executive function coaching.
A common motto in OT is “skills for the job of living.”
As an executive function coach, you can look at it through the lens of “skills for the job of learning” — but really, you're still focusing on skills for the job of living, because those are the skills students need to be successful.
And yes, there's still paperwork.
But as a coach, the paperwork is meaningful.
It represents real collaboration and communication with families and teams — not just “I have to write this down.”
Everything is so student-centered that you no longer mind doing it.
It's easier than you think it is.
Don't let fear be the barrier — that's all it is, a mental block.
The excuses for why you can't do it are the thing you have to swerve around.
13. There's no single governing body for EF coaching. How did you learn to trust your own expertise and sit in your authority?
Oh, for sure that comes up — and honestly, it still bubbles up sometimes.
I think that's what makes us human.
We talk to our students about looking ahead toward goals, but also about reflecting.
That's a huge part of this process: reflecting on your own skill set and life experiences, and on the time you spent with a student.
It's okay to ask, “What could I have done differently?” while also recognizing your strengths.
It's so much more than a set of letters, or a license, or a certification.
It's really just doing the work — the same way you ask your students to do the work.
We all have our moments.
You're tired, or something's going on with your family, or you're working with a new student who's hard to reach, and you start to question whether you're really making an impact.
So you use a little self-talk:
Okay, strap on the boots. Put on your big-girl pants and move forward.
Honor the feelings, but recognize your skill set, too.
14. Where do you see your business and your work going next?
The old me — or even the more recent me — would say I have to have a plan, and it has to be written down.
But I'm going to say, with confidence: I don't know. And I'm okay with that.
I'm just going to be open to what's next, and more thoughtful about what speaks to me — what's aligned with the way I work with students and the level of support I want to provide.
There's a shift happening, and there's time and space for me to sit with it — hopefully this summer, when things are a little quieter.
Right now, it's just about being open to the possibilities.
15. What's one piece of advice you'd give a coach who's just hit that first quiet, “crickets” stretch?
Step one: don't panic.
Keep doing the work.
I think of it as a few parallel pathways.
Do the work, and be a lifelong learner — keep looking at resources.
If you haven't taken the certification course, take it.
If you have, keep using the tools it gives you.
Make connections with other new coaches in the same space as you.
That camaraderie and communication is a wonderful experience and a great tool. Keep learning, keep refining your message and what you share.
Don't let fear freeze the forward motion.
Keep putting in the work and keep talking to people.
16. What's one tool that's been indispensable in your journey?
I have two.
From a business perspective, TutorBird has saved me so much time and helped me manage the behind-the-scenes structure of the business.
It's been a wonderful tool to have.
And Canva has been super helpful for creating everything from slide decks to customized tools for students.
Those two — along with my Google Workspace — are the tabs that always stay open.
Thank you Jennifer!
Jennifer's story is a powerful reminder that the skills you've already built — whether as an occupational therapist, a teacher, or another service provider — are far more transferable than you think.
Her journey is proof that you can step into the unknown, push through the quiet early days, honor your own value, and build a practice that supports both the students you serve and the life you want to live.
You can learn more about Jennifer's practice at connect2learnllc.com, where you can read about her coaching and fill out her contact form to connect directly.
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About Jennifer
Jennifer Dutton is the founder of Connect 2 Learn, where she helps students build the executive function skills they need to feel confident, capable, and in control of their academic lives.
She is a licensed occupational therapist with more than 25 years of school-based experience, including a leadership role supporting OTs and other service providers across school districts.
She recently earned an ADHD certification for service providers and is a certified Executive Function Coach through EFCA.
Today, Jennifer blends traditional occupational therapy with executive function coaching for students and families, and partners with school districts to support their staff through professional development. Her approach is customized, student-centered, and built around buy-in — helping each student feel that the work is genuinely theirs.
Connect with Jennifer👇
Website: https://www.connect2learnllc.com/