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Beschreibung

“This is a rare book: both profound and useful” —Seth Godin

Life-changing guide to a more fulfilling work life, inspired by cultures and companies around the globe

If you're feeling overworked, disengaged or apprehensive about the future of work or your career path, Work Backwards: The Revolutionary Method to Work Smarter and Live Better is the perfect guide to question the way you think about your workplace and put yourself on a track to a more fulfilling life. Written by Tim Duggan, media entrepreneur and author, who has helped thousands of individuals create their ideal lives through his renowned workshops, this book takes readers around the world to see how different cultures interact with work, revealing how we can implement new ideas to improve our own approach.

In this book, readers will learn:

  • Why reversing your thinking about work can have such an oversized impact using the three things you need to live a fulfilling life right now
  • How to easily reset your life-work balance to use tools like remote, hybrid and flexible work properly
  • What leading research says about work and happiness and how to put theory into action

Entertaining, inspiring and highly practical, Work Backwards: The Revolutionary Method to Work Smarter and Live Better earns a well-deserved spot on the bookshelves of all individuals who are seeking to not just tolerate work, but love what they do.

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Table of Contents

Cover

Table of Contents

Title Page

Copyright

Dedication

Introduction: The end

Harsh truths

Wrong direction

Notes

A better way

Default mode

Work Backwards

Notes

Life

The games we play

Notes

A life worth living

Notes

We can’t unsee

Notes

Make life work

Notes

Work Backwards Step 1:: Create a MAP

Meaning

Meaning at work

Job crafting

Meaning outside work

Purpose vs meaning

Notes

Anchors

Know your anchors

Anchoring yourself

Notes

Priorities

Life–work balance

Full circle

Coming full circle

Notes

IRL Exercises: Life

Money

Happy go lucky

Notes

Work-and-spend cycle

Notes

Work Backwards Step 2:: Know your ‘enough’

Handy man

Notes

Money and happiness

Notes

Backwards Budget

IRL Exercises: Money

Work

Ceiling cracks

1. We are overworked

2. We are disengaged

3. We are apprehensive

Notes

Myths and realities

Your future of work

Notes

Work Backwards Step 3:: Use the right tools

The upside-down swan

Notes

Reframing the tools

Tool: Remote working

How to use this tool

Notes

Tool: Hybrid working

How to use this tool

Notes

Tool: Flexible working

How to use this tool

Notes

Tool: Four-day work week

How to use this tool

Notes

Tool: Career breaks

How to use this tool

Notes

Tool: Sabbath time

How to use this tool

Note

Tool: Artificial intelligence

How to use this tool

Notes

Tool: Better meetings

How to use this tool

Notes

IRL Exercises: Work

Conclusion: The beginning

Acknowledgements

About the Author

Index

End User License Agreement

Guide

Cover

Table of Contents

Also by Tim Duggan

Title Page

Copyright

Dedication

Work Backwards

Introduction: The end

A better way

Begin Reading

Conclusion: The beginning

Acknowledgements

About the Author

Index

Advertisement

Advertisement

End User License Agreement

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Also by Tim Duggan

 

Cult Status: How to Build a Business People Adore

Killer Thinking: How to Turn Good Ideas Into Brilliant Ones

“This is a rare book: both profound and useful.” —Seth Godin

 

Tim Duggan

Work Backwards

 

The revolutionary method to work smarter and live better

 

 

 

 

 

This edition was published 2025.

© 2025 Tim Duggan

Edition HistoryThis edition was first published 2024 by Pantera Press Pty Limited.

All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, except as permitted by law. Advice on how to obtain permission to reuse material from this title is available at http://www.wiley.com/go/permissions.

The right of Tim Duggan to be identified as the author of this work has been asserted in accordance with law.

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John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, USAJohn Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex, PO19 8SQ, UK

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Cover Design: WileyAuthor Photo: Courtesy of Cybele Malinowski

 

 

 

 

 

This one’s for you, Dad.

 

 

 

 

 

Work sucks

So don’t listen to anyone who says that

It can be fulfilling and enjoyable

As despite what you might think

The only reason we work is for money

It’s wrong to say that

We have to prioritise life over work

Because it is the most important thing

 

(Now read it backwards)

Introduction: The end

The way we are working is broken, and it’s up to us to fix it.

We are crowded into cubicles, worn out on worksites and exhausted in executive roles as office towers stretch high into the heavens, dominating our horizons and psyches. Over the last few decades, almost every industry has been squeezed by longer hours, higher expectations and increased stress, and the end result is literally killing us.

Too many of us are overworked, disengaged and increasingly apprehensive about the future, and much of this malaise can be traced directly back to the role and importance we’ve placed on our jobs, giving it top priority in our lives – to the detriment of everything around us. We have let work dictate how we should live, and now something is about to break. If we don’t make changes soon, that something will be us.

This was the heavy realisation that hit me as my father lay on his deathbed. In those final, delicate moments where time stands still before it’s up, life’s unimportant trivialities, unfinished jobs and never-ending to-do lists finally melt away, leaving only a wide metallic hospital bed, clammy white hands and an unquenchable thirst. At least, that’s what it felt like during the last few hours of my dad’s life.

I’d driven him to hospital a few weeks earlier, the pain of years of compounding cancers growing inside his body breaking his usually stoic facade. My dad had battled through various illnesses over decades, from lung cancer in his forties to bowel cancer in his fifties. But the one that got him in the end was multiple myeloma, a type of blood cancer that grows inside bone marrow. This incurable disease, sometimes morbidly nicknamed ‘liquid cancer’, can be temporarily dampened by a smorgasbord of drugs, radiation and chemotherapy that zaps any remaining energy, until you’re the patient in Room 628 counting down your hours.

In his final weeks, my father experienced the piercing clarity that comes from knowing your days are numbered. When a visiting priest delivered his final rites, alone in a darkened room, he emerged with tears in his eyes. ‘In all of my years,’ the priest said, ‘I’ve never seen someone so at peace with their life. He told me that he has not one single regret, and is ready to die a contented man.’

Work was an important part of my dad’s life and identity, but never his primary personality. He started a business with a friend, then spent four decades building a successful company with his name on the front door. Outwardly, it was his biggest achievement, but on his deathbed, almost none of that mattered. In the remaining few days, as his breathing slowed and became guttural, all that dominated his thoughts were the people who’d been part of his life: my mum, me and my siblings, his family and friends. As we flitted around his bedside like moths, taking turns to stroke the back of his hand or moisten the inside of his mouth with a tiny wet sponge, he revisited stories of adventures on holidays, family birthdays around the dining table, personal and sporting achievements and time spent on the ride-on lawnmower at his beloved farm. Work hardly rated a mention. All those promotions, late-night emails, corner offices and pay rises won’t mean a damn thing when you’re on your deathbed, holding the hands of your loved ones as you wheeze your final breath.

The loss of a parent feels like being violently knocked off a bike that you’ve spent your whole life learning to ride. When you finally pick yourself back up, you realise one of the handlebars, something you assumed would always be there, is missing. It takes some practice, and many more falls, to learn how to ride properly again, but eventually you get back up and balance, moving forward on a bike that will never be the same.

The years leading up to my dad’s inevitable death ignited something deep inside me as I sorted through fresh memories, earmarking those to keep. He lived an extremely full life, balancing work while fostering deep relationships, pushing his own body and mental capacity right up until the end. Any death is a sobering moment for those lucky enough to still live; a time to stop and reassess, spending quiet moments in reflection to confirm that your values and priorities are aligned with the direction you want to go in.

For years I’d had a gnawing sensation that something wasn’t quite right with the way we are living and working. I’d begun working full-time in the mailroom of an advertising agency straight out of school, before co-founding my first digital media title with friends in my mid-twenties. Over the next 15 years I gave everything I had to work, helping to build a business with 60 full-time staff – a company we sold in 2016 and I left in 2020.

Inspired by the sense we were in the middle of a momentous shift in the way we work, supercharged by the global pandemic, I began experimenting with different ways of living and working. First, I experimented with location, spending six months working out of a motorhome as my husband and I drove to the sunburnt edges of Australia. We mixed up the usual Monday to Friday schedule, packing as much work as we could into the first few days of each week, leaving the rest of the time free to do what gave us joy, like travelling, exploring, hiking, cooking, reading and snorkelling.

Luckily, my husband’s job, like mine, could be done from anywhere with a power point and an internet connection, and we soon swapped our campervan for six months living in Australia’s Top End, basing ourselves in Darwin. Each working day, we’d dial into video calls from our sun-soaked apartment, then close our computers and spend the afternoon in the pool or at the local swimming hole to cool down.

But the biggest experiment of all came in 2021, when we moved to Europe to combine travelling and working into one occasionally messy but always glorious journey. We crawled through Greece, Israel, Mexico and Finland before making a home on the Spanish island of Mallorca. Here, we wake up early a few mornings to communicate with Australia during the time zone crossover, and then have several precious hours of deep, productive thinking before knocking off for a late lunch, a siesta or an afternoon swim in the Mediterranean. I acknowledge the enormous privilege I have in terms of financial and travel freedom; I’ve sold several businesses and I don’t have any children, but my own journey is just a starting point for the ideas explored in this book through the perspectives of scores of people you’re about to meet. It took me a long time, and many different experiments, to learn my ideal way of living and working, and that discovery has redefined the role work plays in my life.

The happier I felt experimenting, the more obsessed I became with understanding why it took over two decades to find a way through the noise and make work finally work. I started seeking out others who were also experimenting with different ways of working and living, emboldened by an unprecedented opportunity to bend the rules to achieve the lives they wanted. Many were motivated by the depressing reality of the path they saw laid out ahead of them, a conveyor belt that they didn’t want to blindly travel on.

I read and spoke about the future of work with dozens of the world’s leading experts to try to understand where we are heading. In doing so, I became dismayed. I discovered that hundreds of independent research studies are all flashing amber, their combined alarms warning us that our current approach is broken, making us overworked, disengaged and apprehensive about our trajectory.

Harsh truths

The research on work is overwhelming and depressing. A global Gallup study found that average stress levels at work increased by 42% between 2009 and 2022.1 Burnout is at an all-time high across most professions,2 and that’s not confined by borders – McKinsey Health Institute3 showed that almost a third of all employees worldwide reported experiencing burnout symptoms sometimes, often or always. In the highest-ranked country, India, almost 40% of workers reported feeling this way. In China, there’s a common expression, ‘996’, which means pride in working 9 a.m. to 9 p.m., six days a week, something Alibaba billionaire Jack Ma called a ‘blessing’.4 Japan even has a term, karoshi, that translates as ‘death by overwork’ – which the Ministry of Health legally recognised as a severe problem in 1987, and which continues culturally to this day.5

The way we are working is literally killing us. The World Health Organisation concluded that long working hours led to 745,000 deaths from stroke and ischemic heart disease in 2016 alone, a 29% increase since 2000.6 The study, in partnership with the International Labour Organisation, showed that working 55 hours or more per week – the equivalent of the relatively common white-collar timetable of 8 a.m. to 7 p.m. Monday to Friday – is associated with an estimated 35% greater risk of a stroke and a 17% higher risk of dying from heart disease, compared to working the standard 35 to 40 hours a week.

But, I can already hear you whisper in defence, what about all of the positive changes that emerged thanks to the global pandemic and the shift to working from home and working remotely? We’ll get to those in detail later, but for now it’s important to point out that some of those changes have actually exacerbated our overwork culture. Microsoft, which collects data every time you interact with one of their products, tracked the amount of hours that people around the world spend using their Teams software. They found that when many office workers shifted to logging in from home instead of the office, the length of the average workday increased by 13%, or 46 minutes, in the two years after the pandemic began in March 2020.7 And where traditionally most professional workers had two productivity peaks in their day, before and after lunch, the same researchers observed the emergence of an additional peak since the pandemic, with a third bump of work taking place in the late evening. They call this phenomenon a ‘triple peak day’.8

No matter which way you look at it, we are caring less about work. Data from workers in 155 countries shows that almost two-thirds of us are emotionally detached at work,9 and only half of US workers said they were really satisfied with their jobs.10 In the aftermath of the pandemic, almost 40% of people said the importance of work had diminished for them during the Covid years.11

Lastly, we’re becoming increasingly nervous about the uncertain future we’re heading into. Alongside growing climate and general anxiety, an increasing number of people are apprehensive about the effect of artificial intelligence (AI) on the labour market. A PwC report found around 60% of Australians are worried about the future of their work and their job prospects,12 and around a third of workers are already worried that their roles could be replaced by AI technology in the next three years.13

Combined, that’s a lot of research screaming that something has to change, and fortuitously, it’s all happening at the most extraordinary moment for us to rethink our relationship with work. During the years that the pandemic ravaged the globe, we collectively lived through the largest global workforce experiment in a century, exposing us to what a tantalising new future could look like. And now we have a once-in-a-generations chance to rethink it all – but exactly how do we go about it?

That’s the thorny question I’ve spent years getting to the bottom of. I’ve spoken to workers in a wide variety of professions. I met a couple of bakers in Glasgow who only open their bakery two days a week in order to reclaim some of their lives from their work. I met a start-up CEO who lives in Thailand to be closer to his family, while the rest of his employees work from another country. I met a photographer and his wife who’ve built a successful business out of him going surfing with a camera every morning. I met a tradesman in Southern Virginia who balances his week so he can spend more time doing what he loves. I met an office worker in Sydney who now works three days a week so she can spend more time with her kids, and ironically earns more than when she worked five full days. I found each of them inspiring in their own way – and you’re about to meet them too, plus dozens more.

The reasons why our approach to work has broken can be roughly lumped into two categories, structural and individual. Many of the structural causes are interlinked with growing inequality. There is structural inequality in the way our economy operates, and income inequality where salary levels can determine life outcomes. There are also gender, race, class and other inequalities that have been hardwired into the way our society operates. Trying to shift these root causes will take radical, long-term political pressure to achieve ideas such as a universal basic income and fair legislation that takes into account all members of an economy.

Unfortunately, it’s going to take more than a book to solve these structural problems. What we can control is the way we as individuals think about how and why we work, which can have an enormous impact on our own lives. How change happens is something I’ve been studying for over a decade. When I was running the media company I co-founded, Junkee Media, we ran one of the largest longitudinal studies on Australian youth, and there was one particular question I found extremely illuminating. We asked our audience, ‘Where do you think change for the better in society will come from?’ to find out if there was a specific area, age group or institution who would drive the societal change we so desperately need.

We originally forced respondents to choose only one option, and when we did that, most people deflected the responsibility of change onto someone else. The highest-ranked answer regarding where this change would come from, at 16%, was the federal government and media. This was followed by scientists (14%), friends and family (14%) and lobby groups (12%). One of the lowest-ranking options, at just 6%, was ‘me’. In other words, when given only one option, most people overwhelmingly thought change for the better would come from someone other than themselves.

However, when we gave respondents the ability to choose multiple options in response to this same question, something truly fascinating happened. Personal responsibility, or the number of people who said change was going to come from ‘me’, alongside any of the other options, jumped dramatically, from 6% to 46% – the same level of responsibility as the federal government. This shows that people do want to play a role in bringing about change, but they can’t do it alone. The desire for change is strong, as long as it’s effected in tandem with other institutions. When we examined the data further, we found that an even larger proportion of women (50%) than men (43%) said that change would come from them in partnership with others. There are many examples of businesses, government, scientists and the media that are agitating for a change to the way we work, and you’ll meet them throughout this book. We need to seize this moment, and use that momentum to push, provoke, challenge and change how we think about work forever.

All of these years of experiments, research, interviews and thinking have led me to a simple conclusion about the problem and solution on an individual level: the way we are working is broken because we are living our lives in the wrong direction. We’re beginning at the incorrect starting line and aiming for the wrong destination.

Wrong direction

Most of our lives play out in a fairly typical way, without us giving it much active thought. The default path for many people is that you leave school or university, and start looking for a job in an area that matches your skills and experience. You land a job with a company, starting in the most junior position. In exchange for your labour, your employer decides how much they will pay you per hour, week or month. That payment drops into your bank account, and gets divvied up to cover bills, credit cards, rent, petrol, food, necessities and Netflix, until it all seems to dissipate just as quickly as it appeared.

The next month, another salary is deposited and the cycle repeats again. This continues over and over, until work becomes primarily a means of getting enough money to pay for the lifestyle you’ve developed. There’s even a term for this: lifestyle inflation. It helps to explain why the more your salary increases, the more you spend, until you realise you’re caught in a common, dangerous rip that’s hard to get out of. Most of us repeat this cycle over and over, with very few chances to draw breath, until we retire. No wonder we feel overworked, disengaged and apprehensive.

The bad news is that the way we are currently working – and, by extension, living – is broken. The good news is that it doesn’t have to be this way. Instead of the default mode we have become accustomed to, where we think about work, money and life in that order, we need to reverse it and see it in a fresh light.

This is what it means to Work Backwards, and this book is structured in the order that we need to approach these elements: life first, then money and, lastly, work. Alongside these stages are three simple steps to show you how to do this. You’ll get inspiration, ideas and new tools that anyone – full-time employees, contract workers, students, business owners and freelancers – can use to make work actually work for you. The lessons in this book will serve you at different times of your life, and can be referred back to as you progress. For simplicity, everyone will fall somewhere on the scale of three primary categories of readers: early, mid and late career. Note that I have intentionally not divided these by age, as there’s nothing worse than someone telling you where you ‘should’ be at based on how many birthdays you’ve had. We all have unique lives with winding career journeys and can forge our own paths at our own pace.

Early career means you’re at the beginning stages of your working life, where you have enormous opportunity to consider the direction you want your life to head in before you’ve really got started. While this might seem like the easiest time to resist the default mode of living, it’s also one of the times when you’re the most vulnerable. Without as much real-world experience, you can easily be led astray by well-meaning people who apply their own biases and personal experience. This book aims to question your expectations and show you alternative ways of working and living; it is a hopeful roadmap that you can apply right from the beginning, to set you up in the best possible way to live a fulfilling, happy and productive life.

If you’re mid career, you’ve spent a decade or two in the workforce and you understand how the game works. You’ve likely begun to question if the way you are working and living is right for you, but it can be hard to know what steps you can take to regain some balance. Also, you might theorise, you’re in the stage of your life where work is meant to be hard, right? But the longer that goes on, the more you realise it’s up to you – and only you – to reclaim your life. The mid-career stage is also the time when many people start young families, injecting a larger priority into your life that screams, quite literally, for your attention. In the midst of all this, it can be difficult to think about making any seismic changes, but even small tweaks to the way you work can have a big impact at this stage.

People who are late in their career are the most experienced of all. You’ve seen your workplace, and life, evolve in unexpected ways. You’ve lived through ups and downs of relationships, family changes, wars and economic booms and busts. By this stage, there is little that fazes you, and that’s a superpower of its own. Paradoxically, the later in your career you are, the more options you have regarding how to live your life. Your family might be grown up, you might have some resources saved up or inherited, and at this stage you have less to lose by using this framework to change the way you work and live.

It doesn’t matter which stage you’re in, this is a radical invitation to take your life back and wring every last drop out of it. At times, applying these principles might feel like trying to rebuild a plane while you’re flying it, but the reward is worth all the effort. You will spend up to one-third of your life at work, so changing your approach will have cascading benefits on how you live.

Let’s also be brutally honest here. There are always going to be periods of your life when that idealised vision that you know you should be heading towards feels further away than ever. Take the first few years after becoming a parent, when everything gets turned upside down, the starting chapter of a new business, or a particularly intense patch of your career, when you decide you’re going to give work every ounce of energy for a set time period with a clear end goal in mind. That is perfectly normal, and the path to a healthy way of working is not always linear. The important thing is that you know what you’re aiming for.

As individuals, we each play an important role in deciding how and why we work, and there’s never been a better time to rethink it than this moment right now. If enough of us redefine what it looks like together, we have the real ability to pick up some of the broken pieces and reassemble them in a much better way.

Notes

1

Ray, J. (2022).

World Unhappier, More Stressed Out Than Ever

.

Gallup.com

.

https://news.gallup.com/poll/394025/world-unhappier-stressed-ever.aspx

.

2

Abramson, A. (2022).

Burnout and Stress Are Everywhere

. American Psychological Association.

https://www.apa.org/monitor/2022/01/special-burnout-stress

.

3

McKinsey Health Institute (2022).

Addressing Employee Burnout: Are You Solving the Right Problem?

www.mckinsey.com

.

https://www.mckinsey.com/mhi/our-insights/addressing-employee-burnout-are-you-solving-the-right-problem

.

4

Shane, D. (2019). Jack Ma Endorses China’s Controversial 12 Hours a Day, 6 Days a Week Work Culture.

CNN Business

. 15 Apr.

https://edition.cnn.com/2019/04/15/business/jack-ma-996-china/index.html

5

Fuerte, K. (2021).

The ‘Karoshi’ Phenomenon Is Now a Worldwide Problem

. Observatory of the Institute of the Future of Education.

https://observatory.tec.mx/edu-news/karoshi-phenomenon/

6

World Health Organisation (2021).

Long Working Hours Increasing Deaths from Heart Disease and Stroke

.

www.who.int

.

https://www.who.int/news/item/17-05-2021-long-working-hours-increasing-deaths-from-heart-disease-and-stroke-who-ilo

7

Microsoft (2022).

Great Expectations: Making Hybrid Work Work

.

www.microsoft.com

.

https://www.microsoft.com/en-us/worklab/work-trend-index/great-expectations-making-hybrid-work-work

8

Microsoft.

The Rise of the Triple Peak Day

.

www.microsoft.com

.

https://www.microsoft.com/en-us/worklab/triple-peak-day

9

Gallup (2022).

State of the Global Workplace Report

.

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10

Greenwood, S. (2023).

How Americans View Their Jobs

. Pew Research Center’s Social & Demographic Trends Project.

https://www.pewresearch.org/social-trends/2023/03/30/how-americans-view-their-jobs/

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Qualtrics.

Return to Work / Back to Business Study, Part 2

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https://www.qualtrics.com/m/assets/wp-content/uploads/2020/07/Back-to-Business-Round-2.pdf

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PWC (2021).

Hopes & Fears: Future of Work

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PWC (2022).

PwC’s Global Workforce Hopes and Fears Survey 2022

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https://www.pwc.com/gx/en/issues/workforce/hopes-and-fears-2022.html

A better way

It’s easy to get lost in the narrow, winding streets of Jerusalem. The ancient city is carved up into four distinct quarters, each inhabited by Jews, Muslims, Christians and Armenians respectively, who have each fiercely and passionately protected their corner of the historic town for centuries.

But despite its significance as the centre of multiple religions, the old city is crammed into a tiny parcel of land that totals less than one square kilometre, walled in on all four sides by stony, sunburnt walls. Internally, each quarter is separated by differences in archaeology and ideology. The Jewish Quarter is dominated by the Western Wall and dozens of crumbling synagogues. The Muslim Quarter is packed tight with sellers hawking spices, incense and brassware on every corner. The Armenian Quarter is mostly walled off, allowing its residents to live quietly away from the crowds. And if you wander through each of the quarters and follow the natural slope of the streets downwards, you’ll eventually end up in a small, unassuming courtyard in the Christian Quarter that faces directly towards two large wooden doors. These doors guard the most contested church in the world.

It’s estimated there are between 8 and 16 million churches1 on Earth. No one is quite sure of the exact number, but there is consensus at least on which of those is the holiest for the two billion followers of Christianity. The Church of the Holy Sepulchre is built on the supposed sites of two of the most important locations in Christian history: the rock that Jesus was said to be crucified on, and the empty cave where it’s believed he was buried and resurrected.

Unsurprisingly, this church is always teeming with people. At every hour of the day, thousands of tourists queue ten-deep to enter the altar built over the land where the tomb once stood, lining up to shuffle underneath a small table and place their hand into a dark crevice to rub the surface of the rock formation that Jesus may have been crucified on. The combination of emotional pilgrims, hazy processional smoke, noisy tourists and a haphazard layout make it an overwhelming experience.

Part of the reason for this chaotic feeling inside the church is that no one actually takes full responsibility for the maintenance of the holiest building on Earth. There are six denominations that all share the burden: the Greek Orthodox, Armenian Apostolic, Roman Catholic, Coptic Orthodox, Syriac Orthodox and Ethiopian Orthodox, and none of them can agree on who controls the church. After centuries of fighting over who had the right to use the building, in the 1700s all six denominations reluctantly came to the agreement that they would not do anything to change the building in any way without the consent of all the other owners. This agreement means that nothing ever changes. The most important church in the world remains frozen in time due to fear of action.

If you stand in front of the Church of the Holy Sepulchre today, watching dazed tourists spill out into the sunlight, and raise your eyes a few metres above the main entrance towards a small ledge, you’ll notice something unusual: a single ladder – five rungs, wooden – leaning casually up against the wall. It looks like a tradesman may have left it there and will return any minute now to pick it up.

But nobody will be moving it. This rogue ladder has been leaning against the facade of the church since at least 1728, when a black and white engraving of the building first captured it there.2 For three centuries it’s remained stuck in place, because none of the six groups can agree on who should be the one to move it. This solitary ladder is a stubborn tribute to doing nothing, purely because that’s the way things have always been done.

The immovable ladder of Jerusalem is an extreme example of what happens when you get so blinded by the mirage of stability that you give up on trying to make any sort of change. It’s a perfect symbol of the price of inaction, and once you become aware of these symbols you start seeing them everywhere.

Humans are hardwired to take the path of least resistance. We lean towards what our ancestors and peers have always done, often unconsciously modelling our behaviour on what is most familiar to us without questioning if it’s the right or best course of action. Neuroscientists call this our Default Mode Network, an interconnected series of brain areas that are most active when you’re not focused on what is happening around you. While you might not know the scientific name for this, you’re certain to have felt it in action. Have you ever commuted to work without consciously thinking about where you are going? There’s a part of your mind that can switch into autopilot, telling you which bus stop to get off at, what direction to turn and when you should cross the street. When you arrive at work, your mind has been so busy thinking through other things – daydreaming, solving problems, going over old conversations or planning for the future – that you hardly remember the journey you took to get there. That is your brain’s Default Mode Network in action, and it’s what happens when we perform tasks without thinking much about what we’re doing.

This is what many of us are doing with our lives. We are living on autopilot, giving little thought to where are we heading. This is a behaviour that pops up in all aspects of life, from relationships to financial habits and everything in between. It is especially pertinent to the ways that we traditionally work, such as a typical Monday to Friday, nine-to-five work week and other workplace norms. The 40-hour work week has been the status quo for roughly a century, since workers around the world began revolting against the longer weeks that the industrial revolution had ushered in. There has been little change to this system since the late 1800s, despite almost everything else we do evolving significantly since then.

This sleepwalking way of living is driven by fear of the unknown. We are so used to it that it’s easier to just shrug and put up with it – just like the immovable ladder of Jerusalem. The direction of our lives hasn’t changed in a century. Don’t you think it’s about time it did?

Default mode

Our standard approach to work tends to follow a cycle that begins around our early twenties and continues on a loop until we retire. It goes like this: when you finish school, some people head to university to study, others move overseas to travel, and many head straight into the workforce, trying to learn new skills you can use to build a career over the coming decades. Most of us have no idea what we want to do, so the area you begin working in might be influenced by factors such as proximity to your house, a suggestion from a careers counsellor, someone you saw in popular culture, a connection through friends or family, or an available job that requires little experience. We tend to go with what’s most convenient at the time, without really considering that this could set us on a path that we might follow for the next four decades.

Eventually, after graduating, returning from travel, or fuelled by a need to earn money, you start looking for full-time work. This is usually Monday to Friday, but it can also be shift work or after-hours work, depending on the industry. You scour job boards, sign up to endless daily career-website emails and suggestions from LinkedIn. If you’re connected enough, you might try to network with people you know in the field, leaning heavily on contacts for introductions, leg-ups and anything that might give you an advantage over other candidates.

With enough luck, and patience, you eventually find a job ad that looks interesting. You apply, often along with hundreds of other applicants, crossing your fingers that your experience and neatly typed CV are good enough to land you an interview. Then, finally, yes! You get an email inviting you to attend an interview.

You get excited, research the company, practise the interview, and then nervously turn up on the day. It’s all a bit of a blur. Afterwards, you can’t recall many of the questions they asked, except that one time you floundered a bit, desperately trying to give them the answer they wanted. You’re certain that was the moment you lost the job. You constantly check your emails and phone for the fortnight they said the interview process would take, convincing yourself that you messed it up and the job will go to someone else.

After an agonising wait, you get an unexpected phone call. They offer you the job, and you’re over the moon to finally have some paid work. They email you a contract, and you get to properly read the details of the offer – the title, the salary, the start date. Of course, you’d like a higher salary (who wouldn’t?), but it sounds pretty reasonable, and you’re just happy to have secured a steady job and a regular income. You return the signed contract enthusiastically. Congratulations, you’ve got a job.

The value exchange of labour for resources is as old as time. The primary reason most people work is to earn money to feed, clothe and advance ourselves and our family. When you start any new job, your employer will inform you how much you will earn to compensate you for your time and effort. Occasionally there’s some room for negotiation, but this figure is generally set by the employer with little input from the employee.

From then, your salary is paid every week, fortnight or month. For a hot minute, you check your bank account and feel rich, but that temporary relief is quickly replaced by reality once your bills have all been paid: food, rent or mortgage, credit cards, transport and on and on and on. But here’s the thing about this part of the cycle: you don’t have much control over what your salary is. Sure, you can affect this by working hard and getting promoted, or through deft negotiation, but it’s broadly determined by your employer. They give you a fixed salary, and you have to make your life work around how much you get.

Once you’ve got your salary in your bank account, it’s quickly dispersed to pay for your life. What this means is the most personal part of this process. Life might mean that a fifth of your pay goes on your car repayment so you can drive your dream car. Or maybe half goes towards the mortgage you took out to buy your first apartment. Or to paying off the credit card you took out to pay for your last European holiday. Whatever your salary is spent on, it’s being used to fund your lifestyle. The problem here is that most of us haven’t consciously decided what this lifestyle is. It’s just something that creeps up, with bills, costs and commitments that seem to appear out of nowhere. And the more you are paid, the higher these bills are. Sometimes your pay is barely enough to pay for basic needs like food and accommodation, and not much more.

In this scenario, life is what’s left over once you’ve paid your bills. It can all be a bit depressing, sad and unfulfilling. It’s also not uncommon. In 2022, almost two-thirds of Americans lived from pay cheque to pay cheque, an increase from 57% in 2021. It’s not just low-income earners either. Almost half of those earning over US$100K a year reported that they were doing the same, up from 38% in 2021.3

If we were to visualise the default mode of living, it would look like this:It’s a familiar flow that underpins our modern capitalist society; the same order our parents followed, as well as their parents, and theirs before them. The cycle begins with our first job, all novel and exciting when we’re early in our career and everything is new to us. As we enter our mid careers and ingrained work habits begin to form over a decade or two of the same pattern, the cycle begins to grate. ‘Is this it?’ you might think. By the time we’re in our late career, the cycle has truly worn thin, and many are left holding on by a single thread as they eye off their retirement.

Surely there has to be a better way? As it turns out, there is.

Work Backwards

Instead of just sleepwalking along the regular path, we have to start with the end point first. Instead of work–money–life, we need to reverse our thinking, starting with life, then money, and then work to design the life you want. This book is divided into those three sections, and at the end of each section is a step on how to put it into practice. This is what it means to Work Backwards, and this is what it looks like:

Life

Step 1: Create a MAP

The first step is to begin with the end result that you want to achieve. Consciously decide how you want to live, taking into account your passions, skills, happiness and the impact you want to have. You wouldn’t set off in a new direction, to chart an unknown course, without having some idea of where the heck you want to go, right? To put life first, you need to create a MAP, which stands for knowing your Meaning, Anchors and Priorities.

Money

Step 2: Know your ‘enough’

Once you’ve defined where you want to go, you need to work out how much money it will cost to get there. In this second step, you have to know what ‘enough’ means for you, then plan out in detail exactly what that looks like. You need to take back control and consciously plan what it costs to live a life that aligns with what you want, including how much money, success and ‘things’ you require to be happy.

Work

Step 3: Use the right tools

In the final section, you’ll better understand all the extraordinary tools you now have access to, and how to best use them. You have to cut through the noise around where work is heading, and instead see things like hybrid workplaces and four-day work weeks as tools to be experimented with, evaluated, used and adapted to meet your needs. The tools you use will change depending on your situation, life and career stage.

This is what the Work Backwards framework looks like in a single image:

To help you apply the Work Backwards framework to your life, at the end of each of the three steps is a section called IRL. In case you don’t live on the internet, IRL stands for ‘in real life’ and it’s a series of ten exercises where you can apply the theory you learn in this book into real-world action today.

This book is yours to use it in whatever order you like. You might want to stop at each IRL exercise and complete it right then, or you might prefer to read the entire book first and then return to the exercises you want to complete. It doesn’t matter how you use it, just that you do, and even applying some small changes to how you work can have a revolutionary impact on your life. You can also download a free detailed workbook to help you complete each of the ten IRL exercises from WorkBackwards.com/IRL that will make it even easier.

The future of work is personal, messy and here right now, but my future of work is very different from yours, which will be different again from your neighbour’s. The life that you want is unique to you, and in this book you’ll learn a simple three-step process to rethink how and why we work, helping you design a better way to live. And to do that, we’re going to start at the end.

Notes

1

Kramer, H. (2017).