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When you’re changing jobs, it can be really exciting. It can also be incredibly difficult to leave your old job behind.

I’ve you’ve ever switched jobs, maybe you can relate to how I’m feeling. At least if you really liked the job you left.

When I graduated from college, upbeat and energetic with my teaching license, I landed a job at a school I loved! I knew I loved it because I did my student teaching there. The staff was wonderful, the students were fun and hilarious, and I truly believed in the school mission statement.

I started my career as a paraprofessional, and as our school grew over the years, I moved into the role of an 8th grade Social Studies Teacher with my own classroom and everything. I felt like I finally arrived! The best part of it all is I got to work side by side with my lovely wife, a 7th grade Science Teacher.

Now, six years later, I’m leaving it all behind to start a new adventure in a brand new school. I don’t have a great idea of the student culture, the school mission statement, or what kinds of challenges I’ll be facing. Anytime you’re changing jobs, you’re walking into an element of unknown territory.

I’ve been in emotional turmoil most of the summer thinking about the prospect of leaving a school I love and heading into the unknown. At times I’ve felt excited and invigorated about the change, because I believe it will be a good move in the end. Other times I’ve been a mess of tears, mourning all that I’m leaving behind.

Today I want to share the benefits and heartbreak that helped me make this decision, how it will affect my family, and how I’m balancing my mixed emotions.

Why I’m Leaving a School and Job I Love

Two or three years ago, I would’ve never considered leaving my job. I had just been promoted to teaching full time with my own classroom and a brand new subject. Also, our school district was looking to expand and build a high school. It was an exciting time of growth and incredible opportunities. How could I ever leave?

Well, a couple things happened since then that completely changed my career outlook, and affected my family.

First, the very solid plans for building a new high school fell through. I was SO excited to be part of planning and starting a brand new school, building curriculum and creating a positive school culture. There were also going to be varsity sports programs that I was pumped to help build. I love sports and coaching, and aspired to be the head basketball coach.

When the high school was off the table, it was a huge blow to my career path and possibilities at my school. I felt like it took the wind out of my sails. I still loved my school, but it was hard to watch my dreams and excitement die.

Second, I worked at a public Charter School, which is strange that it’s a reason I’m leaving because I love working for a Charter School. Our school charter has allowed us to do amazing things for our students and programs, and I believe heart and soul that our school is constantly changing student lives.

Are You Having Mixed Emotions About Changing Jobs

The downside of being a Charter School is we don’t get paid on the same scale as the other public schools in the city. And sadly we aren’t always guaranteed a yearly salary increase to keep up with inflation. As a family of teachers, we don’t make much money in the first place, and even less with a Charter School.

The big reason this caused me, and my wife, to look elsewhere is our beautiful baby daughter. Now that we have a ton of other expenses, hello daycare, we wanted to increase our income to keep moving toward our goals. Working at a traditional public school would be a major salary increase.

Related to the lower salary, the benefits package isn’t super great, which wasn’t a major problem until this year. Starting this new school year, our benefits package changed dramatically. Brace yourself.

Our deductible and out of pocket expenses DOUBLED! We went from paying $1,500/3,000 for deductible and out of pocket, and now we’re paying $3,000/6,000. With a brand new baby who could get sick at any time, this was pretty shocking. Especially since we’d love to have another little Griffin someday. That just got outrageously more expensive for us and insurance won’t cover nearly as much as with Baby #1.

For us, this was the last straw. We were thinking about looking for new jobs, but this pushed us to actually apply. If my wife or I could get a job with another district, they would probably have a better benefits package and we desperately needed that.

Lastly, I’m just feeling burnt out. Working for a Charter School is a lot of work, and since we aren’t part of a teacher’s union, there’s not always a lot of protection from getting overworked and asked to do extra stuff. It stinks, but teacher burnout is a real thing, and I’m feeling it.

A new start may be just what I need to shake off the burnout. Plus there are a few other benefits to sweeten the deal.

Bring on the Benefits: I’m So Excited to Start a New Job

I’m crazy excited to start my new job. I’m giddy and nervous all at the same time. I don’t fully know what to expect, but I know I’ll have plenty of support and experience to do a great job.

The two biggest upgrades at my new job are the salary and the benefits.

As I said before, working for a Charter School doesn’t pay super well. It’s a big reason we worked so much at second jobs and took on extra coaching gigs while we were paying off our student loans. A low salary was a huge motivator to pay off our $73,000 of student loans in less than four years. We desperately wanted to start a family but knew we couldn’t afford daycare and student loans.

My new salary is almost $9,000 higher! To me, that’s an insane wage increase. My jaw literally dropped when I was talking with the HR guy on the phone. That alone made it seem like a no brainer. Now daycare costs could easily be covered!

The benefits package equally blew my mind. I will have to pay about $100 more in premiums each month, which stinks. But, the school district contributes $4,000 into an HRA account for my family to use for medical expenses EVERY YEAR!!!

My jaw dropped a little further, if that was even possible.

Are You Having Mixed Emotions About Changing Jobs?
I felt like a kid in a candy store. My eyes got wide and my mouth dropped open a little. My wife and I instantly started dreaming of our future goals.

The improvement of the benefits package sealed the deal. Again, it felt like a no brainer. My new teaching job will support the needs and goals of my family much better, and we’ll have better peace of mind.

If that wasn’t enough, I’ll be working shorter hours each day and fewer days throughout the school year. I think this will help with my feelings of burnout and feeling overworked, I hope so anyway. I can also pick our daughter up from daycare almost an hour earlier and get some good quality Dad time.

Plus, anytime you’re changing jobs, it feels fresh and full of opportunity. Right now I’m really optimistic and excited for a new start.

I’m Excited to Start a New Job, But That Doesn’t Mean I’m Not Heartbroken About Leaving

How I’m Celebrating and Mourning

I was going to title this section, “How I’m Keeping it Together”. But the truth is, most of the time I’m not keeping it together at all. Most of the time, like right now, I’m a complete mess of tears and heartbreak. I can’t believe I’m actually leaving. It’s even been hard to transition away from saying “our school” when my wife and I talk about teaching.

When I think about my students, I mourn for the lost opportunities to teach them and continue building relationships with them. I mourn that I won’t get to see them grow and develop and conquer new challenges this year. I won’t get to celebrate their successes and help them learn and pick themselves up after their failures.

In the end, I know my students will be okay, and their success isn’t dependent on me. They’re going to succeed no matter what just because they’re AWESOME! But that doesn’t mean it’s easy to walk away from them because it’s so damn hard.

The hardest part though is the prospect of not working with my wife Jenna. I can’t believe how lucky we’ve been the for our entire dating and married life. We got to drive to and from work together every day, pop into each other’s classrooms just to say hi, leave cute notes on each other’s desks, and share the same experiences of each school year.

It’s so incredibly sad to imagine a job that I don’t get to do that. I love her like crazy and she’s a huge reason I loved going to work every day. I got to work at a great job and see my wife every day. How many other couples get to do that?

It honestly makes me feel like Pam and Jim from The Office.

Are You Having Mixed Emotions About Changing Jobs?
Working with my wife has been the most amazing experience ever. I’m sad to leave it behind. But who knows, it could make our marriage even better.

Credit: The Office found on Degrassi.wiki

But at the same time, there’s a lot to celebrate as I start my new job. My family will be better taken care of with an increased salary and MUCH BETTER benefits package. We can achieve our goals a lot quicker, and daycare won’t feel like as much of a burden.

I’m also really excited to start fresh and see what opportunities wait for me. I can impact the lives of hundreds of new students in ways that I can’t predict. They have no idea what kind of nerd they hired either. I’m bringing all of my Harry Potter, Lord of the Rings, and Dungeons and Dragons nerdiness with me to share with my new students and staff. 🙂

Plus middle schoolers are hilarious by nature, so plenty of laughs and good times are in store.

Sometimes when you say hello to new opportunities, you have to say goodbye to other things you truly love and have forever changed you. That’s right where I’m at, and it’s hard, but it’s still really good.

Wish me luck this school year!

Leave a Comment!

Tell me about the last time you started a new job? Why did you make the change? How do you celebrate and mourn at the same time?

Our budget and goals changed our lives and it can change yours too.

Our budget and goals changed our lives and it can change yours too.

As an Educator and Personal Finance Blogger, Jamie has helped hundreds of families learn how to budget, save money, and pay off debt (go here to subscribe and start your debt free journey). Read our debt free story, “How We Paid Off $73,000 of Debt in Less Than Four Years”.

Changing Jobs is the Most Heartbreaking Decision I’ve Ever Made

8 Responses

    1. Thank you! I really hope so too. I just bumped into a parent of a student yesterday at church and we had a mini cry-fest talking about the job change. Leaving is hard, but it will also be a good thing.

  1. Jamie,

    I related so much to your post (feeling the heart ache of leaving, the excitement for something new). I wish you all the best as you transition to a new place. Your students and colleagues will be incredibly blessed to have you in their lives.

    Congratulations again,

  2. Jamie, man I empathize with you here. A few years back I left the Army to pursue a career in the corporate world. It was one of the hardest decisions I’ve ever made. I loved the Army, I loved what I did, and loved the camaraderie and mission. But like you, my family was growing (4 kids under 8 at the time!) and it was time for Dad to be home more.

    So we made the transition and it was definitely hard. I think what got us over everything though, was we did it for the right reasons. We did it for our family. I still miss the Army, but I wouldn’t change anything that we have done. We love the company I work for now and our family is much happier when we can be together nearly every night for dinner!

    1. That’s amazing Cooper. You said it exactly right, I’m glad I’m making the change to spend more time with my family. It’s so important.

  3. Congratulations on your new position! Is your wife staying at the old school, or did she find a new position at a another new school? Working together sounded wonderful.

    Good luck in your new position – now you’ll have a whole new crop of kids to teach money mastery to!

    1. My wife will still be at the same school so no change for her. And you’re absolutely right, my new school has about 650 middle schoolers that I can teach about money!

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