Reader Support Circle: Week Two
Is Choosing Freedom Irresponsible?
A Note From Me
Welcome back to another week of our reader support circle. With the amount of emails coming in lately, it’s clear that many of you are standing at crossroads, questioning your paths and the lives you were told you “should” want. I love that we can hold these conversations here.
Every letter I receive reminds me how many of us are quietly yearning for a life that feels more honest, more free, more aligned. So thank you for trusting me with your stories. Let’s dive into this week’s.
LETTER FROM A READER (ANONYMOUS)
Hi Scott,
I’m writing this from an airport. I just finished your book, I Don’t Want To Grow Up, on my flight and felt like I needed to reach out. I’m a recent college grad, and my dream has always been simple: to live free. To travel, take photos, meet people, and explore the world. That’s all I ever wanted since I was young.
But like so many people, I was pushed toward the “responsible” path. Go to college. Get a stable career. Be practical. I studied photography because it felt like the closest thing to freedom, but now that I’ve graduated, I feel torn. My family expects me to chase a high-paying job to justify the degree and the debt, while every part of me still wants to wander, work abroad, live modestly, and pursue the kind of creative life that actually excites me.
Two of my closest friends took the nomadic path—one living in Olympic National Park, the other traveling the world doing seasonal work, environmental projects, whatever feels right. A big part of me wants that too.
Right now, I’m back home, working at a coffee shop, volunteering, reading, writing, and trying to figure out what comes next. I’m drawn to the idea of living overseas—maybe Lisbon, maybe Paris, maybe Ireland. Maybe photography, maybe farm work, maybe something I haven’t discovered yet.
But here’s the fear: would choosing freedom make me irresponsible? Am I letting my family down? Should I follow my heart or the path I’m “supposed” to take?
Your book helped me realize life can be simpler. But I’m still scared of choosing wrong.
Thank you for listening.
—A hopeful traveler
MY RESPONSE
Thank you for reaching out and for sharing a piece of your journey. The fact that you finished my book between flights—mid-transition, suspended between where you’ve been and where you’re going—feels perfectly aligned. That’s exactly where you are right now: in the middle of becoming.
Let me start here: you’re exactly where you’re meant to be. You’re at a doorway, and the clarity inside you—the desire to feel free, to travel, to create, to meet people, to live simply—has been with you long before anyone told you who you’re “supposed” to be.
Here’s a truth most people avoid: you still need to make an income—but you get to be creative with how you do it. Freedom doesn’t mean avoiding work. Freedom means refusing to mortgage your soul in exchange for things don’t matter to you. There are a thousand ways to earn a living that don’t require you to betray your nature. Travel jobs, remote gigs, farm work, photography projects, guiding, environmental work, coffee shops, hostels, writing, art markets—doors appear the moment you step toward the life you actually want.
If you keep your eyes and ears open, you’ll meet people along the way—coworkers, managers, and friends who turn into opportunities. Conversations that point you toward the next job, and the next, and the next… That’s how this works. It’s worked for countless adventurers before you. It will work for you too.
And I say this from experience.
I also majored in photography. Everyone assumed it meant I’d become a photographer. It didn’t. But that degree pointed me toward travel, creativity, curiosity, the wilderness. It eventually led me to writing—my true calling. That’s how it works when you take your passions seriously and follow the breadcrumbs. One fascination leads to another. One job opens the door to the next. Nothing is wasted. Nothing is wrong. The universe conspires to give you exactly what you want. The problem is most people have no clue what they actually want. Fortunately, you do.
Your family is trying to protect you with the only tools they know—stability, certainty, predictability. They’re scared of the unknown. They can’t see what you see. They can’t feel what you feel. And they can’t live your life for you.
Bottom line: Your parents want you to be happy.
Your job right now isn’t to plan the next twenty years. It’s to follow the next breadcrumb. Take the next step that excites you. Make your move. Don’t stall. Set a deadline. Move forward with boldness and purpose.
When you move in the direction of your calling, things begin to shift. The right people appear. Unexpected opportunities surface. Work shows up. the world rearranges itself to support the person you’re becoming.
Time is your most precious currency. Spend it wisely. Keep going. You’re on the right path.
I’m excited for you!
Scott
If you’re new to this blog and haven’t yet read my book I Don’t Want To Grow Up—the book that sparked this whole series—and you feel like you’re standing at your own crossroads, it might be the companion you need.
If you know someone who might benefit from its message, consider passing it along as a holiday gift.
You can get it here:
www.amazon.com/gp/product/1732352267
Want to Send a Letter for Next Week?
If you’d like your story or question to be featured in this weekly(ish) series, use the button below. This space is continually expanding and evolving. I’m grateful you’re here.
Agree 100% with Scott's response. I took a year after high school to work in several different factories to make money to travel. I spent 5 months riding a bicycle and backpacking before heading to college. Decades later, I have kids and grand kids. My goal for my kids is for them to be happy. As Scott says, you need to earn your keep. This can be through a job where you make money, or through barter. Whatever works for you. Part time, full time, you choose. If you want society to provide something for you (i.e. food at the grocery store or restaurant, clothes, etc.), you need to provide something back to society. When you're young is the time to think about your options, mistakes will happen, learn from them, enjoy life, be kind, help others, have fun.
Another great response Scott, particularly loved - “ Freedom doesn’t mean avoiding work. Freedom means refusing to mortgage your soul in exchange for things don’t matter to you.”
And to the wonderful writer, I would say - hi there, I am in the exact same boat as you. Pretty much echoing what Scott has said here and it may sound counterproductive but don’t try to plan the road too much. Set goals of course, but allow yourself to take opportunities that come. You can try things and restart. All experience is good experience!! You either win, or learn something about either the world or yourself. Every decision you are faced with try and make in a way that you get closer to the things and life you enjoy.
And who knows, you might even find eventually you want that stable life, you might not. Either way that is OK. It’s all a game anyway.
I figured out something recently that the meaning of life is just to enjoy the passage of time. And the way you win is by having the most fun (however you define what fun is!). For some people fun is starting at a screen for 40+ hours a week making big bucks. For others that is travelling the world. One of my close friends works on a scrapyard - and he loves it!!! It’s a simple life, but it’s the life he chose and he enjoys it and who should tell him otherwise!
Create the life you want, for you.
Hope this helps, more than happy to take this offline too if I can be of any service :)