For 28 years, I had an answer. School name, role, done. The other person nodded, made a connection of their own (”oh, my niece went there”), and we moved on to whatever came next.

That’s not how it goes anymore.

Now I open my mouth and watch the other person’s face for the first sign of confusion. Digital marketing. Independent schools. K through 12. Strategy. Helping schools that can’t afford a full-time marketing director get marketing support without the full-time salary.

By the time I’m done, the conversation has shifted. They’re being polite. They’re nodding. But the easy back-and-forth that used to happen after my old answer is gone.

I used to think this was a marketing problem. If I could just tighten my elevator pitch, I’d land it cleanly. So I worked on it. I rehearsed different versions. I tested them on my wife. None of them solved the problem, because the problem wasn’t the pitch.

The problem was that I had spent 28 years letting an institution do the explaining for me.

When I said the school name, the school did all the work. Everyone had a frame for what a school was. They knew what a director of admissions did, even if they didn’t know the specifics. They had stories about their own school days. There was shared ground before I said anything personal at all.

Now there’s no shared ground. I’m a person nobody has heard of, doing a job most people don’t have a category for, serving a niche that requires explanation. The institution used to fill in all the blanks. I have to fill them in myself, every time, with someone new.

What surprised me was how much of my identity was wrapped up in that shortcut.

I didn’t realize, when I was working at a school, how much of who I thought I was depended on the school being the thing that introduced me. The school was the noun. I was the adjective attached to it. People knew what the noun was, so they assumed they knew what I was, even when they didn’t.

When the noun went away, I had to become the noun.

That has been one unexpected, difficult piece of this transition. Not the money. Not the schedule. Not the workload. The slow, ongoing work of being someone who has to introduce himself from scratch instead of being introduced. Mind you, this is not about ego for me; it’s about identity and how much of our work, and what we do, is who we are.

I’ll be honest. I’m not great at it yet. Three and a half years in, and I still stumble through the answer at parties. I still over-explain. I still see the polite nod and feel the small pang of missing the days when my title was a complete sentence.

But here’s what I’ve started to notice. The people who do this work well, the consultants and entrepreneurs I’ve watched closely, share something in common. They’ve stopped trying to translate their old institutional identity into a new entrepreneurial one. They’ve built a new identity from the ground up, one that stands on its own.

That’s the work I’m doing now. Not just building a business. Building an answer to a question that used to take me half a second.

If you’re thinking about leaving a school, or any institution that has carried you for a long time, this is worth knowing in advance. You’re not just leaving a job. You’re leaving the shortcut that lets you walk into rooms and have people understand who you are without you having to say it.

Be ready to do that work yourself, for yourself.

And if you’re now on the outside trying to sell to schools, you probably assume that understanding this cycle is the key to timing your outreach perfectly.

You’re half right.

The Cycle Is Real

Every school handles budgeting differently, but the general rhythm at most independent schools follows a similar pattern. The fiscal year typically runs from July to June. Budget requests from department heads and division leaders start getting assembled months before that, sometimes as early as November. At my last school, we did zero-based budgeting, which meant every dollar had to be justified from scratch every year. We started our initial planning in November, and department and division heads were all part of that process.

Those early requests were usually pretty accurate. But because they happened so far in advance of the actual fiscal year, things inevitably changed. Adjustments came in the spring. Sometimes even in the summer. A line item that looked solid in December might get cut in April because enrollment projections shifted or a capital project took priority.

By the time July rolled around and the new budget was live, it rarely looked exactly like the version that was first submitted months earlier.

If you’re an education consultant or entrepreneur serving schools, this matters. If a school is finalizing budget requests right now, in March, and you’re not part of that conversation, your service probably isn’t getting a line item for next year. That’s just the reality of institutional planning.

But Here’s What Nobody Tells You

The budget cycle is important. Understanding it gives you a real advantage over consultants who treat every month the same. But if I’m being honest about my own experience, I don’t always know where I fall in a school’s budget cycle. From the outside, you rarely get a window into when those internal conversations are happening. You’re not sitting in those November meetings anymore. You’re not copied on the budget email.

And here’s the thing I’ve learned that I wish someone had told me earlier: schools don’t only buy on schedule.

Some of the most important purchasing decisions schools make happen completely outside the budget cycle. A key staff member leaves unexpectedly, and suddenly there’s an urgent gap to fill. A head of school attends a conference, hears a keynote that lights a fire, and comes back ready to invest in something new. A board member raises a concern that creates immediate pressure to act. Enrollment numbers come in softer than expected mid-year, and the panic button gets pushed.

These moments don’t show up on any planning calendar. They’re reactive, urgent, and often funded by reallocating dollars from other parts of the budget. They happen in October, January, and April, and every month in between.

The Real Lesson

So, where does this leave you if you’re building a business that serves schools?

You need to understand the budget cycle. Full stop. Knowing that schools plan months in advance, that budget requests happen in the fall and winter, and that the fiscal year resets in July, all of that gives you context that most outside vendors don’t have. That insider knowledge is one of your advantages as a former school person.

But you can’t be held hostage by the calendar.

If you spend all your time trying to perfectly time your outreach to the budget cycle, you’ll miss the school that needs you right now because something unexpected happened last week. You’ll miss the head of school who just realized they have a problem they didn’t anticipate. You’ll miss the opportunities that don’t follow a schedule.

The answer, as unsatisfying as it sounds, is to do both. Understand the rhythm of how schools plan and spend. But also keep showing up consistently, regardless of where you think a school is in its cycle. Because the truth is, you don’t always know what’s happening inside those walls anymore. You can make educated guesses based on nearly three decades of experience, but the purchasing trigger might be something you never could have predicted.

Be visible. Be helpful. Be patient. And when the moment comes, whether it’s on the budget calendar or completely off it, be ready.

I was sitting in my home office, still getting used to the quiet. No morning announcements. No bells between periods. No colleagues popping in to ask about the spring gala. Just me, a laptop, and a school administrator on the other end of a Zoom call who needed help with digital marketing.

“So what does something like this cost?”

And in that moment, my brain did something unhelpful. It did the math. It took my old school salary, divided it by twelve, divided that by the number of working hours in a month, and arrived at a number.

That number was wrong. Completely, dangerously wrong.

The Salary Anchor

Here’s what happens when you’ve spent 28 years receiving a paycheck from a school. That salary becomes your anchor. It’s not just a number on a direct deposit. It’s your reference point for what work is worth, what you are worth, what someone should reasonably pay another human being to do a job.

So when it comes time to put a price on your consulting, your training, your expertise, you instinctively reach for the only financial framework you’ve ever known.

Your old salary.

You think: I was making X per year, so I should charge something in that range, right?

Wrong. And I’ll tell you why.

What Your Salary Actually Covered

When a school paid you a salary, they weren’t just paying for your expertise. They were paying for your presence. Your attendance at faculty meetings. Your willingness to chaperone the winter formal. Your availability from 7:15 AM to whenever you actually left the building, which was rarely before 5:00.

They were also giving you things that had real monetary value: health insurance, retirement contributions (11.5% at my first school, if you recall from a previous post), paid time off, professional development budgets, and the invisible infrastructure of an institution. An IT department. An HR department. A building you didn’t pay rent on.

When you go out on your own, all of that disappears. Every bit of it. And it has to come from somewhere.

That somewhere is your pricing.

The Hourly Rate Trap

The most common mistake I see from former school people, and one I made myself, is converting your salary into an hourly rate and calling it a day.

Let’s say you were making $120,000. Divide by 2,080 working hours, and you get roughly $58 an hour. So you think, I’ll charge $60 an hour. Maybe $75 if I’m feeling bold.

But you’re not billing 2,080 hours a year. You’re not even close. Between marketing, invoicing, networking, proposal writing, professional development, and the dozens of other tasks that keep a business running, you might bill 1,000 hours if you’re lucky. Maybe 800 when you’re starting out.

Now do the math again. $120,000 divided by 800 billable hours is $150 an hour. And that’s before you account for health insurance, self-employment taxes, retirement contributions, software subscriptions, and the reality that you don’t get paid when you’re sick, on vacation, or between clients.

Suddenly, that $60 rate doesn’t look so reasonable.

The Discomfort Is the Point

I won’t pretend this is just a math problem. It’s an emotional one. And I think it’s worth being honest about why.

In schools, we are culturally conditioned not to talk about money. I’ve written about this before. Salaries were practically secret. Asking a colleague what they made would have been like asking them about their marriage. You just didn’t do it.

So when you step into a world where you have to name your own price, it feels wrong. It feels greedy. It feels like you’re betraying some unspoken code that says educators shouldn’t be in this for the money.

But here’s the thing. Pricing yourself appropriately isn’t about greed. It’s about sustainability. I wrote a few weeks ago about the difference between free and paid, and how the only real validation of a business idea is when someone hands over money. Pricing is the next chapter of that same story. If you undercharge, you’re not being humble. You’re building a business that can’t sustain itself. And an unsustainable business doesn’t help anyone, least of all the schools you’re trying to serve.

What I’ve Learned About Pricing

I’m still figuring this out. I want to be clear about that. But here’s what I’ve picked up so far, sometimes the hard way.

Price the outcome, not the hours. Schools don’t care how many hours you spend. They care about results. When I shifted from thinking about my time to thinking about the value I deliver, everything changed. A school doesn’t pay me for 20 hours of digital marketing work. They pay me because enrollment inquiries go up, because their website starts working for them instead of against them, because prospective families find them and choose them.

Your experience is not entry-level. After 28 years in education, I walked into entrepreneurship with deep institutional knowledge that most consultants spend years trying to acquire. I understand school culture, decision-making processes, board dynamics, parent expectations, and the rhythms of an academic year. That knowledge is enormously valuable. Don’t price it like you just graduated.

Recurring revenue changes the conversation. I’ve talked about this in the context of managing variable income, but it matters for pricing too. When you can offer ongoing monthly support instead of one-off projects, you can price in a way that reflects the cumulative value you provide. It’s also better for your clients. Schools benefit more from sustained partnership than from a consultant who swoops in, delivers a report, and disappears.

The first number you say is rarely the final number. Schools negotiate. Boards have budget constraints. That’s fine. But if you start from a number that already undervalues your work, where do you go when they ask for a discount? Even lower? Start from a position that reflects your real value, and you’ll have room to work with people while still building a business that pays its own bills.

The Real Question

Here’s what it comes down to. And this is the part nobody prepares you for when you leave the school world.

You have to decide what you believe you’re worth.

Not what the salary scale said. Not what your former colleagues might think. Not what feels safe or comfortable or appropriately modest.

What you’re actually worth, based on what you know, what you can do, and what results you can deliver.

That number will probably make you uncomfortable the first time you say it out loud. Good. The discomfort means you’re growing past the salary anchor that’s been holding you in place.

If you’re at the beginning of this journey, or stuck in the middle of it, know that the pricing question doesn’t have a perfect answer. But it does have a wrong one, and that wrong answer is whatever number you arrive at by dividing your old salary by twelve.

You’re worth more than your last paycheck. Start there.

Three and a half years into running my own business, I notice it now.

The Invisible Infrastructure

Here’s something nobody warned me about when I made the leap from school employee to entrepreneur: you are now the finance office. You are both the accounts receivable and accounts payable departments. You are the person who tracks expenses, sends invoices, follows up on late payments, manages receipts, figures out quarterly taxes, and tries to remember which software subscription renewed this month and which one is hitting next week.

All those systems that hummed along in the background at your school? The ones you never had to think about because someone else was thinking about them? Those are your responsibility now. Every single one.

I knew, intellectually, that running a business meant handling the business side. But knowing it and living it are entirely different experiences. The sheer volume of small financial tasks that pile up when you’re on your own is something I genuinely did not anticipate.

Everything Takes Longer Than You Think

The other thing I underestimated is how long all of this takes when you’re not an expert. At school, the business office had people who’d been doing this work for years. They had systems, institutional knowledge, and the kind of efficiency that comes from repetition.

I had none of that. I had Google searches, YouTube tutorials, and a lot of trial and error. Setting up accounting software that someone with experience could configure in an afternoon took me the better part of a week. Tasks that should be routine still require me to stop and think, to double-check that I’m doing it right, to fix the mistakes I made because I didn’t fully understand what I was doing the first time.

This isn’t a complaint. It’s just the reality. When you leave the infrastructure of a school, you’re not just losing colleagues and a steady paycheck. You’re losing an entire support system you probably didn’t even realize was there.

The Learning Curve Is Real

I eventually got smart enough to hire an accountant, which was one of the better decisions I’ve made in this journey. I also invested in software to handle some of the tracking and invoicing I was doing manually (badly) in spreadsheets. These things helped. A lot.

But even with help, there’s a baseline level of financial literacy that running a business requires, and I’m still building it. I’m still learning terminology I never needed to know before. Still figuring out which expenses go in which category and why it matters. Still discovering things I should have been doing six months ago that nobody told me about, because why would they? Everyone assumed I already knew.

If you spent decades in education, you probably didn’t spend a lot of time thinking about invoicing or bookkeeping or the finer points of estimated tax payments. I certainly didn’t. And now I think about them all the time.

A Heads-Up, Not a Warning

I’m not sharing this to scare anyone away from the leap. The freedom and autonomy of running your own business are worth the administrative hassle. But I do think people making this transition deserve an honest picture of what “being your own boss” actually entails day-to-day.

It’s not just the exciting parts. It’s not just landing clients and doing the work you’re passionate about. It’s also the unglamorous hours spent reconciling accounts, chasing down receipts, and figuring out why your numbers don’t match up.

If you’re still in a school job and considering the move, take a moment to appreciate the finance office. The HR department. The IT team. All those people are doing work that makes your job possible without you ever having to think about it. You’re about to become all of them, at least until you can afford to hire help.

The Expense Report Moment

There’s a specific kind of moment that captures this transition for me. It’s the first time you realize that nobody is coming to handle the thing you used to hand off to someone else. The first time you sit down with a pile of receipts and think, “Okay, what do I actually do with these?”

That moment is humbling. It’s also clarifying. You start to understand just how much invisible labor was happening around you, and you develop a new respect for the people who do this work professionally.

I’m still learning. Still getting better at the back office stuff. Still occasionally discovering that I’ve been doing something wrong for months.

But at least now I know where the expense reports go. They go to me.

The Expert Problem

There’s a certain kind of content out there that I’ve never been comfortable creating. The kind where someone positions themselves as the person who’s cracked the code, who has the system, who’s moved past the uncertainty into some state of complete clarity. That’s not me. And honestly, I’m skeptical of anyone who claims it is.

The transition from school life to entrepreneurship isn’t a problem you solve once. It’s an ongoing process of figuring things out, recalibrating, and figuring them out again. Anyone who tells you otherwise is either unusually lucky or leaving out significant parts of their story.

What I Can Offer Instead

Here’s how I think about what I’m doing with this newsletter: I’m just a little bit ahead of you. Not miles ahead. Not at the finish line waving you forward. Just a few steps further down a path we’re both walking.

That means I can tell you what I’ve encountered recently, what worked, what didn’t, and what I wish I’d known six months ago. I can share those lessons while they’re still fresh, not filtered through years of hindsight that smooths out the rough edges. I think there’s real value in that. Real-time honesty rather than polished expertise.

A Lesson I’m Still Learning

If you want an example, here’s one I’m living right now: I expected this to move faster. When I started, I had timelines in my head. Milestones I thought I’d hit by certain points. Revenue targets, client numbers, all of it. And almost none of it happened on the schedule I imagined.

That’s not a failure. It’s just the reality of building something. But I spent a lot of energy in the early days feeling like I was behind, like something was wrong, because my expectations were completely out of sync with how this actually works. I’m still recalibrating those expectations. Still practicing patience. Still reminding myself that the timeline I invented in my head was never real to begin with. If I were writing from “expertise,” I might package that as a lesson I’ve fully absorbed. But the truth is I’m still in the middle of learning it, and some days are easier than others.

Why This Matters for You

If you’re reading this newsletter because you’re considering the leap, or because you’ve already made it and want some company on the journey, I want you to know what you’re getting. You’re not getting someone who has all the answers. You’re getting someone who’s actively searching for them and willing to share what he finds along the way.

You’re not getting a highlight reel. You’re getting an honest account of what this transition actually looks like, including the parts that are slow and uncertain and unglamorous. And you’re getting the lessons as I learn them, not years later when they’ve been polished into tidy principles that sound good but lose the texture of real experience.

Still in the Trenches

I chose the name “Unschooled” for this newsletter because it captures something true about where I am. I’m unlearning a lot of what I thought I knew. I’m figuring out a new way of working that doesn’t come with a syllabus or a clear grading rubric. Three and a half years in, I’m more confident than I was at the start, but I’m not done. Not even close!

So that’s what you can expect from me. Not expertise from a distance, just experience from the middle of it. I hope that’s useful. I think it’s more honest than the alternative.

It all looks so smooth. So inevitable. So fast.

Here’s what I want you to know if you’re considering this leap or you’re early in the journey: what you’re seeing isn’t the whole picture. It’s not even close.

The Highlight Reel Problem

Nobody posts about the Tuesday afternoon when they refreshed their inbox twelve times, hoping for a response that didn’t come. Nobody talks about the proposal that took hours to write and went nowhere. Nobody shares the months when income was unpredictable, and the math felt impossible.

Social media rewards the wins. It rewards confidence and momentum and transformation stories with clean arcs. What it doesn’t reward is the long, unglamorous middle where most of the actual work happens.

So we get a distorted picture. New consultants see these posts and think something is wrong with them when things don’t click immediately. They wonder why everyone else seems to be figuring it out faster. They start questioning their idea, their pricing, their strategy, when really the only thing they’re missing is an accurate sense of how long this takes.

The Timeline Problem

Here’s my advice, and I wish someone had given it to me earlier: whatever timeline you’re projecting for this business to work, add more time.

Think it’ll take six months to build a steady client base? Plan for twelve. Think you’ll replace your school salary in a year? Give yourself two. Think you’ll feel like you know what you’re doing after a few contracts? Add another year to that, too.

I’m not saying this to discourage you. I’m saying it because mismatched expectations are what cause people to quit too early or burn out from frustration. When you expect it to be hard and slow, you can pace yourself. When you expect it to look like the LinkedIn posts, every normal setback feels like a sign you’re failing.

You’re not failing. You’re just building something, and building takes time.

The Financial Reality

The other thing social media glosses over is the financial uncertainty. School jobs come with predictable paychecks. You know what’s hitting your account and when. You can plan around it.

Entrepreneurship doesn’t work that way, especially in the early years. Income is lumpy. A great month might be followed by a quiet one. You’ll land a contract and feel relief, and then immediately start wondering where the next one is coming from.

This isn’t a sign that you’re bad at business. It’s just the nature of the transition. But you won’t see anyone posting about it because it doesn’t make for an inspiring story.

The Emotion That Matters Most

If I had to name the single most important quality for surviving this transition, it wouldn’t be hustle or strategy or even talent. It would be patience.

Patience to keep showing up when results are slow. Patience to trust the process when you can’t see progress. Patience to let relationships develop into opportunities over months or years rather than days. Patience to build something real instead of something that just looks good on social media.

The rewards of this path are genuine. The freedom, the autonomy, the ability to build something that’s yours. But those rewards come to people who stay in the game long enough to earn them. And staying in the game requires patience more than anything else.

What I’d Tell You Instead

If I could replace every polished success story with a more honest message, it would be this: it’s probably going to take longer than you think, feel harder than it looks, and test your patience in ways you didn’t expect. And that’s normal. That’s the path.

The people posting their wins went through the same uncertainty you’re feeling now. They just aren’t posting about that part.

So if you’re in the thick of it and wondering why your journey doesn’t look like theirs, stop comparing. Their timeline isn’t your timeline. Their wins don’t say anything about your potential.

Keep going. Be patient. The results will come.

“That’s a great idea.” “You should totally do this.” “Schools definitely need that.”

It felt good. Validating, even. I took all that encouragement as evidence that I was onto something real.

Here’s what I’ve learned since: encouragement is not validation. Not even close.

The Encouragement Trap

When you’re starting out, it’s easy to mistake activity for traction. People sign up for your free webinar. You get likes and comments on LinkedIn. Former colleagues want to grab coffee and “pick your brain.” Someone shares your post. Another person says they’ll “definitely reach out when they have budget.”

All of this feels like progress. It feels like the market is telling you something.

But none of it is validation. It’s just noise.

The only validation that actually matters is when someone pays you. Upfront. Real money. For the thing you’re selling.

Why This Distinction Matters

I’m not saying encouragement is worthless. It’s nice to hear. It can keep you going on hard days. But it can also lead you down a dangerous path where you spend months (or years) refining an idea that nobody will actually buy.

People are generous with encouragement because it costs them nothing. Telling someone “that’s a great idea” is easy. It makes them feel good, it makes you feel good, and nobody has to make a hard decision.

But when you ask someone to pay, everything changes. Now they have to weigh your offering against other priorities. They have to justify the expense. They have to believe that what you’re providing is worth more than the money in their pocket.

That’s a completely different calculation than “does this sound like a neat idea?”

The Hard Truth

Here’s what I wish someone had told me earlier: the only real test of whether your idea has legs is whether people will pay for it. Not whether they’ll attend a free event. Not whether they’ll engage with your content. Not whether they’ll say nice things when you describe it.

Will they open their wallet?

If they won’t, you don’t have a business. You have a hobby that people find interesting.

What This Means Practically

I’m not suggesting you need to have everything figured out before you ask for money. But I am suggesting that you test your assumptions with actual transactions as early as possible.

Instead of building out a full course and then seeing if anyone buys it, sell it first. See if anyone will put money down before you’ve created it. If they will, you’ve got validation. If they won’t, you’ve just saved yourself months of work on something the market doesn’t want.

Instead of offering free consultations to “build relationships,” quote a price. The people who say yes are your real market. The people who say “let’s stay in touch” were never going to buy anyway.

This feels uncomfortable, especially for those of us who spent decades in education where talking about money was almost taboo. But discomfort is part of the transition. You’re in business now. And businesses need paying customers, not just fans.

The Question Worth Asking

If you’re in the early stages of this journey, or even if you’ve been at it for a while, ask yourself honestly: How much of what I’m calling “traction” is actually just encouragement?

Are people paying you? Or are they just cheering you on?

Both have value. But only one keeps the lights on.

January 1st was just... mid-year. A brief pause in the middle of the school year. A chance to catch your breath between the holiday concert chaos and the spring enrollment push. The real fresh start came when buses rolled up in late summer, new faces filled the hallways, and everything reset.

This is my fourth January as an entrepreneur. And I still don’t know what to do with it.

The world wants me to set resolutions. Make bold predictions. Declare this “my year.” But my body and brain are still wired to the academic calendar. Four years out, and January still feels like the middle of something, not the beginning.

Here’s what I’ve learned: 28 years of conditioning doesn’t disappear just because you change your business card. The rhythms that structured your professional life leave deep grooves. And entrepreneurship doesn’t hand you natural reset points to replace them. There’s no summer break to regroup. No new school year to wipe the slate clean. You have to manufacture your own rhythms or risk running on a treadmill that never stops.

So instead of resolutions, I’m asking myself a question I revisit every January: What rhythms have I built, and are they actually working?

Maybe that’s the real long-term work of this transition. Not just building a business, but building a life structure from scratch when the one you relied on for three decades disappears.

To those of you still in schools: enjoy that mid-year pause. You’ve earned it.

To those of you who’ve made the leap: how do you mark time now?

Whether you’re still at a school or you’ve left and you’re building something on your own, I want to tell you something I wish someone had told me years ago: please take time off.

I’ll be honest about how I used to approach breaks. I viewed them strategically. The holidays meant fewer emails, fewer requests, fewer people needing something from me. The external noise quieted down, and I would use that silence to catch up, to get ahead, to clear the decks for January.

I’m not saying that’s a terrible approach. There’s logic to it.

But here’s what I’ve learned, and I’m learning it later than I should have: nothing good comes from pushing yourself into the ground.

So this is my ask. Take a few days off this week. Or if you can’t manage that, take one solid day. One day where you don’t do any work. Put the screens away. Really unplug.

I can’t overstate how healthy this is. Physically, your body needs the rest. Mentally, your brain needs the space. I spent too many years treating rest as something I would earn later, something that would come after the next project, the next deadline, the next crisis. That thinking was wrong.

Learn from my mistakes on this one.

Have a wonderful holiday season with your family.

Now that I’m on the outside serving schools, I’ve learned that January has a very specific spending rhythm. Understanding it can be the difference between landing clients and spinning your wheels.

The Budget Reality Check

Most independent schools operate on a fiscal year that runs from July to June. By January, administrators have spent about half their budget, and they’re getting a clearer picture of what’s left.

Some line items came in under budget. Others got blown out by unexpected expenses. And there’s a particular type of money that becomes available right around now: the “use it or lose it” funds.

I can’t tell you how many times I sat in leadership meetings in January where someone said, “We have $15,000 left in professional development that we need to spend before June, or it disappears.”

What They’re NOT Buying

January is not the time for big strategic initiatives. Schools are mid-year. They’re not reinventing their marketing strategy or overhauling their admissions process. They’re executing on plans that were made last spring.

If you’re pitching something that requires a fundamental shift in how a school operates, you’re six months too late. Or six months early for next year.

What They ARE Buying

January purchases fall into three categories.

Problem-solving purchases. Something broke, and they need to fix it now. These are reactive buys that happen fast.

Leftover budget purchases. Workshops, software, and consulting projects that can be scoped and completed before June.

Planting seeds for next year. Smart administrators are already thinking about next year’s budget, with requests typically due by February or March. If you want to be in that budget, you need to be having conversations now. Not selling. Conversing.

The Access Problem

One more thing: everyone just got back. Inboxes are overflowing. Don’t expect fast responses the first week of January. By the second and third week, things stabilize, and real conversations can happen.

The fall sprint was finally over. Back-to-school nights, parent conferences, the relentless rhythm of early dismissals, and faculty meetings. By the time November rolled around, I was running on fumes. That Wednesday before Thanksgiving felt like crossing a finish line. Four days of not setting an alarm. Four days of eating leftovers, watching football, and hoping this is the year Ohio State will beat Michigan after four straight losses.

This week felt different, though.

I woke up Wednesday morning and realized nobody was giving me permission to stop. There was no Head of School sending the “enjoy your well-deserved break” email. No collective sigh in the faculty room. Just me, my laptop, and a to-do list that doesn’t care about the academic calendar.

Here’s what I’ve learned about holiday seasons as an entrepreneur: breaks aren’t breaks anymore. They’re opportunities.

That sounds hustle-culture toxic, I know. But hear me out.

When schools go quiet, inboxes go quiet. Decision-makers aren’t buried in the daily chaos of running a building. That head of school you’ve been trying to reach? She might actually have ten minutes to read your email. That proposal you sent three weeks ago? It might finally get the attention it deserves.

I’m not saying I worked through the entire long weekend. I didn’t. I ate too much pie and watched the Lions lose, just like everyone else.

But I also spent a few hours this morning doing the kind of deep work that’s impossible during a normal week. No Slack notifications. No calls to return. Just focused time to think about where the business is headed and what I want to build next.

The old rhythm is gone. I’m still figuring out the new one.

If you’re considering making this leap, know that the calendar you’ve lived by for years won’t matter the same way anymore. That’s disorienting at first. But there’s also freedom in it. You get to decide what a break means now.

Nobody’s giving you permission to rest. But nobody’s stopping you from working either.

You’re the one who gets to choose.

Here’s the pattern I keep seeing. The people who typically leave schools to start their own businesses are senior administrators or heads of school. These aren’t assistant teachers or department chairs making this transition. They’re people at the top of the organizational chart.

Why does this matter? Because these are the people who had “people.”

You know what I mean by “people.” I’m talking about the support system and support staff that came with your position. Need to schedule an appointment? Someone handles that. Document needs proofreading? There’s someone for that. Administrative task that needs completing? You delegate it.

When you go out on your own, that entire infrastructure vanishes overnight.

Suddenly, every single task defaults to you. Schedule that appointment? That’s you. Proofread this document? That’s you. Handle this administrative detail? Also you. You don’t have people anymore. You are the people.

I’ve watched several colleagues make this transition and struggle with this reality in ways they never anticipated. They were brilliant educational leaders who could manage complex institutions, but they found themselves drowning in the minutiae they used to delegate without a second thought.

This isn’t an insurmountable problem. But it is a problem you need to solve before you make the transition, not after you’re already struggling to keep your head above water.

Here’s what I encourage you to do: Before you leave your current position, conduct an honest audit. Catalog every bit of support you rely on during a typical week or month. Write it all down. Every task someone else handles for you, every administrative detail that gets taken care of without your direct involvement.

Then ask yourself the hard questions: Which of these tasks can I realistically handle myself? Which ones do I need to outsource to a virtual assistant or contractor? Are there other solutions I haven’t considered?

This exercise might feel tedious, but it’s critical. You need to know exactly what you’re taking on before you’re the only person available to take it on.

The freedom of entrepreneurship is real. But so is the reality that you’re now responsible for everything. Plan accordingly.

It’s not personal. It’s not even bad. It’s just reality.

I’ve experienced this myself, and I’ve heard the same story from other consultants who’ve made the leap from working in schools to working with schools. You create something great, offer it free to build goodwill, and people show up. They engage. They thank you. You feel validated.

Then you announce the paid version, and the enthusiasm evaporates.

The Only Validation That Matters

Here’s the shift I wish I’d made earlier: stop asking people if they think something is a good idea. When you ask for advice, people will almost always be encouraging. This feedback feels good, but it’s nearly worthless as a business metric.

The only real validation that matters is whether someone will pay for what you’re offering. Payment is commitment. Payment is proof that your solution solves a real problem.

If you’re thinking about creating an online course, developing a training program, or launching any initiative that requires significant time, try this instead: get people to pay for it first. Not after you’ve spent 40 hours creating it. Before you build it.

This approach validates actual demand rather than hypothetical interest. It protects your time from being invested in offerings that won’t generate revenue. And it forces you to articulate your value proposition clearly enough that someone will commit money to it.

The Transition Reality

When you spend 28 years in schools, you assume your expertise will easily translate into a thriving consulting business. And it can, but not automatically. The transition from colleague to consultant requires you to think differently about value.

Inside schools, your value was recognized through your salary and title. Outside schools, your value must be recognized through someone deciding that what you offer is worth more than keeping that money for something else.

Free and paid operate in completely different psychological spaces. Free is easy, requires no justification, and can be consumed casually. Paid requires deliberation, approval, budget allocation, and accountability. Paid means someone believes you’re worth it.

Moving Forward

If I could go back and give myself advice from the early days, it would be this: trust your value enough to ask for payment earlier. Test your ideas with real financial commitment rather than hypothetical enthusiasm.

The people who pay attention for free might genuinely benefit from what you offer. But the people who pay, period, are the ones who will build your business. Learn to distinguish between the two, and invest your limited time accordingly.

This doesn’t make you mercenary. It makes you sustainable. And sustainability is what allows you to keep serving schools and educators for the long term.

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.

Here’s the truth bomb: Social media is not real.

I know, I know—you’ve probably heard this before. But let me tell you why it matters specifically for those of us who’ve left the school world to hang our own shingle.

The Comparison Trap

When you’re in the thick of building your consulting business, it’s natural to look around and see what others are doing. You scroll through LinkedIn and see another education consultant posting about their latest big contract. You check Instagram and find someone celebrating their fifth school partnership this month. You read a Twitter thread from a former administrator who seems to have it all figured out, complete with a perfectly branded website and a waiting list of clients.

And then you look at your own situation—maybe you’re still figuring out your pricing, or you just had a proposal rejected, or you haven’t landed a client in three weeks—and you think: What am I doing wrong?

Here’s what you need to hear: They might not be doing better than you. They might not be doing more than you. They might be in the exact same place as you.

The Curation Game

Social media is a highlight reel. It’s a carefully curated window into someone’s professional life. When I post about a successful workshop presentation or a new client, you’re not seeing the three proposals that got turned down that same month. You’re not seeing the nights I spent questioning my pricing strategy or wondering if I should launch a new product.

The consultant who posts about their packed calendar? They’re probably not posting about the cancellation they got last week or the invoice that’s 60 days overdue. The person celebrating their “best quarter yet”? They’re likely not sharing that they’re still figuring out their retirement contributions or that they took a financial hit to invest in a marketing system that hasn’t paid off yet.

The Reality for New Consultants

This is particularly important for those of us who are new to entrepreneurship but not new to education. After 28 years in schools, I had credibility in my field—but I was starting from scratch as a business owner. And in those early months (honestly, even now), it’s easy to look at other consultants’ social media presence and feel like you’re falling behind.

But here’s what I’ve learned: Most of us are doing roughly the same amount of work and are in roughly the same place. The main difference is that some people post about it on social media, and some people don’t.

The person with the polished LinkedIn presence and regular posts might have one client. You might have one client. The difference isn’t in the business success—it’s in the social media strategy.

Why This Matters

I’m sharing this because I don’t want you to get discouraged. I don’t want you comparing your internal reality—with all its doubts, setbacks, and learning curves—to someone else’s external presentation. That’s not a fair fight, and it’s not an accurate comparison.

When you’ve spent decades in the structured environment of schools, with clear metrics of success and regular feedback, the ambiguity of entrepreneurship can be disorienting. Adding the distortion of social media comparison on top of that? It’s a recipe for unnecessary self-doubt.

The Bottom Line

As you build your business serving schools, remember this: Social media is smoke and mirrors. It’s strategic. It’s curated. It’s often more about building a brand than reflecting day-to-day reality.

That consultant who seems to have it all together? They’re probably figuring it out just like you are. They’re just posting about their wins and keeping their struggles private—which is a perfectly valid social media strategy, but it’s not the whole story.

So keep doing your work. Keep building your relationships. Keep learning the business side of this new career. And if you find yourself scrolling through social media and feeling inadequate? Close the app and get back to the actual work of building your business.

Because that’s what’s real. That’s what matters. And that’s where your focus belongs.

Here’s what I’ve discovered: there’s something almost sacred about the physical act of leaving your workspace and coming home. For nearly three decades, I had an office persona and a home persona. I’d walk through my front door, and while I occasionally opened my laptop after dinner to finish something urgent, there was a clear delineation. Work happened there. Home happened here.

Now my office is down the hall.

And I’m realizing this might be one of the most challenging aspects of entrepreneurship that nobody adequately warned me about.

The Slow Creep of Always-On

The transition happened in stages. At first, working from home felt wonderfully strange and foreign. I’d sit at my desk thinking, “What am I even doing today?” There was an adjustment period where the freedom felt almost uncomfortable. Then I crossed into what I thought was the sweet spot—I loved working at home, loved the flexibility, loved being able to structure my day however I wanted.

But somewhere along the way, I crossed another threshold. The one where “I can work whenever I want” became “I’m working all the time.”

I’m still doing family things. I’m still engaging with the people I love. But if I’m honest with myself—and that’s what this Substack is about—I’ve noticed I’m always working. A quick email between dinner and dessert. A strategy session with myself while everyone else is watching TV. Refining a proposal on Saturday morning. Checking in on client communications on Sunday afternoon.

It’s getting to an unhealthy place, and I’m aware enough to recognize it, even if I haven’t figured out how to fix it yet.

The Guard Rails I Wish I’d Built Earlier

When you work at a school, the structure is built in. The bell schedule, the faculty meetings, the academic calendar—they all create natural boundaries. Even the most dedicated educators eventually go home (even if home includes a bag full of papers to grade).

But when you’re building a business that serves schools? When every email could be the next client, every hour you’re not working feels like a missed opportunity, and every moment of rest whispers that you should be doing more? The boundaries dissolve.

I’m sharing this not because I have the solution figured out, but because I wish someone had told me to think about this on day one. Here’s what I’m learning I should have done from the start:

Create physical boundaries. Even if your office is at home, treat it like it’s somewhere else. Define when you’re “at work” and when you’re “at home”—even if they’re just rooms apart.

Set actual working hours. I know, I know—one of the perks of entrepreneurship is flexibility. But unlimited flexibility can become unlimited work.

Build in rituals. When you don’t have a commute to create transition space, you need to manufacture it. A walk around the block. A dedicated “end of workday” routine. Something that signals to your brain: work is done.

The Uncomfortable Honesty

I don’t have a tidy conclusion here. I’m not going to wrap this up with “here’s how I solved it” because I haven’t. What I can offer is the awareness that this is real, and if you’re considering leaving your school position to start a business, this is something you need to think about now, not later.

The irony isn’t lost on me: I spent 28 years helping students and colleagues find balance, structure their time, and set healthy boundaries. Now I’m struggling to do the same for myself.

Maybe that’s the most important lesson of all. Knowing what you should do and actually doing it are two very different things—especially when you’re building something from scratch and every hour feels precious.

So if you’re already on this entrepreneurial path: How are you managing this? What guardrails have you put in place?

And if you’re contemplating making the leap: Think about this now. Because the freedom of working from home is real, but so is the danger of never actually leaving work.

I’m still figuring this out. I’ll let you know when I get it right.

After building SchneiderB Media over the past decade, more directly over the last three years, I've had a lot of sales conversations. I've pitched services, negotiated contracts, and closed deals. I'm comfortable talking about pricing, value propositions, and ROI.

But here's what I discovered: The most successful sales conversations I have don't feel like selling at all.

They feel like research.

The Reframe That Changed Everything

Early in my entrepreneurial journey, I noticed a pattern. My best client relationships started not with me pitching my services, but with me genuinely trying to understand their challenges.

And something interesting happened: When you ask for advice, people sell themselves.

Why This Works for Former Educators

1. It's authentic to who we are
As educators, we're naturally curious. We ask questions, listen, and help people figure things out. This isn't a sales tactic—it's just teaching in a different context.

2. It flips the power dynamic
Instead of being the vendor seeking business, you become the expert seeking insights. You're positioning yourself as someone building something valuable.

3. People love giving advice
When you genuinely seek their input, you're not interrupting their day—you're making it better.

My Framework

The Setup: "I'm working on something and could really use your perspective..."

The Core Question: "What's the biggest challenge you're facing with [relevant topic]?"

The Follow-Up: "What would an ideal solution look like from your perspective?"

The Bridge: "That's exactly the kind of problem I'm trying to solve. Would you be interested in hearing how I'm approaching it?"

Notice what's happening here. I'm not pitching. I'm simply sharing a solution to a problem they just told me they have.

The Bottom Line

People want to buy from former educators because we understand schools from the inside. But that only matters if they believe we understand their specific situation.

The fastest way to demonstrate understanding isn't to tell them what they need—it's to ask them what they think they need.

Your next client conversation shouldn't begin with your elevator pitch. It should start with genuine curiosity about their world.

When you finally do present your solution, it won't feel like selling at all. It'll feel like teaching. Which is exactly what it should be.

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.

You know that colleague who teaches three different subjects, coaches two sports, runs the school newspaper, and somehow finds time to organize the faculty holiday party? In schools, we celebrate these multi-talented workhorses—and rightfully so. The ability to wear multiple hats isn't just valued in education; it's practically a job requirement.

But here's what I've learned the hard way: this "good at everything" superpower that makes you indispensable in schools can actually sabotage your business.

The Clarity Problem

I've spoken with numerous school officials recently who are considering making the switch or have already transitioned to full-time entrepreneurship. The pattern is always the same. They launch with a dizzying array of service offerings because, well, they can do all those things.

The problem? Schools looking at their website or marketing materials have no idea what they actually do. When you offer everything, you're known for nothing.

The One-Thing Rule

Someone shared this advice with me, and it's been game-changing: Think in ones.

• One product offering

• One marketing tactic

• One person or persona you're selling to

Start by getting really good at that focused approach. Master it. Become known for it. Then you can expand.

This goes against every instinct we've developed in schools, where success often means juggling multiple responsibilities simultaneously. But in business, especially when you're starting out, focus trumps versatility.

Making the Shift

Your decades in education aren't wasted—they're your competitive advantage. But that advantage only works when you can clearly articulate exactly how you help schools. Instead of "I do curriculum and training and consulting and strategic planning," try "I help middle schools increase student engagement through project-based learning implementation."

See the difference? One is a laundry list. The other solves a specific problem for a specific audience.

The beauty of starting focused isn't that you'll never expand—it's that you'll expand from a position of strength and clarity rather than confusion.

So if you're contemplating this leap or already in the thick of it, ask yourself: What's your one thing? What specific problem do you solve better than anyone else for a clearly defined group of schools?

Start there. Get known for that. Everything else can wait.

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.