Lessons From a Late Career Job Search

I would like to start this article by saying, to date, I have applied for exactly fifty-three jobs in the past three months (I have a spreadsheet), 54 if you count the one that I am getting ready to send once I build a portfolio of my work to share with that employer, oh yeah, and finish this article. I used to brag to people, in fact I still do, that I have not had to look for a job in 12 years despite working at three different schools. The reason for this is simple, in private education, especially if you stay in one place, people hear about you from other teachers or administrators who have worked with you in the past and they call you. This is a huge luxury when you are interested in administrative positions because often those schools just call you and if they like you, they hire you. This has worked for me twice in just three years, going from a teacher to a principal and then from principal to the head of school. Now, I find myself in a position to have to move to Washington DC from Orlando Florida and it has become crystal clear to me that nobody in Washington DC knows or really cares who I am, so I have to try really hard, which in the end, is not such a bad thing.

Before going on to what I have actually learned from my late career job search it might be good to qualify that I am not really sure that "late career" means. If you look at my profile picture you will find that I am not old but I am also not young. Technically, I could work another 15 years; and I am at the peak of my career, however, switching cities and competing with a slew of well educated, younger workers is a challenge...but I like challenges. So here we go, this is what I have learned, and I hope it helps anyone looking for a new opportunity.

Expect the Unexpected- Remember when you used to go into a job interview after researching a company and the position and they would ask you the questions you would expect like what is your experience with this or that or how would you handle this situation which is directly related to your job? That still happens, but it usually comes after some other stuff you might not expect like recording the answers to your questions on video, or telling someone how you would solve a complex problem using a bizarre set of tools. Never underestimate what is going to come out of the mouth of the interviewer, I was crushing an interview with a senior executive after spending nearly a whole day interviewing with key people in the organization. At the very end of the interview, she asked me..."is this your dream job?" I was not expecting that question, and although the job was highly desirable and I desperately want it, my dream job is actually pouring beer at craft brewery for free. I stumbled on her question trying to balance my sincere desire for the job with honesty. I would suggest if you get this question, to say "yes", and wait for the follow up.

Become really familiar with the ACRONYMS- If you need any further evidence that we are headed directly into a version or George Orwell's 1984, look at how we communicate today. DEI, SIS, LMS, CRT, IEP, IEPT, ELL, SME and SEL, are just some of the acronyms you need to brush up for education related interviews. On the business side it can be worse, SEO, UI, SMM, R&D, ROI, TLD, and the lists go on. Do not be caught off guard with any of these acronyms, and if you are, politely ask for a reminder; but there will be no saving you if you do not know the basics of your chosen field. There have been a few times where an acronym caught me off guard, luckily I was able to recall the meaning after starting my response.

It is ok to take a step back- I have managed to become the Head of School of a private school with 70 employees and over 300 students. I have ushered that school through a pandemic, set a bold vision for the future, completed multiple projects and hires that have positioned the school for success into the future, and now I have chosen to leave the position and move on. There is a part of me, even still, that sees any job lower than the one I have as a failure, my generation (GenX), tends to see any step backward as failure, which is ridiculous and outdated. I admire the generations below us, they understand work/life balance and experiences over money and power. I too am learning that I do not need, or really want, to continue working 60-70 hours a week so I can say that I run the school and collect a bigger paycheck. After running a school through the pandemic I can honestly say that I am looking forward to something with a little less parent management and stress and a deeper focus on helping improve education. If I make less money and have fewer people to manage, I am ok with that, and you should be too.

Don't expect a response from everyone- I am probably a bit more of a narcissist than most, so when I started applying for jobs I really believed that it would be easy to find one and that it would just be a matter of picking the best one. Ok, I wasn't that confident. I do however have a great deal of experience in education, I am at the top of my profession with a graduate degree in leadership, a recent fellowship in executive leadership and many years of experience as a teacher and administrator . Of the 53 positions that I have applied for about half have contacted me back, most of those were rejections and the others went into varying levels of discussions and interviews before those too became rejections. You have to be ok with never hearing back. I have heard a variety of advice on contacting employers after you have not heard anything back. Some say contact after a week, two weeks, a month. I never contact a school or company where I have submitted an application unless they have called or interviewed me first. If they do not initiate the process I see no need to chase them down to review my application. You may disagree, but I believe that it is important to give them the respect of space and time to deal with the search they are conducting, if I am not in the short stack of applications they are likely not interested to begin with.

There is a lot of cool stuff happening out there- It is funny, when we are in the four walls of our school or offices we forget about how amazing human beings are at creating things. As I have searched, applied, interviewed, and searched, applied and interviewed again I am reminded of the amazing companies, schools, non-profits and government entities are pushing the boundaries of what can be done. Non-profits I have applied to are advancing diversity, equity, inclusion by funding incredible schools with unique approaches to education. Companies are creating tools that allow teachers to bring learning to life and save teachers time so they can build better lessons and experiences for their students. Government entities are creating programs where gardens can be developed in the inner city to help urban students understand food and health better. Non-profits are being formed every day that seek to address the injustices of the past and put all students on the same footing. There is so much happening out there that I am unaware of because I have spent so much time managing crisis; but it is incredible and gives me hope for the future. And lastly, schools, my favorite places in the world are trying incredible methods of educating students. Coming from Florida to Washington DC was an eye opener. Washington DC has so many innovative schools with so many amazing things happening in them. There are all boys schools and all girls schools. There are Quaker schools and Abby schools, there are schools where the students call the teachers by their first names and those where all the students have to wear a blazer and tie every day. Some schools exist in DC where the city itself is a classroom and education is lived amongst the monuments and museums. How can you not get excited about that.

These are not the only things that I have learned, but they are a sample of the reality that exists in modern job searches. It is easy to get a little down when you are working really hard to find a job and you can't, to be honest I am being very picky about what I apply for so I am not shocked it is taking longer than I would like. I will freely admit, I have had some struggles, not the least of which is the fact that I am living nearly a thousand miles away from my family while I finish the school year in Florida and my wife works from DC. I guess the point of this article is to say that it is ok. I have worked hard my whole life and I and I will continue to work hard finding my next opportunity. To this point, I have a pretty good record of getting things done, so I will keep hammering away at it knowing there is a perfect job for me, waiting in Washington DC or working remotely from my kitchen. So I will keep writing cover letters, tweaking my resume, and calling back to check up on the status of my application (but only the ones that have contacted me back); but also, I will continue to learn from this awesome experience and maybe even share it with you.