Shipping the First Draft
“Perfectionism is the voice of the oppressor … it is the main obstacle between you and a shitty first draft.”
- Anne Lamott, Bird by Bird
Publishing Date: October 7, 2025
The First Draft explores systems, institutions, technology, and the human realities of living inside them. Essays, field notes, and practical frameworks from the intersection of work, identity, and change.
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This essay belongs to the 3 - Leading through change without breaking trust and 7 - Becoming yourself in public pathways.
I spent my Sunday morning sitting in a café I often frequent with my colleagues, chatting with a woman I’ve met a few times before. The morning was cold, clear, and bright - the kind of Calgary morning that reminds me why I’m lucky to live here. I was tired from two long days at a conference, but happy to do what I do best and show up for others. I thrive when I can lift someone else’s load and help them clarify the future.
She told me about her fear - how she was trying to move from zero to one after being pushed out of the company she founded years ago. She felt stuck, unsure of the first few steps, yet she held this vivid image of a house she wanted to build for herself: one filled with vision, love, and purpose.
We talked for two hours. As she spoke, I found myself thinking about my students, their stories, and the patterns I’ve seen over years of ecosystem-building alongside undergraduate students. We talked about showing up for others in human, trauma-informed ways, and the importance of having others to vision-hold for you. And, as often happens, I realized I was giving advice I needed to hear.
We need those who vision-hold for us. People who help organize your thoughts when they feel scattered, who remind you of what you’re capable of, and advocate for you in rooms you cannot enter. I’m lucky to have those people in my life, who pick me up when I can’t find the path and hand me the tools I need at the right time. They encourage me to dream bigger dreams than I can ever imagine on my own.
We talked about the importance of letting yourself dream. If you have the time and space, and don’t need to monetize something right away, sometimes the best thing we can do is dream about the futures we will build, the rooms we will inhabit, and the beautiful things we will birth into existence. Sometimes the most strategic thing we can do is imagine the life and work we want to inhabit before we rush to make it productive.
Eventually, I heard myself: I’ve spent my whole life vision-holding for everyone else - my students, my colleagues, my clients, my friends. I’ve built houses for others to thrive in. It’s now time to build my own.
So here I am, stepping through the door of visibility. This Substack is my shitty first draft - the same advice I’ve given my students for years. I believe in the power of iteration, of starting before you feel ready, and of letting yourself be seen in process.
Thank you for being part of the experiment. I look forward to seeing where this leads us both.
Next Step: A Way to Practice This in Your Life
Vision Holding Circle
Ask one trusted person to hold your vision with you for 10 minutes without interrupting - their job is just to hold the “container” and listen. Speak the future to them as if you’re speaking it into existence. When complete, ask them to reflect back what they’ve heard, and help you uphold that vision in future.
The Shitty First Draft Hour
Set a 60-minute timer and work on only the part that feels the most stuck to you. No editing, no formatting. Evaluate your work and the experience. Repeat as helpful.
House Building Exercise
Write a description of the house you want to inhabit one day as your life or work. Include 3 rooms: craft, community, and future self. Where do you hesitate? Where is the vision crystal clear? Sit with the hestitation - this is where the work lies.
PS: If you want to support this work: restack it, share it, or drop a quick comment. It helps more than you’d think, and it keeps me writing and helping other changemakers. (This one’s public—feel free to send it on.)
Further Reading and Context
I share books and sources here because I think the legacies people work from matter, and because good writing deserves a longer conversation than one essay can hold. Some of these informed this piece directly. Others are invitations to go deeper into the territory it opens. You can browse my full reading list, organized by theme to see the broader intellectual foundation this newsletter draws from.
Some links below are Amazon.ca affiliate links. I also include Chapters Indigo, Kobo, and WorldCat so you can support a Canadian bookseller or find it at your library instead. I earn a small commission if you buy through affiliate links at no extra cost to you.
Brown, Adrienne Maree, Emergent Strategy (2017).
Brown’s focus on fractals, small experiments, and collective care echoes your emphasis on iteration and vision holding. She also cautions against the exhaustion of being the person who continuously holds the vision for everyone else.
Brown, Brene, Rising Strong (2015).
Brown’s framing of vulnerability as clarity, not confession, aligns with this essay’s tone. She offers guardrails for sharing in ways that create connection rather than performance.
Hersey, Tricia, Rest Is Resistance (2022).
A reminder that dreaming is not indulgent. It is a form of liberation and refusal in systems that monetize productivity. Hersey’s lens reinforces the idea that imagining a future is deeply strategic.
hooks, bell, Teaching Community (2003).
Hooks names the emotional labour of supporting others. Her writing offers language for the weight of vision holding and the need for reciprocal care so that leaders do not hollow themselves out in service.
Lamott, Anne, Bird by Bird (1994).
Lamott’s concept of the shitty first draft is foundational in creative work. She normalizes imperfection as a necessary condition for truth-telling and emotional courage. A counterpoint is that not all communities or identities are granted equal safety to write imperfectly. The freedom to draft badly is unequally distributed.
Mohr, Tara, Playing Big (2014).
Mohr discusses the ways women often step into visibility only after extensive self-editing. Her work supports your final move toward public experimentation and naming your own desire.
Palmer, Parker J., Let Your Life Speak (1999).
Palmer argues that vocation is found by listening to our own lives for direction rather than constructing a persona for the world. His framing supports your turn toward building a house for yourself rather than only for others.
Sarasvathy, Saras, Effectuation (2008; second edition 2020).
Effectuation provides structure for zero-to-one moves. Bird in Hand and Affordable Loss principles offer grounded steps for overwhelmed founders or creators who feel stuck at the threshold.