How I Found a Job: Episode 1 ~ Unhumble Beginnings

While applying for a teaching job a few years ago, I posted a few notes on Facebook about the experience. I wrote them in an attempt to keep my sanity and sense of humor while facing a series of setbacks. As it seems like many people that I know are in this position, I have decided to post them here over the next few weeks. I wish all searching for jobs the best of luck. 

Three years ago in a state not so far away…

Unhumble Beginnings 

The title here is a bit presumptuous as I have not “found a job.” By “found a job,” of course, I mean have gotten hired. In all honesty, I have “found” plenty of jobs. Searching for employment as a High School History teacher has been an experience. At first, every time I “found” a job posting, I immediately got excited. “This is the job,” I’d say to myself. I imagine using my first paycheck to take my wife out to a fancy dinner. I imagine getting to know colleagues and going to the bar on Friday after school. I imagine going to the Thanksgiving football game. This feeling tends to flee when weeks or months later the position has been filled (usually without my even getting an interview). I no longer have fantasies when a job is posted. I am yet to be in the doom and gloom phase – but I am a bit gloomier.

I started the job search like a hot shot. When my wife, Lacie, would try to be reasonable with me and attempt to discuss “Plan B” (if I do not land a teaching gig), I brushed her off calling her a “naysayer”. I truly believed that I would have a job much sooner. I have been actively searching for a position since February. It is now the end of June. My position as Senior Program and Training Manager at an AmeriCorps program is wrapping up tomorrow. I am now panicking. Lacie has been supportive encouraging me to take the unsteady “substitute teaching route” for the year. She realizes that I am in panic mode and is trying to help. I am no longer the hot shot job searcher that I was when I began the search.

I remember starting my job search. It was February 25th at a teacher recruitment fair. I had individualized application packets made for every school system with a school specific cover letter, a resume, a copy of my teacher’s license, three glowing references, original college transcripts, and my teaching portfolio on a CD. This was in stark contrast to many others at the event who only brought resumes. At this fair, I was on. “Impressive,” is what a few school districts called me. One principal even put an asterisk (*) on my resume indicating that he was very interested in me. I left that day thrilled. “This is going to be easy,” I thought.

This feeling would last a month and a half. At that point, I e-mailed the principal who was interested in me. He informed me that it did not look like they would have any openings next year as he had originally thought. He thanked me for my interest in his school and wished me the best of luck on my job search. That last sentence would be typed many times to me in the months to come. Each time I hear it, a piece of me wants to crawl back to my old job.

At the end of April, I had my first interview! I spent two weeks learning everything I could about the school district and the people I would be interviewing with. That day, I left work early, went home to put on my navy blue Brooks Brothers suit, and drove over to the interview. I was 40 minutes early, so I sat in my car for 25 minutes before heading in. I was escorted to a classroom to wait for the interview. I paced around the room looking at student work for a bit before settling in a chair and re-reading my teaching portfolio. In my mind, I was debating if I would appear more engaged if I were reading student work when the department head came in to get me. In the end, I nixed this thought and re-read a lesson plan that I was particularly proud of.

At this point, it would be good to tell you about myself (this will inform the current story). I took a break from college to do City Year, an AmeriCorps program. It was during this time that I realized that I wanted to be a teacher. Upon completing two AmeriCorps terms, I returned to school and majored in secondary education/history. I received Honors in Student Teaching and had a good GPA. I graduated after the fall semester and decided to work for City Year to train AmeriCorps Members on how to work with middle school students. I stayed for two and a half years and had some great experiences with the program. I am very proud of the work City Year and AmeriCorps does and really believe that it is helping to change the world and open up education to more people (upon completion of an AmeriCorps term, corps members receive a sizable award for college).

At the interview, I was asked “tell me about yourself.” The above paragraph was the starting point to my answering this question and then I went a bit specific into some of the amazing things that I have been a part of with City Year. The department head’s next question was, “OK. In terms of teaching, tell me about yourself.” Apparently, the speech on my love for national service was ill-placed. For the rest of the interview, I kept my answers on point and relevant to the school. In the end, I was able to pepper in some of my AmeriCorps experiences into the interview without overloading it. I walked out of the interview believing that I may have a shot. I did not. I received an email saying, “we have interviewed many fine qualified candidates like yourself for this position. We thank you for your interest in our school and wish you the best of luck on your job search.” I hate those oft-repeated words.

The next few weeks were very slow on the job front. I spent lots of time writing specific cover letters to over 40 school districts in Massachusetts in preparation for a job posting. Everyday, I checked,, and Every Sunday, I bought a Boston Globe and checked out every school systems webpage searching for a posting. When something came up, I printed my application packet and shipped it off. I was on a mission to find employment.

This is where I am today. Applying for a job has been very stressful. As a means for reflection and to find humor in stressful situations, I will be documenting this search. While I hope that it will end sooner rather than later; here is to my current journey!

For more from this series click the links below: 
How I Found a Job: Episode 1 ~ Unhumble Beginnings 
How I Found a Job: Episode 2 ~ “A Highly Qualified Applicant” 
How I Found a Job: Episode 3 ~ Advice from Mom
How I Found a Job: Episode 4 ~ Tales from the Road

About Michael K. Milton

I teach students Social Studies at Burlington High School. When I became a teacher, I believed that students would frequently give me apples. This has not happened (not even a Red Delicious ~ a name which is a misnomer). However, my school has given me a MacBook Pro and an iPad in an effort to right this wrong (I assume). I'm very lucky to work in a 1:1 school.
This entry was posted in How I Found a Job, Reflection and tagged , , , . Bookmark the permalink.

9 Responses to How I Found a Job: Episode 1 ~ Unhumble Beginnings

  1. danriles says:

    I am glad you are posting this. When I started teaching, there were many opening, and few teachers looking for them. The buzz was a shortage of teachers with the impending retirements of a cohort of older teachers. With the economic downturn affecting schools so significantly, there is now the reverse. There are many qualified teachers with many fewer positions available. How one navigates this procedurally and emotionally is excellent information.

    • @42thinkdeep says:

      Thanks! It really took me a long time to get into the position that I am in now. Granted, I’m thrilled things worked out the way they did and I am in Burlington – but it took a very long time (and a lot of rejection). I debated finding another career path altogether. Luckily, things turned out alright in the end.

  2. Great post. It is such a hard process. I do believe that things work out the way they should, just not always the way we think we want them to, when we want. I am glad that you hung in there. You have some fabulous ideas and great passion. It would have been such a shame to have denied students the chance to have you as a teacher.

    • @42thinkdeep says:

      I really appreciate your comment! I think part of what got me through the it was writing about the process. Which is partially why I have been keeping this blog (to reflect, laugh, and join in on a discussion).

      Thank you for all of your ideas that you have shared with me!


  3. I am a teacher from a Louisiana school and I must re-apply every year. I have the option of doing a mini interview session to stay where I am or do a real job search with lengthy interviews if I look elsewhere. STRESSFULLLL. Thanks for sharing your story.

  4. Pingback: How I Found a Job: Episode 2 “A Highly Qualified Applicant” | Michael K. Milton ~ @42ThinkDeep

  5. So many people are going to appreciate this series. Thank you for writing.

  6. Pingback: Going Meta: Cataloguing My Past Two Years of Blogging | Michael K. Milton ~ @42ThinkDeep

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