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 analyst would have a field day with.

Now, six months post-launch, I am, well … still cautiously optimistic.

Some days are filled with highs, while others are more challenging and disappointing. In that way, it’s no different than my years as an independent school administrator.

High: Launch the new school website to positive reviews.

Low: Watch the amazing family you were sure would enroll instead choose the cross-town competitor.

High: Hit an all-time high in both attendance and net revenue at the annual gala.

Low: End the Annual Fund campaign with a decrease in alumni participation.

This is, of course, just the reality of our work. No matter the organization or the role, some days we are brilliant, and others we question our worth.

I’ve worked in and with independent schools now for nearly 25 years, and as a consultant for about a decade of that. But the imposter syndrome persists. It turns out that changing your tax status doesn’t automatically silence the voice that asks, Are you sure you’re cut out for this? Or, to put a more positive spin on it, perhaps the work simply keeps us humble – always growing, always learning.

But confronting that imposter syndrome head-on over the last six months has given me a few realizations that span positions, tenure, and schools of all types and sizes:

1. Your daily work can still be a grind — even when you love what you do.

My late father-in-law used to say that you know it’s time for a career change if you pull up to work and struggle to get out of the car and go into the office. I agree, with the caveat that we ALL have days where we just want to pull the covers back over our head, and where not even the largest and strongest cup of coffee helps us get over that hump.

So what gets us through? For me, it has always come back to the “why” and my deep-seated belief that nothing is more important than education. It’s changed my and my children’s lives in immeasurable ways for the better, and continues to do so. Yes, the work of schools can be exhausting, but far more often, it’s absolutely exhilarating.

2. People will surprise you in the best way. (And you have to let them).

There is something incredibly unique about independent school communities. They often feel less like a workplace and more like an extended family. Yes, we might technically view the school across town as our competition, but when one of our own is in need, we are far more focused on helping each other than gaining trade secrets.

Why? Because we are mission-driven and deeply committed to people over profit. And we are in it for the kids.

If I ever needed a reminder of this truth, I got it when I announced I was starting my own practice. The outpouring of help, advice, and encouragement from former school colleagues, clients, and other industry professionals was overwhelming. And when you are wrestling with imposter syndrome, you immediately tell yourself people are just being nice, or you find a way to minimize your own value and impact. But part of owning your worth is actually receiving those gestures for what they are. If people are telling you they respect you and your work, you have to believe them. You might just realize you’re the last person in the room to accept it.

3. You have more courage than you give yourself credit for.

Stepping away from a job I loved to launch this business was hands down the scariest thing I have ever done. It actually required courage I didn’t even know I had, because it meant betting entirely on my own value.

But walking onto a campus every single day requires a completely different level of bravery. School leaders demonstrate courage all the time, even if we rarely think to call it that.

From pivoting through a global pandemic, to adapting to how AI is permanently changing the way we teach and learn, to navigating the most anxious generation of students (and parents) we have ever seen. Every day, educators are performing acts that require tremendous courage – sometimes small, and often, outsized. If we can easily recognize and celebrate that immense grit in others, we have to be willing to see it in ourselves, too.

So, here I am … six months in. I’m incredibly grateful for this new challenge and the next chapter, and even more grateful for what this time has prompted me to reflect on, including why I fell in love with this work in the first place. And, just like that feeling at the start of each new school year (you know those subtle butterflies in the stomach?), I’m genuinely excited for what’s to come.