The Sales Cycle Trap: Why You Can't Stop Selling (Even When You're Swamped)
I've been having some wonderful conversations with consultants who are new to the education entrepreneurship space recently, and there's a mistake I keep seeing – one that I made myself and want you to avoid.
When I decided to leave school and start my own business, I was in full sales mode. I was on fire. I sold, I sold, I sold. Landing those first clients felt incredible – the validation, the excitement, the rush of "I'm actually doing this!" I threw myself into that client work with everything I had.
And then, a few months later, I looked up from my laptop and realized something terrifying: I had completely stopped selling. The pipeline was bone dry.
"Oh darn," I thought (okay, I probably used stronger language), "I need to start selling again."
What followed was about a year of the most exhausting cycle you can imagine. I'd sell like crazy, land clients, get completely buried in delivery work, stop selling entirely, finish the projects, panic about no incoming business, then frantically start selling again. Rinse and repeat.
It was like being on a business roller coaster that I couldn't get off.
The Educator's Selling Blindspot
Here's what I think happens to those of us coming from schools: We're used to defined seasons. There's a time for curriculum planning, a time for teaching, a time for assessment. In schools, we compartmentalize our work because the academic calendar forces us to.
But entrepreneurship doesn't work that way. There are no neat semesters or summer breaks from business development.
The irony is that in schools, we're constantly "selling" – presenting ideas to administrators, getting buy-in from colleagues, and convincing parents of our programs' value. But we don't think of it as selling because it's wrapped in education-speak and happens within established relationships.
When you're building a business that serves schools, you need that same continuous relationship-building and idea-sharing, but now it's explicitly tied to revenue. And if you stop, the money stops.
Always Be Selling (But Not How You Think)
My advice to anyone starting this journey: You always have to be selling.
But let me be clear about what this means, because "always be selling" probably makes your educator's heart cringe a little.
This doesn't mean being pushy or sleazy or constantly pitching. It means:
Maintaining visibility with your network even when you're busy with client work
Nurturing relationships that might turn into opportunities months from now
Sharing insights about your work that demonstrate your expertise
Having conversations with potential clients, even brief ones
Following up on proposals that are sitting in someone's inbox
It can be as simple as sending one LinkedIn message per day or making two follow-up calls per week. When you're slammed with client work, dial it down to whatever you can sustain. But never turn it off completely.
The Pipeline That Never Sleeps
Think of it this way: In schools, enrollment happens on a cycle, but the marketing and relationship-building that leads to enrollment never stops. Schools are always nurturing prospective families, always building their reputation in the community.
Your business needs the same approach. Even when you're delivering amazing work for current clients, you need to be planting seeds for future projects.
The hardest part is that sales activities often feel less urgent than client deliverables. When a school is waiting for you to finish their strategic plan, that feels more pressing than reaching out to three new prospects. But that thinking will keep you stuck in the feast-or-famine cycle.
Breaking the Cycle
Here's what finally worked for me: I scheduled selling activities like they were client meetings. Non-negotiable time blocks. If I could protect time for client calls, I could protect time for prospect calls.
The goal isn't to book every conversation into immediate business. It's to stay visible and relevant so that when schools have a need, you're the person they think of.
Your Turn
If you're starting out, build these sales habits now, before you get your first big client. If you're already in the cycle I described, break it this week. Even if you're buried in client work, do one small selling activity today.
Trust me on this: the pipeline you build today feeds the business you'll have six months from now. Don't let your success become the thing that kills your momentum.
What's your plan for staying visible even when you're busy? I'd love to hear how you're thinking about this challenge.