Today we’d like to introduce you to Jennifer Donaldson.
Hi Jennifer, we’d love for you to start by introducing yourself.
I’m a teacher, tutor, and tailor of joy! I am always teaching something, somewhere, because that’s where I thrive. My love for teaching began as a child playing school and eventually became a career in elementary education. I am now a tutor, a job I love. After earning my degree from Liberty University, I spent the past 30 years teaching in classrooms, writing curriculum, subbing at many grade levels, volunteering with youth and ESL at church, drinking coffee, and privately tutoring students.
My husband and I have lived in the Raleigh area for over 25 years and raised our daughters here. Intentionally seeing joy in everyday life has been my goal for many years. Joy is a gift from God. It helps me smile more and sigh less. I have learned that my circumstances might not change, but my attitude can. It makes a huge difference in how I live and teach.
When life shifted and I stepped away from full-time classroom teaching to care for my aging parents, I knew I still needed meaningful, flexible work within education. That’s when I took what I loved and launched Tailor Joy LLC. I started small, doing everything myself, from setting up the LLC to building the website, marketing, and writing many blog posts. As my business grew, friends began asking for advice on starting their own tutoring or coaching businesses, and that’s how my affordable Business Basics course was born.
Today, I tutor students in grades 3–10 who need help with reading, writing, and study skills. My clients include students from WCPSS, private schools, online schools, homeschools, and international schools. My favorite sessions are book discussions that help students unlock comprehension and build confidence. I also coach adults building their education-based businesses.
Through my positive experiences volunteering in my church’s ESL program (English as a Second Language), I’ve expanded my tutoring services to include conversational English practice for teens and adults. I’m also getting ready to release a new workshop to help entrepreneurial teens and their business mentors work through ideas together. I love my job!
Tailor Joy LLC is about more than academics. It’s about helping people smile more and sigh less. Whether I’m guiding a student through a complicated novel or helping a new entrepreneur sketch out their next business step over coffee, my goal is the same: to nurture growth and confidence, spark joy, and teach with purpose. I’m excited for what the next 30 years in education will look like for me and the students I will meet.
We all face challenges, but looking back would you describe it as a relatively smooth road?
Teaching in the elementary classroom was meaningful work, but being confined to the school building all day became increasingly difficult, especially as my aging parents began needing more help. The pressure of balancing full-time teaching with family caregiving was simply too much. Like many in the sandwich generation, I had to make a hard choice. I left classroom teaching and returned to tutoring.
It wasn’t a smooth or instant transition. Business started slowly, and my early clients were a mix: a homeschooled student studying Roman history, a young student with autism, and a college student recovering from a stroke who needed conversational practice. The variety taught me how to adapt quickly and manage smooth transitions between sessions, even if that just meant reheating my coffee in the two minutes before the next student arrived.
As my business grew, I built systems that now make my days run smoothly: a digital slide deck organized by semester, filled with resources and lesson tools, and a well-stocked “go bag” so I can tutor on the move—from a doctor’s office, hospital waiting room, or even an airport. Emergencies still come up, but owning my business means I can flex my schedule when needed without the stress of writing sub plans or taking a whole day off. My clients know I’ll do the same for them when life happens.
Another challenge was launching online tutoring before it became common. I saw its potential and tried it out with one student, but most families preferred in-person sessions. When the pandemic hit, I quickly transitioned all clients to Zoom and offered a few free sessions to help skeptical parents adjust. Because I already had consistent routines and relationships in place, I didn’t lose a single client. I simply became a familiar face on a screen instead of across the desk.
Now, I tutor from wherever I am: home, coffee shops, my daughter’s guestroom, or while traveling. I love my job! My flexible online format and personalized, engaging style have helped me connect with a wide range of learners. It hasn’t always been easy, but the challenges have made my business stronger, more mobile, and more sustainable for my life and my clients’ needs.
Appreciate you sharing that. What should we know about Tailor Joy?
At Tailor Joy LLC, I help students find confidence and joy in their education, and I help adults start tutoring, coaching, or lesson-based businesses they love. I’m both the founder and lead educator, and the name Tailor Joy is a reminder to intentionally notice joy in everyday life. You don’t manufacture joy, but you can learn to see it, even in the hard moments. Especially in the hard moments.
Whether I’m working with a student struggling in school, a new English speaker, or a teacher launching their own tutoring business, my goal is the same: to help them gain practical skills and self-confidence. Confidence to speak up in class. Confidence to send a professional email. Confidence to run your business. Confidence to ask the hard teacher for help. Confidence to advocate for yourself, kindly and clearly. Confidence to give the presentation. Confidence to ask the hard questions.
That’s what I want for every client: to smile more and sigh less.
Are there lots of sighs in your house in the afternoons? If you are tired of the lack of harmony at home when it comes to homework time or not seeing joy in your child’s educational experience, reach out to me. Maybe it’s time to change some routines at home, or maybe it’s time to hire a tutor. Tutors help students improve grades, manage workload, strengthen academic and critical thinking skills, reduce stress, and cultivate a healthy attitude about education. All of these help a student to gain confidence at school and at home, ensuring they are prepared for the next grade and beyond.
I specialize in:
Tutoring students in grades 3–10 in reading, writing, and organization skills
Conversational English practice for adults
Business courses for educators starting tutoring businesses
Educational resources and printables for families and tutors
Blog posts with lots of helpful resources for parents and fellow tutors, such as https://tailorjoy.com/time-management-for-kids/
A free weekly newsletter, Two Minutes Together
What sets me apart? I combine a teacher’s heart with a coach’s mindset. I bring structure and flexibility. I show up prepared and professional and also warm, witty, and real. Some of my best ideas are a little outside of the box, just like my logo. I build safe spaces where hard conversations and real learning can happen. My family and clients will tell you that I always have an intentional question ready to get people thinking and talking, such as “Are you more like a pencil or a school bus?” or “What’s one thing you don’t know how to do but wish you did?”
I invest time getting to know my clients, understanding their unique challenges, and helping them build skills they can use for a lifetime. That kind of personal, thoughtful support can’t be automated by AI. It’s what classroom teachers wish they had more time to do, and it’s what I get to do every day.
I love my job, and I love seeing that moment when “the light comes on” for a student or business client. That spark, that grin of understanding or confidence, that’s what I’m most proud of when I think about my clients and my business.
My free weekly email, Two Minutes Together, is filled with practical encouragement on a variety of topics, including education, parenting, multigenerational living, lost luggage, and tailoring joy in everyday life. It’s short enough to read while you are waiting for your coffee order.
Don’t worry, you, too, can grab a cup of coffee and catch up on all my blog posts, free tools, and a bit of joy at www.tailorjoy.com. You can also sign up for my free newsletter and get a month’s worth of conversation starters.
Can you talk to us about how you think about risk?
I’m a risk taker to a degree. I like to research my options, create a flexible plan, and then try it out. I’m not reckless, but I’m also not afraid to pivot when needed. That blend of preparation and adaptability has served me well in both life and business.
One of the biggest risks I’ve taken was starting Tailor Joy LLC. I left a full-time teaching job without a mapped-out future, knowing only that I needed work that fit my season of life and still allowed me to do what I love: teach. I didn’t have a business plan, an elevator pitch, or branding. But I got started anyway, and I learned as I went. That risk turned into a thriving business.
In the business world, people talk a lot about “finding your niche.” The risky part? I have several. I couldn’t choose just one specialty, and I still don’t want to. I love private tutoring, but I also love coaching, writing, and speaking. One day, I’m talking with a local student about their book report. The next, I’m talking with expat families about international schooling or writing about carry-on travel with my mini coffee pot. If I had to name my niche, it’s helping people find joy and confidence in everyday life, whether that’s in school, on an airplane, or in a waiting room. I love my job!
I also promote risk-taking with my students. I coach them to respectfully advocate for themselves, whether that’s asking for more time on an assignment or clarifying a confusing direction with a teacher. I remind them: the teacher might say no, but they also might say yes. You won’t know unless you ask. Sometimes, the smallest risks can lead to the biggest growth.
For me, risk isn’t about jumping in blindly. It’s about believing that something better is possible and being willing to take the next right step, even if the outcome isn’t guaranteed. Sometimes those risks provide me with perfect opportunities to notice and talk about the joys in my everyday life.
I’ve got a question for you. “What risk has brought you the most joy?”
Pricing:
- Private tutoring for grades 3-10 in reading, writing, and study skills or Adult ESL: $60/hour
- Business Basics course: $399
- Printable educational resources and art: all under $10, some free
- Tailoring joy in everyday life: priceless
- Visit my website for more details: https://tailorjoy.com/
Contact Info:
- Website: https://tailorjoy.com/
- Instagram: https://www.instagram.com/tailorjoy/
- Facebook: https://www.facebook.com/tailorjoytogether
- LinkedIn: https://www.linkedin.com/in/jenniferjdonaldson/
