Three Years Out: What I Miss and What I Don't
Three years. That's how long it's been since I walked away from a 28-year career in private education to strike out on my own. The dust has settled, the initial shock of flexibility has worn off, and I can finally see this transition clearly enough to reflect on what I genuinely miss—and what I absolutely don't.
The Hardest Part Wasn't What I Expected
The first year was rough, but not for the reasons you might think. It wasn't the financial uncertainty or the business-building learning curve that got to me. It was the absence of structure that I'd followed religiously for nearly three decades.
Every morning for 28 years: shave, tie, drive to school, be somewhere specific at a specific time. Then suddenly—complete freedom. Wake up when I want, work from wherever, set my own schedule entirely. You'd think that would feel liberating immediately, but it was actually disorienting. I had to consciously focus on building new rhythms to replace the ones that had defined my adult life.
But now, three years in, I've found my footing. And with that clarity comes the ability to honestly assess what I left behind.
What I Actually Miss: It's All About the People
I miss colleagues. I miss kids. That's really what it comes down to.
There's something irreplaceable about being stuck on a problem and being able to run down the hall to brainstorm with a colleague, boss, or mentor. I definitely miss the ability to unlock ideas through spontaneous collaboration and immediate human connection.
I miss the camaraderie of working in teams. Yes, I still collaborate with clients and partners, but it's different when you're not sharing the same physical space, dealing with the same daily challenges, building something together day after day.
And the kids—even though my last role had me focused externally, away from daily student interaction, I could still choose to walk through the pre-K wing, drop by a game, or stroll through the senior school when I needed that energy. There's something about being around young people that's energizing in a way I didn't fully appreciate until it was gone.
I also miss the first day of school. As I write this in late summer, I'm particularly aware of missing that palpable energy—the excitement, opportunity, and optimism that fills a school building when everyone returns. There's really nothing quite like it.
What I Definitely Don't Miss: The Time Thieves
Meetings. Oh, the meetings. Looking back now, I'm astounded by how much time I spent in rooms talking about things that could have been handled with a simple email. Not all meetings were worthless, obviously, but the majority were either too long, unfocused, or completely unnecessary. I don't miss that at all.
More broadly, I don't miss not controlling my time. I don't miss having my day dictated to me by bells, schedules, and other people's urgent-but-not-important requests. The productivity difference between then and now is staggering. What I can accomplish in a focused morning now used to take me an entire day when I was constantly interrupted.
And I definitely don't miss all the extraneous requirements—the professional development that wasn't, the security clearances, the various tests and certifications. I understand why schools need these things, and I appreciated their necessity when I was there, but I certainly don't miss spending time on them.
The Real Question for You
I share this reflection not to convince anyone to leave or stay, but to help you think clearly about what matters to you. If the daily interaction with colleagues and students is what energizes you most about education, leaving might be harder than you think. If you're constantly frustrated by bureaucracy and a lack of autonomy, entrepreneurship might be exactly what you need.
The transition isn't just about building a business—it's about rebuilding your identity and daily rhythms after decades of institutional structure. Understanding what you'll miss and what you won't can help you prepare for both the challenges and the relief that come with this kind of career leap.
Three years out, I can say with confidence: the things I miss are real, but they weren't enough to keep me. The things I don't miss were apparently more important to my daily satisfaction than I realized when I was living with them every day.
Your calculation might be different. And that's exactly as it should be.