A Life Lesson That Shaped My Tutoring

I was never going to be a lifer.

When I made the decision to leave my job in my fourth year of teaching, in the public school system, I was pulled aside by many.

I heard things like:

“Are you sure?”
“What will you do?”
“Why would you leave? This is the year you get tenure!”

“I thought you were a

I had to ask the last teacher, one I liked very much as he was always smiling, what he meant by the term lifer.

A lifer is a teacher who stays in the system till retirement in 30-35 years.


I guess a career like that, with benefits and paid holidays and tenure, felt more like a life-sentence to me than something I’d enjoy.

And when something is a life-sentence, how can you really keep doing it?

I couldn’t.

Most people don’t seem to have that luxury, or so they think. To leave something that no longer lights them up, as I did four and a half years into my teaching career.


I’ve been thinking about that for some time now, as I help others start their own tutoring businesses.

Why do we accept feeling trapped? Because we have bills and families and mortgages?

So, why didn’t I let those fears stop me, too?

Without realizing it, I’d been building up an escape plan.

I’d been tutoring four days after school and oftentimes holding an ACT or SAT Test Prep class on Sunday afternoons.

For three years I did this.

Without realizing it, I had a thriving side-business, that I treated as a hobby, (which I’ll talk about more another time), yet it was earning me more money than my extremely long hours teaching in the classroom.

And even better, it lit me up.

It excited me.

It made me happy to help kids outside the school environment, which I found flawed, lacking and painful to navigate at times. For teachers, administrators and students.

Looking back, I realize I could have left sooner.

Looking back, I see that circumstances in the form of a death of someone important to me were the catalyst that pushed me over the not-gonna-be-a-lifer line.

Looking back, I know that doing what I loved - tutoring - made me a better person.

Looking back, I understand that we have only one shot, one opportunity, one moment in the span of this lifetime and I’m glad I took the dive into the unknown.

Was it scary?

Yes and no.

For me, it was just as scary to think about staying in a place I wasn’t meant to be - a classroom for life.

So, why do I share this life lesson of mine with you?

Simple. I’ve spoken with so many teachers and professionals in other walks of life who are not happy and yet afraid to make a move.

And here’s what I know. Nothing is guaranteed.

Not the life of my fiancé who I lost in a helicopter crash, which was the catalyst I mentioned that pushed me to decide: stay in the classroom and be semi-happy doing the time? Or spread my literal wings and fly… or free fall?

I chose to fly.
And I soared.

Was there turbulence?

But isn’t there always?

My classroom days were full of it, too.

The only difference was a guaranteed paycheck for $1100 every two weeks direct deposited.

And that I could make in a few days of tutoring…

So, if you’re putting off your happy for the illusion of security, know from someone who’s been there, that one step today can set you up to soar.

What’s one step you could take?

And remember, one of my fav quotes of all time is Martin Luther King, Jr. “You don’t have to see the whole staircase, just take the first step.”

If you want to start tutoring, like I did, here’s a few easy first steps.

If you want to work on how you think and shift your perspective to happy, check out 52 Life Lessons.

Both might just rock your world.

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.