Work Optional

Retire Early the Non-Penny-Pinching Way


By Tanja Hester

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A practical action guide for financial independence and early retirement from the popular Our Next Life blogger.

In today’s work culture, we’re expected to hustle around the clock. But what if you could escape the traditional path and get on one that doesn’t require working full-time until age 65? What if you could wake up every day without an alarm clock and do the things you love most?

Tanja Hester and her husband Mark left their crazed careerist lifestyle to live their dream life in Lake Tahoe, retiring early from high-stress careers. Now Tanja will help you map out a customized plan for freedom and make it easy to succeed, whether you’re good at math and budgeting — or not!

Work Optional is more than just a financial plan: it’s a plan for your whole life — designed by you, not by an employer or clients. Tanja walks you through envisioning your dream life, accounting for variables such as health care and children, protecting yourself from recessions and future unknowns, and achieving a purpose-filled early retirement, semi-retirement, or career intermission with completely doable, non-penny-pinching steps.

You can live a happier, more meaningful life, free from the daily grind. Regardless of where you are in your career, Work Optional will get you there.


Note to Readers

This book is presented solely for educational and entertainment purposes. The author and publisher are not offering it as legal, financial, accounting, health, or other professional services advice. While best efforts have been used in preparing this book, the author and publisher make no representations or warranties of any kind and assume no liabilities of any kind with respect to the accuracy or completeness of the contents. Neither the author nor the publisher shall be held liable or responsible to any person or entity with respect to any loss or incidental or consequential damages caused, or alleged to have been caused, directly or indirectly, by the information contained herein. No warranty may be created or extended by sales representatives or written sales materials. Every person’s situation is different and the advice and strategies contained herein may not be suitable for your situation. You should seek the services of a licensed tax professional, certified financial planner, or tax attorney for counsel on your situation. As with all investments, past performance is no guarantee of future results. Please consult your physician before beginning a new diet or exercise regimen.


It’s eight p.m. on a Friday, and I’m asleep on the couch. Again. My husband, Mark, is asleep beside me. Again. This has become our pattern: work too much and sleep too little all week, and then collapse into the weekend, too exhausted to get through even a single 30-minute TV show. Around one a.m. I’ll wake up, wake up Mark, and then trudge off to bed, and somewhere in those few dozen steps, I’ll wonder, Is this really what I’ve worked so hard for? Is this what success feels like?

Work today is a far cry from work of the not-so-distant past. In the seemingly endless race to boost productivity and profits, companies expect their employees to work more and more hours for less and less pay, and to be connected even when we’re not working. Entrepreneurs and freelancers are told they need to “hustle” around the clock to be successful. Sometimes it all feels just as pointless as collecting virtual coins in a video game as we chase new jobs, promotions, or opportunities that may or may not actually help us get ahead or make us happier, all the while drowning in never-ending email loops and power dynamics. We work for that paycheck, live for the weekend, and spend our money trying to soothe the stress of it all.

But you don’t have to live your life according to this script just because it’s what most people do. You can write your own script, one that puts you in control of your time every day—from how much work you do all the way down to whether you ever set an alarm clock again. I’ll show you just how doable it is to create your own work-optional life.

I had a dream career filled with purpose, working as a communications consultant to political campaigns and nonprofits I believed in, and seeing my work directly impact people for the better. I had the privilege of working with incredibly smart, driven, and kind people, and that made the work fun much of the time. But even a great job and steady string of promotions couldn’t offset the stress and exhaustion I felt constantly or help shake the feeling that I wasn’t really in control of my life.

Though I loved a lot about my work, I also flew nearly a million miles during that career, spent hundreds of nights in hotels away from home, and banked more 70-hour weeks and all-nighters than I can count. The impact from my work might have felt good, but the pace of it wasn’t sustainable, and I knew it. I also knew that I wasn’t getting happier with each promotion. If anything, the added responsibility was making me more stressed and tired, more disconnected from the purpose behind my work, and less sure of the direction my life was taking. The higher up the ladder I climbed, the less time I had to spend with the people I care about and on the activities I love most. This put my career goals in direct opposition with the happiness and fulfillment I craved. And even when I enjoyed the work, I was still spending my time and energy on someone else’s agenda, not my own.

Maybe you’ve had similar thoughts. You’ve wondered what all that time you spend working really adds up to. Or how you’ll ever be able to find time in your life for the people and things that are truly important to you. You’ve worried that your life is passing you by, and that you might get to the end of it and realize you didn’t do what you’d always dreamed of doing or what would give your life meaning. Maybe you’ve chased money or prestige, but realized that getting it didn’t make you any happier, and you only had to work more year after year to hang on to your position.

It was during all that ladder climbing and questioning that I met my husband, Mark, who was also on a steep trajectory in an equally demanding career as a political researcher. We were proud of our careers and felt incredibly fortunate to work for companies and people we respected, but we saw the toll those careers were taking: how little we were sleeping, how much the stress was impacting our health, how unable we were to disconnect for more than an hour or two, how desperately we came to need the weekends (even if we often worked or slept through them) and too-short vacations. And not only did we want to free ourselves from the constant stress and exhaustion of our careers, but we also had other things we’d rather spend our time doing. Every chance we got, we were making the hours-long drive from Los Angeles up to the Sierra Nevada mountains, where we’d ski in the winter and hike and climb in the summer. We felt most alive zipping open a tent in subfreezing temps at dawn from some high-altitude vantage point, taking in the sunrise in solitude. Or racing to the ski slopes before the sun rose, in hopes of grabbing that elusive first chair on a powder day. And when we were home, we loved volunteering in our community, knowing we were directly helping people in need. But as we took on more responsibility in our careers, we had less and less time to get into the mountains and into the community, and we felt work pulling us away from what we loved most.

After one too many of those early Friday nights asleep on the couch, we decided that we didn’t want to live that way for another 30 or 40 years. And we made the choice to design a different kind of life: a life we’d live on our own terms, not an employer’s or a client’s. And so our journey to a work-optional life began, starting with a move from LA to the mountains near Lake Tahoe. I blogged about our journey to early retirement on my site, Our Next Life, and quickly heard from readers all over the world that they felt the same way we did. They didn’t want to wait until their 60s to wrest control of their lives back from their employers. And because you’re reading this now, I bet you’re in the same boat.

Six years after formulating our escape plan, we waved goodbye to our careers and embarked on a new life in which we never need to work again. I had just turned 38. Mark had just turned 41. We now ski more than we ever have, and we spend time on the trails nearly every day. We volunteer much more than we could while in our careers, which replaces the sense of purpose we used to get from work, and we have time to devote to creative projects that are meaningful to us. At least once every day, I think to myself, I can’t believe this is real life. We’re so grateful to have realized that by approaching our money a little differently than most people do, we could reclaim our time and embark on the work-optional life of our dreams.

If you’re willing to change your money mindset and occasionally go against what we’re all taught is the “right way” to do things, you can craft the life of your dreams, too.

This book is not anti-work. Work is a good and noble thing, something nearly every person ever born has had to do in some form, whether or not they were formally employed. As humans we are wired to be productive, and work provides an outlet for that need. Work can give us a sense of purpose, a sense of contributing to society, and a sense of usefulness. The problem isn’t work itself, but our current societal work culture. The culture in which too many of us wear our busyness and the bags under our eyes as status symbols. The culture that says you must hustle around the clock to be worthy. The culture that says our employers or clients own not just our work hours but every waking moment. We aren’t wired to handle that.

That’s why we see study after study confirming what most of us already know: Today’s work culture is crushing us. Workplace burnout is at epidemic proportions,1 and workers feel stressed and exhausted.2 Large numbers of us work 50, 60, or even more hours every week.3 While our parents or grandparents rarely had to take work home with them, and certainly weren’t reachable after leaving the office each day, we’re now expected to be connected at all times. A full half of us who use email for work check that email over the weekend. Almost as many check email when we’re sick, and a third of us check work email on vacation.4 (Is that even really vacation?) Typical senior-level employees are buried in more than 200 emails a day.5 We feel overworked and eager to escape, even if we like the work we do.

Today we also work more overall: In 1979, Americans worked an average of 1,687 hours a year, but now log 1,836 hours. This is the equivalent of nearly four more weeks of full-time work every single year.6 Nine out of 10 workers at all levels feel they don’t have enough time to get everything done that is expected of them.7 We’re asked to do the impossible, and we no longer have enough time to unplug and protect our physical and mental health.

At the same time, we feel less secure in our jobs than ever before, even those who love their jobs and can’t imagine retiring early. Many industries are being forced to adapt to technological changes and to downward price competition that result in outsourcing jobs overseas, replacing humans with robots, or closing up shop altogether. Some whole industries have gone extinct or are in danger of doing so. And other workers find themselves in occupations with a high risk of injury or disability, which could end their careers in an instant.

So it’s no wonder that so many of us are craving freedom from this fast-paced, high-pressure work world. We want to work on our own terms. We want to do something slower, something healthier, something more secure—or maybe just something different, something that makes our lives feel more meaningful.

That’s what Work Optional is all about: reclaiming your life from our nonstop work culture so that you decide what role work will play in your life, instead of society deciding for you.

It can take any form you imagine, from full early retirement with no paid work ever again, to a life with part-time or periodic work on your own terms. Maybe it’s a life in which you escape traditional employment and go to work for yourself with a big financial safety net in place to keep the work fun instead of stressful. Or a life of full-time travel, in which you can work when and where you want. Maybe it’s a service-focused life filled with volunteering or activism. It’s completely up to you to define what a work-optional life looks and feels like to you. And your journey to that life is completely yours to shape, too—from what path you’ll take to how fast you’ll go. If you find yourself getting hung up on the word retirement, then choose another word. You might call what you’re aiming for financial independence or financial security. Or maybe you simply call it a work-optional life. The words you choose are far less important than knowing what you want.

How to Use This Book

This isn’t one of those financial self-help books that’s going to push you to leap in hopes that the net will magically appear, or that’s going to ignore the financial realities of the world today and pretend that anyone can make a million dollars in a month or get out of debt overnight. I’m not going to try to convince you to take big risks or promise that if you do exactly what I did, you can achieve exactly what I achieved in exactly the same way. This isn’t ultimately about my journey. It’s about yours. That’s why the process in Work Optional is all about embracing your reality and finding your best options for reshaping your life. You’ll come away with a solid, cautious, comprehensive financial plan, tailored to your specific circumstances, that sets you up to weather whatever future storms come your way and with a purpose-filled life plan that will keep you motivated all along your journey. If you choose to take a less cautious approach, that’s cool! My goal is to empower you with all the information you need to shape your work-optional life, and to make your own choices about what’s right for you and your unique situation.

Work Optional is divided into three sections. Part I is all about envisioning the life that you would be thrilled to live in early retirement, semiretirement, or a series of career intermissions, such as taking a year off from work every five years or once a decade. We’ll look at what will provide you with a sense of meaning and fulfillment in lieu of a traditional career, and I’ll ask you to take a close look at what you would be willing to change or give up in your life now to make that dream a reality. For example, whether you’re willing to live in a smaller home, give up a car, or stop shopping for nonessentials. (Don’t worry. None of that is mandatory, but the more you’re willing to change, the faster you’ll reach your goal.)

Part II is the financial planning portion, guiding you through the process of understanding your current spending and projecting your future spending. You will come to understand all the principles that underpin a solid early retirement financial plan, determine how much you need to save to retire or semiretire securely, create a plan and timeline to save without having to pinch pennies, and put systems into place to ensure you succeed, such as automating your saving so that you aren’t continually drawing on limited willpower to set aside money each month. This section also covers strategies to speed up your progress toward your savings goal by increasing earnings and decreasing spending, perhaps by changing to a higher-paid career path or moving to a lower-cost-of-living area, and to build in contingency plans to create extra safety and security.

Part III gets back to the life part, when life after work becomes optional, planning how you’ll adapt to a post-work life financially and emotionally, prioritize your well-being, and make the most of your newfound free time. Most of all, this part is about actually living your best life.

Throughout the book, I share our story so that you can see one possible route to early retirement: how Mark and I envisioned the work-optional life we wanted to live instead of the work-centered conventional one, how we built our financial plan behind that, and the completely doable steps we took to make it our reality in a short period of time. But I want you to be inspired by other possible routes as well, and that’s why you’ll find lots of other people’s stories included here, too. Especially if you have kids, you may think a work-optional life is out of reach for you, and that’s why the majority of examples included here are from parents, not from child-free people like Mark and me. From families with kids who retired early, to single people pulling it off, to couples earning under six figures combined saving faster than you might think possible, you’ll see that some form of work-optional life is achievable for nearly anyone who can afford to save even a little. No matter what your circumstances are or where you’re starting, you’ll come away from this book with a detailed, concrete plan to make your dream of less work and more life a reality.

My hope is that, by seeing so many different paths to early retirement, you’ll finish this book inspired to envision your work-optional future and pursue it doggedly, like your life depends on it. (It does!) But doing that requires hard work on your part. There are some tough questions here, like:

• What does your work-optional dream life look like in very concrete terms?

• What are you willing to sacrifice to get to that goal?

• What do you want to be able to look back on at the end of your life and know you did?

Get ready to do some introspection, to question some things you’ve been taught, and to consider what it might be like to walk down the road less traveled. I promise it’ll all be worth it. Because there’s no right or wrong way to pursue a work-optional life, only the way that’s best for you.



Before we dig into the financial planning that will make your work-optional life possible, you need to create your vision of what you want that life to look like. Otherwise it’s like driving down the highway without knowing your destination.

Get ready to dream big!


Early Retirement: The Ultimate Life Hack

The cost of a thing is the amount of what I call life which is required to be exchanged for it.


I was the last person anyone would have expected to retire early. A gold star–seeking overachiever on whom the character Lisa Simpson could have been based is not who you think would willingly walk away from a high-powered career and a more-than-comfortable paycheck. I was the straight-A student, the editor of the school paper, the champion mathlete (I might as well disavow you of any notions of coolness right off the bat), the president of nearly every club I joined. (Even chess club. Just in case you wanted to further evaluate my lack of coolness.) My high school yearbook superlative was “most likely to rule the world.” Yes, I was that girl. And I liked being that girl. I liked believing that I was doing everything right, checking all the boxes en route to the eventual work success that would make me feel fully self-actualized and happy. I was ready to throw myself into my career, to change the world, and to find myself in the process. Because that’s how we’re taught it’s supposed to work, right?

Of course, it only took me a short time in the real world to understand that things weren’t going to go how I’d always expected them to. I wasn’t even in my first job yet before mentors were telling me not to follow them down their career paths—from my mentor at my dream internship at National Public Radio to my favorite professor at Berkeley. They were in positions I was positive I would feel proud to achieve one day, and they didn’t seem any happier than the next guy. I was barely out of college when I realized that I could be super successful on paper and even earn loads of money, but work probably wouldn’t ever fulfill me the way I’d hoped. Not that work is bad or something we shouldn’t commit ourselves to, but if you’re not one of the lucky few for whom work is a true calling, it’s okay to aspire to do more in life than work until you die.

We’re taught from our earliest schooling that there’s a way we’re supposed to do things: get good grades, maybe go to college, choose a career path or start a business, collect a steady paycheck, upsize our spending as our pay goes up, and stay at it all until we turn 65. Somewhere in there—the script says—we meet a spouse (or two or three), maybe have some kids, buy some new cars, pick up some hobbies and toys, go on some vacations, and then reward ourselves for all of it by playing golf all day or taking lots of cruises after we’ve punched the clock long enough. It’s never clear when exactly the happiness or fulfillment comes, but it’ll happen, trust us. And most of us play by the rules of the game, even though it’s a fundamentally unwinnable game. No boss has ever said, “I’m promoting you and giving you a raise, and now you can work less.” It’s always more. More responsibility, more pressure, more time spent working, and more intrusion into our lives outside of work. We might get more money, sure, but we earn it the hardest way possible, by trading away our brain space and maybe even our dreams.

There’s good news, though: Life doesn’t have to go that way. There’s an entirely different way to play the game, one that involves a much earlier exit, and it’s time we reset the rules.

What Is Retirement, Anyway?

Retirement is a loaded term, filled with imagery of sitting on a beach with an umbrella drink in your hand, never doing one second of work again. But here’s the thing: That’s not reality for the vast majority of retirees now, nor has it been at any point in history. Retirement itself has only existed since the late 1800s, and even then, very few people actually retired. For most of human history, people have worked until they died, though that work looked almost nothing like the always-reachable, can’t-get-everything-done work of today. Even in the 21st century, with more economic prosperity than ever before and more people retiring than ever before, many people don’t quit working when they retire. According to the Bureau of Labor Statistics, labor force participation for adults aged 65 to 74 is increasing and will hit 32% by 2022, and 11% for those 75 and older.1 Some of those workers are people who never retired, but many more are folks working “second acts,” jobs that are often part-time and that may feel fun or purposeful. Many other retirees are redefining the term by focusing on volunteering and service, giving their retirements meaning but spending their time in ways that look an awful lot like work.

The formal concept of retirement originated in late 19th-century Prussia (now Germany) under Otto von Bismarck, and it was not instituted altruistically to give workers some well-deserved leisure time. Rather, it was put in place to force older, less-efficient workers out to make way for younger, more able-bodied workers. The retirement age was set by the economists at 70, though very few ever reached that age and benefitted from the program. Some pensions were created for military servicemen in the US and public employees like firefighters and teachers in bigger cities between the mid-19th century and early 20th century, and American Express created the first private pension in 1875, but these pensions were not meant to eliminate the need for work altogether. When the Social Security Act of 1935 was passed in the US, the retirement age was set at age 65, but at the time, the life expectancy for an American male at birth was only 58.2 Most of those who reached adulthood could expect to live to age 65, but many workers would never benefit from this new program. It was instituted just after the Great Depression as an incentive for older workers to leave the workforce and make way for younger workers at a time when jobs were scarce.

Contrary to popular belief, there’s also not a “correct time” to retire. Though we think of age 65 as the right retirement age, it was an arbitrary age chosen by economists and actuaries when Social Security was created that happened to make things balance out fiscally, not because there’s anything special about turning 65.3 And in reality, if we look at long-term trends, people are retiring far younger than we used to. In 1900, more than 60% of men 65 or older were still working, a number that dropped to 40% by 1950.4 And by the year 2002, it was down to 17% for men, and 10% for women over 65.5 The average retirement age currently stands at 62,6 though nearly three-quarters of current workers say they plan to work past age 65, and two-thirds say they’ll semiretire and continue to work part-time.7 So there’s no magic to any of the ages we tie to retirement—59½, 62, 65, 67, or 70½—but only functional milestones. There are other ways to fund your retirement that don’t require age-linked investments, and if you build them into your financial plan, there’s no reason why you have to wait for those milestone ages to leave your career.

Bottom line: Retirement is still a very recent invention. It was never intended to be something everyone could do, it certainly wasn’t instituted for the good of workers (us!), and for many people it doesn’t mean the end of work. Retirement is no reason to shape our entire lives in a conventional way on a made-up timeline that says we must work full-time until age 65.

The Freedom to Define Retirement for Yourself

Sociologist Robert S. Weiss defines retirement three different ways: (1) economically, by the fact that you don’t need to work for money; (2) psychologically, by your own determination that you feel retired; and (3) sociologically, according to whether society sees you as retired.8 Unfortunately, we give the last one far too much weight and think it’s up to others to decide whether what we’re doing qualifies as retirement. If you put yourself in a position to walk away from work—whether that’s forever, temporarily, or partially—you can call yourself retired in some form if you darn well feel like it. And after you detach yourself from that arbitrary age 65 and its limiting notions of what retirement means—for example, the false notion that you’re never allowed to earn another cent if you call yourself retired—you open yourself up to an entirely different way of seeing life.

Instead of using our money to buy us more things and treat ourselves to cope with the stress of working—as the standard script tells us we’re supposed to—we can use that money to buy our way out of the standard work system altogether. You can hack your money and your mindset to achieve a work-optional life more quickly than most people imagine possible, reducing the role of mandatory work and increasing the time you can spend on what fulfills you most, from travel to hobbies to service to time with friends and family. Best of all, it’s possible without pinching every penny or living so frugally that you make yourself miserable. Because this is ultimately about living your best life, and that means enjoying yourself both while you’re saving and after you reach your goal.

While you can shape the life you’re aiming for however you wish to, here are the general categories of work-optional living:

Full early retirement—You never need to work for money again. By saving enough that your investments can grow to cover your expenses forever, work becomes entirely optional for the rest of your life. There’s no rule that says you’re never allowed to work again if you feel inspired to do so, but with this approach, you’ll never


  • Forbes, "Best Early Retirement Blogs to Read!"

, "Best Books for FIRE!"

Forbes, "Money and Productivity Books You Should Absolutely Read This Summer!", "Best Money Books By Finance Podcasters"
  • "Tanja Hester and her partner... achieved early financial independence, and in these pages she takes you on her journey. Learn why so many are firing their bosses and searching for meaning and purpose beyond cubicles and 24/7 jobs."—Vicki Robin, New York Times bestselling coauthor of Your Money or Your Life
  • "This isn't just a book about how to retire early. It's a book that proves it's possible to be mindful with your spending, and create a life that aligns with your values and passions-and work can play whatever role you want it to."
    Cait Flanders, bestselling author of The Year of Less
  • "Hester's story is relatable, refreshing, and a pleasure to read. All too often we chase external measures of success without thinking about what we truly want from life. In Work Optional, Hester gives us a roadmap for a less traveled path: living a more purpose-driven life through financial independence."—Kristin Wong, author of Get Money: Live the Life You Want, Not Just the Life You Can Afford
  • "Inspirational, grounded, and thought-provoking, Work Optional cracks open preconceived ideas of what it means to work and what it means to live a fulfilling, purpose-driven life. Go on this adventure to learn not only the practical steps of early retirement, but more importantly, to discern what you truly want out of life. With Hester as your guide... you just might find yourself living a life you never imagined possible."—Elizabeth Willard Thames, author of Meet the Frugalwoods: Achieving Financial Independence Through Simple Living
  • "Ms. Hester get[s] you to think about how you might retire early, forc[ing] you to ponder how you could cut current spending and increase your income, savings and the rates they earn."—The New York Times
  • "Hester is equal parts analytical and encouraging in Work Optional, which helps the reader tear down any misconceptions about what it means to create a life on your terms. This will undoubtedly be a defining handbook for those looking to diverge from society's expectations of a traditional career path."—Erin Lowry, author of Broke Millennial Takes on Investing
  • "Tanja Hester turns [the dream of early retirement] into a reality, by guiding you to map out your own plan for living the good life earlier than you might have originally expected."—Bustle
  • "Work Optional outlines a realistic yet awe-inspiring path to a life where work is optional. There are plenty of books out there about how to save money and build wealth but if you want to weave financial excellence into a life full of adventure, contribution, and meaning - this is the book for you."—Chad Carson, author of Retire Early with Real Estate
  • "Financial independence and early retirement are truly the ultimate life hacks, and in the page-turning book Work Optional, Tanja Hester lays out a concrete path to both define your future and help you get there. This newfound freedom gives you the space to focus on what you want out of life: your projects, passions, community and ultimately your happiness."—Brad Barrett, co-host of the ChooseFI podcast
  • "Financially independent with a bulletproof plan, Tanja gets to the heart of what actually matters in moving forward on your financial journey in Work Optional without resorting to the extremes.... This well-researched book gives you a definitive action plan for creating a life-changing financial position in a two-phased retirement plan that is both realistic and motivating. Tips and tactics abound... in particular... her discussion about healthcare options for those seeking early retirement - a huge area overlooked by many many seeking to make work optional or pursue non-traditional work."—Scott Trench, author of Set for Life: Dominate Life, Money, and the American Dream
  • "Takes a practical approach to this pie-in-the-sky goal [of early retirement], however much one might earn. She outlines procedures for saving for a full early retirement but also for partial retirement or just a career sabbatical for those with fewer financial resources. She walks the reader through every aspect of this planning, from figuring out your true annual budget to where to invest for the greatest likelihood of steady passive income later on."—New York Post
  • "A detailed how-to manual for reorganizing one's life in such a way that leaving the workforce earlier than the traditional age of 65 is entirely manageable....Work Optional will leave you feeling empowered. Hester has left no stone unturned in making your financial plan as bulletproof as possible. It's highly readable and inspiring, too."—
  • On Sale
    Feb 12, 2019
    Page Count
    288 pages
    Hachette Books

    Tanja Hester

    About the Author

    Tanja Hester retired early at 38 without being a natural saver. She is the writer of the award-winning blog Our Next Life, an influencer within the FIRE (financial independence/retire early) movement, a columnist for MarketWatch, and co-host of The Fairer Cents podcast about women and economic equality. She lives in Lake Tahoe, California.

    Learn more about this author