Context matters: This season’s theme is Relationship to Self.
I must confess: I have no idea what I’m doing. I recognize that by admitting this upfront, I might lose all credibility before I even get started. Yes, I fear that this is the first and last time I see you before you hit “Unsubscribe”. But these are the creative risks we take in the Studio.
Today, I’m making the bet that 1) you’ll appreciate this piece (and many future pieces, too) and 2) instead of hitting “Unsubscribe”, you’ll click “Share” and invite one friend to join the party. Here goes nothin’!

Hi, Friend!
Welcome to my studio. (If you haven’t already, check out my About page).
This concept has been gestating for months now and I’m preparing to give birth to it. And I think it’s going to be one of the most important containers I’ve created to date. I feel more excited than anything, but there are parts of the project that feel really scary.
What parts, you ask? Ohh I dunno, maybe the part where I’m not a writer? And — and I’m sorry for yelling but — maybe the part where I SIGNED UP TO PUBLISH FULL ESSAYS IN A PUBLIC FORUM ON A REGULAR BASIS??
With that, I’ve decided to dedicate this post to the process of doing things for the first time.
This morning, I was journaling about my self-doubts when something came through my pen and onto the paper:
“When doing something you’ve never done before, you have to do things you’ve never done before.”
Let’s run that back.
To do the thing...
...that you’ve never done before...
...you have to do the things…
....that you’ve never done before.
“SO OBVIOUS”, I wrote, a literary slap to the forehead. It’s so true. I’m attempting to create a high volume of rich think pieces in perpetuity (something that I’ve never done before) and so to be successful at it, I need to write one piece, and then another (the steps required).
I don’t know why it struck me so profoundly today, of all days. It’s not like I haven’t heard and doled out similar advice before:
“Same behavior, same results. Different behavior, different results.”
“You have to do the thing that scares you the most.”
“Creativity lies not in the done but in doing.”
Maybe it’s because up until recently, I’ve lived my life as a risk-averse person. I have valued safety and security above all in my career and in relationships. I clutch my tender heart, afraid to let it break even in the slightest. I squirrel away financial and emotional resources, in case of emergency. A part of me takes pride in being reliable, bordering martyrdom, and I still can’t seem to shake the inner critic telling me to not ruffle feathers or take up too much space. I’ve been a very good, well-behaved girl/employee/citizen.
But now, I’m craving more.
“In order to recover our sense of hope and the courage to create, we must acknowledge and mourn the scars that are blocking us. This process may seem both painstaking and petty, but it is a necessary rite of passage. Just as a teenager must gain autonomy from an overbearing parent, so too an artist must gain autonomy from malignant artistic mentors.”
—From the Artist’s Way
Why the Resistance?
Of course, it feels hard. As an ambitious species, we are trained to be highly critical of beginners. Our expectations are high and our patience runs low. We don’t know which questions to ask, let alone who to ask for help. We tell ourselves that everything we need, we don’t have. Even if logic reassures us that skills develop over time, our uncoordinated bodies are acutely aware of our flailing arms, and the cognitive dissonance becomes a strain.
Of course, there’s going to be inertia. In the startup world from whence I came, they call this part of the business-building process “going from zero-to-one”. It describes an endeavor that requires a significant amount of lift to get the first version off the ground (the good news is that it supposedly gets easier with each iteration). Who signs up to push a giant boulder up an impossibly steep learning curve? The crazy ones.
Of course, we’re going to have fear. We’re afraid because when doing something for the first time, the outcome is wholly uncertain and failure is a daunting and real prospect. We might begin and quickly find ourselves going down a frustrating path. Or maybe we aren’t willing to surrender. We desperately want to control the timeline, to hold onto our identity and image, to orchestrate every step to perfection.
And yet, this is the process.
And this is me, in progress. Standing at the base of Mt. Everest with my Big Friendly Giant boulder. Staring into the eye of my fear with courage and radical acceptance. Then, allowing the juicy, strong flow of creative energy to push me forward, I take my first step into the unknown.
The Practice
Now I turn the brush over to you, friends.
👉 Are you also in the middle of doing something new in your life, like a business idea or a new relationship? Think back to the last time you were terrified to begin. How did you get yourself started? How is it going so far? Any sage advice for me?
Reply to this email or click the button below and let me know, and on Sunday, I’ll send a follow-up newsletter that incorporates your responses along with some of the techniques I’ve been trying out myself.
Committed to the Vision
“Man can learn nothing except by going from the known to the unknown.”
—CLAUDE BERNARD
I could hold onto the fear of the negative outcomes that might happen if I started, but by that logic, couldn’t I also attach to the positive outcomes that might happen if I started? The more I sit with this vision, the more attractive it becomes. Like a magnet, my disparate interests have quickly made their way here, one by one, converging under one home. It has grown into something much bigger than me.
I truly believe that the world needs more safe spaces to heal through relating. I’m determined to hold this space until we take the taboo out of being a human in progress. Why? Because representation matters! If we don’t hear anyone openly talk about being in progress, we think we have to go at it alone, which is simply and tragically UNTRUE.
I created this metaphorical studio to cultivate community and dialogue with people who ask the same questions that I do and are willing to experiment with the answers. I’m committed to my vision for this community, and I cannot wait for my people to find me here. If you’re starting a new chapter, expanding your awareness, questioning the status quo, staring at gaps in your life that may or may not want to be filled, I’m right there with you.
I’ve never done this before, but I’m going to figure it out.
Inspiration Board
A few things to engage your senses…
🎥 I couldn’t take my eyes off of Ira Glass’s endearingly unkempt hair during his keynote at the Notion conference this week. More importantly, I really enjoyed what he had to say on Scaling the Creative Process (kill off most of your stuff, embrace efficiency, there’s a system for making storytelling mechanical).
🎨 Thank you to artist Louis Thomas, who kindly gave me permission to use the photo at the top of this newsletter. Can you imagine having a coffee at his rustic dining table? Check out his portrait work on Instagram and on Etsy. 🙏
🍲 I’m kicking myself for being late to the Alison Roman train but better late than never. Because of her, I’ve been making stews for the first time in my life. Dilly Bean Stew and Spiced Chickpea Stew with Coconut and Turmeric = five stars. ⭐️⭐️⭐️⭐️⭐️
🔉 Listen to David Lynch’s powerful message for Mr. President Putin: “We are a world family, there is no room for this kind of absurdity anymore." 💔
Thank you for stopping by the Studio. Bring a friend with you next time (and help me win my bet against my fear)! I’ll see ya Sunday with all of our crowdsourced techniques in a follow-up advice column. 👋
In light,
Milan
I started to learn Spanish a few months ago after failing Spanish class almost 30 years ago. It's a lot easier than I remember, just a few months of daily lessons have given me confidence I didn't anticipate. I think the important part for me was to not judge the pace of my progress, and to realize that my 7th-grade teacher isn't here to discourage me anymore. (Mrs. Jenner, if you're reading this, I hope you wake up one day to discover you can no longer roll your Rs.")
"Think back to the last time you were terrified to begin. How did you get yourself started?"
I found a great cofounder! We push each other to do the uncomfortable, not-fun things that need to be done (but we have a lot of fun, too :)).