This week delivered a reality check I apparently needed—multiple times. Through several conversations and my own year-end planning sessions, one truth kept surfacing: It’s going to take longer than you think.
I’m not talking about minor delays or small adjustments to your timeline. I mean fundamentally longer. That client pipeline you projected? Double it. The revenue targets you mapped out? Push them back. The moment when you’ll feel like you’ve “made it”? It’s further out than your spreadsheet suggests.
Here’s what nobody tells you when you leave the predictable rhythm of school life after nearly three decades: The business world doesn’t operate on semester schedules. There’s no clear syllabus, no defined benchmarks that signal you’ve moved from freshman to sophomore status. Success in entrepreneurship—especially when serving schools—unfolds on its own mysterious timeline that seems impervious to our careful planning.
But here’s what I’m learning, what these conversations keep reinforcing: The timeline doesn’t actually matter as much as we think it does. What matters is showing up. Every single day. Even when the progress feels invisible. Especially when the progress feels invisible.
And doing the work. Not the glamorous work you see on LinkedIn. Not the highlight reel victories. I’m talking about the mundane, unglamorous, Tuesday-afternoon-in-November work. The follow-up emails. The proposal revisions. The relationship building that won’t pay off for months, maybe years.
After 28 years in education, I thought I understood patience. I’d watched students grow from nervous ninth-graders to confident seniors. I’d overseen multi-year initiatives and strategic plans. But entrepreneurial patience is different. It’s patience without a predetermined endpoint, without the comfort of knowing that June will bring closure and September will bring a fresh start.
Yet there’s something oddly liberating about accepting this reality. Once you stop fighting against the extended timeline and lean into the daily practice of showing up and doing the work, the pressure eases. You stop checking your progress against some arbitrary schedule and start focusing on what you can control: today’s effort, today’s connections, today’s small improvements.
Good things will happen. I believe that with the same certainty I once believed in the transformative power of education. They just won’t happen when your business plan says they should. They’ll happen when consistent effort meets opportunity, when relationships ripen, when the market is ready for what you offer.
So if you’re contemplating this transition or you’re in the thick of it like I am, adjust your expectations now. Whatever timeline you’ve created, stretch it. Then show up tomorrow anyway. Do the work anyway. Because that’s the only timeline that actually matters—the one where you keep moving forward, even when forward feels frustratingly slow.
The students we once taught didn’t grow on our timeline either. They grew on their own. Perhaps it’s fitting that our businesses will do the same.