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Is This Your Dream Job?

Updated: Nov 16, 2021

Our goal is build a network of schools in which mission aligns with the goals and passions of every member.

Zen practices allows us to connect to our dreams. It helps us become aware of and drop away the conditioned thinking that often stands in the way of our even knowing what our dreams are. Zen practice also allows the aspiration to arise, to allow all people to connect to their dreams.

Alternatively, it is also said that sometimes your path finds you and reveals itself only gradually and only if you allow yourself to follow it.

As the wand merchant told Harry Potter, “The wizard does not choose the want; the wand chooses the wizard.”

The gift of Zen practice is that it allows us to appreciate and embrace the path when it appears. This is a great gift. As Roshi Robert Kennedy, Jesuit priest and Zen master, told me: So often when people’s prayers are answered, they reject the gift: “This can’t be happening. My prayers are never answered.”


At ICS, I always ask, “Is this your dream job? If not, come and tell me what your dream job is, and we will see where your dream fits in our schools.”

Our goal is build a network of schools in which mission aligns with the goals and passions of every member.

With students, we are always checking, “What are your goals?” “How does success in school fit with your goals?” With parents, we are also checking. “What are your aspirations for your child?” “Is being in our school a good fit with these aspirations?”

We often need to come back to this essential question. At Lavelle Prep, many students enter (maybe 10% of entering 6th graders) having been on Modified Promotional Criteria in their previous school. In New York City, modified promotion is a form of social promotion in which students are promoted from one grade to the next not by meeting the normal minimum promotional standards of 65% grade equivalent, but by achieving at a level as low as 10%. This is the system’s way of ignoring its failure to educate the most struggling students.

Sometimes parents and students are not even aware of the problem until high school, where there are no comparable modified standards for the State Regents exams required for high school graduation. Students moved along with modified promotion, as with other forms of social promotion, are on a pathway to failure.

Are We Still on the Same Page?

Parents enrolling students at Lavelle Prep are generally grateful for the opportunity to get off this pathway to nowhere and, instead, onto the pathway to college. They are warned and prepared for the heavy lifting that will be required by students and families alike. And yet, forewarned is not always sufficiently. When students struggle, parents are sometimes upset. We need to keep coming back to the initial goal with them. Are we still on the same page? Do we want to get your child to college?

Usually, the answer is yes. Sometimes, the answer is no. The lift is too much. It is just too hard, and parents opt to take their students out of Lavelle Prep. We respect that choice. Our college prep program is not for everyone. No school can meet the needs of every student or every family.

At New Ventures (where students enter in their late teens), while parent support can be crucial, it is much more the student’s decision to stay the course or to get out. All students entering New Ventures have already been frustrated and unsuccessful at another high school. It is critical that both we and they are clear on their aspirations: why do you want to graduate from high school? Where is this leading?

Some will find the New Ventures program fits them so well that they move through to graduation and college admission without a crisis of doubt. But most will hit bumps along the way. To finish or not to finish? Why stay the course?

Sometimes, we need only help them deal with some external crisis which is sapping their will and commitment. But often we have to ask and even re-ask, “Is this worth it to you?” “What are your goals, your dreams?” “Have they changed?”” Is a high school diploma still a critical step in achieving your dreams?” “Is this school still the best fit for you?”

Often it is.

But not always.

While we are able to help many to get back on track, some students choose to move on. Mostly to try another program in the hope of finding a better fit. Again, no program or school can be the best fit or even a good-enough fit for all students. Some sadly decide that have had enough of school and just give up.

In the same spirit, we ask our staff, “What is your dream job?”

I grew up in a world in which this was not a serious question. If asked at all, it was fatuous. I read and collected model railroad magazines from late childhood through adolescence and spent hours sketching plans for great train track layouts. When I was younger, I built HO of freight cars, and in my 30’s, when I bought my first house, I began to build a monster train layout in the basement.

The magazines I read were filled with wonderful articles about spectacular operating layouts which had been built by hobbyists in their spare time. It was obvious, if not always explicit, that this was where their passion was. The unspoken back story of that era was that most people worked in unfulfilling jobs, in which their most valued talents were never utilized, whether or not they made enough money to pursue a pretty expensive hobby.

I never finished that layout.

And while I still think of model railroading with nostalgia (although not very often), I have been fortunate to find fulfillment in my career, as sometimes strangely convoluted as my pathway has been. Now, wonderfully, I find myself in a place where my personal aspirations and organizational mission are aligned (hardly accidental since I had a major part in shaping our organizational mission). I realize fully the truth that we spend the largest chunk of our lives working and that finding alignment through work creates more joy than could be managed though model railroading.

Today, when so often people are adding commuting time to working time and when time for hobbies if anything, more attenuated, the alternative of working now for the dream hobby or retirement looks more and more like a bad bargain. Counting the days to retirement turns the best years of our lives into a prison sentence. And for too many people, illness, their own or their partner’s, robs their retirement of its joy. Too many simply die before they can enjoy it. Happiness really is to find joy in work.

Impossible? To find work which realizes your talents, within an organization whose mission is aligned with your most deeply held values and where all people are valued and treated with respect is a source of great joy and energy.

No organization, not even our schools, can offer everyone their dream job. But we can try. And we do try. Not because we are romantic do-gooders but because when our people are doing work which aligns with our mission and their dreams, our schools and our students thrive.

So, we ask all the time, “What is your dream job?”

I always say to staff, tell me your dream job, my door is always open (except that in our open architecture administrative space, my space has no walls or door.) Come and tell me your dream job.

I want to hear these dreams because as CEO, I am in a unique position to see opportunities that other managers are unaware of, places where a particular dream might mesh with an existing organizational challenge, offering a solution that without you, we never would have even considered possible. And even if a need doesn’t exist today, I am in a position to imagine your dream as an ingredient in a program or school not yet conceived, as part of a recipe for addressing a challenge which has not yet arisen.

As corollaries, we embrace two other obligations. If we are a poor fit for a staff member’s dream, we will tell them, “We would hate to lose you, but we may not be the best fit for you. At least not now.”

In our early years, a bright, ambitious teacher was always coming to me with proposals for jobs that would get him out of the classroom. Although I had hoped that he would grow as a teacher into a teacher leader, he wanted out faster. He was able to move successfully to an administrative position in another charter school. I hated losing him, but we were, and are, looking to grow instructional leaders with a passion for teaching, not a passion for getting out of teaching. We were not a good fit with his dreams.)

The more difficult challenge lies in working with staff whose dreams do align with our mission but who lack the skills (often interpersonal) for the job to which they aspire. These conversations are often difficult and not always successful. But they are always necessary. Patterns of behavior which stand in the way of promotion almost never go away if they are ignored.

The conversations take different forms. Some are quite casual, some have to be quite formal. With an aspiring male leader, it was a casual conversation. In our schools, the men are usually in the minority. In staff meetings and other gatherings, the “boys” tend to cluster. As a teacher, he followed this norm. A casual suggestion that “membership” in the “boys club” was probably an obstacle to promotion, that assistant principals needed to be perceived as leaders by all faculty, male and female, was sufficient. Once recognizing the pattern, he made the change.

With another very promising, aspiring leader, a more formal conversation was necessary to address the impression that her personal needs always came first. Again, the conversation was pretty much straight forward. A lot of people are under the impression that as they move up in the organization they will get to do less work, I told her. Actually, it’s the other way around – the higher you go, the more you work. She may have been angered at what she heard at first as a criticism of her work ethic, and it didn’t happen overnight, but she made the changes needed to succeed as a leader.

These are both success stories, as in both instances the future leaders took the feedback and matured into leadership positions much more quickly in our schools than they could have elsewhere. Other conversations are more frustrating. Not everyone responds as well. Some do not respond at all.

We have not been able to get everyone into their dream job. Not everyone even knows what their dream job is. And, dreams change. Yet our aspiration remains strong, to continue to improve the fit between the dreams of our people and the mission of our school. Our teachers and students, all of our people, like Zen students develop at their own pace. Some appear to be prodigies. Some like me are late bloomers. It is a great lesson of Zen practice to stop worrying about the pace of progress and to embrace and enjoy the unfolding.

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