Optionality’s office hours next week are open to all. We’re doing an AI Show & Tell…showing specific ways we’ve used AI tools to expand and enhance our wisdom, agency, capacity…and I’ll show a couple of epic fails too! Join us here on Wednesday the 13th at 12PM PT.

File it under “If I knew then…”

Nearly 20 years ago now, after BlogHer secured our first round of funding, that also meant we hired our first full-time employees. There were a few other firsts that ensued (besides first paycheck, thank God!): First big conference with a dedicated organizer. First board and therefore board meetings. And therefore first time we were answering to anyone other than our customers.

After that first conference post-funding, an employee came to us and shared there had been an error made. I honestly no longer remember what that error was, but I remember very clearly that it was going to chop $57K off the bottom line numbers we had projected and shared with our board. And this was early enough in our company’s life that $57K seemed like a lot.

On the plus side, the staffer felt safe coming to me and fessing up on the error. They didn’t bury the problem, they excavated it.

Not so plus was that we felt this incredible pressure to recoup and offset this $57K. Unlike our employee, we really didn’t look forward to explaining what happened to our new “boss” (the board) and instead figured out a way to offset the loss, so it wasn’t worth surfacing. (Since, obviously that error was NEVER EVER going to happen again.)

I used to have a presentation I gave to entrepreneurial groups about what makes a good and healthy founding team (based on my experience being part of one), and one of my criteria was that you are able to have the tough conversations, not just the fun ones. And that includes surfacing mistakes. ASAP.

No one is saying it’s fun, but when we think we should keep quiet about it for a little while, so we can fix it before anyone needs to know…well, I can promise you: We probably can’t fix it, the issue will probably get only worse while we try to handle it alone in the dark, and that conversation will be even less fun.

Presumably we are partners with people because we think they’re super smart, right? So, as the saying goes, two heads (or three as it was for me then) are better than one. Getting those big, insightful, trusted brains on the problem makes all the sense in the world.

PS If I’d known then just how often projections and predictions and forecasts are off, and how many ways there are to mitigate that outcome…up to and including simply saying, welp. our margin was 46% instead of 50%. Here’s why. And here’s what we’re going to do about it…well, we might have handled it differently. But it all turned out OK in the end.

So, I kicked off Season 2 in my Buffy re-watch this week, and the Life Lesson to be found in the opening episode of the season seems to be all about not trying to go it alone (or protect people by keeping them in the dark). Don’t bury the hard stuff…hiding it from others, or even hiding it from your consciousness.

Good lesson, made me think of the long-ago story above.

The second episode, however, seemed to instead remind us that sometimes we have to let go. And if something or someone is truly gone, we may be self-sabotaging when we can’t let go. When we hang on with desperation. We we keep digging up something that should be laid squarely to rest in the past.

How often post-break-up, for example, have we known deep in our guts that it was going to eventually fail…we just put off that inevitable, even when we could see it down the road. Or maybe we just wanted to be the one who controlled the failure? How often have we known that about jobs, for that matter?

Therein lies the real Life Lesson, one that recurs throughout the seven seasons of Buffy:

Things are rarely black and white, even in a land of monsters and vampires. Discernment makes all the difference, including discernment about when to bring something into the light of day. And when to let something go and even let it stay buried. I happen to think discernment is an unsung attribute, especially in the workplace. According to a quick search I did, the word is found in very few job descriptions. Descriptions might reference decision-making. Or critical thinking. But too often they use a bunch of words and outline specific scenarios, when what is really required is discernment.

Season 2, Episode 2 is an homage to Frankenstein, if you’re into that sort of thing!

Am I really asking you to “bury” things?

Not really, but sometimes superficial definitions of authenticity and transparency take away your agency to have boundaries. And superficial definitions of vulnerability lead to overburdening those more vulnerable than us.

Last week longtime friend and colleague Morra Aarons-Mele posted on LInkedIn about “authenticity,” and it prompted me to think of another thing I used to say all the time, often when presenting to would-be social media users, especially those that worked for or represented brands:

“To be authentic “everything you say should be true, but you don’t have to say everything that is true.”

In a time when the employment pendulum seems to swing wildly between “bring your whole self to work,” and “your identity (and the lived experiences of our workforce) shouldn’t matter at all,” maybe discernment tells us something else entirely.

Do you have a set of internal guidelines about what you share and what you hold close? Do you struggle more with being able to let us others in or let others go?

So, what Buffy episodes did I watch this week?

I watched Season 2, episodes 1 (When She Was Bad live recap) and 2 (Some Assembly Required live recap)…which aired on September 15 and 22nd, 1997, respectively. These are the first two episodes of Buffy’s first full season, the much-lauded Season 2. The season where people got really addicted, and where conventional wisdom say the show found its footing.

The core #BuffyLifeLesson in Season 2, Episode 1 is that burying your needs and going it alone isn't the best way to solve a problem solved. Buffy is clearly traumatized by her experiences at the end of Season 1, but tries to bury it, to play it off like she’s tough, all’s good, no worries. She also turns her protective instinct (colored by guilt) into an instinct to leave everyone else out of it…to “protect” them. I’ve seen this happen in business so often. A mistake gets made, and the instinct is to try to fix it quickly, so before anyone else knows about it, you’ve already “handled” it. But most of us are not Olivia Pope. Getting out in front of an error and making it a team effort to fix, compensate for, or correct it is usually a way better strategy than trying to bury it.

The core #BuffyLifeLesson in Season 2, Episode 2 is that letting go is hard. In monster-as-metaphor fashion, this episode is a Frankenstein homage, and it’s a metaphor about letting go and knowing when letting something stay buried is actually the right call. It’s such an interesting contrast to the “don’t bury things” message of the season opener. It’s a creepy, horror-tinged episode, but in the end it’s sad too. Because even when letting go is the right thing to do, it can still be hard.

This Week-ish signposting and sharing

  1. Something to dig in on: I read Frankenstein last year and was so annoyed with the whiny, cowardly Dr. Frankenstein character that I found it hard to get through it. The Creature’s monolog’s though, were worth the price of admission. Poignant, eloquent, relevant. You can go to SparkNotes and check out Chapters 10, 17, and 24 to read some of it and see analysis.

  2. Over on Optionality: Jory explores her experience realizing her “scripts” for defining success were written by others, perhaps by society, but didn’t really fit her anymore. She’s writing New Scripts for herself now.

  3. New Book recommendation #1: My friend Becky Mollenkamp’s new book, Liberate Your Business is all about rewriting your scripts to do business in a way that aligns with your values. It’s a great read full of practical ways to take your next liberator step.

  4. New Book recommendation #2 (plus older book recommendation): Another book coming out this month that I’m lucky enough to have an early copy of is Incorruptible by Eric Ries (he of Lean Start-up fame). If you read Enshittification by Cory Doctorow, Incorruptible may represent the antidote. Eric makes the point that enshittification is not inevitable, but that it represents a flaw in the design of the company itself. If there’s a common theme amongst these books and Jory’s post, it’s that going with the flow in today’s business environment, sticking to the script, will lead you down the great to good to enshittified path. Avoiding that path must be an intentional value you set from the outset. It’s super hard to tear yourself away from that path once you’re a certain distance down it.

  5. Other reading recommendation: Full disclosure that Michele Moreland is a client and friend, but she’s been writing up a storm on ethical AI over on the newsletter platform that shall not be named, and she is bringing up so many good points. She’s coming from a place of building an AI-based company, but trying to do it with a company design that sidesteps enshittificaiton. I find the pieces she’s publishing super interesting; they always create a jumping off point for me for deeper thought on the AI conundrum in which we all find ourselves, whether we’re using AI or not.

  6. If you’re into politics (especially California politics) I talk about it a lot over on Threads. Fair warning, I am in my #BecerraEra (and not a bot 🤖).

What’s your best book recommendation right now? (If you’re into fiction, since the above selections are all non-fiction, I recommend Kin by Tayari Jones and I See You've Called in Dead by John Kenney.)

Buffy tarot readings! Some of you may know me as an entrepreneurial and business coach, and I indeed do that. But I’ve also spiced things up a bit with tarot readings with my Buffy the Vampire Slayer deck, with or without coaching 🙂

Check out the options here: https://calendly.com/elisacp

Hope you’ll join me! Subscribe here. And share, please do share this link!

It's not something I'm sure will ever fully go away. But it won't be as bad as this. And this was not the worst mistake you'll ever make.

-Rupert Giles (weirdly comforting, right?)

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