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The millennial in me: Confessions of a Gen Xer

5 min read


A recent piece by Forbes contributor Liz Ryan extolled the Millennial Way, or at least some of the logic behind it. In her column, Ryan sought to assuage concerns of baby boomer parents and frustrated executives, telling them that Gen Y’s approach to life and their attitude about employment is healthier and more balanced than we think and something that all of us should have done years ago.

“Anyone who argues for a more human-centric approach to work,” she wrote, “is a hero in our book, and that quality is what millennials are most well-known for. They aren’t willing to fall in line and take a lousy job just to get an apartment that’s the envy of their friends. What good would the apartment do them, if they hate their job and therefore hate their life?”

In her well-articulated defense, Ryan highlighted two millennial propensities: an aversion to drinking the corporate Kool-Aid and a capacity to reinvent themselves as circumstances and interests warrant.

Our youngest workers, she writes, were just getting started (or thinking about doing so) when corporate scandal and widespread layoffs punctured their parents’ golden balloons. The promise of peace and prosperity in exchange for decades of hard work and sacrifice to the corporate cause went up in recessionary smoke. Now, their children, fresh off of an economic near-collapse that almost shattered their own dreams and still put many of them on hold, remain uncommitted to the corporate credo, an irreverent quality that sends tremors of fear down the spines of upper management.

Ryan also noted that millennials are apt to undertake a career 180 if they see the folly in their original area of study or professional choice. Just because a person trains in one area is no longer a reason to remain in that space, particularly if it fails to deliver in terms of job satisfaction and stability.

While Ryan’s article was a most-enlightening take on millennial attitudes and practices, I also felt that she was also talking about me, and, I suspect, many other Gen Xers.

Recently, I had a difficult decision to make. I knew that I was leaving my post as head of school and needed to figure out how best to move forward professionally. I decided that I was going to pursue a new position in school leadership — my professional pathway for the previous decade — or become an executive coach and consultant, a logical extension of my work in the leadership trenches.

The first option was the safer one, no doubt. I had trained extensively in educational leadership and boasted three advanced degrees (including two masters degrees in education and rabbinic ordination). I had spent 15 years in the field and felt comfortable in my capacity to lead another school forward. Clearly, assuming a new principal position would have been the most logical next step in my career path.

But school leadership also demanded that I work for numerous employers, real or imagined (i.e. the board, staff, parents, students and all stakeholders). So long as I was an employee, I would have limited opportunities to satisfy my entrepreneurial and other interests. I was eager to set my own schedule, to be my own boss, to decide which opportunities to pursue and offers to accept and which to turn down. I wanted the freedom to become a capitalist, a new concept for many of us in education. And I wanted to do it in a manner that fell neatly in line with my personal interests and values.

I was also reluctant to throw my future in with the ‘assurances” of an administrative position. I had been burned before by lofty, long-term visions of partnership that prematurely went sideways. The promise of success and stability in exchange for hard work and commitment had proven itself to be empty for this Gen Xer.

Still, going independent was quite risky. How long would it take before I could get my footing and build a client base? How would I pay the bills as I credentialed further and learned the ropes?

After much soul-searching, I decided to take the plunge. I enrolled in a PsyD program in I/O, took coaching courses, developed a company name, profile, logo, website — the whole nine yards. In a matter of months, I want from someone who was inactive on social media, with only (largely unused) Facebook and LinkedIn accounts, to someone who had to quickly learn about tweeting, posting, blogging and contributing to professional group dialogue. I began prospecting and networking in earnest, all with the hope that it would bring me close to a place of professional and financial independence. Talk about a career 180.

It’s hard to know at present whether my current pathway will result in the same level of financial security that comes with a contracted position in school leadership. One thing that I can say is that I have never felt more free and in control of my situation despite the many uncertainties that accompany it. I believe in myself and in my abilities. I trust God has invested the necessary talents and energies in me that will allow me to succeed in making a difference for executives who struggle to lead their enterprises in a rapidly changing and unforgiving 21st century climate.

I cannot say that I embrace every aspect of millennial thinking — I still believe in the virtues of hard work, loyalty and relationship building. Still, I feel that can relate to Gen Y style thinking more so than ever before. It may not be great for corporations, but it can be a real boon for those who seek to live a life of freedom and opportunity, unencumbered by others’ values and sense of achievement.

Naphtali Hoff (@impactfulcoach) served as an educator and school administrator for over 15 years before becoming an executive coach and consultant. Read his blog.