Rethinking Work by Rishad Tobaccowala – A Comprehensive Guide to the Work Revolution

Rishad Tobaccowala's book about rethinking work was recommended by a good friend, and while I was reading it, I constantly agreed with this author, who was reading my mind. Because he presents a compelling analysis of the transformations redefining the modern workplace, based on five major forces: generational shifts, technological advancements, digital marketplaces, new work structures, and the lasting impact of COVID-19. 

I absolutely loved the book Rethinking Work, and as he does, I also highly recommend any content of Josh Bersin, called by Tobaccowala a talent legend. 

So here goes his top 5 forces, reshaping work:

1. Tobaccowala begins by exploring generational shifts, emphasizing that, for the first time in history, four or even five generations are working alongside one another. This generational mix creates both friction and opportunity, as younger workers bring digital fluency and a redefined sense of purpose, while older workers offer deep expertise and institutional knowledge. The author also underscores how ageing populations and declining birth rates in many countries are reshaping workforce dynamics, forcing organizations to reconsider traditional retirement models and integrate experienced professionals into evolving work structures.
2. The second major force is technology, particularly artificial intelligence (AI) and automation. Tobaccowala presents a provocative argument: as AI continues to reduce the cost of knowledge to nearly zero, every job—especially in high-income countries—will be affected. While some roles will disappear, others will be redefined, requiring a shift in skills and workplace expectations. The challenge for organizations, he argues, will not simply be integrating AI but leveraging human strengths—creativity, problem-solving, and emotional intelligence—alongside it.
3. Next, Tobaccowala examines the rise of digital marketplaces, such as Upwork, Etsy, and Shopify, which have empowered individuals to monetize their skills and access global markets with unprecedented ease. He sees this trend as a game-changer, enabling freelancers and small businesses to scale in ways once reserved for large corporations. This shift contributes to the growing “unbundling” of work, where talent is no longer confined by traditional employment models but instead flows dynamically across multiple projects and organizations.
4. A fourth force—the restructuring of work itself—is reshaping how people engage with employment. The author highlights the growing trend of fractionalized employment, where individuals juggle multiple roles, whether through side gigs, part-time jobs, or entrepreneurial ventures. Rather than relying on a single employer for financial stability, many workers are now assembling a “portfolio” of jobs that better aligns with their skills, interests, and personal needs.
5. Finally, Tobaccowala reflects on the long-term impact of COVID-19, arguing that the pandemic was not just a short-term disruptor but a catalyst for permanent change. Beyond remote work, he contends that COVID-19 rewired the way people think about employment, leading to heightened expectations around flexibility, well-being, and purpose. He suggests that organizations failing to recognize this shift risk losing talent to more adaptable and progressive employers.

Then talking about the future of organizations, Tobaccowala opts for a metaphor that got me from the very first second: from classical to jazz. 

One of the book’s most memorable metaphors is Tobaccowala’s comparison of past and future organizational structures to musical genres. Traditionally, companies have operated like classical orchestras—rigid, hierarchical, and highly structured, with a conductor ensuring each section follows a meticulously planned score. 

In contrast, the workplace of the future, he argues, will resemble jazz ensembles, where different players collaborate in more fluid and unpredictable ways, improvising as circumstances evolve. Companies will become more adaptable, forming and reforming themselves in response to market shifts, technological advancements, and workforce expectations. 

This shift also has significant implications for leadership. Tobaccowala envisions a new breed of leader who thrives in ambiguity, embraces a growth mindset, and prioritizes continuous learning over rigid control. Rather than traditional managers who monitor and delegate, future leaders must serve as facilitators and mentors, supporting employees in their professional development while allowing for greater autonomy.

Work flexibility and the rise of the individual

A particularly striking theme in Rethinking Work is the increasing power of the individual in shaping their own work experience. Tobaccowala argues that employees are no longer content to be passive participants in a rigid system; instead, they are demanding flexibility in where, when, and how they work. 

He notes that, in many cases, workers aren’t leaving employment altogether but are instead rejecting outdated workplace cultures and ineffective management structures. He discusses the freelance revolution, highlighting a significant trend: by 2027, nearly half of the workforce will be freelancers. 

This shift necessitates a reevaluation of corporate policies, as organizations must adapt to a world where full-time employment is no longer the dominant model. Businesses that fail to accommodate flexible work arrangements risk alienating both younger and experienced professionals who seek greater autonomy over their careers.

Challenges and opportunities in a multigenerational workforce

One of the book’s most insightful discussions revolves around the tensions and opportunities presented by a multigenerational workforce. Tobaccowala highlights stark differences in values and expectations between baby boomers and millennials, particularly regarding authority, success, and worldview. While baby boomers often define success through financial achievement and hierarchical advancement, millennials prioritize work-life balance, purpose-driven careers, and inclusive workplace cultures.

This generational divide, if not properly managed, can lead to conflict and disengagement. However, the author sees an opportunity for organizations to foster intergenerational collaboration, leveraging the strengths of each group. He proposes designing workplaces that accommodate different working styles—whether through varied office layouts, diverse communication methods, or tailored career paths for employees at different life stages.

The role of AI and human-centric work

A recurring theme throughout the book is the intersection of technology and human work. While AI and automation will undoubtedly reshape industries, Tobaccowala emphasizes that human qualities—such as empathy, creativity, and leadership—will remain irreplaceable. He warns against blindly automating processes without considering the psychological and social impact on employees. 

Instead, he advocates for a cautious embrace of AI, ensuring that technological advancements enhance rather than erode workplace culture. He also stresses the need for organizations to invest in learning and development, particularly as technological shifts shorten the half-life of knowledge. Companies must become continuous learning ecosystems, where employees are encouraged to upskill and adapt in response to emerging trends.

Rethinking Work is more than just a theoretical exploration of workplace trends—it’s a practical guide for navigating the evolving world of work. Tobaccowala offers actionable insights for both employees and employers, urging individuals to proactively shape their careers and encouraging businesses to embrace flexibility, transparency, and lifelong learning. 

For HR professionals, business leaders, and policymakers, the book provides a roadmap for designing work structures that align with modern realities. And for workers at all levels, it serves as an empowering call to action: the future of work is not something to be feared but an opportunity to redefine career paths on our own terms.

About Rishad Tobaccowala

Rishad Tobaccowala is a business strategist, author, and advisor known for his expertise in marketing, digital transformation, and organizational change. He spent over 30 years at Publicis Groupe, where he held leadership roles such as Chief Growth Officer and Chief Strategy Officer. 

He is the author of Restoring the Soul of Business: Staying Human in the Age of Data, which explores how companies can balance data-driven decision-making with human insight.