Why Stepping Outside Your Comfort Zone Is Worth It—Even When It’s Uncomfortable

UPDATED: June 26, 2023
PUBLISHED: May 6, 2016

When you step outside your comfort zone to pursue a new project or a dream, people like to emphasize that you must “enjoy the journey”—it cannot be about the end result, otherwise you will constantly be chasing a satisfaction that will never come. The joy is not in the end; it’s in the striving, the building. So they say.

I have experienced the moments when the striving truly is the joy. I believe it’s totally a thing. But what about the part when the journey feels just plain terrible?

Related: What to Do When You Feel Stuck

When, no matter how hard you are trying to make it, the journey is becoming awful; when the thing you were once joyously building is now crushing you beneath its bricks, when it’s made you doubt yourself more than anything else ever has, and when the chaos of a creative endeavor is just too much.

I wrote about this recently in the first draft of the book I’m building, a book where I interviewed 120 people about a dream they achieved:

I don’t want to write this book anymore. Hear that, universe?! I DON’T WANT TO WRITE THIS BOOK!!! And yet here I am, writing it. Mostly just so I have something to tell all those people who kindly ask me how my book is going—all those people I wished I’d never told my dreams to in the first place because now I just feel like an idiot.

OK, dream tip No. 1: Don’t tell people your dreams—OK? Just DON’T DO IT! Because people get excited about this. It creates an opening, an energy, a potential for something new to happen, and people kind of love that, especially when they really love you and your failure doesn’t make them feel better about themselves. Weirdly, there are people who do want you to succeed. It’s crazy but true.

At some point, though, I regret telling those people my dream of writing this book, because every time they ask, with all love and support, I just want to crawl into a hole and die and wish I never tried this in the first place. Why did I not take a normal route, one that people wouldn’t ask about because it was boring? I want to be boring!

The amount of times I’ve tried to give up on my dream has really astounded me. I’ve applied for so many jobs and graduate programs over the past two years. Some rejected me. Some I rejected because I realized they weren’t the right thing when the book’s whisper was still stronger than another job’s shout. But I’ve been flailing around trying to find some sense of legitimacy, because somewhere along the way, writing a book felt stupid and I felt stupid for doing it.

I felt irresponsible. And feeling irresponsible is one of the most uncomfortable feelings for a former straight-A-scholarship-winning first-generation student.

How do you continue with a dream when you feel like it’s not practical and you’re a very pragmatic person? I’m a fiercely practical dreamer, and the combination is killing me. I’m trying to find the right balance, but it’s been harder than I could’ve ever imagined.

And then I waste all this time wondering if I should do something more practical when I should just be writing. Just sit in the chair and write. Believe in yourself. So they say.

I think that’s right. But I know from experience that it’s not that simple. And I’m finally feeling brave enough to admit it.

Sitting in the chair and believing in yourself are not always things you can muster each day, especially when you’re still questioning your own talent, ability and worth.

Self-doubt is an ugly thing. Lin-Manuel Miranda, writer of the Hamilton musical, said self-doubt is like rocket fuel, that it can destroy you if you don’t channel it correctly.

Too often I feel like it’s going to destroy me. Then a chorus of a song written by Will Hoge and Eric Paslay rings in my ears: “Keep on dreamin’ even if it breaks your heart.”

But why, though? I wonder. Why should I keep dreaming if it has broken my heart in every way possible, in ways I never even knew were possible, in ways that never would have happened if I’d never stepped outside the norm, if I’d never gone for it?

Go for your dreams! Believe in yourself! Step outside your comfort zone! we’re told. As if it’s all fun and pump-up-music magic. Enjoy the journey! The journey is the best part!

As if it won’t break your heart. As if it won’t make you more uncomfortable than you’ve ever been in your life. As if the journey doesn’t include a million wrong turns, trips into thorny bushes, days and nights stuck in quicksand, lost in the woods without a maps app or cell service.

And maybe for some people, the journey is all fun, all straightforward. I don’t know.

I don’t know. I don’t know. I don’t know. I don’t know.

Want to know the worst thing for a straight-A student to feel about a path? Yup. You guessed it: a sense of “I don’t know.” Ambiguity. Uncertainty.

Until about two years ago, I did things for which I generally knew what the outcome would be. I had a nice shiny syllabus and later a job description that told me exactly what I needed to do: when I needed to show up and what I needed to spend my time doing in order to get an A or a salary.

And for the past few years, I’ve ventured into a place where there is no syllabus, no deadline, no boss, no A and no salary. There are times it has been as exhilarating and freeing as you could imagine. The first year was thrilling. Amazing. The journey, the journey, the journey! It was epic.

Related: Fake It and 5 Other Ways to Conquer Self-Doubt 

But the second year has been excruciating, all quicksand and uncertainty and “I don’t knows.” The second year has me longing for a syllabus, a deadline, a boss, an A, a steady salary.

Once you get to the end of a particular journey, it can be easy to look back and be grateful for the risks and the missteps and the thorny brambles that led you here. But what about when you’re trapped in the flipping bush and bleeding all over the place with no help in sight and feel like you should never have ventured into this unknown path in the first place?

What about the moment when you’re lost in the woods and you really don’t know if it will be worth it? When every day feels like Groundhog Day, an endless Taylor Swift chorus loop: Are we out of the woods yet are we out of the woods yet are we out of the woods yet are we out of the woods?!

But the worst thought is this: What if going into the woods in the first place was just a bad idea? The truth is I don’t know yet. I don’t know.

All I can hope is that the ability to push through the incredible discomfort of I don’t know, of the middle of the story, will be a good ability to have. An artist’s superpower that will aid me in the next thing, even if the first thing doesn’t work out the way I might hope.

I don’t have that superpower yet, that’s for sure.

But I’m trying.

Scratch that.

It’s being beaten into me.

I’ve been screaming and crying the whole way. It has not been pretty. It would be a lie to say I’ve taken it gracefully. I’ve flailed the whole way.

It’s hard when you invest just enough in a thing to feel shame, embarrassment and heartbreak at the prospect of it not working out—and those three little tricksters seem to come just at the moment when it feels like turning back would only feed them even more. And then you realize that even if you wanted to go back, somehow in all the thrill and excitement of the beginning, you forgot to drop breadcrumbs. Maybe that’s the point of no return. The point where you don’t even remember the way back to where you started.

Maybe that’s a good thing. All I can hope is that it will lead somewhere interesting. Interesting is the thing. Because I can say this: I’m not bored.

That’s really the only thing keeping me going in this moment, the only thing that keeps me saying “no” to the alternatives and keeps me writing this book that still seems so uncertain; everything else just seems boring in comparison to the challenge. Chaos is painful, but it’s not boring.

So I’m going with interesting. I’m going with the outskirts of the comfort zone. Even if it breaks my heart.


Epilogue: I’m sitting in a small red chair at The Writer’s Block Bookshop. I just wrote the last lines of this article, and this chorus is singing to me over and over again in this little independent bookstore, bouncing off the paperbacks:

I don’t know where you’re going and I don’t know why, but listen to your heart…

I notice that nowhere in the song does it say the heart has to be whole when you’re listening. Maybe sometimes a broken one will do just fine.

Related: When You Aim High, You Set Yourself Up to Fall Far—Here’s Why It’s Worth It

Isa Adney is an author and TV host named by GOOD magazine as one of the Top 100 People Moving the World Forward. She is currently writing a book about dreams. Follow her on Twitter or learn more at IsaAdney.com.