55 and Searching: Job Hunting at a Later Age

by Richard F. Flynn

You want or need a new job. You are seasoned in school system leadership, over 55, good at what you do, and have friends and enemies to prove it. Yet you have reached an age and experience level where you know a job change will be difficult.

If you have done things right as a superintendent, you’ve probably made people mad at you in at least three states. That was my situation in 1995 when I found myself in the search for a new job at age 58. More about that later.

If you are a seasoned school district administrator and find yourself out of a job or looking for a new position, do not panic. Remember, you can be successful again. But be sure of what you want because you likely are going to obtain it. After all, being over 55 and wanting to stay in the superintendency rather than retire is somewhat unique. Most of our aging colleagues cannot wait to retire from their increasingly demanding jobs, so they say.

These practical considerations, based on my own recent experiences, are meant for those who retain a passion for serving children, a commitment to public education, and the confidence to remain a superintendent. The odds of landing the job at this age are a little higher, but the credentials are simple: You must be persistent, lucky, and a little crazy.

A Unique Juncture

Not long ago, a candidate for a large-city superintendency in Missouri was billed as one of America’s premier superintendents by school board members and the community. He was and is premier because of accomplishment, reputation, and years of successful experiences. However, at 59, he chose to retire and reportedly is living happily ever after.

While I consider myself good at what I do, I don’t put myself in the same league as the premier superintendent. (I did have a board once that agreed I was the best superintendent in the school district, but only after a motion to nominate me for the state superintendent of the year award failed due to the lack of a second.)

Because I certainly didn’t want to retire, the board’s decision not to renew my contract left me at a unique juncture. I possessed (1) a passion to continue working at what I do best, even if I’m not recognized as premier; (2) a mindset to call home wherever the driveway is; and (3) the chance to start my third job search in 20 years.

Not all of us in school leadership are premier quality, but most of us know what is the right thing to do in most situations and have much to contribute to the educational system. So it remains a professional mystery to me why many boards of education fail to grant full consideration to those of us who are seasoned professionals. Administrative leadership and management of schools are our second-nature behaviors. We know what is coming over the horizon. We know where the snakes are and how to beat the grass to get them on the run. Plus, we have been long-time searchers for educational equity and improved student performance.

What fledgling 35-year-old superintendent knows that as well as the experienced CEO? The mystery is why a corporate body of 5 or 7 or 11 people cannot recognize the difference.

I found my search for a new position to be a game not unlike the state lottery. If you play long enough, you will win something. Perhaps you won’t win the $10 million reserved for the premiers, but your award can be a great prize and probably a better job than the one you just left or are about to leave. It is amazing how many superintendents’ positions are open at any time of the year if you are not geographically bound.

The optimum open season lasts from around the winter holidays to the end of April. This is the best time to get in the hunt, when the market is full of job opportunities across the country. It is a time when you have more freedom to select a school community by size and location. Getting what you want outside this window will be more restrictive but not impossible. You must be confident about your competence and persevere during the search, even though you may think at times all those people in the last three states were right about you.

Preliminary Steps

The prerequisites for a successful search at a later stage in life are not minor. First, you have to want to work. This commitment takes precedence over a home mortgage, car payments, or your family roots.

Second, your retirement plan (whatever that is) must leave you clear-headed, foot loose, and right with the world.

Third, you must sincerely believe you are the best thing going in school leadership and are not tired of behaving as such.

Lastly, you must believe your years of experience have produced a resume second to none. Your past experiences truly have made a difference in the lives of students, teachers, and administrators. The resume shows that entire communities were better off because of your work.

Once you satisfy those prerequisites, it is time to begin sending out your professional packets at a rate of five per day to boards that are seeking new leaders. Before too long, a pattern of responses will form, consisting of short-range cutoff dates, "Dear John" and "Dear Jane" responses, and requests for more material.

The process will annoy and amaze you. For example, after having submitted a comprehensive, 10-page resume, you will receive a three-page official application form designed by a search consultant. This application will be accompanied by a request to copy your extensive resume onto the consultant’s form, which probably will not fit your typewriter or computer printer.

Be prepared to go through 200 sets of hoops (for as many jobs) as they are placed in your search path. Some of these hoops will astound you. Expect to write some essays. I was both amused and bewildered when a small Colorado district asked me, a candidate from a district of 20,000 students in the Southeast, to "discuss the academic needs of its community." It was pointed out that failure to respond to this and four other essay topics would constitute an invalid application.

Yes, I responded to all five. No, I did not get an interview. I don’t know if the quality of my essays led to the rejection letter, but it certainly was not because of my failure to respond.

Expect an interview rate of about 10 percent. That is, if you apply to 200 school boards, you can expect invitations to interview with approximately 20 school systems. Anticipate that several of those districts will not offer to pay your travel expenses. At least one already will have picked its new superintendent but is afraid of being accused of shortsightedness or discrimination unless the board waltzes through the charade of a national search. Two districts I encountered had advertised nationally only because of a split opinion by the board of education over whether to conduct a prestigious national search. The majority already knew that no out-of-state candidate would get their job.

Valued Qualities

For variety in your job search, consider sending 20 or 30 application packets to selected colleges and universities. The Chronicle of Higher Education each week lists numerous faculty vacancies in colleges of education. Who knows, maybe one of them will want you because of your talent, skill, insight, and character. Service-oriented universities value these qualities.

As you wait for responses, keep in mind that deliberations in the ivory tower are laborious and slow moving.

You just might get a call from a faculty search committee even though you have not tackled formal research since graduate school and the only writing you have done has centered around court preparation, Public Law 94-142 hearings, responses to parent complaints, and those board/superintendent communication pieces. None of these, by the way, impress deans and department chairs.

From these two hunting grounds—practice and the professorship—receiving 15 job interviews is not bad in today’s world of the migrating superintendent.

Updated Records

At the job-seeking rate I’ve suggested, you will have more than 200 resumes in the job market after 45 days. In the process, you will have made contact with at least 20 search consultants. To keep your many pieces of search correspondence organized, you need to create a progress chart. I called mine the book of opportunity. (The premier would go high-tech if he or she needed such a book). Keep your records updated.

You will need a quick view of the information when the phone rings and a consultant or search committee member invites you to sit for an interview. Act overwhelmed with excitement and enthusiasm over the phone.

The caller will be anxious to tell you about the ground rules for the next step. This has to be the only school district on your mind at that moment. Tactfully, try to get the school board to use its travel agent to make your arrangements for the interview visit. At one point in my search, I had $3,000 in plane tickets charged to my credit card. School districts can take forever to reimburse you.

Expect on most days for the postal service to deliver you a "Dear Jane" letter. It is a simple piece of art. Most read something like this: "Thank you for your application. Your credentials along with those of 199 other highly qualified candidates were outstanding. After a difficult screening process, your name was not selected for further consideration. Good luck with your future professional endeavors. Sincerely yours."

Go back to your opportunity book, red-line the contact and consider it a loss for the district as well as yourself. Move on in your thinking and master plan. Be alert to your self-esteem index when dry spells occur. It is not the time to abandon the process. Remember your focus and persistence. Do not be surprised if school boards (and especially universities) take forever after application cutoff dates to determine if you remain interested in them. The cutoff date for one of the applications I submitted was in October, but the interview did not get scheduled until the following March. It is impossible to list all the reasons why this happens. You will learn those as you go through the process.

When you discover after an interview that you are not the person selected for the job, do not ask a consultant why. In the middle of my search process, I did a dumb thing. I was in a dry spell. My self-esteem was low. I composed and sent a letter to 10 consultants whose stationery was filling my opportunity book’s rejection column.

My letter spelled out how good I was and what I thought the problem with me as a candidate might be. Dumb! I asked to remain on their "serious consideration" list. Dumber! I only heard back from one. She called (nothing in writing, smart lady) and chatted about how solid my resume appeared and how boards of education often operate in unique and strange ways. Since I already knew such things, I learned not to do that anymore.

Touchy Scenario

Of course, one’s fortunes in a job search as extensive as this one can change quickly.

Twelve interviews had come and gone for me. MasterCard had upped my credit line to $29,000, and I had finished somewhere between third and last place in my first dozen interviews. Suddenly, within a five-day period I was called and scheduled for virtually back-to-back interviews in West Virginia, South Carolina, Connecticut, and Kentucky for three superintendencies and one university teaching post.

  • Job 1: The West Virginia superintendent position looked like a really good one. I felt positive about the interview. The board members were focused and really nice. I left feeling at the top of my self-esteem ladder. I was almost a premier superintendent that day, and they would let me know my status in "a day or two."
  • Job 2: A day later, I arrived for the South Carolina interview. After about 20 minutes I knew I wanted the job but sensed the board did not want me. It was obvious someone else already was picked. However, they were extremely polite people, even if not particularly focused on me or my interview. They would let me know in "a day or two."
  • Job 3: On to urban Connecticut. This was a great interview. This was a great district with good people who knew what they wanted, and I just might be it. I did well in the interview—as one of eight candidates. I was looking forward to going back in a few days. I was excited, feeling there was no reason this was not to be my new job. Again, they would let me know in "a day or two."
  • Job 4: A few days later I had my interview for a university professorship. Contrary to my prior experiences in higher education with the extended decision-making process, the search committee pledged to make a decision that day. True to their word, the search committee contacted me at the end of the day. They really wanted me. Would I take the offer right then? I explained I was in the hunt for jobs 1, 2, and 3. Reluctantly, they said they understood and gave me a week to decide.

On the flight home, I explained to myself all the reasons to accept and/or reject the various pieces of this four-job scenario. It was clearly decision-making time. After all, this was what I had been building up to over the past 12 months. The roller-coaster effect of exhilarating interviews followed by rejections and the personal debate over practice versus professorship collided with the urgency to finally make a decision.


Most importantly, I finally had a decision to make and it needed to be the right decision for the right reasons—not just because I had a long-awaited offer in hand. Two days after arriving home, I called the university and said, "Yes." I wanted the position, the new challenge, the new start, and they still wanted me.

No sooner had I hung up from my acceptance call than the phone rang. It was Connecticut calling. I had made level two of the search and was one of two finalists. This was the closest I’d come in my superintendent searches over 12 months and what a great district! But I quickly informed the consultant I had accepted another position and I was withdrawing from consideration. (Did I say you had to be half crazy?) She seemed sorry to hear that and told me I was a favorite of the final two.

Three days later, the calls arrived with news of jobs 1 and 2. I was not a choice in West Virginia or South Carolina. Then, out of nowhere, Job 5 called and said I had made the short list of 3 for an interview. I didn’t even realize I still was being considered for Job 5—a large district in Florida. The only contact I had was a board member’s phone call on a Sunday night two months earlier. Their deadline was one month past. With a surprised voice I politely explained my situation.

My decision-making period came and went quickly. I made a decision and honored it. I didn’t look back. It was not a time for second guessing. I had a new job at 58. With my self-esteem flying high, I called the moving company. I was going in search of a new driveway.

Now, 1 1/2 years since my job-hunting exploits, I can say that maybe this professorship is the best job I ever have had. Maybe I will be a premier professor someday.

The Age Issue

Throughout my search, two issues did emerge now and then: my health and age. These did not arise during or after an interview, but they sometimes emerged after the receipt of a rejection letter as I wondered if a board of education would doubt my stamina to do what was expected. I knew better, but opening two "Dear John" letters in one day caused me to conjure up any reason to explain away low self-esteem.

At the point of rejection, older candidates tend to look for any reason to satisfy the moment. Age discrimination occasionally entered my mind. I think this probably also happened to me when I interviewed for my first position in 1975. Of course, then it would have been a question of being too young. I found that maintaining high self-esteem, by acting with confidence and a mindset of competence, always made this concern disappear.

I never seriously thought either of these issues were factors in my recent job search. Boards and search consultants seemed careful to avoid any violations of the law.

I dealt with the issues of health and age on my resume. I always attached a photo of myself. I explained my health status in a brief statement and made it clear how old I was. If a school board or consultant wanted to use these factors to eliminate my name from contention, I made it easy for them to do it at the paper stage or during the screening process. I wouldn’t want to work for an organization that would focus on these issues. Interviewing would be a waste of everybody’s time.

Defying Odds

Being 55 or older is not a limiting factor for premier candidates in the superintendency. Their reputations carry them from job to job. However, not enough premiers exist to go around. The country’s 15,000 school districts will hire the majority of us on other attributes: passion, perseverance, and genuine belief in what we have to give.

Because of our commitment to doing right things, we will find ourselves in trouble sometimes with boards of education and various factions of the community. We are going to move on. It is just a matter of time.

The decision to move—to begin another job hunt—involves checking the odds. Yet even when one of the odds against us is that career-defying age of 55-plus, we must remember that warriors always go to a hunt with a passion for what they do, a commitment to the right thing, and a confidence to win the hunt.

Richard Flynn, assistant Professor of educational leadership at Murray State University, Murray, Kentucky, worked for 20 years as a superintendent in Ohio, North Carolina, and South Carolina.

Job Hunting Resources in Educational Leadership

Consultants’ Counsel: Using Age To Your Advantage

Long-time superintendent search consultant Kenneth Underwood says he used to tell candidates if they were over 55 they didn’t stand much chance of landing a new superintendency.

With the size of candidate pools growing smaller all the time, he doesn’t say that anymore. "I think those days are gone. The magic number of 55 is gone," says Underwood, who directs Harold Webb Associates of Winnetka, Ill.

The general consensus, gleaned from interviews with a dozen search consultants across the country, is that advanced age no longer is much of an issue when a school system leader applies for another superintendency.

Experience is more important than age. The focus now, says Richard Castallo of Education Management Associates, based in Syracuse, N.Y., is on "competence, enthusiasm, and energy." His view was repeatedly frequently by his counterparts.

Here’s a summary of the advice offered by the search experts to those over the age of 55 in the hunt for a new superintendency.

  • Stress experience. Says James H. Warren of Bickert, Prophet, Warren, Barnes and Associates, based in Glen Ellyn, Ill.: You need to "package your experience and accomplishments" and show the quality of past work so it fits the hiring district’s needs.
  • Keep informed. Jacqueline A. Roy, a consultant based in Cambridge, Mass., counsels candidates to stay on the "cutting edge" regarding school reform and technology. Show you have new ideas and continue to move in a forward direction.
  • Plan to provide stability. John Allen of the Illinois Association of School Boards says older candidates need to realize the No. 1 question the school board will want to ask but won’t is: "How long will this person be with us?" So anticipate the question and address it with the board during the interview. "Take the board off the hook," he says.

On the same issue, Robert Ferris of Ferris and Associates in Fullerton, Calif., says: "Make it clear you are not using the position as a stepping stone. Commit to be there a considerable amount of time." Bill Attea of Hazard, Young, Attea and Associates in Northfield, Ill., advises candidates to show a willingness to stay in a leadership position for about five years. And do not, he adds, mention you are looking for a job to retire from.

  • Be open about your age. "Play up its value," says Ferris. "Play up experience and longevity."
  • Present yourself energetically. "Stop acting, dressing and looking like you are 65," says Herb Pandiscio, a consultant in Avon, Conn. "Remove the words ‘retirement’ and ‘pension’ from your vocabulary." Older people may act older than they are by a lack of energy, excitement, and enthusiasm. That shows up in an interview.
  • Research the district. If you have good superintendency experience, many school districts have particular needs that a more seasoned educator could fill.