What I Learned From Opting Out in Search of a Better Life

My favorite self-help book isn’t about help, it’s a field guide for finding curiosity & wonder.

Licensed from Adobe Stock // Jacob Lund

People really want to tell me things. You know what you should do? You know what your problem is? Here’s my take…If I were you…It’s as if their desire to dump their litter on my lap is greater than my desire to hear or read it. They rarely get it right because they’re envisioning a whole rather than realizing they have only a sliver, a small part of my life. In absence of a complete picture, they fill in the blanks. They apply color, create depth and shadow — a visual they can hold on to so they can write their prescriptions. Make things neat and tidy.

Not realizing they’re not a doctor or my doctor and I never asked for a prescription. Not realizing their painting is of their own making — rooted in values, experiences, and belief systems that have nothing to do with me.

So, I end up sweeping, mopping, and throwing out other people’s refuse in my bins. I’ve come to realize when you share parts of your life online, you become a receptacle for other people’s unsolicited advice and opinions. It’s a matter of how many bags you’re willing to fill.

Years ago, at Columbia, a teacher spent the first forty-five minutes admonishing our workshop. We were petty children playing professor and she was done with our foolishness. We were proud butchers; our workshopped stories resembled crime scenes with all that red ink. A line writer rolled her eyes at a chapter that would become part of my first book. Family stories are so done, Felicia. In response, I wanted to staple my story to her face. Instead, I stared at her for the remaining two hours with what only can be described as contempt.

Our teacher reminded us the stories for which we were giving feedback reflect one writer’s path, style, and point-of-view. This isn’t about whether or not you like the story or think the writer has any merit. Our role is to shepherd the work, to give feedback that will move the writer forward in alignment with what they’ve created and how they’ve created it. If they’re line writers, we wouldn’t try to force a plot on them or shove grammar rules down their gullet. Our job is to work within the constraints they’ve given us.

It’s not for us to rewrite their narrative to suit our taste and style. Their stories aren’t our stories. We are not their authors.

The teacher’s words remained with me for many years, affecting how I supported my friends’ journeys even if I couldn’t understand the choices they made or why they made them. All I could do was push a hot poker on their back, urging them to keep going and that I would be here to support them without dumping on them my suitcases of issues, problems, years of psychotherapy and judgment.

It’s hard shutting up and not telling people what to do. Cait Flanders, in her exceptional book, Adventures In Opting Out, posits:

“When you decide to take a new path and live differently from most everyone around you, you will find a lot of people encourage you not to…They will push their own stories or fears on you, and encourage you to stay on the “safer” path…They path they’ve walked and understand…The truth is that most people can see only as far for you as they see for themselves.

So the concerns or questions they throw at you are the same ones they would be considering. And if they can’t understand why you want to do it, it’s only because they can’t fathom it for themselves.”

I’ll be blunt — I hate self-help. I’m not discarding the transformative value it can have in people’s lives. I hate it for me because setting aside most of the people writing the books we consume are white, educated, privileged, and able-bodied, they’re selling the idea that if one person can do something, anyone can do something.

What we should be pitching is that change is possible even if that change looks different for every person. It’s why I cringe when I see influencers pitching their exact formula for success. I will show you exactly what I’ve done to make $10,000 a month or my first million-dollar launch so you can too! Conveniently discounting the luck, privileges, connections and other factors most people aren’t privy to. But that’s messy business. Better to sell them on the possibility they could be you.

I used to follow this influencer because I couldn’t quit her. Watching her, I felt an odd mixture of curiosity, envy, revulsion, and awe. Here she was making half a million dollars a year, at twenty-five, with zero work experience. I remember reading the comments on an Instagram post where a woman, who worked three jobs to support her two kids, felt despair because she couldn’t afford this influencer’s $2,000 workshop.

You have to work harder, the influencer said. I found the money and you can too. I wanted to punch this woman in the face. I rarely comment on people’s work because I don’t believe in throwing out my garbage in someone’s space, but I had to tell this woman about her hysterical blindness. While this influencer’s parents financed her dream and gave her the credit card to pay for some nonsensical Tony Robbins seminar, which she now regurgitates for $2,000 a pop, a woman who probably makes $2,000 a month, if that, laments the access and opportunities that never seem to be in her reach.

There exists no one-size-fits-all. No magic framework. No million-dollar solution. No guarantees. No happiness pill.

Trust me, I would’ve overdosed on them.

When I teach people — whether it’s writing or building brands — I show them options. I share a framework that leaves room for them to make it their own. I don’t expect them to write like me or build brands like me because they are not me, and I assure you this is a good thing.

The hardest, and most profound way you can teach someone is by sharing your story and being their guide. You are their compass, map, water bottle, and snacks. You help them dodge bears in the forest and snakes in their camper. You can even offer them the best routes and a GPS, but the journey and the routes they take are purely their own. There are no guarantees other than the probability of change.

Clearly, I won’t be selling out of $10,000 masterminds anytime soon because uncertainty doesn’t convert. Honesty is heresy, a sales page ruined.

This is why I love Cait Flanders’s book. There’s something so plain, potent, and endearing about the work she puts out into the world. Her first book, The Year of Less, chronicled her yearlong journey of reduced consumption in all areas of her life. While I had no interest in replicating her exact path, it made me conscious of the things I own and why I own them. It made me define what enough was. The book was revelatory not because she was hawking her secrets to success (she wasn’t), but because she made it clear this was her way. Take that which you find useful, be inspired by any of it, and discard the rest.

Everyone has to find their way. And if you quit, that’s okay. If you fail, that’s okay because it’s never about the end result. It’s the fact that you embarked on a journey — that’s the transformation. That’s the reward.

Her second book, using a hiking metaphor as the structure and frame, takes us along on her adventure as she decides to opt out of her current life in search of something more. This “more” is a digital nomad — shuttering her home in a small Canadian town and slow-traveling throughout the U.K.

Skeptics will invariably roll their eyes and I GET IT because normally I would be seething, but what’s different about Cait’s story is the fact that it’s not a prescription. She’s not telling you to uproot your life and shack up in Airbnbs across Western Europe. She’s not selling you on the IG lifestyle. Like her first book, she’s showing you what’s possible and outlining precisely how she’s making her opt-out happen by being radically transparent about her process and privilege versus a social media architected transparency. This isn’t vulnerability for sale in hopes of conveying relatability, likability, and long-term sales viability, this is simply a woman telling her story.

This is about Flanders sharing a framework for how to opt out of the life and choices people expect of you to create your own adventure. Hers was through travel. Yours might be running a marathon, quitting booze, or making it through a week without scream-crying into pillows (raises hand). I related deeply to the hiking frame she used, which divided the book into five sections:

The Base: Planning and preparation for the big change. This is about the work you need to get to the trailhead or base of the mountain — from the pragmatic logistics you have to consider to the mindset shifts and calculated risks you’d have to take. It’s about identifying when, why, and what you want to opt out of.

The Viewpoint: This is about that first hit of wonder when you try something new. Flanders shows you how and when to identify the most beautiful views because they’ll remind you why you’re on this journey. She encourages you to start slow and pace yourself — don’t get hurt by moving too fast and furious, or be blinded by the beauty to not know when you might need to turn back.

And that’s what I also find problematic about self-help, so much of it (not all of it, so calm your pants) preaches about fighting past failure, to keep hustling and moving, when sometimes it’s perfectly okay to divert course, change your path altogether, or quit.

The Valley: A valley is the low land between two mountains. While this place will be awash in the lushest of sceneries, you realize every step down now will be a climb later. The valley is where you fumble and get lost. The honeymoon’s over, kittens, and there are obstacles in your way. Flanders shows you how to define your values as a foundation for who you are and how you want to show up in the world, which will help you navigate the backcountry.

When you’re panicking or stuck, use the STOP method: Stop, Think, Observe, Plan, which will help you focus on solutions. Most importantly, this is the time to focus on taking care of yourself while in the dark spaces.

The Slope: This is where the valley ends and the next part of your hike begins. Slopes are the side of a mountain. Some offer easy, gradual climbs. Others are steep motherfuckers, which require REI-level equipment, perseverance, and all the deep breathing and motivational mantras you can muster. This is your final ascent in the journey and it’s often the most exhilarating because you’re this close to the summit. Course changes and adventures occur.

This is the precipice of change and Flanders shows you how to ride it with grace and calm. The slope is also frightening because it’s the point where you the possibility of change is probable. At the slope, it’s okay to lean on people and ask for help. It’s okay to freak out because you’re breaking patterns, stepping out of conventions and norms, and people will doubt you, discourage you or stand in your way.

The Summit: This is the point where everyone’s taking selfies. Everyone is literally high on their accomplishments and breakthroughs. But here’s the thing — the adventure is over, and as Flanders says, “you’re at the point where you can simply say, “I am.”’ This is key because it juts up against how self-help positions how endings look and feel like. It might not be dramatic and illuminating or rewarding. You wanted change and this is the one guarantee — you’ve changed.

Change is the reward. And life continues, ebbs, and flows and there will be piles of other heartbreak, joys, challenges, and new mountains to climb along the way.

It’s not that I want a pile of money or to be a bestselling author, it’s more like I want to live differently. I want real, sweeping, beautiful change and Flanders gives me a realistic, honest framework to navigate through it.

This weekend, I held my first two books in my hands and wept because they’re dark. Literally. Look at the covers. In my first book I couldn’t see the sky, and, in my second, I was wading through the dark.

Wouldn’t it be wonderful to light candles, string up lights, and be blinded by the sun, its heat and sheen, enough to write about it? To have made it out on the other side. This is what bolts me out of bed, what I strive for, living as honestly and differently as I can, but being realistic about it.