Hello, I'd like to talk to you about your wild, audacious, unreasonable dream.
An essay on the gift of responding with possibility.
Last month I hosted another Dinner With Strangers in Vancouver, which is exactly what you think it is: eight people who don’t know each other get together for a meal. No one is allowed to say what they do for work, and, after hosting 25 of these and counting, I can promise that something magical happens every single time. Of the many magical things that happened at this dinner, there was one particular moment that I can’t stop thinking about: All night, it was clear to me that one of the guests, who we’ll call Andrea, was working through something difficult in her life. Slowly throughout dinner, she alluded to some of the challenges she’s been facing, some of the questions she’s processing, delicately sharing the decisions on her proverbial plate right now. No matter how “light” I thought the question I was asking the group was (ie. starting the night with, “what’s been the best part of the last week for you?” which I highly recommend adding to your question repertoire), Andrea seemed bewildered and flustered to come up with an answer.
My final question of the evening was, “What’s something you’re looking forward to?” and was surprised to find Andrea leap to answer first, excitedly and declaratively saying, “I’m going to bike across Canada this summer!” The group immediately responded with inspired enthusiasm: “That’s incredible!” “How COOL!” “You are so badass!” “What an exciting thing!!!” “How impressive!” Andrea seemed shocked at the group’s easy acceptance of her plan. “You don’t think it’s crazy?” people jumped in with stories of friends and relatives who’ve done long distance rides (a brother-in-law biking from Portland to Maine! Bike clubs across the country who run annual long-distance rides to raise money for charity! A friend of mine who did a whole cross-country music tour on a bike, guitar and synth strapped to his back!) Andrea, baffled, said, “My entire family thinks I’m nuts. My brother is so worried about me. My partner told me I’m going to humiliate myself.” We were all, frankly, aghast at these responses; sure, there is risk, there is danger, it is indeed an incredible feat to bike across the second largest country in the world. But there are many ways to go about it, and so many ways to find support in order to get prepared. We spent another forty minutes basically crowd-sourcing different people she could talk to, different platforms to figure out where to stay, along with each of us volunteering friends, cousins, aunts, college friends scattered across the country who would be thrilled to take her in for a hot shower and a meal and a place to sleep along her journey.
The world needs all sorts of people, including those that assess risk and show care in the form of worry and plan greatly and survey something from all sides before jumping in. It will probably shock you zero percent that I am not one of those people — I hiked 900kms across Spain without even buying a guide book… I invite complete strangers into my home for dinner… I moved to Toronto at 19 with $400 in my bank account…. it’s one way to live a life, that’s for sure — and I for one am incredibly grateful for the more levelheaded people in my life that slow my roll and help me make more informed decisions and have kept me from blowing up my life. But if someone is brave enough to share an idea that they are excited about, let alone if that idea seems to have sparked something in them, ignited a part that feels big and brave and brings them out of their comfort zone, may we all commit to not telling that person all the reasons why their idea is stupid, why it’s foolhardy, why it won’t work.
When I was in San Francisco, working a very real job (read: one with a salary and vacation days and healthcare and a work email), I felt like my soul died. The dream of this dinner series was chattering away at me, and I so desperately wanted to answer its call. My boyfriend at the time, and his family, I think thought it came off as ungrateful that I was so miserable at this executive job; I after all had very little (okay, no) work experience, and had somehow managed a pretty sweet salary working for a pretty impressive and influential Bay Area founder/ investor/ business guy. On more than one occasion, my boyfriend’s mom said to me, “No one gets to do what they love - you have to make do with what’s in front of you.” Four years later, as I sit here at 4pm at a coffee shop drinking a very delicious watermelon mint iced tea with no salary and no healthcare writing a newsletter that is sharing a story about my 25th dinner while my agent pitches my first manuscript to publishers, I can tell you that what I needed to hear in that season was, “If this is your dream, Jess, then let’s find a way to make it happen. Where do we begin?”
Let me be the first to say it: if a dream comes to you, the kind that makes you catch your breath and say to yourself, “What if it COULD happen?” and if you share that wild, audacious dream with the people in your life and they tell you to be reasonable and to stop being ridiculous, tell someone else. Find the person that is going to say, “I believe in you. How do we make it happen?”
And if you don’t have anyone in your life who will respond like that, I’d like to be the friend you call when you want to talk about your unreasonable dream. I want you to say the audacious thing out loud. Lay out the foolhardy plan, the map you sketched in pencil, scribbled notes, buried handwriting, tell me every half-baked detail, the thing you think about in the company of your mind when you’re brushing your teeth, or when you’re at your job that is going well and you should be so grateful that you’re employed, or around the table you should be so thankful you’re sitting at. Spare me nothing. I want to hear it all.
I am not the friend you call when you need to be brought down to earth. I will not ask you to consider the facts. I will not remind you how good you have it. I will not tell you that everyone has to do things they don’t like. I will not tell you that you may look like a fool. I will not survey the risks beyond pointing out that keeping a lid on the things that make your entire being feel electric and smothering the spark that makes you feel alive is a terrible risk too.
I will tell you a hundred stories of people I love who have gone after their dreams - Annie used to a coffee shop (her first dream at 22, everyone thought she was crazy for that one too) and now she arranges gorgeous flower arches and billowing bouquets for weddings. Lauren woke up one day and decided she was going to start a funk band to play at weddings and paid for her whole downpayment for her house in cash. Brian was an engineer and now he’s a graphic designer, but he will tell you that at 23 he stumbled on a pamphlet for film school that felt like holding whatever the center of the universe is made of in his hands; he never told a soul because he knew what they would say and instead threw out the pamphlet, and never thought about it again. Now he’s thirty-seven and his career is slowly, slowly winding towards film sets. and this isn’t to say that whatever ignites you has to have something to do with your job; I can tell you about friends who have planned wild sojourns, or for whom it felt daring for them to simply move out of their hometown. A friend recently signed up for hip hop classes on Wednesday nights and feels wild and silly and awkward and loves every minute of it. Online dating might be the next great frontier for you, or therapy, or pottery class. All of it is beautiful if it sets your heart on fire.
May we be worthy witnesses of each other’s dreams. May we be quick to believe in the possibility of anything daring, wild, and electric. May we be brave enough to pay attention to what sets our hearts on fire, and brave enough to go after it.
Ways to connect this month
The Collective Conversation: What To Make Of A Faith Practice
Tuesday, April 18th at 7pm EST on Zoom
A conversation I am excited and very nervous to host! Let’s talk about the spiritual upbringing of your childhood, where you’re at with spirituality, what you’ve kept, what you’ve gotten rid of, what you’re missing, what you’re looking for in your spiritual life… it’ll be achy and messy and hopefully inspiring! Register here.
Introducing In Good Company - a monthly writing group
Sunday, April 23rd at 10am EST
I’m thrilled to announce this new offering - gather for a guided writing prompt, share your work and receive feedback on your writing. This is for all paid Substack subscribers (you can manage your subscription in the top right drop-down menu).
Poetry Club - Poems on Deconstruction & Spirituality
Tuesday, April 25th at 7pm EST
Share poems you’ve written or poems you love - the world’s most relaxed club there ever was! Register here (this event is included for paid Substack subscribers).
Thank you for your continued support of this space - it’s allowed me to explore and expand my writing, offer more ways for us all to gather, and right now is alleviating my work schedule so I can concentrate on edits for my upcoming essay collection.
xo jess.
This is the best. "I will not survey the risks beyond pointing out that keeping a lid on the things that make your entire being feel electric and smothering the spark that makes you feel alive is a terrible risk too." Amen.
This just made my heart sing.