Is the grass really greener?

How to know when to leave teaching (without regrets)

If you're a teacher considering a career change, you've probably asked yourself this question:

"What if I'm just romanticizing something different? What if the grass isn't actually greener on the other side?"

You're not alone. This question comes up again and again for educators trying to decide whether they should quit teaching.

The "grass is greener" syndrome is a pattern of thinking where you consistently believe that better options exist elsewhere rather than in your current circumstances. It makes it hard to feel content with your life as it is.

Are you too wondering if you're just imagining that another job will be better than teaching? Worrying it won't be and you'll regret leaving?

Let me share a story about my own grass-is-greener moment, and what it taught me about making big life decisions.

My grass is greener story

Back in 2015, my husband Mark and I were thinking about moving from Northampton, MA to Pittsburgh, PA (doesn't everyone dream of the steel grey skies of western Pennsylvania)?

We had lived in Massachusetts for 5 years, and we liked it, but we were also craving something more: a place we could really call home.

Pittsburgh would bring us closer to our families, who lived in Indiana and Virginia, and into a community where we had a lot of friends.

In this phase of considering a big move, I was up to my eyeballs in "grass is greener" thinking.

Without solid info about what Pittsburgh would actually be like, I used my imagination to fill in the blanks with best-case scenarios: Weekend trips to see family, cozy hangs with old friends, big(ger) city living, and the excitement of new career possibilities. I was painting quite the rosy picture!

And then...I got a few interviews for jobs in Pittsburgh.

I traveled there, had the interviews, saw my friends, and decided with almost total certainty that I didn't want to move there.

I had to get right up to the edge of moving there to know that it wasn't right for us. I had to climb over the wall and see if the grass actually was greener on the other side. It wasn't!

Almost overnight, our plans changed.

We decided to stay in Northampton, and within four months, we bought a house! We've lived here very happily ever since.

What does this have to do with leaving teaching?

You won't know if another job is better for you than teaching until you either try something else or get as close up to the edge of trying something else as possible.

You've got to actually see a little bit of the other side, not just fantasize about what it might look like.

You've got to gather real information. Otherwise, you'll end up filling in all the blanks of what it could be like with best-case scenarios: a job with zero stress, perfect colleagues, amazing pay, endless flexibility.

How do you know if it's actually better out there?

What kind of real data can you get to help you gain clarity about what awaits you on the other side?

I've ordered these from lowest to highest commitment—and from least to most clarity gained.

Research actual roles and organizations

Instead of using your assumptions to decide what a certain job or role would look like, search for accurate information online. Take a deep dive into specific positions at specific companies. Research salary ranges for certain types of roles. Read blog posts or listen to podcasts by professionals in the fields you're curious about.

Talk to people in the career fields that interest you

Don't just read job descriptions or summaries of careers—talk to actual humans doing the work. Ask them about the day-to-day realities and what they actually do. This is one of the most valuable steps you can take to see past the fantasy you've created in your mind.

Get up close and personal with your possibilities

Just like I needed to actually visit Pittsburgh and interview for jobs to know it wasn't right for me, you need to get close enough to other opportunities to see them clearly. Job shadow someone for a day, volunteer, freelance, or take on a side project in a field you're curious about. Even small experiments give you crucial information.

Actually take a job

Ultimately, the only way to know for certain if something is right for you is to do it. This is definitely the biggest leap, but armed with information from the previous steps, it's a strategic move rather than a shot in the dark with your fingers crossed.

Doing this research means you're not leaving teaching on hope alone. You've looked closely at the other side and can say with confidence whether it's actually a better fit for you.

The truth about teacher career change

Here's what I've learned working with educators navigating career transitions:

The grass MIGHT be greener on the other side. It wasn't for me in Pittsburgh. But it could be for you in your career change away from teaching.

The only way you'll know is if you have a look-see.

Some former teacher success stories are about leaving the classroom and never looking back. Others are about teachers who explored options, realized teaching was actually the right fit, and reengaged with renewed commitment and boundaries.

Both outcomes are valid. Both require the same process: gathering real information, testing assumptions, and making decisions based on data rather than fantasy.

So if you're wondering whether the grass is greener, stop wondering and start looking! You need to gather enough real information to make a choice you can feel good about—whether that's staying in teaching with fresh perspective or confidently stepping into something new.

I'm Laura, a Career Clarity Coach for Teachers feeling stuck.

I help you explore career possibilities beyond the classroom so that you can make a confident choice about what's right for you, based on your strengths, values, personality, and what you want most for your life.

Join other teachers in the Teachers at a Crossroads course