CAREER ODYSSEY

WHO’S IN CHARGE OF *YOUR* CAREER?

Happy Monday Peaceniks. Ready to work?

My greatest fear: Becoming irrelevant.

My mantra, “Wake Up Stupid Everyday,” was born from this paranoia - the constant, nagging anxiety that I might lose touch, fall behind, and arise one day to find the world had passed me by. This prospect drove me to start teaching at New York University twenty years ago. My theory was that if I taught a class on the state of Media, in front of students generations younger than me, it would force me to relearn my business each semester and hear directly from “the kids” themselves about what was “cool” to them, now. My classroom is a training ground - for them and for me. It is more than a generational focus group, it’s a reverse-mentoring cross-fit for my brain.

While I worked in corporate Media, in bigger gigs with more responsibility, I always maintained a 100% open-door policy, for any and all team members, at any and all levels. Often, this was a point of consternation for Gen X execs on my team, who were subjected to ideas I got directly from junior staff, and who became upset by a disruption of the “chain of command.”

In 2007, Cablevision instituted health benefits for same-sex partners, because a gay junior member of my team asked me why I hadn’t previously done anything to change the policy. Embarrassed, I urged senior management for the change and, to their credit, they made it. Many of the most important things I’ve ever done, and some of the most valuable relationships I’ve ever had, grew from collisions I curated with those younger and supposedly “less experienced” than me.

There is no question that I am a better professional and a better person for having gone beyond my comfort zone to understand younger generations. Today, I speak with many people my age who feel uncomfortable, even afraid, speaking to Millennials and Gen Z, for fear of saying “the wrong thing,” or worse, because the elders don’t feel that “young people today really understand how the world works.” In reality, I have found, it’s often the opposite.

Conversely, my ongoing conversations with 18-22 year olds in my class, and 23-35 year olds IRL, has taught me a lot about the challenges and complications younger generations face, entering into and succeeding in the modern Media workforce. The three generations under 45 have been trained to extremely overthink every decision they make and action they take, for fear of choosing a wrong move that will pigeonhole them or ruin their careers, forever. Social Media has exacerbated this mindset, with the world around us pretending to live their best lives, engendering an epidemic of decision paralysis. The pressure to succeed, from parents and society, is so great, and sets the bar so high, that many young people ask themselves what’s the point of even trying, if they’ll only fall publicly short. Then they see the epic shit-show produced by older generations - in the Media business and the world at large - and the conviction “that nothing they do matters anyway” calcifies, especially when they get accused of being “entitled” by their seniors, just for raising their hands to ask “why do we do things this way?”

There are now four generations sharing the American workplace. By decade’s end, that will grow to five, including Generation A. The issue is, despite more than $250 billion spent by Americans each year on higher education, no one is teaching those four generations how to relate, or even speak, to each other.

Yet, regardless of which generation you were born into, if you work in Media or Tech right now, we are all dealing with the same challenges - we all face the same existential crisis. The Knowledge Worker Economy has peaked, the industries we have chosen are spiraling, the “solid” career paths we picked years ago are eroding, and the businesses we thought would employ us forever continually prove just how few shits they actually give about any of us.

In the last two years, Media has shed 5X more jobs than in the previous two - and 2025 has started with substantial job losses across Media and Tech: At NBCU, Meta, Microsoft, Paramount, The LA Times, The Washington Post, VOX, Disney, Lionsgate, Disco Bros, Allen Media Group, and beyond. Recent and pending mergers or acquisitions, along with an economy teetering on recession, will almost certainly result in thousands of more job cuts in these industries. Even worse, with workers being slashed from America’s largest employer - the US Government - competition for open Knowledge Worker gigs will be steeper than any point in recent memory.

So, what’s an anxious Knowledge Worker to do? How does a brand new or early career professional navigate an economy where young college grads have twice the unemployment of the national average? What does a mid-stage career exec do, when it becomes clear there’s no path forward at their current company? How does someone currently dissatisfied with their gig manage to make a change when chaos is the new normal?

I have written extensively about this and, specifically, about my own experiences: How I was fired, thought it was the end of my career, then pivoted, and reinvented. But today, I want to offer case studies from others, who do not share my specific background or generation. As mentioned above, I have spent decades building relationships with those younger and different than me. I am proud to have maintained and nurtured these relationships over the years, continuing the mutual mentorships we established when we first met.

This week, on The Media Odyssey Podcast, I interview two such talented, brilliant, and generous members of our community. Katrina Craigwell was a PR coordinator when I first met her at IFC, nearly twenty years ago. Since, she has gone on to work at Meta, GE, and is now Head of Product at Chase. Jazz Pitcairn was a student in my NYU class six years ago. She since became the first and second person from her country (The Cayman Islands) to write for major American TV series - Apple’s Dickenson and HBO’s A Black Lady Sketch Show. This fall, she enrolls at University of Cambridge for a Masters in International Relations, so she can continue to use her content to push for social change.

Here is a clip of our conversations…

Katrina’s path has been truly remarkable. It’s been powered by her constant drive to learn and grow everywhere she goes, and by the rigorous discipline she applies to growing and maintaining her vibrant network - constantly reaching out to connect and reconnect with folks who can teach her new things and to whom she always offers value in return.

Jazz came to this country with no network. She is proof-positive that talent and truly hard work, when applied conscientiously, can compete with the Nepo-Baby industrial complex that tends to dominate the entertainment business.

Every time I talk to either of them, I learn something new. I hope you take the time to listen to or watch our full conversations on the pod, because even if you are satisfied with your current gig; their experiences prove that waking up stupid each day and continuing to learn about the things you care about most, is the best way to future proof your career.

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Enjoy the pod and enjoy your week.

ESHAP