Jennifer Donaldson
https://tailorjoy.comWith a 30-year teaching background, Jennifer got a renewed sense of purpose - emerging more focused, confident, and ready to grow.
“When you’re self-taught, sometimes you jump in without knowing the why behind what you’re doing. These courses gave me that why.”
For over three decades, Jennifer built her career around teaching - both in the classroom and through private tutoring.
But when she retired from the school system to care for her aging parents, she knew she wasn’t ready to fully stop working. Instead, she leaned into the part of her job she loved most: building confidence in others.
“I tell people I’m a teacher, a tutor, and a tailor of joy,” she says. “Whether I’m helping a child with reading or coaching an adult learning English, what I’m really doing is helping people believe in themselves.”
Jennifer formalized her business five years ago by creating an LLC, but as she branched into new services like tutoring adults in conversational English and coaching other educators, the back-end of her business started to feel overwhelming.
She knew what she wanted to do, but didn’t know how to prioritize it all.
That’s when she joined the GeekPack + Verizon Small Business Digital Ready Cohort.
At the time, Jennifer described herself as being “at a crossroads.” With so many competing responsibilities and business ideas, she needed structure and support to actually make progress.
“I needed a refresher in all the different areas of my business - and the kick in the butt to actually do it,” she explains.
The cohort gave her exactly that. With a clear timeline, weekly accountability, and access to practical, bite-sized courses, Jennifer finally set aside time to work on her business instead of always working in it.
One of her biggest breakthroughs came after completing a course exercise that prompted her to list everything on her mind.
“I did this ginormous brain dump of everything that was keeping me up at night - over 200 items,” she recalls. “Then I dumped it all into ChatGPT and asked it to organize it. That was a huge win.”
That clarity, paired with the OKR (Objectives and Key Results) framework introduced during the cohort, helped Jennifer zero in on what mattered most. Instead of feeling scattered, she could now focus on one key area of her business at a time.
While Jennifer didn’t enroll expecting overnight results, the long-term impact was clear from the start. The courses didn’t just give her new knowledge - they gave her confidence in what she already knew.
“I really can do this. I was thinking of hiring someone to redo my website, but it’s so expensive. Now I realize I can do it myself,” she says.
Courses like Selling with Storytelling helped her reframe her messaging to focus on the customer journey, not just her own services. Others reminded her of best practices she had picked up along the way but never fully understood.
Jennifer also credits much of her progress to the supportive environment of the cohort - particularly Glenna Garcia, her cohort leader.
“Glenna was hysterical, down to earth, and gave you a kick in the butt when you needed it,” Jennifer laughs. “But she also went above and beyond. Her feedback was so specific and helpful - it wasn’t just ‘improve this,’ it was how to improve.”
The community and accountability helped Jennifer complete over 17 Digital Ready courses, more than she ever would have tackled on her own.
Jennifer feels more equipped and energized than ever before. She’s actively working on redoing her website with a more customer-focused approach, using what she learned in the cohort.
And even with a tight budget, she’s planning to rehire a contractor to handle smaller tasks - freeing her up to focus on the bigger-picture projects that will grow her business.
“I know the time I’m putting in is going to be worthwhile,” she adds. “The return on investment is going to come.”
Jennifer’s biggest lesson from the cohort?
“Just try it. You don’t have to be perfect to start something - make mistakes along the way and improve as you go.”
From an educator overwhelmed by to-do lists to a business owner with clear focus and confidence, Jennifer’s journey is a powerful reminder that sometimes the right structure and support can unlock what you already had within you all along.
Can you share a quick overview of your business?
I'm a teacher by training, certified for over 30 years. Throughout my career, I've stepped away at times to raise my kids or care for family and always returned to education in some way. When I retired to care for my aging parents, I still needed income, so I started private tutoring. About five or six years ago, I made it official and formed an LLC.
Now I say I'm a teacher, a tutor, and a "tailor of joy." I help build confidence—whether it's a child struggling with reading, an adult learning English as a second language, or coaching teachers who want to start their own tutoring businesses. It's all about building people up.
How long have you been in business or worked in this role?
This version of my business started about 13 years ago when I left the classroom. I formed the LLC around five years ago.
Do you have any employees or team members (if so, how many)?
It's just me. I've hired contractors off and on, but for the past year, it's been a solo operation.
What problems were you looking to solve by signing up for the GeekPack + Verizon Cohort?
I was at a crossroads—expanding into tutoring adults while still working with students. I needed to set aside time to focus on the behind-the-scenes business work, like updating my website. The cohort's structured timeline and weekly commitment gave me the push I needed. It felt like a comprehensive refresher across different business areas, not just one topic like social media.
Have you tried to learn about improving your digital presence before?
Yes. I'm entirely self-taught and have always valued digital presence. The cohort wasn’t my first exposure, but it helped me fine-tune what I already knew and gave me helpful context about why certain strategies work.
Have you seen any tangible returns (more money, more customers, client feedback) from implementing what you learned?
Not yet, but I’m anticipating it. One major takeaway was doing a massive brain dump of over 200 things keeping me up at night—everything I needed to do to grow. I used ChatGPT to categorize and prioritize those tasks, then aligned them with my business focus using the OKR framework from the cohort.
I’m confident the return on investment is coming—I now have the clarity and motivation to act on what matters most.
Do you feel more confident with digital skills for your business than you did before?
Yes. Courses like Selling with Storytelling helped me understand how to focus on customer needs rather than just promoting myself. The content around website accessibility and growth marketing was also valuable. Even when I already knew something, the cohort explained the “why” behind it, which really clicked for me.
What were your biggest challenges during the cohort or with the courses?
Personally, I didn’t struggle much with the coursework itself. The bite-sized format and flexibility made it easy to fit into my busy schedule—even when I was traveling internationally.
What else would benefit your business for you to learn?
I'd love more guidance on hiring contractors or even employees. As a small business owner, it’s hard to know what to pay, how to vet people, or even where to find them—especially if you don’t have a network of other business owners.
Did you feel supported when going through the Digital Ready courses and being part of the GeekPack cohort community?
Yes. Glenna Garcia was fantastic—supportive, down to earth, and very present. Her feedback on our work, especially OKRs, was thoughtful and specific. She didn’t just say “improve this,” she showed how to do it. Even during holidays, she modeled balance, encouraging us to prioritize family while still engaging in the work.
Did joining the GeekPack cohort help with your progress in the Digital Ready courses?
Absolutely. I’ve completed over 17 courses—far more than I would have without the cohort. The accountability helped me explore topics I might’ve skipped otherwise.
What was your most impactful takeaway from your time in the GeekPack cohort?
Two things:
In your opinion, what is the most valuable part of being in the Cohort?
Accountability. It pushed me to actually do the work—whether that was completing courses or making real progress on my business.
What's your number one tip for someone who wants to learn a new skill/move forward in their business?
Don’t be afraid to just try. You don’t have to be perfect to start—just get going and improve along the way.
What does the future look like for your business?
I’m going to redo my website to better highlight my conversational English and business English tutoring. I plan to rehire a contractor—despite a tight budget—so I can focus on higher-level priorities and grow more efficiently.
Copyright © 2021 - 2026 GeekPack, Inc| All Rights Reserved | Design by Soul Alchemy Branding
| Built by GeekPack®
Privacy Policy | Terms & Conditions | Refund Policy | Sitemap
