“I want to be a teacher.”

“Good news,” I told my boss. “I got into grad school… I’m going to need you to change my schedule.” That’s how I broke the news to my best boss ever,  that I was going to teach.

I was 7 or 8 years into an insurance career. The company paid for most people’s grad degree. Not mine. “That’s for your own personal use, not for the company.” People got their JDs, MBAs. LMNOPs… all on the company dime, then most left to do their own thing.

“Not true. I may want to be a corporate trainer.” I got vetoed.  This–(I hadn’t yet learned) was yet another classic case of “Undervalued Teacher Syndrome.”

My boss couldn’t change the company policy, but he did something even more valuable. He understood.  He saw me as an individual and did everything in his power to help me get to the place I needed to be. This, by the way, was my first lesson in what it means to be an excellent teacher.

Thinking about switching to teaching…?

What–in your present career–do you love that you can bring to the table? What’s lacking in that career that you expect to find in a classroom?

When I went into teaching, I wanted to take the best things about me in insurance–the ability to feel compassionate, the ability to help, and the ability to understand people, especially in difficult situations. And, I was a nerd, so I could teach, guide, and help kids the same way I helped adults.

In insurance, I educated people about complex procedures–settling injury claims, fixing cars, undoing big accident problems, and often, complicated contract and legal language. I knew contracts, a great deal about medical, multitasking. But for me, what I liked about insurance was this–helping people, sometimes at the worst times in their lives. I helped them get back on their feet and to a better place.

What are your strengths and why do you want to teach?

“I have to leave and teach.” A beam of light hit me from the sky. I wrote about this in Don’t Sniff the Glue: A Teacher’s Misadventures in Education Reform. I heard a voice that said, “You need to leave this job and teach.”

When you start hearing voices, you’d better do one of two things… take a vacation, or listen.

I listened. I applied to grad school, and I got in.

Things you need to know before you jump into teaching

This is the important part. The “full disclosure” part. Do not quit your job before you understand each of these things and check off the “I have read these notices and fully understand.” You know how you skip reading and check off the box on every single app you download? Don’t do that here.

One: Teaching is the best job–if you love kids.

I mean truly love them. You may think you like kids, but you won’t know if you really do until one or two of them vomits on your new outfit, tells you off, makes you break up a fight, or asks you “Can I go to the bathroom?” in the middle of your evaluation lesson.

If you can look at every single kid and see into his or her soul, and you want to have a conversation with each child… you think about them from time to time over summers and weekends… you can grab a book and say, “Hey, I was thinking of you–you’ll love this because…” you are in the right place.

Two: Teaching is a 24/7 job–unless you learn to set limits.

There is always something to do. You’ll get ideas in the shower, you’ll have data, paperwork, grades to enter, lessons to plan… I don’t know a teacher who hasn’t had a 24/7 period. But, unless you regulate that quickly, you will suffer. You may become ill, your family will most certainly lose patience with you, and… it’s not good for you.  It’s important to find balance if you don’t want to become a burnout statistic.

“This isn’t what I signed on for.” The science teacher down the hall left in a year and went back to industry. If you’re going to go through all the trouble to change careers, you need to come to the table with a sense of balance. As a second-career person, you may have an advantage here. You’ve already been through a new career at least once.

Three: It’s easy to go broke teaching.

Four: Teacher benefit structures are usually different than corporate benefit structures

I walked in the door and asked, “What’s the match?” referring to the amount of money I had to contribute that would be matched for my 401(k). That’s not how schools work. In the beginning, we had full medical and a pension. I didn’t really understand what a pension was after coming from corporate. A pension is an old style system where you keep one job for a really long time and get a regular income when you retire. My grandparents had pensions.

More and more schools are doing away with the (expensive) pension system. Mine took it away midway through my career. I was one of the last people to get a hybrid mashup of 10 years worth of pension credit left in there and then the rest was 403(b) (the teacher version of a 401(k).  If you’re in the pension system, eventually you’ll have to contend with “years in” the system, then you’ll know what your retirement income will be.

Early in my career I didn’t pay attention to this. People today have multiple careers. I was one. Pensions work well for people with one really long career. They can serve as a set of golden handcuffs keeping you at jobs or in districts that aren’t good for you if you don’t understand how to plan around them. And, some systems have gotten rid of them altogether meaning you need to save and invest on your own.

Five: Not all school systems and teaching jobs are created equal.

This is critical. When I started teaching (you can read more in A Broke Teacher’s Guide to Success: How to Build Your Dreams on Teacher Pay) I was told this, “Take the first offer you get. You’ll be lucky to get it.” That’s a bad way to conduct a job search in any field. If you are a career changer, I doubt you did that in your first career unless you were right out of college, entry level, and it was a “get in the door” Hail Mary pass.

Not all schools are created equal. 

  • Public, Private, Charter, Alternative:  There are many types of schools. One may suit you better. Take some time to visit schools on the extremes.
  • Income level: This is hotly debated in education today. I’d encourage you to look at schools in high-needs areas as well as elite schools. One thing that may surprise you… it’s not always the “poor” schools that do without. Sure, I’ve been in broken down schools, but often times, lowest-income area schools are fixed first. Highest income area schools have funds and endowments. But mid-income area schools (or working poor areas) struggle. They’re too high on the money chain to get emergency or infrastructure funds, and not wealthy enough for someone’s grandfather’s trust to fix things.
  • Diversity level: There’s no right or wrong answer to this. I happen to love and need diversity. I have friends (of all backgrounds) who aren’t naturally comfortable in diverse situations. If you don’t love the culture(s) of the school where you get a job, you won’t succeed. If you’re teaching, you’re most likely willing to learn about cultures, religions, home lives that aren’t like your own. Stepping outside your comfort zone positively is good for you. But… if you’ve got lines in the sand and you’re not comfortable with certain situations and can’t get comfortable fast, don’t teach at that school. You’ll be doing students a disservice.
  • Mission: What’s the mission of the school? Is there a specific formal mission statement? This is especially noticeable with magnet schools and charters. But, there may be an underlying mission or “all hands on deck” approach. There may also be a “wall-only statement.” Those are mission statements put there to check a regulation box that no one knows or follows. Find out what the mission is, see if it’s lived out, and if so, and you’re excited about it, it’s a good school for you.
  • Grade level: I thought I wanted to teach middle school and took a job at a high school. That turned out to be the right place for me, even though I still love younger kids. I started in elementary education because people told me I’d never get a job in high school history. They were wrong. And I would have done well in elementary but it wouldn’t have been my perfect place. I like the “near-adult” interactions of high school kids, and their independence. I like the curriculum, the events, watching the turn to adults, and the fact we stay connected after graduation. Take some time to look at the day-to-day classroom for various subject areas and age groups. Pick the right one for you.

Be honest with yourself about who you are and what you want in a class. I wanted to teach in an urban setting. Diversity, culture, and languages were important to me–they were a big part about what I loved in my first career.

If you want to end up in the right school for you, spend some time thinking about your perfect classroom. Are you Robin Williams in Dead Poet’s Society? or the principal in Lean on Me?

On that note… teacher movies are the great lie. If you rooted for math teacher Jaime Escalante in Stand and Deliver, know this… that wasn’t all heroics. He got frowns from teachers in his district for going above and beyond. Politics are real, movies aren’t. You have to know the type of district you’re joining.

There are two ways to do that–research and running around. You can sub, visit, volunteer, drive by, spy, ask anyone you know, but learn about the climate, the gatekeepers, the organization, the flow… everything from how you’ll get assigned cafeteria duty (I happen to love cafeteria duty) to who gets what schedules, and why.

Also, what’s the leadership like? What are evaluations like? What are the rules and mandates? These things are important for any teacher, but especially you, as a second-career teacher. You’re switching into teaching for a reason. Think about the types of things you loved from your first career and the types of things you were lacking in the perfect organization. Schools are no different–to be happy, you need to find a culture match.

Six: It’s easy to go broke teaching

You probably took a pay cut to teach if you’re coming from a different profession. Whether you were a research scientist or in Corporate America, pay grades are just higher for equivalent-level professionals.  So, you’ll start by taking on some student loans to get your teaching credentials. Or, if you’re in a good alternative-certification program you may be able to avoid this.

But when you get your first classroom, you’ll want to set it up right. In my corporate job, I walked over to the cabinet and took the supplies I needed. In teaching, that’s gold-level rare. We got $20 to spend on whatever we wanted–and it had to come from a thousand-page catalog that was such a pain to order from (think: paper order forms in triplicate, product numbers, tallying prices to get to that $20…) that I refused to accept my $20. It wouldn’t buy me anything I really wanted at catalog prices–it’s better to go out to Walmart at back to school sale time.

Therein lies the problem. If you’ve been in any other career, chances are you come with a set of corporate, exec, or service-level experiences. You get things done. You don’t waste time. This means you’ll know the five-cent sales are great in July. Nickel by nickel, you’ll spend away your paycheck on your job.

The entire point of this website and the book–to stop myself and others from doing just that.  As a second-career person (who probably took a pay cut to teach), you must protect your personal finances and let your job pay for your job, even if it means saying “no” to a good idea or supply.

Seven: Teaching can be isolating… or suffocating.

Schools can be isolation chambers unless the culture is specifically set up to collaborate. When I first started teaching, I was given a classroom and a book and no one ever bothered me again–until the age of data, testing, and high-stakes evaluation. Even then, though, department meetings were about putting curricula in grids, not about discussing students and collaborating on ideas.

Some schools build this type of collaboration into the schedule. If not, you have to be intentional about getting out of your class. Find teachers whose work you like and ask to visit them. I’d bring coffee and tea to people, “Haven’t seen you in a while, brought you a cup of coffee.” I’d hang out and observe and create my own partnerships with people I thought taught well.

Forced collaboration, though, is just as bad as isolation. If you’re a person who needs more autonomy and space, you want to look for a school culture that’ll let you have the space you need.

Eight: Lots of things are broken

The copier. The heat. The requisition system. Expect broken things and red tape. To this day I keep a kleenex in my pocket because getting caught in a bathroom without toilet paper makes for a very bad day. There were years without heat, and I secretly learned to fix copiers, a skill I only told my very best friends in the world because people who knew I had some tech skills would pull me out of class to fix their computer stuff.

Some schools have a lot of broken things. You’ll want to make friends with everyone who handles a requisition, repair order, or supply chain first. Walk stright by that superintendent in order to shake your custodian’s hand. Trust me on this.

Nine: In the end, the kids and their families are your customers

Schools have a lot of regs these days–curricula, evaluations, data, testing. As a multiple-career person (I started in insurance, owned businesses, shut businesses, worked in tech, saw tons of cutting-edge businesses fail and succeed)… I learned one thing. The only thing that matters is my customers.

In my business, they paid the bills, kept the lights on… or didn’t.

In tech, I watched companies change direction and delight customers and become big names you use. And some stayed fast to doing what they wanted to do and ended up shutting down.

Schools are a lot like that–we have mandates, regs, and standardize. The difference is this–kids legally have to attend. Ask yourself, “If they didn’t–if they were retail customers and could decide to be in this school/class, would they be?” That one question changed everything about how I operated, from how I held a conference to the types of lessons and papers I designed.  When you step into your classroom, it can feel overwhelming. If you are serving your customers (your kids) it’ll all work out in the end.

That’s a lot to think about

There’s a big teacher shortage. There’s a really big “good teacher” shortage. You can do this! But, education is currently in a state of flux. The system is probably very different from your prior career. The same is true for teachers transitioning into other fields. Come to the table with a consciousness and flexabiity and you’ll be less shocked by the water temperature when they throw you in the pool.

As a second-year teacher, you’re a gift. Realize that. Pick the right school, set some boundaries, and take care of yourself first. You’ll have a wonderful career ahead of you.


  • How to switch in the other direction, from teaching to other careers.
  • How to redo your social profiles to set yourself up for a job search.
  • How to grassroots market yourself for success in your teacher job search (all things resume, social media, and “connected educator.”)
  • AND… because I have had requests, I’ll be hanging out my shingle to do these things with or for you. Reach out to me to discuss how I can help: dawn@broketeacher.com


Photo credit: Jose Aljovin, Unsplash.