How to dream bigger
bigger bigger bigger BIGGER!
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Last week we talked about dreams come true. This week I want to talk about dreaming those dreams, which isn’t as easy as it sounds.
In 2013, my dear friend Adia and I were in our early twenties and were trying to dream. We were both in a kind of post-college stasis, living together at my parents house, literally spinning a globe to try to figure out where we should live, what we should do next. The world felt terrifyingly, thrillingly open, and we wanted to have a run at it. But when we’d voice our ambitions aloud to each other, we noticed we always tended to scale them down to something manageable, not too ostentatious.
Instead of saying, “I want to be an author of bestselling books,” I would say “I want to self-publish a book.” Instead of saying “I want to have a story on This American Life,” Adia would say, “I want to do a story for a local radio station.”
Our downscaling was a reflex shaped by a culture that conditions women not to take up too much space, not to get too big for our britches, to be modest and deferential. And like many people, regardless of gender, we’d experienced being mocked or doubted when we shared our dreams, so we learned to keep our wildest, most out-there dreams hidden, sometimes even from ourselves.
That pissed us off, so we created a new method to help ourselves and each other dream bigger. We got a white board and divided it in half, one side for me, one for Adia. At the top we wrote BIG DREAMS.

I told Adia my dreams, and before she’d write anything on the board for me, she had to push me as far as my dream could go, call me out if I was hedging, minimizing, being dishonest about the scale of my ambition. She got me to admit that I wanted to make screenplays and films, be a sculptor, photographer, “a cool artsy David Sedaris.”
Then it was her turn to dream, and I did the same – helped make sure she was dreaming as big as possible. By the end, we’d said frighteningly ambitious things aloud to each other and survived. We got to hear ourselves declare our dreams aloud, and had a dear friend write those dreams down and say, essentially, “you’re not crazy for dreaming that. It’s totally possible.”
We both found this method of communal, visual dreaming big to be really inspiring and helpful. A ceremony of sorts that showed us the direction of our dreams, a path to follow, words to echo in our subconscious.
Speaking of directions, this is a page from my book, Directions:
Since that first time in 2013, we’ve repeated this dreaming ceremony every few years. One of us will be planning to visit the other and we’ll say, “should we do a dream board while I’m there?” And the other person will be like, “omg, yes, I need that so badly.”
The dream board has become a pillar of our friendship an invaluable record. I have photos of each board saved in a folder and when I flip through them, I see mostly dreams that didn’t come true, failed or fizzled or dissolved or went on their way. But there are always some – pivotally! – that totally did come true.
In the above 2013 dream board, I wrote that I wanted to have my “writing published all over the internet, humor essays, interviews, etc. New Yorker, Atlantic, New York Times. Could mean art/graphic stories as well.” At the time I had almost no bylines. But a few years later, I was indeed published all over the internet! (Except I’ve never been in The Atlantic lol.)
Every single dream always coming true isn’t the point – what matters is that I allowed myself to dream big in all directions. When I look back at all of our dream boards, I feel so proud of my past self for having the gumption and courage to declare my biggest and wildest dreams, and grateful to Adia for doing it with me. She, by the way, did make a story for This American Life, a few years after it appeared on our dream board. Magic is real!! (Her story is great and you should listen to it.)

How do you go about dreaming? Would you try our method at home with a friend? You can use a big piece of paper, a piece of poster board, chalkboard, iPad, whatever! I’d advise hand-writing it vs. typing it out. I think there’s a magic to it.
If you want, drop some of your BIG DREAMS in the comments (ok, so type it here but maybe hand write it for yourself, for magic reasons!) Before you post, ask yourself:
Is anything about this dream being made smaller, more palatable? Am I saying I want to self-fund a short film when I actually want to make a blockbuster hit?
Am I negotiating myself down to a more reasonable dream because I’m embarrassed for anyone to know I want something so grand?
If a genie flew down and would give you exactly what you wanted, are you saying what you’d actually ask her for? (YES, THE GENIE IS A GIRL!)
I’ll go first. Here’s one current big dream of mine:
I want a large, high-ceilinged studio with giant windows and many giant tables for my projects to live on and leafy green trees outside. I want a big sink exclusively for washing paint cups, etc. and a nice bathroom and unlimited shelving and paper storage and a big pink couch and a nice rug! I want it to be separate from our main house, somewhere I can truly disappear into my work and dream my biggest dreams and take up a lot of physical space and make absolutely enormous messes.
Thanks for being here,
❤️ Hal
Notes:
I enabled paid a couple weeks ago, knowing I’d keep the newsletter free but deciding I’d accept help if anyone wanted to chip to help with art supplies – pens, paper, and of course, childcare is an art supply.
I’m so touched that 30 HALMAIL readers went paid. Some thanked me for enabling paid, others thanked me for not paywalling anything, both so sweet and moving 🥲 After running an online shop, I became so allergic to selling anything to my audience, hated feeling like I had a sales job, felt like commerce clouded the messages of my art. This feels different, like a healthy and mutually supportive middle ground, like I’m just playing my guitar in a town square with a tip cup ❤️ Thank you to all of you who read this newsletter.
I need you to look closely at the dream board photo and see that on Adia’s side, it says: “be long term friends with a seal.” I love her!
On my side you may notice it says “fall in love with list person and stay there.” That refers to this list I made of all the things I dreamed of in a partner. The list – it sounds crazy, but it’s true – describes my husband Jack to a T. I met him the following year.





Thank you for this! I love it and identify! My husband and I used to have a “hopes and dreams” for the year date every September. I saved all of our ideas. Now that he has died, I’m learning to dream for myself. I made a 5 year plan, and it gives me hope!
My unfiltered dream is to be a full time creative running an art studio and shop that is managed mainly by someone else so I can focus on making art, teaching classes, creating fun stationary and publishing my best selling memoirs. I live in a city full of flowers and trees and water. I go into the woods to write and eat good food with the person I love. ❤️