Defining Success for Myself

This is a complicated story. So let me start with some background before explaining what is going on right now.

First, for those of you who don’t know, I currently have three different jobs. I own ClassMax, which is my heart and my baby. It is an education software company I started almost three years ago when I was a classroom teacher. It started as a special education tracking system and grew to become a standards tracking, behavior tracking, hall pass tracking, all-in-one classroom management platform for teachers. Two years ago, we bridged out and began selling to whole schools, and this past school year we started working with five different school districts. It has been a wild ride and I can’t believe what it has become and where it is headed.

As any new business owner will tell you, building a company (especially a tech company) is not cheap. Every penny we make goes back into the platform. Not to mention, we have amazing investors who have put hundreds of thousands of dollars into growing ClassMax. All of this means that I will be the last to be paid – and rightfully so. I took a paycheck in the very beginning so that I could work for ClassMax full time while we worked on developing and launching (the most time intensive part). But in the past year, I have stopped taking a paycheck so that everything could stay within the company.

In order to pay the bills on the home front, I took a position a little over a year ago working with an education company doing virtual coaching for teachers, administrators, educational leaders, and district coaches. I carry a case load of 40 participants and meet with each of them individually every two weeks. In addition to this part of my work here, I also started traveling extensively doing workshops and program launches for school districts. It was a great way to keep me active in the education field, while still giving me the flexibility to run ClassMax.

All of that sounds great and worked fine for a little while. But recently, the load I’m carrying has grown heavier than I can manage. Not to mention, Chris has been left to manage our home and kids while I travel. And remember, he just took on the role of Executive Director at his theater, so his schedule is not any more fluid than mine. It has resulted in a tight shuffle and lots of tension at home. Remember this past summer (or was it last summer???) when Chris and I went to marriage counseling? Well, I am so glad we did because we have relied on the communication skills we learned there to navigate this really difficult period, which means we are coming through it strong, but that doesn’t mean we want to stay in this situation forever.

By December, Chris and I were both about to break. He and the kids both came down with the flu at the same time and, while I was able to stay and nurse them for a few days, I ended up having to leave for another work trip with Chris, sick himself, taking care of the two sick kids. Between that and Gracie making an off-handed, casual comment about her being used to me not attending anything at her school anymore, I knew I had hit my tipping point.

I started reaching out to principals that I knew in the area asking if they had any coaching positions available or that might become available over the next year. Within 24 hours, I had a job at the same middle school I was teaching in before I left for ClassMax. 24 hours after that, I quit my job with the coaching company. ClassMax will continue running as it does right now, with the help of our team and, honestly, I will probably have MORE time to give it without all the travel. Everything fell right into place.

But my pride was not on board.

“People are going to think you have been unsuccessful if you go back into a school,” I thought.

“What will people say about ClassMax?” I wondered.

“It’s a complicated situation. How will I explain this to people?” I asked myself.

And so I’ve been doing some soul searching in the weeks between Christmas and now – and let me tell you… it was ugly. I asked myself really hard questions about how I define success and how dependent I am on what others think. I’ve thought through my need to be not just liked, but envied (God, that sounds so horrible to say out loud). My need to be better than. Above board. The highest achiever. I’m not very athletic, but I am one of the most competitive people I know. I’m constantly keeping a running list of where I am versus where other people are and I DIDN’T EVEN KNOW I WAS DOING THAT. (I’m so embarrassed writing this out loud…)

But when I think about making a professional choice that is right for my family – I’ve made it. This is it. It’s filling my days working with teachers – encouraging them, creating with them, guiding them, exploring with them. It’s building relationships and trust and having conversations where I’m looking someone in the eye and not through a computer screen. Part of that satisfaction has come from and will continue to come from my work with ClassMax and part of that will come from my new work in a school again.

My word for this year is PASSION and on my search for what I am passionate about, I’ve discovered that my path to passion may not look traditional or even successful to others. AND THAT’S OKAY. The truth is that I will probably never be one of those people who take a 9-5 job and am completely satisfied. My passions are wide-ranging and my interests are diverse and complex, which means my career path will probably always look a little untraditional.

For a long time, I struggled to fit everything into a nice, neat box with a job title that everyone understood so that everyone knew how important I was (ugh – these deep self-reflections I’ve had have not been pretty, you guys). “Hi, my name is Katie and I am a ____________.” But the longer I explore all these areas of education and all the things that excite me and drive me, the more I realize that it’s okay for me to not be able to explain my career in one sentence. It’s okay to not have a job that people can easily define. If someone doesn’t understand my career path, if I can’t give them a clean description of what all I do, if they can’t tell how “important” the work I’m doing is based just on my job title, I’m okay with that. Or, at least, my ego is learning to be okay with that.

When it comes down to it, the ability for others to define me is completely irrelevant to how I define myself.

I can’t wait to be back in a school again where I am not spending all day in a home office by myself or in airports or hotel rooms. Chris and I are so excited to spend full WEEKS together again and the kids are ecstatic that I will be working at the school where Bean will be going next year.

So, here’s to a new adventure! The next step in my education career and the RIGHT step for my family and my future. Doesn’t get much better than that!