Adventures in Opting Out

A Field Guide to Leading an Intentional Life


By Cait Flanders

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Opt out of expectations and live a more intentional life with this refreshing guide from the national bestselling author of The Year of Less.

We all follow our own path in life. At least, that’s what we’re told. In reality, many of us either do what is expected of us, or follow the invisible but well-worn paths that lead to what is culturally acceptable. For some, those paths are fine — even great. But they leave some of us feeling disconnected from ourselves and what we really want. When that discomfort finally outweighs the fear of trying something new, we’re ready to opt out.

After going through this process many times, Cait Flanders found there is an incredible parallel between taking a different path in life and the psychological work it takes to summit a mountain — especially when you decide to go solo. In Adventures in Opting Out, she offers a trail map to help you with both. As you’ll see, reaching the first viewpoint can be easy — and it offers a glimpse of what you’re walking toward. Climbing to the summit for the full view is worth it. But in the space between those two peaks you will enter a world completely unknown to you, and that is the most difficult part of the path to navigate.

With Flanders’s guidance and advice, drawn from her own journey and stories of others, you’ll have all the encouragement and insight you’ll need to take the path less traveled and create the life you want. Just step up to the trailhead and expect it to be an adventure.



Am I really going to do this? This was the question I had been asking myself for months. The idea seemed impossible when I first came up with it in the spring of 2018, while walking along the historic walls that surround York, England, with my friend Kate. By the time I returned home to Canada that summer, I knew I wanted to try. From there, I attempted to answer some of the other questions and concerns I had. Like, What would my family and friends think? How would this affect my finances? Shouldn’t I be doing “better things” with my money? Would this hurt my chances of finding a partner and being able to maintain a relationship? And what if it doesn’t “work”? I thought I had worked through each one and come up with all the answers I needed to move forward. But when I gave notice at the condo I had been renting for the previous two years, I wasn’t certain it was the right decision. And a month later, when I moved the last of my belongings into the back of my sister’s truck and watched her drive away, I still wondered if I was making a mistake.

It was November 25, 2018, and a relatively warm winter morning in Squamish, British Columbia, Canada. I had woken up early to watch the last sunrise I would ever witness from my balcony. With coffee in hand, I stepped outside, looked past the tops of the trees, and focused my eyes on Mount Garibaldi in the distance—specifically, at its prominently pointy snow-covered tip, better known as Atwell Peak. As a kid, this is exactly how I (and probably most of us) drew mountains: with two slopes—one up, one down—connected by a pointed peak in the middle. A triangle with no base. If it was a winter scene that I was creating, I would add a little squiggly line near the top to represent snow. Of course, as I got older and traveled and explored more, I learned that most mountains look much softer. They have curves and rounded tops, and that was true of many of the other Coast Mountains. But not this one. From a distance, Garibaldi looks like the mountain of kids’ dreams. Not surprisingly, then, Atwell is one of the most recognized peaks in the region, and I’d had the privilege of being able to look at it every day that it wasn’t hidden by cloud coverage. As quickly as the sun began to rise, those clouds rolled back in—which typically signaled that rain or snow was on the way—and the mountaintop I loved was painted over with a brushstroke of gray.

Despite the color of the sky, the temperature stayed warm and precipitation held off all morning, which is all anyone can ask for when one decides to move in the winter—or really any time of year in the Pacific Northwest. Even without the good weather, though, this move was always going to be physically easier than all the ones I’d completed before it, because I was packing up the smallest number of belongings I’d ever owned. In the months before, I had sold things like my bookshelf and lamps, and given away some items to friends who needed them more than I did. After decluttering and getting rid of 75 percent of my belongings a few years earlier, I had almost no attachment to physical objects. A bed, a dresser, and the desk I’d made with my dad the year before were the only pieces of furniture I was keeping, along with a couch I was gifting to him. Those four things, along with six small boxes, my outdoor gear, a wall-length mirror, and a custom painting by my friend Amanda Sandlin, were all my sister and I had to pack up. Months of wondering, worrying, and planning, and the whole move took us only an hour.

What made this one more difficult was the fact that I wasn’t moving into a new home. Instead, I was putting my belongings in storage in my dad’s basement and for an indeterminate amount of time. After five years of being fairly transient, sometimes home for as few as four days per month, I had made the decision to attempt a fully nomadic lifestyle. One where I wouldn’t have a permanent home, but would instead slowly travel full-time and try to create the feeling of home wherever I went.

To start, I booked a one-way ticket to London, England. On the surface, I knew this should’ve been exciting, but I was hesitant to let myself feel that way. Traveling long term sounds fun in theory, but I didn’t make this decision quickly or with blind optimism. I had moved enough times in my life to know how long it could take to feel at home in a new space or to find community in a new city. And although I hadn’t actually been to many countries, I had traveled enough to know how disruptive and unsettling it could be. So, that question I had been grappling with—Am I really going to do this? I didn’t have an answer—or at least I didn’t know how long I could do it. The only thing I knew was that it was going to be hard at times, because doing the opposite of what everyone around you is doing always is. That is a situation I had some experience with.

For most of my life, I had followed in other people’s footsteps, the same way so many of us either do what is expected of us or follow the invisible but well-worn paths that lead to what is culturally “normal.” Despite dreaming of moving to Toronto and launching a career in publishing, after I graduated from college, I followed my parents’ lead and advice and started working for the government in my hometown, Victoria, BC. For the next five years, I stayed in a cycle of working Monday to Friday and drinking and doing drugs with friends on weekends. At some point, I was sold on the idea that renting an apartment by myself and filling it with all-new matching furniture and decor was important, and I used credit to pay for it all. I also “needed” a car, and got a loan to pay for that too.

To an outsider, it might have looked as though I had everything one could imagine a single woman in her twenties wanting. I had ticked all the boxes, climbed the grown-up ladder, and reached what I thought “success” was, all by the young age of twenty-five. This was the path so many of the people in my life were on, or wanted to be on, and they all seemed happy with their choices. I, however, felt trapped—weighed down, both physically and emotionally—by a job I didn’t want, in a place I didn’t want to be, and with habits that left me both hollow and broke. The aha moment or turning point for each of these things was different, ranging from finding myself maxed out financially (the worst point) to recognizing and accepting that I didn’t want alcohol to be part of my life anymore (the most honest and humbling moment). With each one, I got to a place where I knew it was time to change direction and take a new path in life. And then, one by one, I decided to opt out.

First I stopped doing drugs, then I quit drinking, and then I paid off my debt, all in the span of two years. I left the government to work for a financial startup, and then I left the startup and became self-employed. I also moved a number of times (including to Toronto, which turned out not to be the right city for me) until I finally ended up in Squamish in 2016 (very much the right place for me). And whenever I had the money for it, I went on a trip by myself. Each decision scared me, but I slowly learned how to trust my gut, and I followed my curiosity to see where these new paths would take me.

Years later, I’ve opted out of so many things you would think I was used to living differently than everyone around me. But the truth is, the decision to leave Squamish and fully embrace my nomadic lifestyle in 2018 felt like the most difficult one to make. Compared to quitting drinking, which meant walking away from something that was negatively impacting my life, leaving a place I loved made no logical sense. I had been here for only two years. It wasn’t enough time, and yet it was enough time for it to become my home. I had made friends here—good friends, women who had become more like sisters. I was part of the creative community, had joined a volunteer group, and had invested time learning about our local politics and the issues that mattered most as our little town continued to grow. Most of the adventure stories I’ve read or heard about start with the person being deeply unhappy with some part of their life, but that wasn’t the case for me. I had done all the work and created a life I genuinely loved. It had taken a lot for me to get here, so I couldn’t properly explain why I knew I had to leave—at least temporarily. I just knew it was my next step. But with no one in my life to look to as an example, I didn’t know if it was even possible to travel and live this way. Furthermore, I wasn’t just challenging what my family and friends might consider to be an acceptable way of life. This time, I was challenging my own thoughts and opinions—stories I had grown up hearing and came to believe about people who “couldn’t settle down,” as well as the theory that travelers would “have to figure things out eventually.”

After my sister pulled away with her truck, I finished cleaning the condo and completed my walk-through inspection. But even when I handed over the keys to my landlord, I still knew I wasn’t fully ready to say goodbye to this place, this town, this life I had made for myself. I was afraid of what I was walking away from. Scared I’d miss out on something that could happen, or that my relationships with the people here would change while I was gone. And unsure if now really was the right time. These were the same concerns I had before I stopped doing drugs, quit drinking, left jobs, started to work for myself, moved to new cities, moved again, traveled solo, traveled more, and even tried things as simple as removing certain foods from my diet and ditching various social media platforms. There is a cost to staying on one path, especially if it doesn’t feel like the one you should be on. But there is also a cost to walking away and venturing into the unknown. The real question that was embedded in each one of my concerns was, What price am I willing to pay?

I didn’t have the answers. I didn’t know if it would work (or what “work” even meant, in the case of giving up my home to travel long term) or if I would be happy about my decision later. All I knew was that I was following my curiosity. My excitement about the possibilities finally weighed just a little more than my fears. It wasn’t going to be easy, but I had prepared as best as I could, and now it was time to go. I was going to do this.

As I walked out to my car and looked back up at the mountains, I finally had the clarity to see that this wasn’t just a decision. It was a mindset I had developed, and a process I had experienced through all of my adventures in opting out.


“Did you lose anyone along the way?” This is the question that first sparked the idea for this book. If I had been asked only once or twice, it probably wouldn’t have registered as important or a topic potentially worth writing about. After my first book, The Year of Less, was released in 2018, I did more than one hundred interviews in the first few months, along with nearly twenty promotional events. Most interviewers wanted to know what the people in my life had thought about the experiment I had written about—a yearlong shopping ban during which I also decluttered and donated the majority of my belongings. But in that book I also wrote about the early days of my sobriety, as well as what I had learned about my consumption tendencies overall. And at every event, at least one person asked a question along the lines of that first one: What did your family say? How did your social life change? Did you lose any friends?

After the fifth or sixth event, I spotted the trend and also recognized that I didn’t like my initial answer. It wasn’t dishonest. I shared the truth, which was that some of my relationships changed that year. But I was withholding the full truth, which was that I absolutely did lose a few people along the way. Of course I did. You will always leave someone or something behind when you decide to change paths in life. It didn’t feel good to say that at later events. It was a more complicated response, but it was the most honest one I could give. Because the answers to questions about how to manage the ups and downs of trying to change your life are never as simple as you want them to be—not even when you’re doing what’s right for you. Especially when you’re doing what’s right for you.

There is a line I wrote in my first book that says, “Once you see the truth you can’t unsee it.” That’s usually one of the things that happens, and it ultimately helps me make a decision to change paths in life. Like when I finally recognized that getting blackout drunk always resulted in me getting into troublesome situations. Or how, after an entire year of budgeting and not being happy with the numbers, I finally understood that my spending habits were holding me back from achieving my financial goals. In each of those examples, I could see the path I was on and where it was leading, and I knew it wasn’t the one I wanted to keep going down. I saw the truth, and the idea that I should make a change was planted.

In this instance, though, spotting the trend in people’s questions helped me see why so many others might be deciding not to change paths in their own lives. It’s not just the fear of losing family or friends—though that’s a very real fear, and one that will probably be actualized early on. (If we’re going to be really honest in this book, we might as well start here.) It’s fear in general. Fear of how you’ll handle social situations, and how you’ll connect with people. Fear of how changing paths will impact other areas of your life, such as your health or finances. Fear that it will be the wrong choice. Fear that you will “fail” or it won’t “work.” Fear of how it will impact your future. Fear of entering the unknown. From what I’ve experienced personally and heard from others, it doesn’t matter if you’re doing something as simple as quitting social media or as complex as moving to a new city or country. When you decide to step off the path you’re on and go down a different one, it’s scary.

It’s especially scary when you don’t have anyone to look to for guidance. By that, I don’t just mean a support network. If you’re open to talking with the people in your life about the change you want to make, you should be able to find at least one person who encourages your choice, even if they haven’t made the same one. The hard part is that: when you don’t have anyone in your life who has made the same choice as you. Who has also quit social media or moved to a new city or country. Who has decided not to drink alcohol anymore or has switched to a vegetarian diet or vegan lifestyle. Who has drastically changed their career or started to work for themselves. Who has decided to be the first person not to join the family business or do what their parents expected of them. Who has moved into an alternative housing situation or attempted to travel long term. Who has opened up a marriage or decided never to get married, or who has even considered one of the many forms of nontraditional relationships. Who has decided not to have kids. Who has gone against what is socially or culturally normal in some way and can openly discuss all the ups and downs with you. Who has actively chosen to brush up against the situations you will face when you decide to hike your own hike, so to speak. And who can tell you if it will work out or not. This last point is especially important, because even if you do find someone who has made a choice similar to yours, you will still have different experiences on your individual journeys.

Not only is it scary to go it alone; it’s also scary to put yourself in a situation where you will stand out. To be the first person to attempt to live differently. To dare to want something different at all. And to try and potentially “fail” publicly. You might find that you are met with nothing but kindness and support throughout your own journey, but that hasn’t been my experience. For every person who has been fully enthusiastic about a choice I’ve made, I would say I’ve crossed paths with at least four who were less than understanding. Or who were more than happy to point out the mistakes I’ve made and who have tried to shame me back to my old ways of living (which are really their ways of living, but we’ll get into that later). So I know why it’s scary to risk standing out. The fear of being alone is wired into us. Historically, if you decided to live differently from the way you were raised, your family of origin could literally reject you. This could lead to being isolated and having a difficult time trying to survive in the world. Even though our reality in developed countries isn’t quite as harsh as that today, the fear of being shamed or rejected still stops us from doing so many things—including being true to ourselves.

For any or all of these reasons, we stick to what we know. We continue to go through the motions. We follow the clear paths and play it safe. But deep down, something doesn’t feel right. We don’t always know what it is at first, but it’s there. And we try to ignore it. Consciously or subconsciously, we try to distract our minds and numb our feelings. We might do this by creating the life we think we are supposed to have. Or we work too much, drink or eat too much, shop too much, spend too much time staring into our screens, and so on, so we don’t have to think about the life we are living. We avoid having tough conversations, don’t express ourselves honestly, feel misunderstood or defensive, and watch our relationships grow distant or crumble as a result. We keep ourselves busy and do anything we can to avoid seeing the signs that are trying to point us in a different direction. Which means we are ignoring our truths, and not speaking up for ourselves around others. And it hurts us. It hurts our chances of fully understanding who we are and becoming more ourselves. And it hurts other people’s chances of getting to know us and our chances of connecting with the world in a deep and meaningful way. All because we are too afraid to try.

But therein lies the solution: the word “try.” What if you gave yourself permission to simply try going down the new path? To not pressure yourself to reach a specific goal, which only leads to the conclusion that you will either pass or fail, but to just try something new? What if you gave yourself the grace to stumble and make mistakes? To not have to do something “right” or perfectly, but to face the challenges, see what you’re capable of, and discover who you will be on the other side? What if you let yourself change direction partway through, or change your mind and stop whenever you wanted or needed to? What if you didn’t feel as though you had to stick to this decision for the rest of your life? What if you could go on an adventure in opting out? What if you could know that it will come with risks and uncertainty but also rewards and lessons that could change your life in ways you have never imagined? Does that sound a little less scary?

This is a conversation that’s been missing from the simple/intentional living space, but it’s also one I don’t see people having around lifestyle changes in general. The content is always so focused on how to follow the steps and make the change that it doesn’t address the fact that there are real human beings involved in the process. Human beings who are going to have a very human experience when they decide to do the opposite of what everyone around them is doing. And nobody seems to be comfortable saying the truth, which is that it’s going to be hard. You are going to question your decision and think about giving up. And you are going to lose people along the way. Instead, we throw around overly simplified statements like “Just let go!” and “Say no!” and “Lead by example!” and suggest that then everything will magically get better. In the long term, that can potentially be true. When you know what your values are, it’s certainly easier to make decisions that align with them. But in my experience, it always gets harder and more complicated first. That’s because these aren’t just little changes or challenges with pass or fail grades. You’re starting an adventure in opting out. Opting out from the family stories, expectations, and messages that told you who you should be and how you should live. And opting out from the stories you’ve told yourself about who you thought you should be. It’s not easy to change those stories, or to step off the path you’ve been walking along and take a different one. There are a lot of challenges that come with it. And we are doing a huge disservice by not talking about this, and better preparing one another for the journey we are about to take. That’s why I wrote this book.

Before you flip to the first section, I need you to know two things about me. The first is that I grew up with very strong messaging about how I should live my life. My parents and extended family essentially read us their rule books, as though the way they did things was the way my siblings and I should do things too. My dad had some particularly strong opinions on topics like our careers and money. Other things were passed down through behavior that was modeled for us. And I have to say that none of their messages were necessarily bad. I tried a lot of the things they suggested, or that my friends/coworkers did, and I walked down their paths for a period of time. And I was actually “good” at most of it. I was good at working for the government. I was good at shopping and creating a home that I felt comfortable in and that people wanted to visit. I was good at spending my money in general. I was good at socializing and partying. And I was really good at staying in my hometown and sticking to what I did well.

But I wasn’t happy. Not unhappy, per se, because I don’t always like that word or think happiness is a great way to measure our lives. I wasn’t at peace with my choices—they didn’t feel right, for a number of reasons—and I was ignoring all the signs that were trying to point to this truth. The fact that I was constantly finding myself bored and counting down the hours until I could leave work. Buying a lot of stuff that I would never use because I didn’t know who I really was. Digging myself deeper into debt. Partying too much, and wasting time being hungover or coming down from a high. Overeating and gaining weight. Staying in unhealthy relationships and feeling deeply unworthy. Never getting ahead, or achieving any of the goals or realizing any of the dreams I had. And I was overwhelmed and anxious about something in every area of my life. I was ignoring myself and the voice within that told me I didn’t want this life, that I wanted to live a different way.

Because the messaging in my life had always been so strong, I genuinely didn’t know that it was possible. I didn’t know what a different way of living looked like, or how I could go about making it a reality. I was also afraid to tell people how I was feeling. I was afraid to be honest, because the most honest thing I could say was that I didn’t want to do what anyone else in my life was doing. And I was afraid to say that out loud, partially because I didn’t want to disappoint people or risk hurting their feelings by suggesting that what they were doing was wrong. I also didn’t want to make mistakes and look stupid. More than anything, though, I was scared to be the odd one out. I didn’t like myself very much back then, and I couldn’t handle the thought of being alone in the world. And that fear meant I was subconsciously doing a lot of things I didn’t really want to do, just so I could feel connected to people—even if we were ultimately connecting in all the wrong ways.

I was terrified to tell people about every single one of the changes I have wanted to make in my life. To share that I might even attempt to opt out of something. First, I was scared to tell my parents. Then my extended family. Then my friends. Up until the moment when I shared the idea with them, it was a little fantasy that occupied my mind. I could daydream about what it might be like to take a different path and what I might find as I traveled farther down it. Saying the words made it more real, and left me in the vulnerable position of being subjected to a lot of feedback—most of which I didn’t ask for. Some people have been supportive of the choices I’ve made, but many haven’t. I’ve lost friends. Shifted and ended relationships. And every other fear I’ve had has been actualized, at least once. I’ve made mistakes. Wasted some money. Realized that things weren’t working. Changed my direction or my mind. Probably looked foolish or flaky in a few people’s eyes. And yet I have never regretted trying.

Every adventure in opting out has been worth it, because as soon as I walked away from something that wasn’t working for me, I could finally hear my own voice. I learned something about who I was, what mattered to me, and how I wanted to show up in this world. I learned how to determine what my values were and how to live in alignment with them. I wrote my own rule book. The opt-outs themselves didn’t magically make everything better. Quitting drinking didn’t solve all my problems. Getting out of debt didn’t make me a financial expert. Decluttering on its own didn’t change all my consumption tendencies. You can walk away from something and never look back to learn anything about your relationship to it. The opt-out itself was never the quick fix. Embracing the full adventure of it is what has changed my life.

It helped me quiet the messaging in my head and learn how to listen to myself. It stripped away all my usual coping mechanisms and helped me learn how to navigate the world in a more open and honest way. It taught me how to be a beginner again. It helped me build confidence in myself and trust that I was resilient and could figure out how to deal with any situation I found myself in. It helped me become more self-aware, which is hard but so beneficial for me and everyone I have crossed paths with since. It helped me find causes I am genuinely passionate about and give back in a way that I never did before. It helped me build more intentional and meaningful relationships with people. And it helped me become more myself. Now I get to walk through this world as my full self and live an intentional life according to my own values. And I never could’ve imagined I would get here. Twenty-five-year-old Cait couldn’t have dreamt this up. That doesn’t mean it’s always easy. Living this way means having to be more courageous and vulnerable, and it feels as though I’m stumbling around sometimes. But I’m happy to keep showing up and doing that work, because this way of life keeps leading me in a direction that is so much more fulfilling than where my original path was taking me.

The second thing I need you to know about me is that I wasn’t very adventurous as a kid. Growing up in British Columbia meant growing up in nature’s playground. No matter which direction you looked, there was always at least one element of the landscape that you could turn into an adventure. You could climb boulders and mountains. Ride up and down the countless trails available in each new season. Play hide-and-seek among the ancient giants in our forests. Dip your toes in the turquoise waters of glacier-fed rivers and lakes. Pop over to any one of the thousands of islands and see what it had to offer. Skimboard along the waves as they hit our beaches. And, with the warm protection of a wet suit, get off the coast and into the Pacific Ocean. Super, Natural British Columbia was the province’s slogan for many years, followed by Best Place on Earth. It takes only one look at the coastline, forests, or mountain ranges to see that the province lives up to both.


  • “Opting out isn’t about taking huge risks or being perfect in how you navigate new trails in your life. Cait Flanders's book isn’t a simple how-to full of hacks and tips, it’s more like having a helpful fellow traveler on your journey, one who gently shows you how to critically examine which new paths may be worth exploring. Do yourself a favor and don’t opt out of reading this book.”

    Paul Jarvis, author of Company of One: Why Staying Small Is the Next Big Thing for Business
  • "Through stories and metaphors, Cait Flanders will show you how to opt into an intentional life. The prose reads like a long letter from a good friend. The book is unique and full of wisdom. I highly recommend Adventures in Opting Out!"Tammy Strobel, author of You Can Buy Happiness (and It's Cheap)
  • “I emerged from Adventures in Opting Out feeling courageous. In these pages, Cait Flanders does more than simply inspire us to live with more depth and authenticity. She gives us rare, practical guidance on reaching beyond outworn cultural norms to discover—and to follow—the adventure that is ours alone to create.”—Lyanda Lynn Haupt, author of Mozart's Starling
  • "I always feel better after I read Cait Flanders; there’s something about her mix of practicality and truth-telling that both soothes and inspires me...A sturdy and flexible framework to navigate whatever path you are currently on."—Mary Jo, Powell's
  • "Refreshingly blunt and entirely free from feel-good platitudes….Whether you're in need of a life change these days or not, it's helpful to read words of guidance from someone who works so hard to practice what she preaches about simple, frugal, and intentional living."

    Katherine Martinko, Treehugger

On Sale
Sep 15, 2020
Page Count
272 pages
Little Brown Spark

Cait Flanders

About the Author

Cait Flanders is the author of Wall Street Journal bestseller, The Year of Less. Described by Vogue as “a fascinating look into a living experiment that we can all learn from,” it has been translated into 8 languages, and went on to become one of the most sold nonfiction books on Amazon in July 2018, and one of Powell’s Staff Top Fives that same year. Her story has been shared in the New York Times, The Guardian, The Globe and Mail,, Forbes, and more. Cait always has an adventure in the calendar, and believes in leaving every place better than she found it. She is from Victoria, BC, Canada.

IG: @caitflanders

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