Insights
The Latest
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6 Months, a New Tax Status, and the Same Imposter Syndrome
When I launched Penny Abrahams Consulting in January 2026, I wasn’t entirely sure what to expect. I was cautiously optimistic, but there were a lot of sleepless nights. And those nights when I did sleep were often filled with wild and intense work-related images that I’m sure any good dream…
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Marketing ‘Icks’ and What They Mean for Gen Z Alumni Engagement
A Note from Penny: We talk a lot in advancement about “understanding our audience.” So, I’m stepping away from the keyboard for this post and handing the mic over to my 23-year-old daughter. If you want to know how Gen Z actually views your school’s marketing campaigns, stop reading think-tank…
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The Worst Compliment I Ever Received, and What it Taught Me About Leadership
Years ago, early in my career, a mentor I deeply respected was giving me some feedback. She told me, “Penny, you are an excellent manager.” She meant it as a compliment. I’m sure she did. But what I heard, and what stayed with me for a long time, was: “You’re…
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The Committee Meeting that Ate Your Advancement Team’s Week
An independent school Advancement director walks out of a Board committee meeting with six new action items … none of which were on her agenda when she walked in. Her actual work is sitting back at her desk, untouched. The trustees who generated those items? They left feeling engaged and…
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Does Your School’s Org Chart Reflect Its Future, or Its History?
If you’ve spent any time in independent school leadership, you know this scenario. Let’s call her Ms. Gable. Ms. Gable is the heart and soul of the arts department. She’s directed every spring musical since 1989. She’s the one who always stays late to help students practice their lines, and…
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Don’t Leave Your New Families Wondering if They Made a Mistake
When I turned 49 last year, I decided I wanted to take a trip to Sedona for my 50th birthday. To make that wish come true, I knew I’d have to get pretty disciplined with my budget. So, every month, I tucked away whatever I could. Finally, just a few…
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I Closed the Tab, and So Will Your Prospective Families
4-minute read After about 15 minutes of trying to register for a local class, I finally gave up. I had my credit card ready. I’d been waiting for a class date that fit my schedule. The class was even at my preferred location. But after running into repeated “Invalid Password”…
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Reclaiming Alumni Engagement with the Nostalgia Factor
This week I’m onsite at the CASE-NAIS Independent Schools Conference in Seattle, and I’m thrilled to see so many sessions focused on alumni engagement. It speaks to a challenge so many schools are feeling: How do we get the attention of our busy former students when they are already bombarded…
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Beyond the Listening Tour: The First 100 Days for the New Head of School
If you scroll through LinkedIn this time of year, your feed (like mine) is likely a steady stream of new K-12 Head of School announcements. And if you are fortunate enough to be one of those new Heads, your July calendar is already starting to fill up. Between the board…
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The Burnout is Coming From Inside the School Calendar
Right now, in a conference room on a campus near you, an independent school leadership team is sitting down to plan the 2026-27 school year. Maybe it’s even YOUR leadership team. You have a blank grid in front of you. You have a chance to start fresh. You have the…
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The “I’m Fine” Default: Why School Leaders need to Drop the Facade
My typical Saturday morning routine includes dog walks, coffee, and my favorite podcast lineup, and today that meant tuning into This Empty Nest Life, hosted by my dear friend and former colleague, Jay Ramsden. In this particular episode, he was interviewing Amber Fuhriman, author of “Break Your Bullsh*t Box.” She…
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Why I’m Trading Resolutions for Intentions This Year
I’ve never been big on New Year’s resolutions. It’s not that I haven’t set them. I’ve done the usual routine … I set a goal, I stick to it for a few days or weeks, and then life gets in the way. I “break” the resolution, and suddenly I’m left…