AI is Changing EVERYTHING The Future of Work

Hi everyone, I'm excited to kick off this edition of AI Insiders by AI Marketer Guild with a special guest I've known for quite some time and have had the pleasure of learning from during my time at a Publicis Group agency. Rashad Tobaccowala spent a significant tenure there, ultimately serving as Chief Strategy Officer. Whenever he visited New York or I went to Chicago, I always enjoyed our conversations.

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Rashad, I don’t think I ever confessed this, but when you once offered me a ride to the airport, I actually adjusted my flight time so you wouldn’t think I was waiting around for hours. I just wanted the chance to catch up with you one-on-one; it was too valuable an opportunity to pass up. So, my apologies for that little white lie.

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Rashad, I’ve truly enjoyed your book and took quite a few notes. We have a great community here interested in the intersection of AI and marketing, and how AI is impacting the future of work. You've written and thought extensively about these topics, and I’m very interested in your perspective. I also come at this from a few different roles, as I'm currently engaged in various types of work—some of which I never expected to be doing five, ten, or fifteen years ago. I’m part of a fractional executive network, and I feel we’re in a transitional period where many people, by choice or necessity, are taking on multiple jobs or fractional work. The market demand and organizational structures haven’t fully caught up with this shift. I’d love to hear your take on where we are today.

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Thank you, David, and thanks to everyone attending. I recognize quite a few names in the audience, so hello to all. Let me set the stage with some broad themes from my book, which will help answer your question. The book is based on the premise that work is central to human existence. There are three main drivers of happiness: physical and mental health, the quality of relationships, and meaningful, purposeful, and rewarding work. Having meaningful work not only adds years to your life but also improves your relationships. 

I believe that between 2019 and 2029, work will change more than it did in the previous fifty years, creating both significant opportunities and challenges—many of which are being overlooked in favor of debates like “return to office,” which is largely a distraction from the real issues.

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My book identifies five primary reasons work is changing: advances in technology and AI, the rise of marketplaces like Shopify, Etsy, and AWS, the growth of side hustles—this year as many people will receive a 1099 as a W2 in the US—and major demographic and societal changes. For instance, COVID’s biggest impact wasn’t where people work, but why and for whom they work. We are entering an age where people are less interested in returning to their bosses, not just their offices.

Other major shifts include an aging population—the only growing demographic in the US is over 50 years old—and the risk of declining populations if immigration is restricted, as the US birthrate is below replacement level. There are now four or five generations with very different mindsets working together. For example, 66% of Baby Boomers believe in capitalism, compared to 22% of Gen Z. Seventy-six percent of Gen Z want to work for themselves, and 67% of Gen Z with full-time jobs also have side gigs. Yet we’re still fixated on “return to office” debates, which shows a lack of imagination and leadership.

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Twelve CEOs read my book while I was writing it, and after five chapters, they realized no one had clearly laid out these issues for them before. My argument is that it’s about what leaders choose to pay attention to.

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Now, regarding what companies and individuals should do: Most organizations currently have three types of workers—full-time employees, contractors, and freelancers. In tech, companies like Google and Meta already have more contract workers than direct employees. I believe we need a new category: the fractional employee. 

A fractional employee has all the benefits of a traditional employee but works, for example, 60% or 80% of the time and is paid accordingly—except for healthcare, which is provided in full. This approach is essential for three reasons: aging populations may want to continue working but not full-time; people at different life stages may need more flexibility; and, importantly, AI will reduce the demand for full-time staff, even though no one is talking about it. Companies could reduce headcount by 10-20% through fractional arrangements instead of layoffs, providing flexibility without the emotional or financial costs of severance.

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Another significant shift is in leadership. We’re experiencing a crisis of leadership. Many bosses operate from a zone of control—managing, overseeing, monitoring—whereas true leaders operate from a zone of influence—creating, mentoring, building, and inspiring. Today’s environment requires more of the latter.

For everyone, regardless of position, the future is about operating as a “company of one.” This doesn’t mean working alone but rather taking ownership of your craft, building your reputation, and collaborating with integrity. The entertainment industry already functions this way, with talent coming together for specific projects.

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Looking ahead, I’ll make an intentionally provocative statement: In the future, there will be fewer traditional jobs, possibly none, but plenty of work to be done. The music industry is a good analogy. Once, you had to go somewhere to hear music; now, everything is fractionalized, with songs available on demand from the cloud. Work will similarly become project-based, with talent assembled as needed—a trend already seen in consulting and entertainment.

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As companies adapt, there’s growing interest in roles that offer 60-80% employment with benefits. Many mid- and senior-level professionals are seeking such arrangements but find the market hasn’t fully adjusted. 

My advice: Start from your current position and gradually diversify your work, communicating transparently with your organization. Over time, transition from full-time to fractional roles. Alternatively, if you’re already consulting or advising, combine multiple roles to suit your skills and preferences. Make yourself accessible and easy to engage—offer initial work at low commitment or even free to demonstrate your value.

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One challenge in the US is healthcare, which is a significant consideration for anyone pursuing flexible work arrangements. Regarding career management in the age of AI, I view AI as a slingshot—an equalizer, not an advantage for big companies. Everyone will have access to AI, just like everyone has electricity. Companies need to rethink their entire strategies, not just create “AI strategies.” The key is to operate as a company of one, leveraging technology and continuously honing your skills.

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For example, recently, I had to deliver a presentation on AI and retail with little notice. Using AI tools, I assembled a 35-page deck in 20 minutes, even though I wasn’t an expert in the field. AI allowed me to quickly research, create, and add value, showing that scale is increasingly a disadvantage—unless you’re a company like Nvidia or Walmart.

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The question many are facing is how to make AI work for us, rather than against us. I write a free Substack every Sunday, and one of my most popular pieces discusses AI, humans, and the future of work. My main points: AI is still underhyped, and most people don’t realize its potential. Just as computation made calculations cheap and the internet made information cheap, AI will make knowledge cheap. However, intuition, insight, and creativity remain distinctly human.

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Companies are focusing on efficiency and effectiveness through AI, rapidly reducing the need for certain roles, especially in creative industries. However, the real transformation lies in existential opportunities and risks. Digital disruption didn’t just make the New York Times print faster—it fundamentally changed their business model. Similarly, AI demands a complete rethinking of business, not just optimization of existing processes.

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There will soon be billion-dollar companies with fewer than 100—or even 10—employees, as shown in my book and in discussions with Google. AI is an extraordinary opportunity for those willing to adapt, but also a significant threat to those who cling to outdated knowledge or models.

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AI is best described as an alien life form—neither machine nor human, but something entirely new. It continues to evolve rapidly, and interacting with it can feel like interacting with a living being.

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Let’s take some questions from the community. One question is: How does the concept of being a “company of one” work in upper management, where collaboration is important? And can AI be used to enable “debossification”?

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Being a company of one doesn’t mean working alone; it means having a clear skill set, a strong reputation, and being highly collaborative. In management, your deliverables must be clear—management itself isn’t a deliverable, especially as machines become better at certain management tasks. As for debossification, AI accelerates the process by making knowledge and access less dependent on traditional hierarchy.

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The traditional sources of a boss’s power—knowledge, access, and the ability to hire or fire—are becoming less relevant. Expertise is more valuable than experience, and AI can quickly level the playing field when it comes to information and access. The only real remaining authority is the power to terminate employment, but employees have increasing options.

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There are questions about early-career workers and where future talent will come from if AI takes over entry-level tasks. Some worry that graduates won’t be able to “get their foot in the door.” It’s true that Gen Z is finding it harder to secure jobs, but much of traditional entry-level work was busywork that should be automated. Instead, early-career workers can now take on more meaningful tasks, build skills quickly, and launch projects independently.

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It’s important to distinguish between bringing people back to the office and fostering meaningful in-person interaction. Many activities attributed to the office—creative brainstorming, relationship-building, and learning—often took place elsewhere. Companies should design intentional opportunities for interaction, rather than simply mandating office attendance.

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Regarding marketing and AI: Many marketing roles are being automated, but instead of searching for “safe” areas, focus on building core skills. I call these the “six Cs.” Change is difficult, especially for those established in their fields, but irrelevance is worse. To adapt, create a strategy for future growth, upgrade your skills, and be proactive about reorganization or transitions.

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The six Cs for future success are: cognition (continuous learning), creativity (connecting ideas in new ways), curiosity (asking why and what if), collaboration (working with integrity and trust), convincing (storytelling and selling ideas), and communication (writing and speaking effectively). In the past, people were told to learn coding or Mandarin; today, writing and presentation skills are more important. Even when I used AI tools to help with my latest book, my own answers were better because they reflected a unique point of view and clear action plan—something AI still struggles with.

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I’ve put together a resource page with my best writing on these topics, all available for free.

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When asked which companies are getting it right, I emphasize focusing on positive examples. There are many companies continually reinventing themselves—Microsoft, Delta Airlines (which invested in employees and service rather than cutting costs), and Domino’s Pizza (which completely transformed its business). The most talented people will gravitate to organizations where they feel inspired and can grow.

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In the future, success will come from combining AI with “HI”—not just human intelligence, but human intuition, insight, ingenuity, imagination, and inspiration. Those who refuse to use AI will find themselves increasingly marginalized, just as those who refused to switch from typewriters to word processors.

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Addressing workplace culture, especially “masculine energy” and resistance to diversity, equity, and inclusion: True leadership is rooted in principles, not just profit. Companies that ignore DEI are losing the next generation of talent. I advocate for thinking like an immigrant—embracing outsider perspectives, underdog determination, and inclusivity—as a more effective approach than traditional notions of “hardcore” leadership.

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In closing, thank you for spending time with us today. Continue to educate yourself and remain optimistic about the future. Despite headlines to the contrary, it’s a better time to be alive today in nearly every aspect. Feed your mind with quality content, not just what algorithms serve you. 

If you’re interested, my book is available, and you can reach me at rashad@gmail.com.