Charting a Course Through a Full, Unhurried Fall

Tarot card featuring seven chalices, with liquid pouring from two upper chalices through three in the middle, and finally into lower ones, set against a pale background with abstract, wavy designs.

Seven of Cups—the challenge of choice; with a bounty of imagination can come choice paralysis; eventually you’ve got to choose something or be stuck in imagination land forever

“If you pull this card, why not take whatever you’re consulting the cards about and come up with an alternative ending where the best possible thing happens, instead of the worst. Instead of imagining an outcome you don’t like, substitute it for one that involves grace, compassion, and power.”—Jessica Dore, Tarot for Change


Updates from the Captain’s (b)Log

reflections on doing meaningful work with a rogueishly piratical refusal to accept the status quo

Drawing the Seven of Cups as I settled in to write this issue is a little ironic. The Seven of Cups is like my kryptonite card. I’ve pulled it before, and it always hits me hard in the feels. One of the truths about being many kinds of nerd is, for me, that I can very easily hem and haw and dither and dally for extended amounts of time.

In the Buddhist psychology schema, I’m primarily a “deluded” type, which means I’m most prone to getting lost in indecision and rumination cycles. Trust me: when I say I’ve got the experience coaching people through uncertainty, I am my own first tester.

It’s why I never promise to “solve” uncertainty for people or to help them “get past” it. Uncertainty is the water we swim in. I’m trying to help folks learn how to swim better.

And sometimes that means making a choice.

As summer turns toward fall, I usually have a kick of “back to school” energy where I want to launch something new or run an open door period for CARE or otherwise pour energy into something expansive.

This year, that energy isn’t coming the same way. I’ve been swirling around the feeling that I should be making use of this season, but ruminating about how. [Thanks, dear inner critic Should-erella, for piping up to try and keep me focused.]

So, thanks to the Seven of Cups reminder, I’m making the choice to not launch anything new this fall. I’m not planning an official open door period for CARE. If you want to join, add your name to the waitlist, and I’ll reach out individually. It’ll be an experiment in how a non-time-bound “launch” works.

Instead, I’ll be focusing on the conferences I’m heading to (see below) and making human connections there. As I often do, I’ll be bringing along some fun interstitial shenanigans to liven up the between session times at these spots. If you’re there, come find me for tarot card pulls and cootie catcher-based Uncertainty Oracle tips.

And join me in making decisions that focus your churning imagination and energy into actions that feel good.


Dispatches from the Helm

a recent concrete highlight from my work that can hopefully help you in yours

I’ve been having some really interesting and nuanced conversations with colleagues about… you guessed it… AI.

A hefty ⅓ of the sessions at the upcoming Museum Computer Network conference (where I’ll be in October) have something to do with AI.

I’ve seen small business owners create policy statements for potential clients about how they do and don’t use AI in their work.

I’ve heard discussions about creating AI policies on podcasts, as well as podcasters stating aloud in episodes how they do and don’t use AI tools.

The students have been discussing it in the Wellesley class I’m currently auditing, The Social Histories of Computing.

It’s all helping me make decisions about my own AI usage that feel ethically aligned with my values and informed by both a savvy AI-using populace and a rightfully indignant anti-AI one.

To that end, I’ll be focusing the upcoming October 1 facilitated session of CARE on the AI choices we (arts related entrepreneurs) make in our businesses, and we’ll be drafting our own AI policy statements. (Reminder, if you’d like to join, add your name to the list, and I’ll get in touch.)

In the meantime, I’ve created this tool that I’ll share here for you all to use.

Ask Yourself Before You Ask AI is a guide and tip sheet on 4 key questions I think we should all be asking ourselves before automatically turning to our AI companion tool of choice.

As with all new tools and technologies, there are helpful uses and harmful uses. Worthwhile efficiencies and problematic elimination of helpful friction. Instead of blindly following a predetermined social narrative of either “you better get on board or you’ll be left behind” or “don’t touch this or it’ll sap your creativity and replace you”, we should all be able to make thoughtful choices that are right for each of us.

I hope this tool helps with that.


Flotsam & Jetsam

one random bit of fun (could be pics of Lila the dog, a recent podcast fun fact, a bit from one of my many strange areas of nerdy interest, or something else)

You may (or may not) recall that I didn’t write an issue in August, because I was on my annual 3-week reading retreat at Moosehead Lake in northern Maine. This year I read 17 books over the three weeks. Some of them heartily enjoyable, but sadly, none of them a 5-star read.

As I do with all my books, I drew little sketches of the book covers for each one, and here’s the final result, as well as my Storygraph wrap up of the stats.

My little book drawings always bring me so much joy!


Small Treasures

a resource recommendation or creative prompt for you

Thanks to the lovely Carolyn Yoo’s hosting, I made a little About Me zine for my business.

If you’re curious about my work, you can download/print/fold one for yourself.

And if you see me at one of my fall conferences, I just might have some extra copies to give out. 😉


Peer Pitch

space to recommend someone else’s thing—maybe yours

No one submitted anything to me this month, but you can submit one for the October issue.


On the Horizon

something coming up next for me that I’m excited to share with you

I’ll be at 4 conferences in the next 6 weeks (😮‍💨). Here’s where you can find me and what you can find me doing.

AASLH/NCPH (American Association for State and Local History/National Council on Public History) in Providence, RI (Sep 16–19):

  • presenting A Revolution in Management: Rethinking Team Dynamics on Sept 17 (4:15-5:30pm) with my SEED Trio colleagues.

  • co-hosting the Independent Museum Professionals meet up on September 17 (6-8pm) at Track 15

  • pulling tarot cards and offering Uncertainty Oracle advice if you come find me

MAAM (the Mid-Atlantic Association of Museums) in New Brunswick, NJ:



Text overlay on a gradient background reads: "Uncertainty Oracle, fortune favors the curious."

MCN (the Museum Computer Network) in Seattle, WA (Oct 21–23):

  • pulling tarot cards and offering Uncertainty Oracle advice if you find me





Brochure cover for the 2026 NEMA Annual Conference titled "Undercurrents: Pushing Against Expectations," held November 4-6, 2026, in Mystic, Connecticut. Features abstract wavy blue and green shapes at the top and the NEMA logo at the bottom.

NEMA (the New England Museum Association) in Mystic, CT (Nov 4–6):

  • presenting Ride the Waves of Uncertainty Without Losing Yourself on Nov 5 (3:45-5:15pm)

    • pulling tarot cards and offering Uncertainty Oracle advice if you find me


I write these updates using Ellipsus, an online platform for collaborative writing. They’ve got a feature that lets you share the revision history of your writing, so here’s this issue’s documentation of my non-AI writing process.

Rachel Ropeik

Rachel Ropeik is an educator, adventurer, facilitator, experience builder, and pirate (🏴‍☠️) who coaches curious people and their organizations to dance with uncertainty and change.

http://www.rachelropeik.com
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Attuning to Uncertainty Like a Pirate