I Dare You To Dream

What's the worst that could happen?

Shannon Ashley
Apr 12, 2019 · 4 min read

If you've ever read Jane Austen' s Emma, or seen one of the many screen adaptations, you might recall something the young and privileged Miss Woodhouse loves to say:

"Stranger things have happened."

And she'd be right... except that at the beginning of the story she uses this phrase to somehow excuse herself from reality. It's not until the end of the book that she quits trying to control the whole world around her and accepts the wonderful world of possibility.

See, it's possibility that allows for unfettered dreaming.

A year ago, I felt truly at the end of my rope. I was sick of going to bed with deep stress about my crumbling job security. It was frightening. My friend in Knoxville kindly offered a free room for me and my daughter and I was petrified that I would have to accept.

I didn’t want to accept that offer because it meant moving... again, and starting over... again.

From my pregnancy until my daughter was two-and-a-half years old, we moved at least 11 times and lived in 4 different states.

I couldn’t stomach another move.

But what a difference a year makes.

Because I was so scared, I felt as if I had little to lose. I already feared losing my job. What could really be worse than that for a single mom?

I decided to dream, and I decided to start doing what I love. I began to write, and from the very start, I told myself that "stranger things have happened."

That was all I needed to believe in my success. Well, my possibility of success. Just the dream that better things might be in store for me as long as I did the work.

I don't know if it was kismet. Maybe I was just randomly lucky. Either way, writing for myself over this past year has simply flowed better than anything else in my life. Early on, I felt like I was finally on the right track.

It was a little bit crazy, honestly.


As I said, it's been about a year since I first began my writing career. And guess what? We didn't have to move. Didn't wind up homeless again. We got by with a little help from good friends and lots of hard work.

And now? My life is headed in such a different direction.

Today, I wrote a story that meant a great deal to me. Then I worked on preparations for my daughter's 5th birthday party.

I also called the hotel where I'll be staying this weekend for a mini vacation and booked a couple of spa services. That's right, I'm spending 2 nights in a 5-star hotel while my daughter is at her dad's.

It's a pretty big deal because it's really my first vacation. And I think it's a great way to reward myself for my first year of reinventing my life.


Months ago, I wrote that I was "writing my future." But I didn't know what that would look like. Hell, I still don't know what it will look like, but so far it's better than I dreamed.

And that's why I'm telling you all of this--not to brag that I'm turning my life around, but to tell you that you deserve to dream big too.

Please, hear me out on this.

I know better than anyone how easy it is to play it safe. I know. I come from generational poverty where we don't dream for anything except maybe a winning lottery ticket.

We sure as hell weren't taught to dream big for ourselves and believe in what we could do.

And I'm not sure who needs to hear this right now, but I imagine a lot of you do. You need to dream. You need to be brave and bold and write what's on your heart without shame. Or do what's on your heart.

No shame.

Shame is for suckers.


Quit telling yourself your dreams are too big. Instead, start telling yourself those dreams are too small. And quit worrying about every little thing.

If you truly want a new life, take at least one step every day to create it. For me, that step is writing. Always writing.

Trust me, dreaming big and acting with courage comes with critics. So. Many. Fucking. Critics.

People who say: I write too much. I write about the wrong things. I write about nothing. I write like shit. I think too highly of myself and my writing. My writing is not my own.

But the truth isn't what matters to certain critics. Some people just want to bring you down for having the sheer audacity to dream big.

Don't listen to them.


If I had listened to everyone who told me that my writing would get me nowhere, I wouldn't be packing my bags for my first getaway since having a child. Or first vacation ever.

Or, to put it another way, I wouldn't be earning enough money with my writing to pay my bills and build up a savings account... had I listened to the naysayers. I could take the next three weeks off and still earn better than any other job I've had.

Even now, I get people trying to tell me to quit what I'm doing. Quit writing. Quit writing about writing. Like it's irresponsible to dream big when I write and even worse to encourage others to do the same.

Call me irresponsible then, because I don't think we're truly living if we aren't dreaming dreams so big they scare us.

At least a little bit.

People say dream big or go home.

Why can't we do both?


The Post-Grad Survival Guide

Medium’s Millennial Work, Money and Life Advice Publication.

Shannon Ashley

Written by

Single mama, full-time writer, ex-vangelical. It's not about being flawless, it's about being honest. Top Writer.

The Post-Grad Survival Guide

Medium’s Millennial Work, Money and Life Advice Publication. We discuss our post-grad blues, successes, failures, and everyday life right here. Featuring topics related to work, relationships, travel, finances, and so much more.

Shannon Ashley

Written by

Single mama, full-time writer, ex-vangelical. It's not about being flawless, it's about being honest. Top Writer.

The Post-Grad Survival Guide

Medium’s Millennial Work, Money and Life Advice Publication. We discuss our post-grad blues, successes, failures, and everyday life right here. Featuring topics related to work, relationships, travel, finances, and so much more.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch

Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore

Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store