The Challenge We're Solving Today

Most transitioning educators start their job search by asking:

“What jobs can teachers get?”

This shouldn't be the first question.

This is what you want to ask first:

“Why do I want to leave teaching?”

(and no, this isn't going to turn into some mushy, emotional exercise.)

Here’s My Personal 5 Why Activity

👋Hi, I'm Steph in 2015. I want to leave teaching.

1️⃣Why do I want to leave teaching?
Because I want more respect AND upward mobility in terms of promotions and money.

2️⃣Why is that important?
Because I have a vision of the kind of life I want that includes bigger projects, more responsibility, and significant leadership opportunities.

3️⃣Why is that important?
Because I’ve been doing innovative things and feel like I’m not really appreciated the way I want in this role. The cool things I’ve come up with could be HUGE for education.

4️⃣Why is that important?
Because I don’t want my ability to contribute to systemic solutions, like making other teachers better at their jobs and making teaching easier and more fun, to be capped by the limitations of one school.

5️⃣Why is that important?
Because I’m smarter, more professional, and hungrier for more than what this will give me. I’ve developed expertise in a trial by fire way with technology transformations in classrooms, and I’m ready to apply that to companies needing fresh ideas.

😎Is it any small wonder, then, that I moved into a startup edtech company that focused on computer science + coding education for K-8?? Thank you 5 Why Activity!

Why This Matters to You

When you know the real reason behind your career change, you can make better choices.

And don't be sarcastic and say "I already know the real reason. I want more money!" or something equally flippant.

Trust me on this one. Go through this activity. 

What you find WILL surprise you. Not "may." WILL. Surprise. You.

Maybe you don't just want higher pay. Maybe you want enough money to travel, save, or move.

Maybe you don't just want a role outside of education. Maybe you want work that lets you write more. Maybe you want work that lets you write less.

Maybe you don't just want less stress. Maybe you want to stop being face to face with people all day.

Maybe you don't just want a new setting. Maybe you want an office building, your own cubicle, with easy checklist style tasks. Maybe you want more responsibility. Maybe you want less responsibility.

Your fifth "why" is your REAL answer.

That deeper answer will help you decide which roles to research, which jobs to skip, which skills to double down on, and what kind of work is worth your energy.

What I’ve Seen When People Try This

I’ve run this exercise with several people, and it is always interesting to see where the fifth “why” takes them.

They always start with:

"Why do I want to leave teaching?"

At first, the answer is almost always about stress, pay, workload, garbage leadership, lack of flexibility, yada yada.

But by the fifth “why,” the answer gets WAY more specific.

Here are a few of my people's fifth answers:

“I write constantly as a teacher, but I want writing to become the center of my work.”

“I’m the person people come to when a new tool is confusing. I love it when I'm the person with the answers.”

“I don’t want to spend my whole day managing behavior. I want to be in a quiet office, doing office management work. I barely have to talk to anyone and I still can do a great job.”

“I want to work in an office building because I miss having a professional environment that feels separate from the emotional intensity of school.”

"I’ve seen what makes classroom technology work and what makes teachers ignore it. I want to give these insights to a new company trying to sell to schools."

That is why this activity is useful.

It helps you see what is really driving your career change.

A Better Approach for You

Start with one question from the menu below.

Then ask “why?” five times.

Do not try to make your answers sound impressive. Tell the truth.

Choose one:

1. Why do I want to leave teaching?
2. Why do I feel ready for a career change now?

Answer it in one sentence.

Then ask, “Why is that important?”

Answer again.

Repeat until you have five answers total.

By the fifth answer, you will be much closer to the real reason this career change matters

AND

you'll have a more targeted way to talk about yourself

AND

a more targeted way to filter for specific roles.

Summary

• Your first answer is never the full answer.
• Asking “why” five times helps you get past surface-level career change thoughts.
• Your deeper reason helps you make better choices.
• This activity is especially useful before researching roles or rewriting your resume.
• The more honest your answers are, the more useful the exercise becomes.

Your Next Steps

Choose one question from the menu and write your five answers.

Then look at your final answer and ask yourself:

“Does my current job search match what I just said I really want?”

If yes. Hooray. You're more self-aware than most people.

If no. That's totally cool too. Now you have a new lever to pull to make a successful career change.

P.s.

My Career Change Accelerator can make this process so much easier for you. I pride myself on this. 

I truly hope you'll give this a try. It's one of my favorite activities. 

See you next week.