dispatch 027 // week 11, day 1: "Who are you waiting for?"
Hi.
Last I wrote I was three days into an intentional professional pattern break. Ten weeks later I’m still at it: free from the binds of a day job, but also admittedly without the benefits. The space in between has afforded me mornings at the playground with my kid, presence to mourn the passing of beloveds, long coffee dates with people I admire, thoughtful interviews with prospective companies, and the mental space to develop new independent projects.
It has been peaceful. And maddening.
While I had all sorts of theories on how to construct daily & weekly habits, truly the only thing that actually stuck was the practice of drafting my calendar. Every week I sat down with ruler & pen to plot the days ahead. As the week unfolded plans smeared, boxes were checked (or ignored), but the ritual of physically auditing my time kept me sane.
I blame the weather. Summer is a terrible time to implement a new regimen, literally everyone else is indulging and breaking their routines. Who wants to stick to a plan when you can go to the beach?! "Drink some more rosé!" Says basically everyone.
But then the kids went back to school. My kid went back to school! And the humidity finally, mercifully broke. Then pumpkins sprouted up on stoops. Shit.
As I went to construct this week's calendar I confronted the reality that this pattern break has gone on far longer than initially intended without creating any real productive new patterns.
Oh heyyyyyyyyyyy, week eleven.
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Toddlers ask a million questions.
I can’t tell you exactly when this started, but months before she turned three my daughter looked at me and asked, “Papa, who are you waiting for?” Most likely we were curbside waiting for a car, or for the buzzer to announce our dinner guest. There was most definitely a plausible near-term answer to that first inquiry.
But then she started asking when I least expected.
Just hung up from a phone call.
“Who are you waiting for?”
Caught daydreaming at the dinner table.
“Who are you waiting for?”
Riding on my shoulders while we walk down the street silently.
“Who are you waiting for?”
Kid, OMFG. Who am I waiting for?! Why are you constantly asking?!
Except, she's totally right.
And it isn’t a question. It is a call to action.
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Last time I wrote about how my brother and I used a series of monthly dares to prototype collaborating and overcome our penchant for the paralysis of perfectionism.
I realized this weekend that I needed more structure than my handwritten calendar was providing. I needed another framework. Maybe three? And I needed the satisfaction of finishing something while my big projects are, well, developing. It was time to bring back Take the Initiative, but this time fly solo and add some new twists.
The challenge:
I’m giving myself the month of October to make a piece of art inspired by my daughter’s question/motivation: “Who are you waiting for?”
I’ll follow the original TTI guidelines (condensed below):
must be completed in one month
output must be shared with others
process must be documented
PLUS! I’m going to launch a Kickstarter. A Quickstarter Kickstarter!
I’m not the only lover of constructive constraints. Designer Oscar Lhermitte conceived of the Quickstarter creative prompt to inspire more small (fun!) projects. His recommendations include:
plan in three months or less (this craziness is days old)
keep the campaign under 20 days (gonna do 17)
funding goal should be under $1K (sensible)
offer rewards under $50 (accessible)
shoot the video in one day (he said shoot, not cut. phew)
no pr or media outreach, unless contacted (copy)
ALSO! I want to utilize tools that didn’t exist the last time I ran a campaign, so I’m challenging myself to (at least once) broadcast my process via Kickstarter Live.
That’s it. Simple, right?
The campaign should go live this week and with it will come more specifics about the above ambiguous reference to piece of art. For now, let’s say that some knowns are known, some knowns are unknown, and some unknowns are (inherently) unknown.
I’ll give a shout when the campaign goes live, tho you might see it on Insta first.
And since we’re here, I can’t help but want to focus group a bit.
Have you run a crowdfunding campaign in the past 2 years? Yes? Which platform? Why?
Have you donated to a crowdfunding campaign in the past 2 years? Was it for the cause? The person raising? Or the cool new XYZ product being created?
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It feels negligent to send this out without acknowledging the headlines and the trauma they are surfacing (and causing). Grateful & heartbroken for everyone who has raised their voice and for those unable.
At the end of the day, who are any of us waiting for?
We have to take care of ourselves & each other.
And keep amplifying voices.
And please, check your voter registration.
And week eleven, day one, is almost over. Thirty (hopefully) perfectly crisp October days to go.
Talk soon. And turn up the Robyn, Honey.
- kyle
for the curious, a pixelated window into my calendaring madness below.



