On Starting Friction and Aaron Sorkin

Here goes nothing . . . truly. 🤷🏻‍♀️

I sat down to play with Substack the other day, and I got quickly overwhelmed.

From pricing to colors to Stripe integration to what people will think of this new project . . .

No sooner had I scrolled through the settings, I was overcome by creative concerns: wondering if all my ideas for this are pointless drivel or another time-consuming shiny object distracting me from broader tasks of hunting and gathering new revenue until I can properly support my family three+ years into a pandemic that cratered much of my business as I knew it.

How long will I let that be the excuse? I am smart enough to read the room. I know when things are no longer in flow . . . what if I shared my Pivot-in-progress in real-time this time?

The clock is ticking.

Bridge loans to myself — cobbled together from investing accounts — are climbing.

I have three months to recover even a fraction of the corporate revenue that was wiped off the table last month, or else I’ll need to make one (or more) of my three Worst Case Scenario Cash Out Decisions (Pivot, Ch. 4):

1. Get a job again for the first time in twelve years — not that I’m qualified any longer for roles and salaries that would replace my self-employment earnings.

2. Move out of New York City — my soul city. Find a renter for our place, and try to find somewhere with a lower cost of living that still has space for three of us (including husband and doggie)

3. Siphon off funds from my 401(k) — one that’s not nearly robust enough for retirement as is, after only contributing for five years during my last full-time job that feels like eons ago, from ‘06 to ‘11.

Those questions loom larger than I can handle in any one sitting. So I’m back to Substack. At least that has the hope of new beginnings, the seed of potential.

Seeing all those settings . . . the questions they raised . . .

Well, it’s much easier to just shut the computer, so I did.

😬 Starting Friction

Starting friction, the friction that must be overcome to start motion.

—Free Time (Ch. 1)

Today is take two — err, twenty.

Yesterday I got so far as starting a draft of my first post.

Substack gives you a template for your inaugural flag wave: one that quickly overwhelmed me (again), as what I had in mind was nowhere near thorough enough.

Why this? Why now? Share with people what you’re doing, how often you’ll post, how your pricing works. Think of it as a mini personal manifesto.

What kind of community are you looking to build here? You are inviting people to subscribe to your thinking. What kind of space will this be?

Be specific. Readers love clarity. Explain what they should expect: how often will you post? Can they expect certain posts on specific days? What will free subscribers get?

I don’t know!

idontknowidontknowidontknow.

The thought of people paying an annual subscription further exacerbated my hives: what if I don’t last that long? I can barely keep up with my basic responsibilities as is.

(Just today, having neglected to do the laundry this weekend, I Febreezed the armpits of my only remaining clean shirt that’s loose enough to fit without reminding me I’ve been overindulging my coping mechanisms of eating too much popcorn and chocolate.)

Upon reading these first post guidelines (why is the bar so high?!) I quickly scanned my mental archives, comparing my inchoate writing to all the other, more brilliant, more descriptive, more skilled-at-storytelling Substackers I know and subscribe to.

Why me? I’m just another idiot on the Internet. (I know that’s not generous, but neither is my inner critic when frightened).

I did promise myself “no new projects in 2023” when I optimistically turned the corner into the new year.

But then there were rounds of massive tech layoffs. Silicon Valley Bank, in my hometown backyard, collapsed instantly after the fastest bank run in history, left for scraps and a bailout from bigger banks, sending a ripple of fear and reactionary belt-tightening and renewed austerity throughout my primary client base.

Perhaps I could pry open a loophole for losing one’s biggest client¹, thus re-opening an identity and income void, one of those abhorred-by-nature vacuums.

I’ll consider it apropos that I wrote this first post between two magic phone-signal-free stops of the A-Train, where the metal tube zoomed me through an underground vacuum from 125th Street to Columbus Circle (60th Street) in eight timeless-feeling minutes.

Why not fill the business vacuum with imperfect thoughts and real feelings? It does energize me to write and think every day.

“The only productive way to answer ‘What should I do now?’ Is to first tackle the question of ‘Who should I become?’”
—Kevin Kelly

It harkens back to my writing roots: when I was around nine years old, on some days childcare meant accompanying my mom to her landscape architecture office.

One of her friendly colleagues would give me a prompt on the neon-green blinking cursor of the early Apple IIe that said something like, “An alien landed on the earth…” and I’d preoccupy myself (out of the adults’ hair) while clacking on the keyboard imagining the rest of the story.

What I call “Truth While it’s Fresh,” fill-in-the-blanks storytelling prompts are also reminiscent of my early blogging days, when one had to do some heavy lifting to purchase a domain, install Wordpress, and start blogging. Not to mention the chutzpah of believing you had something worth saying to the general Internet-browsing public. Today social media affords us all this advantage, for better and for worse, and even foments the Shiny Should expectation that we must.

I launched my first website, Life After College, in 2005 as a service to recent grads who might be as lost as I was in the world of adulting and full-time work. “No one said it was easy,” taunted my tagline.

Turns out, no one said any life stage or big transition is easy. Duh.

Doh. 🤦🏻‍♀️

(Next time I’ll tell you the origin story behind the title . . . )

This inaugural post goes live on my twelfth anniversary of self-employment, exactly one month after closing out with my biggest client—shattering any remaining hallucination of security—during a year (okay four) when I am personally fulfilled, even as some of my biggest breadwinner fears have materialized.

“All change involves loss,”
—Stephen Grosz in The Examined Life: How We Lose and Find Ourselves
(From the Pivot introduction)

🏁 Today’s Starting Checklist

✅ Wrong colors — check!
✅ Uncertainty about pricing — check!
✅ No real strategy — check!
✅ Willingness to try — check!
✅ Fear of adding another commitment to an already teetering stack of plates — check!
✅ Every “good” reason not to — check!
✅ Stubbornly doing it anyway.

CHECK-CHECK-CHECK.

Onward through the topsy-turvy roller coaster that is running a creative business.

Photo by Jonny Gios on Unsplash

💬 Let’s Say Aaron Sorkin Made Me Do It.

Returning to the barrage of existential Substack questions, I don’t know any of the answers, and yet I do know what is missing from my life.

Freedom in expression, permission not to be perfect, celebrating the shadow sides of self-employment. Giving people a window into one person’s small business work life.

And I do feel compelled to do it behind a paywall, because I’m not interested in what strangers say here. You’re either in the inner circle, or you’re not.

What a fragile ego, Inner Critic says. Yep. Sue me. I’m working on it.

I hope that in sharing the messy parts of running a business you feel a little relief. That we can turn the pressure release valve ever so slightly in the direction of fresh air and freedom.

I want you to know that you are not alone. No matter how heavy you feel, no matter how low things get, no matter how lost you are (or I am), we can do this.

We can rise. Here’s to embracing divine disasters and our collective starter doh.

❤️

“Don't try to guess what it is people want and give it to them.
Don't ask for a show of hands.
Try your best to write what you like, what you think your friends would like and what you think your father would like and then cross your fingers...
The most valuable thing you have is your own voice.”
—Aaron Sorkin

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1. I’m aware that when I say “lose” my biggest clients, there are two sides to that street, and as a business owner I am fully responsible for all of it: every shortcoming, blind spot, missed opportunity, or failed proposal included. Deep down, I know these big shake-ups are usually in everyone’s best interest, no matter how much it stings at the moment. This dance is exactly what I’ll be exploring in this Substack, finding the silver lining in these divine business “disasters.” ☁️🌺🐝🍋🍯🪄✨💖