Jennifer Henson

Covering less content but mastering that is better than rushing through just to cross something off your checklist.


Jennifer Henson ( a.k.a “The GOAL DIGGER”) is a nationally sought after test prep expert specializing in the ACT test. Jennifer, who was Winton Woods City School’s (OH) Teacher of the Year in 2014, holds a Master of Education degree with a Bachelor’s in English from Xavier University—where she was a walk-on tennis player. She’s taught 21 years and coached ACT prep for over 7 years– and has an army of teachers trained to assist her requests for tutorials. Her former ACT students now attend notable higher learning institutions, including Notre Dame, The Ohio State University, Texas A&M, The Naval Academy, and the University of Kentucky—among others.

Jennifer has assisted students from California to Connecticut—and states in between—to reach their personal ACT goals. No score is too low or too high, as she has doubled the scores of students starting at the low end, in addition to helping initially higher scoring students achieve the coveted 36 on every section of the test. Two young men playing D1 football had a composite score of a 9 originally, and scored 18 and 20 (respectively) after working with her. Two of her former clients now have NFL experience.

Over the past several years, Jennifer has devised a proven program that identifies student strengths and areas of needed improvement, and tailors instruction to address individual student needs. The program is comprised of teacher-led instruction and self-managed studying and incorporates elements of evidence-based learning strategies.

The teachers need between 12 and 15 lessons with students, depending on their need (original score). Students will have approximately 2 hours of homework after one-on-one session. The lessons start approximately 3 months in advance of the test they wish to take.

Where did the idea for Goal Digger come from?

My students come to me with a variety of target scores but all have one thing in common: a goal. My name gets passed around among mom groups as “The ACT Lady” or “The ACT Whisperer” but I really wanted something a bit catchier as my official name. I also like how people first read it as ‘Gold Digger.’

What does your typical day look like and how do you make it productive?

My typical day consists of meeting with students from all over the US via online meeting tools.(I also have a handful of local students who I meet in person). We discuss content and strategies to help them reach their maximum scores. My time with students is my main priority of my work day, so I begin as early as 6 am some days to meet student schedules. I also answer emails, social media messages, and correspond with parents daily.

How do you bring ideas to life?

If I have an idea I try to implement that idea on a small scale before I go big. I want to work out the kinks with a few people before I try it on a large scale. I don’t mind to fail…but failing on a small scale is better.

What’s one trend that excites you?

The trend that excites me is online collaboration. Due to social media, I have met so many others in my field with whom I can share best practices. In fact, five of us just gathered in Houston for a “conference” of sorts. It was empowering!

What is one habit of yours that makes you more productive as an entrepreneur?

I keep to-do lists going constantly and always have paper available for ideas or things to follow up on. So much runs through my head that I have to keep organized. I still use paper and pen for this!

What advice would you give your younger self?

So many people would tell their younger selves to act on this entrepreneurial path sooner. I would not. I truly believe that 22 years in the high school English classroom, a Master’s degree, and being named Teacher of the Year in my district are all part of my path. I would not rush it; I would not change a thing.

Tell us something that’s true that almost nobody agrees with you on.

Covering less content but mastering that is better than rushing through just to cross something off your checklist. I was observed by a principal once who said, “I love the pace of your class. I can see you have a goal in mind but you weren’t in a rush to get there.” This applies to so many parts of life.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I communicate with my customers frequently—both parents and students. My business is unusual in that parents are the customer yet the student is who I am training—so I have two customers.

What is one strategy that has helped you grow your business?

I have a large following on social media, specifically Facebook. I have thought about marketing more to teenagers via IG or Twitter, but it is really their parents who are making decisions. I share awesome student results and tag the customer on that post. This often draws in interest from their friends.

What is one failure you had as an entrepreneur, and how did you overcome it?

I have spent money on advertising on Facebook that was ineffective. So, I found a business owner that was seeing a great return on FB marketing and learning all I could from her. I have surrounded myself with others whose target market is the same as mine…but our products do not compete with each other.

What is one business idea that you’re willing to give away to our readers?

I would start a business linking college students living away from home with locals who can provide laundry and homemade meal services to them. My mother-in-law would be my first employee!

What is the best $100 you recently spent? What and why?

I am paying for a virtual assistant to do some of my marketing. I am amazed at the time it is freeing up for me.

What is one piece of software or a web service that helps you be productive? How do you use it?

I love the app Zoom. It is a tool that allows me to meet with many students at once. I sometimes have 30+ students on my group reviews the week of the test.

What is the one book that you recommend our community should read and why?

The book that has empowered me in life and business is John Gordon’s The Carpenter. It has changed how I think about everyone I meet.

What is your favorite quote?

She said she could, so she did.”

Key learnings:

• Grow at a pace that suits you—not following every else’s pace or path.
• To do lists keep you focused and on task.
• Embrace new technology. It might just be what takes your business to the next level.
• Surround yourself with greatness and people who have similar target markets as you. The things we can learn from each other are invaluable.

Jen Henson ACT Prep on Facebook : Jen Henson ACT-Prep
Jen Henson ACT Test Prep on Facebook : Jen Henson ACT Test Prep
The GOAL DIGGER on Instagram: goaldigger_act_prep
Jennifer Henson on Twitter: @JenniferHenso17