Work Backwards

Work Backwards Plot Summary

Introduction

The hospital room was quiet except for the rhythmic beeping of monitors. Tim sat beside his father's bed, holding his hand as the hours passed. In these final, delicate moments, all the unimportant trivialities, unfinished jobs, and never-ending to-do lists melted away. What remained was crystal clear: relationships mattered most. The promotions, late-night emails, corner offices, and pay rises wouldn't mean anything when you're on your deathbed, holding the hands of loved ones as you breathe your final breath. This profound realization sparked a journey to uncover a revolutionary way to approach work and life. For decades, we've been taught that success means climbing the corporate ladder, working longer hours, and sacrificing everything else along the way. But this approach is breaking us. People everywhere are overworked, disengaged, and apprehensive about the future. The answer isn't working harder but working backwards—starting with the life we want to live, then determining how much money we need to support that life, and only then figuring out how work fits into the picture. This paradigm shift doesn't mean being lazy or not working hard; it means being intentional about aligning your work with your priorities, using new tools and frameworks to craft a life of meaning and fulfillment rather than exhaustion and regret.

Chapter 1: The Breaking Point: When Work Consumes Everything

Geoff McDonald had reached the pinnacle of corporate success. As Global Vice President of HR for Unilever, he oversaw 170,000 employees across 90 countries. It was the culmination of a 25-year career that had taken him from teaching in South Africa to the executive suite of one of the world's largest consumer goods companies. His job was intense, busy, and high-pressure—everything a successful career was supposed to be. Then came January 26, 2008—his daughter's thirteenth birthday. Geoff awoke in the grip of a massive panic attack, an experience unlike anything he'd felt before. His first thought was that he was having a heart attack. When his daughter bounded into his room at sunrise, he mustered whatever energy he had left to quietly beg his wife to take her and her sister downstairs. Hours later, still unable to get out of bed, his wife convinced him to see a doctor, where he was officially diagnosed with anxiety-fueled depression. "I'm not very good at masking my feelings or trying to be somebody that I'm not," Geoff explained. "You just need to look me in the eye and you'll see if there's something going on." His line manager responded with compassion rather than judgment. "He didn't judge me for the fact that I was sick with depression. In fact, he loved me and supported me through my illness." After recovering, Geoff eventually left Unilever to pursue a newly discovered purpose: creating workplaces, friendship groups, and families where everyone feels they genuinely have the choice to ask for help if they are struggling with mental health issues. Now, when Geoff visits organizations, the number one issue people want to discuss is the pressure they feel to work more. "Everybody is talking about workload," he says. This phenomenon isn't limited to office workers. From nurses to teachers, postal workers to waitstaff, the breaking point is approaching across all industries. In 2023, renowned chef René Redzepi announced he was closing his highly awarded restaurant, Noma, because the grueling hours required by chefs and hospitality workers were unsustainable. "We have to completely rethink the industry," he said. "This is simply too hard, and we have to work in a different way." When work consumes everything, something has to give—and that something is usually us. Our bodies and minds can only withstand so much pressure before they begin to crack. The feelings of being overworked, disengaged, and apprehensive about the future are warning signs that our current approach to work isn't sustainable. Yet too often, we ignore these signals until we reach a breaking point, forced to confront the reality that we've been living in the wrong direction all along.

Chapter 2: Creating Your MAP: Meaning, Anchors, and Priorities

For decades, Tiffany Farrington has enjoyed what she calls "bliss," carefully crafting a life where work complements her priorities rather than dominating them. It began in 2004 when she was planning a major event for Cartier. Tired of discovering that her competitors were hosting similar events on the same night, she emailed 25 public relations friends asking if any had events planned for the same date. Soon, other PR professionals were asking if they could message the same group to check dates for their events too. Trying to be helpful, Tiffany gathered upcoming event dates into a single Word document and emailed it to her contacts every Wednesday. "It's funny to look back at this time because it was never, ever meant to be a business," she says. "I was just trying to be helpful!" That helpful list evolved into Social Diary, now a successful subscription business providing a calendar to avoid clashing events, daily newsletters with media and celebrity contacts, editorial opportunities, and influencer information. During the early years, Tiffany worked hard to build the business, but always with flexibility at its core. "Back in my party days, my work and social life were completely merged and that was heaven to me in my twenties and thirties," she recalls. What made her approach different was her commitment to working from anywhere. "I've always liked a different view out my window while I do it," she says. "In 2009 I sent it from a yacht in the middle of the Caribbean, from a dance party in Barcelona at three am, from beach bars in Thailand and even from the only hotel in Cuba that had wi-fi, all whilst sipping on a Cuba Libre, naturally." She lived by the saying that "work expands to fit the time you have," adding, "I can assure you, when you have beaches and palm trees out your window, you get your work done very fast!" After living in big cities her whole life, in 2021 Tiffany moved to the country, settling in the picturesque wine-growing region of the Hunter Valley a couple of hours north of Sydney. "It's simply calmed me in a way I never thought possible as I've always been so fast-paced and used to running around like mad," she says. "I love this new slow pace of life." The flexibility she built into her business also allowed her to care for her parents when they became ill. "I'm so lucky I was able to be bedside around the clock for when my dad was dying. I didn't have to take leave or ask a boss—I just set my laptop up in the hospital, which was everything." Tiffany's story exemplifies the power of creating a MAP—understanding your Meaning, Anchors, and Priorities. This is the first step to working backwards. Rather than letting work dictate your life, you consciously design your life around what matters most to you. Meaning comes from identifying what fulfills you both inside and outside work. Anchors are your core values that define who you are. Priorities help you determine how to allocate your time across the four domains of work, relationships, mind, and body. When these elements align, you create a "full-circle life" where each aspect receives the attention it deserves, leading to greater satisfaction and wellbeing.

Chapter 3: Defining 'Enough': Breaking the Work-and-Spend Cycle

In Helsinki, on a sunny summer's day, philosopher Frank Martela sits in his office at Aalto University, surrounded by rows of books and neatly titled folders. One wall is dominated by an intricate hand-drawn map of a fictional world, created by his eight-year-old son. As an expert on the intersection between Finnish culture and happiness, Frank has unique insights into why Finland has been named the happiest country in the world for six consecutive years. What's remarkable is that most Finns were surprised by this designation. "There wasn't too much discussion about happiness rankings in Finland until the moment we were declared happiest country on Earth," says Frank. "Then suddenly everyone was asking what was the secret to Finnish happiness? And the Finnish people were like, 'We don't have a secret, we didn't know that we were happy.'" Frank explains that most Finns have "a bit of a melancholic self-image" and think of themselves as relatively introverted and quiet. The World Happiness Report measures life satisfaction rather than joyfulness or cheerfulness. Finland scores highly because there are very few people in the country who rate their life satisfaction in the low digits. "So it's rather the lack of unsatisfied people that explains the high average rather than the presence of extremely happy people," says Frank. In other words, Finns are not blindly optimistic happiness freaks with permanent smirks; they are merely content with what they have. This contentment stems from strong welfare systems, democratic institutions, and work-life balance—most Finns take the entire month of July off to enjoy summer. But perhaps the most important factor is their understanding of "enough." A study published in January 2023 by Arto O. Salonen and Jyrki Konkka found no happiness differences between Finns from different income groups. It didn't matter how much money they earned; everyone was relatively content with their lives. Finns feel satisfied leading relatively straightforward, sustainable lives, with enough money to meet their simple needs. "In other words," Salonen and Konkka concluded, "when you know what is enough, you are happy." This concept of "enough" stands in stark contrast to the work-and-spend cycle that dominates many cultures. Comedian Diane Morgan, playing journalist Philomena Cunk, describes this cycle perfectly: "They'd work hard to get money, to buy a car, so they could go to the shops and buy more things, which they'd have to pay for by going back to work, which made them miserable, so they'd cheer themselves up by going out and buying more things, which they'd have to work to pay for." Breaking this cycle requires creating what Charles Handy, a pioneering business thinker, calls a "Backwards Budget." Instead of letting your employer determine your salary and then building your life around that figure, you work out how much money you need to live a life that brings you fulfillment and design your work accordingly. This approach demystifies finances and helps align money with your values and priorities. Knowing your "enough" liberates you from the endless pursuit of more, allowing you to focus on what truly matters.

Chapter 4: The Tools Revolution: Flexible, Remote, and Hybrid Working

Kim McKay prides herself on being ahead of the curve. With a career spanning radio, music, travel, and communications, she has a knack for seeing around corners, adapting her working style to trends before they fully arrive. For years, Kim knew that everyone's productive hours were different. She was most creative late at night, so she'd sometimes start her day mid-morning and work unusual hours, always trying to shake her team out of the nine-to-five mentality. Occasionally, she'd book a meeting into everyone's diary, only to surprise them with tickets to a movie in the middle of the day. "I just wanted to prove that the world doesn't end if you step away for two hours," she says. "And when you go back, you're probably better." This approach to flexibility wasn't just theoretical—it was central to how she ran her digital-focused communications agency, Klick. In 2019, Kim "blew everything up" by completely rethinking how her business operated. She'd been desperately trying to hire a new staff member who couldn't join her team in Sydney because they were moving to Stockholm. Rather than settling for someone who could make it into the inner-city office every day, Kim moved her business to a hybrid workplace, giving up the lease on a large office and telling her staff they could come in whenever suited them. The results were fascinating. "No one came in on Monday ever," laughs Kim. "By Tuesday you could see they started to miss each other or wanted some face-to-face time. On Wednesday they'd be out at meetings and then on Thursday, Friday they'd pop in. It was really interesting just to watch, because we didn't force it, we said, 'If we want people to act like adults, let's treat them like that and see what happens.'" The biggest revelation was the change in thinking about the purpose of the office. "We realized that an office is the last place you go to do work. It's where you go to hang out, collaborate and communicate. Actual concentration never happens in open-plan offices." Kim now runs her business completely remotely, eschewing a traditional office for the ability to connect with a team of contractors around the world on a project-by-project basis. This tools revolution—encompassing remote, hybrid, and flexible working—represents a fundamental shift in how we approach work. Remote working allows employees to work primarily outside a typical workplace, giving them freedom to live where they choose and design their environment for optimal productivity. Hybrid working combines time in the office with time working elsewhere, typically home. Flexible working adjusts standard hours to accommodate individual needs and preferences. Each of these tools can be adapted to different industries, career stages, and personal circumstances. The key is to experiment, communicate clearly, and focus on outcomes rather than hours worked. As workplaces continue to evolve, these tools will become increasingly important for creating a sustainable and fulfilling relationship with work. The future of work isn't about one perfect solution that works for everyone, but about finding the right combination of tools that allows each person to thrive.

Chapter 5: Future-Proofing: Four-Day Weeks and Career Sabbaticals

Andrew Barnes never expected to change the world. As the founder of Perpetual Guardian, a New Zealand legal services company, he simply wanted to test a hypothesis about productivity. What would happen if he mandated that his 240 employees work 20% less? "When I announced it in my own company, there was nobody in my leadership team, no board member, who supported it," he says. "The only reason it got through is because I was the principal shareholder in the company!" After two months of experimentation, the results were striking. Seventy-eight percent of employees said they were able to successfully manage their life-work balance, compared to 54% the previous year. Their self-reported stress levels decreased by 7%, and overall life satisfaction grew by 5%. Andrew announced the results to the world, making the four-day workweek permanent. The media response was overwhelming—they stopped counting at about 13,000 global news stories. "I didn't expect that this little experiment would get such a global reaction," says Andrew, "and the fact it did says I think we're ready for a rethink of how we work." Since then, Andrew and his partner, Charlotte Lockhart, have coordinated thousands of tests in companies around the world, from Canada to Belgium, America to Romania. Results from nearly 3,000 UK workers who completed 12 months of working four-day weeks concluded that more than 90% of the companies would continue it, mainly due to benefits like a 71% reduction in employee burnout levels and a 43% improvement in mental health. Other studies found benefits such as less stress, better sleep, and more time to invest in other areas of life. Career sabbaticals represent another powerful tool for future-proofing your working life. Taking extended periods off work allows you to properly rest and renew before tackling the next chapter. Data from the Society for Human Resource Management shows that the number of people taking large chunks of time out of their career tripled from 2018 to 2022, much of it driven by a reassessment of priorities during the pandemic. These breaks challenge the traditional linear career path of learn-earn-burn: learn (education until your twenties), earn (non-stop work until retirement), and burn (spend savings during retirement). Instead, they allow you to insert multiple "finish lines" throughout your career, creating opportunities to travel, learn new skills, raise a family, or pursue creative projects. Each finish line provides a chance to stop, celebrate achievements, recuperate, and reassess priorities before beginning the next stage. Researchers have identified three types of sabbaticals: working holidays (combining some work with time off), free dives (completely changing direction as a jolting change), and quests (seeking something spiritually higher). Regardless of type, the benefits are consistent: increased well-being, renewed purpose, and fresh perspectives. Taking time to step back from the treadmill of life allows you to reconnect with what matters most and design the next chapter on your own terms. Together, four-day weeks and career sabbaticals represent powerful tools for creating a sustainable relationship with work throughout your entire career. They acknowledge that humans aren't machines—we need regular rest and renewal to perform at our best. By challenging traditional notions of what a successful career looks like, they open up possibilities for a more balanced, fulfilling, and long-lasting professional life.

Chapter 6: AI and Automation: Partners Not Replacements

In November 1980, Bill Gates attended a meeting that would shape the future of technology. Sitting with a brilliant young programmer named Charles Simonyi, Gates was shown a graphical user interface for computers—a breakthrough that would make computing accessible to everyone. This revelation gave Gates a clear vision of where technology was heading. Four decades later, in September 2022, Gates experienced that same feeling when he witnessed OpenAI's artificial intelligence system ace an Advanced Placement biology exam—a test requiring critical thinking, not just memorization. "I knew I had just seen the most important advance in technology since the graphical user interface," Gates wrote. "The development of AI is as fundamental as the creation of the microprocessor, the personal computer, the internet, and the mobile phone. It will change the way people work, learn, travel, get health care, and communicate with each other." Artificial intelligence is indeed transforming our relationship with work, but not necessarily in the dystopian ways often portrayed in media. Rather than replacing humans entirely, AI is increasingly becoming a collaborative partner that augments human capabilities. Take "Flippy," a robot created by Miso Robotics that prepares and fries food in restaurants, handling the dull, dirty, and dangerous tasks in professional kitchens. "He's in the back flipping the burgers and testing the oil of the French fries," explains Steven Hatfield, Global Leader for Future of Work at Deloitte. "He is enabling that workforce to either elevate up to just managing the robots, or to be up front dealing with the customers in a different way." This collaborative approach—sometimes called "cobots" (collaborative robots)—represents a more nuanced view of technology's role in the future of work. Instead of complete automation, humans and machines work together, each playing to their strengths. "The future of work is human," says Dr. Sean Gallagher from Swinburne University. "We shouldn't remove the human from the value-add processes because they have a lot of problem-solving skills." Healthcare provides another compelling example. "Fifty percent of a nurse's time in North America is spent doing things that have to deal with admin," says Hatfield. "So if we can digitize more and more of that, be that an AI tool or a robot, and free them up to go back to bedside care, that'll be a real boom to what ostensibly is already a looming shortage." The key to successfully navigating this technological shift is to view AI as a tool that can give us time back—time we can invest in the aspects of life that matter most. This requires a mindset shift away from fear and resistance toward curiosity and adaptation. Staying informed about developments, experimenting with different applications, and focusing on uniquely human skills like creativity, empathy, and complex problem-solving will help ensure that AI remains a partner rather than a replacement. Of course, anxiety about these changes is natural. A study by Advertising Week APAC found that 75% of Australians are worried about the impact of adopting AI at work, citing concerns about reduced creativity, diminished human judgment, increased surveillance, and growing dependency. Acknowledging these fears while actively exploring how AI can enhance rather than diminish our working lives is crucial for developing a healthy relationship with technology. By viewing AI as a partner rather than a threat, we can harness its potential to create more meaningful, fulfilling work experiences—ones that emphasize uniquely human contributions while automating routine tasks. The future of work isn't about humans versus machines; it's about finding the right balance that allows each to contribute what they do best.

Chapter 7: The Full-Circle Life: Balancing Work, Relationships, Mind and Body

Anna and Sam Luntley run a small bakery on the south side of Glasgow. Set on a quiet street corner surrounded by sandstone tenement houses, two.eight.seven. opened its doors in 2021. Outside the shop are garden beds bursting with seasonal herbs and vegetables, their edges doubling as seats for customers enjoying freshly made tarts, pastries, cookies, pies, and bread that changes each week depending on produce and the bakers' creativity. As art-school graduates who found they could express themselves better through food than art, Anna and Sam have been on a journey to perfect their relationship with work. Their current bakery is their third attempt at finding balance—and it's only now starting to feel right. Their first iteration grew from an artistic residency in the Scottish Highlands, where they baked obsessively in a woodland cottage for a week, distributing loaves to the local community. Back in Glasgow, they continued baking from their small apartment, gradually building a customer base until they could quit their full-time jobs. Each week they'd send out an email about their adventures and ideas, then spend the rest of the time baking in their home kitchen, sometimes sleeping only two hours a night to keep up with demand. "It was all-consuming," says Anna. "We did this for almost three years and there was no divide between work and life... We couldn't maintain this crazy and intense way of living and working. We were exhausted." For their second attempt, they moved into a shopfront and opened to the public Thursday through Sunday, while continuing to serve wholesale clients seven days a week, often working from 4 a.m. until midnight. Once again, work consumed everything. "We had gone too far down the business road and felt the need to step out, get out of the city, see the world, and refresh our inspiration and creativity," says Anna. After three years, they closed the shop and left town. After traveling and working sporadically for a few years, they returned to Glasgow determined to build a business that aligned with their values and priorities. They carefully considered their previous burnout experiences, their life goals, and how they wanted to work. Their first decision was to open the bakery to the public only on Saturday and Sunday. In a typical week, they take Monday and Tuesday off, spend Wednesday doing admin, and bake on Thursday and Friday. They also close the shop completely for one week roughly every eight weeks, take breaks at Christmas and Easter, and have a month off in summer. This schedule, which resembles an academic timetable with intense periods of work followed by regular rest, allows Anna and Sam to remain creatively fulfilled while maintaining space for friends, family, and recovery. They also decided to do everything themselves rather than hiring staff, recognizing their finite capacity and designing the business around it instead of constantly expanding. "We now run a bakery which, at least some of the time, feels like we control it rather than it controls us," says Anna. "There is a space between life and work when we want there to be." The Luntleys' journey illustrates the essence of a full-circle life—one where work, relationships, mind, and body all receive appropriate attention. Rather than prioritizing work at the expense of everything else, a full-circle life aims to distribute time and energy across these four core elements: Work: Ideally around 32 hours a week (four days), allowing for focused, productive effort without exhaustion. Relationships: Approximately four hours a day connecting with family, friends, colleagues, and community. Mind: About four hours daily for mental nourishment through hobbies, learning, reading, spiritual practices, or simply being. Body: Around four hours a day for physical wellbeing, including exercise, cooking healthy meals, rest, and self-care. These targets aren't rigid rules but aspirational guidelines. The magic happens when you combine activities across categories—like hiking with friends (body, relationships, and mind) or playing board games with family (relationships and mind). What matters is consciously designing your life around all four elements rather than letting work dominate by default. Creating a full-circle life isn't about perfect balance at every moment. There will always be periods when one area demands more attention, like the early years of parenthood or launching a business. The key is having a clear vision of what you're working toward—a life that honors all aspects of your humanity, not just your productivity.

Summary

Imagine lying on your deathbed, reflecting on your journey through life. Would you be thinking about the late-night emails you sent, the promotions you earned, or the extra hours you put in at the office? Or would your thoughts gravitate toward the relationships you nurtured, the moments of joy you experienced, and the meaning you created? If we're honest with ourselves, we know the answer—yet so many of us continue to live as though work is the central purpose of our existence. The Work Backwards framework offers a revolutionary alternative: start with the life you want, determine the money you need to support it, and then design your work accordingly. This three-step process—creating your MAP (Meaning, Anchors, Priorities), knowing your "enough," and using the right tools—provides a practical pathway to reclaiming your life in a world obsessed with work. It doesn't mean abandoning ambition or productivity; it means aligning them with what truly matters. Whether you're experimenting with remote work, trying a four-day week, taking a career sabbatical, or collaborating with AI, these tools can help you create a full-circle life where work, relationships, mind, and body all receive the attention they deserve. The future of work is personal and messy, but it's also filled with possibility. By working backwards, you can design a life that's not just successful by conventional standards, but deeply fulfilling on your own terms.

About Author

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Tim Duggan

Tim Duggan is an optimist who loves thinking about big ideas. He has co-founded several digital media ventures, most notably Junkee Media, one of the leading publishers for Australians.His first book, Cult Status: How To Build A Business People Adore, was awarded the BestEntrepreneurship and Small Business Book at the 2021 Australian Business Book Awards, and his second book on creativity, ‘Killer Thinking: How To Turn Good Ideas Into Brilliant Ones’, was named one of the Best Books of 2022 by Apple Books.Tim is the Chair of the Digital Publishers Alliance, an industry body that represents over one hundred and fifty titles from leading independent digital publishers. He began his career as a music journalist for Rolling Stone, and lives with his husband in Mallorca.

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