My Very First Tutoring Job Was In My Worst Subject Area... A Subject I Had *Gasp* Failed!

My first paid tutoring session was in my most dreaded subject...math.

And I was scared to death.

See, I had failed math my entire life AND was about to get paid to teach a high school student my worst possible subject.

I wasn't a math teacher.

I was barely a certified English teacher.

I hadn't gone to school to be a teacher and certainly didn't have any educational degrees that really qualified me to teach.

Terror Turns To Inspiration

What happened during that first tutoring session was both terrifying and inspiring!

I had knots in my stomach. I had to wipe my sweaty palms on my skirt before shaking her mother’s hand… then greeting my new student.

They were nice. Sweet even. Offering me iced tea.

And I’m sure I looked like a deer caught in headlights. I definitely do not have a poker face.

So, we dove right yep, my most dreaded subject...math. Algebra.

Now, let me remind you, I was not, nor have I ever been, a math teacher.

And yet when this mother called she begged me to “give it a shot” when I told her I simply wasn’t qualified.

So, I found myself seated at their kitchen table, the mom off putting away laundry while I sat - heart hammering double time in my chest - with the sweet-faced, very smart, high school junior who confidently told me, while making awesome eye contact, her plan to attend an Ivy league college.

In that moment, I knew I was lost. She was smart.

All my old fears flooded me, as at 28, I sat there horrified by the fact that I was about to be shown up by this brilliant, young girl, who thought I could help her in, of all things, Algebra.

I wanted to crawl under the wood table, but instead I crossed my legs, pretended my spine was a steel pole holding me upright and made the decision to - no matter what - not charge for what was sure to be a horrid one-hour session of uselessness.

I mean, really, who was I kidding anyway.

I so wasn’t qualified to be here. But here I we got to it.

That decision, to not charge and just wing it, allowed me to relax enough to smile and ask to see her current work, notes and assignment.

What Happened Next Shocked The You-Know-What Out Of Me!

Her name was Maya. My very first tutoring client.

The one who wanted math Algebra...and terrified me with her smart dreams of Ivy League colleges and well-spoken-ness.

The one who was organized and neat. She handed me a notebook I was able to understand almost immediately.

I knew suddenly that she had skills.

I could see her diligence to try and her desire to get it was present in her work. I also saw the gap. She was just missing a little something, a bridge, to get her from one point in the assignment to the next.

Her current work, while foreign to her, wasn’t nearly as terrifying for me upon closer inspection.

Let me repeat that!

When I looked closely at her current notes (and not the entire subject of Algebra!), what was foreign and impossible to her in that moment, wasn't so horrifying for me.

I saw it for what it was.

One concept, of many, in a subject known as Algebra.

Having decided that I wasn’t going to accept the agreed upon $35 session fee (as I knew this would be a bust), I was able to point out things that I felt were silly, stupid and obvious.

I stopped feeling overwhelmed, as though I had to have all the answers, and started to enjoy this smart, young girl beside me.

What I quickly learned, as I watched Maya smile and nod, bending her head as she quietly worked to solve a difficult problem based on my recommendations, is that tutoring was not about knowing everything!

In fact, tutoring was about so much more than the subject matter.

My terror and sweaty palms gave way to relief, and then inspiration, as Maya got one problem after another right.

She was thrilled.

I was shocked.

Her mom was serenely pleased from a distance.

All too soon, the hour was over and Maya was closing her books - assignment done and understood.

She politely asked for another appointment after expressing how much I’d helped her.

Helped her!?!

When I hesitated, she firmly requested a session for later that same week.

Her mother, with equal firmness, insisted I accept the $35 check she pressed into my hand. Then sweetly demanded a few business cards to pass along to her parent friends.

Business cards?!

I told her I'd bring some with me next time while making a mental note to order them right away.

All too soon I was standing outside their front door, in the bright Florida sunshine, on the verge of doing a little, happy dance.

I was officially in business.

What had started as a flop and filled me with an intense fear that I might fail (again!), had turned out to be the most inspiring hour I’d had in...forever.

An hour I tried to turn down numerous times because of fear.

From Tutoring Once To Tutoring A Lot

Suddenly, through tutoring, I was making great money. And nope, that’s reality, not the nightmare.

In no time, I was bringing in an additional $2,200 per month of income just from my side-gig tutoring.

That figure, $2,200, was my monthly salary teaching high school full-time (as in 60+ hours a week!).

By tutoring part-time I had doubled my income.


But back to that nightmare.

My Greatest Fear Became My Amazing Dream

I’d wake up in the morning, two to three times a week, with sweat beading on my forehead and my breath suspended in my lungs, knowing that this was the day.

The day they’d stop calling.

The day parents would realize I was a fraud, a fake, a wanna-be tutor and not a good one!

This was the day parents would smarten up, stop paying me to tutor their child, no longer refer me to their friends and realize I wasn’t worthy.

Hmm, self-esteem issues, anyone? (More on that another day!)

This plagued me often. Considering I was only tutoring four afternoons a week and every other Sunday afternoon, having this dream twice a week was terrifying.

This doubt, this dread that it would soon be over and I’d be found out, allowed me to treat my new tutoring business more like a hobby than a business.

I acted like I didn’t care.

If parents stopped calling and kids stopped coming, no sweat, right?! It was just this little thing I did on the side.

But little it was not!

I was starting to pay off my debts — student loans, car payment and have money in the bank.


For the first time in a while, I was in the black.

Even in my math-was-an-issue life, I knew that was a good thing.

I loved my Center 4 Learning tutoring business.

I loved my students.

I loved tutoring — even in math.

And deep down, I didn’t want it to end.

But for more than two years, I acted like it was just something I did.

I “poo-poo-ed” it and didn’t respect it. I was so afraid that my lack would be found out.

I mean I wasn’t certified in half of what I tutored in...

I Wasn’t All In

I had one big toe in. Just one big toe of one foot. Not even an entire foot.

My escape plan was pretending not to care while staying planted, stuck in my day job teaching high school and making excuses as to why tutoring wasn't really a serious thing.

I was ready to bail if it didn’t work. I was totally prepared to blame myself, and others, if parents one day stopped calling.

Have you ever not believed in yourself?

Thought you weren’t worthy?


A fraud?

Friend, I get it. That was me.

And it wasn’t until I discovered what it meant to be all in, that my very successful, little, side-hobby-of-a-business tutoring took off and grew into something utterly amazing that has helped over 3,751 live students in just over a decade (and 100x that virtually!).

How would it feel to be able to personally say that you helped teach, influence, support and groom-up over 3,700 students?

Well, let me tell you, friend, it’s fab-u-lous!

If you want to learn how to be all in and make a real go of starting and growing your own tutoring business – for real – join me right now by plugging into a free audio series I created entitled

How To Start a Profitable & Successful Tutoring Business

I share what I did wrong and what I did right, plus actionable steps you can do right now to enroll your first student in less than 24-hours...or your tenth if you're already in business!

If you too have a dream of helping groom up the next generation, make some extra money making a difference or share the knowledge you've accumulated with others, then this information is truly priceless.

Go have a listen, as these three audios alone can shave at least two years off your learning curve while allowing you to make a difference, one mind at a time.

Education Lady | Jill Stevens

Educator. Writer. Life Long Learner. Jill has a passion to help the next generation and improve learning across the board. She’s here to change the world, one mind at a time. Right now she does that through words with purpose and by training up remarkable, rockstar tutors.