Uphoff on Media | Field-Tested Frameworks
A few years ago, I started getting calls from young people in their junior year of college. Friends of our daughter, classmates, people looking for a perspective on what to do next. I was glad to take them. I’ve been in and around B2B media, marketing, and technology for more than 35 years. If I could save someone a few wrong turns, I was happy to help.
One of those conversations has stayed with me. A young woman — a high school valedictorian, Ivy League junior, internships at Google and NBC, job offers from both — reached out for some perspective. She was leaning toward NBC. When I asked why, she said her parents felt it was the safer choice. They knew NBC. It was familiar. Recognizable.
I told her: “You’ll do well no matter where you go. What this really comes down to is whether you want to be part of the past or the future.”
She thought about it. Then she went into consulting.
I’ve thought about that outcome more than she probably has. She didn’t choose the past or the future. She chose optionality. She intuitively understood something that took me years to be able to articulate: the institution itself was the risk. At 21, without having read a single business book about it, she made an infinite game move.
That instinct is rarer than it should be. And in 2026, the cost of not having it has never been higher.
The numbers are not ambiguous
Let’s start with the data, because this post is not about feelings. It’s about facts, and the facts in B2B media, marketing, and technology are stark.
* 17,000+ entertainment and media jobs cut in 2025: An increase of 18% from the year before
(Challenger, Gray & Christmas)
* 54,000 advertising, PR, and related services jobs lost in a single year through May 2025
(Bureau of Labor Statistics)
* 14,298 average annual media job cuts since 2018: Nearly double the 7,305 annual average from 2010–2017
* Informa TechTarget, formed in December 2024 with 2,000 employees, had shed roughly 500 of them by October 2025.
On the agency side, the story is the same. Forrester analysis puts agency headcount down 8% in 2025. The Omnicom-IPG merger alone is expected to generate $750 million in cost savings, and labor costs always lead the balance sheet. WPP, Dentsu, IPG: thousands of roles gone, with more to follow.
The jobs disappearing fastest are the ones that taught the craft. Junior copywriter. Media planner. Demand gen coordinator. Research analyst. The entry-level roles that once served as the apprenticeship layer of this industry; where you learned how audiences work, how campaigns are built, how buyers actually behave, are being automated out of existence first. Anthropic’s own research shows hiring of younger workers has slowed roughly 14% in the most AI-exposed occupations compared to 2022.
If you are early in your career in this industry, or advising someone who is, this is not a cycle. It is a structural shift. The map you were handed is of a city that no longer exists.
A book changed how I think about all of this
I read Simon Sinek’s “The Infinite Game” in 2019. To this day, no single book has more fundamentally shaped — and reshaped — my philosophy about work and career. The thesis hit me hard.
We have been brought up in business to apply finite game theory to infinite games. Finite games have a fixed endpoint, agreed-upon rules, and a winner. Infinite games have no finish line. The only goal is to keep playing.
Careers are infinite games. We have been playing them like finite ones.
The ultimate goal of the career game is to keep on playing. Not win a single position, title, or business deal.
“The Infinite Game” became my most gifted book for the next three years. I revisit it often. Because every time I look at the career decisions I’ve watched people make — and the ones I’ve made myself — I see the same pattern. Someone optimizing to win the quarter, land the title, close the deal. And in doing so, weakening their position in the game that actually matters.
The valedictorian who went into consulting wasn’t running from a decision. She was, instinctively, playing the longer game. The parents who steered toward NBC were giving advice from inside their own era. Advice that was entirely correct for a media landscape that no longer exists. That’s not a failure of love or intelligence. It’s what happens when you use last decade’s map to navigate this decade’s terrain.
What a career in this industry actually is
Thirty-five years. Five CEO roles. This is the framing that has held up through all of it:
A career in B2B media, marketing, and technology is not a series of jobs. It is a continuously developed capability to understand how buyers find, trust, and act on information, and to create value at that intersection across media, marketing, and technology.
That’s it. Everything else: the titles, the companies, the platforms, the tech stacks, is scaffolding. The scaffolding changes. The function doesn’t.
The companies that collapsed in this industry were the ones that forgot what function they actually served. They started optimizing for the advertiser or the algorithm instead of the buyer. The careers that stalled were the ones that attached too tightly to a form; a specific medium, a specific platform, a specific role, rather than the underlying function.
Agentic AI is not changing the function. It is reorganizing everything around it. The question for anyone building a career in this industry right now is not: “Will my job exist?” It is: “Am I building toward the function or toward the form?”
A framework for three stages
The infinite game plays out differently depending on where you are in it. Here is how I think about it across three stages. Use them as a mirror, not as a map
Stage 1 · Years 0–10
Get close to the work
The goal is not the credential. It is closeness to the actual work of understanding buyers, building audiences, and creating demand.
The danger at this stage is chasing the brand-name employer, the prestigious title, the defined role, at exactly the moment those institutions are most unstable. Get as close as possible to the actual work. Learn the underlying physics. Not the specific machine.
Diagnostic questions:
1. Can you describe, in plain language, how a B2B buyer actually makes a purchase decision…not in theory, but in the specific market you work in?
2. If your current employer disappeared tomorrow, what capability would you carry out the door, and how would you describe it to the next person?
3. Are you learning from people doing the work, or from people managing those who do?
* The honest answer is the former. Managers teach you how the institution works. Practitioners teach you how the work works. Only one of those travels with you.
4. Is your current role building a skill, or executing a process someone else designed?
5. When did you last do something at work that made you uncomfortable because you weren’t sure you could do it?
Drift signal: You are optimizing for the brand name on your resume rather than what you are learning inside the building. The institution feels like the asset. It isn’t. What you can do when you leave is the asset.
Stage 2 · Years 10–20
Build something portable
The goal is not the next title. It is a reputation, a network, and a point of view that exist independently of any single institution.
This is where Sinek’s insight lands hardest. Mid-career professionals in B2B media, marketing and technology have usually been playing a finite game, competing for the next title, the next company, the next comp band. The infinite reframe asks: what are you building that compounds?
Diagnostic questions:
1. If someone in your industry were asked about you by name, what would they say you are known for? Not your title, not your company, but you?
2. In the last 12 months, have you built any relationships that exist outside your current employer’s org chart?
3. Do you have a point of view about your industry that you could defend in a room full of smart people who disagree with you?
4. If your company restructured tomorrow and your role disappeared, how long would it take you to land your next opportunity, and what would that process look like?
5. Are the decisions you are making now — projects, relationships, visibility — compounding, or are they just getting you through the quarter?
Drift signal: Every career move for the past five years has been toward a better title or higher comp, with no conscious thought about whether it built something portable. The ladder is the strategy. It isn’t enough.
Stage 3 · Years 20+
Recognize what you actually have
The goal is not survival. It is accurate inventory. Most senior operators in this industry underestimate the scarcity of what they have built.
Late-career operators in B2B media, marketing, and technology have something genuinely scarce: they understand how buyers actually behave, how deals actually get made, how organizations actually change. Not in theory, but from having been inside the room when it happened. Agentic AI can automate the process of demand generation. It cannot replicate the judgment about which markets matter, and why, and when.
Diagnostic questions:
1. What do you know about how buyers, markets, or organizations actually behave that cannot be found in a report, a course, or an AI prompt?
2. Who calls you when they have a hard decision to make, and why do they call you instead of someone else?
3. Are you framing your experience in terms the next generation of decision-makers can understand and act on, or in terms that only made sense in the media and marketing economy of 15 years ago?
4. What would you build, advise, or create if you optimized for the next 10 years of the game rather than the next role?
5. Are you giving advice from who you are now, or from who you were when you were most successful?
Drift signal: You are describing your experience in terms of institutions and titles rather than judgment and outcomes. The instinct is to protect the identity you built. The opportunity is to deploy what is behind it.
The framework above is also available as a standalone reference. Download or save this for reference, and share it with someone who needs the framework.
The real question isn’t about AI
Every version of this conversation eventually arrives at AI. And the conventional answer is always the same: learn to use it, stay adaptable, embrace change. That advice is true and useless in equal measure.
The more interesting question is the one the valedictorian answered without knowing she was answering it. Not: “What tool do I need to learn?” But: “What am I building that is valuable with or without any institution behind it?”
In B2B media, marketing, and technology, the answer to that question has been the same for decades, even as every platform and format around it has changed. The buyers are out there. They need to find solutions they can trust. Someone has to build the bridge. The function has always been to be part of that bridge; credibly, durably, in a way that compounds over time.
The response to my last piece made clear that the economic pressure is real and widely felt.
The question I keep getting, in various forms, is the same: “Given all of this, what do I do with my career?” This is my best current answer.
A career in B2B media, marketing, and technology is not a series of jobs. It is a continuously developed capability to understand how buyers find, trust, and act on information — and to create value at that intersection. The function has been the same for decades. The scaffolding around it; the titles, the platforms, the institutions, the tech stacks, has changed repeatedly, and is changing again now, faster than at any point in my career.
The map has changed. The territory hasn’t.
Play the infinite game.
One question I'll leave you with — and one I'd genuinely like to hear your answer to: which stage of this framework are you in, and are you building toward the function or toward the form?
Keep going: Twenty Years of Transformation, and We’re Just Getting Started and Three Ways to Lead Through AI Disruption. One Way to Fail
The views expressed in Uphoff on Media are entirely my own. They don’t represent the opinions of any company I’ve led, any board I’ve sat on, or any investor who’s had the pleasure of debating strategy with me over the years. If something I write here sounds brilliant, I’ll take full credit. If it turns out to be wrong, I was clearly misquoted by myself.
“Uphoff on Media” is published by Tony Uphoff, Founder and Managing Partner of Uphoff Advisory, a strategic advisory practice for founders, CEOs, and investors in B2B information, marketing, and technology. The businesses that drive business.
