Lost in the Supermarket
This edition dives into overcoming burnout and taking control of your calendar while announcing a workshop!
In this edition:
- Burnout and Leadership
- Own Your Calendar
- Registration is open for Mid-Year Reset Workshop
It’s been a minute. After the last newsletter, I heard from several folks that they loved the edition, which was great...until it wasn't. I second-guessed myself straight into silence, and now it’s been two months since my last one! Egads.
“What if what I’m writing this time sucks and everyone thinks I’m a dork?"
Actual thought, courtesy of my inner critic. But the next seasonal reset workshop is coming to The Getaway soon and I needed to get this out! So here we are, sending a newsletter on a Tuesday. Grab a freshie (beverage) and settle in. I hope this helps you feel more human in the midst of whatever calendar mess you’re navigating this week.
Burnout Isn’t Always Loud
There’s a Reddit Post I read last year that I have not been able to shake.
"I work in tech leadership, FAANG adjacent company but filled with all FAANG execs and senior leaders. I have lost the desire to work now. I used to love what I did and have been a top performer. And about 4 months ago I genuinely lost all motivation. Part of the reason is I dont like what my role has turned out to be. Constant stakeholder management, diplomacy, allyship, alignment meetings coz we are such a matrixed organization, status updates - like when the hell am I to spend time actually building products."
That shift from work being about building to performing went slow and unnoticed, but now it sounds like it's the lion's share of work activity in office / knowledge work. (Am I wrong? Please tell me I'm wrong - I'm looking for stories of effective teams and orgs!)
The people who used to light up at the challenge now spend their days navigating optics, attending meetings about meetings, and tiptoeing through political choreography designed to keep the illusion of alignment intact.
Meanwhile the actual work - the stuff that creates value, reduces tech debt - solves tricky problems - it gets pushed to the margins, completed at night and squeezed in around the decks. It’s fueled by hope in a gas tank that’s running dry.
The coach who responded said something prescient:
“The problem I see with people in similar frames of mind is that over time they get so burnt out from doing bullshit work that their self esteem and confidence goes down the drain— which stops them from asking for what they want or applying for other companies.”
I think she nailed it when she said, “so burnt out from doing bullshit work”. That’s the part that gets me. It's not only that it's energy draining, but also, it’s really demoralizing.
And I think it takes the biggest toll on the loyal, hardworking folks that are committed to the org and the org's purpose, because they're the ones that put up with it and follow along. They bend themselves to the environment, and as a result, end up wondering what value they have, feeling a lack of marketable skills or an inability to point to real impact on their resumes. It’s not just time or progress we’re losing - it's possibility and potential also take the hit.
You Own Your Calendar. Act Like It.
Let’s talk about calendars. Specifically, yours.
If your days look like a Tetris board someone rage-built with too much caffeine and no regard for human life—triple-booked, no breaks, back-to-back-to-back until your neck and your brain both stop working—you’re not alone.
I’ve seen calendars that are indistinguishable from panic attacks. People literally forget to eat. They show up to every meeting half-there, with no time to reflect, strategize, or even breathe. But the fire keeps burning and they keep showing up. Watch this Tiktok and notice if you ever showed up like this to your team.
This is fine, right? Except it’s not.
You were hired for your insight, experience, judgment, knowledge. And you have to be able to think in order to deliver any of that.
So let’s draw a line this week.
This week, I want you to look at your calendar and find one hour you can clear
Move a meeting. Cancel a meeting. Excuse yourself from a meeting. Send someone in your place.
But find an hour—and clear it.
And protect it! Do not wither it away.
Do not answer email or clear your inbox.
Don’t let the meeting before it run long and steal your time.
This is YOUR TIME.
Instead, use that hour to use your mind. Here are three ways you can spend it.
Idea #1: Play Piles (my new favorite card game)
Find a friend and play Piles. This is a weird suggestion but this new card game I found, it activated my brain in entirely new ways. I was cognitively exhausted the first few times we played! It’s fast. It requires a totally different part of your brain than the one that’s been powering through slide decks and late-night emails. And yes—it’s fun.
Idea #2: Try Inversion Mapping
Pick something core to your leadership life: your meetings, your team structure, your calendar. Ask:
“What would it look like to do the opposite?”
Then dive deeper:
- What if no one could put time on your calendar without a form?
- What if your team didn’t meet synchronously for a week?
- What if your next initiative didn’t need a deck?
Force the reversal and make it ridiculous. Then ask: is any part of this worth testing?
Let the inversion surface what you’ve been tolerating without noticing. You don’t have to solve or change anything. Practice how to explore a topic.
Idea #3: Go on a Story Safari
Spend one hour hunting for bold, strange, or human leadership decisions. No frameworks, just stories.
Look for:
- What did this person try that others wouldn’t?
- Where did they hold the line?
- What would that look like in your world?
Start with Farnam Street, Corner Office, or The Knowledge Project.
Track what stirs something.
Announcing: The Mid-Year Reset!
It’s back. And you don’t want to miss this one!
This is our third time running the Mid-Year Reset. If you’ve been to one, you already know: this workshop is a breath of fresh air. We have four offerings to prepare you for the second half of 2025 [editor’s note: "prepare" and "2025" in the same sentence…laughable, Summer]
- Friday, May 23, 9:00 AM - 1:00 PM
- Saturday, May 24, 9:00 AM - 1:00 PM
- Thursday, June 19, 10:00 AM - 2:00 PM
- Saturday, June 21, 9:00 AM - 1:00 PMM
It’s for women, for moms, for people whose lives feel a little over-optimized and under-inspired. Our Seasonal Resets are well structured and supportive workshops that will help you take on the second half of the year with intention. We'll work out your goals and priorities, routines and rhythms and give you a sense of calm and readiness. And it's so much more fun to do with others - laughter, ideas, tips and connection.
You’ll leave with a clearer head, a refreshed outlook, a working, realistic plan for the rest of the year. You’ll also get a workbook and some extra time at the end to keep planning.
Your time and energy deserve respect, even from you.
If you’ve been feeling off track or out of sync, this is your moment to recalibrate.
Learn more about the Mid Year Reset here!
More soon. Or maybe not soon. But eventually.
If you made it this far, thanks for reading.
And if you need someone to say it plainly: you're not craz, the current situation we built is. But you do need a reset.
—Summer